Title of Invention	INDOLINONES OF GENERAL FORMULA I
Abstract	The present invention relates to indolinones of general formula substituted in the 6 position, wherein R1 to R5 and X are defined as in claim 1, the isomers and the salts thereof, particularly the physiologically acceptable salts thereof which have valubale pharmacological properties esecially an inhibitory effect on receptor tyrosine kinases, and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumour cells, pharmaecutical compositions containing these compounds their use and processes for preparing them.

Title of Invention

INDOLINONES OF GENERAL FORMULA I

Abstract

The present invention relates to indolinones of general formula substituted in the 6 position, wherein R1 to R5 and X are defined as in claim 1, the isomers and the salts thereof, particularly the physiologically acceptable salts thereof which have valubale pharmacological properties esecially an inhibitory effect on receptor tyrosine kinases, and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumour cells, pharmaecutical compositions containing these compounds their use and processes for preparing them.

Full Text	FORM 2 THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS RULES, 2006 COMPLETE SPECIFICATION [See Section 10; rule 13] "INDOLINONES OF GENERAL FORMULA I" BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG., a German company of 55216 Ingelheim am Rhein, Germany, GRANTED 25-06-2007 The following specification particularly describes the invention and the manner in which it is to be performed: The present invention relates to new indolinones of general formula (I), substituted in the 6 position, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof which have valuable properties. The above compounds of general formula I wherein R^ denotes a hydrogen atom or a prodrug group have valuable pharmacological properties, in particular an inhibiting effect on various kinases, especially receptor tyrosine kinases such as VEGFR2, PDGFRa, PDGFRP, FGFR1, FGFR3, EGFR, HER2, IGF1R and HGFR, as well as complexes of CDK"s (Cyclin Dependent Kinases) such as CDK1, CDK2, CDK3, CDK4, CDK5, CDK6, CDK7, CDK8 and CDK9 with their specific cyclins (A, Bl, B2, C, Dl, D2, D3, E, F, Gl, G2, H, I" and K) and to viral cyclin (cf. L. Mengtao in J. Virology .71(3), 1984-1991 (1997)), and on the proliferation of cultivated human cells, in particular endothelial cells, e.g. in angiogenesis, but also on the proliferation of other cells, in particular tumour cells. The other compounds of the above general formula I wherein Rx does not denote a hydrogen atom or a prodrug group are valuable intermediate products for preparing the abovementioned compounds. The present invention thus relates to the above compounds of general formula I, whereby those compounds wherein Rj_ denotes a hydrogen atom or ,k prodrug group have valuable pharmacological properties, pharmaceutical compositions containing the pharmacologically active compounds, the use thereof and processes for preparing them. In the above general formula I X denotes an oxygen or sulphur atom, Rx denotes a hydrogen atom or a prodrug group such as a Cx.4-alkoxycarbonyl or C2.4-alkanoyl group, R2 denotes a carboxy group, a straight-chain or branched C^g-alkoxy-carbonyl group, a C4_7-cycloalkoxy-carbonyl or an aryloxycarbonyl group, a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C^-alkoxy-carbonyl, aminocarbonyl, C-L.-j-alkylamino-carbonyl or di-(C^3-alkyl)-aminocarbonyl group, a straight-chain or branched C2.6-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, C1.3-alkoxy, amino, C^-alkylamino or di-(Cx„3-alkyl)-amino group, an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C-^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (C^s-alkyl) -Cj.-j-alkylaminocarbonyl-phenyl group, it may also denote a di- (Cx.2-alkyl) -aminocarbonyl group, R3 denotes a hydrogen atom, a C^-alkyl, C3_7-cycloalkyl, trifluoromethyl or heteroaryl group, a phenyl or naphthyl group, a phenyl or naphthyl group mono-or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C^-alkyl or C^-alkoxy group, whilst in the event of disubstitution the substituents may be identical or different and wherein the abovementioned unsubstituted as well as the mono- and disubstituted phenyl and naphthyl groups may additionally be substituted by a hydroxy, hydroxy-C1_3-alkyl or C^-alkoxy-C^-alkyl group, by a cyano, carboxy, carboxy-C-^-alkyl, C^-alkoxycarbonyl, aminocarbonyl, C1.3-alkylamino-carbonyl or di- (C^j-alkyl)-aminocarbonyl group, by a nitro group, by an amino, C^-alkylamino, di- (C^-alkyl) -amino or amino-C^.-,-alky 1 group, by a C^-alkylcarbonylamino, N~ (C1_3-alkyl) -C^-alkyl- carbonylamino, C1_3-alkylcarbonylamino-C1_3-alkyl, N- (C1.3-alkyl) -C1.3-alkylcarbonylamino-C1.3-alkyl, C^-alkyl- sulphonylamino, C^-alkylsulphonylamino-Ci.-j-alkyl, N- (C^-alkyl) -C^-alkylsulphonylamino-C^-alkyl or aryl-C^-alkylsulphonylamino group, by a cycloalkylamino, cycloalkyleneimino, cyclo-alkyleneiminocarbonyl, cycloalkyleneimino-C^-alkyl, cycloalkyleneiminocarbonyl-C^^^-alkyl or cycloalkyleneiminosulphonyl-C^-alkyl group having 4 to 7 ring members in each case, whilst in each case the methylene group in position 4 of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH or -NCC^-alkyl) group, or by a heteroaryl or heteroaryl-C^-alky 1 group, R4 denotes a C3.7-cycloalkyl group, whilst the methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be substituted by an amino, C^-alkylamino or di- (C^-alkyl) -amino group or replaced by an -NH or -NCC^-alkyl) group, or a phenyl group substituted by the group R6, which may additionally be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by Cx.5-alkyl, trifluoromethyl, hydroxy, C1.3-alkoxy, carboxy, C1.3-alkoxycarbonyl, amino, acetylamino, C^-alkyl-sulphonylamino, aminocarbonyl, C^-alkyl-aminocarbonyl, di- (C^-alkyl)-aminocarbonyl, aminosulphonyl, C1.3 - alkyl - aminosulphonyl, di- (C^-alkyl)-aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different and wherein R6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, a cyano, nitro, amino, C^-alkyl, C3_7-cycloalkyl, trifluoromethyl, phenyl, tetrazolyl or heteroaryl group, the group of formula wherein the hydrogen atoms bound to a nitrogen atom may in each case be replaced independently of one another by a C^-alkyl group, a C1.3-alkoxy group, a C^-alkoxy-C^-alkoxy, phenyl-C10-alkoxy, amino-C2„3-alkoxy, C1_3-alkylamino-C2_3-alkoxy, di- (C^-alkyl) -amino-C2.3-alkoxy, phenyl-C^-alkylamino-C2.3-alkoxy, N- (C^-alkyl) -phenyl-C^-alkylamino-Cj.-j-alkoxy, C5_7-cycloalkyleneimino-C2_3-alkoxy or C-L.-j-alkylmercapto group, a carboxy, C1.4-alkoxycarbonyl, aminocarbonyl, C1.3-alkyl-amino-carbonyl, N- (C^g-alkyl) -C^-j-alkylaminocarbonyl, phenyl- C^3 -alkylamino-carbonyl, N- (C^-alkyl) -phenyl-C1.3-alkylamino-carbonyl, piperazinocarbonyl or N- (C1.3-alkyl) -piperazinocarbonyl group, a C^-alkylaminocarbonyl or N- (C^-alkyl) -C1.3-alkylaminocarbonyl group wherein an alkyl moiety is substituted by a carboxy or C^-alkoxycarbonyl group or in the 2 or 3 position by a di- (C^-alkyl) -amino, piperazino, N- (C^-alkyl) -piperazino or a 4- to 7-membered cycloalkyleneimino group, a C3.7 - eye loalkyl-carbonyl group, wherein the methylene group in the 4 position of the 6- or 7-membered cycloalkyl moiety may be substituted by an amino, C1.3-alkylamino or di- (C^3-alkyl) -amino group or replaced by an -NH or -NCC^-alkyl) group, a 4- to 7-membered cycloalkyleneimino group wherein a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or the cycloalkylene moiety may be fused to a phenyl ring or one or two hydrogen atoms may each be replaced by a C1_2-alkyl group and/or in each case the methylene group in the 4 position of a 6-or 7-membered cycloalkyleneimino group may be substituted by a carboxy, Cj._3-alk0xycarb0n.yl, aminocarbonyl, Cj._3-alkylamir.0carb0r.yl, di- (C^j-alkyl) -aminocarbonyl, phenyl-C1_3-alkylatnino or N-(C1.3-alkyl)-phenyl-Cj._3-alkylamino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1_3-alkyl) , -N(phenyl), -N (C^-alkyl-carbonyl) or -N.(benzoyl) group, a C1_4-alkyl group substituted by the group R7, wherein R7 denotes a C3.7-cycloalkyl group, whilst the methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be substituted by an amino, Cj,_3-alkylamino or di- (C1_3-alkyl) -amino group or replaced by an -NH or -N (C1_3-alkyl) group or in a 5- to 7-membered cycloalkyl group a -(CH2)2 group may be replaced by a -CO-NH group, a -(CH2)3 group may be replaced by a -NH-CO-NH or -CO-NH-CO group or a -(CH2)4 group may be replaced by a -NH-CO-NH-CO group, whilst in each case a hydrogen atom bound to a nitrogen atom may be replaced by a C1_3-alkyl group, an aryl or heteroaryl group, a hydroxy or C1.3-alkoxy group, an amino, C^-alkylamino, di-(C1.7-alkyl)-amino, phenylamino, N-phenyl-C^-alkyl-amino, phenyl-C^.-j-alkyl-amino, N- (C^-alkyl) -phenyl-C^-alkylamino or di-(phenyl-C1.3-alkyl) -amino group, an co-hydroxy-C2_3-alkyl-amino, N- (C^-alkyl) -co-hydroxy-C2_3-alkyl-amino, di- (co~ hydroxy-C2_3-alkyl) -amino, di- (co- (C^-alkoxy) -C2,3-alkyl) -amino or N~ (dioxolan-2-yl) -C1.3-alkyl-amino group, a C1^3-alkylcarbonylamino-C2_3-alkyl-amino or C^-alkylcarbonylamino-Cj.-j-alkyl-N- (Cx..3-alkyl) -amino group, a C1.3-alkylsulphonylamino, N-(C^-alky!)-C^.-j-alkyl-sulphonylamino, C^-alkylsulphonylamino-C^-alkyl-amino or C-^-alkylsulphonylamino-C^-alkyl-N- (C^-alkyl) -amino group, a hydroxycarbonyl-C1.3-alkylamino or N- (C^-alkyl) -hydroxycarbonyl-Cj^.3-alkyl-amino group, a guanidino group wherein one or two hydrogen atoms may each be replaced by a C^-alky! group, a group of formula -N(R8) -CO- (CH2)n-R9 (ID, wherein R8 denotes a hydrogen atom or a C^-alkyl group, n denotes one of the numbers 0, 1, 2 or 3 and R9 denotes an amino, C1.4-alkylamino, di- (C^-alkyl)-amino, phenylamino, N- (C^-alkyl)-phenylamino, benzylamino, N-(C^-alkyl)-benzylamino or C^-alkoxy group, a 4- to 7-membered cycloalkyleneimino group, whilst in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -NCC^-alkyl) , -N(phenyl), -N (C^-alkyl-carbonyl) or -N(benzoyl) group, or, if n denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom, a group of formula -N(R10)-(CH2)m-(C0)o-R11 (III), wherein R10 denotes a hydrogen atom, a C1.3-alkyl group, a C1_3-alkylcarbonyl, arylcarbonyl, phenyl-^.3-alkyl-carbonyl, C^j-alkylsulphonyl, arylsulphonyl or phenyl-C1^-alkylsulphonyl group, m denotes one of the numbers 1, 2, 3 or 4, o denotes the number 1 or, if m denotes one of the numbers 2, 3 or 4, o may also denote the number 0 and RX1 denotes an amino, C^-alkylamino, di- (C^-alkyl)-amino, phenylamino, N- (C-^-alkyl) -phenylamino, benzylamino, N-(C2.4-alkyl)-benzylamino, C^-alkoxy or C^-alkoxy-C-^-alkoxy group, a di- (C^-alkyl) -amino-C^-alkylamino group optionally substituted in the 1 position by a C^-alkyl group or a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1.3-alkyl) , -N(phenyl) , -N(Cl.3-alkyl-carbonyl) or -N(benzoyl) group, a C4_7-cycloalkylamino, C4_7-cycloalkyl-C1_3-alkylamino or C4.7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond and wherein the abovementioned groups may each additionally be substituted at the amino-nitrogen atom by a C5.7-cycloalkyl, C2.4-alkenyl or C^-alkyl group, a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C^-alkyl, C^-alkoxy or amino group, and/or one or two hydrogen atoms may each be replaced by a C^-alkyl, Cs.7-cycloalkyl or phenyl group and/or the methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C^-alkyl, C1_3-alkoxy or Cj.j-alkoxy-C^-alkyl group, the methylene group in the 3 or 4 position of a 6- or 7-membered cycloalkyleneimino group may in each case be substituted by a hydroxy, hydroxy-C^3 -alkyl, C^-alkoxy, C1,3-alkoxy-C1.:3-alkyl, carboxy, C1_4 - alkoxycarbonyl, aminocarbonyl, C^-alkylaminocarbonyl, di- (C^-alkyl) -aminocarbonyl, phenyl-Cj.3-alkylamino or N- (C^-alkyl) -phenyl-C^-alkyl-amino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1.3-alkyl-) , -N (phenyl) , -N(phenyl-C^-alkyl-) , -N(C1^3-alkyl-carbonyl-) , -N(C1.4-hydroxy-carbonyl-) , -N (C^-alkoxy-carbonyl- ) , -N(benzoyl-) or -N(phenyl-C^.3-alkyl-carbonyl-) group, wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5-to 7-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group, or R6 denotes a C^-alkyl group which is substituted by a carboxy, Cx.3-alkoxycarbonyl, aminocarbonyl, C^-alkylaminocarbonyl or di- (C^-alkyl) -aminocarbonyl group or by a 4- to 7-membered cycloalkyleneiminocarbonyl group, an N- (Cj^-alkyl) -C2_4-alkanoylamino group which is additionally substituted in the alkyl moiety by a carboxy or Cx.3-alkoxycarbonyl group, a group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12 denotes a hydrogen atom, a C^-alkyl or C3.7-cycloalkyl * group or a C^-alkyl group terminally substituted by a phenyl, heteroaryl, trifluoromethyl, hydroxy, C^-alkoxy, aminocarbonyl, C^-alkylamino-carbonyl, di-(C^4-alkyl)-amino-carbonyl, C-^-alkyl-carbonyl, C^-alkyl-sulphonyl-amino, N- (C1.3-alkyl) -C^,.,--alkyl-sulphonylamino, C1.3-alkyl-amino^ulphonyl or di-(C.^-alkyl)-aminosulphonyl group and p denotes one of the numbers 0, 1, 2 or 3 and R13 assumes the meanings of the abovementioned group R7, or, if p denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom, a group of formula -N(R14)-(CH2)q-(CO)r-R15 (V), wherein R14 denotes a hydrogen atom, a C^-alkyl group, a C^-alkylcarbonyl, arylcarbonyl, phenyl-C^-alkylcarbonyl, heteroarylcarbonyl, heteroaryl-C^-alkylcarbonyl, Ci.4-alkylsulphonyl, arylsulphonyl, phenyl- Cx.3 -alkylsulphonyl, heteroaryl sulphonyl or heteroaryl -Cx_3 -alkyl -sulphonyl group, q denotes one of the numbers 1, 2, 3 or 4, r denotes the number 1 or, if q is one of the numbers 2, 3 or 4, it may also denote the number 0 and R15 assumes the meanings of the abovementioned group R7, a group of formula -N(R16)-S02-Ri7 (VI), wherein R16 denotes a hydrogen atom or a C^-alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino or N- (C^-alkyl)-trifluoromethyl-carbonyl-amino group and R17 denotes a Cx_2-alkyl group, an amino group substituted by a di- (C^-alkyl) -amino-Cx.3-alkyl-carbonyl or di- (G^-alkyl) -amino-Cx_3-alkyl-sulphonyl group and a di- (C^-alkyl) -aminocarbonyl-C1.3-alkyl group, or an N-(C^-alkyl)-C-^-alkylsulphonylamino or N- (C1.3-alkyl) -phenylsulphonylamino group wherein the alkyl moiety is additionally substituted by a cyano or carboxy group, wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under R6 may be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by C1_5-alkyl, trifluoromethyl, hydroxy, C^3-alkoxy, carboxy, C1.3-alkoxycarbonyl, aminocarbonyl, C^-alkylamino-carbonyl, di- (C^-alkyl)-amino-carbonyl, aminosulphonyl, Cx.3 -alkyl -aminosulphonyl, di- (Ci.j-alkyl) -aminosulphonyl, C^-alkyl-sulphonylamino, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group, and Rs denotes a hydrogen atom or a C^-alkyl group, wherein by an aryl group is meant a phenyl or naphthyl group optionally mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a cyano, trifluoromethyl, nitro, carboxy, aminocarbohyl, C^-alkyl or C^-alkoxy group and by a heteroaryl group is meant a monocyclic 5- or 6-membered heteroaryl group optionally substituted by a C^-alkyl group in the carbon skeleton, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted by a C^-alkyl or phenyl-C1.3i-alkyl group, an oxygen or sulphur atom or an imino group optionally substituted by a C1.3-alkyl or phenyl-^.3-alkyl group or an oxygen or sulphur atom and additionally a nitrogen atom or an imino group optionally substituted by a C1_3-alkyl or phenyl-Ci.3-alkyl group and two nitrogen atoms, and moreover a phenyl ring may be fused to the abovementioned monocyclic heterocyclic groups via two adjacent carbon atoms and the bonding takes place via a nitrogen atom or via a carbon atom of the heterocyclic moiety or a fused phenyl ring, some or all of the hydrogen atoms in the abovementioned alkyl and alkoxy groups or in the alkyl moieties contained in the above-defined groups of formula I optionally being replaced by fluorine atoms, the saturated alkyl and alkoxy moieties with more than 2 carbon atoms which are present in the groups defined hereinbefore also include the branched isomers thereof, such as for example the isopropyl, tert.butyl, isobutyl group, unless otherwise stated, and additionally the hydrogen atom of any carboxy group present or a hydrogen atom bound to a nitrogen atom, e.g. a hydrogen atom of an amino, alkylamino or imino group or a saturated N-heterocycle such as the piperidinyl group, may each be replaced by a group which can be cleaved in vivo. By a group which can be cleaved in vivo from an imino or amino group is meant, for example, a hydroxy group, an acyl group such as the benzoyl or pyridinoyl group or a C^^-alkanoyl group such as the formyl, acetyl, propionyl, butanoyl, pentanoyl or hexanoyl group, an allyloxycarbonyl group, a C^^-alkoxycarbonyl group such as the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, tert.butoxycarbonyl, pentoxycarbonyl, hexyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl or hexadecyloxycarbonyl group, a phenyl-C.^-alkoxycarbonyl group such as the benzyloxycarbonyl, phenylethoxycarbonyl or phenylpropoxycarbonyl group, a C^-alkylsulphonyl-C2_4 - alkoxycarbonyl, C^ - alkoxy- C2.4 - alkoxy- C2_4 - alkoxycarbonyl or ReCO-0- (RfCRg) -0-C0 group wherein Re denotes a C^g-alkyl, C5,7-cycloalkyl, phenyl or phenyl-CJ.J-alkyl group, R£ denotes a hydrogen atom, a C10-alkyl, C5.7-cycloalkyl or phenyl group and Rg denotes a hydrogen atom, a C^-alkyl or ReCO-0- (RECRg) -0 group wherein Re to Rg are as hereinbefore defined, wherein additionally the amino group may be a phthalimido group, whilst the abovementioned ester groups may also be used as a group which cari be converted in vivo into a carboxy group. One sub-group of compounds of general formula I which deserves special mention comprises those wherein X, R1 and R3 to R5 are as hereinbefore defined and R2 denotes a straight-chain or branched C^.g-alkoxy-carbonyl group, a C4_7-cycloalkoxycarbonyl or a aryloxycarbonyl group, a straight-chain or branched C^g-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C^-alkoxycarbonyl, aminocarbonyl, C^-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group, a straight-chain or branched C2„6-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, C^-alkoxy, amino, C^-alkylamino or di- (C1_3-alkyl) -amino group, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. A second sub-group of compounds of general formula I which deserves special mention comprises those wherein X, R-L and R3 to R5 are as hereinbefore defined and R2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1.3-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (Ci.s-alkyl) -C^-alkylaminocarbonyl-phenyl group, R2 may also denote a di- (C^-alkyl)-aminocarbonyl group, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. A third sub-group of compounds of general formula I which deserves special mention comprises those wherein X, Rx to R3 and R5 are as hereinbefore defined and R4 denotes an R7-(C^-alkyl)-phenyl group, wherein R7 denotes an amino, C^-alkylamino, di- (C^-alkyl) -amino, phenylamino, N-phenyl-C^3-alkyl-amino, phenyl-C^-alkyl-amino, N- (C^-alkyl) -phenyl-C1.3-alkylamino or di- (phenyl-0^3-alkyl) -amino group, or a phenyl group substituted by the group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12, p and R13 are as hereinbefore defined, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. Preferred compounds of general formula I are those wherein Rx and R3 are as hereinbefore defined and X denotes an oxygen atom, R2 denotes a carboxy group, a straight-chain or branched C^.g-alkoxy-carbonyl group, a C5_7-cycloalkoxycarbonyl or a phenoxycarbonyl group, a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C-^-alkoxycarbonyl, aminocarbonyl, C^j-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group, a straight-chain or branched C2^3-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a chlorine atom, by a hydroxy, C^-alkoxy, amino, C^-alkylamino or di- (C^.j-alkyl) -amino group, an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N~ (C^-alkyl) -C-L.3-alkylaminocarbonyl-phenyl group, it may also denote a di-(C^-alkyl)-aminocarbonyl group, R4 denotes a C3.7-cycloalkyl group, whilst the methylene group in the 4 position of a 6- or 7-membered oycloalkyl group may be substituted by an amino, C^j-alkylamino or di- (C^-alkyl)-amino group or replaced by an -NH or -N(C1_3-alkyl) group, or a phenyl group substituted by the group R6, which may additionally be mono- or disubstituted by fluorine, chlorine or bromine atoms, by C^-alkyl, trifluoromethyl, hydroxy, C^-alkoxy, carboxy, C^-alkoxycarbonyl, amino, acetylamino, aminocarbonyl, C1_3 - alkyl - aminocarbonyl, di-(C^j-alkyl)-aminocarbonyl, nitro or cyano groups, wherein the substituents may be identical or different and wherein R6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, a cyano, nitro, amino, C^.j-alkyl, C3_7-cycloalkyl, trifluoromethyl, phenyl, tetrazolyl or heteroaryl group, the group of formula wherein a hydrogen atom bound to the nitrogen atom may be replaced by a C^-alkyl group, a C^-alkoxy group, an amino-C2_3-alkoxy, C^-alkylamino-C2.3-alkoxy, di- (C1.3-alkyl) -amino-C2_3-alkoxy, phenyl-C1_3-alkylamino-C2_3-alkoxy, N- (C^-alkyl) -phenyl-C1.3-alkylamino-C2_3-alkoxy, pyrrol idino-C2_3-alkoxy, piperidino-C2_3-alkoxy or C^-alkylmercapto group, a carboxy, Cw-alkoxycarbonyl, aminocarbonyl, C^.,-alkyl -amino-carbonyl, phenyl -C-^-alkylamino-carbonyl or N- (C-^-alkyl) -phenyl-C1.3-alkylamino-carbonyl group, a C3_7-cycloalkyl-carbonyl group, wherein the methylene group in the 4 position of the 6- or 7-membered cycloalkyl moiety may be replaced by an -NH or -N (Cx.3 - alkyl) group, a 4- to 7-membered cycloalkyleneimino group, wherein a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or one or two hydrogen atoms may each be replaced by a C^.j-alkyl group and/or in each case th^ methylene group in the 4 position of a 6-or 7-membered cycloalkyleneimino group may be substituted by a carboxy, C^-alkoxycarbonyl, aminocarbonyl, Cx.3-alkylaminocarbonyl, di- (Cx_3-alkyl) -aminocarbonyl, phenyl-C^-alkylamino or N- (C^-alkyl) -phenyl-Cx_3-alkylamino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH or -N (C^-alkyl) group, a Cx.4-alkyl group terminally substituted by the group R7, wherein R7 denotes a C5.7-cycloalkyl group, whilst the methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be replaced by an -NH or -NlC^j-alkyl) group or in a 5- to 7-membered cycloalkyl group a -(CH2)2 group may be replaced by a -CO-NH group, a -(CH3)3 group may be replaced by a -NH-CO-NH- or a -(CH2)4 group may be replaced by a -NH-CO-NH-CO group, whilst in each case a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl group, a phenyl or heteroaryl group, a hydroxy or C^-alkoxy group, an amino, C^-alkylamino, di-(C-^-alkyl)-amino, phenylamino, N-phenyl-C^-alkyl-amino, phenyl-C^-alkylamino, N- (C1_3-alkyl) -phenyl-C^-alkylamino or di- (phenyl-Q.1_3-alkyl) -amino group, a co-hydroxy-C2^3-alkyl-amino, N- (C^-alkyl) -©-hydroxy--C2_3-alkyl-amino, di- (co-hydroxy-C2.3-alkyl) -amino, di- (00- (C^j-alkoxy) -C2.3-alkyl) -amino or N-(dioxolan-2-yl)-C^-alkyl-amino group, a C10-alkylcarbonylamino-C2_3-alkyl-amino or C1_3-alkylcarbonylamino-C2_3-alkyl-N- (G^-alkyl) -amino group, a C^-alkylsulphonylamino, N- (C^-alkyl) -C^-alkylsulphonylamino, Cj^^-alkylsulphonylamino--C2_3-alkyl-amino or C1_3-alkylsulphonylamino-C2_3-alkyl--N- (Ci.j-alkyl) -amino group, a hydroxycarbonyl-C1.3-alkylamino or N- (C^.-j-alkyl) -hydroxycarbonyl-Ci^-alkyl-amino group a guanidino group wherein a hydrogen atom may be replaced by a C3..3-alkyl group, a group of formula -N(R8)-CO-(CH2)n-R9 (II), wherein R8 denotes a hydrogen atom or a C^-alkyl group, n denotes one of the numbers 0, 1, 2 or 3 and R9 denotes an amino, C-^-alkylamino, di- (C^-alkyl) -amino, phenylamino, benzylamino or Cx.4-alkoxy group, a 5- to 7-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an -NH, -N(C1_3-alkyl) , -N(phenyl), -N (C^-alkyl-carbonyl) or -N(benzoyl) group, or, if n denotes one of the numbers 1, 2"or 3, it may also denote a hydrogen atom, a group of formula -N(R10)-(CH2)m-(CO)0-R11 (III), wherein R10 denotes a hydrogen atom, a C^-alkyl group, a C1.3-alkylcarbonyl or C^j-alkylsulphonyl group, m denotes one of the numbers 1, 2 or 3, o denotes the number 1 or, if m is one of the numbers 2 or 3, o may also denote the number 0 and Rxl denotes an amino, C1.3-alkylamino, di- (C-^-alkyl) -amino, C^4-alkoxy or C1.3-alkoxy-C1.3-alkoxy group or a 5- to 7-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an -NH, -N (C^-alkyl), -N(phenyl), -NCC^-alkyl-carbonyl) or -N(benzoyl) group, a C4.7-cycloalkylamino or C4_7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond, a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl group or one or two hydrogen atoms may each be replaced by a C^-alkyl group and/or the methylene group in position 3 of the pyrrolidine group may be substituted by a hydroxy or C^-alkoxy group, in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C^-alkyl, C^-alkoxy, carboxy, C1.3-alkoxycarbonyl, aminocarbonyl, C1.3-alkylaminocarbonyl, di- (C^-alkyl) -aminocarbonyl, phenyl-C^-alkylamino or N- (C1.3-alkyl) -phenyl-C1.3-alkyl-amino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N (C^-alkyl) , -N(phenyl), -N (phenyl -C^-alkyl) , -N (Cx_3-alkyl-carbonyl) , -N(C1.4-alkoxy-carbonyl) , -N(benzoyl) or - N (phenyl - C^-j - alkyl - carbonyl) group, wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5-to 6-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group, or R6 denotes a C^--alkyl group which is terminally substituted by a carboxy, C^-alkoxycarbonyl, aminocarbonyl, C^.j-alkylaminocarbonyl or di- (C^-alkyl) -aminocarbonyl group or by a 4- to 7-membered cycloalkyleneiminocarbonyl group, a group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12 denotes a hydrogen atom, a C1.3-alkyl, Cs.7-cycloalkyl, phenyl-C1_3-alkyl or heteroaryl-Q^-alkyl group and p denotes one of the numbers 0, 1, 2 or 3 and R13 assumes the meanings of the abovementioned group R7, or, if p denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom, a group of formula -N(Ri4)-(CH2)q-(CO)r-Rxs (V), wherein R14 denotes a hydrogen atom, a C^-alkyl group, a C^-alkylcarbonyl, phenylcarbonyl, phenyl-C^3-alkyl-carbonyl, heteroarylcarbonyl, heteroaryl - C^ - alkylcarbonyl, Cx.4 -alkylsulphonyl, phenyl sulphonyl, phenyl -C^- alkyl sulphonyl -heteroarylsulphonyl or heteroaryl-Cx_3-alkyl-sulphonyl group, g denotes one of the numbers 1, 2, 3 or 4, r denotes the number 1 or if q is one of the numbers 2, 3 or 4, it may also denote the number 0 and R15 assumes the meanings of the abovementioned group R7, a group of formula -N(R16)-S02-Ri7 (VI), wherein R16 denotes a hydrogen atom or a C^-alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino or N- (C1.3-alkyl) -trifluoromethyl--carbonyl-amino group and R17 denotes a C^-alkyl group, an amino group substituted by a di- (C^-alkyl) -amino-^.3-alkyl-carbonyl or di- (C1.3-alkyl) -amino-C^-alkyl-sulphonyl group and a di- (C^-alkyl) -aminocarbonyl-C^.j-alkyl group, wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under RG may be mono-or disubstituted by fluorine, chlorine or bromine atoms, by C^-alkyl, trifluoromethyl, hydroxy, C^-alkoxy, carboxy, C^j-alkoxycarbonyl, aminocarbonyl, C^-alkyl-aminocarbonyl, aminosulphonyl, C^-alkyl-aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group, and Rs denotes a hydrogen atom or a C^-alkyl group, whilst by a heteroaryl group as mentioned above is meant a pyridinyl, pyrazinyl, pytimidinyl, pyridazinyl, pyrrolyl, furyl, thienyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl or triazolyl group optionally substituted in the carbon skeleton by a C^-alkyl group wherein a hydrogen atom bound to a nitrogen atom may be replaced by a C1.3-alkyl or phenyl-C,^,-alkyl group and wherein the 5-membered heteroaryl groups containing at least one imino group are bound via a carbon or nitrogen Atom, a hydrogen atom bound to a nitrogen atom in the abovementioned groups may be replaced by a group which can be cleaved in vivo, particularly by an acetyl or tert.butoxycarbonyl group, the carboxy groups contained in the abovementioned groups may each be substituted by a group which can be cleaved in vivo and may occur, for example, in the form of the tert.butoxycarbonyl group, some or all of the hydrogen atoms in the abovementioned alkyl and alkoxy groups or in the alkyl moieties contained in the above-defined groups of formula I optionally being replaced by fluorine atoms and the saturated alkyl and alkoxy moieties contained in the abovementioned groups, which contain more than 2 carbon atoms, may be straight-chain or branched, unless otherwise stated, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. One subgroup of preferred compounds of general formula I deserving- special mention comprises those wherein X, Rx and R3 to R5 are as hereinbefore defined and • R2 denotes a straight-chain or branched C^-alkoxy-carbonyl group, a Cs_7-cycloalkoxycarbonyl or a phenoxycarbonyl group, a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl-carboxy, C^-alkoxycarbonyl, aminocarbonyl, C^-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group, a straight-chain or branched C2.3-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a hydroxy, C^.j-alkoxy, amino, C^-alkylamino or di- (C^-alkyl) -amino group, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. A second sub-group of preferred compounds of general formula I deserving special mention comprises those wherein X, Rx and R3 to R5 are as hereinbefore defined and R2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N-(C^-alkyl)-C^-alkylaminocarbonyl-phenyl group, R2 may also denote a di- (C1.2-alkyl) -aminocarbonyl group, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. A third sub-group of preferred compounds of general formula I deserving special mention comprises those wherein X, Rx to R3 and R5 are as hereinbefore defined and R„ denotes an R7- (n-C^-alkyl) -phenyl group, wherein R7 denotes an amino, C^.g-alkylamino, di- (C^.g-alkyl) -amino, phenylamino, N-phenyl-C1.3-alkyl-amino, phenyl -C1_2- alkyl -amino, N- (C^-alkyl) -phenyl-C1.3-alkylamino or di-(phenyl-Ca.3-alkyl) -amino group, or a phenyl group substituted by the group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12, p and R13 are as hereinbefore defined, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. Particularly preferred compounds of general formula I are those wherein X denotes an oxygen atom, R-L denotes a hydrogen atom, R2 denotes a carboxy group, a straight-chain or branched C1.4-alkoxycarbonyl group or a phenoxycarbonyl group, a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, carboxy, C1.3-alkoxycarbonyl, aminocarbonyl, C1.3-alkylaminocarbonyl or di- (C^-alkyl) -aminocarbonyl group, a straight-chain or branched C2.3-alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a hydroxy, C10-alkoxy, amino, C^-alkylamino or di- (C1.3-alkyl) -amino group, an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (Ci^-alkyl) -CVj-alkylaminocarbonyl-phenyl group, it may also denote a di- (C^-alkyl)-aminocarbonyl group, R3 denotes a C^-alkyl group or a phenyl group which may be substituted by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C1_3-alkyl, hydroxy or C1_3-alkoxy group, R4 denotes a Cs_6-cycloalkyl group, wherein the methylene group in position 4 of the cyclohexyl group may be substituted by an amino, C^-alkylamino or di- (C^-alkyl)-amino group or replaced by an -NH or -N(C1.3-alkyl) group, a phenyl group, a phenyl group disubstituted by C^-alkyl, C1_3-alkoxy or nitro groups, wherein the substituents may be identical or different, or a phenyl group substituted by the group R6, which may additionally be substituted by a fluorine, chlorine or bromine atom or by an amino or nitro group, wherein R6 denotes a fluorine, chlorine or bromine atom, a C^-alkyl, C1.3-alkoxy, nitro, amino or C5.6-cycloalkyl group, a pyrrolyl, pyrazolyl, imidazolyl, triazolyl or tetrazolyl group bound via a carbon atom, wherein the abovementioned heteroaromatic groups in the carbon skeleton may be substituted by a C1.3-alkyl group or a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl or phenyl-Cj.-j-alkyl group, the group of formula a carboxy, C^-alkoxycarbonyl, phenyl-C^-alkylamino-carbonyl or C5.7-cycloalkyl-carbonyl group, a 5 or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an -NH or -N (C^-alkyl) group, an unbranched C^-alkyl group terminally substituted by the group R7, wherein R7 denotes a C5.7-cycloalkyl group, wherein in a 5 or 6-membered cycloalkyl group a -(CH2)2 group may be replaced by a -CO-NH group, a -(CH2)3 group may be replaced by an -NH-CO-NH- or a -(CH2)4 group may be replaced by an -NH-CO-NH-CO group, whilst in each case a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl group, a phenyl or pyridinyl group or a pyrrolyl, pyrazolyl, imidazolyl or triazolyl group bound via a carbon or nitrogen atom, wherein the abovementioned heteroaromatic groups in the carbon skeleton may be substituted by a C^-alkyl group or a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl group, a hydroxy or C^-alkoxy group, an amino, C^g-alkylamino, di- (C^g-alkyl) -amino, phenylamino, N-phenyl-C^-alkylamino, phenyl-G^-alkylamino or N- (C^-alkyl) -phenyl-C1_3-alkylamino group, a co-hydroxy-C2_3-alkyl-amino, N- (C^-j-alkyl) -co-hydroxy~C2_3-alkylamino, di- (co-hydroxy-C2.3-alkyl) -amino or di- (co- (C^-alkoxy) -C2_3-alkyl) -amino group, a C1.3-alkylcarbonylamino-C2.3-alkyl-amino or C1.3-alkylcarbonylamino-C2.3-alkyl-N- (C^-alkyl) -amino group, a C^-alkylsulphonylamino, N- (C^-alky!) -C1.3-alkylsulphonylamino, C-^-alkylsulphonylamino--C2.3-alkylamino or C^-alkylsulphonylamino--C2_3-alkyl-N- (C1.3-alkyl) -amino group, a hydroxycarbonyl-C1_3-alkylamino or N- (C-^-alkyl) -hydroxycarbonyl-C-L.-j-alkyl-amino group, a guanidino group wherein a hydrogen atom may be replaced by a C^-alkyl group, a group of formula -N(R8)-CO-(CH2)n-R9 (ID, wherein R8 denotes a hydrogen atom or a C^-alkyl group, n denotes one of the numbers 0, 1, 2 or 3 and R9 denotes an amino, C^-alkylamino, di- (C^3-alkyl) -amino or C^-alkoxy group, a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH, -N (C^-alkyl) or -N(C1.3-alkyl-carbonyl) group, or, if n denotes one of the numbers 1, 2 or 3, R9 may also denote a hydrogen atom, a group of formula -N(R10)-(CH2)m-(CO)0-R11 (III), wherein R10 denotes a hydrogen atom or a C^-alkyl group, m denotes one of the numbers 1, 2 or 3, o denotes the number 1 or, if m is one of the numbers 2 or 3, o may also denote the number 0 and RX1 denotes an amino, C1.3-alkylamino, di- (C^-alkyl) -amino, C^-alkoxy or methoxy-C1.3-alkoxy group or a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH, -N(C1.3-alkyl) or -N (C1.3-alkyl-carbonyl) group, an azetidino, pyrrolidino, piperidino, 2, 6-dimethyl-piperidino, 3,5-dimethyl-piperidino or azepino group, wherein the methylene group in position 3 of the pyrrolidino group may be substituted by a hydroxy group, the methylene group in position 4 of the piperidino group may be substituted by a hydroxy, hydroxy-C^3-alkyl or C^-alkoxy group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N (C^-alkyl) , -N (C^-alkyl-carbonyl), -N(benzoyl) or -Ntphenyl-C^-alkyl-carbonyl) group, wherein a methylene group linked to an imino-nitrogen atom of the pyrrolidino, piperidino or piperazino group may be replaced by a carbonyl group, or R6 denotes a straight-chain C^-alkyl group which is terminally substituted by a carboxy or C^-alkoxy-carbonyl group, a group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12 denotes a hydrogen atom, a C^-alkyl or phenyl-Cx.3-alkyl group, p denotes one of the numbers 0, 1 or 2 and R13 denotes an amino, C^-alkylamino, di-(C1.4-alkyl)-amino, benzylamino, N-(C^-alkyl)-benzylamino, (^..j-alkoxy-C^-alkylamino, N- (C^-alkyl) - C1_3-alkoxy-C1.3-alkylamino/ di- (2-methoxy-ethyl) -amino, di- {co-hydroxy-C2_3-alkyl) -amino or aminocarbonyl-methyl-N-(methyl)-amino group, a pyrrolyl, pyrazolyl or imidazolyl group bound via a nitrogen atom and optionally substituted by a C^-alkyl group, a pyrrolidino, piperidino, morpholino, thiomorpholino or a piperazino group optionally substituted in the 4 position by a C^-alkyl, phenyl - C^ - alkyl, C^-alkylcarbonyl or C^-alkoxycarbonyl group or, if n denotes the number 1 or 2, it may also denote a hydrogen atom, a group of formula -N(R14)-(CH2)q-(CO)r-R15 (V), wherein R14 denotes a hydrogen atom, a C^-alkyl, C^-alkyl-carbonyl, phenylcarbonyl, phenyl-C^-alkylcarbonyl, furyl-carbonyl, pyridinyl-carbonyl, furyl-C^-alkylcarbonyl, pyridinyl-C^j-alkylcarbonyl, C^-alkylsulphonyl, phenyl sulphonyl or phenyl -Cx_3- alkyl sulphonyl group, q denotes one of the numbers 1, 2 or 3, r denotes the number 1 or, if q is one of the numbers 2 or 3, it may also denote the number 0 and R15 denotes an amino, C^-alkylamino, di- (C^-alkyl) -amino, phenylamino, N- (C^-alkyl) -phenylamino, benzylamino or N-(C^-alkyl)-benzylamino group,or a group of formula -N(R16)-S02-Ri7 (VI), wherein R1S denotes a hydrogen atom or a C^-alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino or N- (C^-alkyl) -trifluoromethyl-carbonyl-amino group and R17 denotes a C^-alkyl group, wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under R6 may be substituted by a fluorine, chlorine or bromine atom, by a methyl," trifluoromethyl, methoxy, nitro or cyano group and R5 denotes a hydrogen atom, wherein a hydrogen atom bound to a nitrogen atom in the abovementioned groups may be replaced by an acetyl or tert.butoxycarbonyl group, the carboxy groups contained in the abovementioned groups may also be present in the form of the tert.butoxycarbonyl precursor group and the saturated alkyl and alkoxy moieties contained in the abovementioned groups, which contain more than 2 carbon atoms, may be straight-chain or branched, unless otherwise stated, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. One subgroup of particularly preferred compounds of general formula I deserving special mention comprises those wherein X, Rx, R3 and R5 are as hereinbefore defined, R2 denotes a straight-chain or branched C^-alkoxycarbonyl group or a phenoxycarbonyl group, a straight-chain or"branched C^-alkoxycarbonyl group, which is terminally substituted in the alkyl moiety by a phenyl-carboxy, C1.3-alkoxycarbonyl, aminocarbonyl, C^-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group, or a straight-chain or branched C2_3-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a hydroxy, C^-alkoxy, amino, C-^-alkylamino or di- (C^-alkyl) -amino group, and R4 denotes an R7- (n-C^-alkyl) -phenyl group, wherein R7 denotes an amino, C^.j-alkylamino, di- (C^-alkyl) -amino, co - hydroxy- C2_3- alkyl -amino, N- (C1„3-alkyl) -co-hydroxy-C2_3-alkyl-amino, di- (co-hydroxy-C2.3-alkyl) -amino or di- (co- (C1.3-alkoxy) -C2.3-alkyl) -amino group, or a phenyl group substituted by the group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12, p and R13 are as hereinbefore defined, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. A second subgroup of particularly preferred compounds of general formula I deserving special mention comprises those wherein X, R1 R3 and Rs are as hereinbefore defined, R2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1-3-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (C1-3-alkyl) -C1-3-alkylaminocarbonyl-phenyl group, R2 may also denote a di- (C1-3-alkyl)-aminocarbonyl group and R4 denotes a R7- (n-C1-3-alkyl) -phenyl group, wherein R7 denotes an amino, C1-3-alkylamino, di- (C1-4-alkyl) -amino, co-hydroxy-C2-3-alkyl-amino, N- (C1-3-alkyl) -co-hydroxy--C2-3-alkyl-amino, di- (to-hydroxy-C2-3-alkyl) -amino or di- (03- (C1-3-alkoxy) -C2-3-alkyl) -amino group, or a phenyl group substituted by the group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12, p and R13 are as hereinbefore defined, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. Most particularly preferred compounds of general formula I are those wherein X denotes an oxygen atom, R.x and R5 each denote a hydrogen atom, R2 denotes a methoxycarbonyl, ethoxycarbonyl or aminocarbonyl group, R3 denotes a phenyl group and R4 denotes a phenyl group monosubstituted by the group R6, wherein R6 denotes an N-methyl-imidazol-2-yl group, an unbranched C^-alkyl group which is terminally substituted by a C^-alkylamino, di-(C^-alkyl)-amino, piperidino or 2,6-dimethyl-piperidino group, a group of formula -N(R12)-CO-(CH2)p-Ri3 (IV), wherein R12 denotes a C-^-alkyl group, p denotes one of the numbers 1 or 2 and R13 denotes a di- (C^-alkyl) -amino group, or a group of formula -N(R14)-(CH2)q-(CO)r-R15 (V), wherein R14 denotes a C1.3-alkyl-carbonyl or C^-alkylsulphonyl group, q denotes one of the numbers 1, 2 or 3, r denotes the number 1 or, if q is one of the numbers 2 or 3, r may also denote the number 0 and R1S denotes a di- (C^-alkyl) -amino group, wherein the saturated alkyl moieties contained in the abovementioned groups which contain more than 2 carbon atoms may be straight-chain or branched, unless otherwise stated, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. A subgroup of most particularly preferred compounds of general formula I deserving special mention comprises those wherein X, R^ R3 and R5 are as hereinbefore defined, R2 denotes a methoxycarbonyl or ethoxycarbonyl group and R4 denotes a di-(C^-alkyl) - amino-C^-alkylphenyl group or a phenyl group substituted by the group of formula -N(R12)-CO-(CH2)p-Ri3 (IV) wherein R12l p and R13 are as hereinbefore defined, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof. The following are mentioned as examples of particularly preferred compounds: (a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone, (b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6-carbamoyl-2-indolinone, (c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone, (d) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone, (e) 3-Z-[l-(4-((2,6-dimethyl-piperidin-1-yl)-methyl)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone, (f) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-ani¬lino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (g) 3-Z- [1- (4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-ani-lino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (h) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (i) 3-Z-[l-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (j) 3-Z-[1-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (k) 3-Z-[1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone, (1) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone, (m) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (n) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (o) 3-Z-[l-(4-(N-(3dimethylamino-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (p) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone, (q) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (r) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-ani¬lino) -1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone and (s) 3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone the tautomers, the mixtures and the salts thereof. Another subgroup of compounds of general formula I comprises those wherein X denotes an oxygen or sulphur atom, RL denotes a hydrogen atom or a prodrug group such as a C^-alkoxycarbonyl or C2.4-alkanoyl group, R2 denotes a carboxy group, a straight-chain or branched C^g-alkoxycarbonyl group, a C5_7-cycloalkoxycarbonyl or phenyl-C1.3-alkoxycarbonyl group, an aminocarbonyl or C^-alkylamihocarbonyl group or, if R4 does not denote an aminosulphonyl-phenyl or N- (C^-alkyl) -Cj^.j-alkylaminocarbonyl-phenyl group, a di- (C^-alkyl)-aminocarbonyl group, R3 denotes a hydrogen atom, a C^-alkyl, C3.7-cycloalkyl, trifluoromethyl or heteroaryl group, a phenyl or naphthyl group, a phenyl or naphthyl group mono-or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trif luoromethyl, C^-alkyl or C^-alkoxy group, whilst in the event of disubstitution the substituents may be identical or different and wherein the abovementioned unsubstituted as well as the mono- and disubstituted phenyl and naphthyl groups may additionally be substituted by a hydroxy, hydroxy-C^-alkyl or C^-alkoxy-C^-alkyl group, by a cyano, carboxy, carboxy-C^-alkyl, C-^-alkoxycarbonyl, aminocarbonyl, C^-alkylamino-carbonyl or di- (C^-alkyl)-aminocarbonyl group, by a nitro group, by an amino, C1_3-alkylamino, di- (C^-alkyl) -amino or amino-C^-alky 1 group, by a Cj^-alkylcarbonylamino, N- (C^-alkyl) -C^-alkyl- carbonyl amino, C1.3-alkylcarbonylamino-C1.3-alkyl, N- (C^-alkyl) -C-L.-j-alkylcarbonylamino-C^-alkyl, Cx.3-alkyl- sulphonylamino, C1.3-alkylsulphonylamino-C1.3-alkyl, N- (C1.3-alkyl) -C1.3-alkylsulphonylamino-C1.3-alkyl or aryl-C^-alkylsulphonylamino group, by a cycloalkylamino, cycloalkyleneimino, cyclo-alkyleneiminocarbonyl, cycloalkyleneimino-C1-3-alkyl, cycloalkyleneiminocairbonyl-C1-3-alkyl or cycloalkyleneiminosulphonyl-C1-3-alkyl group having 4 to 7 ring members in each case, whilst in each case the methylene group in position 4 of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH or -N(C1.3-alkyl) group, or by a heteroaryl or heteroaryl-C1.3-alkyl group, R4 denotes a C3.7-cycloalkyl group, whilst the methylene group in the 4 position of a 6- or 7 membered cycloalkyl group may be substituted by an amino, C^.j-alkylamino or di- (C^-alkyl) -amino group or replaced by an -NH or -N (C1.3-alkyl) group, or a phenyl group substituted by the group Rfi, which may additionally be substituted by a fluorine, chlorine, bromine or iodine atom, by a Cx.5-alkyl, trif luoromethyl, C^-j-alkoxy, carboxy, C1.3-alkoxycarbonyl, aminosulphonyl, nitro or cyano group, wherein R6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, a cyano, nitro, C^-alkyl, C3_7-cycloalkyl, trif luoromethyl, phenyl, tetrazolyl or heteroaryl group, a C1.3-alkoxy group optionally sunstituted by 1 to 3 fluorine atoms, a C1.3-alkoxy-C1.3-alkoxy, phenyl-C1.3-alkoxy, amino-C2.3-alkoxy, C1_3-alkylamino-C2_3-alkoxy, di- (C^-alkyl) -amino-C2.3-alkoxy, phenyl-C^-alkylamino- C2-3-alkoxy, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino-C1-3-alkoxy, C5-7-cycloalkyleneimino-C2-3-alkoxy or C1-3-alkylmercapto group, a carboxy, C1-4-alkoxycarbonyl, aminocarbonyl, C1-3-alkyl-amino-carbonyl, N- (C1-3-alkyl) -C1-3-alkylaminocarbonyl, phenyl-C1-3-alkylamino-carbonyl, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino-carbonyl, piperazinocarbonyl or N- (C1-3-alkyl)-piperazinocarbonyl group, a C1-3-alkylaminocarbonyl or N- (C1-3-alkyl) -C1-3-alkylaminocarbonyl group wherein an alkyl moiety is substituted by a carboxy or C1-3-alkoxycarbonyl group or is substituted in the 2 or 3 position by a di- (C1-3-alkyl)-amino, piperazino, N- (C1-3-alkyl)-piperazino or a 4- to 7-membered cycloalkyleneimino group, a 4- to 7-membered cycloalkyleneimino group, wherein a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or the cycloalkylene moiety may be fused to a phenyl ring or one or two hydrogen atoms may each be replaced by a C1-3-alkyl group and/or in each case the methylene group in the 4 position of a 6-or 7-membered cycloalkyleneimino group may be substituted by a carboxy, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di- (C1-3-alkyl) -aminocarbonyl, phenyl-C1-3-alkylamino or N-(C1-3-alkyl)-phenyl-C^-alkylamino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl), -N(phenyl), -N(C1-3-alkyl-carbonyl) or -N (benzoyl) group, a C1-4-alkyl group which may be substituted by a hydroxy or C1-3-alkoxy group, by an amino, C1-3-alkylamino, di- (C1-7-alkyl) -amino, di-N- (C1-3-alkyl) -amino-C2-3-alkylamino, tri-N,N,N" - (C1-3-alkyl) -amino-C2-3-alkylamino, phenylamino, N-phenyl-C1-3-alkyl-amino, phenyl-C1-3-alkylamino, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino or di-(phenyl-C1-3-alkyl)-amino group, by a C1-3-alkylcarbonylamino, N-(C1-3-alkyl)-C1-3-alkylcarbonylamino, C1-3-alkoxycarbonyl-C1-3-alkyl amino or N- (C1-3-alkyl) -C1-3-alkoxycarbonyl-C1-3-alkylamino group, by a C4-7-cycloalkylamino, C1-3-cycloalkyl-C1-3-alkylamino or C4-7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond and wherein the abovementioned groups may each additionally be substituted at the amino-nitrogen atom by a C1-3-alkyl group wherein some or all of the hydrogen atoms are replaced by fluorine atoms, by a C5-7-cycloalkyl, C2-4-alkenyl or Cl-4-alkyl group, by a 4- to 7-membered cycloalkyleneimino group, wherein a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C1-3-alkyl, C1-3-alkoxy or amino group or one or two hydrogen atoms may each be replaced by a C1-3-alkyl, C5-7-cycloalkyl or phenyl group and/or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, carboxy, C1-4-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di- (C1-3-alkyl) -aminocarbonyl, phenyl-C1-3-alkylamino or N- (C1-3-alkyD"-phenyl-C1-3-alkylamino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N (C1-3-alkyl), -N(phenyl), -N(C1-3-alkyl-carbonyl) or -N(benzoyl) group, by a carboxy, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl or di- (C1-3-alkyl) -aminocarbonyl group or by a 4- to 7-membered cycloalkyleneiminocarbonyl group, an amino, pyrrolidino, piperidino, morpholino, benzoylamino or N- (C1-3-alkyl)-benzoylamino group, an N- (C1-3-alkyl) -C2-4-alkanoylamino group which is additionally substituted in the alkyl moiety by a carboxy or C1-3-alkoxycarbonyl group, a group of formula -N(R8)-CO-(CH2)n-R9 (II), wherein R8 denotes a hydrogen atom or a C1-3-alkyl group, n denotes one of the numbers 0, 1, 2 or 3 and R9 denotes an amino, C1-4-alkylamino, phenylamino, N- (C1-4-alkyl) -phenylamino, benzylamino, N~ (C1-4-alkyl) -benzylamino or di- (C1-4-alkyl) -amino group, a 4- to 7-membered cycloalkyleneimino group, whilst in each case the methylene group in the 4 position of a 6- or 7- membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl) , -N (phenyl) , -N(C1-3-alkyl-carbonyl) or -N(benzoyl) group, or, if n denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom, a group of formula -N(R10)-(CH2)m-(C0)o-R11 (III), wherein R10 denotes a hydrogen atom, a C1-3-alkyl group, a C1-3-alkylcarbonyl, arylcarbonyl, phenyl - C^ - alkylcarbonyl, C1-3-alkylsulphonyl, arylsulphonyl or phenyl-C1-3-alkylsulphonyl group, m denotes one of the numbers 1, 2, 3 or 4, o denotes one of the numbers 0 or 1 and R11 denotes an amino, C1-3-alkylamino, phenylamino, N- (C1-3-alkyl)-phenylamino, benzylamino, N- (C1-4-alkyl) -benzylamino or di- (C1-4-alkyl) -amino group, a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl) , -N(phenyl) , -N (C1-3-alkyl-carbonyl) or -N(benzoyl) group, a C1-3-alkoxy group or a di- (C1-4-alkyl) -amino-C1-3-alkylamino group optionally substituted in the 1 position by a C1-3-alkyl group, or an N-(C1-3-alkyl)-C1-3-alkylsulphonylamino or N- (C1-3-alkyl)-phenylsulphonylamino group wherein the alkyl moiety is additionally substituted by a cyano or carboxy group, wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under R6 may be mono- or disubstituted by fluorine, chlorine, bromine or iodine " atoms, by C1-5-alkyl, trifluoromethyl, C1-3-alkoxy, carboxy, C1-3-alkoxycarbonyl, aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group, and R5 denotes a hydrogen atom or a C1-3-alkyl group, wherein by an aryl group is meant a phenyl or naphthyl group optionally mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C1-3-alkyl or C1-3-alkoxy group and by a heteroaryl group is meant a monocyclic 5- or 6-membered heteroaryl group optionally substituted by a C1-3-alkyl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted by a C1-3-alkyl group, an oxygen or sulphur atom or an imino group optionally substituted by a C1-3-alkyl group and an oxygen or sulphur -atom or one or two nitrogen atoms, and moreover a phenyl ring may be fused to the abovementioned monocyclic heterocyclic groups via two adjacent carbon atoms, the saturated alkyl and alkoxy moieties present in the groups defined above which contain more than 2 carbon atoms also include the branched isomers thereof such as, for example, the isopropyl, tert.butyl or isobutyl group, unless otherwise stated, and additionally any carboxy, amino or imino group present may be substituted by a group which can be cleaved in vivo, the isomers and the salts thereof. According to the invention the new compounds are obtained, for example, by the following methods known in principle from the literature: a. reacting a compound of general formula (VII), wherein X and R3 are as hereinbefore defined, R2" has the meanings given for R2 hereinbefore, Rie denotes a hydrogen atom or a protecting group for the nitrogen atom of the lactam group, wherein one of the groups R2" and R18 may also denote a bond to a solid phase optionally formed via a spacer and the other one of the groups R2" and R18 has the abovementioned meanings, and Z1 denotes a halogen atom, a hydroxy, alkoxy or aryl-alkoxy group, e.g. a chlorine or bromine atom, a methoxy, ethoxy or benzyloxy group, with an amine of general formula wherein R4 and R5 are as hereinbefore defined, and if necessary subsequently cleaving any protecting group used for the nitrogen atom of the lactam group or cleaving from a solid phase. The protecting group for the nitrogen atom of the lactam group may be, for example, an acetyl, benzoyl, ethoxycarbonyl, tert.butyloxycarbonyl or benzyloxycarbonyl group and the solid phase may be a resin such as a 4-(2",4"-dimethoxyphenylaminomethyl)-phenoxy resin, the bond preferably being formed via the amino group, or a p-benzyloxybenzyl alcohol resin, wherein the bond is conveniently formed via an intermediate member such as a 2,5-dimethoxy-4-hydroxy-benzyl derivative. The reaction is conveniently carried out in a solvent such as dimethylformamide, toluene, acetonitrile, tetrahydrofuran, dimethylsulphoxide, methylene chloride or mixtures thereof, optionally in the presence of an inert base such as triethylamine, N-ethyl-diisopropylamine or sodium hydrogen carbonate at temperatures between 20 and 175°C, whilst any protecting group used can be cleaved at the same time by transamidation. If 21 in a compound of general formula VII denotes a halogen atom, the reaction is preferably carried out in the presence of an inert base at temperatures of between 20 and 120°C. If Zx in a compound of general formula VII denotes a hydroxy, alkoxy or arylalkoxy group, the reaction is preferably carried out at temperatures between 2 0 and 200°C. If a protecting group used subsequently has to be cleaved, this is conveniently done either hydrolytically in an aqueous or alcoholic solvent, e.g. in methanol/water, ethanol/water, isopropanol/water, tetrahydrofuran/water, dioxan/water, dimethylformamide/water, methanol or ethanol in the presence of an alkali metal base such as lithium hydroxide, sodium hydroxide or potassium hydroxide at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50°C, or advantageously by transamidation with an organic base such as ammonia, butylamine, dimethylamine or piperidine in a solvent such as methanol, ethanol, dimethylformamide and the mixtures thereof or in an excess of the amine used, at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50°C. Cleaving from any solid phase used is preferably carried out using trifluoroacetic acid and water at temperatures between 0 and 35°C, preferably at ambient temperature. b. In order to prepare a compound of general formula I wherein R2 has the meanings given hereinbefore, with the exception of the carboxy group: reacting a compound of general formula (IX) wherein R± and R3 to R5 are as hereinbefore defined, or the reactive derivatives thereof, with a compound of general formula (X) , wherein R19 denotes a C^-alkanol, a C4.7-cycloalkanol or an aromatic alcohol, a C^.g-alkanol which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C^-alkoxy-carbonyl, aminocarbonyl, C^-alkylamino-carbonyl or di- (C^-alkyl) -aminocarbonyl group, a C2_6-alkanol which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, Cx^3-alkoxy, amino, C1_3-alkylamino or di- (C^-alkyl) -amino group, an amino or methylamino group, an ethylamino group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1_3-alkoxy group or a di- (C^-alkyl) -amino group. The esterification or amidation is preferably carried out in a solvent such as methylene chloride, diethylether, tetrahydrofuran, toluene, dioxan, acetonitrile, dimethylsulphoxide or dimethylformamide, optionally in the presence of an inorganic or a tertiary organic base, preferably at temperatures between 20°C and the boiling temperature of the solvent used. The reaction with a corresponding acid is preferably carried out in the presence of a dehydrating agent, e.g. in the presence of isobutyl chloroformate, tetraethyl orthocarbonate, trimethyl orthoacetate, 2,2-dimethoxypropane, tetramethoxysilane, thionylchloride, trimethylchlorosilane, phosphorus trichloride, phosphorus pentoxide, N,N"-dicyclohexylcarbodiimide, N,N"-dicyclohexyl-carbodiimide/N-hydroxysuccinimide, N,N"-dicyclohexyl-carbodiimide/l-hydroxy-benzotriazole, 2-(lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-tetrafluoroborate, 2-(1H-benzotriazol-l-yl)-1,1,3,3-tetramethyluronium-tetraf luoroborate/l-hydroxy-benzotriazole, N,N"-carbonyldiimidazole or triphenylphosphine/carbon tetrachloride, and optionally with the addition of a base such as pyridine, 4-dimethylaminopyridine, N-methyl-morpholine or triethylamine, conveniently at temperatures between 0 and 150°C, preferably at temperatures between 0 and 100°C, and the acylation with a corresponding reactive compound such as an anhydride, ester, imidazolide or halide thereof, is optionally carried out in the presence of a tertiary organic base such as triethylamine, N-ethyl-diisopropylamine or N-methyl-morpholine at temperatures between 0 and 150°C, preferably at temperatures between 50 and 100°C. c. In order to prepare a compound of general formula I, wherein R4 denotes a C1-4-alkyl group substituted by the group R7, wherein R7 denotes an amino, C1-7-alkylamino, di-(C1-7-alkyl)-amino, phenylamino, N-phenyl-C1-3-alkyl-amino, phenyl-C1-3-alkyl-amino, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino or di- (phenyl-C1-3-alkyl) -amino group, a co-hydroxy-C2_3-alkyl-amino, N- (C1-3-alkyl) -co-hydroxy-C2-3-alkyl-amino, di- (co~ hydroxy-C2-3-alkyl) -amino, di- (co- (C1-3-alkoxy) -C2-3-alkyl) -amino or N-(dioxolan-2-yl)-C^-alkyl-amino group, a C1.3-alkylcarbonylamino-C2_3-alkyl-amino or C1.3-alkylcarbonylamino-C2.3-alkyl-N- (C1.3-alkyl) -amino group, a C1.3-alkylsulphonylamino, N- (C1.3-alkyl) - C^-alkyl sulphonylamino, C^3 -alkyl sulphonyl amino -C2.3-alkyl- amino or C1_3-alkylsulphonylamino-C2.3-alkyl-N- (C^-alkyl) -amino group, a group of formula -N(R10) - (CH2)ra- (C0)o-Rn (III) , wherein R10 denotes a hydrogen atom, a C^-alky! group, a C^-alkylcarbonyl, arylcarbonyl, phenyl-C^-alkyl-carbonyl, C^- alkyl sulphonyl, arylsulphonyl or phenyl-C1.3-alkylsulphonyl group, m denotes one of the numbers 1, 2, 3 or 4, o denotes the number 1 and R1X denotes an amino, C^-alkylamino, di- (C^-alkyl)-amino, phenylamino, N-(C^-alkyl)-phenylamino, benzylamino, N- (C^-alkyl) -benzylamino, C^-alkoxy or C^-alkoxy-C^-alkoxy group, a di- (Cx.4-alkyl) -amino-C^- alkylamino group optionally substituted in the 1 position by a C1-3-alkyl group, or a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl) , -N(phenyl), -N (C1-3-alkyl-carbonyl) or -N(benzoyl) group, a C4-7-cycloalkylamino, C4-7-cycloalkyl-C1-3-alkylamino or C4_7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond and wherein the abovementioned groups may each additionally be substituted at the amino-nitrogen atom by a Cs_7-cycloalkyl, C2_4-alkenyl or C^-alkyl group, or a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridine pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C1-3-alkyl, C1-3-alkoxy or amino group, and/or one or two hydrogen atoms may each be replaced by a C1-3-alkyl, C1-3-cycloalkyl or phenyl group and/or the methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C1-3-alkyl, C1-3-alkoxy or C1-3-alkoxy-C1-3-alkyl group, in each case the methylene group in the 3 or 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C1-3-alkyl, C1-3-alkoxy, C1-3-alkoxy-C1-3-alkyl, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di- (C1-3-alkyl)-aminocarbonyl, phenyl-C1-3-alkylamino or N- (C1-3-alkyl)-phenyl-C1-3-alkylamino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl-) , -N(phenyl), -N(phenyl-C1-3-alkyl-) , -N(C1-3-alkyl-carbonyl-) , -N(C1-3-alkoxy-carbonyl-), -N(benzoyl-) or -N (phenyl - C1-3 - alkyl - carbonyl - ) group, wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5-to 7-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group: reacting a compound of general formula (XI), wherein R3, R5 and X are as hereinbefore defined, R, has the meanings given for R2 hereinbefore, R1B denotes a hydrogen atom or a protecting group for-the nitrogen atom of the lactam group, wherein one of the groups R2" and R18 may also denote a bond to a solid phase optionallyformed via a spacer and the other one of the groups R2" and R18 has the abovementioned meanings, A denotes a C1-4-alkyl group and Z2 denotes a leaving group, for example an alkyl or arylsulphonyloxy group such as the methylsulphonyloxy, ethylsulphonyloxy, p-toluenesulphonyloxy or trifluoromethanesulphonyloxy group, with an amine of general formula H R7 (XII) , wherein R7, has the meanings given for R7 hereinbefore, and subsequently, if necessary, cleaving any protecting group used for the nitrogen atom of the lactam group, or cleaving from a solid phase. The reaction is conveniently carried out in a solvent such as methylene chloride, tetrahydrofuran, 1,4-dioxan, toluene, acetonitrile, dimethylsulphoxide, dimethylformamide, dimethyl-acetamide, N-methylpyrrolidone or the mixtures thereof, optionally with the addition of water as a co-solvent and/or with the addition of an inert auxiliary base, e.g. sodium hydrogen carbonate, pyridine, 2,4,6-trimethylpyridine, quinoline, triethylamine, N-ethyldiisopropylamine, N-ethyl-dicyclohexylamine, 1,4-diazabicyclo[2,2,2]octane or 1,8-diazabicyclo[5,4,0]undec-7-ene, at temperatures between -50°C and +100°C, preferably between -10°C and +50°C, while any protecting group, used may be cleaved at the same time by transamidation. If any protecting group used for the nitrogen atom of the lactam group has to be removed or if the compound has to be cleaved from a solid phase this is carried out as described under method (a) above.If according to the invention a compound of general formula I is obtained which contains an alkoxycarbonyl group, this may be converted by hydrolysis into a corresponding carboxy compound, or if a compound of general formula I is obtained which contains an amino or alkylamino group, this may be converted by reductive alkylation into a corresponding alkylamino or dialkylamino compound, or if a compound of general formula I is obtained which contains an amino or alkylamino group, this may be converted by acylation or sulphonation into a corresponding acyl or sulphonyl compound, or if a compound of general formula I is obtained which contains a carboxy group, this may be converted by esterification or amidation into a corresponding ester or aminocarbonyl compound, or if a compound of general formula I is obtained which contains a cycloalkyleneimino group wherein a methylene group is replaced by a sulphur atom, this may be converted by oxidation into a corresponding sulphinyl or sulphonyl compound, or if a compound of general formula I is obtained which contains a nitro group, this may be converted by reduction into a corresponding amino compound, or if a compound of general formula I is obtained wherein R4 denotes a phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group, this may subsequently be converted, by reaction with a corresponding cyanate, iso-cyanate or carbamoyl halide, into a corresponding urea compound of general formula I, or if a compound of general formula I is obtained wherein R4 denotes a phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group, this may subsequently be converted, by reaction with a corresponding compound which transfers the amidino group or by reaction with a corresponding nitrile, into a corresponding guanidino compound of general formula I. The subsequent hydrolysis is preferably carried out in an aqueous solvent, e.g. in water, methanol/water, ethanol/water, isopropanol/water, tetrahydrofuran/water or dioxan/water, in . the presence of an acid such as trifluoroacetic acid, hydrochloric acid or sulphuric acid or in the presence of an alkali metal base such as lithium hydroxide, sodium hydroxide or potassium hydroxide at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50QC. The subsequent reductive alkylation is preferably carried out in a suitable solvent such as methanol, methanol/water, methanol/water/ammonia, ethanol, ether, tetrahydrofuran, dioxan or dimethylformamide, optionally with the addition of an acid such as hydrochloric acid in the presence of catalytically activated hydrogen, e.g. hydrogen in the presence of Raney nickel, platinum or palladium/charcoal, or in the presence of a metal hydride such as sodium borohydride, lithium borohydride, sodium cyanoborohydride or lithium aluminium hydride at temperatures between 0 and 100°C, preferably at temperatures between 20 and 80°C. The subsequent acylation or sulphonylation is preferably carried out with the corresponding free acid or a corresponding reactive compound such as the anhydride, ester, imidazolide or halide thereof, preferably in a solvent such as methylene chloride, diethylether, tetrahydrofuran, toluene, dioxan, acetonitrile, dimethylsulphoxide or dimethylformamide, optionally in the presence of an inorganic or tertiary organic base at temperatures between -20 and 200°C, preferably at temperatures between 20°C and boiling temperature of the solvent used. The reaction with the free acid may optionally be carried out in the presence of an acid-activating agent or a dehydrating agent, e.g. in the presence of isobutyl chloroformate, tetraethyl orthocarbonate, trimethyl orthoacetate, 2,2-dimethoxypropane, tetramethoxysilane, thionyl chloride, trimethylchlorosilane, phosphorus trichloride, phosphorus pentoxide, N,N"-dicyclohexyl-carbodiimide, N,N"-dicyclohexylcarbodiimide/N-hydroxysuccinimide, N,N"-dicyclohexylcarbodiimide/1-hydroxy-benzotriazole, 2-(lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-tetrafluoroborate, 2-(lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-tetrafluoroborate/1-hydroxy-benzotriazole, N,N"-carbonyldiimidazole or triphenylphosphine/carbon tetrachloride, and optionally with the addition of a base such as pyridine, 4-dimethylamino-pyridine, N-methyl-morpholine or triethylamine, conveniently at temperatures between 0 and 150°C, preferably at temperatures between 0 and 100°C. The reaction with a corresponding reactive compound may optionally be carried out in the presence of a tertiary organic base such as triethylamine, N-ethyl-diisopropylamine, N-methyl-morpholine or pyridine or by using an anhydride in the presence of the corresponding acid at temperatures between 0 and 150°C, preferably at temperatures between 50 and 100°C. The subsequent esterification or amidation is conveniently carried out by reacting a corresponding reactive carboxylic acid derivative with a corresponding alcohol or amine as described hereinbefore. The subsequent oxidation of the sulphur atom is preferably carried out in a solvent or mixture of solvents, e.g. in water, water/pyridine, acetone, methylene chloride, acetic sodium periodate or potassium permanganate in acetic acid, water/sulphuric acid or in acetone at 0 to 20°C. The subsequent reduction of a nitro group is preferably carried out by hydrogenolysis, e.g. with hydrogen in the presence of a catalyst such as palladium/charcoal or Raney nickel in a solvent such as methanol, ethanol, ethyl acetate, dimethylformamide, dimethylformamide/acetone or glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid or glacial acetic acid at temperatures of between 0 and 50°C, but preferably at ambient temperature, and at a hydrogen pressure of 1 to 7 bar, but preferably 3 to 5 bar. The subsequent preparation of a corresponding urea compound of general formula I is conveniently carried out with an inorganic cyanate or a corresponding isocyanate or carbamoylchloride, preferably in a solvent such as dimethylformamide and optionally in the presence of a tertiary organic base such as triethylamine at temperatures between 0 and 50°C, preferably at ambient. The subsequent preparation of a corresponding guanidino compound of general formula I is conveniently carried out by reacting with a compound which transfers the amidino group such as 3,5-dimethylpyrazole-l-carboxylic acid amidine, preferably in a solvent such as dimethylformamide and optionally in the presence of a tertiary organic base such as triethylamine at temperatures of between 0 and 50°C, preferably at ambient temperature. In the reactions described hereinbefore, any reactive groups present such as carboxy, hydroxy, amino, alkylamino or imino groups may be protected during the reaction by conventional protecting groups which are cleaved again after the reaction. For example, a protecting group for a carboxyl group may be a trimethylsilyl, methyl, ethyl, tert.butyl, benzyl or tetrahydropyranyl group and protecting groups for a hydroxy, amino, alkylamino or imino group may be an acetyl, trifluoroacetyl, benzoyl, ethoxycarbonyl, tert.butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl or 2,4-dimethoxybenzyl group and additionally, for the amino group, a phthalyl group. Any protecting group used is optionally subsequently cleaved for example by hydrolysis in an aqueous solvent, e.g. in water, isopropanol/water, tetrahydrofuran/water or dioxan/water, in the presence of a acid such as trifluoroacetic acid, hydrochloric acid or sulphuric acid or in the presence of an alkali metal base such as lithium hydroxide, sodium hydroxide or potassium hydroxide, at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50°C. However, a benzyl, methoxybenzyl or benzyloxycarbonyl group is cleaved, for example, hydrogenolytically, e.g. with hydrogen in the presence of a catalyst such as palladium/charcoal in a solvent such as methanol, ethanol, ethyl acetate, dimethylformamide, dimethylformamide/acetone or glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid or glacial acetic acid at temperatures between 0 and 50°C, but preferably at ambient temperature, and at a hydrogen pressure of 1 to 7 bar, but preferably 3 to 5 bar. A methoxybenzyl group may also be cleaved in the presence of an oxidising agent such as cerium(IV)ammonium nitrate in a solvent such as methylene chloride, acetonitrile or acetonitrile/water at temperatures of between 0 and 50°C, but preferably at ambient temperature. A 2,4-dimethoxybenzyl group, however, is preferably cleaved in trifluoroacetic acid in the presence of anisole. A tert.butyl or tert.butyloxycarbonyl group is preferably cleaved by treating with an acid such as trifluoroacetic acid or hydrochloric aci£, optionally using a solvent such as methylene chloride, dioxan, ethyl acetate or ether. A phthalyl group is preferably cleaved in the presence of hydrazine or a primary amine such as methylamine, ethylamine or n-butylamine in a solvent such as methanol, ethanol, isopropanol, toluene/water or dioxan at temperatures between 2 0 and 5 0°C. Moreover, chiral compounds of general formula I obtained may be resolved into their enantiomers and/or diastereomers. Thus, for example, the compounds of general formula I obtained which occur as racemates may be separated by methods known per se (cf. Allinger N. L. and Eliel E. L. in "Topics in Stereochemistry", Vol. 6, Wiley Interscience, 1971) into their optical antipodes and compounds of general formula I with at least 2 asymmetric carbon atoms may be resolved into their diastereomers on the basis of their physical-chemical differences using methods known per se, e.g. by chromatography and/or fractional crystallisation, and, if these compounds are obtained in racemic form, they may subsequently be resolved into the enantiomers as mentioned above. The enantiomers are preferably separated by column separation on chiral phases or by recrystallisation from an optically active solvent or by reacting with an optically active be obtained by methods known from the literature or may be obtained by the methods described hereinbefore and in the Examples. For example, the compounds of general formula VI are described in German Patent Application 198 24 922.5. Moreover, the compounds of general formula XI may be obtained from the compounds of general formula I wherein R4 denotes a C^-alkyl-phenyl group substituted in the alkyl moiety by a hydroxy group, for example, by reacting with alkyl- or arylsulphonyl chlorides. As already mentioned, the new compounds of general formula I wherein Rj_ denotes a hydrogen atom or a prodrug group have valuable pharmacological properties, particularly inhibitory effects on various kinases, especially on receptor-tyrosine kinases such as VEGFR2, PDGFRa, PDGFRp, FGFR1, FGFR3, EGFR, HER2, IGFIR and HGFR, as well as on complexes of CDK"s (Cyclin Dependent Kinases) such as CDK1, CDK2, CDK3, CDK4, CDK5, CDK6, CDK7, CDK8 and CDK9 with their specific cyclins (A, Bl, B2, C, Dl, D2, D3, E, F, Gl, G2, H, I and K) and on viral cyclin, on the proliferation of cultivated human cells, particularly endothelial cells, e.g. in angiogenesis, but also on the proliferation of other cells, particularly tumour cells. The biological properties of the new compounds were tested by the following standard procedure, as follows: Human umbilical endothelial cells (HUVEC) were cultivated in IMDM (Gibco BRL)," supplemented with 10 % foetal calf serum (FBS) (Sigma) , 50 pcM of fi-mercaptoethanol (Fluka) , standard antibiotics, 15 ^g/ml of endothelial cell growth factor (ECGS, Collaborative Biomedical Products) and 10 0 /xg/ml of heparin (Sigma) on gelatine-coated culture dishes (0.2 % gelatine, Sigma) at 37°C, under 5 % CO2 in a water-saturated atmosphere. In order to investigate the inhibitory activity of the compounds according to the invention the cells were starved for 16 hours, i.e. kept in culture medium without growth factors (ECGS + heparin). The cells were detached from the culture dishes using trypsin/EDTA and washed once in serum-containing medium. Then they were seeded out in amounts of 2.5 x 103 cells per well. The proliferation of the cells was stimulated with 5 ng/ml of VEGFi65 (vascular endothelial growth factor; H. Weich, GBF Braunschweig) and 10 /ig/ml of heparin. As a control, 6 wells in each dish were not stimulated. The compounds according to the invention were dissolved in 100% dimethylsulphoxide and added to the cultures in various dilutions in triplicate, the maximum dimethyl sulphoxide concentration being 0.3 %. The cells were incubated for 76 hours at 37°C, then for a further 16 hours 3H-thymidine (0.1 // Ci/well, Amersham) was added in order to determine the DNA synthesis. Then the radioactively labelled cells were immobilised on filter mats and the radioactivity incorporated was measured in a 6-counter. In order to determine the inhibitory activity of the compounds according to the invention the mean value of the non-stimulated cells was subtracted from the mean value of the factor-stimulated cells (in the presence or absence of the compounds according to the invention). The relative cell proliferation was calculated as a percentage of the control (HUVEC without inhibitor) and the concentration of active substance which inhibits the proliferation of the cells by 50 % (IC50) was determined. xhe test results of the following compounds (a) to (s) of general formula I are given by way of example: (a) 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone, (b) 3-Z- [ (1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6 -carbamoyl-2 -indolinone, (c) 3-Z- [1-(4-(piperidin-l-yl-methyl) -anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2-indolinone, (d) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone, (e) 3-Z- [1-(4- ( (2,6-dimethyl-piperidin-1-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (f) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (g) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino) -1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone, (h) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone, (i) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone, (j) 3-Z-[l-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (k) 3-Z- [1- (4-ethylaminomethyl-anilino) -1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone, (1) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (m) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (n) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (o) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (p) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone, (q) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (r) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl) -N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone and (s) 3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone. The following Table contains the results found: Compound IC50 [//m] (a) 0.04 (b) 0.35 (c) 0.01 (d) 0.02 (e) 0.05 (f) 0.01 (g) 0.003 (h) 0.01 (i) 0.03 (J) 0.02 (k) 0.03 (1) 0.1 (m) 0.02 (n) 0.02 (o) 0.01 (P) 0.02 (q) 0.02 (r) 0.01 (s) 0.04 In view of their inhibitory effect on the proliferation of cells, particularly endothelial cells and tumour cells, the compounds of general formula I are suitable for treating diseases in which the proliferation of cells, particularly endothelial cells, plays a part. Thus, for example, the proliferation of endothelial cells and the concomitant neovascularisation constitute a crucial stage in tumour progression (Folkman J. et al., Nature 339, 58-61, (1989); Hanahan D. and Folkman J., Cell 86, 353-365, (1996)). Furthermore, the proliferation of endothelial cells is also important in haemangiomas, in metastasisation, rheumatoid arthritis, psoriasis and ocular neovascularisation (Folkman J., Nature Med. 1, 27-31, (1995)). The therapeutic usefulness of inhibitors of endothelial cell proliferation was demonstrated in the animal model for example by O"Reilly et al. and Parangi et al. (O"Reilly M.S. et al. , Cell 8J., 277-285, (1997); Parangi S. et al. , Proc Natl Acad Sci USA .93., 2002-2007, (1996) ) . The compounds of general formula I, their tautomers, their stereoisomers or the physiologically acceptable salts thereof are thus suitable, for example, for treating tumours (e.g. plate epithelial carcinoma, astrocytoma, Kaposi"s sarcoma, glioblastoma, lung cancer, bladder cancer, carcinoma of the neck, melanoma, ovarian cancer, prostate cancer, breast cancer, small-cell lung cancer, glioma, colorectal carcinoma, urogenital cancer and gastrointestinal carcinoma as well as haematological cancers, such as multiple myeloma), psoriasis, arthritis (e.g. rheumatoid arthritis), haemangioma, angiofibroma, eye diseases (e.g. diabetic retinopathy), neovascular glaucoma, kidney diseases (e.g. glomerulonephritis), diabetic nephropathy, malignant nephrosclerosis, thrombic microangiopathic syndrome, transplant rejections and glomerulopathy, fibrotic diseases (e.g. cirrhosis of the liver), mesangial cell proliferative diseases, arteriosclerosis and damage to the nerve tissue and also for inhibiting the reocclusion of blood vessels after treatment with a balloon catheter, in vascular prosthetics or after the insertion of mechanical devices for keeping blood vessels open (e.g. stents), or other diseases in which cell proliferation or angiogenesis are involved. By reason of their biological properties the compounds according to the invention may be used on their own or in conjunction with other pharmacologically active compounds, for example in tumour therapy, in monotherapy or in conjunction with other anti-tumour therapeutic agents, for example in combination with topoisomerase inhibitors (e.g. etoposide), mitosis inhibitors (e.g. vinblastin, taxol), compounds which interact with nucleic acids (e.g. cis-platin, cyclophosphamide, adriamycin), hormone antagonists (e.g. tamoxifen), inhibitors of metabolic processes (e.g. 5-FU etc.), cytokines (e.g. interferons), kinase inhibitors, antibodies, or in conjunction with radiotherapy, etc. These combinations may be"administered either simultaneously or sequentially. For pharmaceutical use the compounds according to the invention are generally used for warm-blooded vertebrates, particularly humans, in doses of 0.01-100 mg/kg of body weight, preferably 0.1-20 mg/kg. For administration they are formulated with one or more conventional inert carriers and/or diluents, e.g. with corn starch, lactose, glucose, microcrystalline cellulose, magnesium stearate, polyvinylpyrrolidone, citric acid, tartaric acid, water, water/ethanol, water/glycerol, water/sorbitol, water/polyethylene glycol, propylene glycol, stearyl alcohol, carboxymethylcellulose or fatty substances such as hard fat or suitable mixtures thereof in conventional galenic preparations such as plain or coated tablets, capsules, powders, injectable solutions, ampoules, suspensions, solutions, sprays or suppositories.The Examples which follow are intended to illustrate the invention: Abbreviations used: FMOC = 9-fluorenylmethoxycarbonyl HOBt = 1-hydroxy^lH-benzotriazole TBTU = 0-benzotriazol-l-yl-N,N,N" ,N" -tetramethyluronium-tetrafluoroborate DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene Preparation of the starting compounds: Solid phase Example I 2.0 g of Rink resin (MBHA resin, made by Messrs Novabiochem) are left to swell in 30 ml of dimethylformamide. Then 40 ml of 30% piperidine in dimethylformamide are added and the mixture is shaken for 7 minutes to cleave the FMOC protecting group. The resin is then washed repeatedly with dimethylformamide. Then 0.4 g of 2-indolinone-6-carboxylic acid (prepared analogously to Langenbeck"et al., Justus Liebigs Ann. Chem. 4 99, 201-208 (1932)), 297 mg HOBt, 706 mg TBTU and 0.9 ml of N-ethyl-diisopropylamine in 30 ml of dimethylformamide are added and the mixture is shaken for 1 hour. Then the solution is suction filtered and the resin is washed five times with 3 0 ml of dimethylformamide and three times with 3 0 ml of methylene chloride. To dry it, nitrogen is blown through the resin. Yield: 1.9 g of charged resinSolid phase example II 1.9 g of the resin obtained in Example I are stirred with 6 ml of acetic anhydride and 6 ml of triethyl orthobenzoate for 3 hours at 110°C. Then the mixture is left to cool and the resin is washed with dimethylformamide and subsequently with methylene chloride. Yield: 1.9 g of moist resin The following charged resins are prepared analogously to Example II: (1) resin charged with 3-Z-(1-ethoxy-methylene)-6-carbamoyl-2- indolinone Prepared by reacting the resin obtained according to Example I with triethyl orthoformate (2) resin charged with 3-Z-(1-methoxy-1-methyl-methylene)-6- carbamoyl-2 -indolinone Prepared by reacting the resin obtained according to Example I with trimethyl orthoacetate (3) resin charged with 3-Z-(1-methoxy-l-ethyl-methylene)-6- carbamoyl-2 -indolinone Prepared by reacting the resin obtained according to Example" I with trimethyl orthopropionate (4) resin charged with 3-Z-(1-methoxy-l-propyl-methylene)-6- carbamoyl-2-indolinone Prepared by reacting the product of Example I and trimethyl orthobutyrate Example III N-(4-nitrophenyl)-N-methyl-methanesulphonamide 3.0 g of N-methyl-4-nitroaniline are dissolved in 2 0 ml of pyridine and 2.4 g of methanesulphonic acid chloride added dropwise at room temperature. The mixture is stirred for 12 hours at room temperature. After this time the mixture is poured onto water, the precipitate formed is filtered off and dried at 50°C in vafcuo. Yield: 4.0 g (87 % of theory), Rf value: 0.5 (silica gel, ethyl acetate/toluene = 7:3) Melting point: 107-108 °C Example IV N-(2-dimethylamino-ethvl)-N-methylsulphonyl-4-nitroaniline 38.9 g of N-methylsulphonyl-4-nitroaniline are dissolved in 2.0 1 of acetone, 51.9 g of l-chloro-2-dimethylamino-ethane, 77.4 g of potassium carbonate and 5.0 g of sodium iodide are added and the mixture is stirred for a total of 4 days at 50°C, while after 12 hours a further 25.9 g of l-chloro-2-dimethylamino-ethane, 49.8 g of potassium carbonate and 5.0 g of sodium iodide in 500 ml of acetone are added and after 3 6 hours another 26.0 g of l-chloro-2-dimethylamino-ethane, 50.0 g of potassium carbonate and 5.0 g of sodium iodide in 100 ml of acetone are added. After this time the mixture is filtered and the filtrate evaporated down. The residue is stirred with ether, suction filtered and dried at 40°C. Yield: 25.3 g (49 % of theory), Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia = 9:1:0.1) ESI mass spectrum: m/z = 288 [M-t-H+l The following compounds are prepared analogously to Example IV: (1) 4- [N-(3-dimethylamino-propyl)-N-methylsulphonyl-amino]-nitrobenzene (2) N-carboxymethyl-N-methylsulphonyl-4-nitroaniline (3) N-cyanomethyl-N-methylsulphonyl-p-phenylenediamine (4) 4- [N- (2- (N-benzyl-N-methyl-amino) -ethyl) -li¬me thyl sulphonyl-amino] -nitrobenzene (5) 4- [N-(3-phthalimido-2-yl-propyl)-N-methylsulphonyl-amino]-nitrobenzene (6) 4-[N- (3-(N-benzyl-N-methyl-amino)-propyl)-N- methylsulphonyl-amino]-nitrobenzene Example V N-(dimethylaminocarbonyl-methyl)-N-methylsulphonyl-4- nitroaniline _____ 7.0 g of N-carboxymethyl-N-methylsulphonyl-4-nitroaniline, 2.5 g of dimethylamine hydrochloride, 8.1 g of TBTU and 3.9 g of HOBT are dissolved in 125 ml of dimethylformamide and at 0°C 17.6 ml of N-ethyl-diisopropylamine are added. The mixture is stirred for 4 hours at room temperature, diluted with 1 1 of water and the precipitate formed is suction filtered. After washing with water, ethanol and ether the residue is dried at 70°C in vacuo. Yield: 5.3 g (69 % of theory), Rf value: 0.40 (silica gel, methylene chloride/methanol = 9:1) C11H1SN305S ESI mass spectrum: m/z = 300 [M-H~]The following compounds are prepared analogously to Example V: (1) 4-[(N-dimethylaminocarbonylmethyl)-amino] -nitrobenzene ■prepared from 4-(N-carboxymethyl-amino)-nitrobenzene and dimethylamine hydrochloride (2) 4-(N-methylaminocarbonylmethyl-N-methylsulphonyl-amino)- nitrobenzene .," Prepared from N-carboxymethyl-N-methylsulphonyl-4-nitroaniline and rnethylamine hydrochloride (3) 4-[(N-(methylcarbamoyl-methyl)-N-methyl-amino)-methyl]- nitrobenzene Prepared from 4-[(N-carboxymethyl-N-methyl-amino)-methyl]-nitrobenzene and rnethylamine hydrochloride (4) 4-[(N-(dimethylcarbamoyl-methyl)-N-methyl-amino)-methyl]- nitrobenzene Prepared from 4-[(N-carboxymethyl-N-methyl-amino)-methyl]-nitrobenzene and dimethylamine hydrochloride Example VI 4-fN-(2-dimethvlamino-ethvl)-N-acetyl-amino]-nitrobenzene 3.6 g of 4-(2-dimethylamino-ethylamino)-nitrobenzene (according to Gabbay et al., J. Am. Chem. Soc. 91, 5136 (1969)) are dissolved in 50 ml of methylene chloride and 5.0 ml of triethylamine are added. 1.3 ml of acetyl chloride are slowly added dropwise to this mixture at room temperature and the mixture is stirred for 2 hours at room temperature. After this time another 5.0 ml of triethylamine and 1.3 ml of acetylchloride are added and the mixture is refluxed for another 2 hours. The solvent is removed, the residue is taken up in ethyl acetate and the organic phase is extracted twicewith water. After drying over MgS04 the solvent is removed and the residue dried in vacuo. Yield: 2.0 g (45 % of theory), Rf value: 0.55 (silica gel, methylene chloride/methanol/ammonia = 9:1:0.1) C12H17N303 ESI mass spectrum: m/z = 252 [M+H+] The following compounds are prepared analogously to Example VI: (1) 4-[N-(3-dimethylamino-propyl)-N-acetyl-amino]-nitrobenzene Prepared from 4-(3-dimethylamino-propylamino)-nitrobenzene (according to Gabbay et al., J. Am. Chem. Soc. 91, 5136 (1969) and acetyl chloride (2) 4-[N-(2-dimethylamino-ethyl)-N-propionyl-amino]- nitrobenzene Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and propionyl chloride (3) 4- [N-acetyl-N-(dimethylaminocarbonylmethyl)-amino]- nitrobenzene Prepared from 4-[N-(dimethylaminocarbonylmethyl)-amino]-nitrobenzene and acetyl chloride (4) 4-[N-(2-dimethylamino-ethyl)-N-butyryl-amino]-nitrobenzene Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and butyryl chloride (5) 4-[N-(2-dimethylamino-ethyl)-N-isobutyryl-amino]-nitrobenzene Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and isobutyryl chloride (6) 4-[N-(2-dimethylamino-ethyl)-N-benzoyl-amino]-nitrobenzene Prepared from 4-(2-dimethylamxno-ethylamino)-nitrobenzene and benzoyl chloride (7) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-1,3-dinitrobenzene Prepared from 4 -(2-dimethylamino-ethyl-amino)-1,3 -dinitrobenzene and acetyl chloride (8) 4-[N-(2-dimethylamino-ethyl)-N-(furan-2-carbonyl)-amino]- nitrobenzene Prepared from 4-(2-dimethylamxno-ethylamino)-nitrobenzene and furan-2-carbonyl chloride (9) 4-[N-(2-dimethylamino-ethyl)-N-(2-methoxy-benzoyl)-amino]- nitrobenzene Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and 2-methoxy-benzoyl chloride (10) 4-[N-(2-dimethylamino-ethyl)-N-(pyridine-3-carbonyl)- amino]-nitrobenzene Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and nicotinic acid chloride (11) 4-[N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)-amino]- nitrobenzene Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and phenylacetyl-chloride (12) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-3-bromo- nitrobenzene Prepared from 4-[N-(2-dimethylamino-ethyl)-amino]-3-bromo-nitrobenzene and acetyl chloride (13) N-acryloyl-N-methyl-4-nitro-aniline Prepared from 4-methylamino-nitrobenzene and acrylic acid chloride (14) N-acryloyl-N-isopropyl-4-nitro-aniline Prepared from 4-isopropylamino-nitrobenzene and acrylic acid chloride (15) N-acryloyl-N-benzyl-4-nitro-aniline Prepared from 4-ben.zylamino-nitrobenzene and acrylic acid chloride (16) N-bromoacetyl-N-methyl-4-nitro-aniline Prepared from 4-methylamino-nitrobenzene and bromoacetyl chloride (17) N-bromoacetyl-N-isopropyl-4-nitro-aniline Prepared from 4-isopropylamino-nitrobenzene and bromoacetyl chloride (18) N-bromoacetyl-N-benzyl-4-nitro-aniline Prepared from 4-benzylamino-riitrobenzene and bromoacetyl chloride Example VII N-(dimethylaminomethvlcarbonyl)-N-methyl-4-nitro-aniline 1.8 g of dimethylamine hydrochloride and 5.5 g of potassium carbonate are placed in 8 0 ml of acetone and 4.2 g of N-bromoacetyl-N-methyl-4-nitroaniline are added in three batches at room temperature. The mixture is stirred for 12 hours at room temperature. After this time the mixture is filtered and the filtrate is evaporated down. The residue is dissolved in ethyl acetate,, washed twice with water,, dried over sodium sulphate and finally concentrated by rotary evaporation. Yield: 2.8 g (79 % of theory), Rf value: 0.5 (silica gel, ethyl acetate/methanol = 7:3) Melting point: 121-122°C The following compounds are prepared analogously to Example VII: (1) N-(piperidin-1-yl-methylcarbonyl)-N-methyl-4-nitroaniline (2) N-(morpholin-4-yl-methylcarbonyl)-N-methyl-4-nitroaniline (3) N-[(4-benzyl-piperazin-l-yl)-methylcarbonyl]-N-methyl-4-nitroaniline (4) N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl-4-nitroaniline (5) N-[(N-aminocarbonylmethyl-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline (6) N-[(N-benzyl-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline (7) N-[di-(2-methoxyethyl)-amino-methylcarbonyl]-N-methyl-4-nitroaniline (8) N-(dimethylaminomethylcarbonyl)-N-isopropyl-4-nitro-aniline (9) N-(piperidin-1-yl-methylcarbonyl)-N-isopropyl-4-nitro-aniline (10) N-[(4-tert.butoxycarbonyl-piperazin-1-yl)-methylcarbonyl]-N-isopropyl-4-nitro-aniline (11) N-[(N-benzyl-N-methyl-amino)-methylcarbonyl]-N-benzyl-4-nitro-aniline (12) N-(dimethylaminomethylcarbonyl)-N-benzyl-4-nitro-aniline (13) N-(piperidin-1-yl-methylcarbonyl)-N-benzyl-4-nitro-aniline (13) N-[di-(2-hydroxyethyl)-amino-methylcarbonyl]-N-methyl-4-nitroaniline (14) N-[(N-(2-methoxyethyl)-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline (15) N-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline (16) N-[(4-methyl-piperazin-1-yl)-methylcarbonyl]-N-methyl-4-nitroaniline (17) N- [ (imidazol-1-yl) -methylcarbonyl] -N-"methyl-4-nitroaniline (18) N-[(phthalimido-2-yl)-methylcarbonyl]-N-methyl-4-nitroaniline Example VIII N-f(2-dimethylamino-ethyl)-carbonvl]-N-benzvl-4-nitro-aniline 0.5 g of dimethylamine hydrochloride, 1.1 ml of triethylamine and 1.2 g of N-acryloyl-N-benzyl-4-nitro-aniline are dissolved in 50 ml of methanol and stirred for 24 hours at room temperature. After this time the mixture is evaporated down. The residue is purified over an aluminium oxide column (activity 2-3) with methylene chloride/ethanol 50:1 as eluant. Yield: 1.4 g (98 % of theory), Rf value: 0.8 (aluminium oxide, methylene chloride/ethanol = 20:1) Melting point: 73°C The following compounds are prepared analogously to Example VIII: (1) N-[(2-dimethylamino-ethyl)-carbonyl] -N-isopropyl-4-nitro- aniline Prepared from N-acryloyl-N-isopropyl-4-nitro-aniline and dimethylamine hydrochloride (2) N- [ (2-dimethylathino-ethyl) -carbonyl] -N-methyl-4-nitro- aniline Prepared from N-acryloyl-N-methyl-4-nitro-aniline and dimethylamine hydrochloride (3) N- [(2-(4-tert.butoxycarbonyl-piperazin-1-yl)-ethyl)- carbonyl]-N-methyl-4-nitro-aniline Prepared from N-acryloyl-N-methyl-4-nitro-aniline and N-tert.butoxycarbonyl-piperazine (4) N-[(2-(piperidin-1-yl)-ethyl)-carbonyl] -N-methyl-4-nitro- aniline Prepared from N-acryloyl-N-methyl-4-nitro-aniline and piperidine (5) N-[(2-(N-benzyl-N-methyl-amino)-ethyl)-carbonyl]-N-methyl- 4-nitro-aniline Prepared from N-acryloyl-N-methyl-4-nitro-aniline and N-benzyl-N-methyl-amine Example IX 4-(4-methyl-piperazine-l-yl)-nitrobenzene 31.5 g of 4-chloro-l-nitrobenzene and 44.4 ml of 1-methylpiperazine are combined and stirred for 18 hours at 90°C. Then the solution is poured onto ice water and the precipitate formed is suction filtered, washed with water and recrystallised from ethanol/water 1:1. The residue is dried in vacuo at 75°C. Yield: 44.0 g (99 % of theory), Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) Melting point: 108-112°C The following compounds are prepared analogously to Example IX: (1) N-(2-dimethylaminoethyl)-N-methyl-4-nitroaniline Prepared from 1-fluoro-4-nitrobenzene and l-dimethylamino-2-methylamino-ethane (2) N-(3-dimethylaminopropyl)-N-methyl-4-nitroaniline Prepared from 1-fluoro-4-nitrobenzene and l-dimethylamino-3-methylamino-propane (3) 4-(N-carboxymethyl-amino)-nitrobenzene Prepared from 1-fluoro-4-nitrobenzene and glycine (4) N-cyclohexyl-p-phenylenediamine Prepared from 1-fluoro-4-nitrobenzene and cyclohexylamine (5) 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3- phthalimido-2-yl-nitrobenzene Prepared from 2-nitro-4-phthalimido-2-yl-fluorobenzene, N-(2-dimethylamino-ethyl)-methanesulphonamide and sodium hydride as base (6) 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-1,3- dinitrobenzene Prepared from 2,4-dinitro-chlorobenzene, N-(2-dimethylamino-ethyl) -methanesulphonamide and sodium hydride as base (7) 4-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3- chloro-nitrobenzene Prepared from 2-fluoro-5-nitro-chlorobenzene, N-(2-dimethyl¬amino-ethyl) -methanesulphonamide and sodium hydride as base (8) 4-(2-dimethylamino-ethyl-amino)-1, 3-dinitrobenzene Prepared from l-chloro-2,4-dinitro-benzene and N, N-dimethyl-ethylenediamine (9) 4-[N-(2-dimethylamino-ethyl)-N-(ethylsulphonyl)-amino]-nitrobenzene Prepared from 1-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -ethanesulphonamide and sodium hydride as base (10) 4- [N- (2-dimethylamino-ethyl) -N- (propylsulphonyl) -amino] - nitrobenzene Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -propanesulphonamide and sodium hydride as base (11) 4-[N-(2-dimethylamino-ethyl)-N-(butylsulphonyl)-amino]- nitrobenzene Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -butanesulphonamide and sodium hydride as base (12) 4- [N- (2-dimethylamino-ethyl) -N- (benzylsulphonyl) -amino] - nitrobenzene Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -C-phenylmethanesulphonamide and sodium hydride as base (13) 4- [N- (2-dimethylamino-ethyl) -N- (phenylsulphonyl) -amino] - nitrobenzene Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -benzenesulphonamide and sodium hydride as base (14) 4-[N-(2-dimethylamino-ethyl)-N-(isopropylsulphonyl)- amino]-nitrobenzene Prepared from 1-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl)-isopropylsulphonamide and sodium hydride as base (15) 4- [N-(2-dimethylamino-ethyl)-amino]-3-bromo-nitrobenzene Prepared from 2-bromo-l-fluoro-4-nitro-benzene and N,N-dimethyl-ethylenediamine (16) 4-isopropylamino-nitrobenzene Prepared from 1-flu6ro-4-nitrobenzene and isopropylamine (17) 4-benzylamino-nitrobenzene Prepared from 1-fluoro-4-nitrobenzene and benzylamine Example X 4-(imidazol-4-vl)-nitrobenzene 9.5 g of 2-phenylimidazole are carefully dissolved in 50 ml of concentrated sulphuric acid and 5.8 g of ammonium nitrate are added to this solution at 0°C. After a further 60 minutes stirring at 0°C the mixture is poured onto ice water, made basic with ammonia water and the precipitate formed is suction filtered and recrystallised from ethanol. Yield: 8.0 g (64 % of theory), Rf value: 0.6 (silica gel, ethyl acetate/ethanol = 10:1) C9H7N302 Mass spectrum: m/z = 189 [M+] The following compounds are prepared analogously to Example X: (1) 4 -(imidazol-2-yl)-nitrobenzene Prepared from 4-(imidazol-2-yl)-benzene (2) 4-(5-methyl-imidazol-4-yl)-nitrobenzene Prepared from 4-methyl-5-phenyl-imidazole (J. Heterocycl. Chem. 1983, 20, 1277-1281) Example XI 4-(2-(imidazol-4-yl)-ethylene)-nitrobenzene 1.5 g of 4-nitrobenzaldehyde and 7.45 g of (N-trityl-imidazol-4-yl-methyl)-triphenylphosphonium chloride are dissolved in 75 ml of tetrahydrofuran and to this solution 3.0 ml of DBU are added dropwise at room temperature. After a further 120 minutes stirring at room temperature the mixture is poured onto water and the precipitate formed is suction filtered. The product is taken up in 25 ml of IN hydrochloric acid and refluxed for 4 hours. After this time it is neutralised with ammoniacal water, extracted with ethyl acetate and the organic phase is washed with water, dried over sodium sulphate and evaporated down. The residue is purified over a silica gel column with methylene chloride/methanol 10:1 as eluant. Yield: 1.0 g of (47 % of theory), Rf value: 0.6 (silica gel, ethyl acetate/ethanol = 10:1) Melting point: 185-188°C Example XII 4-(piperidin-1-yl-methvl)-nitrobenzene 40.0 g of 4-nitrobenzyl bromide are dissolved in 500 ml of methylene chloride, 51.5 ml of triethylamine are added and 18.3 ml of piperidine are carefully added dropwise. After the end of the exothermic reaction the mixture is refluxed for another 30 minutes. After cooling it is washed with water and the organic phase is dried over sodium sulphate. Finally, the organic phase is evaporated down. Yield: 36.3 g of, (89 % of theory), Rf value: 0.6 (silica gel, methylene chloride/methanol = 9:1) C12H16N202 Mass spectrum: m/z = 221 [M+] The following compounds are prepared analogously to Example XII: (1) 4-[(2,6-dimethyl-piperidin-l-yl) -methyl]-nitrobenzene (2) 3-(N,N-dimethyl-aminomethyl)-nitrobenzene (3) 4-(N,N-dimethyl-aminomethyl)-nitrobenzene l (4) 4-(2-dimethylamino-ethyl)-nitrobenzene (5) 4-(2-diethylamino-ethyl)-nitrobenzene (6) 4-(diethylamino-methyl)-nitrobenzene (7) 4-(N-benzyl-N-methyl-aminomethyl) -nitrobenzene (8) 4-(N-ethyl-N-methyl-aminomethyl)-nitrobenzene (9) 4-[N-(n-hexyl)-N-methyl-aminomethyl]-nitrobenzene (10) 4-(thiomorpholin-4-yl-methyl)-nitrobenzene (11) 4-[(4-methyl-piperazine-l-yl) -methyl]-nitrobenzene (12) 4 -(imidazol-1-yl-methyl)-nitrobenzene (13) 4- [2- (4-hydroxy-piperidin-l-yl) -ethyl-amino] -nitrobenzene (14) 4- [ (3-hydroxy-pyrrolidin-l-yl) -methyl] -nitrobenzene (15) 4-(1,2,4-triazol-1-yl-methyl)-nitrobenzene (16) 4-(1,2,3-triazol-2-yl-methyl)-nitrobenzene (17) 4-(1,2,3-triazol-l-yl-methyl)-nitrobenzene (18) 4-[(N-ethoxycarbonylmethyl-N-methyl-amino)-methyl]-nitrobenzene (19) 4-[(N-aminocarbonylmethyl-N-methyl-amino)-methyl]-nitrobenzene (20) 4-(azetidin-1-yl-methyl)-nitrobenzene (21) 4-[(di-(2-methoxy-ethyl)-amino)-methyl]-nitrobenzene (22) 4-[N-(N-tert.butoxycarbonyl-3-amino-propyl)-N-methyl-aminomethyl]-nitrobenzene (23) 4-[(N-propyl-N-methyl-amino)-methyl]-nitrobenzene (24) 4-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)-methyl]-nitrobenzene (25) 4-[(N-(3-dimethylamino-propyl)-N-methyl-amino)-methyl]-nitrobenzene (26) 4-[(N-(2-methoxy-ethyl)-N-methyl-amino)-methyl]-nitrobenzene (27) 4-[(N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl]-nitrobenzene (28) 4-[(N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl]-nitrobenzene (29) 4-(3-oxo-piperazine-l-yl-methyl)-nitrobenzene Example XIII 4-[(N-carboxymethvl-N-methyl-amino)-methyll-nitrobenzene 7.33 g of 4-[(N-ethoxycarbonylmethyl-N-methyl-amino)-methyl] - nitrobenzene are dissolved in 140 ml of ethanol, 34.0 ml of IN sodium hydroxide solution are added and the mixture is stirred for half an hour at room temperature. After this time the mixture is neutralised with 34 ml of IN hydrochloric acid, the solvent removed, the residue taken up in methylene chloride and extracted with water. The aqueous phase is evaporated down and the residue is recrystallised from methylene chloride. Yield: 5.43 g (84 % of theory), Rf value: 0.4 (silica gel, methylene chloride/methanol = 2:1) C10H12N2O4 Mass spectrum: m/z = 223 [M+] Example XIV 4-(N-ethyl-aminomethyl)-nitrobenzene 6.0 g of 4-nitrobenzyl bromide are dissolved in 25 ml of ethanol, combined with 25 ml of 10% ethanolic ethylamine solution and refluxed for 2 hours. Then the solution is concentrated by rotary evaporation, the residue is taken up with methylene chloride and washed with dilute sodium hydroxide solution. Finally the organic phase is evaporated down. Yield: 2.3 g (46 % of theory), R£ value: 0.2 (silica gel, methylene chloride/methanol = 9:1) C9H12N202 ESI mass spectrum: m/z = 179 [M-H~] The following compounds are prepared analogously to Example XIV: (1) 4-[N-(4-chlorobenzyl)-aminomethyl] -nitrobenzene (2) 4-(N-cyclohexyl-aminomethyl)-nitrobenzene (3) 4-(N-isopropyl-aminomethyl)-nitrobenzene (4) 4-(N-propyl-aminomethyl)-nitrobenzene (5) 4-(N-methyl-aminomethyl)-nitrobenzene (6) 4-(N-butyl-aminomethyl)-nitrobenzene (7) 4-(N-methoxycarbonylmethyl-aminomethyl)-nitrobenzene (8) 4-(N-benzyl-aminomethyl)-nitrobenzene (9) 4-(aminomethyl)-nitrobenzene (10) 4-(pyrrolidin-1-yl-methyl)-nitrobenzene (11) 4-(morpholin-4-yl-methyl)-nitrobenzene (12) 4-(hexamethyleneiminomethyl)-nitrobenzene (13) 4-(4-hydroxy-piperidin-1-yl-methyl)-nitrobenzene (14) 4-(4-methoxy-piperidin-1-yl-methyl)-nitrobenzene (15) 4-(4-methyl-piperidin-l-yl-methyl)-nitrobenzene (16) 4-(4-ethyl-piperidin-l-yl-methyl)-nitrobenzene (17) 4-(4-isopropyl-piperidin-l-yl-methyl)-nitrobenzene (18) 4-(4-phenyl-piperidin-l-yl-methyl)-nitrobenzene (19) 4-(4-benzyl-piperidin-l-yl-methyl)-nitrobenzene (2 0) 4-(4-ethoxycarbonyl-piperidin-1-yl-methyl)-nitrobenzene (21) 4-(N,N-dipropyl-aminomethyl)-nitrobenzene (22) 4-(4-tert.butoxycarbonyl-piperazin-1-yl-methyl)-nitrobenzene (23) 4- (2-morpholinJ-4-yl-ethyl) -nitrobenzene (24) 4-(2-pyrrolidin-l-yl-ethyl)-nitrobenzene (25) 4-(2-piperidin-l-yl-ethyl)-nitrobenzene (26) 4-(N-ethyl-N-benzyl-aminomethyl)-nitrobenzene (27) 4-(N-propyl-N-benzyl-aminomethyl)-nitrobenzene (28) 4-[N-methyl-N-(4-chlorobenzyl)-aminomethyl]-nitrobenzene (29) 4-[N-methyl-N-(4-bromobenzyl)-aminomethyl] -nitrobenzene (30) 4-[N-methyl-N-(4-fluorobenzyl)-aminomethyl]-nitrobenzene (31) 4-[N-methyl-N-(4-methylbenzyl)-aminomethyl]-nitrobenzene (32) 4-[N-methyl-N-(3-chlorobenzyl)-aminomethyl]-nitrobenzene (33) 4-[N-methyl-N-(3,4-dimethoxybenzyl)-aminomethyl]-nitrobenzene (34) 4-[N-methyl-N-(4-methoxybenzyl)-aminomethyl]-nitrobenzene (35) 4-(N-2,2,2-trifluoroethyl-N-benzyl-aminomethyl)-nitrobenzene (36) 4-[N-2,2,2-trifluoroethyl-N-(4-chlorobenzyl)-aminomethyl]-nitrobenzene (37) 4-(thiomorpholin-4-yl-methyl)-nitrobenzene (38) 4-(azetidion-1-yl-methyl)-nitrobenzene (39) 4-(3,4-dihydropyrrolidin-1-yl-methyl)-nitrobenzene (40) 4-(3,4-dihydropiperidin-l-yl-methyl)-nitrobenzene (41) 4- (2-methoxycarbonyl-pyrrolidin-l-yl-methyl) -nitrobenzene (42) 4- (3,5-dimethyl-piperidin-l-yl-methyl) -nitrobenzene (43) 4-(4-phenyl-piperazin-l-yl-methyl)-nitrobenzene (44) 4-(4-phenyl-4-hydroxy-piperidin-1-yl-methyl)-nitrobenzene (45) 4-[N-(3,4,5-trimethoxybenzyl-N-methyl-aminomethyl)-nitrobenzene (46) 4-[N-(3,4-dimethoxybenzyl)-N-ethyl-aminomethyl]-nitrobenzene (47) 4-[N-(2,6-dichlorobenzyl)-N-methyl)-aminomethyl]-nitrobenzene (48) 4-[N-(4-trifluoromethylbenzyl)-N-methyl)-aminomethyl] -nitrobenzene (49) 4-(N-benzyl-N-isopropyl-aminomethyl)-nitrobenzene (50) 4-(N-benzyl-N-tert.butyl-aminomethyl)-nitrobenzene (51) 4-(N,N-diisopropyl-aminomethyl)-nitrobenzene (52) 4-(N,N-diisobutyl-aminomethyl)-nitrobenzene (53) 4-(2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene (54) 4-(2,3-dihydro-isoindol-2-yl-methyl)-nitrobenzene (55) 4- (6, 7-dimethoy-l, 2,3, 4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene (56) 4-(l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene (57) 4-[N-(2-hydroxyethyl)-N-benzyl-aminomethyl]-nitrobenzene (58) 4-[N-(1-ethyl-pentyl)-N-(pyridin-2-yl-methyl)-aminomethyl]-nitrobenzene (59) 4-(piperin-1-yl-methyl)-1,3-dinitrobenzene (60) 4-(N-phenethyl-N-methyl-aminomethyl)-nitrobenzene (61) 4-[N-(3,4-dihydroxy-phenethyl)-N-methyl-aminomethyl]-nitrobenzene (62) 4-[N-(3, 4,5-trimethoxy-phenethyl)-N-methyl-aminomethyl]-nitrobenzene (63) 4-[N-(3,4-dimethoxy-phenethyl)-N-methyl-aminomethyl]-nitrobenzene (64) 4-[N-(3,4-dimethoxy-benzyl)-N-methyl-aminomethyl]-nitrobenzene (65) 4-[N-(4-chloro-benzyl)-N-methyl-aminomethyl]-nitrobenzene(66) 4- [N-(4-bromo-benzyl)-N-methyl-aminomethyl]-nitrobenzene (67) 4-[N-(4-fluoro-benzyl)-N-methyl-aminomethyl]-nitrobenzene (68) 4- [N-(4-methyl-benzyl)-N-methyl-aminomethyl]-nitrobenzene (69) 4-[N-(4-nitro-phenethyl)-N-methyl-aminomethyl]-nitrobenzene " (70) 4-(N-phenethyl-N-benzyl-aminomethyl)-nitrobenzene (71) 4-(N-phenethyl-N-cyclohexyl-aminomethyl)-nitrobenzene (72) 4-[N-(2-(pyridin-2-yl)-ethyl)-N-methyl-aminomethyl]-nitrobenzene (73) 4-[N-(2-(pyridin-4-yl)-ethyl)-N-methyl-aminomethyl]-nitrobenzene (74) 4-[N-(pyridin-4-yl-methyl)-N-methyl-aminomethyl]-nitrobenzene (75) 4-(N,N-dibenzyl-aminomethyl)-nitrobenzene (76) 4-[N-(4-nitro-phenethyl)-N-propyl-aminomethyl]-nitrobenzene (77) 4-(N-benzyl-N-(3-cyano-propyl)-aminomethyl)-nitrobenzene (78) 4-(N-benzyl-N-allyl-aminomethyl)-nitrobenzene (79) 4-[N-benzyl-N-(2,2,2-trifluoroethyl)-aminomethyl]- nitrobenzene4-[N-(2-benzo(l,3)dioxol-5-yl-methyl)-N-methyl-aminomethyl]-nitrobenzene (80) 4-(7-chloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene (81) 4-(7,8-dichloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene (82) 4-(7-methoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene (83) 4- (7-rnethyl-2, 3,4, 5-tetrahydro-benzo(d) azepin-3-yl-methyl)-nitrobenzene (84) 4-(7,8-dimethoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene (85) 4-(6,7-dichloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene (86) 4-(6,7-dimethyl-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene (87) 4-(6-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene (88) 4-(7-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene (89) 4-(6-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene (90) 4-(7-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl) -nitrobenzene (92) 4-[(2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl)-methyl]-nitrobenzene (93) 4-[(7-amino-2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl)-methyl]-nitrobenzene (94) 4-[(2-amino-5,6,7,8-tetrahydro-azepino(4,5-d)thiazol-6-yl)-methyl]-nitrobenzene (95) 4-[(5,6,7,8-tetrahydro-azepino(4,5-d)thiazol-6-yl)-methyl]-nitrobenzene Example XV 4-(1,l-dioxo-thiomorpholin-4-yl-methyl)-nitrobenzene 6.0 g of 4-(thiomorpholin-4-yl-methyl)-nitrobenzene are dissolved in 100 ml of methylene chloride and 10.3 g of meta- chloroperbenzoic acid are slowly added. After a further 3 hours stirring at room temperature the precipitate obtained is filtered off. Yield: 6.2 g (91 % of theory) Rf value: 0.5 (silica gel, methylene chloride/methanol = 1:1) CnH14N204S Mass spectrum: m/z = 270 [M+] The following compound is prepared analogously to Example XV: (1) 4-(1-oxo-thiomorpholin-4-yl-methyl)-nitrobenzene Example XVI 4-fN-(3-amino-propyl)-N-methvlsulphonyl-amino]-nitrobenzene 9.5 g of 4-[N-(3-phthalimido-2-yl-propyl)-N-methylsulphonyl-amino] -nitrobenzene are dissolved in 200 ml of ethanol, 11.5 ml of hydrazine hydrate are added and the mixture is stirred for 1.5 hours at 50 °C. After cooling the residue is largely evaporated down, water is added and the solution is extracted with methylene chloride. The organic phase is dried, evaporated down and purified over a silica gel column with methylene chloride/methanol/ammonia 9:1:0.1. Yield: 2.5 g (39 % of theory) Rf value: 0.2 (silica gel, methylene chloride/methanol = 9:1) C10H15N3O4S ESI mass spectrum: m/z = 272 [M-H"] The following compound is prepared analogously to Example XVI: (1) 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-amino-nitrobenzene Prepared from 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-phthalimido-2-yl-nitrobenzene Example XVII 4-(l-methyl-imidazol-2-yl)-nitrobenzene 7.5 g of 4-(imidazol-2-yl)-nitrobenzene are dissolved in 50 ml of dimethylsulphoxide and at 0°C 5.0 g of potassium tert.butoxide are added. After one hour of stirring at room temperature 2.6 ml of methyl iodide are added dropwise and the mixture is stirred for one hour at room temperature. After this time the residue is poured onto ice water and the precipitate formed is suction filtered, washed with water and dried. Yield: 6.1 g (76 % of theory) Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1) Melting point: 186-187°C The following compounds are prepared analogously to Example XVII: (1) 4-(l-ethyl-imidazol-2-yl)-nitrobenzene Prepared from 4-(imidazol-2-yl)-nitrobenzene and ethyl iodide (2) 4-(l-benzyl-imidazol-2-yl)-nitrobenzene Prepared from 4-(imidazol-2-yl)-nitrobenzene and benzyl bromide Example XVIII 4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]- nitrobenzene 5.0 g of 4-methylaminomethyl-nitrobenzene are dissolved in 30 ml of dimethylformamide and 4.6 g of 2-(2-methoxy-ethoxy)- ethyl chloride are added. After six hours" stirring at 100°C the solvent is removed and the residue is taken up in ethyl acetate. The organic phase is washed with water and dried over sodium sulphate. After the elimination of the solvent the residue is purified over an aluminium oxide column (activity 2-3) with toluene/ethyl acetate 5:1 as eluant. Yield: 2.3 g (29 % of theory) Rf value: 0.5 (aluminium oxide, toluene/ethyl acetate = 5:1) C13H20N2O4 ESI mass spectrum: m/z = 267 [M-H~] Example XIX 4-(N-ethyl-N-tert.butoxvcarbonyl-aminomethyl)-nitrobenzene 2.2 g of 4-(ethylaminomethyl)-nitrobenzene are dissolved in 50 ml of ethyl acetate and stirred with 2.6 g of di-tert-butyl. dicarbonate (tert.butoxycarbonyl-anhydride) for 30 minutes at room temperature. Then the solution is washed with water and evaporated down. Yield: 3.4 g of theory Rf value: 0.3 (silica gel, methylene chloride/methanol = 50:1) Melting point: 85 °C The following compounds are prepared analogously to Example XIX: (1) 4-[N-(4-chlorophenyl-methyl)-N-tert.butoxycarbonyl-aminomethyl] -nitrobenzene (2) 4-(N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene (3) 4-(N-cyclohexyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene (4) 4-(N-isopropyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene (5) 4-(N-methyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene (6) 4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene (7) 4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene (8) 4-(N-methoxycarbonylmethyl-N-tert.butoxycarbonyl-aminomethyl) -nitrobenzene (9) 4-(N-benzyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene (10) 4- [N- (3-trifluoroacetylamino-propyl) -N-methylsulphonyl- amino]-nitrobenzene Prepared from 4- [N- (3-amino-propyl) -N-methylsulphonyl-amino] -nitrobenzene and trifluoroacetic acid anhydride (11) 4-[(4-tert.butoxycarbonyl-piperazin-1-yl)-methyl] - nitrobenzene Example XX 4-(piperidin-1-yl-methvl)-aniline 37.0 g of 4-(piperidin-1-yl-methyl)-nitrobenzene are dissolved in 3 00 ml of methanol, 8.0 g of Raney nickel are added and the mixture is hydrogenated for 85 minutes with 3 bars of hydrogen at room temperature. The catalyst is filtered off and the filtrate is evaporated down. Yield: 24.0 g (75 % of theory), R£ value: 0.4 (silica gel, methylene chloride/methanol = 9:1) C12H18N2 ESI mass spectrum: m/z = 191 [M+H+] The following compounds are prepared analogously to Example VIII: (1) 4-[(2,6-dimethyl-piperidin-l-yl)-methyl]-aniline (2) N-(2-dimethylamino-ethyl)-N-methylsulphonyl-p-phenylenediamine (3) 3-(dimethylaminomethyl)-aniline (4) 4-(dimethylaminomethyl)-aniline (5) 4-(2-dimethylamino-ethyl)-aniline (6) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-aniline (7) 4-[N-(3-dimethylamino-propyl)-N-acetyl-amino]-aniline (8) 4-[N-(2-dimethylamino-ethyl)-N-benzoyl-amino]-aniline (9) 4-[N-(2-dimethylamino-ethyl)-N-propionyl-amino]-aniline (10) 4-[N-(2-dimethylamino-ethyl)-N-butyryl-amino]-aniline (11) 4-[N-(2-dimethylamino-ethyl)-N-isobutyryl-amino]-aniline (12) 4-(N-tert.butoxycarbonyl-aminomethyl)-aniline (13) 4-(N-ethyl-N-tert.butoxycarbonyl-aminomethyl)-aniline (14) 4-[N-(4-chlorophenyl-methyl)-N-tert.butoxycarbonyl-aminomethyl] -aniline (15) 4-(N-cyclohexyl-N-tert.butoxycarbonyl-aminomethyl)-aniline (16) 4-(N-isopropyl-N-tert.butoxycarbonyl-aminomethyl)-aniline (17) 4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)-aniline (18) 4-(N-methyl-N-tert.butoxycarbonyl-aminomethyl)-aniline (19) 4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)-aniline (2 0) 4-(N-methoxycarbonyl-methyl-N-tert.butoxycarbonyl-aminomethyl) -aniline (21) 4-(N-benzyl-N-tert.butoxycarbonyl-aminomethyl)-aniline (22) 4-(pyrrolidin-1-yl-methyl)-aniline (23) 4-(morpholin-4-yl-methyl)-aniline (24) 4- (hexamethyleneirninomethyl) -aniline (25) 4-(4-hydroxy-piperidin-l-yl-methyl)-aniline (26) 4-(4-methoxy-piperidin-1-yl-methyl)-aniline (27) 4-(4-methyl-piperidin-l-yl-methyl)-aniline (28) 4-(4-ethyl-piperidin-l-yl-methyl)-aniline (29) 4-(4-isopropyl-piperidin-l-yl-methyl)-aniline (30) 4-(4-phenyl-piperidin-l-yl-methyl)-aniline (31) 4-(4-benzyl-piperidin-l-yl-methyl)-aniline (32) 4-(4-ethoxycarbonyl-piperidin-l-yl-methyl)-aniline (33) 4-(N,N-dipropyl-aminomethyl)-aniline (34) 4-(4-tert.butoxycarbonyl-piperazin-1-yl-methyl)-aniline (35) 4-(2-morpholin-4-yl-ethyl)-aniline (36) 4-(2-pyrrolidin-l-yl-ethyl)-aniline (37) 4-(2-piperidin-l-yl-ethyl)-aniline (38) 4-(N-propyl-N-benzyl-aminomethyl)-aniline (39) 4-[N-(n-hexyl)-N-methyl-aminomethyl]-aniline (40) 4-[N-methyl-N-(4-chlorobenzyl)-aminomethyl]-aniline 41) 4-[N-methyl-N-(4-bromobenzyl)-aminomethylJ-aniline (42) 4-[N-methyl-N-(4-methylbenzyl)-aminomethyl]-aniline (43) 4-[N-methyl-N-(4-fluorobenzyl)-aminomethyl]-aniline (44) 4-[N-methyl-N-(3-chlorobenzyl)-aminomethyl]-aniline (45) 4-[N-methyl-N-(3,4-dimethoxybenzyl)-aminomethyl]-aniline (46) 4-[N-methyl-N-(4-methoxybenzyl)-aminomethyl]-aniline (47) 4-(N-2,2,2-trifluoroethyl-N-benzyl-aminomethyl)-aniline (48) 4-[N-2,2,2-trifluoroethyl-N-(4-chlorobenzyl)-aminomethyl]-aniline (49) 4-(thiomorpholin-4-yl-methyl)-aniline (50) 4-(l-oxo-thiomorpholin-4-yl-methyl)-aniline (51) 4-(1,l-dioxo-thiomorpholin-4-yl-methyl)-aniline (52) 4-(azetidion-1-yl-methyl)-aniline (53) 4-(3,4-dihydropyrrolidin-l-yl-methyl)-aniline (54) 4-(3,4-dihydropiperidin-l-yl-methyl)-aniline (55) 4-(2-methoxycarbonyl-pyrrolidin-l-yi-methyl)-aniline (56) 4-(3,5 -dimethyl-piperidin-1-yl-methyl)-aniline (57) 4-(4-phenyl-piperazin-l-yl-methyl)-aniline (58) 4-(4-phenyl-4-hydroxy-piperidin-1-yl-methyl)-aniline (59) 4-[N-(3,4,5-trimethoxy-benzyl)-N-methyl-aminomethyl]-aniline (60) 4-[N-(3,4-dimethoxy-benzyl)-N-ethyl-aminomethyl]-aniline (61) 4-(N-benzyl-N-ethyl-aminomethyl)-aniline (62) 4-[N-(2,6-dichlorobenzyl)-N-methyl-aminomethyl]-aniline (63) 4-[N-(4-trifluoromethylbenzyl)-N-methyl-aminomethyl]-aniline (64) 4-(N-benzyl-N-isopropyl-aminomethyl)-aniline (65) 4-(N-benzyl-N-tert.butyl-aminomethyl)-aniline (66) 4-(diethylamino-methyl)-aniline (67) 4-(2-diethylamino-ethyl)-aniline (68) 4-(N,N-diisopropyl-aminomethyl)-aniline (69) 4-(N,N-diisobutyl-aminomethyl)-aniline (70) 4-(2,3,4,5-tetrahydro~benzo(d)azepin-3-yl-methyl)-aniline (71) 4-(2,3-dihydro-isoindol-2-yl-methyl)-aniline (72) 4-(6,7-dimethoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline (73) 4-(l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline (74) 4-[N-(2-hydroxy-ethyl)-N-benzyl-aminomethyl]-aniline 75) 4- [N-(1-ethyl-pentyl)-N-(pyridin-2-yl-methyl)- aminomethyl]-aniline (76) 4-(piperidin-1-yl-methyl)-3-nitro-aniline (77) 4-(piperidin-1-yl-methyl)-3-amino-aniline (78) 4-(N-benzyl-N-methyl-aminomethyl)-aniline (79) 4-(N-ethyl-N-methyl-aminomethyl)-aniline (80) 4-(N-phenethyl-N-methyl-aminomethyl)-aniline (81) 4-[N-(3,4-dihydroxy-phenethyl)-N-methyl-aminomethyl]-aniline (82) 4-[N-(3,4,5-trimethoxy-phenethyl)-N-methyl-aminomethyl] -aniline (83) 4- [N-(3,4-dimethoxy-phenethyl)-N-methyl-aminomethyl]-aniline (84) 4- [N-(3,4-dimethoxy-benzyl)-N-methyl-aminomethyl]-aniline (85) 4- [N- (4-chloro-benzyl)-N-methyl-aminomethyl]-aniline (86) 4-[N-(4-bromo-benzyl)-N-methyl-aminomethyl]-aniline (87) 4- [N- (4-fluoro-benzyl)-N-methyl-aminomethyl]-aniline (88) 4-[N-(4-methyl-benzyl)-N-methyl-aminomethyl]-aniline (89) 4- [N-(4-nitro-phenethyl)-N-methyl-aminomethyl]-aniline (90) 4-(N-phenethyl-N-benzyl-aminomethyl)-aniline (91) 4-(N-phenethyl-N-cyclohexyl-aminomethyl)-aniline (92) 4-[N-(2-(pyridin-2-yl)-ethyl)-N-methyl-aminomethyl]-aniline (93) 4-[N-(2-(pyridin-4-yl)-ethyl)-N-methyl-aminomethyl]-aniline (94) 4-[N-(pyridin-4-yl-methyl)-N-methyl-aminomethyl]-aniline (95) 4-(N,N-dibenzylaminomethyl)-aniline (96) 4-[N-(4-nitro-benzyl)-N-propyl-aminomethyl]-aniline (97) 4-[N-benzyl-N-(3-cyano-propyl)-aminomethyl]-aniline (98) 4-(N-benzyl-N-allyl-aminomethyl)-aniline (99) 4-[N-benzyl-N-(2,2,2-trifluoroethyl)-aminomethyl]-aniline (100) 4-[(benzo(1,3)dioxol-5-yl-methyl)-methyl-aminomethyl]-aniline (101) 4-(7-chloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline (102) 4-(7,8-dichloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline (103) 4-(7-methoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline (104) 4-(7-methyl-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline (105) 4-(7,8-dimethoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline (10 6) 4-(6,7-dichloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline (107) 4-(6,7-dimethyl-1,2,3,4-tetrahydro-isoquinolin-2-yl- methyl)-aniline (108) 4-(6-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl) - aniline (109) 4-(7-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl) -aniline (110) 4-(6-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline (111) 4-(7-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline (112) 4-(2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl-methyl)-aniline (113) 4-(7-amino-2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl-methyl)-aniline (114) 4-(2-amino-5,6,7,8-tetrahydro-azepino(4, 5-d)thiazol-6-yl-methyl)-aniline (115) 4-(5,6,7,8-tetrahydro-azepino(4, 5-d) thiazol-6-yl-methyl) -aniline (116) 4-(4-methyl-piperazin-l-yl)-aniline (117) 4-[N-(2-dimethylamino-ethyl)-N-methyl-amino]-aniline (118) 4-[N-(3-dimethylamino-propyl)-N-methyl-amino]-aniline (119) N-(3-dimethylamino-propyl)-N-methylsulphonyl-p-phenylenediamine (12 0) 4-[(N-dimethylaminocarbonylmethyl-N-methylsulphonyl)-amino]-aniline (121) N-(4-aminophenyl)-N-methyl-methanesulphonamide (122) 4-(imidazol-4-yl)-aniline (123) 4-(tetrazol-5-yl)-aniline (124) 4-[N-(2-dimethylamino-ethyl)-N-propionyl-amino]-aniline (125) N-(dimethylaminomethylcarbonyl)-N-methyl-p-phenylenediamine (126) N-[(2-dimethylamino-ethyl)-carbonyl]-N-methyl-p-phenylenediamine (127) 4-(N-acetyl-N-dimethylaminocarbonylmethyl)-amino)-aniline (128) N-methylaminocarbonylmethyl-N-methylsulphonyl-p -phenylenediamine (12 9) N-aminocarbonylmethyl-N-methylsulphonyl-p-phenylenediamine (130) 4-(imidazolidin-2,4-dion-5-ylidene-methyl)-aniline (131) 4-(imidazolidin-2,4-dion-5-yl-methyl)-aniline (132) 4-(2-oxo-pyrrolidin-l-yl-methyl)-aniline (133) N-cyanomethyl-N-methylsulphonyl-p-phenylenediamine (134) 4-[2-(imidazol-4-yl)-ethyl] -aniline (135) 4-[(4-methyl-piperazin-l-yl)-methyl]-aniline (136) 4- [N- (2- (N-bejizyl-N-methyl-amino) -ethyl) -N-methylsulphonyl-amino]-aniline (137) 4-[N-(3-(N-benzyl-N-methyl-amino)-propyl)-N-methylsulphonyl-amino]-aniline (13 8) N-cyclohexyl-p-phenylenediamine (13 9) 4-(pyridin-4-yl-methyl)-aniline (140) 4-(imidazol-1-yl-methyl)-aniline (141) 4-benzyl-aniline (142) N-(3-trifluoroacetylamino-propyl)-N-methylsulphonyl-p-phenylenediamine (143) tert.butyl 4-amino-phenylacetate (144) 4-(imidazol-2-yl)-aniline (145) 4-(l-methyl-imidazol-2-yl)-aniline (14G) 4-(l-ethyl-imidazol-2-yl)-aniline (147) 4-(l-benzyl-imidazol-2-yl)-aniline (148) 4-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-amino-ani1ine (149) 4-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-chloro-aniline (150) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-3-amino-aniline (151) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-3-bromo-aniline (152) 4-[2-(4-hydroxy-piperidin-l-yl)-ethyl-amino]-aniline (153) N-(2-dimethylamino-ethyl)-N-ethylsulphonyl-p-phenylenediamine (154) N-(2-dimethylamino-ethyl)-N-propylsulphonyl-p-phenylenediamine (155) N-(2-dimethylamino-ethyl)-N-isopropylsulphonyl-p-phenylenediamine (156) N-(2-dimethylamino-ethyl)-N-butylsulphonyl-p-phenylenediamine (157) N-(2-dimethylamino-ethyl)-N-benzylsulphonyl-p-phenylenediamine (158) N-(2-dimethylamino-ethyl)-N-phenylsulphonyl-p-phenylenediamine (159) 4-((3-hydroxy-pyrrolidin-l-yl)-methyl)-aniline (160) 4-[N-(2-dimethylamino-ethyl)-N-(furan-2-carbonyl)- amino]-aniline (161) 4-[N-(2-dimethylamino-ethyl)-N-(2-methoxy-benzoyl)-amino]-aniline (162) 4-[N-(2-dimethylamino-ethyl)-N-(pyridine-3-carbonyl)-amino]-aniline (163) 4-[N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)-amino]-aniline .," (164) N-(piperidin-1-yl-methylcarbonyl)-N-methyl-p-phenylenediamine (165) N-(morpholin-4-yl-methylcarbonyl)-N-methyl-p-phenylenediamine (166) N- [ (4-benzyl-piperazin-l-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine (167) N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl-p-phenylenediamine (168) 4-(5-methyl-imidazol-4-yl)-aniline (169) N-[(2-dimethylamino-ethyl)-carbonyl]-N-isopropyl-p-phenylenediamine (170) N-[(2-dimethylamino-ethyl)-carbonyl]-N-benzyl-p-phenylenediamine (171) N-(N-aminocarbonylmethyl-N-methyl-amino)-methylcarbonyl)-N-methyl-p-phenylenediamine (172) N-[(N-benzyl-N-methyl-amino)-methylcarbonyl]-N-methyl-p-phenylenediamine (173) N-[di-(2-methoxyethyl)-amino-methylcarbonyl]-N-methyl-p-phenylenediamine (174) N- f (2- (4-tert.butoxycarbonyl-piperazin-1-yl)-ethyl)-carbonyl]-N-methyl-p-phenylenediamine (175) N-[(2-(piperidin-1-yl)-ethyl)-carbonyl]-N-methyl-p-phenylenediamine (176) N-[(2-(N-benzyl-N-methyl-amino)-ethyl)-carbonyl]-N-methyl-p-phenylenediamine (177) N-(dimethylaminomethylcarbonyl)-N-isopropyl-p-phenylenediamine (178) N-(piperidin-1-yl-methylcarbonyl)-N-isopropyl-p-phenylenediamine (179) N-[(4-tert.butoxycarbonyl-piperazin-1-yl)-methylcarbonyl]-N-isopropyl-p-phenylenediamine (180) N- [ (N-benzyl-N-methyl-amino) -methylcarbonyl]-N-benzyl-p-phenylenediamine (181) N-(dimethylaminomethylcarbonyl)-N-benzyl-p-phenylenediamine (182) N-(piperidin-1-yl-methylcarbonyl)-N-benzyl-p-phenylenediamine (183) 4-(1,2,4-triazol-l-yl-methyl)-aniline (184) 4-(1,2,3-triazol-2-yl-methyl)-aniline (185) 4-(1,2,3-triazol-l-yl-methyl)-aniline (186) 4-[(N-ethoxycarbonylmethyl-N-methyl-amino)-methyl]-aniline (187) 4-[(N-aminocarbonylmethyl-N-methyl-amino)-methyl]-aniline (188) 4-(azetidin-1-yl-methyl)-aniline (189) 4-[(di-(2-methoxy-ethyl)-amino)-methyl]-aniline (190) 4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]-aniline (191) 4-[N-(N-tert.butoxycarbonyl-3-amino-propyl)-N-methyl- aminomethyl]-aniline (192) 4-[(N-(methylcarbamoyl-methyl)-N-methyl-amino)-methyl]-aniline (193) 4-[(N-(dimethylcarbamoyl-methyl)-N-methyl-amino)-methyl]-aniline (194) 4-[(N-propyl-N-methyl-amino)-methyl] -aniline (195) 4-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)-methyl]- aniline (196) 4- [ (N-(3-dimethylamino-propyl)-N-methyl-amino)-methyl]-aniline (197) 4-[(N-(2-methoxy-ethyl)-N-methyl-amino)-methyl]-aniline (198) 4-[(N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl]-aniline (199) 4-[(N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl]-aniline (200) 4-(3-oxo-piperazin-l-yl-methyl)-aniline (201) N-[di-(2-hydroxyetttyl)-amino-methylcarbonyl]-N-methyl-p- phenylenediamine (202) N- [ (N- (2-methoxyethyl) -N-methyl-aiuino) -m.ethylcarban.Yll - N-methyl-p-phenylenediamine l (203) N-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)- methylcarbonyl]-N-methyl-p-phenylenediamine (204) N-[(4-methyl-piperazin-l-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine (205) N-[(imidazol-1-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine (206) N-[(phthalimido-2-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine Example XXI 4-(4-hvdroxvmethyl-piperidin-l-yl-methvl-amino)-aniline 1.1 g of 4-(4-ethoxycarbonyl-piperidin-l-yl-methyl-amino)-aniline are suspended in 15 ml of tetrahydrofuran. 175 mg of lithium borohydride are added at room temperature, stirred for 24 h, another 175 mg of lithium borohydride are added and after a further 7.5 hours 15 ml of water are added and the mixture is stirred for 10 minutes. It is extracted three times with 15 ml of ethyl acetate. The combined organic phases are washed with water and saturated saline solution, dried over sodium sulphate and concentrated by rotary evaporation. The residue is purified over a silica gel column with methylene chloride/methanol/ammonia 4:1:0.01 as eluant. Yield: 20 0 mg (2 7 % of theory) Rf value: 0.4 (silica gel, methylene chloride/methanol/ammonia 4:1:0.01) Melting point: 157°C Example XXII methyl 4-methoxycarbonylmethyl-3-nitro-benzoate 54.3 g of methyl 3-nitro-benzoate and 29.0 g of methyl chloroacetate are dissolved in 10 0 ml of dimethylformamide and this solution is added dropwise at -10°C to a solution of 78.5 g of potassium-tert. butoxide in 500 ml of dimethylformamide. The mixture is stirred for another 10 minutes at room temperature and after this time the solution is poured onto 350 ml of concentrated hydrochloric acid in 2 1 of ice water. The solution is stirred for 0.5 hours, the precipitate obtained is suction filtered and washed with water. The product is recrystallised from 150 ml of methanol and dried at 4 0°C in vacuo. Yield: 48.3 g of (51 % of theory), contains about 20 % of methyl 6-methoxycarbonylmethyl-3-nitro-benzoate Rf value: 0.7 (silica gel, petroleum ether/ethyl acetate = 1:1) Melting point: 65-73 °C The following compound is prepared analogously to Example XXII: (1) ethyl 4-methoxycarbonylmethyl-3-nitro-benzoate Prepared from ethyl 4-thoxycarbonylmethyl-3-nitro-benzoate Example XXIII methyl 2-indolinone-6-carboxylate 4 8.3 g of methyl 4-methoxycarbonylmethyl-3-nitro-benzoate are dissolved in 800 ml of concentrated acetic acid, 5.0 g of palladium on carbon (10%) are added and the solution is hydrogenated for 2.5 hours at room temperature and 5 0 psi. The catalyst is filtered off and the filtrate is evaporated down. The residue is taken up in 150 ml of tert.-butylmethyl ether, filtered again and dried in vacuo at 100°C. Yield: 28.6 g (98 % of theory), R£ value: 0.4 (silica gel, methylene chloride/methanol = 10:1) Melting point: 208-211 °C The following compound is prepared analogously to Example XXIII: (1) ethyl 2-indolinone-6-carboxylate Prepared from ethyl 4-methoxycarbonylmethyl-3-nitro-benzoate Example XXIV 1-acetyl-3-(l-ethoxy-1-phenylmethylene)-6-ethoxycarbonyl- 2-indolinone 15.0 g of ethyl 2-indolinone-6-carboxylate, 49.6 ml of triethyl orthobenzoate and 150 ml of acetic anhydride are stirred for 4 hours at 110°C. After this time the solvent is removed, the residue is recrystallised from petroleum ether and dried in vacuo at 50°C. Yield: 16.9 g (61 % of theory), Rf value: 0.5 (silica gel, petroleum ether/methylene chloride/ethyl acetate =5:4:1) Melting point: 98-100°C C22H21N05 The following compounds are prepared analogously to Example XXIV: (1) 1-acetyl-3-(l-ethoxy-1-phenylmethylene)-6-methoxycarbonyl-2-indolinone Preparation of the final compounds: Example 1 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene!- 6-carbamoyl-2-indolinone-trifluoroacetate 300 mg of resin obtained according to Example II are suspended in 3 ml of dimethylformamide and shaken with 0.2 g of 4- (piperidin-1-yl-methyl)-aniline for 22 hours at 70°C. Then it is filtered off and the resin is washed several times with methylene chloride, methanol and dimethylformamide. Then 1 ml of methanolic ammonia is added for 2 hours in order to eliminate the acetyl group. Then after further washing 4 ml of 10% trifluoroacetic acid in methylene chloride are added during another 60 minutes, the resin is separated off and the solution is evaporated down. Yield: 69 mg Rf value: 0.1 (silica gel, methylene chloride/methanol = 9:1) C2eH28N402 Mass spectrum: m/z = 452 (m+) The following compounds are prepared analogously to Example 1: (1) 3-Z-(1-Anilino-l-phenyl-methylene)-6-carbamoyl-2- indolinone Prepared from the resin obtained according to Example II and aniline C22H17N302 Mass spectrum: m/z = 355 (m+) (2) 3-Z-[1-(4-dimethylaminomethyl-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-dimethylaminomethyl-aniline C25H24N402 Mass spectrum: m/z = 412 (m+) (3) 3-Z-[1-(4-(2-diethylamino-ethyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-(2-diethylamino-ethyl)-aniline C28H30N4O2 Mass spectrum: m/z = 454 (m+) (4) 3-Z-[1-(4-(morpholin-4-yl-methyl)-anilino)-1-phenyl- methylene]-6 -carbamoyl-2 -indolinone-1ri fluoroacetate Prepared from the resin obtained according to Example II and 4-(morpholin-4-yl-methyl)-aniline Rf value: 0.50 (silica gel, methylene chloride/methanol = 4:1) C27H26N403 Mass spectrum: m/z = 454 (m+) (5) 3-Z- [1-(4-(l-oxo-thiomorpholin-4-yl-methyl)-anilino)- 1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-(l-oxo-thiomorpholin-4-yl-methyl)-aniline Rf value: 0.3 0 (silica gel, methylene chloride/methanol = 9:1) C27H26N403S Mass spectrum: m/z = 486 (m+) (6) 3-Z-[l-(4-(l,l-dioxo-thiomorpholin-4-yl-methyl)-anilino)- 1-phenyl-methylene]-6 -carbamoyl-2 -indolinone-tri fluoroacetate Prepared from the resin obtained according to Example II and 4-(1,l-dioxo-thiomorpholin-4-yl-methyl)-aniline Rf value: 0.30 (silica gel, methylene chloride/methanol = 9:1) C27H26N404S Mass spectrum: m/z = 502 (m+) (7) 3-Z-[1-(4-(benzylaminomethyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-[N-(phenyl-methyl)-N-tert.butoxycarbonyl-aminomethyl]- aniline Rf value: 0.40 (silica gel, methylene chloride/methanol =4:1) C30H26N4O2 Mass spectrum: m/z = 474 (m+) (8) 3-Z- [1-(4-(amino-methyl)-anilino)-1-phenyl-methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate Prepared f rom the resin obtained according to Example II and 4-(N-tert.butoxycarbonyl-aminomethyl)-aniline Rf value: 0.10 (silica gel, methylene chloride/methanol =4:1) C23H20N4O2 Mass spectrum: m/z = 384 (m+) (9) 3-Z- [1-(4-(2,6-dimethylpiperidin-l-yl-methyl)-anilino)- 1-phenyl-methylene]- 6-ca^bamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-(2,6-dimethylpiperidin-i-yl-methyl)-aniline Rf value: 0.45 (silica gel, methylene chloride/methanol =4:1) C30H32N4O2 Mass spectrum: m/z = 480 (m+) (10) 3-Z-[1-(4-(pyrrolidin-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2 -indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-(pyrrolidin-l-yl-methyl)-aniline Rf value: 0.15 (silica gel, methylene chloride/methanol =4:1) ^"27-"-26-"-"4^2 Mass spectrum: m/z = 438 (m+) (11) 3-Z- [1-(3-(dimethylaminomethyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 3-dimethylaminomethyl-aniline Rf value: 0.23 (silica gel, methylene chloride/methanol =4:1) C25H24N403 Mass spectrum: m/z = 412 (m+) (12) 3-Z-[1-(3-(N-methyl-N-ethyl-aminomethyl)-anilino)- 1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 3- (N-methyl-N-ethyl-aminomethyl)-aniline Rf value: 0.23 (silica gel, methylene chloride/methanol = 4:1) C26H26N402 Mass spectrum: m/z .= 426 (m+) (13) 3-Z-[1-(3-(methylaminomethyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-(N-tert.butoxycarbonyl-N-methyl-aminomethyl)-aniline Rf value: 0.06 (silica gel, methylene chloride/methanol =4:1) C24H22N402 Mass spectrum: m/z = 399 (m+H+) (14)- 3-Z- [1- (3-hydroxymethyl-anilino) -1-phenyl-methylene] - 6 -carbamoyl-2 -indolinone Prepared from the resin obtained according to Example II and 3-amino-benzyl alcohol Rf value: 0.7 (silica gel, methylene chloride/methanol =4:1) C23H19N303 Mass spectrum: m/z = 385 (m+) (15) 3-Z- [1- (4- (methoxycarbonylmethyl-aminomethyl) -anilino) - 1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4- (N-methoxycarbonylmethyl-N-tert.butoxycarbonyl-aminomethyl) - aniline Rf value: 0.4 0 (silica gel, methylene chloride/methanol = 9:1) C26H24N404 Mass spectrum: m/z = 457 (m+H+) (16) 3-Z-[1-(4-(N-methylsulphonyl-N-(dimethylaminocarbonyl- methyl)-amino)-anilino)-1-phenyl-methylene]-6-carbamoyl- 2-indolinone Prepared from the resin obtained according to Example II and 4-(N-methylsulphonyl-N-(dimethylaminocarbonylmethyl)-amino) - aniline Rf value: 0.40 (silica gel/ methylene chloride/methanol = 9:1) C27H27N505S Mass spectrum: m/z - 533 (m+) (17) 3-Z-[1-(4-(N-acetyl-aminomethyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone Prepared from the resin obtained according to Example II and 4-(N-acetyl-aminomethyl)-aniline R£ value: 0.70 (silica gel, methylene chloride/methanol = 4:1) C2SH22N403 Mass spectrum: m/z = 426 (m+) (18) 3-Z-[1-(3,4-dimethoxy-anilino)-1-phenyl-methylene]- 6 -carbamoyl-2 -indolinone Prepared from the resin obtained according to Example II and 3,4-dimethoxy-aniline Rf value: 0.40 (silica gel, methylene chloride/methanol = 9:1) C24H21N304 Mass spectrum: m/z = 415 (m+) (19) 3-Z-[1-(4-(morpholin-4-yl)-anilino)-1-phenyl-methylene]- 6 -carbamoyl-2 -indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-morpholin-4-yl-aniline Rf value: 0.2 0 (silica gel, methylene chloride/methanol = 9:1) C26H24N403 Mass spectrum: m/z = 440 (m+) (20) 3-Z-[1-(4-acetylamino-anilino)-1-phenyl-methylene]- 6-carbamoyl-2 -indolinone Prepared from the resin obtained according to Example II and 4 -acetylamino-aniline Rf value: 0.25 (silica gel, methylene chloride/methanol = 9:1) C24H20N4O3 Mass spectrum: m/z = 412 (m+) (21) 3-Z- [1-(4-amino-anilino)-1-phenyl-methylene]-6-carbamoyl- 2-indolinone Prepared from the resin obtained according to Example II and 4-amino-aniline Rf value: 0.40 (silica gel, methylene chloride/methanol = 9:1) C22H18N402 Mass spectrum: m/z = 370 (m+) (22) 3-Z-[1-(4-N-methyl-N-acetyl-amino-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone Prepared from the resin obtained according to Example II and 4-(N-methyl-N-acetyl-amino)-aniline Mass spectrum: m/z = 426 (m+) (23) 3-Z-[1-(4-ethoxycarbonyl-anilino)-1-phenyl-methylene]- 6-carbamoyl-2 -indolinone Prepared from the resin obtained according to Example II and ethyl 4-amino-benzoate C25H21N304 Mass spectrum: m/z = 427 (m+) (24) 3-Z-[1-(4-carboxy-anilino)-1-phenyl-methylene]- 6 -carbamoyl-2 -indolinone Prepared from the resin obtained according to Example II and 4-amino-benzoic acid Rf value: 0.11 (silica gel, methylene chloride/methanol = 9:1) C23H17N304 Mass spectrum: m/z = 398 (m-H+) (25) 3-Z-[1-(4-benzylcarbamoyl-anilino)-1-phenyl-methylene]- 6 -carbamoyl- 2 -indolinone Prepared from the resin obtained according to Example II and 4-amino-benzoic acid-benzylamide R£ value: 0.21 (silica gel, methylene chloride/methanol = 9:1) C30H24N4O3 Mass spectrum: m/z = 488 (m+) (26) 3-Z-[1-(cyclohexyl-amino)-1-phenyl-methylene]-6- carbamoyl-2-indolinone Prepared from the resin obtained according to Example II and cyclohexylamine Rf value: 0.60 (silica gel, methylene chloride/methanol = 9:1) C22H23N302 Mass spectrum: m/z = 361 (m+) (27) 3-Z-[1-(4-amino-cyclohexyl-amino)-1-phenyl-methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-amino-cyclohexylamine C22H24N402 Mass spectrum: m/z = 376 (m+) (28) 3-Z-[1-(N-methyl-piperidine-4-yl-amino)-1-phenyl- methylene] -6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 4-amino-1-methyl-piperidine Rf value: 0.15 (silica gel, methylene chloride/methanol =4:1) C22H24N402 Mass spectrum: m/z = 376 (m+) (29) 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-methyl- methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example 11(2) and 4-(piperidin-1-yl-methyl)-aniline Rf value: 0.3 0 (silica gel, methylene chloride/methanol = 4:1) C23H2SN402 Mass spectrum: m/z = 390 (m+) (30) 3-Z-[1-(3-dimethylaminomethyl-anilino)-1-methyl- methylene]-6-carbamoyl-2 -indolinone-trifluoroacetate Prepared from the resin obtained according to Example 11(2) and 3-dimethylaminomethyl-aniline Rf value: 0.51 (silica gel, methylene chloride/methanol = 4:1) C H N O " Mass spectrum: m/z = 351 (m+H+) (31) 3-Z-[1-(4-(N-methyl-N-benzyl-aminomethyl)-anilino)- 1-methyl-methylene]-6 -carbamoyl-2 -indolinone-trifluoroacetate Prepared from the resin obtained according to Example 11(2) and 4-(N-methyl-N-benzyl-aminomethyl)-aniline Rf value: 0.73 (silica gel, methylene chloride/methanol = 4:1) C26H26N402 Mass spectrum: m/z = 426 (m+) (32) 3-Z-[1-(4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)- amino)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone- trifluoroacetate Prepared from the resin obtained according to Example 11(2) and 4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)-amino)- aniline C22H27N504S Mass spectrum: m/z = 458 (m+H+) (33) 3-Z- [1-(4-chloro-anilino)-1-methyl-methylene]-6- carbamoyl-2 -indolinone Prepared from the resin obtained according to Example 11(2) and 4-chloro-aniline Rf value: 0.10 (silica gel, methylene chloride/methanol = 9:1) C17H14C1N302 Mass spectrum: m/z = 327/329 (m+) (34) 3-Z-[1-(3-chloro-anilino)-1-methyl-methylene]-6- carbamoyl-2 -indolinone Prepared from the resin obtained according to Example 11(2) and 3-chloro-aniline Rf value: 0.11 (silica gel, methylene chloride/methanol = 9:1) C17H14C1N302 Mass spectrum: m/z = 327/329 (m+) (35) 3-Z-[1-(4-methoxycarbonyl-anilino)-1-methyl-methylene]- 6 -carbamoyl-2-indolinone Prepared from the resin obtained according to Example 11(2) and methyl 4-amino-benzoate Rf value: 0.11 (silica gel, methylene chloride/methanol = 9:1) C19H17N304 Mass spectrum: m/z = 351 (m+) (36) 3-Z-[1-(4-carboxy-anilino)-1-methyl-methylene]-6- carbamoyl-2 -indolinone Prepared from the resin obtained according to Example 11(2) and 4-amino-benzoic acid C18H15N304 Mass spectrum: m/z = 336 (m-H+) (37) 3-Z-[1-(4-methyl-3-nitro-anilino)-1-methyl-methylene]- 6-carbamoyl-2-indolinone Prepared from the resin obtained according to Example 11(2) and 4-methyl-3-nitro-aniline R£ value: 0.82 (silica gel, methylene chloride/methanol =4:1) C1BH16N404 Mass spectrum: m/z = 352 (m+) (38) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-propyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example 11(4) and 4-(piperidin-1-yl-methyl)-aniline Rf value: 0.37 (silica gel, methylene chloride/methanol =4:1) C2SH30N4O2 Mass spectrum: m/z = 418 (m+) (39) 3-Z-[1-(3-dimethylaminomethyl-anilino)-1-propyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example 11(4) and 3-dimethylaminomethyl-aniline R£ value: 0.42 (silica gel, methylene chloride/methanol =4:1) C22H26N402 Mass spectrum: m/z = 3 78 (m+) (40) 3-Z-[1-(4-(N-methyl-N-benzyl-aminomethyl)-anilino)-1-pro- pyl-methylene]-6-carbamoyl-2 -indolinone-trifluoroacetate Prepared from the resin obtained according to Example 11(4) and 4-(N-methyl-N-benzyl-aminomethyl)-aniline Rf value: 0.81 (silica gel, methylene chloride/methanol =4:1) C28H3oN402 Mass spectrum: m/z = 454 (m+) (41) 3-Z- [1-(4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)- amino)-anilino)-1-propyl-methylene]-6-carbamoyl-2-indolinone- trif luoroace tat e Prepared from the resin obtained according to Example 11(4) and 4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)-amino)- aniline Rf value: 0.59 (silica gel, methylene chloride/methanol = 4:1) C24H31Ns04S Mass spectrum: m/z = 486 (m+H+) (42) 3-Z-[1-(4-chloro-anilino)-1-propyl-methylene]-6- carbamoyl-2 -indolinone Prepared from the resin obtained according to Example 11(4) and 4-chloro-aniline Rf value: 0.17 (silica gel, methylene chloride/methanol = 9:1) C19H18C1N302 Mass spectrum: m/z = 355/357 (m+) (43) 3-Z-[1-(3-chloro-anilino)-1-propyl-methylene]-6- carbamoyl- 2 -indolinone Prepared from the resin obtained according to Example 11(4) and 3-chloro-aniline Rf value: 0.12" (silica gel, methylene chloride/methanol = 9:1) C19H18C1N302 Mass spectrum: m/z = 355/357 (m+) (44) 3-Z-[1-(4-methoxycarbonyl-anilino)-1-propyl-methylene]- 6 -carbamoyl-2 -indolinone Prepared from the resin obtained according to Example 11(4) and methyl 4-amino-benzoate " Rf value: 0.8 (silica gel, methylene chloride/methanol = 4:1) C21H21N304 Mass spectrum: m/z = 379 (m+) (45) 3-Z-[1-(4-carboxy-anilino)-1-propyl-methylene]- 6 -carbamoyl-2 -indolinone Prepared from the resin obtained according to Example 11(4) and 4-amino-benzoic acid C20H19N3O4 Mass spectrum: m/z = 364 (m-H+) (46) 3-Z-[1-(4-methyl-3-nitro-anilino)-1-propyl-methylene]- 6 -carbamoyl-2 -indolinone Prepared from the resin obtained according to Example 11(4) and 4-methyl-3-nitro-aniline Rf value: 0.86 (silica gel, methylene chloride/methanol = 4:1) C30H20N4O4 Mass spectrum: m/z = 380 (m+) Example 2 3-Z-[1-(3-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate 2.0 g of resin obtained according to Example II are reacted analogously to Example 1 with 2.0 g of 3-aminobenzyl alcohol in 20 ml of dimethylformamide for 22 hours at 70°C. Then the solvent is suction filtered and the resin is washed several times with dimethylformamide and methylene chloride. Then 200 mg of the moist charged resin are suspended in 2 ml of methylene chloride and left to stand with 0.2 ml of methanesulphonic acid chloride and 0.1 ml of triethylamine for 2 hours at room temperature. Then the resin is washed several times with methylene chloride, suspended in 2 ml of methylene chloride and combined with 0.2 ml of piperidine. After 1 hour the resin is washed with methylene chloride and dimethylformamide and then treated with trifluoroacetic acid analogously to Example 1. Yield: 15 mg Rf value: 0.3 0 (silica gel, methylene chloride/methanol = 4:1) C28H28N402 Mass spectrum: m/z = 452 (m+) The following compounds are prepared analogously to Example 2: (1) 3-Z-[1-(3-(diethylaminomethyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and diethylamine Rf value: 0.80 (silica gel, methylene chloride/methanol =4:1) C27H28N402 Mass spectrum: m/z = 440 (m+) (2) 3-Z-[1-(3-(benzylaminomethyl)-anilino)-1-phenyl- methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and benzylamine Rf value: 0.80 (silica gel, methylene chloride/methanol =4:1) C30H26N4O2 Mass spectrum: m/z = 474 (m+) (3) 3-Z- [1- (3- (N-methyl-N-benzyl-atninomethyl) -anilino) - 1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and N-methyl-benzylamine Rf value: 0.80 (silica gel, methylene chloride/methanol =4:1) C31H28N402 Mass spectrum: m/z = 488 (m+) (4) 3-2- [1-(3-(butylaminomethyl)-anilino)-1-phenyl-methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and butylamine Rf value: 0.40 (silica gel, methylene chloride/methanol =4:1) C27H28N402 Mass spectrum: m/z = 440 (m+) (5) 3-Z-[l-(3-(aminomethyl)-anilino)-1-phenyl-methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and ammonia C23H20N402 Mass spectrum: m/z = 3 85 (m+H+) (6) 3-Z- [1-(3-(N-(3-dimethylaminopropyl)-N-methyl-amino¬ methyl) -anilino)-1-phenyl-methylene]- 6-carbamoyl^-indolinone- trifluoroacetate Prepared from the resin obtained according to Example II and l-dimethylamino-3-methylaminopropane Rf value: 0.67 (silica gel, methylene chloride/methanol =4:1) C2gH33N502 Mass spectrum: m/z = 484 (m+H+) (7) 3-Z-[1-(3-(N-(2-dimethylaminoethyl)-N-methyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate Prepared from the resin obtained according to Example II and 1-dimethylamino-2-methylaminoethane Rf value: 0.4 0 (silica gel, methylene chloride/methanol = 4:1) Mass spectrum: m/z = 470 (m+H+) Example 3 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene] -6-ethoxycarbonvl-2-indolinone ____ 1.5 g of l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 1.1 g of 4-(piperidin-1-yl- methyl)-aniline are dissolved in 15 ml of dimethylformamide and stirred for 45 minutes at 100°C. After cooling 5.0 ml of piperidine are added and the mixture is stirred for another 3 hours at room temperature. The solvent is removed and the residue purified over an aluminium oxide column (activity: 2-3) with methylene chloride/ethanol (100:3) as eluant. Yield: 1.1 g (58% of theory), Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol = 100:3) C30H31N3O3 Mass spectrum: m/z = 481 [M+] The following compounds are prepared analogously to Example 3: (1) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-ethoxycarbonyl-2-indolinone and 4-bromoaniline Rf value: 0.4 (silica gel, toluene/ethyl acetate = 5:1) C24Hx3BrN203 Mass spectrum: m/z = 462/464 [M+] (2) 3-Z-[1-(3-(dimethylaminomethyl) -anilino)-1-phenyl- methylene]-6 -ethoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 3-(dimethylaminomethyl)- aniline Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol = 30:1) C27H27N303 ESI mass spectrum: m/z = 442 [M+H+] (3) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene) -6~ ethoxycarbonyl-2-indolinone and 4-(dimethylaminomethyl)- aniline R£ value: 0.7 (aluminium oxide, ethyl acetate/ethanol = 20:1) C27H27N303 ESI mass spectrum: m/z = 442 [M+H+] (4) 3-Z- [1- (4- [ (2,6-dimethyl-piperidin-l-yl)-methyl]-anilino) 1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from- l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-[ (2 , 6-dimethyl-piperidin-l- yl) -methyl]-aniline Rf value: 0.6 (silica gel, methylene chloride/ethanol = 5:1) C32H35N303 Mass spectrum: m/z = 509 [M+] (5) 3-Z- [1-(4-(2-dimethylamino-ethyl)-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-ethoxycarbonyl-2-indolinone and 4-(2-dimethylamino-ethyl)-aniline Rf value: 0.2 (silica gel, methylene chloride/ethanol =5:1) C28H29N303 Mass spectrum: m/z = 455 [M+] (6) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(l-ethoxy-1-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-acetyl-amino)-aniline Rf value: 0.4 (aluminium oxide, methylene chloride/ethanol = 20:1) C30H32N4O4 Mass spectrum: m/z = 512 [M+] (7) 3-Z-[1-(4-tert.butyloxycarbonyl-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4 -tert.butyloxycarbonyl- aniline Rf value: 0.4 (aluminium oxide, methylene chloride/ethanol = 4 0:1) Mass spectrum: m/z = 484 [M+] (8) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N-(3-dimethylamino-propyl)- N-acetyl-amino)-aniline RBvalue: 0.2 (aluminium oxide, methylene chloride/ethanol = 4C:1) C11H34N404 Mass spectrum: m/z = 526 [M+] (N-(2-dimethylamino-ethyl)-N-methylsulphonyl-)-1-phenyl-methylene]-6-ethoxycarbonyl-2- l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- -2-indolinone and N-(2-dimethylamino-ethyl)-N- 1-p-phenylenediamine (aluminium oxide, methylene chloride/ethanol = m/z = 548 [M+] -(4-methyl-piperazin-l-yl)-anilino)-1-phenyl-thoxycarbonyl-2 -indolinone 1-acetyl-3-(1-ethoxy-l-phenylmethylene)-6--2-indolinone and 4-(4-methyl-piperazin-l-yl)- aluminium oxide, ethyl acetate) rum: m/z = 483 [M+H+] -(N-(2-dimethylamino-ethyl)-N-methyl-amino)-lyl-methylene]- 6-ethoxycarbonyl-2 -indolinone L-acetyl-3-(1-ethoxy-l-phenylmethylene)-6--2-indolinone and 4-(N-(2-dimethylamino-ethyl)-i-aniline aluminium oxide, methylene chloride/ethanol = :um: m/z = 485 [M+H+] - (N-(3-dimethylamino-propyl)-N-methyl-amino)-lyl-methylene]-6-ethoxycarbonyl-2-indolinone L-acetyl-3-(1-ethoxy-l-phenylmethylene)-6--2-indolinone and 4-(N-(3-dimethylamino-propyl)--aniline aluminium oxide, ethyl acetate) (9) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- methylsulphonyl-p-phenylenediamine R£ value: 0.3 (aluminium oxide, methylene chloride/ethanol = 40:1) C29H32N405S Mass spectrum: m/z = 548 [M+] (10) 3-Z-[1-(4-(4-methyl-piperazin-l-yl)-anilino)-l-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(4-methyl-piperazin-l-yl)- aniline Rf value: 0.3 (aluminium oxide, ethyl acetate) C29H30N4O3 ESI mass spectrum: m/z = 483 [M+H+] (11) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-methyl-amino)-aniline Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol = 20:1) C29H32N403 ESI mass spectrum: m/z = 485 [M+H+] (12) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N-(3-dimethylamino-propyl)- N-methyl-amino)-aniline Rf value: 0.5 (aluminium oxide, ethyl acetate) C30H34N4O3 ESI mass spectrum: m/z = 499 [M+H+] (13) 3-Z- [1-(4-(N-methyl-acetylamino)-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-amino-N-methyl-acetanilide Rf value: 0.3 (silica gel, methylene chloride/ethanol = 15:1) C27H25N304 Mass spectrum: m/z = 455 [M+] (14) 3-Z- [1-(4-(N-methyl-methylsulphonylamino)-anilino)-1- phenyl-methylene]-6-e thoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and N-(4-aminophenyl)-N-methyl- methanesulphonamide Rf value: 0.8 (aluminium oxide, ethyl acetate) C26H25N305S Mass spectrum: m/z ■= 491 [M+] (15) 3-Z- [1- (4-(N- (3-dimethylamino-propyl)-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and N-(3-dimethylamino-propyl)-N- methylsulphonyl-p-phenylenediamine Rf value: 0.6 (silica gel, methylene chloride/ethanol/ammonia =5:2:0.01) C30H34N4O5S ESI mass spectrum: m/z = 563 [M+H+] (16) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N- methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N- dimethylaminocarbonylmethyl-N-methylsulphonyl)-amino)-aniline Rf value: 0.6 (silica gel, methylene chloride/ethanol = 10:1) C29H30N4O6S ESI mass spectrum: m/z = 561 [M-H~] (17) 3-Z-[1-(4-(imidazol-4-yl)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl- 2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(imidazol-4-yl)-aniline Rr value: 0.5 (silica gel, methylene chloride/ethanol/ammonia = 10:1:0.01) C27H22N403 Mass spectrum: m/z = 450 [M+] (18) 3-Z-[1-(4-(tetrazol-5-yl)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(tetrazol-5-yl)-aniline Rf value: 0.5 (silica gel, methylene chloride/ethanol = 5:1) C25H20N6O3 ESI mass spectrum: m/z = 451 [M-JT] (19) 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)-anilino)-1- phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N-benzyl-N-methyl- aminomethyl) -aniline Rf value: 0.4 (silica gel, methylene chloride/ethanol = 10:1) C33H31N303 ESI mass spectrum: m/z = 516 [M-H~] (20) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propionyl-amino)- aniline)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2 -indol inone and 4- [N- (2-dimeth.ylamino-ethyl) - N-propionyl-amino]-aniline Rf value: 0.2 (silica gel, methylene chloride/ethanol = 5:1) C31H34N404 ESI mass spectrum: m/z = 525 [M-H~] (21) 3-Z-[1-(4-(pyrrolidin-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(pyrrolidin-1-yl-methyl)- aniline Rf value: 0.1 (silica gel, methylene chloride/ethanol = 5:1) C29H29N303 ESI mass spectrum: m/z = 466 [M-H"] (22) 3-Z-[1-(4-(N-methyl-N-phenethyl-aminomethyl)-anilino)-1- phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N-phenethyl-N-methyl- aminomethyl)-aniline Rf value: 0.4 (silica gel, methylene chloride/ethanol = 10:1) C34H33N3O3 ESI mass spectrum: m/z = 530 [M-H"] (23) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and N-dimethylaminomethylcarbonyl- N-methyl-p-phenylenediamine Rf value: 0.1 (silica gel, methylene chloride/ethanol = 10:1) C23H30N4O4 ESI mass spectrum: m/z = 497 [M-H"] (24) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-ethylsulphonyl- amino)-andlino)-l-phenyl-methylene]-6-ethoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- ethylsulphonyl-p-phenylenediamine Rf value: 0.6 (silica gel, methylene chloride/ethanol = 5:1) C30H34N4O5S ESI mass spectrum: rh/z = 561 [M-H"] (25) 3-Z-[1-(4-(N-tert.butoxycarbonyl-N-ethyl-aminomethyl)- anilino)-l-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and 4-(N-tert.butoxycarbonyl-N- ethyl-aminomethyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C32H35N3Os ESI mass spectrum: m/z = 54 0 [M-H"] (26) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-ethyl- methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-ethyl-methylene)-6- ethoxycarbonyl-2-indolinone and 4-(piperidin-1-yl-methyl)- aniline Rf value: 0.9 (silica gel, methylene chloride/ethanol = 5:1) C26H31N303 ESI mass spectrum: m/z = 432 [M-H"] (27) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl- amino)-anilino)-1-ethyl-methylene]-6-ethoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-ethyl-methylene)-6- ethoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- methylsulphonyl-p-phenylenediamine Rf value: 0.3 (silica gel, methylene chloride/ethanol = 5:1) C2SH32N405S ESI mass spectrum: m/z = 499 [M-H~] (28) 3-2-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(dimethylaminomethyl)- aniline R£ value: 0.6 (silica gel, methylene chloride/methanol = 5:1) C26H2SN303 ESI mass spectrum: m/z = 428 [M+H+] (29) 3-Z-[1-(4-[(2,6-dimethyl-piperidin-l-yl)-methyl]- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)~6- methoxycarbonyl-2-indolinone and 4-[(2,6-dimethyl-piperidin-l- yl) -methyl]-aniline Rf value: 0.5 (RP 8, methanol/five percent saline solution = 4:1) C31H33N303 ESI mass spectrum: m/z = 4 96 [M+H+] (30) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-ti¬me thyl sulphonyl -p-phenylenediamine Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1) C28H30N4O5S ESI mass spectrum: m/z = 533 [M-H~] (31) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(3-dimethylamino-propyl)-N- methylsulphonyl-p-phenylenediamine Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 30:1) C29H32N405S ESI mass spectrum: m/z = 547 [M-H~] (32) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N- methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-dimethylaminocarbonyl¬methyl -N-methylsulphonyl) -amino)-aniline Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C28H28N4OsS ESI mass spectrum: m/z = 547 [M-IT] (33) 3-Z-[1-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-acetyl-N- dimethylaminocarbonylmethyl)-amino)-aniline R£ value: 0.6 (silica gel, methylene chloride/methanol = 10:1) C29H28N4Os ESI mass spectrum: m/z = 511 [M-H~] (34) 3-Z- [1-(4- (N-dimethylaminocarbonylmethyl-amino)-anilino)- 1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-dimethylaminocarbonyl¬methyl) -amino)-aniline Rf value: 0.6 (aluminium oxide, methylene chloride/methanol = 30:1) C27H26N404 ESI mass spectrum: m/z = 469 [M-H"] (35) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(3-dimethylamino-propyl)-N- acetyl-p-phenylenediamine Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C30H33N4O4 ESI mass spectrum: m/z = 511 [M-H"] (36) 3-Z-[1-(4-(N-methylaminocarbonylmethyl-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-methylaminocarbonylmethyl- N-methylsulphonyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C27H26N406S ESI mass spectrum: m/z = 533 [M-H"] (37) 3-Z-[l-(4-((imidazolidin-2,4-dion-5-ylidene)-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((imidazolidin-2,4-dion-5- ylidene)-methyl)-aniline Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C27H20N4O5 ESI mass spectrum: m/z = 479 [M-H"] (38) 3-Z- [1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl- amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-((2-dimethylamino-ethyl)- carbonyl)-N-methyl-p-phenylenediamine Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C29H30N4O4 ESI mass spectrum: m/z = 497 [M-H"] (39) 3-Z-[l-(4-(N-tert.butoxycarbonyl-aminomethyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-tert.butoxycarbonyl-aminomethyl) -aniline Rf value: 0.3 (aluminium oxide, methylene chloride/methanol = 20:1) C25H29N305 ESI mass spectrum: m/z = 498 [M-H"] (40) 3-Z-[1-(4-(2-oxo-pyrrolidin-l-yl-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(2-oxo-pyrrolidin-l-yl- methyl) -aniline Rf value: 0.3 (silica gel, methylene chloride/methanol = 20:1) C28H2SN304 ESI mass spectrum: m/z = 466 [M-H"] (41) 3-Z-[l-(4-(N-aminocarbonylmethyl-N-methy1sulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-aminocarbonylmethyl-N- methylsulphonyl-p-phenylenediamine Rf value: 0.7 (silica gel, methylene chloride/methanol = 5:1) C26H24N406S ESI mass spectrum: m/z = 519 [M-H"] (42) 3-Z-[1-(4-(thiomorpholin-4-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(thiomorpholin-4-yl- methyl)-aniline Rf value: 0.4 (silica gel, methylene chloride/methanol = 15:1) C28H27N303S ESI mass spectrum: jh/z = 484 [M-H~] (43) 3-Z-.[l- (4- (1, l-dioxo-thiomorpholin-4-yl-methyl) -anilino) - 1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(1,l-dioxo-thiomorpholin-4- yl-methyl)-aniline Rf value-. 0.5 (silica gel, methylene chloride/methanol = 10:1) C2BH27N305S ESI mass spectrum: m/z = 516 [M-H~] (44) 3-2- [1- (4- (N-cyanomethyl-N-methylsulphonyl-amino)- anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-cyanomethyl-N-methyl- sulphonyl-p-phenylenediamine Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1) C2SH22N405S ESI mass spectrum: m/z = 501 [M-H"] (45) 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylaminomethyl)- anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-ethyl-N- tert.butoxycarbonyl-aminomethyl)-aniline Rf value: 0.6 (silica gel, methylene chloride/methanol =10:1) C31H33N305 ESI mass spectrum: m/z = 526 [M-H"] (46) 3-Z- [1-(4-(N-benzyl-N-raethyl-aminomethyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-benzyl-N-methyl- aminomethyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C32H29N303 ESI mass spectrum: rti/z = 502 [M-H"] (47) 3-Z- [1-(4-(l-oxo-thiomorpholin-4-yl-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(l~ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(l-oxo-thiomorpholin-4-yl- methyl)-aniline R£ value: 0.7 (silica gel, methylene chloride/methanol = 10:1) C28H27N304S ESI mass spectrum: m/z = 500 [M-H"] (48) 3-Z- [1-(4-(2-(imidazol-4-yl)-ethyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(2-(imidazol-4-yl)-ethyl)- aniline Rf value: 0.4 (silica gel, methylene chloride/methanol = 5:1) C2aH24N403 ESI mass spectrum: m/z = 463 [M-H"] (49) 3-Z-[1-(4-(morpholin-4-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(morpholin-4-yl-methyl)- aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C28H27N304 ESI mass spectrum: m/z = 468 [M-H"] (50) 3-Z-[1-(4-((4-methyl-piperazin-l-yl)-methyl)-anilino)-1- phenyl -methylene] - 6 -methoxycarbonyl"- 2 - indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((4-methyl-piperazin-l-yl) - methyl)-aniline Rf value: 0.4 (silica gel, methylene chloride/methanol 5:1) C29H30N4O3 ESI mass spectrum: m/z = 481 [M-H~] (51) 3-Z- [1- (4- ( (2-(N-benzyl-N-methyl-amino) -ethyl)-N- methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(2-(N-benzyl-N-methyl-amino) -ethyl)-N-methylsulphonyl-amino)-aniline Rf value: 0.7 (silica gel, methylene chloride/methanol = 10:1) C34H34N405S ESI mass spectrum: m/z = 609 [M-H"] (52) 3-Z- [1-(4-cyclohexylamino-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-cyclohexyl-p-phenylenediamine Rf value: 0.8 (silica gel, methylene chloride/methanol = 10:1) ESI mass spectrum: m/z = 451 [M-H"] (53) 3-Z-[1-(4-(pyridin-4-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(pyridin-4-yl-methyl)- aniline Rf value: 0.6 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C29H23N303 ESI mass spectrum: m/z = 460 [M-H"] (54) 3-Z- [1- (4-(imidazol-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(imidazol-1-yl-methyl)- aniline Rf value: 0.4 (silica gel, methylene chloride/methanol/ammonia = 10:1:0.01) C27H22N403 ESI mass spectrum: m/z = 449 [M-H"] (55) 3-Z- [1-(4-(imidazol-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(imidazol-1-yl-methyl)- aniline Rf value: 0.4 (silica gel, methylene chloride/methanol/ammonia =10:1:0.01) C27H22N403 ESI mass spectrum: m/z = 449 [M-H"] (56) 3-Z-[1-(N-methyl-piperidine-4-yl-amino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-amino-1-methyl-piperidine Rf value: 0.3 (silica gel, methylene chloride/methanol = 5:1) C23H25N303 ESI mass spectrum: m/z = 3 90 [M-H"] (57) 3-Z- [1-(4-(imidazol-4-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(imidazol-4-yl-methyl)-aniline Rf value: 0.2 (silica gel, methylene chloride/methanol = 5:1) C27H22N403 ESI mass spectrum: m/z = 449 [M-H~] (58) 3-Z-[1-(4-((4-hydroxy-piperidin-l-yl)-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((4-hydroxy-piperidin-l-yl) -methyl)-aniline/ Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1) C29H29N303 ESI mass spectrum: m/z = 482 [M-JT] (59) 3-Z-[1-(4-((4-methoxy-piperidin-l-yl)-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((4-methoxy-piperidin-l-yl) -methyl)-aniline Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C30H31N3O4 ESI mass spectrum: m/z = 496 [M-H"] (60) 3-Z-[1-(4-benzyl-anilino)-1-phenyl-methylene]-6-methoxy- carbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-benzyl-aniline Rf value: 0.6 (silica gel, methylene chloride/methanol - 10:1) C30H24N2O3 Melting point: 224°C (61) 3-Z-[1-(4-(N-(3-trifluoroacetylamino-propyl)-N- methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-(3-trifluoroacetylamino-propyl) -N-methylsulphonyl-p-phenylenediamine Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C29H27F3N406S ESI mass spectrum: m/z = 615 [M-H"] (62) 3-Z- [1-(4-tert.butoxycarbonylmethyl-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- ethoxycarbonyl-2-indolinone and tert.butyl 4- aminophenylacetate Rr value: 0.5 (aluminium oxide, ethyl acetate) C30H30N2O5 ESI mass spectrum: m/z = 497 [M-H"] (63) 3-Z- [1-(4-tert.butoxycarbonyl-anilino)-1-ethyl- methylene]-6-ethoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-ethylmethylen)-6- ethoxycarbonyl-2-indolinone" and 4-tert.butoxycarbonyl-aniline R£ value: 0.4 (aluminium oxide, methylene chloride/ethanol = 20:1) C25H28N205 ESI mass spectrum: m/z = 435 [M-H"] (64) 3-Z- [1- (4- (4-tert.butoxycarbonyl-piperazin-1-yl-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(4-tert.butoxycarbonyl- piperazin-1-yl-methyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C33H36N405 ESI mass spectrum: m/z = 567 [M-H"] (65) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(1-methyl-imidazol-2-yl)- aniline Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1) C27H22N403 ESI mass spectrum: m/z = 449 [M-H"] (66) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl- amino)-3-nitro-anilino)-l-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 6-(N-(2-dimethylamino-ethyl)- N-methylsulphonyl-amino)-3-amino-nitrobenzene Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1) C28H29Ns07S ESI mass spectrum: m/z = 578 [M-H"] (67) 3-2-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl- amino) -3-amino-anilino)-l-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-methylsulphonyl-amino)-3 -amino-ani1ine Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C28H31N505S ESI mass spectrum: m/z = 548 [M-H"] (68) 3-Z-[1-(4-((3-(N-benzyl-N-methyl-amino)-propyl)-N-methyl¬ sulphonyl-amino) -anilino)-l-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(3-(N-benzyl-N-methyl- amino)-propyl)-N-methylsulphonyl-amino)-aniline Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1) C3SH36N405S ESI mass spectrum: m/z = 623 [M-JT] (69) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl- amino)-3-chloro-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-methylsulphonyl-amino)-3-chloro-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C28H29C1N40SS ESI mass spectrum: m/z = 567/569 [M-H"] (70) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N- dimethylaminomethylcarbonyl-N-methyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C28H28N404 ESI mass spectrum: m/z = 483 [M-H"] (71) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-acetyl-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C29H30N4O4 ESI mass spectrum: m/z = 497 [M-H"] (72) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propionyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-propionyl-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H32N4O4 ESI mass spectrum: m/z = 511 [M-H"] (73) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-butyryl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-butyryl-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C31H34N404 ESI mass spectrum: m/z = 525 [M-H"] (74) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-isobutyryl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-isobutyryl-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C31H34N404 ESI mass spectrum: m/z = 525 [M-H"] (75) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzoyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-benzoyl-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C34H32N404 ESI mass spectrum: m/z = 559 [M-H"] (76) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3- amino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-amino-aniline R£ value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C29H31Ns04 ESI mass spectrum: m/z = 512 [M-H~] (77) 3-Z-[1-(4-(4-hydroxymethyl-piperidin-l-yl-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(4-hydroxymethyl-piperidin- 1-yl-methyl-amino)-aniline Rf value: 0.3 (silica gel, methylene chloride/methanol = 5:1) C30H31N3O4 ESI mass spectrum.: m/z = 496 [M-H~] (78) 3-Z-[1-(4-(2-(4-hydroxy-piperidin-l-yl)-ethyl)-anilino)- 1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(2-(4-hydroxy-piperidin-l- yl) -ethyl-amino) -aniline Rf value: 0.3 (silica gel, methylene chloride/methanol =5:1) C30H31N3O4 ESI mass spectrum: m/z = 496 [M-H~] (79) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- propylsulphonyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H34N4O5S ESI mass spectrum: m/z = 561 [M-H~] (80) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-butylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- butylsulphonyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C31H36N405S ESI mass spectrum: m/z = 575 [M-H"] (81) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-phenylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- phenylsulphonyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C33H32N4OsS ESI mass spectrum: m/z = 595 [M-H"] (82) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- benzylsulphonyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C34H3«N4OsS ESI mass spectrum: m/z = 609 [M-H"] (83) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-ethylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N- ethylsulphonyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C29H32N405S ESI mass spectrum: m/z = 547 [M-H"] (84) 3-Z-[1-(4-((imidazolidin-2, 4-dion-5-yl)-methyl)-anilino)- 1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((imidazolidin-2,4-dion-5- yl)-methyl)-aniline Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1} C27H22N405 ESI mass spectrum: jh/z = 481 [M-H~] (85) 3-Z- [1-(4-((3-hydroxy-pyrrolidin-l-yl)-methyl)-anilino)- 1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6- methoxycarbony1-2-indolinone and 4-((3-hydroxy-pyrrolidin-l-yl) -methyl)-aniline Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1) C28H27N304 ESI mass spectrum: m/z = 468 [M-H"] (86) 3-Z- [1-(4-(cyclohexylyl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(cyclohexyl-methyl)-aniline (Eur. J. Med. Chem. Chim. Ther. 1992, 27, 537-544) Rj. value: 0.6 (silica gel, methylene chloride/methanol = 10:1) C30H30N2O3 ESI mass spectrum: m/z = 465 [M-H~] (87) 3-Z- [1-(4-(cyclohexyl-carbonyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(cyclohexyl-carbonyl)- aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C30H28N3O4 ESI mass spectrum: m/z = 479 [M-H"] (88) 3-Z-[1-(4-diethylaminomethyl-anilino)-1-phenyl- methylene]- 6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(l~ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(diethylamino-methyl)- aniline Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C28H29N303 ESI mass spectrum: rti/z = 454 [M-H~] (89) 3-Z-[1-(4-(N-(n-hexyl)-N-methyl-aminomethyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(n-hexyl)-N-methyl-aminomethyl) -aniline Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1) C31H35N303 ESI mass spectrum: m/z = 496 [M-H~]. (90) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(furan-2- carbonyl)-amino)-anilino)-1-phenyl-methylene] -6- methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbony1-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-(furan-2-carbonyl)-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C32H30N4O5 ESI mass spectrum: m/z = 549 [M-H~] (91) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(2-methoxy- benzoyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxy- carbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-N-(2-methoxy-benzoyl)-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C35H34N405 ESI mass spectrum: m/z = 589 [M-H"] (92) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(pyridine-3- carbonyl)-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl) - N-(pyridine-3-carbonyl)-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C33H31Ns04 ESI mass spectrum: m/z = 560 [M-H"] (93) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-(phenyl-acetyl)-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C35H34N404 ESI mass spectrum: m/z = 573 [M-H"] (94) 3-Z-[1-(4-(N-ethyl-N-methyl-aminomethyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-ethyl-N-methyl- aminomethyl) -aniline Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1) C27H27N303 ESI mass spectrum: m/z = 440 [M-H"] (95) 3-Z- [1-(4-(imidazol-2-yl)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(imidazol-2-yl)-aniline R£ value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C26H20N4O3 ESI mass spectrum: m/z = 435 [M-H"] (96) 3-Z-[1-(4-(l-ethyl-imidazol-2-yl)-anilino)-l-phenyl- methylene]- 6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(i-ethyl-imidazol-2-yl)- aniline ." R£ value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C23H24N403 ESI mass spectrum: m/z = 463 [M-H"] (97) 3-Z-[1-(4-(l-benzyl-imidazol-2-yl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(l-benzyl-imidazol-2-yl)- aniline Rf value: 0.3 (silica gel, methylene chloride/methanol = 20:1) C33H26N403 ESI mass spectrum: m/z = 525 [M-H"] (98) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N- isopropylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N- (2-d.imethylamino-ethyl) -N- isopropylsulphonyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H34N4OsS ESI mass spectrum: m/z = 561 [M-H"] (99) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N-methyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(piperidin-1-yl- methylcarbonyl)-N-methyl-p-phenylenediamine R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C31H32N404 ESI mass spectrum: m/z = 523 [M-H~] (100) 3-Z- [1-(4-(N-(morpholin-4-yl-methylcarbonyl)-N-methyl- amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(morpholin-4-yl- methylcarbonyl)-N-methyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H30N4Os ESI mass spectrum: m/z = 525 [M-H~] (101) 3-Z- [1-(4-(N-((4-benzyl-piperazin-l-yl)-methylcarbonyl) - N-methyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbony1-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-((4-benzyl-piperazin-l-yl) - methylcarbonyl)-N-methyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C37H37N504 ESI mass spectrum: m/z = 614 [M-H~] (102) 3-Z- [1-(4-(N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl- amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(pyrrolidin-1-yl- methylcarbonyl)-N-methyl-p-phenylenediamine R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C3oH3oN404 ESI mass spectrum: m/z = 509 [M-H~] (103) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3- bromo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)- N-acetyl-amino)-3-bromo-aniline Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1) C29H29BrN404 ESI mass spectrum: m/z = 575/577 [M-H~] (104) 3-Z-[1-(4-(5-methyl-imidazol-4-yl)-anilino)-1-phenyl- methylene] -6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(5-methyl-imidazol-4-yl)- aniline Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia =10:1:0.01) C27H22N403 ESI mass spectrum: m/z = 449 [M-H~] (105) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N- isopropyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-((2-dimethylamino-ethyl)- carbonyl)-N-isopropyl-p-phenylenediamine Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1) C31H34N404 ESI mass spectrum: m/z = 525 [M-H"] (106) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N- benzyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl- 2-indolinone Prepared from 1-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-((2-dimethylamino-ethyl)- carbonyl)-N-benzyl-p-phenylenediamine Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1) C31H34N404 ESI mass spectrum: m/z"= 525 [M-H"] (107) 3-Z-[1-(4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-butyl-N- tert.butoxycarbonyl-aminomethyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C33H37N305 ESI mass spectrum: m/z = 554 [M-H] (108) 3-Z-[1-(4-(N-((N-aminocarbonylmethyl-N-methyl-amino)- methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(N-aminocarbonylmethyl-N- methyl-amino)-methylcarbonyl)-N-methyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C29H29NsOs ESI mass spectrum: m/z = 526 [M-H"] (109) 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl)- N-methyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-((N-benzyl-N-methyl-amino)- methylcarbonyl)-N-methyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C34H32N404 ESI mass spectrum: m/z = 559 [M-H"] (110) 3-Z- [1- (4-(N-(di-(2-methoxyethyl)-amino-methylcarbonyl)- N-methyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-(di-(2-methoxyethyl)-amino-methylcarbonyl )-N-methyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C32H36N406 ESI mass spectrum: m/z = 571 [M-H"] (111) 3-Z-[1-(4-(N-((2-(4-tert.butoxycarbonyl-piperazin-1-yl)- ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-((2-(4-tert.butoxycarbonyl- piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-p-phenylenediamine Rf value: 0.8 (silica gel, methylene chloride/methanol = 5:1) C36H41N506 ESI mass spectrum: m/z = 638 [M-H"] (112) 3-Z- [1- (4- (N- ( (2- (piperidin-1-yl) -ethyl).-carbonyl) -N- methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N~((2-(piperidin-1-yl)- ethyl)-carbonyl)-N-methyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 5:1) C32H34N404 ESI mass spectrum: m/z = 537 [M-H"] (113) 3-Z- [1- (4- (N-((2-(N-benzyl-N-methyl-amino)-ethyl)- carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-((2-(N-benzyl-N-methyl-amino) -ethyl)-carbonyl)-N-methyl-p-phenylenediamine Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C35H34N404 ESI mass spectrum: m/z = 573 [M-H"J (114) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-isopropyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N- (dimethylaminomethylcarbonyl)-N-isopropyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H32N4O4 ESI mass spectrum: m/z = 511 [M-H~] (115) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N- isopropyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(piperidin-1-yl- methylcarbonyl)-N-isopropyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C33H36N404 ESI mass spectrum: m/z = 551 [M-H"] (116) 3-Z-[1-(4-(N-((4-tert.butoxycarbonyl-piperazin-1-yl)- methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl- methylene] - 6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-((4-tert.butoxycarbonyl- piperazin-1-yl)-methylcarbonyl)-N-isopropyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C37H43N506 ESI mass spectrum: m/z = 652 [M-H"] (117) 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl) -N-benzyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-((N-benzyl-N-methyl-amino) -methylcarbonyl)-N-benzyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C40H36N4O4 ESI mass spectrum: m/z = 635 [M-H"] (118) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-benzyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and N-(dimethylaminomethyl- carbonyl)-N-benzyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C34H32N404 ESI mass spectrum: m/z = 559 [M-H"] (119) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N-benzyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(5-methyl-imidazol-4-yl)- aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) L.37ri36JN4U4 ESI mass spectrum: m/z = 559 [M-H"] (120) 3-Z-[1-(4-(l,2,4-triazol-2-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(1,2,4-triazol-l-yl-methyl)-aniline , R£ value: 0.5 (silica gel, methylene chloride/methanol = 10 .-1) C26H21N503 ESI mass spectrum: m/z = 450 [M-H~] (121) 3-Z- [1-(4-(1,2,3-triazol-2-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl~2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(1,2,3-triazol~2-yl- methyl)-aniline Rr value: 0.5 (silica gel, methylene chloride/methanol = 20:1) C„H21N503 ESI mass spectrum: m/z = 450 [M-H"] (122) 3-Z- [1- (4-(1,2,3-triazol-l-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(1,2,3-triazol-l-yl-methyl) -aniline Rf value: 0.4 (silica gel, methylene chloride/methanol - 9:1) C26H21N503 ESI mass spectrum: m/z = 450 [M-H~] (123) 3-Z-[1-(4-((N-aminocarbonylmethyl-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((N-aminocarbonylmethyl-N- methyl-amino)-methyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C27H26N404 ESI mass spectrum: m/z = 469 [M-H"] (124) 3-Z-[1-(4-((di-(2-methoxy-ethyl)-amino)-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((di-(2-methoxy-ethyl)- amino)-methyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H33N3O5 ESI mass spectrum: m/z = 514 [M-H"] (125) 3-Z-[1-(4-(pyrrolidin-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(pyrrolidin-1-yl-methyl)- aniline , Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C28H27N303 ESI mass spectrum: m/z = 452 [M-H"] (126) 3-Z- [1-(4-((di-(2-hydroxy-ethyl)-amino)-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2~indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((di-(2-hydroxy-ethyl)- amino)-methyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C28H23N305 ESI mass spectrum: m/z = 486 [M-H"] (127) 3-Z-[1-(4-((N-ethoxycarbonylmethyl-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((N-ethoxycarbonylmethyl-N-methyl-amino)-methyl)-aniline Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol = 40:1) C29H29N305 ESI mass spectrum: m/z = 498 [M-H"] (128) 3-Z-[1-(4-(azetidin-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(azetidin-1-yl-methyl)- aniline R£ value: 0.5 (silica gel, methylene chloride/methanol/ammonia = 9:1:0.5) C27H2SN303 ESI mass spectrum: m/z = 438 [M-H~] (129) 3-Z-[1-(4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)- anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(N-propyl-N- tert .butoxycarbonyl-aminomethyl)-aniline Rf value.- 0.5 (silica gel, methylene chloride/methanol = 9:1) C32H3SN305 ESI mass spectrum: m/z - 540 [M-H"] (130) 3-Z-[1-(4((N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl- amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((N-(2-(2-methoxy-ethoxy)- ethyl)-N-methyl-amino)-methyl)-aniline Rf value: 0.4 (silica gel, methylene chloride/methanol = 9:1) C30H33N3O5 ESI mass spectrum: m/z = 514 [M-H"] (131) 3-Z- [1- (4- ( (N- (tert.butoxycarbonyl-3-amino-propyl)-N- methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-methoxy¬ carbonyl -2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6 - methoxycarbonyl-2-indolinone and 4-(N-(N-tert.butoxycarbonyl- 3-amino-propyl)-N-methyl-aminomethyl)-aniline R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C33H38N405 ESI mass spectrum: m/z = 571 [M+H+] (132) 3-Z- [1-(4-( (N-(methylcarbamoyl-methyl)-N-methyl-amino) - methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((N-(methylcarbamoyl- methyl)-N-methyl-amino)-methyl)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9.-1) C28H28N404 ESI mass spectrum: m/z *= 483 [M-H"] (133) 3-Z- [1-(4-((N-(dimethylcarbamoyl-methyl)-N-methyl- amino) -methyl) -anilino) -1 -phenyl-methylene] -6-methoxycarbonyl- 2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((N-(dimethylcarbamoyl- methyl)-N-methyl-amino)-methyl)-aniline Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1) C29H30N4O4 ESI mass spectrum: m/z = 497 [M-H"] (134) 3-Z- [1-(4-methyl-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-methyl-aniline Rf value: 0.4 (silica gel, methylene chloride/methanol = 9:1) C24H20N2O3 ESI mass spectrum: m/z - 383 [M-H"] (135) 3-Z- [1-(4-((N-propyl-N-methyl-amino)-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((N-propyl-N-methyl-amino)- methyl)-aniline R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C28H29N303 ESI mass spectrum: m/z = 454 [M-H"] (136) 3-Z-[1-(4-((N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((N-(2-hydroxy-ethyl)-N- methyl-amino)-methyl)-aniline Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol = 40:1) C27H27N304 ESI mass spectrum: m/z = 456 [M-H"] (137) 3-Z-[1-(4-((N-(2-dimethylamino-ethyl)-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((N-(2-dimethylamino-ethyl) -N-methyl-amino)-methyl)-aniline Rf value: 0."5 (silica gel, methylene chloride/methanol = 9:1) C29H32N403 ESI mass spectrum: m/z = 483 [M-H"] (138) 3-Z-[1-(4-((N-(3-dimethylamino-propyl)-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-((N-(3-dimethylamino- propyl)-N-methyl-amino)-methyl)-aniline aniline R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H34N4O3 ESI mass spectrum: m/z = 497 [M-H"] (139) 3-Z-[1-(4-(3-oxo-piperazin-l-yl-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6- methoxycarbonyl-2-indolinone and 4-(3-oxo-piperazin-1-yl- methyl)-aniline aniline R£ value: 0.46 (silica gel, methylene chloride/methanol = 9:1) C28H26N404 ESI mass spectrum: m/z = 481 [M-H~] Example 4 3-Z-[1-(4-carboxy-anilino)-1-phenyl-methylene]-6-ethoxy- carbonyl-2 -indolinone 485 mg of 3-Z- [1-(4-tert.butoxycarbonyl-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone are dissolved in 15 ml of methylene chloride and 6.0 ml of trifluoroacetic acid are added. The mixture is stirred for 2 hours at room temperature. Then the solvent is removed and the residue recrystallised from ether. Yield: 375 mg (87 % of theory), Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1) C25H20N2O5 Mass spectrum: m/z = 428 [M+] The following compounds are prepared analogously to Example 4 : (1) 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-aminomethyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C24H21N303 ESI mass spectrum: m/z = 398 [M-H"] (2) 3-Z- [1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylamino- methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone R£ value: 0.4 (silica gel, methylene chloride/methanol/ammonia = 10:1:0.01) C26H2SN303 ESI mass spectrum: m/z = 426 [M-H~] (3) 3-Z- [1-(4-carboxymethyl-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-tert.butoxycarbonylmethyl-anilino)-1- phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone Rf value: 0.1 (aluminium oxide, methylene chloride/ethanol/ammonia = 5:1:0.01) C26H22N2Os ESI mass spectrum: m/z = 441 [M-H~] (4) 3-Z-[1-(4-carboxy-anilino)-1-ethyl-methylene]-6-ethoxy- carbonyl-2 -indolinone Prepared from 3-Z-[1-(4-tert.butoxycarbonyl-anilino)-1-ethyl- methylene]-6-ethoxycarbonyl-2-indolinone Rf value: 0.1 (aluminium oxide, methylene chloride/ethanol = 20:1) ESI mass spectrum: m/z = 3 79 [M-H"] (5) 3-Z- [1-(4-(piperazin-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-(4-tert.butoxycarbonyl-piperazin-l-yl- methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2- indolinone Rf value: 0.1 (silica gel, methylene chloride/methanol/ammonia = 10:1:0.01) C28H28N403 ESI mass spectrum: m/z = 469 [M+H+] (6) 3-Z-[1-(4-butylaminomethyl-anilino) -1-phenyl-methylene]-6- methoxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-(N-butyl-N-tert.butoxycarbonyl- aminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C28H29N303 ESI mass spectrum: m/z = 454 [M-H~] (7) 3-Z-[1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone Prepared from 3-Z- [1-(4-(N-tert.butoxycarbonyl-N-ethyl- aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2- indolinone R£ value: 0.3 (silica gel, methylene chloride/methanol/ammonia = 10:1:0.01) C27H27N303 ESI mass spectrum: m/z = 442 [M+H+] (8) 3-Z-[1-(4-ethylaminomethyl-anilino) -1-phenyl-methylene]-6- carbamoyl-2-indolinone Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylamino- methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone R£ value: 0.2 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C2SH24N402 ESI mass spectrum: m/z = 411 [M-H"] (9) 3-Z-[1-(4-(N- (piperazin-1-yl-methylcarbonyl)-N-isopropyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from 3-Z- [1- (4-(N-((4-tert.butoxycarbonyl-piperazin-1-yl) -methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone Rf value: 0.35 (silica gel, methylene chloride/methanol = 9:1) C32H35Ns04 ESI mass spectrum: m/z = 552 [M-H~] (10) 3-Z-[1-(4-(N-((2-(piperazin-1-yl)-ethyl)-carbonyl)-N- methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone Prepared from 3-Z-[1-(4-(N-((2-(4-tert.butoxycarbonyl- piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1- phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone R£ value: 0.4 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C31H33N504 ESI mass spectrum: m/z = 540 [M+H+] (11) 3-Z-[1-(4-(N-propyl-aminomethyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl- 2 -indolinone Prepared from 3-Z-[1-(4-(N-propyl-N-tert.butoxycarbonyl- aminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Rf value: 0.35 (silica gel, methylene chloride/methanol = 9:1) C27H27N303 ESI mass spectrum: m/z = 440 [M-H~] (12) 3-Z-[1-(4-((N-(3-amino-propyl)-N-methyl-amino)-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-((N-(tert.butoxycarbonyl-3-amino- propyl) -N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Rf value: 0.3 5 (silica gel, methylene chloride/methanol = 9:1) C2aH30N4O3 ESI mass spectrum: m/z = 471 [M+H+] Example 5 3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene] -6- e thoxycarbonyl - 2 - indol inone " 100 mg of 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)-anilino)- 1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone are dissolved in 20 ml of ethanol, 0.2 ml of IN hydrochloric acid are added and the mixture is hydrogenated for 70 minutes at room temperature and 50 psi hydrogen pressure. The reaction solution is filtered and the filtrate concentrated by rotary evaporation. The residue is dried in vacuo at 100°C. Yield: 50 mg (53 % of theory), Rf value: 0.3 (silica gel, methylene chloride/ethanol/ammonia =5:1:0.01) C26H2SN303 ESI mass spectrum: m/z = 426 [M-H"] The following compounds are prepared analogously to Example 5: (1) 3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Prepared from 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone R£ value: 0.2 (silica gel, methylene chloride/methanol/ammonia = 10:1:0.01) C2SH23N303 ESI mass spectrum: m/z = 412 [M-H"] (2) 3-Z^[1-(4-(N-(2-methylamino-ethyl)-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from 3-Z-[1-(4-((2-(N-benzyl-N-methyl-amino)-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Rf value: 0.3 (silica gel, methylene chloride/methanol/ammonia = 10:1:0.01) C27H28N405S ESI mass spectrum: m/z = 519 [M-H"] (3) 3-Z- [1-(4-(N-(2-amino-ethyl)-N-methylsulphonyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-(N-cyanomethyl-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C26H26N4OsS ESI mass spectrum: m/z = 505 [M-H"] (4) 3-Z-[1-(4-(N-(3-methylamino-propyl)-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from 3-Z-[1-(4-(N-(3-(N-benzyl-N-methyl-amino)- propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Rf value: 0.3 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C28H30N4O5S ESI mass spectrum: m/z = 533 [M-H ] (5) 3-Z-[1-(4-(N-(piperazin-1-yl-methylcarbonyl)-N-methyl- amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from 3-Z-[1-(4-(N-((4-benzyl-piperazin-l-yl)- methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H31NsO4 ESI mass spectrum: m/z = 524 [M-H"] (6) 3-Z-[1-(4-(N-(methylamino-methylcarbonyl)-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)- methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Rf value: 0.3 (silica gel, methylene chloride/methanol = 9:1) C27H26N404 ESI mass spectrum: m/z = 469 [M-H~] (7) 3-Z-[1-(4-(N-((2-methylamino-ethyl)-carbonyl)-N-methyl- amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from 3-Z- [1- (4-(N-((2-(N-benzyl-N-methyl-amino)- ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone Rf value: 0.3 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C2BH28N404 ESI mass spectrum: m/z = 483 [M-H"] Example 6 3-Z-[1-(4-ureidomethyl-anilino)-1-phenyl-methylene]-6-methoxy- carbonvl-2 -indolinone 300 mg of 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone are dissolved in 15 ml of methanol and 200 ml of triethylamine are added. Then 4 00 mg of potassium cyanate in 5 ml of water are added. After 2 days of stirring at room temperature the reaction solution is concentrated by rotary evaporation, the residue taken up in methylene chloride and washed once with water and once with saturated sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated by rotary evaporation. The residue is dried in vacuo at 10 0°C. Yield: 100 mg of (21 % of theory), Rf value: 0.7 (silica gel, methylene chloride/methanol = 5:1) C25H22N404 ESI mass spectrum: m/z = 441 [M-H~] Example 7 3-Z-[1-(4-guanidinomethyl-anilino)-1-phenyl-methylene]-6- methoxycarbonvl-2 -indolinone 300 mg of 3-Z- [1- (4,-aminomethyl-anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone are dissolved in 5 ml of dimethylformamide and 300 ml of triethylamine are added. Then 700 mg of 3,5-dimethylpyrazol-l-carboxylic acid amidine in 5 ml of dimethylformamide are added. After one day of stirring at room temperature the reaction solution is concentrated by rotary evaporation. The residue is dried at 100°C in vacuo. Yield: 200 mg (87 % of theory), Rf value: 0.1 (Reversed phase RP 8, methanol/five percent saline solution = 6:4) ^25^23^03 Mass spectrum: m/z = 441 [M+] Example 8 3-Z-[1-(4-acetylaminomethyl-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone 100. mg of 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone are dissolved in 5 ml of glacial acetic acid, 0.1 ml of acetic anhydride is added and the mixture is stirred for 10 minutes at room temperature. After this time the reaction solution is poured onto saturated soda solution and extracted four times with methylene chloride. The combined organic phases are washed with saturated saline solution, dried over sodium sulphate and concentrated by rotary evaporation. The residue is dried at 100°C in vacuo. Yield: 20 mg (23 % of theory), Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C26H23N304 ESI mass spectrum: m/z = 440 [M-H"] The following compounds are prepared analogously to Example 8: (1) 3-Z-[1-(4-(N-methylsulphonyl-aminomethyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl- 2 -indolinone Prepared from 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone and methanesulphonyl chloride/triethylamine Rf value: 0.7 (silica gel, methylene chloride/methanol = 5:1) ESI mass spectrum: m/z = 476 [M-H"] (2) 3-Z-[1-(4-(4-benzoyl-piperazin-l-yl-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone Prepared from 3-Z- [1-(4-(piperazin-1-yl-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2-indolinone and benzoyl chloride Rf value: 0.7 (silica gel, methylene chloride/methanol = 10:1) C3SH32N404 ESI mass spectrum: m/z = 571 [M-H"] (3) 3-Z-[1-(4-((N-(3-acetylamino-propyl)-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2- indolinone Prepared from 3-Z-[1-(4-((N-(3-amino-propyl)-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2- indolinone Rf value: 0.3 (silica gel, methylene chloride/methanol = 9:1) C30H32N4O4 ESI mass spectrum: m/z = 511 [M-H ] Example 9 3-Z-[l-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene1-6-carboxy-2-indolinone 0.8 g of 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone are dissolved in 30 ml of ethanol, 8.3 ml of IN sodium hydroxide solution are added and the mixture is stirred for 1 hour at 8 0°C. After cooling, it is neutralised with 8.3 ml of IN hydrochloric acid. The precipitate formed is suction filtered, washed with water, ethanol and ether and dried in vacuo at 100°C. Yield: 0.7 g of (89 % of theory), RE value: 0.2 (silica gel, methylene chloride/methanol = 5:2) C28H27N303 Mass spectrum: m/z = 453 [M+] The following compounds are prepared analogously to Example 9: (1) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene] -6-carboxy- 2-indolinone Prepared from 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]- 6 -ethoxycarbony1-2-indolinone Rf value: 0.4 (silica gel, toluene/ethyl acetate = 5:1) C22H15BrN203 ESI mass spectrum: m/z = 43 5/43 7 [M+H+] (2) 3-Z-[1-(3-(dimethylaminomethyl)-anilino)-1-phenyl- methylene]-6-carboxy-2-indolinone Prepared from 3-Z-[1-(3-(dimethylaminomethyl)-anilino)- 1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone Rf value: 0.7 (Reversed phase RP 8, methanol/five percent saline solution =4:1) C25H23N303 ESI mass spectrum: m/z = 414 [M+H+] (3) 3-Z-[1-(4-(dimethylaminomethyl)-anilino) -1-phenyl- methylene]- 6-carboxy-2-indolinone Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)- 1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone Rf value: 0.7 (Reversed phase RP 8, methanol/five percent saline solution =4:1) C25H23N303 ESI mass spectrum: m/z = 412 [M-H"] (4) 3-Z-[1-(4- [ (2,6-dimethyl-piperidin-l-yl)-methyl]-anilino)- 1-phenyl-methylene]- 6-carboxy-2-indolinone Prepared from 3-Z-[1-(4-[ (2,6-dimethyl-piperidin-l-yl)- methyl] -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2- indolinone Rf value: 0.6 (Reversed phase RP 8, methanol/five percent saline solution = 4:1) C30H31N3O3 ESI mass spectrum: m/z = 482 [M+H+] (5) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl- methylene]- 6-carboxy-2 -indolinone Prepared from 3-Z- [1-(4-(l-methyl-imidazol-2-yl) -anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2-indolinone Rf value: 0.6 (Reversed phase RP 8, methanol/five percent saline solution =4:1) C26H20N4O3 ESI mass spectrum: m/z = 435 [M-H"] (6) 3-Z-[1-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)- anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone Prepared from 3-Z-[1-(4-(N-acetyl-N- dimethylaminocarbonylmethyl-amino) -anilino) -1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1) C28H26N405 ESI mass spectrum: m/z = 497 [M-H"] (7) 3-Z- [1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6- carboxy-2-indolinone Prepared from 3-Z-[1-(4-ethylaminomethyl-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone Rf value: 0.6 (Reversed phase RP 8, methanol/five percent saline solution = 4:1) C2SH23N303 ESI mass spectrum: m/z = 412 [M-H~] (8) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) - anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone Prepared from 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N- methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl- 2-indolinone Rf value: 0.6 (Reversed phase RP 8, methanol/five percent saline solution = 4:1) C27H26N404 ESI mass spectrum: m/z = 469 [M-H"] (9) 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylaminomethyl)- anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylamino¬ methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2- indolinone Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C30H31N3O5 ESI mass spectrum: m/z = 512 [M-H"] (10) 3-Z-[1-(4-((N-carboxymethyl-N-methyl-amino)-methyl)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-((N-ethoxycarbonylmethyl-N-methyl- amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl -2-indolinone Rf value: 0.4 (silica gel, methylene chloride/methanol =6:1) C27H25N305 ESI mass spectrum: m/z = 470 [M-H ] Example 10 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-methoxvcarbonyl-2 -indolinone 0.9 g of 3-Z- [1- (4-,"(piperidin-l-yl-methyl) -anilino) -l-phenyl-methylene]-6-carboxy-2-indolinone are suspended in 35 ml of dimethylformamide and 0.4 g of carbonyldiimidazole are added. The mixture is stirred for 14 hours at 80°C. After this time 2 0 ml of methanol are added and the mixture is stirred for another 3 hours at 50°C. The solvent is removed and the residue is purified over a silica gel column with methylene chloride/methanol (3:1) as eluant. Yield: 0.5 g of (49% of theory), RE value: 0.5 (aluminium oxide, methylene chloride/methanol = 3 0:1) C29H29N303 ESI mass spectrum: m/z = 468 [M+H+] The following compounds are prepared analogously to Example 10: (1) 3-Z-[1-(4-(piperidin-l-yl-methyl)-anilino)-1-phenyl- methylene]- 6-benzyloxycarbonyl-2 -indolinone Prepared from 3-Z- [1-(4-(piperidin-l-yl-methyl)-anilino)- 1-phenyl-methylene]-6-carboxy-2-indolinone and benzyl alcohol Rf value: 0.6 (aluminium oxide, methylene chloride/methanol = 30:1) C3SH33N303 Mass spectrum: m/z = 543 [M+] (2) 3-Z-[1-(4-(piperidin-l-yl-methyl)-anilino)-1-phenyl- methylene]-6-isopropyloxycarbonyl-2 -indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and isopropanol Rf value: 0.4 (aluminium oxide, methylene chloride/isopropanol = 30:1) Mass spectrum: m/z = 495 [M+] (3) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene] -6-propyloxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)- 1-phenyl-methylene]-6-carboxy-2-indolinone and n-propanol Rf value: 0.7 (silica gel, methylene chloride/methanol =" 5:1) C31H33N303 Mass spectrum: m/z = 495 [M+] (4) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene] -6-butyloxycarbonyl-2-indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)- 1-phenyl-methylene]-6-carboxy-2-indolinone and n-butanol Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C32H35N303 Mass spectrum: m/z = 509 [M+] (5) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-6-carbamoyl- 2 -indolinone Prepared from 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]- 6-carboxy-2-indolinone and ammonia Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1) C22H16BrN203 Mass spectrum: m/z = 432/434 [M-H~] (6) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene]-6-ethylcarbamoyl-2 -indolinone Prepared from 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and ethylamine gas Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1) C30H32N4O2 Mass spectrum: m/z = 480 [M+] (7) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl- methylene]-6-[(2-methoxy-ethoxy)-carbonyl]-2-indolinone Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)~ l-phenyl-methylene]-6-carboxy-2-indolinone and methylglycol Rf value: 0.8 (silica gel, methylene chloride/methanol = 4:1) C25H23N303 ESI mass spectrum: m/z = 470 [M-H"] (8) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl- methylene]-6-[(2-dimethylamino-ethoxy)-carbonyl]-2-indolinone Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)- l-phenyl-methylene]-6-carboxy-2-indolinone and 2-dimethylaminoethanol aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 5:2) C29H32N403 • ESI mass spectrum: m/z = 483 [M-JTJ (9) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl- methylene]-6-[(2-N-tert.butoxycarbonyl-amino-ethoxy)- carbonyl]-2-indolinone Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl-methylene]-6-carboxy-2-indolinone and 2-N-tert .butoxycarbonyl-amino-ethanol aniline Rf value: 0.8 (silica gel, methylene chloride/methanol = 5:2) C32H36N405 ESI mass spectrum: m/z = 412 [M-H"] (10) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl- methylene]-6-[(2,2,2-trifluoroethoxy)-carbonyl]-2-indolinone Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)- 1-phenyl-methylene]- 6-carboxy-2-indolinone and 2,2,2- trifluoroethanol aniline R£ value: 0.5 (silica gel, methylene chloride/methanol = 5:1) C27H24F3N303 ESI mass spectrum: m/z = 494 [M-H~] Example 11 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methvlene]-6-carbamoyl-2-indolinone 0.9 g of 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone, 0.8 g of TBTU and 0.4 g of HOBT are suspended in 25 ml of dimethylformamide and 1.0 ml of triethylamine are added. The mixture is stirred for 15 minutes at room temperature. After this time ammonia gas is introduced at 10-15°C over a period of 15 minutes and the mixture is stirred for 1.5 hours at room temperature. The precipitate formed is suction filtered, washed with water, ethanol and ether and dried at 10 0°C in vacuo. Yield: 0.6 g (64 % of theory), Rf value: 0.4 (Reversed phase RP 8, methanol/five percent saline solution = 6:4) C28H28N402 ESI mass spectrum: m/z = 453 [M+H+] The following compounds are prepared analogously to Example 11: (1) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-dimethylcarbamoyl-2-indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and dimethylamine hydrochloride/diisopropylethylamine R£ value: 0.5 (silica gel, methylene chloride/methanol = 5:1) C30H32N4O2 ESI mass spectrum: m/z = 481 [M+H+] (2) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene] -6-(N-ethyl-N-methyl-carbamoyl)-2-indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)- 1-phenyl-methylene]-6-carboxy-2-indolinone and N-ethyl- N-methyl-amine Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol = 20:1) C31H34N402 ESI mass spectrum: m/z = 495 [M+H+] (3) 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene] - 6-methylcarbamoyl-2-indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)- 1-phenyl-methylene]-6-carboxy-2-indolinone and methylamine hydrochloride/diisopropylethylamine Rf value: 0.3 (aluminium oxide, methylene chloride/ethanol = 20:1) C29H30N4O2 ESI mass spectrum: m/z = 467 [M+H+] (4) 3-Z-[1-(3-(dimethylaminomethyl)-anilino)-1-phenyl- methylene] -6-methylcarbamoyl-2-indolinone Prepared from 3-Z-[1-(3-(dimethylaminomethyl)-anilino)- 1-phenyl-methylene]-6-carboxyl-2-indolinone and methylamine hydrochloride/triethylamine Rf value: 0.3 (silica gel, methylene chloride/ethanol = 2:1) C26H26N402 Mass spectrum: m/z = 426 [M+] (5) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl- methylene] -6-(2-hydroxyethyl-carbamoyl)-2-indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)- 1-phenyl-methylene]- 6-carboxy-2-indolinone and ethanolamine/diisopropylethylamine Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C30H32N4O3 ESI mass spectrum: m/z = 4 95 [M-H~] (6) 3-Z- [1- (4- (pipe.ridin-1-yl-methyl) -anilino) -1-phenyl- methylene]-6-diethylcarbamoyl-2 -indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and diethylamine hydrochloride/diisopropylethylamine R£ value: 0.8 (aluminium oxide, methylene chloride/methanol = 10:1) C32H36N402 ESI mass spectrum: m/z = 509 [M+H+] (7) 3-Z-[IT(4-(N-tert.butoxycarbonyl-ethylaminomethyl)- anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl- ethylaminomethyl)-anilino)-1-phenyl-methylene]-6-carboxy-2- indolinone Rf value: 0.3 (silica gel, toluene/ethyl acetate/ethanol = 4:2:1) C30H32N4O4 ESI mass spectrum: m/z = 511 [M-H"] (8) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone Prepared from 3-Z-[1-(4-(N-dimethylaminomethylcarbohyl-N- methyl-amino)-anilino)-1-phenyl-methylene]-6-carboxy-2- indolinone Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) C27H27N503 ESI mass spectrum: m/z = 468 [M-H"] Example 12 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone x citric acid 3.25 g of citric acid monohydrate are placed in 50 ml of methanol and 5.0 g of 3-Z-[1-(4-(N-dimethylaminomethyl-carbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone are added at room temperature. The solution formed is evaporated down, the residue is washed with ether and recrystallised from ethyl acetate. Yield: 6.3 g (90 % of theory), Rf value: 0.6 (silica gel, methylene chloride/methanol/ammonia =5:1:0.01) Melting point: 198°C C28H28N4Os x C6H807 ESI mass spectrum: m/z = 483 [M-H"] Elemental analysis: calc: C 60.34 H 5.37 N 8.28 found: 59.98 5.25 8.13 The following compound is prepared analogously to Example 12: (1) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone x methanesulphonic acid Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone and methanesulphonic acid Rf value: 0.6 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) Melting point: 275°C C26H25N303 x CH403S ESI mass spectrum: m/z = 426 [M-H"] Elemental analysis: calc.: C 61.92 H 5.59 N 8.03 S 6.12 found: 61.43 5.87 7.85 5.39 The following compounds may be prepared analogously to the foregoing Examples: (1) 3-Z-(1-anilino-1-phenyl-methylene)-6-ethoxycarbonyl-2-indolinone (2) 3-Z-[1-(4-nitro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (3) 3-Z- [1-(4-fluoro-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone (4) 3-Z- [1-(4-chloro-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone (5) 3-Z-[1-(4-iodo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (6) 3-Z- [1-(4-cyano-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone (7) 3-Z-[1-(4-methoxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (8) 3-Z-[1-(4-ethoxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (9) 3-Z-[1-(4-trifluoromethyl-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2-indolinone (10) 3-Z-[1-(4-methyl-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (11) 3-Z-[1-(4-methylmercapto-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (12) 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (13) 3-Z-[1-(4-(isopropylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (14) 3-Z-[1-(4-(anilinomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (15) 3-Z-[1-(4-(propylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (16) 3-Z-[1-(4-(butylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (17) 3-Z-[1-(4-(isobutylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (18) 3-Z-[1-(4-(cyclohexylaminomethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (19) 3-Z-[1-(4-(benzylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (20) 3-Z-[1-(4-((N-ethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (21) 3-Z-[1-(4-((N-methyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (22) 3-Z-[1-(4-((N-isopropyl-N-methyl-amino)-methyl)-anilino) 1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone (23) 3-Z- [1-(4-((N-ethyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (24) 3-Z- [1-(4-((N-ethyl-N-isopropyl-amino)-methyl)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (25) 3-Z-[1-(4-(dipropylaminomethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (26) 3-Z- [1-(4-(diisopropylaminomethyl)-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone (27)" 3-Z-[1-(4-((N-benzyl-N-ethyl-amino)-methyl)-anilino)-1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone (28) 3-Z-[1-(4-(dibenzylaminomethyl)-anilino)-1-phenyl- methylene]-6-ethoxycarbony1-2 -indolinone (29) 3-Z- [1-(4-(3,6-dihydro-2H-pyridin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (30) 3-Z- [1-(4-(3,5-dimethyl-piperidin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (31) 3-Z-[1-(4-(azepan-1-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (32) 3-Z- [1-(4-(piperazin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (33) 3-Z- [1-(4-(morpholin-4-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (34) 3-Z- [1-(4-(thiomorpholin-4-yl-methyl)-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone (35) 3-Z-[1-(4-(l-oxo-thiomorpholin-4-yl-methyl)-anilino)- 1-phenyl-methylene]-6 -ethoxycarbonyl- 2 -indolinone (36) 3-Z- [1- (4- (1,l-dioxo-thiomorpholin-4-yl-methyl)-anilino)-1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone (37) 3-Z-[1-(4-(acetylamino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (38) 3-Z-[1-(4-(2-amino-ethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (39) 3-Z-[1-(4-(2-methylamino-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (40) 3-Z- [1- (4-.(2-ethylamino-ethyl) -anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (41) 3-Z-[1-(4-(2-diethylamino-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (42) 3-Z-[1-(4-(2-piperidin-l-yl-ethyl)-anilino)-1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone (43) 3-Z-[1-(4-(2-acetylamino-ethyl)-anilino)-l-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (44) 3-Z-[1-(4-(3-amino-propyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (45) 3-Z-[1-(4-(3-dimethylamino-propyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (46) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (47) 3-Z-[1-(4-(N-methylaminomethylcarbonyl-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl~2-indolinone (48) 3-Z- [1-(4-(N-ethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (49) 3-Z-11- (4- lE-diethylaminomethylcarbonyl-TSI-methyl-amino) anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (50) 3-Z- [1- (4- (N- (pipejridin-1-yl-methylca-rbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (51) 3-Z-[1-(4-(N-(morpholin-4-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (52) 3-Z- [1-(4-(N-(piperazin-1-yl-methylcarbonyl)-N-methyl-amino]-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl~2-indolinone (53) 3-Z-[1-(4-(N-(2-amino-ethylcarbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (54) 3-Z-[1-(4-(N-(2-methylamino-ethylcarbonyl)-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (55) 3-Z-[1-(4-(N-(2-diethylamino-ethylcarbonyl)-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (56) 3-Z-[1-(4-(N-acetyl-N-(2-aminoethyl) -amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (57) .3-Z-[1-(4-(N-acetyl-N-(2-methylamino-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (58) 3-Z-[1-(4-(N-acetyl-N-(2-methylamino-propyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (59) 3-Z-[1-(4-(N-acetyl-N-(2-piperidin-l-yl-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (60) 3-Z-[1-(4-(N-acetyl-N-(aminocarbonylmethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (61) 3-Z-[1-(4-(N-acetyl-N-(dimethylaminocarbonylmethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (62) 3-Z-[1-(4-(N-acetyl-N-(piperidin-1-yl-carbonylmethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (63) 3-Z-[1-(4-(N-methyl-N-(aminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (64) 3-Z-[1-(4-(N-methyl-N-(methylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (65) 3-Z-[l-(4-(N-methyl-N-(dimethylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (66) 3-Z-[1-(4-(N-methyl-N-(piperidin-1-yl-carbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (67) 3-Z-[1-(4-(N-(2-aminoethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (68) 3-Z-[1-(4-(N-(2-methylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (69) 3-Z-[1-(4-(N-(2-ethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (70) 3-Z-[1-(4-(N-(2-disthylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (71) 3-Z-[1-(4-(N-(2-pyrrolidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (72) 3-Z-[1-(4-(N-(2-piperidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (73) 3-Z-[1-(4-(N-(2-piperazin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (74) 3-Z-[1-(4-(N-(2-(morpholin-4-yl)-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (75) 3-Z-[l-(4-(N-(aminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (76) 3-Z-[1-(4-(N-(methylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (77) 3-Z-[1-(4-(N-(ethylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (78) 3-Z-[1-(4-(N-(N-(2-dimethylamino-ethyl)-N-methyl-amino)-carbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone (79) 3-Z-[l-(4-(N-(diethylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (80) 3-Z-[1-(4-(N-(pyrrolidin-1-yl-carbonylmethyl)-N-methyl¬ sulphonyl -amino) -anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (81) 3-Z-[1-(4-(N-(piperidin-1-yl-carbonylmethyl)-N- methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (82) 3-Z-[1-(4-(N-(piperazin-1-yl-carbonylmethyl)-N- methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (83) 3-Z- [1- (4- (N- ( (morpholin-4-yl)-carbonylmethyl)-N-methyl¬ sulphonyl-amino) -anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (84) 3-Z-[1-(4-(2-dimethylamino-ethoxy)-anilino)-1-phenyl- methylene] - 6-ethoxycarbonyl-2 -indolinone (85) 3-Z-[1-(4-(3-dimethylamino-propoxy)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2 -indolinone (86) 3-Z-[1-(4-(aminocarbonylmethyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (87) 3-Z-[1-(4-(2-aminocarbonyl-ethyl)-anilino)-1-phenyl- methylene]-6-ethoxycarbonyl-2-indolinone (88) 3-Z-[1-(4-(pyridin-2-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (89) 3-Z-[1-(4-(pyridine-3-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (90) 3-Z-[1-(4-(pyridin-4-yl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (91) 3-Z-[1-(4-(N-acetyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (92) 3-Z-[1-(4-(N-ethylcarbonyl-N-(dimethylaminocarbonyl-methyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (93) 3-Z-[1-(carbamoylmethyl-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (94) 3-Z-[1-(4-dimethylcarbamoylmethyl-anilino)-1-phenyl-methylene] -6 -ethoxycarbonyl-2 -indolinone (95) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-methylene]-6 -ethoxycarbonyl-2 -indolinone (96) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-propylidene]-6-ethoxycarbonyl-2 -indolinone (97) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-butylidene]-6-ethoxycarbonyl-2 -indolinone (98) 3-Z- [1- (4- (N- (3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-methylene]-6-ethoxycarbonyl-2-indolinone (99) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-ethylidene]-6-ethoxycarbonyl-2-indolinone (100) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-propylidene]-6-ethoxycarbonyl-2-indolinone (101) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone (102) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-methylene]-6-ethoxycarbonyl-2-indolinone (103) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-propylidene]-6-ethoxycarbonyl-2-indolinone (104) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone (105) 3-Z-[1-(4-tetrazol-5-yl-anilino)-methylene]-6-ethoxycarbonyl-2 -indolinone (106) 3-Z-[1-(4-tetrazol-5-yl-anilino)-ethylidene] -6-ethoxy-carbonyl-2 -indolinone (107) 3-Z- [1- (4-tetrazol-5-yl--anilino) -propylidene] -6-ethoxy-carbonyl-2 -indolinone (108) 3-Z-[1-(4-tetrazol-5-yl-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone (109) 3-Z-[1-(4-carboxy-anilino)-methylene] -6-ethoxycarbonyl-2-indolinone (110) 3-Z-[1-(4-carboxy-anilino)-propylidene]-6-ethoxycarbonyl-2 -indolinone (111) 3-Z- [1-(4-carboxy-anilino)-butylidene] -6-ethoxycarbonyl-2-indolinone (112) 3-Z- [1-(4-(N-(3-dimethylamino-propionyl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-l-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (113) 3-Z- [1-(4-(N-(4-dimethylamino-butyryl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (114) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(2-dimethylamino-ethylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (115) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(3-dimethylamino-propylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (116) 3-Z-[1-(4-((2-hydroxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (117) 3-Z-[1-(4-((2-methoxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (118) 3-Z-[1-(4-((2-dimethylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (119) 3-Z-[1-(4-((3-dimethylamino-propyl)-amino-methyl)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (120) 3-Z-[1-(4-((N-tert.butoxycarbonyl-2-amino-ethyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (121) 3-Z-[1-(4-((N-tert.butoxycarbonyl-3-amino-propyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (122) 3-Z- [1- (4- ( (2.-amino-ethyl) -amino-methyl) -anilino) -1-pheny1-methylene]-6-ethoxyc arbony1-2 -indo1inone (123) 3-Z-[1-(4-((3-amino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (124) 3-Z-[1-(4-((2-acetylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (125) 3-Z-[1-(4-((3-acetylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (126) 3-Z-[1-(4-((2-methylsulphonylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (127) 3-Z-[1-(4-((3-methylsulphonylamino-propyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (128) 3-Z-[1-(4-(N-(N-tert.butoxycarbonyl-2-amino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (129) 3-Z-[1-(4-(N-(2-amino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (130) 3-Z-[1-(4-(N-(2-acetylamino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (131) 3-Z-[1-(4-(N-(2-methylsulphonylamino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (132) 3-Z-[1-(4-(carboxymethyl-amino-methyl)-anilino)-1-phenyl-methylene-] -6-ethoxycarbonyl-2-indolinone (133) 3-Z-[1-(4-(ethoxycarbonylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (134) 3-Z-[1-(4-(carbamoylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (135) 3-Z-[1-(4-(dimethylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (136) 3-Z-[1-(4-(methylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (137) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-amino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (138) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-nitro-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (13 9) 3-Z-[l-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-acetylamino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (140) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methylsulphonylamino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (141) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-cyano-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (142) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-hydroxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (143) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methoxy-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2 -indolinone (144) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-ethoxycarbonyl~anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (145) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-carboxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (146) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-carbamoyl-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (147) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-chloro-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (148) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-fluoro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (149) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-bromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (150) 3-Z- [1- (4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (151) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (152) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3,5-dibromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (153) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3,5-dichloro-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (154) 3-Z- [1-(4-(dimethylaminomethyl)-3-amino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (155) 3-Z- [1-(4-(dimethylaminomethyl)-3-nitro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (156) 3-Z- [1-(4-(dimethylaminomethyl)-3-acetylamino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (157) 3-Z-[1-(4-(dimethylaminomethyl)-3-(methylsulphonylamino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (158) 3-Z- [1-(4-(dimethylaminomethyl)-3-cyano-anilino)-1- phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (159) 3-Z-[1-(4-(dimethylaminomethyl)-3-hydroxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (160) 3-Z-[1-(4-(dimethylaminomethyl)-3-methoxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (161) 3-Z-[1-(4-(dimethylaminomethyl)-3-(ethoxycarbonyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (162) 3-Z-[1-(4-(dimethylaminomethyl)-3-carboxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (163) 3-Z-[1-(4-(dimethylaminomethyl)-3-carbamoyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (164) 3-Z-[1-(4-(dimethylaminomethyl)-3-chloro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (165) 3-Z-[1-(4-(dimethylaminomethyl)-3-fluoro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (166) 3-Z-[1-(4-(dimethylaminomethyl)-3-bromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (167) 3-Z-[1-(4-(dimethylaminomethyl)-3-methyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (168) 3-Z-[1-(4-(dimethylaminomethyl)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (169) 3-Z-[1-(4-(dimethylaminomethyl)-3,5-dibromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (170) 3-Z-[1-(4-(dimethylaminomethyl)-3,5-dichloro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (171) 3-Z- [1-(4-(N-((4-methyl-piperazin-l-yl)-methylcarbonyl) -N-methyl-amino) -anilino) -1-phenyl-methylene] - 6-ethoxycarbonyl-2-indolinone (172) 3-Z-[1-(4-(N-(imidazo~l-yl-methylcarbonyl)-N-methyl-amino) -anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (173) 3-Z- [1- (4- (N-„"(phthalimido-2-yl-methylcarbonyl) -N-methyl-amino) -anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (174) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (175) 3-Z- [1-(4-(N-acetylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (176) 3-Z-[1-(4-(N-methylsulphonylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (177) 3-Z-[1-(4-(N-((N-(2-methoxyethyl) -N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6 -ethoxycarbony1-2 -indolinone (178) 3-Z- [1-(4- (N-((N-(2-dimethylaminoethyl)-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (179) 3-Z-[1-(4-(N-((di-(2-hydroxyethyl)-amino)-methylcarbonyl)-N-methyl-amino)-anilino) -1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (180) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino) -methylene] -6-ethoxycarbonyl-2-indolinone (181) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-ethylidene]-6-ethoxycarbonyl-2-indolinone (182) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-propylidene]-6-ethoxycarbonyl-2-indolinone (183) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone (184) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-methylene]-6-ethoxycarbonyl-2 -indolinone (185) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-ethylidene]-6-ethoxycarbonyl-2-indolinone (186) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-propylidene]-6-ethoxycarbonyl-2 -indolinone (187) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-butylidene]-6-ethoxycarbonyl-2 -indolinone (188) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (189) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (190) 3-Z-[1-(4-((imidazolidin-2/4-dion-5-ylidene)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (191) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (192) 3-Z-[1-(4-(N-tert.butoxycarbonyl-aminomethyl)-anilino) 1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (193) 3-Z-[1-(4-(2-oxo-pyrrolidin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (194) 3-Z-[1-(4-(N-aminocarbonylmethyl-N-methylsulphonyl- amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (195) 3-Z-[1-(4-(N-cyanomethyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (196) 3-Z-[1-(4-(2-(imidazol-4-yl)-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (197) 3-Z-[1-(4-((2-(N-benzyl-N-methyl-amino)-ethyl)-N- methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (198) 3-Z-[1-(4-cyclohexylamino-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (199) 3-Z-[1-(4-(imidazol-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (200) 3-Z-[1-(4-(imidazol-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (201) 3-Z-[1-(N-methyl-piperidine-4-yl-amino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (202) 3-Z-[1-(4-(imidazol-4-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (203) 3-Z-[1-(4-((4-hydroxy-piperidin-l-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (204) 3-Z- [1- (4- ( (4-methoxy-piperidin-l-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (205) 3-Z-[1-(4-benzyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (206) 3-Z- [1-(4-(N-(3-trifluoroacetylamino-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (207) 3-Z- [1-(4-(4-tert.butoxycarbonyl-piperazin-1-yl-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (208) 3-Z-[1-(4-(1-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (209) 3-Z- [1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (210) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-3-amino-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (211) 3-Z-[1-(4-((3-(N-benzyl-N-methyl-amino)-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (212) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl) -N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (213) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-butyryl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (214) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-isobutyryl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (215) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzoyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (216) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-amino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (217) 3-Z-[l-(4-(4-hydroxymethyl-piperidin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (218) 3-Z-[1-(4-(2-(4-hydroxy-piperidin-l-yl)-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (219) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (220) 3-Z- [1- (4- (N- (2-dimethylamino-ethyl)-N-butylsulphonyl- amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl- 2-indolinone (221) 3-Z- [1- (4- (N- (2-dimethylamino-ethyl)-N-phenylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (222) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (223) 3-Z-[1-(4-((imidazolidin-2,4-dion-5-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (224) 3-Z-[1-(4-((3-hydroxy-pyrrolidin-l-yl)-methyl)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (225) 3-Z-[1-(4-(cyclohexylyl-methyl)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (226) 3-Z-[1-(4-(cyclohexyl-carbonyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (227) 3-Z-[1-(4-diethylaminomethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (228) 3-Z-[1-(4-(N-(n-hexyl)-N-methyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (229) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(furan-2-carbonyl)-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2 -indolinone (230) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl) -N-(2-methoxy-benzoyl)-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (231) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(pyridine-3- carbonyl)-amino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (232) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)- amino)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (233) 3-Z-[1-(4-(imidazol-2-yl)-anilino)-l-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (234) 3-Z-[1-(4-(l-ethyl-imidazol-2-yl)-anilino)-l-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (235) 3-Z-[1-(4-(l-benzyl-imidazol-2-yl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (236) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-isopropylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (237) 3-Z- [1- (4- (N-,"( (4-benzyl-piperazin-l-yl) -methylcarbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (238) 3-Z-[1-(4-(N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (239) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-bromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (240) 3-Z-[1-(4-(5-methyl-imidazol-4-yl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (241) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (242) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-benzyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (243) 3-Z-[1-(4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (244) 3-Z-[1-(4-(N-((N-aminocarbonylmethyl-N-methyl-amino)- methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone (245) 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (246) 3-Z- [1- (4- (N-,"(di- (2 - me thoxy ethyl) -amino-methylcarbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (247) 3-Z-[1-(4-(N-((2-(4-tert.butoxycarbonyl-piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone (248) 3-Z-[1-(4-(N-((2-(piperidin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (249) 3-Z-[1-(4-(N-((2-(N-benzyl-N-methyl-amino)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (250) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-isopropyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (251) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (252) 3-Z-[1-(4-(N-((4-tert.butoxycarbonyl-piperazin-1-yl)-methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (253) 3-Z- [1- (4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl) N-benzyl-amino) -anilino) -1-phenyl-methylene] -6-ethoxycarbonyl 2-indolinone (254) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-benzyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (255) 3-Z- [1- (4- (N-,"(piperidin-l-yl-methylcarbonyl) -N-benzyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (256) 3-Z-[l-(4-(l,2,4-triazol-2-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbony1-2 -indolinone (257) 3-Z- [1-(4-(l,2,3-triazol-2-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (258) 3-Z- [1-(4-(1,2,3-triazol-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (259) 3-Z- [1- (4-( (N-aminocarbonylmethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (260) 3-Z-[1-(4-((di-(2-methoxy-ethyl)-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (261) 3-Z-[1-(4-((di-(2-hydroxy-ethyl)-amino)-methyl)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (262) 3-Z-[1-(4-((N-ethoxycarbonylmethyl-N-methyl-amino) -methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (263) 3-Z- [1- (4-(azetidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (264) 3-Z-[1-(4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (265) 3-Z-[1-(4-((N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (266) 3-Z- [1-(4- ( (N-(tert.butoxycarbonyl-3-amino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6- ethoxycarbonyl-2 -indolinone (267) 3-Z-[1-(4-((N-(methylcarbamoyl-methyl)-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (268) 3-Z-[1-(4-((N-(dimethylcarbamoyl-methyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (269) 3-Z-[1-(4-((N-propyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (270) 3-Z-[1-(4-((N-(2-dimethylamino-ethyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (271) 3-Z-[1-(4-((N-(3-dimethylamino-propyl)-N-methyl-amino)- methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl- 2-indolinone (272) 3-Z-[1-(4-((N-(2-methoxy-ethyl)-N-methyl-amino)-methyl)- anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (273) 3-Z- [1-(4-((N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl) - anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (274) 3-Z-[1-(4-((N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone (275) 3-Z- [1- (4- (3-oxo-piperazin-l-yl-methyl)-anilino)-1-phenyl-methylene] -6,-ethoxycarbonyl-2-indolinone (276) 3-Z- [1-(4-(N-(piperazin-1-yl-methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (277) 3-Z- [1- (4-(N-((2-(piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (278) 3-Z- [1- (4- ( (N-(3-amino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (279) 3-Z-[1-(4-(N-(3-methylamino-propyl) -N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl- 2-indolinone (280) 3-Z-[1-(4-Ureidomethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone (281) 3-Z-[1-(4-guanidinomethyl-anilino)-1-phenyl-methylene] -6 -ethoxycarbonyl-2-indolinone (282) 3-Z-[1-(4-(N-methylsulphonyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (283) 3-Z-[1-(4-(4-benzoyl-piperazin-l-yl-methyl)-anilino) -1- phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (284) 3-Z-[1-(4-((N-(3-acetylamino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (285) 3-Z-[1-(4-((N-(3-methylsulphonylamino-propyl)-N-methyl-amino) -methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (286) 3-Z-[1-(4-((N-carboxymethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone (287)3-Z-(1-anilino-l-phenyl-methylene)-6-methoxycarbonyl-2-indolinone (288) 3-Z-[1-(4-nitro-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone (289) 3-Z- [1-(4-fluoro-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2-indolinone (290) 3-Z- [1-(4-chloro-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2-indolinone (291) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2-indolinone (292) 3-Z- [1-(4-iodo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (293) 3-Z-[1-(4-cyano-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone (294) 3-Z-[1-(4-carboxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (295) 3-Z-[1-(4-methoxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (296) 3-Z- [1-(4-ethoxy-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone (297) 3-Z- [1-(4-trifluoromethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (298) 3-Z- [1-(4-methylmercapto-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (299) 3-Z- [1-(4-(isopropylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone (300) 3-Z-[1-(4-(anilinomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (301) 3-Z- [1-(4-(isobutylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (302) 3-Z-[1-(4-(cyclohexylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone (303) 3-Z- [1-(4-(benzylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (304) 3-Z-[1-(4-((N-methyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (305) 3-Z- [1-(4-((N-isopropyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (306) 3-Z-[1-(4-((N-ethyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (307) 3-Z- [1-(4-((N-ethyl-N-isopropyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (308)"3-Z- [1- (4-(dipropylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (309) 3-Z- [1-(4-(diisopropylaminomethyl)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (310) 3-Z-[1-(4-((N-benzyl-N-ethyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (311) 3-Z-[1-(4-(dibenzylaminomethyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone (312) 3-Z-[1-(4-(3,6-dihydro-2H-pyridin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (313) 3-Z-[1-(4-(3,5-dimethyl-piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (314) 3-Z-[1-(4-(azepan-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (315) 3-Z- [1- (4- (2-amino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (316) 3-Z- [1- (4-(2-methylamino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (317) 3-Z- [1-(4- (2-ethylamino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (318) 3-Z-[1-(4-(2-dimethylamino-ethyl)-anilino)-1-phenyl-methylene]- 6 -methoxycarbonyl-2 -indolinone (319) 3-Z-[1-(4-(2-diethylamino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (320) 3-Z- [1- (4-(2-piperidin-l-yl-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (321) 3-Z-[1-(4-(2-acetylamino-ethyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone (322) 3-Z-[1-(4-(3-amino-propyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (323) 3-Z- [1-(4-(3-dimethylamino-propyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (324) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (325) 3-Z-[1-(4-(N-ethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (326) 3-Z-[1-(4-(N-diethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (327) 3-Z-[1-(4-(N-dipropylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (328) 3-Z-[1-(4-(N-((N-ethyl-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone (329) 3-Z- [1-(4-(N-((N-ethyl-N-propyl-amino)-methylcarbonyl)- N-methyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2-indolinone (330) 3-Z-[1-(4-(N-((N-methyl-N-propyl-amino)-methylcarbonyl)- N-methyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl- 2 -indolinone (331) 3-Z- [1- (4- (N-"dimethylaminomethylcarbonyl-N-ethyl-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (332) 3-Z- [1- (4- (N-dirnethylaminomethylcarbonyl-N-propyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (333) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-butyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (334) 3-Z-[l-(4-(N-(2-amino-ethylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (335) 3-Z-[1-(4-(N-(2-diethylamino-ethylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (336) 3-Z-[1-(4-(N-acetyl-N-(2-aminoethyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (337) 3-Z-[1-(4-(N-acetyl-N-(2-methylamino-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (338) 3-Z-[1-(4-(N-acetyl-N-(3-methylamino-propyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (339) 3-Z-[1-(4-(N-acetyl-N-(2-piperidin-l-yl-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (340) 3-Z-[1-(4-(N-acetyl-N-(aminocarbonylmethyl)-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (341) 3-Z-[1-(4-(N-acetyl-N-(piperidin-1-yl-carbonylmethyl)- amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2- indolinone (342) 3-Z-[1-(4-(N-methyl-N-(aminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (343) 3-Z-[1-(4-(N-methyl-N-(methylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (344) 3-Z-[1-(4-(N-methyl-N-(dimethylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (345) 3-Z-[1-(4-(N-methyl-N-(piperidin-1-yl-carbonyl)-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (346) 3-Z- [1-(4-(N-(2-ethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (347) 3-Z- [1-(4-(N-(2-diethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (348) 3-Z-[1-(4-(N-(2-pyrrolidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (349) 3-Z- [1- (4-(N-(2-piperidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (350) 3-Z- [1- (4-(N-(2-piperazin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (351) 3-Z- [1- (4- (N- (2- (4-morphc-1 in-1-yl) -ethyl) -N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2 -indolinone (352) 3-Z-[1-(4-(N-(ethylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (353) 3-Z- [1- (4- (N-,"(diethylaminocarbonylmethyl) -N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (354) 3-Z-[1-(4-(N-(pyrrolidin-1-yl-carbonylmethyl)-N-methyl-sulphonyl-amino)-anilino)-1-phenyl-methylene] -6- methoxycarbonyl-2 -indolinone (355) 3-Z-[1-(4-(N-(piperidin-1-yl-carbonylmethyl)-N-methyl- sulphonyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone (356) 3-Z-[1-(4-(N-(piperazin-1-yl-carbonylmethyl)-N-methyl- sulphonyl-amino)-anilino)-1-phenyl-methylene] -6- methoxycarbonyl-2 -indolinone (357) 3-Z-[1-(4-(N-((morpholin-4-yl)-carbonylmethyl)-N-methyl- sulphonyl-amino)-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2-indolinone (358) 3-Z-[1-(4-(2-dimethylamino-ethoxy)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2 -indolinone (359) 3-Z-[1-(4-(3-dimethylamino-propoxy)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (360) 3-Z-[1-(4-(aminocarbonylmethyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2-indolinone (361) 3-Z- [1-(4-(2-aminocarbonyl-ethyl)-anilino)-1-phenyl- methylene]-6-methoxycarbonyl-2-indolinone (362) 3-Z- [1-(4-(pyridin-2-yl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (363) 3-Z-[1-(4-(pyridine-3-yl)-anilino)-1-phenyl-methylene]-6 -methoxycarbonyl-2,- indolinone (364) 3-Z- [1-(4((N-phenethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (365) 3-Z- [1-(4-(N-acetyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone (366) 3-Z- [1-(4-(N-ethylcarbonyl-N-(dimethylaminocarbonyl-methyl)-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (367) 3-Z- [1-(4-(N-methyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -iridolinone (368) 3-Z- [1-(4-carboxymethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (369) 3-Z- [1-(4-carbamoylmethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (370) 3-Z- [1-(4-dimethylcarbamoylmethyl-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (371) 3-Z-[1-(4-tetrazol-5-yl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (372) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-methylene]- 6-methoxycarbonyl-2 -indolinone (373) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-ethylidene]- 6-methoxycarbonyl-2 -indolinone (374) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-propylidene]-6-methoxycarbonyl-2-indolinone (375) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-butylidene]-6-methoxycarbonyl-2 -indolinone (376) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-methylene]-6-methoxycarbonyl-2-indolinone (377) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-ethylidene]-6-methoxycarbonyl-2-indolinone (378) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-propylidene]-6-methoxycarbonyl-2-indolinone (379) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-butylidene]-6-methoxycarbonyl-2-indolinone (380) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-methylene]-6-methoxycarbonyl-2-indolinone (381) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-ethylidene]-6-methoxycarbonyl-2-indolinone (382) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-propylidene]-6-methoxycarbonyl-2-indolinone (383) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-butylidene]-6-methoxycarbonyl-2-indolinone (384) 3-Z- [1-(4-tetrazol-5-yl-anilino)-methylene]-6-methoxy¬carbonyl - 2 -indolinone (385) 3-Z- [1-(4-tetrazol-5-yl-anilino)-ethylidene]-6-methoxy¬carbonyl -2 -indolinone (386) 3-Z- [1-(4-tetrazol-5-yl-anilino)-propylidene]-6-methoxy¬carbonyl -2 -indolinone (387) 3-Z-[1-(4-tetrazol-5-yl-anilino)-butylidene]-6-methoxy¬carbonyl -2 -indolinone (388) 3-Z-[1-(4-carboxy-anilino)-methylene] -6-methoxycarbonyl -2-indolinone (389) 3-Z-[1-(4-carboxy-anilino)-ethylidene] -6-methoxycarbonyl-2 -indolinone (390) 3-Z-[1-(4-carboxy-anilino)-propylidene]-6-methoxy¬carbonyl - 2 - indolinone (391) 3-Z-[1-(4-carboxy-anilino)-butylidene]-6-methoxycarbonyl-2 -indolinone (392) 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)-anilino)-1- methyl-methylene]-6-methoxycarbonyl-2 -indolinone (3 93) 3-Z-[l-(4-(2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone (394) 3-Z- [1-(4-((benzo(1,3)dioxol-5-yl-methyl)-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone (395) 3-Z-[1-(4-(N-phenethyl-N-methyl-aminomethyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone (396) 3-Z-[1-(4-(N-(3,4-dimethoxy-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone (397) 3-Z-[1-(4-(N-(4-Chloro-benzyl)-N-methyl-amino-methyl)-anilino)-l-methyl-m£thylene]-6-methoxycarbonyl-2-indolinone (398) 3-Z-[1-(4-(N-(4-methylbenzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone (399) 3-Z-[1-(4-(N-(4-fluoro-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone (400) 3-Z-[1-(4-(N-(4-bromo-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone (401) 3-Z-[1-(4-(N-(3-dimethylamino-propionyl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (402) 3-Z-[1-(4-(N-(4-dimethylamino-butyryl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (403) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(2-dimethylamino-ethylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (404) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(3-dimethylamino-propylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (405) 3-Z-[1-(4-((2-hydroxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (406) 3-Z- [1-(4-((2-methoxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (407) 3-Z-[1-(4-((2-dimethylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (408) 3-Z-[1-(4-((3-dimethylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (409) 3-Z-[1-(4-((N-tert.butoxycarbonyl-2-amino-ethyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (410) 3-Z-[1-(4-((N-tert.butoxycarbonyl-3-amino-propyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indol.inone (411) 3-Z-[1-(4-((2-amino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (412) 3-Z-[1-(4-((3-amino-propyl)-amino-methyl)-anilino)-1- phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (413) 3-Z-[1-(4-((2-acetylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (414) 3-Z- [1-(4-((3-acetylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (415) 3-Z-[1-(4-((2-methylsulphonylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (416) 3-Z- [1-(4-((3-methylsulphonylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (417) 3-Z- [1-(4-(N-(N-tert.butoxycarbonyl-2-amino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (418) 3-Z- [1- (4- (N-,(2-amino-ethyl) -N-methyl-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (419) 3-Z-[1-(4-(N-(2-acetylamino-ethyl)-N-methyl-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (420) 3-Z- [1-(4-(N-(2-methylsulphonylamino-ethyl)-N-methyl-amino-methyl) -anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (421) 3-Z- [1-(4-(carboxymethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (422) 3-Z-[1-(4-(ethoxycarbonylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (423) 3-Z-[1-(4-(carbamoylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (424) 3-Z-[1-(4-(dimethylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (425) 3-Z-[1-(4-(methylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (426) 3-2- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-amino-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (427) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-nitro-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (428) 3-Z-[1-(4-(N-plmethylaminomethylcarbonyl-N-methyl-amino)-3-acetylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (429) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methylsulphonylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (430) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-cyano-anilino)-l-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (431) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-hydroxy-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone (432) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methoxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (433) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-ethoxycarbonyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (434) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl- amino)-3-carboxy-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone (435) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-carbamoyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (436) 3-2-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-chloro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (437) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-fluoro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (438) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-bromo-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (439) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (44 0) 3-Z-[l-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-methoxycarbony1-2 -indolinone (441) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl- amino)-3,5-dibromo-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone (442) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl- amino)-3,5-dichloro-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2 -indolinone (443) 3-Z- [1- (4- (dimethylaminomethyll.-3-amino-anilino) -1- phenyl-methylene]-6-methoxycarbony1-2 -indolinone (444) 3-Z-[1-(4-(dimethylaminomethyl)-3-nitro-anilino)-1- phenyl-methylene]- 6-methoxycarbonyl-2-indolinone (445) 3-Z-[1-(4-(dimethylaminomethyl)-3-acetylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (446) 3-Z-[1-(4-(dimethylaminomethyl)-3-methylsulphonylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (447) 3-Z-[1-(4-(dimethylaminomethyl)-3-cyano-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (448) 3-Z-[1-(4-(dimethylaminomethyl)-3-hydroxy-anilino)-1-pheny1-methylene]-6-methoxycarbonyl-2-indolinone (449) 3-Z-[1-(4-(dimethylaminomethyl)-3-methoxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (450) 3-Z-[1-(4-(dimethylaminomethyl)-3-ethoxycarbonyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (451) 3-Z-[l-(4-(dimethylaminomethyl)-3-carboxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (452) 3-Z-[1-(4-(dimethylaminomethyl)-3-carbamoyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (453) 3-Z-[1-(4-(dimethylaminomethyl)-3-chloro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (454) 3-Z-[1-(4-(dimethylaminomethyl)-3-fluoro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (455) 3-Z-[1-(4-(dimethylaminomethyl)-3-bromo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone (456) 3-Z-[1-(4-(dimethylaminomethyl)-3-methyl-anilino)-1- phenyl-methylene]-6-methoxycarbonyl- 2-indolinone (457) 3-Z-[1-(4-(dimethylaminomethyl)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (458) 3-Z-[1-(4-dimethylaminomethyl-3,5-dibromo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (459) 3-Z-[1-(4-(dimethylaminomethyl) -3 , 5-dichloro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (460) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene] -6-[(2-hydroxy-ethoxy)-carbonyl] -2-indolinone (461) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene] -6- [ (ethoxycarbonyl-methoxy) -carbonyl] -2-indolinone (462) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene] -6-[(carboxy-methoxy)-carbonyl]-2-indolinone (463) 3-Z-[1-(4-(dimethylaminomethyl) -anilino)-1-phenyl-methylene] -6-[(carbamoyl-methoxy)-carbonyl] -2-indolinone (464) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-[(2-hydroxy-ethoxy) -carbonyl]-2-indolinone (465) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(ethoxycarbonyl-methoxy) -carbonyl]-2-indolinone (466) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino) -1-phenyl-methylene] -6- [ (carboxy-methoxy) -carbonyl]-2-indolinone (467) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(carbamoyl-methoxy)-carbonyl]" - 2 - indolinone (468) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2-methoxy-ethoxy)-carbonyl]-2-indolinone (469) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2-dimethylamino-ethoxy)-carbonyl]-2-indolinone (470) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl- amino)-anilino)-1-phenyl-methylene]-6-[(2-(N- tert.butoxycarbonyl-amino)-ethoxy)-carbonyl]-2-indolinone (471) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2-amino-ethoxy)-carbonyl]-2-indolinone (472) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2,2,2-trifluoroethoxy)-carbonyl]-2-indolinone (473) 3-Z-[1-(4-(N-((4-methyl-piperazin-l-yl)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (474) 3-Z-[1-(4-(N-(imidazo-1-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (475) 3-Z- [1-(4-(N-(phthalimido-2-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (476) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (477) 3-Z-[1-(4-(N-acetylaminomethylcarbonyl-N-methyl-amino)- anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (478) 3-Z-[1-(4-(N-methylsulphonylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 - i ndo 1 i none „" (479) 3-Z-[1-(4-(N-((N-(2-methoxyethyl)-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (480) 3-Z-[1-(4-(N-((N-(2-dimethylaminoethyl)-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone (481) 3-Z-[1-(4-(N-((di-(2-hydroxyethyl)-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (482) 3-Z-[1-(4-tert.butoxycarbonylmethyl-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone (483) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-methylene]-6-methoxycarbonyl-2-indolinone (484) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-ethylidene]-6-methoxycarbonyl-2-indolinone (485) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-propylidene]-6-methoxycarbonyl-2-indolinone (486) 3-Z-[l-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-butylidene]-6-methoxycarbonyl-2-indolinone (487) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-methylene]-6-methoxycarbonyl-2-indolinone (488) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-ethylidene]-6-methoxycarbonyl- 2 -indolinone (489) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-propylidene]-6-methoxycarbonyl-2 -indolinone (490) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-butylidene]-6-methoxycarbonyl-2 -indolinone (491) 3-Z- [1-(4-tert.butyloxycarbonyl-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone (492) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (493) 3-Z- [1- (4-(N-(3-dimethylamino-propyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone (494) 3-Z- [1-(4-(N-methyl-acetylamino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (495) 3-Z- [1-(4-(imidazol-4-yl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone (496) 3-Z- [1-(4-((N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone (497) 3-Z- [1-(4-(N-benzyl-N-methyl-amino-methyl)-anilino)-1- methyl-methylene]-6-carbamoyl-2-indolinone (498) 3-Z-[l-(4-(2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl) -anilino) -1-methyl-methylene] -6-carbamoyl-2-indolinone (499) 3-Z-[1-(4-((benzo(1,3)dioxol-5-yl-methyl)-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-carbamoyl~2-indolinone (500) 3-Z-[1-(4-(N-phenethyl-N-methyl-amino-methyl)-anilino)- 1-methyl-methylene]- 6-carbamoyl-2 -indolinone l (501) 3-Z-[1-(4-(N-(3,4-dimethoxy-benzyl)-N-methyl-amino- methyl)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone (502) 3-Z-[1-(4-(N-(4-Chloro-benzyl)-N-methyl-amino-methyl)- anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone (503) 3-Z-[1-(4-(N-(4-methyl-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone (504) 3-Z-[1-(4-(N-(4-fluoro-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone (505) 3-Z-[1-(4-(N-(4-bromo-benzyl)-N-methyl-amino-methyl)-anilino) -1-methyl-methylene]-6-carbamoyl-2-indolinone (506) 3-Z- [1- (4-( (N- (2-methoxy-ethyl)-N-methyl-amino)-methyl)-anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone (507) 3-Z-[1-(4-(dimethylaminomethyl)-anilino) -1-phenyl-methylene]-6- [ (2-amino-ethoxy)-carbonyl]-2-indolinone (508) 3-Z-[1-(4-((N-(3-methylsulfonylamino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone Example 13 Dry ampoule containing 75 mg of active substance per 10 ml Composition: Active substance 75.0 mg Mannitol 50.0 mg water for injections ad 10.0 ml Preparation: Active substance and mannitol are dissolved in water. After packaging the solution is freeze-dried. To produce the solution ready for use, the product is dissolved in water for injections. Example 14 Dry ampoule containing 35 mg of active substance per 2 ml Composition: Active substance 35.0 mg Mannitol 100.0 mg water for injections ad 2.0 ml Preparation: Active substance and mannitol are dissolved in water. After packaging, the solution is freeze-dried. To produce the solution ready for use, the product is dissolved in water for injections. Example 15 Tablet containing 50 mg of active substance Composition: (1) Active substance 50.0 mg (2) Lactose 98.0 mg (3) Maize starch 50.0 mg (4) Polyvinylpyrrolidone 15.0 mg (5) Magnesium stearate 2 . 0 mg 215.0 mg Preparation: (1), (2) and (3) are mixed together and granulated with an aqueous solution of (4). (5) is added to the dried granulated material. From this mixture tablets are pressed, biplanar, faceted on both sides and with a dividing notch on one side. Diameter of the tablets: 9 mm. Example 16 Tablet containing 350 mg of active substance Composition: (1) Active substance 350.0 mg (2) Lactose 136.0 mg (3) Maize starch 80.0 mg (4) Polyvinylpyrrolidone 30.0 mg (5) Magnesium stearate 4.0 mg 600.0 mg Preparation: (1), (2) and (3) are mixed together and granulated with an aqueous solution of (4). (5) is added to the dried granulated material. From this mixture tablets are pressed, biplanar, faceted on both sides and with a dividing notch on one side. Diameter of the tablets: 12 mm. Example 17 Capsules containing 50 mg of active substance Composition: (1) Active substance 50.0 mg (2) Dried maize starch 58.0 mg (3) Powdered lactose 50.0 mg (4) Magnesium stearate 2.0 mg 160.0 mg Preparation: (1) is triturated with (3). This trituration is added to the mixture of (2) and (4) with vigorous mixing. This powder mixture is packed into size 3 hard gelatine capsules in a capsule filling machine. Example 18 Capsules containing 350 mg of active substance Composition: (1) Active substance 350.0 mg (2) Dried maize starch 46.0 mg (3) Powdered lactose 3 0.0 mg (4) Magnesium stearate 4.0 mg 4 3 0.0 mg Preparation: (1) is triturated with (3). This trituration is added to the mixture of (2) and (4) with vigorous mixing. This powder mixture is packed into size 0 hard gelatine capsules in a capsule filling machine. Example 19 Suppositories containing 100 mg of active substance 1 suppository contains: Active substance 100.0 mg Polyethyleneglycol (M.W. 1500) 600.0 mg Polyethyleneglycol (M.W. 6000) 460.0 mg Polyethylenesorbitan monostearate 840.0 mg 2,000.0 mg Preparation: The polyethyleneglycol is melted together with polyethylene sorbitan monostearate. At 40°C the ground active substance is homogeneously dispersed in the melt. It is cooled to 38°C and poured into slightly chilled suppository moulds. We claim: 1. Indolinones of general formula I (I), wherein X denotes an oxygen atom, R1 denotes a hydrogen atom, R2 denotes a carboxy group, a straight-chain or branched C1-4-alk- oxycarbonyl group, a straight-chain or branched C1-3-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl group, a straight-chain or branched C2-3-alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a C1-3-alkoxy—or di-(C1-3-alkyl)-amino group, an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy group or, if R4 does not denote an aminosulphonyl-phenyl or N-(C1-5-alkyl)-C1-3-alkylaminocarbonyl- phenyl group, it may also denote a di-(C1-2-alkyl)-aminocarbonyl group, R3 denotes a C1-4-alkyl group or a phenyl group which may be substituted by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C1-3-alkyl, hydroxy or C1-3-alkoxy group, R4 denotes a C5-6-cycloalkyl group, wherein the methylene group in position 4 of the cyclohexyl group may be substituted by an amino group or replaced by a -N(C1-3-alkyl) group, a phenyl group, a phenyl group disubstituted by C1-3-alkyl, C1-3-alkoxy or nitro groups, wherein the substituents may be identical or different, or a phenyl group substituted by the group R6, which may additionally be substituted by a chlorine or bromine atom or by an amino or nitro group, wherein R6 denotes a fluorine, chlorine or bromine atom, a C1-3-alkyl, C1-3-alkoxy, nitro, or amino or C5-6-cycloalkyl group, an imidazolyl or tetrazolyl group bound via a carbon atom, wherein the abovementioned heteroaromatic groups in the carbon skeleton may be substituted by a C1-3-alkyl group or a hydrogen atom bound to a nitrogen atom may be replaced by a C1-3-alkyl or phenyl-C1-3-alkyl group, the group of formula a carboxy, C1-4-alkoxycarbonyl or C5-7-cycloalkyl-carbonyl group, a 5 or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH group, an unbranched C1-3-alkyl group terminally substituted by the group R7, wherein R7 denotes a C5-7-cycloalkyl group, wherein in a 5 or 6-membered cycloalkyl group a -(CH2)2 group may be replaced by a -CO-NH group, a -(CH2)3 group may be replaced by an - NH-CO-NH- or a -(CH2)4 group may be replaced by an -NH-CO-NH-CO group, whilst in each case a hydrogen atom bound to a nitrogen atom may be replaced by a C1-3-alkyl group, a phenyl or pyridinyl group or a pyrrolyl, imidazolyl or triazolyl group bound via a carbon or nitrogen atom, wherein the abovementioned heteroaromatic groups in the carbon skeleton may be substituted by a C1-3-alkyl group, a hydroxy group, an amino, C1-6-alkylamino, di-(C1-6-alkyl)-amino, henyl-C1-3-alkylamino or N-(C1-3-alkyl)-phenyl-C1-3-alkylamino group, a co-hydroxy-C2-3-alkyl-amino, di-(to-hydroxy-C2-3-alkyl)-amino or di-(co-(C1-3-alkoxy)-C2-3-alkyl)-amino group, a C1-3-alkylcarbonylamino-C2-3-alkyl-N-(C1-3-alkyl)-aniino group, a C1-3-alkylsulphonylamino group, a N-(C1-3-alkyl)-hydroxycarbonyl-C1-3-alkyl-amino group, a guanidino group wherein a hydrogen atom may be replaced by a C1-3-alkyl group, a group of formula -N(R8)-CO-(CH2)n -R9 (II), wherein R8 denotes a hydrogen atom or a C1-3-alkyl group, n denotes one of the numbers 0 or 1 and R9 denotes an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino or C1-3-alkoxy group, a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH, -N(C1-3-alkyl) or -N(C1-3-alkyl-carbonyl) group, or, if n denotes one of the numbers 1, 2 or 3, R9 may also denote a hydrogen atom, a group of formula -N(R10)-(CH2)m-(CO)0-Rn (III), wherein R10 denotes a C1-3-alkyl group, m denotes one of the numbers 1, 2 or 3, o denotes the number 1 or, if m is one of the numbers 2 or 3, o may also denote the number 0 and R11 denotes an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, C1-4-alkoxy or methoxy-C1-3-alkoxy group or a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH, -N(C1-3-alkyl) or -N(C1-3-alkyl-carbonyl) group, an azetidino, pyrrolidino, piperidino, 2,6-dimethyl-piperidino—or azepino group, wherein the methylene group in position 3 of the pyrrolidino group may be substituted by a hydroxy group, the methylene group in position 4 of the piperidino group may be substituted by a hydroxy or hydroxy-C1-3-alkyl group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -N(C1-3-alkyl) or -N(benzoyl) group, wherein a methylene group linked to an imino-nitrogen atom of the pyrrolidino or piperazino group may be replaced by a carbonyl group, or Re denotes a straight-chain C1-3-alkyl group which is terminally substituted by a carboxy or C1-3-alkoxy-carbonyl group, a group of formula -N(R12)-CO-(CH2)p-R13 (IV), wherein R12 denotes a C1-3-alkyl or phenyl-C1-3-alkyl group, p denotes one of the numbers 1 or 2 and R13 denotes C1-4-alkylamino, di-(C1-4-alkyl)-amino, N-(C1-3-alkyl)-benzylamino, di-(2-methoxy-ethyl)-amino, or aminocarbonyl-methyl-N-(methyl)-amino group, a pyrrolyl, pyrazolyl or imidazolyl group bound via a nitrogen atom and optionally substituted by a C1-3-alkyl group, a pyrrolidino, piperidino, morpholino or a piperazino group optionally substituted in the 4 position by a C1-3-alkyl, phenyl-C1-3-alkyl or C1-4-alkoxycarbonyl group or, if p denotes the number 1 or 2, it may also denote a hydrogen atom, a group of formula-N(R14)-(CH2)q-(CO)r-R15 (V), wherein R14 denotes a hydrogen atom, a C1-4-alkyl, phenylcarbonyl, phenyl-C1-3-alkylcarbonyl, furyl-carbonyl, pyridinyl-carbonyl, C1-4-alkylsulphonyl, phenylsulphonyl or phenyl-C1-3-alkylsulphonyl group, q denotes one of the numbers 1, 2 or 3, r denotes the number 1 or, if q is one of the numbers 2 or 3, it may also denote the number 0 and R15 denotes an amino, C1-4-alkylamino, di-(C1-4-alkyl)-amino, or N-(Ci-4-alkyl)-benzylamino group, or a group of formula -N(R16)-S02-R17 (VI), wherein R16 denotes a C1-3-alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino group and R17 denotes a C1-3-alkyl group, wherein all the single-bonded phenyl groups contained in the groups mentioned under Re may be substituted by a methoxy group and R5 denotes a hydrogen atom, wherein a hydrogen atom bound to a nitrogen atom in the abovementioned groups may be replaced by an acetyl or tert.butoxycarbonyl group, the carboxy groups contained in the abovementioned groups may also be present in the form of the tert.butoxycarbonyl precursor group, the tautomers, the diastereomers, the enantiomers, the mixtures such as herein described and the salts such as herein described. 2. Indolinones of general formula I as claimed in claim 1, wherein X denotes an oxygen atom, R1 and R5 each denote a hydrogen atom, R2 denotes a methoxycarbonyl, ethoxycarbonyl or aminocarbonyl group, R3 denotes a phenyl group and R4 denotes a phenyl group monosubstituted by the group Re, wherein Re denotes an N-methyl-imidazol-2-yl group, an unbranched C1-3-alkyl group which is terminally substituted by a C1-4-alkylamino, di-(C1-4-alkyl)-amino, piperidino or 2,6-dimethyl-piperidino group, a group of formula -N(R12)-CO-(CH2)p-R13 (IV), wherein R12 denotes a C1-3-alkyl group, p denotes one of the numbers 1 or 2 and R13 denotes a di-(C1-3-alkyl) -amino group, or a group of formula -N(R14)-(CH2)q-(CO)r-R15 (V), wherein R14 denotes a C1-3-alkyl-carbonyl or C1-3-alkylsulphonyl group, q denotes one of the numbers 1, 2 or 3, r denotes the number 1 or, if q is one of the numbers 2 or 3, r may also denote the number 0 and R15 denotes a di-(C1-3-alkyl)-amino group, the tautomers, the diastereomers, the enantiomers, the mixtures such as herein described and the salts such as herein described. 3. The following substituted indolinones of general formula I as claimed in claim 1: (a) 3-Z-[l-(4-(piperidin-l-yl-methyl)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl- 2 -indolinone, (b) 3-Z-[(l-(4-(piperidin-l-yl-methyl)-anilino)-l-phenyl-methylene]-6-carbamoyl-2-indolinone, (c) 3-Z-[l-(4-(piperidin-l-yl-methyl)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (d) 3-Z- [ 1 - (4- (dimethylaminomethyl) -anilino)-1 -phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (e) 3-Z-[l-(4-((2,6-dimethyl-piperidin- l-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (f) 3-Z-[l-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (g) 3-Z-[l-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (h) 3-Z-[ 1 -(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)- anilino)-1 -phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (i) 3-Z-[l-(4-(dimethylaminomethyl)-anilino)-l-phenyl-methylene]- 6-methoxycarbonyl-2-indolinone, (j) 3-Z-[l-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)- anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (k) 3-Z-[l-(4-ethylaminomethyl-anilino)-l-phenyl-methylene]-6- methoxycarbonyl- 2 -indolinone, (1) 3-Z-[l-(4-(l-methyl-imidazol-2-yl)-anilino)-l-phenyl-methylene]- 6-met±io3tycarbonyl-2 -indolinone, (m) 3-Z-[ 1 -(4-(N-dimethylaminomethylcarbonyl-N-methyl-aniino)- anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone> (n) 3-Z-[l-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)- anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (o) 3-Z-[ l-(4-(N-(3-dimethylamino-propyl)-N-methylsulphonyl-ami- no)-anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (p) 3-Z-[ 1 -(4-(N-dimethylaminocarbonylmethyl-N-methylsulphonyl- amino)-anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (q) 3-Z-[ l-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl- amino)-anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone, (r) 3-Z-[ 1 -(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-anilino)-1 - phenyl-methylene]-6-methoxycarbonyl-2-indolinone and (s) 3-Z-[ l-(4-methylaminomethyl-anilino)-1-phenyl-methylene]-6- methoxycarbonyl-2-indolinone, 4. Process for preparing the compounds as claimed in claims 1 to 3, wherein a) a compound of general formula wherein X and R3 are defined as in claims 1 to 3, R2 has the meanings given for R2 in claims 1 to 3, Ris denotes a hydrogen atom or a protecting group for the nitrogen atom of the lactam group, wherein one of the groups R2 and R18 may also denote a bond to a solid phase optionally formed via a spacer and the other one of the groups R2 and R18 has the abovementioned meanings, and Z1 denotes a halogen atom, a hydroxy, alkoxy or aryl- alkoxy group, is reacted with an amine of general formula wherein R4 and R5 are defined as in claims 1 to 3, and subsequently, if required, any protecting group used for the nitrogen atom of the lactam group is cleaved or a compound thus obtained is cleaved from a solid phase, or b) in order to prepare a compound of general formula I wherein R2 has the meanings given in claims 1 to 3, with the exception of the carboxy group, a compound of general formula wherein R1 and R3 to R5 are defined as in claims 1 to 3, or a reactive derivative thereof, is reacted with a compound of general formula H - R19 (X), wherein R19 denotes a C1-6-alkanol, a C4-7-cycloalkanol or an aromatic alcohol, a C1-6-alkanol which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C1-3-alkoxy-carbonyl, aminocarbonyl, C1-3-alkylamino-carbonyl or di-(C1-3-alkyl)-aminocarbonyl group, a C2-6-alkanol which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, C1-3-alkoxy, amino, C1-3-alkylamino or di-(C1-3-alkyl)-amino group, an amino or methylamino group, an ethylamino group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1-3-alkoxy group or a di-(C1-2-alkyl)-amino group, or c) in order to prepare a compound of general formula I, wherein R4 denotes a C1-4-alkyl group substituted by the group R7, wherein R7 denotes an amino, C1-7-alkylamino, di-(C1-7-alkyl)-amino, phenylamino, N-phenyl-C1-3-alkyl-amino, phenyl-C1-3-alkylamino, N-(C1-3-alkyl)-phenyl-C1-3-alkylamino or di-(phenyl-C1-3-alkyl)-amino group, a co-hydroxy-C2-3-alkyl-amino, N-(C1-3-alkyl)-co-hydroxy-C2-3-alkyl-amino, di-(co-hydroxy-C2-3-alkyl)-amino, di-(co-(C1-3-alkoxy)-C2-3-alkyl)-amino or N-(dioxolan-2-yl)-C1-3-alkyl-amino group, a C1-3-alkylcarbonylamino-C2-3-alkyl-amino or C1-3-alkylcarbonylamino-C2-3-alkyl-N-(C1-3-alkyl)-amino group, a C1-3-alkylsulphonylamino, N-(C1-3-alkyl)-C1-3-alkylsulphonylamino, C1-3-alkylsulphonylamino-C2-3-alkyl-amino or C1-3-alkylsulphonylamino-C2-3-alkyl-N-(C1-3-alkyl)-amino group, a group of formula -N(R10)-(CH2)m-(CO)o-R11 (III), wherein R10 denotes a hydrogen atom, a C1-3-alkyl group, a C1-3-alkylcarbonyl, arylcarbonyl, phenyl-C1-3-alkylcarbonyl, C1-3-alkylsulphonyl, arylsulphonyl or phenyl-C1-3-alkylsulphonyl group, m denotes one of the numbers 1, 2, 3 or 4, o denotes the number 1 and R11 denotes an amino, C1-4-alkylamino, di-(C1-4-alkyl)-amino, phenylamino, N-(C1-4-alkyl)-phenylamino, benzylamino, N-(C1-4-alkyl)-benzylamino, C1-4-alkoxy or C1-3-alkoxy-C1-3-alkoxy group, a di-(C1-4-alkyl)-amino-C1-3-alkylamino group optionally substituted in the 1 position by a C1-3-alkyl group, or a 4- to 7- membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl), -N(phenyl), -N(C1-3-alkyl-carbonyl) or -N(benzoyl) group, a C4-7-cycloalkylamino, C4-7-cycloalkyl-C1-3-alkylamino or C4-7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond and wherein the abovementioned groups may each additionally be substituted at the amino-nitrogen atom by a C5-7-cycloalkyl, C2-4-alkenyl or C1-4-alkyl group, or a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C1-3-alkyl, C1-3-alkoxy or amino group, and/or one or two hydrogen atoms may each be replaced by a C1-3-alkyl, C5-7-cycloalkyl or phenyl group and/or the methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be substituted by a hydroxy, hy- droxy-C1-3-alkyl, C1-3-alkoxy or C1-3-alkoxy-C1-3-alkyl group, in each case the methylene group in the 3 or 4 position of a 6- or 7- membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C1-3-alkyl, C1-3-alkoxy, C1-3-alkoxy-C1-3-alkyl, C1-4-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di-(C1-3-alkyl)-aminocarbonyl, phenyl-C1-3-alkylamino or N-(C1-3-alkyl)-phenyl-C1-3-alkylamino group or may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl-), -N(phenyl), -N(phenyl-C1-3-alkyl-), -N(C1-3-alkyl-carbonyl-), -N(C1-3-alkoxy-carbonyl-), -N(benzoyl-) or -N(phenyl-C1-3-alkyl-carbonyl-) group, wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5- to 7-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group, a compound of general formula wherein R3, R5 and X are defined as in claims 1 to 3, R2 has the meanings given for R2 in claims 1 to 3, also denote a bond to a solid phase optionally formed via a spacer and the other one of the groups R2 and R18 has the abovementioned meanings, A denotes a Ci-4-alkyl group and Z2 denotes a leaving group, is reacted with an amine of general formula H—R7, (XII), wherein R7 has the meanings given for R7 hereinbefore, and subsequently, if necessary, any protecting group used for the nitrogen atom of the lactam group is cleaved, or a compound thus obtained is cleaved from a solid phase, and subsequently, if desired, a compound of general formula I thus obtained which contains an alkoxycarbonyl group is converted by hydrolysis into a corresponding carboxy compound, or a compound of general formula I thus obtained which contains an amino or alkylamino group is converted by reductive alkylation into a corresponding alkylamino or dialkylamino compound, or a compound of general formula I thus obtained which contains an amino or alkylamino group is converted by acylation or sulphonation into a corresponding acyl or sulphonyl compound or a compound of general formula I thus obtained which contains a carboxy group is converted by esterification or amidation into a corresponding ester or aminocarbonyl compound or a compound of general formula I thus obtained which contains a cycloalkyleneimino group wherein a methylene group is replaced by a sulphur atom is converted by oxidation into a corresponding sulphinyl or sulphonyl compound, or a compound of general formula I thus obtained which contains a nitro group is converted by reduction into a corresponding amino compound, or a compound of general formula I thus obtained wherein R4 denotes a phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group is converted, by reaction with a corresponding cyanate, isocyanate or carbamoyl halide, into a corresponding ureacompound of general formula I Ri8 denotes a hydrogen atom or a protecting group for the nitrogen atom of the lactam group, wherein one of the groups R2 and R18 may a compound of general formula I thus obtained wherein R4 denotes a phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group is converted, by reaction with a corresponding compound which transfers the amidino group or by reaction with a corresponding nitrile, into a corresponding guanidino compound of general formula I, or if necessary any protecting group used during the reactions to protect reactive groups is cleaved or subsequently, if desired, a compound of general formula I thus obtained is resolved into the stereoisomers thereof or a compound of general formula I thus obtained is converted into the salts thereof, particularly, for pharmaceutical use, into the physiologically acceptable salts thereof with an inorganic or organic acid or base. Dated this 26th day of April, 2007. (SHUKADEV KHURAIJAM) OF REMFRY & SAGAR ATTORNEY )FOR THE APPLICANTS

Full Text

FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
&
THE PATENTS RULES, 2006
COMPLETE SPECIFICATION [See Section 10; rule 13]
"INDOLINONES OF GENERAL FORMULA I"
BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG., a German company of 55216 Ingelheim am Rhein, Germany,
GRANTED
25-06-2007
The following specification particularly describes the invention and the manner in which it is to be performed:

The present invention relates to new indolinones of general formula

(I),

substituted in the 6 position, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof which have valuable properties.
The above compounds of general formula I wherein R^ denotes a hydrogen atom or a prodrug group have valuable pharmacological properties, in particular an inhibiting effect on various kinases, especially receptor tyrosine kinases such as VEGFR2, PDGFRa, PDGFRP, FGFR1, FGFR3, EGFR, HER2, IGF1R and HGFR, as well as complexes of CDK"s (Cyclin Dependent Kinases) such as CDK1, CDK2, CDK3, CDK4, CDK5, CDK6, CDK7, CDK8 and CDK9 with their specific cyclins (A, Bl, B2, C, Dl, D2, D3, E, F, Gl, G2, H, I" and K) and to viral cyclin (cf. L. Mengtao in J. Virology .71(3), 1984-1991 (1997)), and on the proliferation of cultivated human cells, in particular endothelial cells, e.g. in angiogenesis, but also on the proliferation of other cells, in particular tumour cells.

The other compounds of the above general formula I wherein Rx does not denote a hydrogen atom or a prodrug group are valuable intermediate products for preparing the abovementioned compounds.
The present invention thus relates to the above compounds of general formula I, whereby those compounds wherein Rj_ denotes a hydrogen atom or ,k prodrug group have valuable pharmacological properties, pharmaceutical compositions containing the pharmacologically active compounds, the use thereof and processes for preparing them.
In the above general formula I
X denotes an oxygen or sulphur atom,
Rx denotes a hydrogen atom or a prodrug group such as a Cx.4-alkoxycarbonyl or C2.4-alkanoyl group,
R2 denotes a carboxy group, a straight-chain or branched C^g-alkoxy-carbonyl group, a C4_7-cycloalkoxy-carbonyl or an aryloxycarbonyl group,
a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C^-alkoxy-carbonyl, aminocarbonyl, C-L.-j-alkylamino-carbonyl or di-(C^3-alkyl)-aminocarbonyl group,
a straight-chain or branched C2.6-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, C1.3-alkoxy, amino, C^-alkylamino or di-(Cx„3-alkyl)-amino group,

an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C-^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (C^s-alkyl) -Cj.-j-alkylaminocarbonyl-phenyl group, it may also denote a di- (Cx.2-alkyl) -aminocarbonyl group,
R3 denotes a hydrogen atom, a C^-alkyl, C3_7-cycloalkyl, trifluoromethyl or heteroaryl group,
a phenyl or naphthyl group, a phenyl or naphthyl group mono-or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C^-alkyl or C^-alkoxy group, whilst in the event of disubstitution the substituents may be identical or different and wherein the abovementioned unsubstituted as well as the mono- and disubstituted phenyl and naphthyl groups may additionally be substituted
by a hydroxy, hydroxy-C1_3-alkyl or C^-alkoxy-C^-alkyl group,
by a cyano, carboxy, carboxy-C-^-alkyl,
C^-alkoxycarbonyl, aminocarbonyl, C1.3-alkylamino-carbonyl or di- (C^j-alkyl)-aminocarbonyl group,
by a nitro group,
by an amino, C^-alkylamino, di- (C^-alkyl) -amino or amino-C^.-,-alky 1 group,
by a C^-alkylcarbonylamino, N~ (C1_3-alkyl) -C^-alkyl-
carbonylamino, C1_3-alkylcarbonylamino-C1_3-alkyl,
N- (C1.3-alkyl) -C1.3-alkylcarbonylamino-C1.3-alkyl, C^-alkyl-
sulphonylamino, C^-alkylsulphonylamino-Ci.-j-alkyl,
N- (C^-alkyl) -C^-alkylsulphonylamino-C^-alkyl or
aryl-C^-alkylsulphonylamino group,

by a cycloalkylamino, cycloalkyleneimino, cyclo-alkyleneiminocarbonyl, cycloalkyleneimino-C^-alkyl, cycloalkyleneiminocarbonyl-C^^^-alkyl or
cycloalkyleneiminosulphonyl-C^-alkyl group having 4 to 7 ring members in each case, whilst in each case the methylene group in position 4 of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH or -NCC^-alkyl) group,
or by a heteroaryl or heteroaryl-C^-alky 1 group,
R4 denotes a C3.7-cycloalkyl group,
whilst the methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be substituted by an amino, C^-alkylamino or di- (C^-alkyl) -amino group or replaced by an -NH or -NCC^-alkyl) group,
or a phenyl group substituted by the group R6, which may additionally be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by Cx.5-alkyl, trifluoromethyl, hydroxy, C1.3-alkoxy, carboxy, C1.3-alkoxycarbonyl, amino, acetylamino, C^-alkyl-sulphonylamino, aminocarbonyl, C^-alkyl-aminocarbonyl, di- (C^-alkyl)-aminocarbonyl, aminosulphonyl, C1.3 - alkyl - aminosulphonyl,
di- (C^-alkyl)-aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different and wherein
R6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom,
a cyano, nitro, amino, C^-alkyl, C3_7-cycloalkyl,
trifluoromethyl, phenyl, tetrazolyl or heteroaryl group,

the group of formula

wherein the hydrogen atoms bound to a nitrogen atom may in each case be replaced independently of one another by a C^-alkyl group,
a C1.3-alkoxy group, a C^-alkoxy-C^-alkoxy, phenyl-C10-alkoxy, amino-C2„3-alkoxy, C1_3-alkylamino-C2_3-alkoxy, di- (C^-alkyl) -amino-C2.3-alkoxy, phenyl-C^-alkylamino-C2.3-alkoxy, N- (C^-alkyl) -phenyl-C^-alkylamino-Cj.-j-alkoxy, C5_7-cycloalkyleneimino-C2_3-alkoxy or C-L.-j-alkylmercapto group,
a carboxy, C1.4-alkoxycarbonyl, aminocarbonyl, C1.3-alkyl-amino-carbonyl, N- (C^g-alkyl) -C^-j-alkylaminocarbonyl, phenyl- C^3 -alkylamino-carbonyl, N- (C^-alkyl) -phenyl-C1.3-alkylamino-carbonyl, piperazinocarbonyl or N- (C1.3-alkyl) -piperazinocarbonyl group,
a C^-alkylaminocarbonyl or N- (C^-alkyl) -C1.3-alkylaminocarbonyl group wherein an alkyl moiety is substituted by a carboxy or C^-alkoxycarbonyl group or in the 2 or 3 position by a di- (C^-alkyl) -amino, piperazino, N- (C^-alkyl) -piperazino or a 4- to 7-membered cycloalkyleneimino group,
a C3.7 - eye loalkyl-carbonyl group,
wherein the methylene group in the 4 position of the 6- or 7-membered cycloalkyl moiety may be substituted by an amino, C1.3-alkylamino or di- (C^3-alkyl) -amino group or replaced by an -NH or -NCC^-alkyl) group,

a 4- to 7-membered cycloalkyleneimino group wherein
a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
the cycloalkylene moiety may be fused to a phenyl ring or
one or two hydrogen atoms may each be replaced by a C1_2-alkyl group and/or
in each case the methylene group in the 4 position of a 6-or 7-membered cycloalkyleneimino group may be substituted by a carboxy, Cj._3-alk0xycarb0n.yl, aminocarbonyl, Cj._3-alkylamir.0carb0r.yl, di- (C^j-alkyl) -aminocarbonyl, phenyl-C1_3-alkylatnino or N-(C1.3-alkyl)-phenyl-Cj._3-alkylamino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1_3-alkyl) , -N(phenyl), -N (C^-alkyl-carbonyl) or -N.(benzoyl) group,
a C1_4-alkyl group substituted by the group R7, wherein
R7 denotes a C3.7-cycloalkyl group,
whilst the methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be substituted by an amino, Cj,_3-alkylamino or di- (C1_3-alkyl) -amino group or replaced by an -NH or -N (C1_3-alkyl) group or
in a 5- to 7-membered cycloalkyl group a -(CH2)2 group may be replaced by a -CO-NH group, a -(CH2)3 group may be replaced by a -NH-CO-NH or -CO-NH-CO group or a -(CH2)4 group may be replaced by a -NH-CO-NH-CO group, whilst in each case a hydrogen atom bound to a nitrogen atom may be replaced by a C1_3-alkyl group,

an aryl or heteroaryl group,
a hydroxy or C1.3-alkoxy group,
an amino, C^-alkylamino, di-(C1.7-alkyl)-amino, phenylamino, N-phenyl-C^-alkyl-amino, phenyl-C^.-j-alkyl-amino, N- (C^-alkyl) -phenyl-C^-alkylamino or di-(phenyl-C1.3-alkyl) -amino group,
an co-hydroxy-C2_3-alkyl-amino, N- (C^-alkyl) -co-hydroxy-C2_3-alkyl-amino, di- (co~ hydroxy-C2_3-alkyl) -amino, di- (co- (C^-alkoxy) -C2,3-alkyl) -amino or N~ (dioxolan-2-yl) -C1.3-alkyl-amino group,
a C1^3-alkylcarbonylamino-C2_3-alkyl-amino or C^-alkylcarbonylamino-Cj.-j-alkyl-N- (Cx..3-alkyl) -amino group,
a C1.3-alkylsulphonylamino, N-(C^-alky!)-C^.-j-alkyl-sulphonylamino, C^-alkylsulphonylamino-C^-alkyl-amino or C-^-alkylsulphonylamino-C^-alkyl-N- (C^-alkyl) -amino group,
a hydroxycarbonyl-C1.3-alkylamino or N- (C^-alkyl) -hydroxycarbonyl-Cj^.3-alkyl-amino group,
a guanidino group wherein one or two hydrogen atoms may each be replaced by a C^-alky! group,
a group of formula
-N(R8) -CO- (CH2)n-R9 (ID,
wherein

R8 denotes a hydrogen atom or a C^-alkyl group,
n denotes one of the numbers 0, 1, 2 or 3 and
R9 denotes an amino, C1.4-alkylamino,
di- (C^-alkyl)-amino, phenylamino,
N- (C^-alkyl)-phenylamino, benzylamino,
N-(C^-alkyl)-benzylamino or C^-alkoxy group, a 4- to
7-membered cycloalkyleneimino group, whilst in each
case the methylene group in the 4 position of a 6- or
7-membered cycloalkyleneimino group may be replaced by
an oxygen or sulphur atom, by a sulphinyl, sulphonyl,
-NH, -NCC^-alkyl) , -N(phenyl), -N (C^-alkyl-carbonyl)
or -N(benzoyl) group, or, if n denotes one of the
numbers 1, 2 or 3, it may also denote a hydrogen atom,
a group of formula
-N(R10)-(CH2)m-(C0)o-R11 (III),
wherein
R10 denotes a hydrogen atom, a C1.3-alkyl group, a C1_3-alkylcarbonyl, arylcarbonyl, phenyl-^.3-alkyl-carbonyl, C^j-alkylsulphonyl, arylsulphonyl or phenyl-C1^-alkylsulphonyl group,
m denotes one of the numbers 1, 2, 3 or 4,
o denotes the number 1 or, if m denotes one of the numbers 2, 3 or 4, o may also denote the number 0 and
RX1 denotes an amino, C^-alkylamino, di- (C^-alkyl)-amino, phenylamino, N- (C-^-alkyl) -phenylamino, benzylamino, N-(C2.4-alkyl)-benzylamino, C^-alkoxy or

C^-alkoxy-C-^-alkoxy group, a di- (C^-alkyl) -amino-C^-alkylamino group optionally substituted in the 1 position by a C^-alkyl group or a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1.3-alkyl) , -N(phenyl) , -N(Cl.3-alkyl-carbonyl) or -N(benzoyl) group,
a C4_7-cycloalkylamino, C4_7-cycloalkyl-C1_3-alkylamino or C4.7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond and wherein the abovementioned groups may each additionally be substituted at the amino-nitrogen atom by a C5.7-cycloalkyl, C2.4-alkenyl or C^-alkyl group,
a 4- to 7-membered cycloalkyleneimino group, wherein
the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C^-alkyl, C^-alkoxy or amino group, and/or
one or two hydrogen atoms may each be replaced by a C^-alkyl, Cs.7-cycloalkyl or phenyl group and/or
the methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C^-alkyl, C1_3-alkoxy or Cj.j-alkoxy-C^-alkyl group,
the methylene group in the 3 or 4 position of a 6- or 7-membered cycloalkyleneimino group may in each case be

substituted by a hydroxy, hydroxy-C^3 -alkyl, C^-alkoxy, C1,3-alkoxy-C1.:3-alkyl, carboxy, C1_4 - alkoxycarbonyl, aminocarbonyl,
C^-alkylaminocarbonyl, di- (C^-alkyl) -aminocarbonyl, phenyl-Cj.3-alkylamino or N- (C^-alkyl) -phenyl-C^-alkyl-amino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1.3-alkyl-) , -N (phenyl) , -N(phenyl-C^-alkyl-) , -N(C1^3-alkyl-carbonyl-) , -N(C1.4-hydroxy-carbonyl-) , -N (C^-alkoxy-carbonyl- ) , -N(benzoyl-) or -N(phenyl-C^.3-alkyl-carbonyl-) group,
wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5-to 7-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group,
or R6 denotes a C^-alkyl group which is substituted by a carboxy, Cx.3-alkoxycarbonyl, aminocarbonyl,
C^-alkylaminocarbonyl or di- (C^-alkyl) -aminocarbonyl group or by a 4- to 7-membered cycloalkyleneiminocarbonyl group,
an N- (Cj^-alkyl) -C2_4-alkanoylamino group which is additionally substituted in the alkyl moiety by a carboxy or Cx.3-alkoxycarbonyl group,
a group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),

wherein
R12 denotes a hydrogen atom, a C^-alkyl or C3.7-cycloalkyl
*
group or a C^-alkyl group terminally substituted by a phenyl, heteroaryl, trifluoromethyl, hydroxy, C^-alkoxy, aminocarbonyl, C^-alkylamino-carbonyl, di-(C^4-alkyl)-amino-carbonyl, C-^-alkyl-carbonyl, C^-alkyl-sulphonyl-amino, N- (C1.3-alkyl) -C^,.,--alkyl-sulphonylamino, C1.3-alkyl-amino^ulphonyl or di-(C.^-alkyl)-aminosulphonyl group and
p denotes one of the numbers 0, 1, 2 or 3 and
R13 assumes the meanings of the abovementioned group R7, or, if p denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom,
a group of formula
-N(R14)-(CH2)q-(CO)r-R15 (V),
wherein
R14 denotes a hydrogen atom, a C^-alkyl group, a
C^-alkylcarbonyl, arylcarbonyl, phenyl-C^-alkylcarbonyl,
heteroarylcarbonyl, heteroaryl-C^-alkylcarbonyl,
Ci.4-alkylsulphonyl, arylsulphonyl,
phenyl- Cx.3 -alkylsulphonyl, heteroaryl sulphonyl or
heteroaryl -Cx_3 -alkyl -sulphonyl group,
q denotes one of the numbers 1, 2, 3 or 4,
r denotes the number 1 or, if q is one of the numbers 2, 3 or 4, it may also denote the number 0 and
R15 assumes the meanings of the abovementioned group R7,

a group of formula
-N(R16)-S02-Ri7 (VI), wherein
R16 denotes a hydrogen atom or a C^-alkyl group optionally
terminally substituted by a cyano,
trifluoromethyl-carbonylamino or
N- (C^-alkyl)-trifluoromethyl-carbonyl-amino group and
R17 denotes a Cx_2-alkyl group,
an amino group substituted by a di- (C^-alkyl) -amino-Cx.3-alkyl-carbonyl or di- (G^-alkyl) -amino-Cx_3-alkyl-sulphonyl group and a di- (C^-alkyl) -aminocarbonyl-C1.3-alkyl group,
or an N-(C^-alkyl)-C-^-alkylsulphonylamino or N- (C1.3-alkyl) -phenylsulphonylamino group wherein the alkyl moiety is additionally substituted by a cyano or carboxy group,
wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under R6 may be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by C1_5-alkyl, trifluoromethyl, hydroxy, C^3-alkoxy, carboxy, C1.3-alkoxycarbonyl, aminocarbonyl, C^-alkylamino-carbonyl, di- (C^-alkyl)-amino-carbonyl, aminosulphonyl, Cx.3 -alkyl -aminosulphonyl, di- (Ci.j-alkyl) -aminosulphonyl, C^-alkyl-sulphonylamino, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group,

and
Rs denotes a hydrogen atom or a C^-alkyl group,
wherein by an aryl group is meant a phenyl or naphthyl group optionally mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a cyano, trifluoromethyl, nitro, carboxy, aminocarbohyl, C^-alkyl or C^-alkoxy group and
by a heteroaryl group is meant a monocyclic 5- or 6-membered heteroaryl group optionally substituted by a C^-alkyl group in the carbon skeleton, wherein
the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
the 5-membered heteroaryl group contains an imino group optionally substituted by a C^-alkyl or phenyl-C1.3i-alkyl group, an oxygen or sulphur atom or
an imino group optionally substituted by a C1.3-alkyl or phenyl-^.3-alkyl group or an oxygen or sulphur atom and additionally a nitrogen atom or
an imino group optionally substituted by a C1_3-alkyl or phenyl-Ci.3-alkyl group and two nitrogen atoms,
and moreover a phenyl ring may be fused to the abovementioned monocyclic heterocyclic groups via two adjacent carbon atoms and the bonding takes place via a nitrogen atom or via a carbon atom of the heterocyclic moiety or a fused phenyl ring,
some or all of the hydrogen atoms in the abovementioned alkyl and alkoxy groups or in the alkyl moieties contained in the

above-defined groups of formula I optionally being replaced by fluorine atoms,
the saturated alkyl and alkoxy moieties with more than 2 carbon atoms which are present in the groups defined hereinbefore also include the branched isomers thereof, such as for example the isopropyl, tert.butyl, isobutyl group, unless otherwise stated, and
additionally the hydrogen atom of any carboxy group present or a hydrogen atom bound to a nitrogen atom, e.g. a hydrogen atom of an amino, alkylamino or imino group or a saturated N-heterocycle such as the piperidinyl group, may each be replaced by a group which can be cleaved in vivo.
By a group which can be cleaved in vivo from an imino or amino
group is meant, for example, a hydroxy group, an acyl group such as the benzoyl or pyridinoyl group or a C^^-alkanoyl group such as the formyl, acetyl, propionyl, butanoyl, pentanoyl or hexanoyl group, an allyloxycarbonyl group, a C^^-alkoxycarbonyl group such as the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, tert.butoxycarbonyl, pentoxycarbonyl, hexyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl or hexadecyloxycarbonyl group, a phenyl-C.^-alkoxycarbonyl group such as the benzyloxycarbonyl, phenylethoxycarbonyl or phenylpropoxycarbonyl group, a C^-alkylsulphonyl-C2_4 - alkoxycarbonyl, C^ - alkoxy- C2.4 - alkoxy- C2_4 - alkoxycarbonyl or ReCO-0- (RfCRg) -0-C0 group wherein
Re denotes a C^g-alkyl, C5,7-cycloalkyl, phenyl or phenyl-CJ.J-alkyl group,

R£ denotes a hydrogen atom, a C10-alkyl, C5.7-cycloalkyl or phenyl group and
Rg denotes a hydrogen atom, a C^-alkyl or ReCO-0- (RECRg) -0 group wherein Re to Rg are as hereinbefore defined,
wherein additionally the amino group may be a phthalimido group, whilst the abovementioned ester groups may also be used as a group which cari be converted in vivo into a carboxy
group.
One sub-group of compounds of general formula I which deserves special mention comprises those wherein
X, R1 and R3 to R5 are as hereinbefore defined and
R2 denotes a straight-chain or branched C^.g-alkoxy-carbonyl group, a C4_7-cycloalkoxycarbonyl or a aryloxycarbonyl group,
a straight-chain or branched C^g-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C^-alkoxycarbonyl, aminocarbonyl, C^-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group,
a straight-chain or branched C2„6-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, C^-alkoxy, amino, C^-alkylamino or di- (C1_3-alkyl) -amino group,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
A second sub-group of compounds of general formula I which deserves special mention comprises those wherein

X, R-L and R3 to R5 are as hereinbefore defined and
R2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1.3-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (Ci.s-alkyl) -C^-alkylaminocarbonyl-phenyl group, R2 may also denote a di- (C^-alkyl)-aminocarbonyl group,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
A third sub-group of compounds of general formula I which deserves special mention comprises those wherein
X, Rx to R3 and R5 are as hereinbefore defined and
R4 denotes an R7-(C^-alkyl)-phenyl group, wherein
R7 denotes an amino, C^-alkylamino, di- (C^-alkyl) -amino, phenylamino, N-phenyl-C^3-alkyl-amino, phenyl-C^-alkyl-amino, N- (C^-alkyl) -phenyl-C1.3-alkylamino or di- (phenyl-0^3-alkyl) -amino group,
or a phenyl group substituted by the group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),
wherein R12, p and R13 are as hereinbefore defined,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
Preferred compounds of general formula I are those wherein

Rx and R3 are as hereinbefore defined and
X denotes an oxygen atom,
R2 denotes a carboxy group, a straight-chain or branched C^.g-alkoxy-carbonyl group, a C5_7-cycloalkoxycarbonyl or a phenoxycarbonyl group,
a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C-^-alkoxycarbonyl, aminocarbonyl, C^j-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group,
a straight-chain or branched C2^3-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a chlorine atom, by a hydroxy, C^-alkoxy, amino, C^-alkylamino or di- (C^.j-alkyl) -amino group,
an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N~ (C^-alkyl) -C-L.3-alkylaminocarbonyl-phenyl group, it may also denote a di-(C^-alkyl)-aminocarbonyl group,
R4 denotes a C3.7-cycloalkyl group,
whilst the methylene group in the 4 position of a 6- or 7-membered oycloalkyl group may be substituted by an amino, C^j-alkylamino or di- (C^-alkyl)-amino group or replaced by an -NH or -N(C1_3-alkyl) group,
or a phenyl group substituted by the group R6, which may additionally be mono- or disubstituted by fluorine, chlorine or bromine atoms, by C^-alkyl, trifluoromethyl, hydroxy,

C^-alkoxy, carboxy, C^-alkoxycarbonyl, amino, acetylamino, aminocarbonyl, C1_3 - alkyl - aminocarbonyl,
di-(C^j-alkyl)-aminocarbonyl, nitro or cyano groups, wherein the substituents may be identical or different and wherein
R6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom,
a cyano, nitro, amino, C^.j-alkyl, C3_7-cycloalkyl,
trifluoromethyl, phenyl, tetrazolyl or heteroaryl group,
the group of formula

wherein a hydrogen atom bound to the nitrogen atom may be replaced by a C^-alkyl group,
a C^-alkoxy group, an amino-C2_3-alkoxy, C^-alkylamino-C2.3-alkoxy, di- (C1.3-alkyl) -amino-C2_3-alkoxy, phenyl-C1_3-alkylamino-C2_3-alkoxy, N- (C^-alkyl) -phenyl-C1.3-alkylamino-C2_3-alkoxy, pyrrol idino-C2_3-alkoxy, piperidino-C2_3-alkoxy or C^-alkylmercapto group,
a carboxy, Cw-alkoxycarbonyl, aminocarbonyl, C^.,-alkyl -amino-carbonyl, phenyl -C-^-alkylamino-carbonyl or N- (C-^-alkyl) -phenyl-C1.3-alkylamino-carbonyl group,
a C3_7-cycloalkyl-carbonyl group,
wherein the methylene group in the 4 position of the 6- or 7-membered cycloalkyl moiety may be replaced by an -NH or -N (Cx.3 - alkyl) group,

a 4- to 7-membered cycloalkyleneimino group, wherein
a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
one or two hydrogen atoms may each be replaced by a C^.j-alkyl group and/or
in each case th^ methylene group in the 4 position of a 6-or 7-membered cycloalkyleneimino group may be substituted by a carboxy, C^-alkoxycarbonyl, aminocarbonyl, Cx.3-alkylaminocarbonyl, di- (Cx_3-alkyl) -aminocarbonyl, phenyl-C^-alkylamino or N- (C^-alkyl) -phenyl-Cx_3-alkylamino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH or -N (C^-alkyl) group,
a Cx.4-alkyl group terminally substituted by the group R7, wherein
R7 denotes a C5.7-cycloalkyl group,
whilst the methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be replaced by an -NH or -NlC^j-alkyl) group or
in a 5- to 7-membered cycloalkyl group a -(CH2)2 group may be replaced by a -CO-NH group, a -(CH3)3 group may be replaced by a -NH-CO-NH- or a -(CH2)4 group may be replaced by a -NH-CO-NH-CO group, whilst in each case a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl group,
a phenyl or heteroaryl group,

a hydroxy or C^-alkoxy group,
an amino, C^-alkylamino, di-(C-^-alkyl)-amino, phenylamino, N-phenyl-C^-alkyl-amino,
phenyl-C^-alkylamino, N- (C1_3-alkyl) -phenyl-C^-alkylamino or di- (phenyl-Q.1_3-alkyl) -amino group,
a co-hydroxy-C2^3-alkyl-amino, N- (C^-alkyl) -©-hydroxy--C2_3-alkyl-amino, di- (co-hydroxy-C2.3-alkyl) -amino, di- (00- (C^j-alkoxy) -C2.3-alkyl) -amino or N-(dioxolan-2-yl)-C^-alkyl-amino group,
a C10-alkylcarbonylamino-C2_3-alkyl-amino or C1_3-alkylcarbonylamino-C2_3-alkyl-N- (G^-alkyl) -amino group,
a C^-alkylsulphonylamino, N- (C^-alkyl) -C^-alkylsulphonylamino, Cj^^-alkylsulphonylamino--C2_3-alkyl-amino or C1_3-alkylsulphonylamino-C2_3-alkyl--N- (Ci.j-alkyl) -amino group,
a hydroxycarbonyl-C1.3-alkylamino or
N- (C^.-j-alkyl) -hydroxycarbonyl-Ci^-alkyl-amino group
a guanidino group wherein a hydrogen atom may be replaced by a C3..3-alkyl group,
a group of formula
-N(R8)-CO-(CH2)n-R9 (II),
wherein
R8 denotes a hydrogen atom or a C^-alkyl group, n denotes one of the numbers 0, 1, 2 or 3 and

R9 denotes an amino, C-^-alkylamino, di- (C^-alkyl) -amino, phenylamino, benzylamino or Cx.4-alkoxy group, a 5- to 7-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an -NH, -N(C1_3-alkyl) , -N(phenyl), -N (C^-alkyl-carbonyl) or -N(benzoyl) group, or, if n denotes one of the numbers 1, 2"or 3, it may also denote a hydrogen atom,
a group of formula
-N(R10)-(CH2)m-(CO)0-R11 (III),
wherein
R10 denotes a hydrogen atom, a C^-alkyl group, a C1.3-alkylcarbonyl or C^j-alkylsulphonyl group,
m denotes one of the numbers 1, 2 or 3,
o denotes the number 1 or, if m is one of the numbers 2 or 3, o may also denote the number 0 and
Rxl denotes an amino, C1.3-alkylamino, di- (C-^-alkyl) -amino, C^4-alkoxy or C1.3-alkoxy-C1.3-alkoxy group or a 5- to 7-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an -NH, -N (C^-alkyl), -N(phenyl), -NCC^-alkyl-carbonyl) or -N(benzoyl) group,
a C4.7-cycloalkylamino or C4_7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond,

a 4- to 7-membered cycloalkyleneimino group, wherein
the cycloalkylene moiety may be fused to a phenyl group or
one or two hydrogen atoms may each be replaced by a C^-alkyl group and/or
the methylene group in position 3 of the pyrrolidine group may be substituted by a hydroxy or C^-alkoxy group,
in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C^-alkyl, C^-alkoxy, carboxy, C1.3-alkoxycarbonyl, aminocarbonyl, C1.3-alkylaminocarbonyl, di- (C^-alkyl) -aminocarbonyl, phenyl-C^-alkylamino or N- (C1.3-alkyl) -phenyl-C1.3-alkyl-amino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N (C^-alkyl) , -N(phenyl), -N (phenyl -C^-alkyl) , -N (Cx_3-alkyl-carbonyl) , -N(C1.4-alkoxy-carbonyl) , -N(benzoyl) or - N (phenyl - C^-j - alkyl - carbonyl) group,
wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5-to 6-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group,

or R6 denotes a C^--alkyl group which is terminally substituted by a carboxy, C^-alkoxycarbonyl, aminocarbonyl, C^.j-alkylaminocarbonyl or di- (C^-alkyl) -aminocarbonyl group or by a 4- to 7-membered cycloalkyleneiminocarbonyl group,
a group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),
wherein
R12 denotes a hydrogen atom, a C1.3-alkyl, Cs.7-cycloalkyl, phenyl-C1_3-alkyl or heteroaryl-Q^-alkyl group and
p denotes one of the numbers 0, 1, 2 or 3 and
R13 assumes the meanings of the abovementioned group R7, or, if p denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom,
a group of formula
-N(Ri4)-(CH2)q-(CO)r-Rxs (V),
wherein
R14 denotes a hydrogen atom, a C^-alkyl group, a C^-alkylcarbonyl, phenylcarbonyl, phenyl-C^3-alkyl-carbonyl, heteroarylcarbonyl,
heteroaryl - C^ - alkylcarbonyl, Cx.4 -alkylsulphonyl, phenyl sulphonyl, phenyl -C^- alkyl sulphonyl -heteroarylsulphonyl or heteroaryl-Cx_3-alkyl-sulphonyl group,
g denotes one of the numbers 1, 2, 3 or 4,

r denotes the number 1 or if q is one of the numbers 2, 3 or 4, it may also denote the number 0 and
R15 assumes the meanings of the abovementioned group R7,
a group of formula
-N(R16)-S02-Ri7 (VI), wherein
R16 denotes a hydrogen atom or a C^-alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino or N- (C1.3-alkyl) -trifluoromethyl--carbonyl-amino group and
R17 denotes a C^-alkyl group,
an amino group substituted by a di- (C^-alkyl) -amino-^.3-alkyl-carbonyl or di- (C1.3-alkyl) -amino-C^-alkyl-sulphonyl group and a di- (C^-alkyl) -aminocarbonyl-C^.j-alkyl group,
wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under RG may be mono-or disubstituted by fluorine, chlorine or bromine atoms, by C^-alkyl, trifluoromethyl, hydroxy, C^-alkoxy, carboxy, C^j-alkoxycarbonyl, aminocarbonyl, C^-alkyl-aminocarbonyl, aminosulphonyl, C^-alkyl-aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group, and
Rs denotes a hydrogen atom or a C^-alkyl group,

whilst by a heteroaryl group as mentioned above is meant a pyridinyl, pyrazinyl, pytimidinyl, pyridazinyl, pyrrolyl, furyl, thienyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl or triazolyl group optionally substituted in the carbon skeleton by a C^-alkyl group wherein a hydrogen atom bound to a nitrogen atom may be replaced by a C1.3-alkyl or phenyl-C,^,-alkyl group and wherein the 5-membered heteroaryl groups containing at least one imino group are bound via a carbon or nitrogen Atom,
a hydrogen atom bound to a nitrogen atom in the abovementioned groups may be replaced by a group which can be cleaved in
vivo, particularly by an acetyl or tert.butoxycarbonyl group,
the carboxy groups contained in the abovementioned groups may each be substituted by a group which can be cleaved in vivo
and may occur, for example, in the form of the tert.butoxycarbonyl group,
some or all of the hydrogen atoms in the abovementioned alkyl and alkoxy groups or in the alkyl moieties contained in the above-defined groups of formula I optionally being replaced by fluorine atoms and
the saturated alkyl and alkoxy moieties contained in the abovementioned groups, which contain more than 2 carbon atoms, may be straight-chain or branched, unless otherwise stated,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
One subgroup of preferred compounds of general formula I deserving- special mention comprises those wherein
X, Rx and R3 to R5 are as hereinbefore defined and •

R2 denotes a straight-chain or branched C^-alkoxy-carbonyl group, a Cs_7-cycloalkoxycarbonyl or a phenoxycarbonyl group,
a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl-carboxy, C^-alkoxycarbonyl, aminocarbonyl, C^-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group,
a straight-chain or branched C2.3-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a hydroxy, C^.j-alkoxy, amino, C^-alkylamino or di- (C^-alkyl) -amino group,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
A second sub-group of preferred compounds of general formula I deserving special mention comprises those wherein
X, Rx and R3 to R5 are as hereinbefore defined and
R2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N-(C^-alkyl)-C^-alkylaminocarbonyl-phenyl group, R2 may also denote a di- (C1.2-alkyl) -aminocarbonyl group,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
A third sub-group of preferred compounds of general formula I deserving special mention comprises those wherein
X, Rx to R3 and R5 are as hereinbefore defined and

R„ denotes an R7- (n-C^-alkyl) -phenyl group, wherein
R7 denotes an amino, C^.g-alkylamino, di- (C^.g-alkyl) -amino, phenylamino, N-phenyl-C1.3-alkyl-amino, phenyl -C1_2- alkyl -amino, N- (C^-alkyl) -phenyl-C1.3-alkylamino or di-(phenyl-Ca.3-alkyl) -amino group,
or a phenyl group substituted by the group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),
wherein R12, p and R13 are as hereinbefore defined,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
Particularly preferred compounds of general formula I are those wherein
X denotes an oxygen atom,
R-L denotes a hydrogen atom,
R2 denotes a carboxy group, a straight-chain or branched C1.4-alkoxycarbonyl group or a phenoxycarbonyl group,
a straight-chain or branched C^-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a phenyl, carboxy, C1.3-alkoxycarbonyl, aminocarbonyl, C1.3-alkylaminocarbonyl or di- (C^-alkyl) -aminocarbonyl group,
a straight-chain or branched C2.3-alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a hydroxy,

C10-alkoxy, amino, C^-alkylamino or di- (C1.3-alkyl) -amino group,
an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C^-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (Ci^-alkyl) -CVj-alkylaminocarbonyl-phenyl group, it may also denote a di- (C^-alkyl)-aminocarbonyl group,
R3 denotes a C^-alkyl group or a phenyl group which may be substituted by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C1_3-alkyl, hydroxy or C1_3-alkoxy group,
R4 denotes a Cs_6-cycloalkyl group,
wherein the methylene group in position 4 of the cyclohexyl group may be substituted by an amino, C^-alkylamino or di- (C^-alkyl)-amino group or replaced by an -NH or -N(C1.3-alkyl) group,
a phenyl group, a phenyl group disubstituted by C^-alkyl, C1_3-alkoxy or nitro groups, wherein the substituents may be identical or different, or
a phenyl group substituted by the group R6, which may additionally be substituted by a fluorine, chlorine or bromine atom or by an amino or nitro group, wherein R6 denotes a fluorine, chlorine or bromine atom,
a C^-alkyl, C1.3-alkoxy, nitro, amino or C5.6-cycloalkyl group,
a pyrrolyl, pyrazolyl, imidazolyl, triazolyl or tetrazolyl group bound via a carbon atom, wherein the abovementioned heteroaromatic groups in the carbon skeleton may be

substituted by a C1.3-alkyl group or a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl or phenyl-Cj.-j-alkyl group,
the group of formula

a carboxy, C^-alkoxycarbonyl, phenyl-C^-alkylamino-carbonyl or C5.7-cycloalkyl-carbonyl group,
a 5 or 6-membered cycloalkyleneimino group, wherein
the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an -NH or -N (C^-alkyl) group,
an unbranched C^-alkyl group terminally substituted by the group R7, wherein
R7 denotes a C5.7-cycloalkyl group,
wherein in a 5 or 6-membered cycloalkyl group a -(CH2)2 group may be replaced by a -CO-NH group, a -(CH2)3 group may be replaced by an -NH-CO-NH- or a -(CH2)4 group may be replaced by an -NH-CO-NH-CO group, whilst in each case a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl group,
a phenyl or pyridinyl group or a pyrrolyl, pyrazolyl, imidazolyl or triazolyl group bound via a carbon or nitrogen atom, wherein the abovementioned heteroaromatic groups in the carbon skeleton may be substituted by a

C^-alkyl group or a hydrogen atom bound to a nitrogen atom may be replaced by a C^-alkyl group,
a hydroxy or C^-alkoxy group,
an amino, C^g-alkylamino, di- (C^g-alkyl) -amino, phenylamino, N-phenyl-C^-alkylamino, phenyl-G^-alkylamino or N- (C^-alkyl) -phenyl-C1_3-alkylamino group,
a co-hydroxy-C2_3-alkyl-amino,
N- (C^-j-alkyl) -co-hydroxy~C2_3-alkylamino,
di- (co-hydroxy-C2.3-alkyl) -amino or
di- (co- (C^-alkoxy) -C2_3-alkyl) -amino group,
a C1.3-alkylcarbonylamino-C2.3-alkyl-amino or C1.3-alkylcarbonylamino-C2.3-alkyl-N- (C^-alkyl) -amino group,
a C^-alkylsulphonylamino, N- (C^-alky!) -C1.3-alkylsulphonylamino, C-^-alkylsulphonylamino--C2.3-alkylamino or C^-alkylsulphonylamino--C2_3-alkyl-N- (C1.3-alkyl) -amino group,
a hydroxycarbonyl-C1_3-alkylamino or
N- (C-^-alkyl) -hydroxycarbonyl-C-L.-j-alkyl-amino group,
a guanidino group wherein a hydrogen atom may be replaced by a C^-alkyl group,
a group of formula
-N(R8)-CO-(CH2)n-R9 (ID, wherein

R8 denotes a hydrogen atom or a C^-alkyl group,
n denotes one of the numbers 0, 1, 2 or 3 and
R9 denotes an amino, C^-alkylamino,
di- (C^3-alkyl) -amino or C^-alkoxy group, a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH, -N (C^-alkyl) or -N(C1.3-alkyl-carbonyl) group, or, if n denotes one of the numbers 1, 2 or 3, R9 may also denote a hydrogen atom,
a group of formula
-N(R10)-(CH2)m-(CO)0-R11 (III),
wherein
R10 denotes a hydrogen atom or a C^-alkyl group,
m denotes one of the numbers 1, 2 or 3,
o denotes the number 1 or, if m is one of the numbers 2 or 3, o may also denote the number 0 and
RX1 denotes an amino, C1.3-alkylamino,
di- (C^-alkyl) -amino, C^-alkoxy or methoxy-C1.3-alkoxy group or a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH, -N(C1.3-alkyl) or -N (C1.3-alkyl-carbonyl) group,
an azetidino, pyrrolidino, piperidino,
2, 6-dimethyl-piperidino, 3,5-dimethyl-piperidino or
azepino group, wherein

the methylene group in position 3 of the pyrrolidino group may be substituted by a hydroxy group,
the methylene group in position 4 of the piperidino group may be substituted by a hydroxy, hydroxy-C^3-alkyl or C^-alkoxy group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N (C^-alkyl) , -N (C^-alkyl-carbonyl), -N(benzoyl) or -Ntphenyl-C^-alkyl-carbonyl) group,
wherein a methylene group linked to an imino-nitrogen atom of the pyrrolidino, piperidino or piperazino group may be replaced by a carbonyl group,
or R6 denotes a straight-chain C^-alkyl group which is terminally substituted by a carboxy or C^-alkoxy-carbonyl group,
a group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),
wherein
R12 denotes a hydrogen atom, a C^-alkyl or phenyl-Cx.3-alkyl group,
p denotes one of the numbers 0, 1 or 2 and
R13 denotes an amino, C^-alkylamino, di-(C1.4-alkyl)-amino, benzylamino, N-(C^-alkyl)-benzylamino, (^..j-alkoxy-C^-alkylamino, N- (C^-alkyl) -

C1_3-alkoxy-C1.3-alkylamino/ di- (2-methoxy-ethyl) -amino, di- {co-hydroxy-C2_3-alkyl) -amino or aminocarbonyl-methyl-N-(methyl)-amino group,
a pyrrolyl, pyrazolyl or imidazolyl group bound via a nitrogen atom and optionally substituted by a C^-alkyl group,
a pyrrolidino, piperidino, morpholino, thiomorpholino or a piperazino group optionally substituted in the 4 position by a C^-alkyl, phenyl - C^ - alkyl, C^-alkylcarbonyl or C^-alkoxycarbonyl group or, if n denotes the number 1 or 2, it may also denote a hydrogen atom,
a group of formula
-N(R14)-(CH2)q-(CO)r-R15 (V),
wherein
R14 denotes a hydrogen atom, a C^-alkyl, C^-alkyl-carbonyl, phenylcarbonyl, phenyl-C^-alkylcarbonyl, furyl-carbonyl, pyridinyl-carbonyl, furyl-C^-alkylcarbonyl, pyridinyl-C^j-alkylcarbonyl, C^-alkylsulphonyl, phenyl sulphonyl or phenyl -Cx_3- alkyl sulphonyl group,
q denotes one of the numbers 1, 2 or 3,
r denotes the number 1 or, if q is one of the numbers 2 or 3, it may also denote the number 0 and
R15 denotes an amino, C^-alkylamino, di- (C^-alkyl) -amino, phenylamino, N- (C^-alkyl) -phenylamino, benzylamino or N-(C^-alkyl)-benzylamino group,or a group of formula

-N(R16)-S02-Ri7 (VI), wherein
R1S denotes a hydrogen atom or a C^-alkyl group optionally
terminally substituted by a cyano,
trifluoromethyl-carbonylamino or
N- (C^-alkyl) -trifluoromethyl-carbonyl-amino group and
R17 denotes a C^-alkyl group,
wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under R6 may be substituted by a fluorine, chlorine or bromine atom, by a methyl," trifluoromethyl, methoxy, nitro or cyano group and
R5 denotes a hydrogen atom,
wherein a hydrogen atom bound to a nitrogen atom in the abovementioned groups may be replaced by an acetyl or tert.butoxycarbonyl group,
the carboxy groups contained in the abovementioned groups may also be present in the form of the tert.butoxycarbonyl precursor group and
the saturated alkyl and alkoxy moieties contained in the abovementioned groups, which contain more than 2 carbon atoms, may be straight-chain or branched, unless otherwise stated,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.

One subgroup of particularly preferred compounds of general formula I deserving special mention comprises those wherein
X, Rx, R3 and R5 are as hereinbefore defined,
R2 denotes a straight-chain or branched C^-alkoxycarbonyl group or a phenoxycarbonyl group,
a straight-chain or"branched C^-alkoxycarbonyl group, which is terminally substituted in the alkyl moiety by a phenyl-carboxy, C1.3-alkoxycarbonyl, aminocarbonyl,
C^-alkylaminocarbonyl or di- (C^-alkyl)-aminocarbonyl group, or
a straight-chain or branched C2_3-alkoxy-carbonyl group, which is terminally substituted in the alkyl moiety by a hydroxy, C^-alkoxy, amino, C-^-alkylamino or di- (C^-alkyl) -amino group, and
R4 denotes an R7- (n-C^-alkyl) -phenyl group, wherein
R7 denotes an amino, C^.j-alkylamino, di- (C^-alkyl) -amino,
co - hydroxy- C2_3- alkyl -amino,
N- (C1„3-alkyl) -co-hydroxy-C2_3-alkyl-amino,
di- (co-hydroxy-C2.3-alkyl) -amino or
di- (co- (C1.3-alkoxy) -C2.3-alkyl) -amino group,
or a phenyl group substituted by the group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),
wherein R12, p and R13 are as hereinbefore defined,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.

A second subgroup of particularly preferred compounds of general formula I deserving special mention comprises those wherein
X, R1 R3 and Rs are as hereinbefore defined,
R2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1-3-alkoxy group or, if R4 does not denote an aminosulphonyl-phenyl or N- (C1-3-alkyl) -C1-3-alkylaminocarbonyl-phenyl group, R2 may also denote a di- (C1-3-alkyl)-aminocarbonyl group and
R4 denotes a R7- (n-C1-3-alkyl) -phenyl group, wherein
R7 denotes an amino, C1-3-alkylamino, di- (C1-4-alkyl) -amino, co-hydroxy-C2-3-alkyl-amino, N- (C1-3-alkyl) -co-hydroxy--C2-3-alkyl-amino, di- (to-hydroxy-C2-3-alkyl) -amino or di- (03- (C1-3-alkoxy) -C2-3-alkyl) -amino group,
or a phenyl group substituted by the group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),
wherein R12, p and R13 are as hereinbefore defined,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
Most particularly preferred compounds of general formula I are those wherein
X denotes an oxygen atom,

R.x and R5 each denote a hydrogen atom,
R2 denotes a methoxycarbonyl, ethoxycarbonyl or aminocarbonyl group,
R3 denotes a phenyl group and
R4 denotes a phenyl group monosubstituted by the group R6, wherein
R6 denotes an N-methyl-imidazol-2-yl group,
an unbranched C^-alkyl group which is terminally substituted by a C^-alkylamino, di-(C^-alkyl)-amino, piperidino or 2,6-dimethyl-piperidino group,
a group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV),
wherein
R12 denotes a C-^-alkyl group,
p denotes one of the numbers 1 or 2 and
R13 denotes a di- (C^-alkyl) -amino group,
or a group of formula
-N(R14)-(CH2)q-(CO)r-R15 (V),
wherein
R14 denotes a C1.3-alkyl-carbonyl or C^-alkylsulphonyl group,

q denotes one of the numbers 1, 2 or 3,
r denotes the number 1 or, if q is one of the numbers 2 or 3, r may also denote the number 0 and
R1S denotes a di- (C^-alkyl) -amino group,
wherein the saturated alkyl moieties contained in the abovementioned groups which contain more than 2 carbon atoms may be straight-chain or branched, unless otherwise stated,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
A subgroup of most particularly preferred compounds of general formula I deserving special mention comprises those wherein
X, R^ R3 and R5 are as hereinbefore defined, R2 denotes a methoxycarbonyl or ethoxycarbonyl group and R4 denotes a di-(C^-alkyl) - amino-C^-alkylphenyl group or a phenyl group substituted by the group of formula
-N(R12)-CO-(CH2)p-Ri3 (IV) wherein R12l p and R13 are as hereinbefore defined,
the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
The following are mentioned as examples of particularly preferred compounds:

(a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone,
(b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6-carbamoyl-2-indolinone,
(c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone,
(d) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone,

(e) 3-Z-[l-(4-((2,6-dimethyl-piperidin-1-yl)-methyl)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone,
(f) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-ani¬lino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(g) 3-Z- [1- (4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-ani-lino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(h) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(i) 3-Z-[l-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(j) 3-Z-[1-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(k) 3-Z-[1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone,
(1) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone,
(m) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(n) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(o) 3-Z-[l-(4-(N-(3*dimethylamino-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(p) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone,
(q) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(r) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-ani¬lino) -1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone and
(s) 3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
the tautomers, the mixtures and the salts thereof.
Another subgroup of compounds of general formula I comprises
those wherein
X denotes an oxygen or sulphur atom,
RL denotes a hydrogen atom or a prodrug group such as a C^-alkoxycarbonyl or C2.4-alkanoyl group,

R2 denotes a carboxy group, a straight-chain or branched C^g-alkoxycarbonyl group, a C5_7-cycloalkoxycarbonyl or phenyl-C1.3-alkoxycarbonyl group, an aminocarbonyl or C^-alkylamihocarbonyl group or, if R4 does not denote an aminosulphonyl-phenyl or N- (C^-alkyl) -Cj^.j-alkylaminocarbonyl-phenyl group, a di- (C^-alkyl)-aminocarbonyl group,
R3 denotes a hydrogen atom, a C^-alkyl, C3.7-cycloalkyl, trifluoromethyl or heteroaryl group,
a phenyl or naphthyl group, a phenyl or naphthyl group mono-or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trif luoromethyl, C^-alkyl or C^-alkoxy group, whilst in the event of disubstitution the substituents may be identical or different and wherein the abovementioned unsubstituted as well as the mono- and disubstituted phenyl and naphthyl groups may additionally be substituted
by a hydroxy, hydroxy-C^-alkyl or C^-alkoxy-C^-alkyl group,
by a cyano, carboxy, carboxy-C^-alkyl,
C-^-alkoxycarbonyl, aminocarbonyl, C^-alkylamino-carbonyl or di- (C^-alkyl)-aminocarbonyl group,
by a nitro group,
by an amino, C1_3-alkylamino, di- (C^-alkyl) -amino or amino-C^-alky 1 group,
by a Cj^-alkylcarbonylamino, N- (C^-alkyl) -C^-alkyl-
carbonyl amino, C1.3-alkylcarbonylamino-C1.3-alkyl,
N- (C^-alkyl) -C-L.-j-alkylcarbonylamino-C^-alkyl, Cx.3-alkyl-
sulphonylamino, C1.3-alkylsulphonylamino-C1.3-alkyl,
N- (C1.3-alkyl) -C1.3-alkylsulphonylamino-C1.3-alkyl or
aryl-C^-alkylsulphonylamino group,

by a cycloalkylamino, cycloalkyleneimino, cyclo-alkyleneiminocarbonyl, cycloalkyleneimino-C1-3-alkyl, cycloalkyleneiminocairbonyl-C1-3-alkyl or
cycloalkyleneiminosulphonyl-C1-3-alkyl group having 4 to 7 ring members in each case, whilst in each case the methylene group in position 4 of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH or -N(C1.3-alkyl) group,
or by a heteroaryl or heteroaryl-C1.3-alkyl group,
R4 denotes a C3.7-cycloalkyl group,
whilst the methylene group in the 4 position of a 6- or 7 membered cycloalkyl group may be substituted by an amino, C^.j-alkylamino or di- (C^-alkyl) -amino group or replaced by an -NH or -N (C1.3-alkyl) group,
or a phenyl group substituted by the group Rfi, which may additionally be substituted by a fluorine, chlorine, bromine or iodine atom, by a Cx.5-alkyl, trif luoromethyl, C^-j-alkoxy, carboxy, C1.3-alkoxycarbonyl, aminosulphonyl, nitro or cyano group, wherein
R6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom,
a cyano, nitro, C^-alkyl, C3_7-cycloalkyl, trif luoromethyl, phenyl, tetrazolyl or heteroaryl group,
a C1.3-alkoxy group optionally sunstituted by 1 to 3 fluorine
atoms, a C1.3-alkoxy-C1.3-alkoxy, phenyl-C1.3-alkoxy,
amino-C2.3-alkoxy, C1_3-alkylamino-C2_3-alkoxy,
di- (C^-alkyl) -amino-C2.3-alkoxy, phenyl-C^-alkylamino-

C2-3-alkoxy, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino-C1-3-alkoxy, C5-7-cycloalkyleneimino-C2-3-alkoxy or C1-3-alkylmercapto group,
a carboxy, C1-4-alkoxycarbonyl, aminocarbonyl, C1-3-alkyl-amino-carbonyl, N- (C1-3-alkyl) -C1-3-alkylaminocarbonyl, phenyl-C1-3-alkylamino-carbonyl, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino-carbonyl, piperazinocarbonyl or N- (C1-3-alkyl)-piperazinocarbonyl group,
a C1-3-alkylaminocarbonyl or N- (C1-3-alkyl) -C1-3-alkylaminocarbonyl group wherein an alkyl moiety is substituted by a carboxy or C1-3-alkoxycarbonyl group or is substituted in the 2 or 3 position by a di- (C1-3-alkyl)-amino, piperazino, N- (C1-3-alkyl)-piperazino or a 4- to 7-membered cycloalkyleneimino group,
a 4- to 7-membered cycloalkyleneimino group, wherein
a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
the cycloalkylene moiety may be fused to a phenyl ring or
one or two hydrogen atoms may each be replaced by a C1-3-alkyl group and/or
in each case the methylene group in the 4 position of a 6-or 7-membered cycloalkyleneimino group may be substituted by a carboxy, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di- (C1-3-alkyl) -aminocarbonyl, phenyl-C1-3-alkylamino or N-(C1-3-alkyl)-phenyl-C^-alkylamino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl), -N(phenyl), -N(C1-3-alkyl-carbonyl) or -N (benzoyl) group,
a C1-4-alkyl group which may be substituted
by a hydroxy or C1-3-alkoxy group,
by an amino, C1-3-alkylamino, di- (C1-7-alkyl) -amino, di-N- (C1-3-alkyl) -amino-C2-3-alkylamino,
tri-N,N,N" - (C1-3-alkyl) -amino-C2-3-alkylamino, phenylamino, N-phenyl-C1-3-alkyl-amino, phenyl-C1-3-alkylamino, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino or di-(phenyl-C1-3-alkyl)-amino group,
by a C1-3-alkylcarbonylamino, N-(C1-3-alkyl)-C1-3-alkylcarbonylamino, C1-3-alkoxycarbonyl-C1-3-alkyl amino or N- (C1-3-alkyl) -C1-3-alkoxycarbonyl-C1-3-alkylamino group,
by a C4-7-cycloalkylamino, C1-3-cycloalkyl-C1-3-alkylamino or C4-7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond and wherein the abovementioned groups may each additionally be substituted at the amino-nitrogen atom by a C1-3-alkyl group wherein some or all of the hydrogen atoms are replaced by fluorine atoms, by a C5-7-cycloalkyl, C2-4-alkenyl or Cl-4-alkyl group,
by a 4- to 7-membered cycloalkyleneimino group, wherein
a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C1-3-alkyl, C1-3-alkoxy or amino group or

one or two hydrogen atoms may each be replaced by a C1-3-alkyl, C5-7-cycloalkyl or phenyl group and/or
in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, carboxy, C1-4-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl,
di- (C1-3-alkyl) -aminocarbonyl, phenyl-C1-3-alkylamino or N- (C1-3-alkyD"-phenyl-C1-3-alkylamino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N (C1-3-alkyl), -N(phenyl), -N(C1-3-alkyl-carbonyl) or -N(benzoyl) group,
by a carboxy, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl or di- (C1-3-alkyl) -aminocarbonyl group or
by a 4- to 7-membered cycloalkyleneiminocarbonyl group,
an amino, pyrrolidino, piperidino, morpholino, benzoylamino or N- (C1-3-alkyl)-benzoylamino group,
an N- (C1-3-alkyl) -C2-4-alkanoylamino group which is additionally substituted in the alkyl moiety by a carboxy or C1-3-alkoxycarbonyl group,
a group of formula
-N(R8)-CO-(CH2)n-R9 (II), wherein
R8 denotes a hydrogen atom or a C1-3-alkyl group,
n denotes one of the numbers 0, 1, 2 or 3 and

R9 denotes an amino, C1-4-alkylamino, phenylamino,
N- (C1-4-alkyl) -phenylamino, benzylamino,
N~ (C1-4-alkyl) -benzylamino or di- (C1-4-alkyl) -amino group, a
4- to 7-membered cycloalkyleneimino group, whilst in each
case the methylene group in the 4 position of a 6- or 7-
membered cycloalkyleneimino group may be replaced by an
oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH,
-N(C1-3-alkyl) , -N (phenyl) , -N(C1-3-alkyl-carbonyl) or
-N(benzoyl) group, or, if n denotes one of the numbers 1,
2 or 3, it may also denote a hydrogen atom,
a group of formula
-N(R10)-(CH2)m-(C0)o-R11 (III),
wherein
R10 denotes a hydrogen atom, a C1-3-alkyl group, a C1-3-alkylcarbonyl, arylcarbonyl, phenyl - C^ - alkylcarbonyl, C1-3-alkylsulphonyl, arylsulphonyl or phenyl-C1-3-alkylsulphonyl group,
m denotes one of the numbers 1, 2, 3 or 4,
o denotes one of the numbers 0 or 1 and
R11 denotes an amino, C1-3-alkylamino, phenylamino, N- (C1-3-alkyl)-phenylamino, benzylamino,
N- (C1-4-alkyl) -benzylamino or di- (C1-4-alkyl) -amino group, a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl) , -N(phenyl) , -N (C1-3-alkyl-carbonyl) or

-N(benzoyl) group, a C1-3-alkoxy group or a
di- (C1-4-alkyl) -amino-C1-3-alkylamino group optionally
substituted in the 1 position by a C1-3-alkyl group,
or an N-(C1-3-alkyl)-C1-3-alkylsulphonylamino or N- (C1-3-alkyl)-phenylsulphonylamino group wherein the alkyl moiety is additionally substituted by a cyano or carboxy group,
wherein all the single-bonded or fused phenyl groups contained in the groups mentioned under R6 may be mono- or disubstituted by fluorine, chlorine, bromine or iodine " atoms, by C1-5-alkyl, trifluoromethyl, C1-3-alkoxy, carboxy, C1-3-alkoxycarbonyl, aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group,
and
R5 denotes a hydrogen atom or a C1-3-alkyl group,
wherein by an aryl group is meant a phenyl or naphthyl group optionally mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C1-3-alkyl or C1-3-alkoxy group and
by a heteroaryl group is meant a monocyclic 5- or 6-membered heteroaryl group optionally substituted by a C1-3-alkyl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted by a C1-3-alkyl group, an oxygen or sulphur atom or an imino group optionally substituted by a C1-3-alkyl group and an oxygen or sulphur -atom or one or two nitrogen atoms, and moreover a phenyl ring may

be fused to the abovementioned monocyclic heterocyclic groups via two adjacent carbon atoms,
the saturated alkyl and alkoxy moieties present in the groups defined above which contain more than 2 carbon atoms also include the branched isomers thereof such as, for example, the isopropyl, tert.butyl or isobutyl group, unless otherwise stated, and
additionally any carboxy, amino or imino group present may be substituted by a group which can be cleaved in vivo,
the isomers and the salts thereof.
According to the invention the new compounds are obtained, for example, by the following methods known in principle from the literature:
a. reacting a compound of general formula

(VII),
wherein
X and R3 are as hereinbefore defined,
R2" has the meanings given for R2 hereinbefore,
Rie denotes a hydrogen atom or a protecting group for the
nitrogen atom of the lactam group, wherein one of the groups
R2" and R18 may also denote a bond to a solid phase optionally
formed via a spacer and the other one of the groups R2" and R18

has the abovementioned meanings, and Z1 denotes a halogen atom, a hydroxy, alkoxy or aryl-alkoxy group, e.g. a chlorine or bromine atom, a methoxy, ethoxy or benzyloxy group,
with an amine of general formula

wherein
R4 and R5 are as hereinbefore defined,
and if necessary subsequently cleaving any protecting group
used for the nitrogen atom of the lactam group or cleaving
from a solid phase.
The protecting group for the nitrogen atom of the lactam group may be, for example, an acetyl, benzoyl, ethoxycarbonyl, tert.butyloxycarbonyl or benzyloxycarbonyl group and
the solid phase may be a resin such as a
4-(2",4"-dimethoxyphenylaminomethyl)-phenoxy resin, the bond preferably being formed via the amino group, or a p-benzyloxybenzyl alcohol resin, wherein the bond is conveniently formed via an intermediate member such as a 2,5-dimethoxy-4-hydroxy-benzyl derivative.
The reaction is conveniently carried out in a solvent such as dimethylformamide, toluene, acetonitrile, tetrahydrofuran, dimethylsulphoxide, methylene chloride or mixtures thereof, optionally in the presence of an inert base such as triethylamine, N-ethyl-diisopropylamine or sodium hydrogen carbonate at temperatures between 20 and 175°C, whilst any protecting group used can be cleaved at the same time by transamidation.

If 21 in a compound of general formula VII denotes a halogen atom, the reaction is preferably carried out in the presence of an inert base at temperatures of between 20 and 120°C.
If Zx in a compound of general formula VII denotes a hydroxy, alkoxy or arylalkoxy group, the reaction is preferably carried out at temperatures between 2 0 and 200°C.
If a protecting group used subsequently has to be cleaved, this is conveniently done either hydrolytically in an aqueous or alcoholic solvent, e.g. in methanol/water, ethanol/water, isopropanol/water, tetrahydrofuran/water, dioxan/water, dimethylformamide/water, methanol or ethanol in the presence of an alkali metal base such as lithium hydroxide, sodium hydroxide or potassium hydroxide at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50°C,
or advantageously by transamidation with an organic base such as ammonia, butylamine, dimethylamine or piperidine in a solvent such as methanol, ethanol, dimethylformamide and the mixtures thereof or in an excess of the amine used, at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50°C.
Cleaving from any solid phase used is preferably carried out using trifluoroacetic acid and water at temperatures between 0 and 35°C, preferably at ambient temperature.
b. In order to prepare a compound of general formula I wherein R2 has the meanings given hereinbefore, with the exception of the carboxy group:
reacting a compound of general formula

(IX)

wherein
R± and R3 to R5 are as hereinbefore defined, or the reactive
derivatives thereof, with a compound of general formula
(X) ,
wherein
R19 denotes a C^-alkanol, a C4.7-cycloalkanol or an aromatic
alcohol,
a C^.g-alkanol which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C^-alkoxy-carbonyl, aminocarbonyl, C^-alkylamino-carbonyl or di- (C^-alkyl) -aminocarbonyl group,
a C2_6-alkanol which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, Cx^3-alkoxy, amino, C1_3-alkylamino or di- (C^-alkyl) -amino group,
an amino or methylamino group, an ethylamino group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1_3-alkoxy group or a di- (C^-alkyl) -amino group.
The esterification or amidation is preferably carried out in a solvent such as methylene chloride, diethylether, tetrahydrofuran, toluene, dioxan, acetonitrile, dimethylsulphoxide or dimethylformamide, optionally in the presence of an inorganic or a tertiary organic base,

preferably at temperatures between 20°C and the boiling temperature of the solvent used. The reaction with a corresponding acid is preferably carried out in the presence of a dehydrating agent, e.g. in the presence of isobutyl chloroformate, tetraethyl orthocarbonate, trimethyl orthoacetate, 2,2-dimethoxypropane, tetramethoxysilane, thionylchloride, trimethylchlorosilane, phosphorus trichloride, phosphorus pentoxide, N,N"-dicyclohexylcarbodiimide, N,N"-dicyclohexyl-carbodiimide/N-hydroxysuccinimide, N,N"-dicyclohexyl-carbodiimide/l-hydroxy-benzotriazole, 2-(lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-tetrafluoroborate, 2-(1H-benzotriazol-l-yl)-1,1,3,3-tetramethyluronium-tetraf luoroborate/l-hydroxy-benzotriazole, N,N"-carbonyldiimidazole or triphenylphosphine/carbon tetrachloride, and optionally with the addition of a base such as pyridine, 4-dimethylaminopyridine, N-methyl-morpholine or triethylamine, conveniently at temperatures between 0 and 150°C, preferably at temperatures between 0 and 100°C, and the acylation with a corresponding reactive compound such as an anhydride, ester, imidazolide or halide thereof, is optionally carried out in the presence of a tertiary organic base such as triethylamine, N-ethyl-diisopropylamine or N-methyl-morpholine at temperatures between 0 and 150°C, preferably at temperatures between 50 and 100°C.
c. In order to prepare a compound of general formula I, wherein R4 denotes a C1-4-alkyl group substituted by the group R7, wherein
R7 denotes an amino, C1-7-alkylamino, di-(C1-7-alkyl)-amino, phenylamino, N-phenyl-C1-3-alkyl-amino, phenyl-C1-3-alkyl-amino, N- (C1-3-alkyl) -phenyl-C1-3-alkylamino or di- (phenyl-C1-3-alkyl) -amino group,

a co-hydroxy-C2_3-alkyl-amino,
N- (C1-3-alkyl) -co-hydroxy-C2-3-alkyl-amino,
di- (co~ hydroxy-C2-3-alkyl) -amino,
di- (co- (C1-3-alkoxy) -C2-3-alkyl) -amino or
N-(dioxolan-2-yl)-C^-alkyl-amino group,
a C1.3-alkylcarbonylamino-C2_3-alkyl-amino or C1.3-alkylcarbonylamino-C2.3-alkyl-N- (C1.3-alkyl) -amino group,
a C1.3-alkylsulphonylamino, N- (C1.3-alkyl) -
C^-alkyl sulphonylamino,
C^3 -alkyl sulphonyl amino -C2.3-alkyl- amino or
C1_3-alkylsulphonylamino-C2.3-alkyl-N- (C^-alkyl) -amino
group,
a group of formula
-N(R10) - (CH2)ra- (C0)o-Rn (III) ,
wherein
R10 denotes a hydrogen atom, a C^-alky! group, a C^-alkylcarbonyl, arylcarbonyl, phenyl-C^-alkyl-carbonyl, C^- alkyl sulphonyl, arylsulphonyl or phenyl-C1.3-alkylsulphonyl group,
m denotes one of the numbers 1, 2, 3 or 4,
o denotes the number 1 and
R1X denotes an amino, C^-alkylamino,
di- (C^-alkyl)-amino, phenylamino,
N-(C^-alkyl)-phenylamino, benzylamino,
N- (C^-alkyl) -benzylamino, C^-alkoxy or
C^-alkoxy-C^-alkoxy group, a di- (Cx.4-alkyl) -amino-C^-

alkylamino group optionally substituted in the 1 position by a C1-3-alkyl group, or a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl) , -N(phenyl), -N (C1-3-alkyl-carbonyl) or -N(benzoyl) group,
a C4-7-cycloalkylamino, C4-7-cycloalkyl-C1-3-alkylamino or C4_7-cycloalkenylamino group wherein position 1 of the ring is not involved in the double bond and wherein the abovementioned groups may each additionally be substituted at the amino-nitrogen atom by a Cs_7-cycloalkyl, C2_4-alkenyl or C^-alkyl group,
or a 4- to 7-membered cycloalkyleneimino group, wherein
the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridine pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C1-3-alkyl, C1-3-alkoxy or amino group, and/or
one or two hydrogen atoms may each be replaced by a C1-3-alkyl, C1-3-cycloalkyl or phenyl group and/or
the methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C1-3-alkyl, C1-3-alkoxy or C1-3-alkoxy-C1-3-alkyl group,
in each case the methylene group in the 3 or 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C1-3-alkyl,

C1-3-alkoxy, C1-3-alkoxy-C1-3-alkyl, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di- (C1-3-alkyl)-aminocarbonyl, phenyl-C1-3-alkylamino or N- (C1-3-alkyl)-phenyl-C1-3-alkylamino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl-) , -N(phenyl), -N(phenyl-C1-3-alkyl-) , -N(C1-3-alkyl-carbonyl-) , -N(C1-3-alkoxy-carbonyl-), -N(benzoyl-) or -N (phenyl - C1-3 - alkyl - carbonyl - ) group,
wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5-to 7-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group:
reacting a compound of general formula

(XI),

wherein
R3, R5 and X are as hereinbefore defined,

R,
has the meanings given for R2 hereinbefore,
R1B denotes a hydrogen atom or a protecting group for-the nitrogen atom of the lactam group, wherein one of the groups R2" and R18 may also denote a bond to a solid phase optionallyformed via a spacer and the other one of the groups R2" and R18
has the abovementioned meanings, A denotes a C1-4-alkyl group
and Z2 denotes a leaving group, for example an alkyl or
arylsulphonyloxy group such as the methylsulphonyloxy,
ethylsulphonyloxy, p-toluenesulphonyloxy or
trifluoromethanesulphonyloxy group, with an amine of general
formula
H R7 (XII) ,
wherein
R7, has the meanings given for R7 hereinbefore, and subsequently, if necessary, cleaving any protecting group used for the nitrogen atom of the lactam group, or cleaving from a solid phase.
The reaction is conveniently carried out in a solvent such as methylene chloride, tetrahydrofuran, 1,4-dioxan, toluene, acetonitrile, dimethylsulphoxide, dimethylformamide, dimethyl-acetamide, N-methylpyrrolidone or the mixtures thereof, optionally with the addition of water as a co-solvent and/or with the addition of an inert auxiliary base, e.g. sodium hydrogen carbonate, pyridine, 2,4,6-trimethylpyridine, quinoline, triethylamine, N-ethyldiisopropylamine, N-ethyl-dicyclohexylamine, 1,4-diazabicyclo[2,2,2]octane or 1,8-diazabicyclo[5,4,0]undec-7-ene, at temperatures between -50°C and +100°C, preferably between -10°C and +50°C, while any protecting group, used may be cleaved at the same time by transamidation.
If any protecting group used for the nitrogen atom of the lactam group has to be removed or if the compound has to be cleaved from a solid phase this is carried out as described under method (a) above.If according to the invention a compound of general formula I is obtained which contains an alkoxycarbonyl group, this may be converted by hydrolysis into a corresponding carboxy compound, or
if a compound of general formula I is obtained which contains an amino or alkylamino group, this may be converted by reductive alkylation into a corresponding alkylamino or dialkylamino compound, or
if a compound of general formula I is obtained which contains an amino or alkylamino group, this may be converted by acylation or sulphonation into a corresponding acyl or sulphonyl compound, or
if a compound of general formula I is obtained which contains a carboxy group, this may be converted by esterification or amidation into a corresponding ester or aminocarbonyl compound, or
if a compound of general formula I is obtained which contains a cycloalkyleneimino group wherein a methylene group is replaced by a sulphur atom, this may be converted by oxidation into a corresponding sulphinyl or sulphonyl compound, or
if a compound of general formula I is obtained which contains a nitro group, this may be converted by reduction into a corresponding amino compound, or
if a compound of general formula I is obtained wherein R4 denotes a phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group, this may subsequently be converted, by reaction with a corresponding cyanate, iso-cyanate or carbamoyl halide, into a corresponding urea compound of general formula I, or

if a compound of general formula I is obtained wherein R4 denotes a phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group, this may subsequently be converted, by reaction with a corresponding compound which transfers the amidino group or by reaction with a corresponding nitrile, into a corresponding guanidino compound of general formula I.
The subsequent hydrolysis is preferably carried out in an aqueous solvent, e.g. in water, methanol/water, ethanol/water, isopropanol/water, tetrahydrofuran/water or dioxan/water, in . the presence of an acid such as trifluoroacetic acid, hydrochloric acid or sulphuric acid or in the presence of an alkali metal base such as lithium hydroxide, sodium hydroxide or potassium hydroxide at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50QC.
The subsequent reductive alkylation is preferably carried out in a suitable solvent such as methanol, methanol/water, methanol/water/ammonia, ethanol, ether, tetrahydrofuran, dioxan or dimethylformamide, optionally with the addition of an acid such as hydrochloric acid in the presence of catalytically activated hydrogen, e.g. hydrogen in the presence of Raney nickel, platinum or palladium/charcoal, or in the presence of a metal hydride such as sodium borohydride, lithium borohydride, sodium cyanoborohydride or lithium aluminium hydride at temperatures between 0 and 100°C, preferably at temperatures between 20 and 80°C.
The subsequent acylation or sulphonylation is preferably carried out with the corresponding free acid or a corresponding reactive compound such as the anhydride, ester, imidazolide or halide thereof, preferably in a solvent such as methylene chloride, diethylether, tetrahydrofuran, toluene, dioxan, acetonitrile, dimethylsulphoxide or dimethylformamide,
optionally in the presence of an inorganic or tertiary organic base at temperatures between -20 and 200°C, preferably at temperatures between 20°C and boiling temperature of the solvent used. The reaction with the free acid may optionally be carried out in the presence of an acid-activating agent or a dehydrating agent, e.g. in the presence of isobutyl chloroformate, tetraethyl orthocarbonate, trimethyl orthoacetate, 2,2-dimethoxypropane, tetramethoxysilane, thionyl chloride, trimethylchlorosilane, phosphorus trichloride, phosphorus pentoxide, N,N"-dicyclohexyl-carbodiimide,
N,N"-dicyclohexylcarbodiimide/N-hydroxysuccinimide, N,N"-dicyclohexylcarbodiimide/1-hydroxy-benzotriazole, 2-(lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-tetrafluoroborate, 2-(lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium-tetrafluoroborate/1-hydroxy-benzotriazole, N,N"-carbonyldiimidazole or triphenylphosphine/carbon tetrachloride, and optionally with the addition of a base such as pyridine, 4-dimethylamino-pyridine, N-methyl-morpholine or triethylamine, conveniently at temperatures between 0 and 150°C, preferably at temperatures between 0 and 100°C. The reaction with a corresponding reactive compound may optionally be carried out in the presence of a tertiary organic base such as triethylamine, N-ethyl-diisopropylamine, N-methyl-morpholine or pyridine or by using an anhydride in the presence of the corresponding acid at temperatures between 0 and 150°C, preferably at temperatures between 50 and 100°C.
The subsequent esterification or amidation is conveniently carried out by reacting a corresponding reactive carboxylic acid derivative with a corresponding alcohol or amine as described hereinbefore.
The subsequent oxidation of the sulphur atom is preferably carried out in a solvent or mixture of solvents, e.g. in water, water/pyridine, acetone, methylene chloride, acetic

sodium periodate or potassium permanganate in acetic acid, water/sulphuric acid or in acetone at 0 to 20°C.
The subsequent reduction of a nitro group is preferably carried out by hydrogenolysis, e.g. with hydrogen in the presence of a catalyst such as palladium/charcoal or Raney nickel in a solvent such as methanol, ethanol, ethyl acetate, dimethylformamide, dimethylformamide/acetone or glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid or glacial acetic acid at temperatures of between 0 and 50°C, but preferably at ambient temperature, and at a hydrogen pressure of 1 to 7 bar, but preferably 3 to 5 bar.
The subsequent preparation of a corresponding urea compound of general formula I is conveniently carried out with an inorganic cyanate or a corresponding isocyanate or carbamoylchloride, preferably in a solvent such as dimethylformamide and optionally in the presence of a tertiary organic base such as triethylamine at temperatures between 0 and 50°C, preferably at ambient.
The subsequent preparation of a corresponding guanidino compound of general formula I is conveniently carried out by reacting with a compound which transfers the amidino group such as 3,5-dimethylpyrazole-l-carboxylic acid amidine, preferably in a solvent such as dimethylformamide and optionally in the presence of a tertiary organic base such as triethylamine at temperatures of between 0 and 50°C, preferably at ambient temperature.
In the reactions described hereinbefore, any reactive groups present such as carboxy, hydroxy, amino, alkylamino or imino groups may be protected during the reaction by conventional protecting groups which are cleaved again after the reaction.

For example, a protecting group for a carboxyl group may be a trimethylsilyl, methyl, ethyl, tert.butyl, benzyl or tetrahydropyranyl group and
protecting groups for a hydroxy, amino, alkylamino or imino group may be an acetyl, trifluoroacetyl, benzoyl, ethoxycarbonyl, tert.butoxycarbonyl, benzyloxycarbonyl, benzyl, methoxybenzyl or 2,4-dimethoxybenzyl group and additionally, for the amino group, a phthalyl group.
Any protecting group used is optionally subsequently cleaved for example by hydrolysis in an aqueous solvent, e.g. in water, isopropanol/water, tetrahydrofuran/water or dioxan/water, in the presence of a acid such as trifluoroacetic acid, hydrochloric acid or sulphuric acid or in the presence of an alkali metal base such as lithium hydroxide, sodium hydroxide or potassium hydroxide, at temperatures between 0 and 100°C, preferably at temperatures between 10 and 50°C.
However, a benzyl, methoxybenzyl or benzyloxycarbonyl group is cleaved, for example, hydrogenolytically, e.g. with hydrogen in the presence of a catalyst such as palladium/charcoal in a solvent such as methanol, ethanol, ethyl acetate, dimethylformamide, dimethylformamide/acetone or glacial acetic acid, optionally with the addition of an acid such as hydrochloric acid or glacial acetic acid at temperatures between 0 and 50°C, but preferably at ambient temperature, and at a hydrogen pressure of 1 to 7 bar, but preferably 3 to 5 bar.
A methoxybenzyl group may also be cleaved in the presence of an oxidising agent such as cerium(IV)ammonium nitrate in a solvent such as methylene chloride, acetonitrile or

acetonitrile/water at temperatures of between 0 and 50°C, but preferably at ambient temperature.
A 2,4-dimethoxybenzyl group, however, is preferably cleaved in trifluoroacetic acid in the presence of anisole.
A tert.butyl or tert.butyloxycarbonyl group is preferably cleaved by treating with an acid such as trifluoroacetic acid or hydrochloric aci£, optionally using a solvent such as methylene chloride, dioxan, ethyl acetate or ether.
A phthalyl group is preferably cleaved in the presence of hydrazine or a primary amine such as methylamine, ethylamine or n-butylamine in a solvent such as methanol, ethanol, isopropanol, toluene/water or dioxan at temperatures between 2 0 and 5 0°C.
Moreover, chiral compounds of general formula I obtained may be resolved into their enantiomers and/or diastereomers.
Thus, for example, the compounds of general formula I obtained which occur as racemates may be separated by methods known per
se (cf. Allinger N. L. and Eliel E. L. in "Topics in
Stereochemistry", Vol. 6, Wiley Interscience, 1971) into their optical antipodes and compounds of general formula I with at least 2 asymmetric carbon atoms may be resolved into their diastereomers on the basis of their physical-chemical differences using methods known per se, e.g. by chromatography
and/or fractional crystallisation, and, if these compounds are obtained in racemic form, they may subsequently be resolved into the enantiomers as mentioned above.
The enantiomers are preferably separated by column separation on chiral phases or by recrystallisation from an optically active solvent or by reacting with an optically active

be obtained by methods known from the literature or may be obtained by the methods described hereinbefore and in the Examples. For example, the compounds of general formula VI are described in German Patent Application 198 24 922.5. Moreover, the compounds of general formula XI may be obtained from the compounds of general formula I wherein R4 denotes a C^-alkyl-phenyl group substituted in the alkyl moiety by a hydroxy group, for example, by reacting with alkyl- or arylsulphonyl chlorides.
As already mentioned, the new compounds of general formula I wherein Rj_ denotes a hydrogen atom or a prodrug group have valuable pharmacological properties, particularly inhibitory effects on various kinases, especially on receptor-tyrosine kinases such as VEGFR2, PDGFRa, PDGFRp, FGFR1, FGFR3, EGFR, HER2, IGFIR and HGFR, as well as on complexes of CDK"s (Cyclin Dependent Kinases) such as CDK1, CDK2, CDK3, CDK4, CDK5, CDK6, CDK7, CDK8 and CDK9 with their specific cyclins (A, Bl, B2, C, Dl, D2, D3, E, F, Gl, G2, H, I and K) and on viral cyclin, on the proliferation of cultivated human cells, particularly endothelial cells, e.g. in angiogenesis, but also on the proliferation of other cells, particularly tumour cells.
The biological properties of the new compounds were tested by the following standard procedure, as follows:
Human umbilical endothelial cells (HUVEC) were cultivated in IMDM (Gibco BRL)," supplemented with 10 % foetal calf serum (FBS) (Sigma) , 50 pcM of fi-mercaptoethanol (Fluka) , standard antibiotics, 15 ^g/ml of endothelial cell growth factor (ECGS, Collaborative Biomedical Products) and 10 0 /xg/ml of heparin (Sigma) on gelatine-coated culture dishes (0.2 % gelatine, Sigma) at 37°C, under 5 % CO2 in a water-saturated atmosphere.

In order to investigate the inhibitory activity of the compounds according to the invention the cells were starved for 16 hours, i.e. kept in culture medium without growth factors (ECGS + heparin). The cells were detached from the culture dishes using trypsin/EDTA and washed once in serum-containing medium. Then they were seeded out in amounts of 2.5 x 103 cells per well.
The proliferation of the cells was stimulated with 5 ng/ml of VEGFi65 (vascular endothelial growth factor; H. Weich, GBF Braunschweig) and 10 /ig/ml of heparin. As a control, 6 wells in each dish were not stimulated.
The compounds according to the invention were dissolved in 100% dimethylsulphoxide and added to the cultures in various dilutions in triplicate, the maximum dimethyl sulphoxide concentration being 0.3 %.
The cells were incubated for 76 hours at 37°C, then for a further 16 hours 3H-thymidine (0.1 // Ci/well, Amersham) was added in order to determine the DNA synthesis. Then the radioactively labelled cells were immobilised on filter mats and the radioactivity incorporated was measured in a 6-counter. In order to determine the inhibitory activity of the compounds according to the invention the mean value of the non-stimulated cells was subtracted from the mean value of the factor-stimulated cells (in the presence or absence of the compounds according to the invention).
The relative cell proliferation was calculated as a percentage of the control (HUVEC without inhibitor) and the concentration of active substance which inhibits the proliferation of the cells by 50 % (IC50) was determined.

xhe test results of the following compounds (a) to (s) of general formula I are given by way of example:
(a) 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone,
(b) 3-Z- [ (1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]- 6 -carbamoyl-2 -indolinone,
(c) 3-Z- [1-(4-(piperidin-l-yl-methyl) -anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2-indolinone,
(d) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone,

(e) 3-Z- [1-(4- ( (2,6-dimethyl-piperidin-1-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(f) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(g) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino) -1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone,
(h) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone,
(i) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone,
(j) 3-Z-[l-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(k) 3-Z- [1- (4-ethylaminomethyl-anilino) -1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone,

(1) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(m) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(n) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(o) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(p) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone,
(q) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(r) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl) -N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone and
(s) 3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone.

The following Table contains the results found:

Compound IC50 [//m]
(a) 0.04
(b) 0.35
(c) 0.01
(d) 0.02
(e) 0.05
(f) 0.01
(g) 0.003
(h) 0.01
(i) 0.03
(J) 0.02
(k) 0.03
(1) 0.1
(m) 0.02
(n) 0.02
(o) 0.01
(P) 0.02
(q) 0.02
(r) 0.01
(s) 0.04
In view of their inhibitory effect on the proliferation of cells, particularly endothelial cells and tumour cells, the compounds of general formula I are suitable for treating diseases in which the proliferation of cells, particularly endothelial cells, plays a part.
Thus, for example, the proliferation of endothelial cells and the concomitant neovascularisation constitute a crucial stage in tumour progression (Folkman J. et al., Nature 339, 58-61, (1989); Hanahan D. and Folkman J., Cell 86, 353-365, (1996)). Furthermore, the proliferation of endothelial cells is also

important in haemangiomas, in metastasisation, rheumatoid arthritis, psoriasis and ocular neovascularisation (Folkman J., Nature Med. 1, 27-31, (1995)). The therapeutic usefulness of inhibitors of endothelial cell proliferation was demonstrated in the animal model for example by O"Reilly et al. and Parangi et al. (O"Reilly M.S. et al. , Cell 8J., 277-285, (1997); Parangi S. et al. , Proc Natl Acad Sci USA .93., 2002-2007, (1996) ) .
The compounds of general formula I, their tautomers, their stereoisomers or the physiologically acceptable salts thereof are thus suitable, for example, for treating tumours (e.g. plate epithelial carcinoma, astrocytoma, Kaposi"s sarcoma, glioblastoma, lung cancer, bladder cancer, carcinoma of the neck, melanoma, ovarian cancer, prostate cancer, breast cancer, small-cell lung cancer, glioma, colorectal carcinoma, urogenital cancer and gastrointestinal carcinoma as well as haematological cancers, such as multiple myeloma), psoriasis, arthritis (e.g. rheumatoid arthritis), haemangioma, angiofibroma, eye diseases (e.g. diabetic retinopathy), neovascular glaucoma, kidney diseases (e.g. glomerulonephritis), diabetic nephropathy, malignant nephrosclerosis, thrombic microangiopathic syndrome, transplant rejections and glomerulopathy, fibrotic diseases (e.g. cirrhosis of the liver), mesangial cell proliferative diseases, arteriosclerosis and damage to the nerve tissue and also for inhibiting the reocclusion of blood vessels after treatment with a balloon catheter, in vascular prosthetics or after the insertion of mechanical devices for keeping blood vessels open (e.g. stents), or other diseases in which cell proliferation or angiogenesis are involved.
By reason of their biological properties the compounds according to the invention may be used on their own or in conjunction with other pharmacologically active compounds, for example in tumour therapy, in monotherapy or in conjunction

with other anti-tumour therapeutic agents, for example in combination with topoisomerase inhibitors (e.g. etoposide), mitosis inhibitors (e.g. vinblastin, taxol), compounds which interact with nucleic acids (e.g. cis-platin, cyclophosphamide, adriamycin), hormone antagonists (e.g. tamoxifen), inhibitors of metabolic processes (e.g. 5-FU etc.), cytokines (e.g. interferons), kinase inhibitors, antibodies, or in conjunction with radiotherapy, etc. These combinations may be"administered either simultaneously or sequentially.
For pharmaceutical use the compounds according to the invention are generally used for warm-blooded vertebrates, particularly humans, in doses of 0.01-100 mg/kg of body weight, preferably 0.1-20 mg/kg. For administration they are formulated with one or more conventional inert carriers and/or diluents, e.g. with corn starch, lactose, glucose, microcrystalline cellulose, magnesium stearate, polyvinylpyrrolidone, citric acid, tartaric acid, water, water/ethanol, water/glycerol, water/sorbitol, water/polyethylene glycol, propylene glycol, stearyl alcohol, carboxymethylcellulose or fatty substances such as hard fat or suitable mixtures thereof in conventional galenic preparations such as plain or coated tablets, capsules, powders, injectable solutions, ampoules, suspensions, solutions, sprays or suppositories.The Examples which follow are intended to illustrate the invention:
Abbreviations used:
FMOC = 9-fluorenylmethoxycarbonyl
HOBt = 1-hydroxy^lH-benzotriazole
TBTU = 0-benzotriazol-l-yl-N,N,N" ,N" -tetramethyluronium-tetrafluoroborate
DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene
Preparation of the starting compounds:
Solid phase Example I
2.0 g of Rink resin (MBHA resin, made by Messrs Novabiochem) are left to swell in 30 ml of dimethylformamide. Then 40 ml of 30% piperidine in dimethylformamide are added and the mixture is shaken for 7 minutes to cleave the FMOC protecting group. The resin is then washed repeatedly with dimethylformamide. Then 0.4 g of 2-indolinone-6-carboxylic acid (prepared analogously to Langenbeck"et al., Justus Liebigs Ann. Chem. 4 99, 201-208 (1932)), 297 mg HOBt, 706 mg TBTU and 0.9 ml of N-ethyl-diisopropylamine in 30 ml of dimethylformamide are added and the mixture is shaken for 1 hour. Then the solution is suction filtered and the resin is washed five times with 3 0 ml of dimethylformamide and three times with 3 0 ml of methylene chloride. To dry it, nitrogen is blown through the resin. Yield: 1.9 g of charged resinSolid phase example II
1.9 g of the resin obtained in Example I are stirred with 6 ml of acetic anhydride and 6 ml of triethyl orthobenzoate for 3 hours at 110°C. Then the mixture is left to cool and the resin is washed with dimethylformamide and subsequently with methylene chloride. Yield: 1.9 g of moist resin
The following charged resins are prepared analogously to Example II:
(1) resin charged with 3-Z-(1-ethoxy-methylene)-6-carbamoyl-2-
indolinone
Prepared by reacting the resin obtained according to Example I with triethyl orthoformate
(2) resin charged with 3-Z-(1-methoxy-1-methyl-methylene)-6-
carbamoyl-2 -indolinone
Prepared by reacting the resin obtained according to Example I with trimethyl orthoacetate
(3) resin charged with 3-Z-(1-methoxy-l-ethyl-methylene)-6-
carbamoyl-2 -indolinone
Prepared by reacting the resin obtained according to Example" I with trimethyl orthopropionate
(4) resin charged with 3-Z-(1-methoxy-l-propyl-methylene)-6-
carbamoyl-2-indolinone
Prepared by reacting the product of Example I and trimethyl orthobutyrate
Example III
N-(4-nitrophenyl)-N-methyl-methanesulphonamide 3.0 g of N-methyl-4-nitroaniline are dissolved in 2 0 ml of pyridine and 2.4 g of methanesulphonic acid chloride added dropwise at room temperature. The mixture is stirred for 12 hours at room temperature. After this time the mixture is poured onto water, the precipitate formed is filtered off and dried at 50°C in vafcuo.
Yield: 4.0 g (87 % of theory),
Rf value: 0.5 (silica gel, ethyl acetate/toluene = 7:3)
Melting point: 107-108 °C
Example IV
N-(2-dimethylamino-ethvl)-N-methylsulphonyl-4-nitroaniline 38.9 g of N-methylsulphonyl-4-nitroaniline are dissolved in 2.0 1 of acetone, 51.9 g of l-chloro-2-dimethylamino-ethane, 77.4 g of potassium carbonate and 5.0 g of sodium iodide are added and the mixture is stirred for a total of 4 days at 50°C, while after 12 hours a further 25.9 g of l-chloro-2-dimethylamino-ethane, 49.8 g of potassium carbonate and 5.0 g of sodium iodide in 500 ml of acetone are added and after 3 6 hours another 26.0 g of l-chloro-2-dimethylamino-ethane, 50.0 g of potassium carbonate and 5.0 g of sodium iodide in 100 ml of acetone are added. After this time the mixture is filtered and the filtrate evaporated down. The residue is stirred with ether, suction filtered and dried at 40°C. Yield: 25.3 g (49 % of theory),
Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia = 9:1:0.1)
ESI mass spectrum: m/z = 288 [M-t-H+l
The following compounds are prepared analogously to Example IV:
(1) 4- [N-(3-dimethylamino-propyl)-N-methylsulphonyl-amino]-nitrobenzene
(2) N-carboxymethyl-N-methylsulphonyl-4-nitroaniline
(3) N-cyanomethyl-N-methylsulphonyl-p-phenylenediamine
(4) 4- [N- (2- (N-benzyl-N-methyl-amino) -ethyl) -li¬me thyl sulphonyl-amino] -nitrobenzene
(5) 4- [N-(3-phthalimido-2-yl-propyl)-N-methylsulphonyl-amino]-nitrobenzene
(6) 4-[N- (3-(N-benzyl-N-methyl-amino)-propyl)-N-
methylsulphonyl-amino]-nitrobenzene
Example V
N-(dimethylaminocarbonyl-methyl)-N-methylsulphonyl-4-
nitroaniline _____
7.0 g of N-carboxymethyl-N-methylsulphonyl-4-nitroaniline, 2.5 g of dimethylamine hydrochloride, 8.1 g of TBTU and 3.9 g of HOBT are dissolved in 125 ml of dimethylformamide and at 0°C 17.6 ml of N-ethyl-diisopropylamine are added. The mixture is stirred for 4 hours at room temperature, diluted with 1 1 of water and the precipitate formed is suction filtered. After washing with water, ethanol and ether the residue is dried at 70°C in vacuo.
Yield: 5.3 g (69 % of theory),
Rf value: 0.40 (silica gel, methylene chloride/methanol = 9:1)
C11H1SN305S
ESI mass spectrum: m/z = 300 [M-H~]The following compounds are prepared analogously to Example V:
(1) 4-[(N-dimethylaminocarbonylmethyl)-amino] -nitrobenzene
■prepared from 4-(N-carboxymethyl-amino)-nitrobenzene and
dimethylamine hydrochloride
(2) 4-(N-methylaminocarbonylmethyl-N-methylsulphonyl-amino)-
nitrobenzene .,"
Prepared from N-carboxymethyl-N-methylsulphonyl-4-nitroaniline and rnethylamine hydrochloride
(3) 4-[(N-(methylcarbamoyl-methyl)-N-methyl-amino)-methyl]-
nitrobenzene
Prepared from 4-[(N-carboxymethyl-N-methyl-amino)-methyl]-nitrobenzene and rnethylamine hydrochloride
(4) 4-[(N-(dimethylcarbamoyl-methyl)-N-methyl-amino)-methyl]-
nitrobenzene
Prepared from 4-[(N-carboxymethyl-N-methyl-amino)-methyl]-nitrobenzene and dimethylamine hydrochloride
Example VI
4-fN-(2-dimethvlamino-ethvl)-N-acetyl-amino]-nitrobenzene 3.6 g of 4-(2-dimethylamino-ethylamino)-nitrobenzene (according to Gabbay et al., J. Am. Chem. Soc. 91, 5136 (1969)) are dissolved in 50 ml of methylene chloride and 5.0 ml of triethylamine are added. 1.3 ml of acetyl chloride are slowly added dropwise to this mixture at room temperature and the mixture is stirred for 2 hours at room temperature. After this time another 5.0 ml of triethylamine and 1.3 ml of acetylchloride are added and the mixture is refluxed for another 2 hours. The solvent is removed, the residue is taken up in ethyl acetate and the organic phase is extracted twicewith water. After drying over MgS04 the solvent is removed and the residue dried in vacuo.
Yield: 2.0 g (45 % of theory),
Rf value: 0.55 (silica gel, methylene
chloride/methanol/ammonia = 9:1:0.1)
C12H17N303
ESI mass spectrum: m/z = 252 [M+H+]
The following compounds are prepared analogously to Example VI:
(1) 4-[N-(3-dimethylamino-propyl)-N-acetyl-amino]-nitrobenzene
Prepared from 4-(3-dimethylamino-propylamino)-nitrobenzene
(according to Gabbay et al., J. Am. Chem. Soc. 91, 5136 (1969)
and acetyl chloride
(2) 4-[N-(2-dimethylamino-ethyl)-N-propionyl-amino]-
nitrobenzene
Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and propionyl chloride
(3) 4- [N-acetyl-N-(dimethylaminocarbonylmethyl)-amino]-
nitrobenzene
Prepared from 4-[N-(dimethylaminocarbonylmethyl)-amino]-nitrobenzene and acetyl chloride
(4) 4-[N-(2-dimethylamino-ethyl)-N-butyryl-amino]-nitrobenzene Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and butyryl chloride
(5) 4-[N-(2-dimethylamino-ethyl)-N-isobutyryl-amino]-nitrobenzene
Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and isobutyryl chloride

(6) 4-[N-(2-dimethylamino-ethyl)-N-benzoyl-amino]-nitrobenzene Prepared from 4-(2-dimethylamxno-ethylamino)-nitrobenzene and benzoyl chloride
(7) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-1,3-dinitrobenzene
Prepared from 4 -(2-dimethylamino-ethyl-amino)-1,3 -dinitrobenzene and acetyl chloride
(8) 4-[N-(2-dimethylamino-ethyl)-N-(furan-2-carbonyl)-amino]-
nitrobenzene
Prepared from 4-(2-dimethylamxno-ethylamino)-nitrobenzene and furan-2-carbonyl chloride
(9) 4-[N-(2-dimethylamino-ethyl)-N-(2-methoxy-benzoyl)-amino]-
nitrobenzene
Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and 2-methoxy-benzoyl chloride
(10) 4-[N-(2-dimethylamino-ethyl)-N-(pyridine-3-carbonyl)-
amino]-nitrobenzene
Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and nicotinic acid chloride
(11) 4-[N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)-amino]-
nitrobenzene
Prepared from 4-(2-dimethylamino-ethylamino)-nitrobenzene and phenylacetyl-chloride
(12) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-3-bromo-
nitrobenzene
Prepared from 4-[N-(2-dimethylamino-ethyl)-amino]-3-bromo-nitrobenzene and acetyl chloride
(13) N-acryloyl-N-methyl-4-nitro-aniline

Prepared from 4-methylamino-nitrobenzene and acrylic acid chloride
(14) N-acryloyl-N-isopropyl-4-nitro-aniline
Prepared from 4-isopropylamino-nitrobenzene and acrylic acid chloride
(15) N-acryloyl-N-benzyl-4-nitro-aniline
Prepared from 4-ben.zylamino-nitrobenzene and acrylic acid chloride
(16) N-bromoacetyl-N-methyl-4-nitro-aniline
Prepared from 4-methylamino-nitrobenzene and bromoacetyl chloride
(17) N-bromoacetyl-N-isopropyl-4-nitro-aniline
Prepared from 4-isopropylamino-nitrobenzene and bromoacetyl chloride
(18) N-bromoacetyl-N-benzyl-4-nitro-aniline
Prepared from 4-benzylamino-riitrobenzene and bromoacetyl chloride
Example VII
N-(dimethylaminomethvlcarbonyl)-N-methyl-4-nitro-aniline 1.8 g of dimethylamine hydrochloride and 5.5 g of potassium carbonate are placed in 8 0 ml of acetone and 4.2 g of N-bromoacetyl-N-methyl-4-nitroaniline are added in three batches at room temperature. The mixture is stirred for 12 hours at room temperature. After this time the mixture is filtered and the filtrate is evaporated down. The residue is dissolved in ethyl acetate,, washed twice with water,, dried over sodium sulphate and finally concentrated by rotary evaporation. Yield: 2.8 g (79 % of theory), Rf value: 0.5 (silica gel, ethyl acetate/methanol = 7:3)
Melting point: 121-122°C
The following compounds are prepared analogously to Example VII:
(1) N-(piperidin-1-yl-methylcarbonyl)-N-methyl-4-nitroaniline
(2) N-(morpholin-4-yl-methylcarbonyl)-N-methyl-4-nitroaniline
(3) N-[(4-benzyl-piperazin-l-yl)-methylcarbonyl]-N-methyl-4-nitroaniline
(4) N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl-4-nitroaniline
(5) N-[(N-aminocarbonylmethyl-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline

(6) N-[(N-benzyl-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline
(7) N-[di-(2-methoxyethyl)-amino-methylcarbonyl]-N-methyl-4-nitroaniline
(8) N-(dimethylaminomethylcarbonyl)-N-isopropyl-4-nitro-aniline
(9) N-(piperidin-1-yl-methylcarbonyl)-N-isopropyl-4-nitro-aniline

(10) N-[(4-tert.butoxycarbonyl-piperazin-1-yl)-methylcarbonyl]-N-isopropyl-4-nitro-aniline
(11) N-[(N-benzyl-N-methyl-amino)-methylcarbonyl]-N-benzyl-4-nitro-aniline
(12) N-(dimethylaminomethylcarbonyl)-N-benzyl-4-nitro-aniline
(13) N-(piperidin-1-yl-methylcarbonyl)-N-benzyl-4-nitro-aniline
(13) N-[di-(2-hydroxyethyl)-amino-methylcarbonyl]-N-methyl-4-nitroaniline
(14) N-[(N-(2-methoxyethyl)-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline
(15) N-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)-methylcarbonyl]-N-methyl-4-nitroaniline
(16) N-[(4-methyl-piperazin-1-yl)-methylcarbonyl]-N-methyl-4-nitroaniline
(17) N- [ (imidazol-1-yl) -methylcarbonyl] -N-"methyl-4-nitroaniline
(18) N-[(phthalimido-2-yl)-methylcarbonyl]-N-methyl-4-nitroaniline
Example VIII
N-f(2-dimethylamino-ethyl)-carbonvl]-N-benzvl-4-nitro-aniline 0.5 g of dimethylamine hydrochloride, 1.1 ml of triethylamine and 1.2 g of N-acryloyl-N-benzyl-4-nitro-aniline are dissolved in 50 ml of methanol and stirred for 24 hours at room temperature. After this time the mixture is evaporated down. The residue is purified over an aluminium oxide column (activity 2-3) with methylene chloride/ethanol 50:1 as eluant. Yield: 1.4 g (98 % of theory),
Rf value: 0.8 (aluminium oxide, methylene chloride/ethanol = 20:1) Melting point: 73°C

The following compounds are prepared analogously to Example VIII:
(1) N-[(2-dimethylamino-ethyl)-carbonyl] -N-isopropyl-4-nitro-
aniline
Prepared from N-acryloyl-N-isopropyl-4-nitro-aniline and dimethylamine hydrochloride
(2) N- [ (2-dimethylathino-ethyl) -carbonyl] -N-methyl-4-nitro-
aniline
Prepared from N-acryloyl-N-methyl-4-nitro-aniline and dimethylamine hydrochloride
(3) N- [(2-(4-tert.butoxycarbonyl-piperazin-1-yl)-ethyl)-
carbonyl]-N-methyl-4-nitro-aniline
Prepared from N-acryloyl-N-methyl-4-nitro-aniline and N-tert.butoxycarbonyl-piperazine
(4) N-[(2-(piperidin-1-yl)-ethyl)-carbonyl] -N-methyl-4-nitro-
aniline
Prepared from N-acryloyl-N-methyl-4-nitro-aniline and piperidine
(5) N-[(2-(N-benzyl-N-methyl-amino)-ethyl)-carbonyl]-N-methyl-
4-nitro-aniline
Prepared from N-acryloyl-N-methyl-4-nitro-aniline and N-benzyl-N-methyl-amine
Example IX
4-(4-methyl-piperazine-l-yl)-nitrobenzene
31.5 g of 4-chloro-l-nitrobenzene and 44.4 ml of 1-methylpiperazine are combined and stirred for 18 hours at 90°C. Then the solution is poured onto ice water and the precipitate formed is suction filtered, washed with water and

recrystallised from ethanol/water 1:1. The residue is dried in
vacuo at 75°C.
Yield: 44.0 g (99 % of theory),
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
Melting point: 108-112°C
The following compounds are prepared analogously to Example IX:
(1) N-(2-dimethylaminoethyl)-N-methyl-4-nitroaniline Prepared from 1-fluoro-4-nitrobenzene and l-dimethylamino-2-methylamino-ethane
(2) N-(3-dimethylaminopropyl)-N-methyl-4-nitroaniline Prepared from 1-fluoro-4-nitrobenzene and l-dimethylamino-3-methylamino-propane

(3) 4-(N-carboxymethyl-amino)-nitrobenzene Prepared from 1-fluoro-4-nitrobenzene and glycine
(4) N-cyclohexyl-p-phenylenediamine
Prepared from 1-fluoro-4-nitrobenzene and cyclohexylamine
(5) 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-
phthalimido-2-yl-nitrobenzene
Prepared from 2-nitro-4-phthalimido-2-yl-fluorobenzene, N-(2-dimethylamino-ethyl)-methanesulphonamide and sodium hydride as base
(6) 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-1,3-
dinitrobenzene
Prepared from 2,4-dinitro-chlorobenzene, N-(2-dimethylamino-ethyl) -methanesulphonamide and sodium hydride as base

(7) 4-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-
chloro-nitrobenzene
Prepared from 2-fluoro-5-nitro-chlorobenzene, N-(2-dimethyl¬amino-ethyl) -methanesulphonamide and sodium hydride as base
(8) 4-(2-dimethylamino-ethyl-amino)-1, 3-dinitrobenzene Prepared from l-chloro-2,4-dinitro-benzene and N, N-dimethyl-ethylenediamine
(9) 4-[N-(2-dimethylamino-ethyl)-N-(ethylsulphonyl)-amino]-nitrobenzene
Prepared from 1-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -ethanesulphonamide and sodium hydride as base
(10) 4- [N- (2-dimethylamino-ethyl) -N- (propylsulphonyl) -amino] -
nitrobenzene
Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -propanesulphonamide and sodium hydride as base
(11) 4-[N-(2-dimethylamino-ethyl)-N-(butylsulphonyl)-amino]-
nitrobenzene
Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -butanesulphonamide and sodium hydride as base
(12) 4- [N- (2-dimethylamino-ethyl) -N- (benzylsulphonyl) -amino] -
nitrobenzene
Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -C-phenylmethanesulphonamide and sodium hydride as base
(13) 4- [N- (2-dimethylamino-ethyl) -N- (phenylsulphonyl) -amino] -
nitrobenzene
Prepared from l-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl) -benzenesulphonamide and sodium hydride as base
(14) 4-[N-(2-dimethylamino-ethyl)-N-(isopropylsulphonyl)-
amino]-nitrobenzene

Prepared from 1-fluoro-4-nitro-benzene, N-(2-dimethylamino-ethyl)-isopropylsulphonamide and sodium hydride as base
(15) 4- [N-(2-dimethylamino-ethyl)-amino]-3-bromo-nitrobenzene Prepared from 2-bromo-l-fluoro-4-nitro-benzene and N,N-dimethyl-ethylenediamine
(16) 4-isopropylamino-nitrobenzene
Prepared from 1-flu6ro-4-nitrobenzene and isopropylamine
(17) 4-benzylamino-nitrobenzene
Prepared from 1-fluoro-4-nitrobenzene and benzylamine
Example X
4-(imidazol-4-vl)-nitrobenzene
9.5 g of 2-phenylimidazole are carefully dissolved in 50 ml of
concentrated sulphuric acid and 5.8 g of ammonium nitrate are
added to this solution at 0°C. After a further 60 minutes
stirring at 0°C the mixture is poured onto ice water, made
basic with ammonia water and the precipitate formed is suction
filtered and recrystallised from ethanol.
Yield: 8.0 g (64 % of theory),
Rf value: 0.6 (silica gel, ethyl acetate/ethanol = 10:1)
C9H7N302
Mass spectrum: m/z = 189 [M+]
The following compounds are prepared analogously to Example X:
(1) 4 -(imidazol-2-yl)-nitrobenzene
Prepared from 4-(imidazol-2-yl)-benzene
(2) 4-(5-methyl-imidazol-4-yl)-nitrobenzene
Prepared from 4-methyl-5-phenyl-imidazole (J. Heterocycl. Chem. 1983, 20, 1277-1281)

Example XI
4-(2-(imidazol-4-yl)-ethylene)-nitrobenzene
1.5 g of 4-nitrobenzaldehyde and 7.45 g of (N-trityl-imidazol-4-yl-methyl)-triphenylphosphonium chloride are dissolved in 75 ml of tetrahydrofuran and to this solution 3.0 ml of DBU are added dropwise at room temperature. After a further 120 minutes stirring at room temperature the mixture is poured onto water and the precipitate formed is suction filtered. The product is taken up in 25 ml of IN hydrochloric acid and refluxed for 4 hours. After this time it is neutralised with ammoniacal water, extracted with ethyl acetate and the organic phase is washed with water, dried over sodium sulphate and evaporated down. The residue is purified over a silica gel column with methylene chloride/methanol 10:1 as eluant. Yield: 1.0 g of (47 % of theory),
Rf value: 0.6 (silica gel, ethyl acetate/ethanol = 10:1) Melting point: 185-188°C
Example XII
4-(piperidin-1-yl-methvl)-nitrobenzene
40.0 g of 4-nitrobenzyl bromide are dissolved in 500 ml of
methylene chloride, 51.5 ml of triethylamine are added and
18.3 ml of piperidine are carefully added dropwise. After the
end of the exothermic reaction the mixture is refluxed for
another 30 minutes. After cooling it is washed with water and
the organic phase is dried over sodium sulphate. Finally, the
organic phase is evaporated down.
Yield: 36.3 g of, (89 % of theory),
Rf value: 0.6 (silica gel, methylene chloride/methanol = 9:1)
C12H16N202
Mass spectrum: m/z = 221 [M+]

The following compounds are prepared analogously to Example XII:
(1) 4-[(2,6-dimethyl-piperidin-l-yl) -methyl]-nitrobenzene
(2) 3-(N,N-dimethyl-aminomethyl)-nitrobenzene
(3) 4-(N,N-dimethyl-aminomethyl)-nitrobenzene
l
(4) 4-(2-dimethylamino-ethyl)-nitrobenzene
(5) 4-(2-diethylamino-ethyl)-nitrobenzene
(6) 4-(diethylamino-methyl)-nitrobenzene
(7) 4-(N-benzyl-N-methyl-aminomethyl) -nitrobenzene
(8) 4-(N-ethyl-N-methyl-aminomethyl)-nitrobenzene
(9) 4-[N-(n-hexyl)-N-methyl-aminomethyl]-nitrobenzene

(10) 4-(thiomorpholin-4-yl-methyl)-nitrobenzene
(11) 4-[(4-methyl-piperazine-l-yl) -methyl]-nitrobenzene
(12) 4 -(imidazol-1-yl-methyl)-nitrobenzene
(13) 4- [2- (4-hydroxy-piperidin-l-yl) -ethyl-amino] -nitrobenzene
(14) 4- [ (3-hydroxy-pyrrolidin-l-yl) -methyl] -nitrobenzene
(15) 4-(1,2,4-triazol-1-yl-methyl)-nitrobenzene
(16) 4-(1,2,3-triazol-2-yl-methyl)-nitrobenzene
(17) 4-(1,2,3-triazol-l-yl-methyl)-nitrobenzene

(18) 4-[(N-ethoxycarbonylmethyl-N-methyl-amino)-methyl]-nitrobenzene
(19) 4-[(N-aminocarbonylmethyl-N-methyl-amino)-methyl]-nitrobenzene
(20) 4-(azetidin-1-yl-methyl)-nitrobenzene
(21) 4-[(di-(2-methoxy-ethyl)-amino)-methyl]-nitrobenzene
(22) 4-[N-(N-tert.butoxycarbonyl-3-amino-propyl)-N-methyl-aminomethyl]-nitrobenzene
(23) 4-[(N-propyl-N-methyl-amino)-methyl]-nitrobenzene
(24) 4-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)-methyl]-nitrobenzene
(25) 4-[(N-(3-dimethylamino-propyl)-N-methyl-amino)-methyl]-nitrobenzene
(26) 4-[(N-(2-methoxy-ethyl)-N-methyl-amino)-methyl]-nitrobenzene
(27) 4-[(N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl]-nitrobenzene
(28) 4-[(N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl]-nitrobenzene
(29) 4-(3-oxo-piperazine-l-yl-methyl)-nitrobenzene

Example XIII
4-[(N-carboxymethvl-N-methyl-amino)-methyll-nitrobenzene
7.33 g of 4-[(N-ethoxycarbonylmethyl-N-methyl-amino)-methyl] -
nitrobenzene are dissolved in 140 ml of ethanol, 34.0 ml of IN
sodium hydroxide solution are added and the mixture is stirred
for half an hour at room temperature. After this time the
mixture is neutralised with 34 ml of IN hydrochloric acid, the
solvent removed, the residue taken up in methylene chloride
and extracted with water. The aqueous phase is evaporated
down and the residue is recrystallised from methylene
chloride.
Yield: 5.43 g (84 % of theory),
Rf value: 0.4 (silica gel, methylene chloride/methanol = 2:1)
C10H12N2O4
Mass spectrum: m/z = 223 [M+]
Example XIV
4-(N-ethyl-aminomethyl)-nitrobenzene
6.0 g of 4-nitrobenzyl bromide are dissolved in 25 ml of
ethanol, combined with 25 ml of 10% ethanolic ethylamine
solution and refluxed for 2 hours. Then the solution is
concentrated by rotary evaporation, the residue is taken up
with methylene chloride and washed with dilute sodium
hydroxide solution. Finally the organic phase is evaporated
down.
Yield: 2.3 g (46 % of theory),
R£ value: 0.2 (silica gel, methylene chloride/methanol = 9:1)
C9H12N202
ESI mass spectrum: m/z = 179 [M-H~]
The following compounds are prepared analogously to Example XIV:
(1) 4-[N-(4-chlorobenzyl)-aminomethyl] -nitrobenzene

(2) 4-(N-cyclohexyl-aminomethyl)-nitrobenzene
(3) 4-(N-isopropyl-aminomethyl)-nitrobenzene
(4) 4-(N-propyl-aminomethyl)-nitrobenzene
(5) 4-(N-methyl-aminomethyl)-nitrobenzene
(6) 4-(N-butyl-aminomethyl)-nitrobenzene
(7) 4-(N-methoxycarbonylmethyl-aminomethyl)-nitrobenzene
(8) 4-(N-benzyl-aminomethyl)-nitrobenzene
(9) 4-(aminomethyl)-nitrobenzene

(10) 4-(pyrrolidin-1-yl-methyl)-nitrobenzene
(11) 4-(morpholin-4-yl-methyl)-nitrobenzene
(12) 4-(hexamethyleneiminomethyl)-nitrobenzene
(13) 4-(4-hydroxy-piperidin-1-yl-methyl)-nitrobenzene
(14) 4-(4-methoxy-piperidin-1-yl-methyl)-nitrobenzene
(15) 4-(4-methyl-piperidin-l-yl-methyl)-nitrobenzene
(16) 4-(4-ethyl-piperidin-l-yl-methyl)-nitrobenzene
(17) 4-(4-isopropyl-piperidin-l-yl-methyl)-nitrobenzene
(18) 4-(4-phenyl-piperidin-l-yl-methyl)-nitrobenzene
(19) 4-(4-benzyl-piperidin-l-yl-methyl)-nitrobenzene
(2 0) 4-(4-ethoxycarbonyl-piperidin-1-yl-methyl)-nitrobenzene
(21) 4-(N,N-dipropyl-aminomethyl)-nitrobenzene
(22) 4-(4-tert.butoxycarbonyl-piperazin-1-yl-methyl)-nitrobenzene
(23) 4- (2-morpholinJ-4-yl-ethyl) -nitrobenzene
(24) 4-(2-pyrrolidin-l-yl-ethyl)-nitrobenzene
(25) 4-(2-piperidin-l-yl-ethyl)-nitrobenzene
(26) 4-(N-ethyl-N-benzyl-aminomethyl)-nitrobenzene
(27) 4-(N-propyl-N-benzyl-aminomethyl)-nitrobenzene
(28) 4-[N-methyl-N-(4-chlorobenzyl)-aminomethyl]-nitrobenzene
(29) 4-[N-methyl-N-(4-bromobenzyl)-aminomethyl] -nitrobenzene
(30) 4-[N-methyl-N-(4-fluorobenzyl)-aminomethyl]-nitrobenzene
(31) 4-[N-methyl-N-(4-methylbenzyl)-aminomethyl]-nitrobenzene
(32) 4-[N-methyl-N-(3-chlorobenzyl)-aminomethyl]-nitrobenzene

(33) 4-[N-methyl-N-(3,4-dimethoxybenzyl)-aminomethyl]-nitrobenzene
(34) 4-[N-methyl-N-(4-methoxybenzyl)-aminomethyl]-nitrobenzene
(35) 4-(N-2,2,2-trifluoroethyl-N-benzyl-aminomethyl)-nitrobenzene
(36) 4-[N-2,2,2-trifluoroethyl-N-(4-chlorobenzyl)-aminomethyl]-nitrobenzene
(37) 4-(thiomorpholin-4-yl-methyl)-nitrobenzene
(38) 4-(azetidion-1-yl-methyl)-nitrobenzene
(39) 4-(3,4-dihydropyrrolidin-1-yl-methyl)-nitrobenzene
(40) 4-(3,4-dihydropiperidin-l-yl-methyl)-nitrobenzene
(41) 4- (2-methoxycarbonyl-pyrrolidin-l-yl-methyl) -nitrobenzene
(42) 4- (3,5-dimethyl-piperidin-l-yl-methyl) -nitrobenzene
(43) 4-(4-phenyl-piperazin-l-yl-methyl)-nitrobenzene
(44) 4-(4-phenyl-4-hydroxy-piperidin-1-yl-methyl)-nitrobenzene

(45) 4-[N-(3,4,5-trimethoxybenzyl-N-methyl-aminomethyl)-nitrobenzene
(46) 4-[N-(3,4-dimethoxybenzyl)-N-ethyl-aminomethyl]-nitrobenzene
(47) 4-[N-(2,6-dichlorobenzyl)-N-methyl)-aminomethyl]-nitrobenzene
(48) 4-[N-(4-trifluoromethylbenzyl)-N-methyl)-aminomethyl] -nitrobenzene
(49) 4-(N-benzyl-N-isopropyl-aminomethyl)-nitrobenzene
(50) 4-(N-benzyl-N-tert.butyl-aminomethyl)-nitrobenzene
(51) 4-(N,N-diisopropyl-aminomethyl)-nitrobenzene
(52) 4-(N,N-diisobutyl-aminomethyl)-nitrobenzene
(53) 4-(2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene
(54) 4-(2,3-dihydro-isoindol-2-yl-methyl)-nitrobenzene
(55) 4- (6, 7-dimetho*y-l, 2,3, 4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene
(56) 4-(l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene

(57) 4-[N-(2-hydroxyethyl)-N-benzyl-aminomethyl]-nitrobenzene
(58) 4-[N-(1-ethyl-pentyl)-N-(pyridin-2-yl-methyl)-aminomethyl]-nitrobenzene
(59) 4-(piperin-1-yl-methyl)-1,3-dinitrobenzene
(60) 4-(N-phenethyl-N-methyl-aminomethyl)-nitrobenzene
(61) 4-[N-(3,4-dihydroxy-phenethyl)-N-methyl-aminomethyl]-nitrobenzene

(62) 4-[N-(3, 4,5-trimethoxy-phenethyl)-N-methyl-aminomethyl]-nitrobenzene
(63) 4-[N-(3,4-dimethoxy-phenethyl)-N-methyl-aminomethyl]-nitrobenzene
(64) 4-[N-(3,4-dimethoxy-benzyl)-N-methyl-aminomethyl]-nitrobenzene
(65) 4-[N-(4-chloro-benzyl)-N-methyl-aminomethyl]-nitrobenzene(66) 4- [N-(4-bromo-benzyl)-N-methyl-aminomethyl]-nitrobenzene
(67) 4-[N-(4-fluoro-benzyl)-N-methyl-aminomethyl]-nitrobenzene
(68) 4- [N-(4-methyl-benzyl)-N-methyl-aminomethyl]-nitrobenzene
(69) 4-[N-(4-nitro-phenethyl)-N-methyl-aminomethyl]-nitrobenzene "
(70) 4-(N-phenethyl-N-benzyl-aminomethyl)-nitrobenzene
(71) 4-(N-phenethyl-N-cyclohexyl-aminomethyl)-nitrobenzene
(72) 4-[N-(2-(pyridin-2-yl)-ethyl)-N-methyl-aminomethyl]-nitrobenzene
(73) 4-[N-(2-(pyridin-4-yl)-ethyl)-N-methyl-aminomethyl]-nitrobenzene

(74) 4-[N-(pyridin-4-yl-methyl)-N-methyl-aminomethyl]-nitrobenzene
(75) 4-(N,N-dibenzyl-aminomethyl)-nitrobenzene
(76) 4-[N-(4-nitro-phenethyl)-N-propyl-aminomethyl]-nitrobenzene

(77) 4-(N-benzyl-N-(3-cyano-propyl)-aminomethyl)-nitrobenzene
(78) 4-(N-benzyl-N-allyl-aminomethyl)-nitrobenzene
(79) 4-[N-benzyl-N-(2,2,2-trifluoroethyl)-aminomethyl]-
nitrobenzene4-[N-(2-benzo(l,3)dioxol-5-yl-methyl)-N-methyl-aminomethyl]-nitrobenzene
(80) 4-(7-chloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene
(81) 4-(7,8-dichloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene
(82) 4-(7-methoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene
(83) 4- (7-rnethyl-2, 3,4, 5-tetrahydro-benzo(d) azepin-3-yl-methyl)-nitrobenzene
(84) 4-(7,8-dimethoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-nitrobenzene
(85) 4-(6,7-dichloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene
(86) 4-(6,7-dimethyl-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene
(87) 4-(6-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene
(88) 4-(7-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene
(89) 4-(6-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-nitrobenzene
(90) 4-(7-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl) -nitrobenzene

(92) 4-[(2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl)-methyl]-nitrobenzene
(93) 4-[(7-amino-2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl)-methyl]-nitrobenzene
(94) 4-[(2-amino-5,6,7,8-tetrahydro-azepino(4,5-d)thiazol-6-yl)-methyl]-nitrobenzene
(95) 4-[(5,6,7,8-tetrahydro-azepino(4,5-d)thiazol-6-yl)-methyl]-nitrobenzene
Example XV
4-(1,l-dioxo-thiomorpholin-4-yl-methyl)-nitrobenzene
6.0 g of 4-(thiomorpholin-4-yl-methyl)-nitrobenzene are
dissolved in 100 ml of methylene chloride and 10.3 g of meta-
chloroperbenzoic acid are slowly added. After a further 3
hours stirring at room temperature the precipitate obtained is
filtered off.
Yield: 6.2 g (91 % of theory)
Rf value: 0.5 (silica gel, methylene chloride/methanol = 1:1)
CnH14N204S
Mass spectrum: m/z = 270 [M+]
The following compound is prepared analogously to Example XV:
(1) 4-(1-oxo-thiomorpholin-4-yl-methyl)-nitrobenzene
Example XVI
4-fN-(3-amino-propyl)-N-methvlsulphonyl-amino]-nitrobenzene 9.5 g of 4-[N-(3-phthalimido-2-yl-propyl)-N-methylsulphonyl-amino] -nitrobenzene are dissolved in 200 ml of ethanol, 11.5 ml of hydrazine hydrate are added and the mixture is stirred for 1.5 hours at 50 °C. After cooling the residue is largely

evaporated down, water is added and the solution is extracted
with methylene chloride. The organic phase is dried,
evaporated down and purified over a silica gel column with
methylene chloride/methanol/ammonia 9:1:0.1.
Yield: 2.5 g (39 % of theory)
Rf value: 0.2 (silica gel, methylene chloride/methanol = 9:1)
C10H15N3O4S
ESI mass spectrum: m/z = 272 [M-H"]
The following compound is prepared analogously to Example XVI:
(1) 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-amino-nitrobenzene
Prepared from 6-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-phthalimido-2-yl-nitrobenzene
Example XVII
4-(l-methyl-imidazol-2-yl)-nitrobenzene
7.5 g of 4-(imidazol-2-yl)-nitrobenzene are dissolved in 50 ml
of dimethylsulphoxide and at 0°C 5.0 g of potassium
tert.butoxide are added. After one hour of stirring at room
temperature 2.6 ml of methyl iodide are added dropwise and the
mixture is stirred for one hour at room temperature. After
this time the residue is poured onto ice water and the
precipitate formed is suction filtered, washed with water and
dried.
Yield: 6.1 g (76 % of theory)
Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1)
Melting point: 186-187°C

The following compounds are prepared analogously to Example XVII:
(1) 4-(l-ethyl-imidazol-2-yl)-nitrobenzene
Prepared from 4-(imidazol-2-yl)-nitrobenzene and ethyl iodide
(2) 4-(l-benzyl-imidazol-2-yl)-nitrobenzene
Prepared from 4-(imidazol-2-yl)-nitrobenzene and benzyl
bromide Example XVIII
4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]-
nitrobenzene
5.0 g of 4-methylaminomethyl-nitrobenzene are dissolved in 30
ml of dimethylformamide and 4.6 g of 2-(2-methoxy-ethoxy)-
ethyl chloride are added. After six hours" stirring at 100°C
the solvent is removed and the residue is taken up in ethyl
acetate. The organic phase is washed with water and dried
over sodium sulphate. After the elimination of the solvent the
residue is purified over an aluminium oxide column (activity
2-3) with toluene/ethyl acetate 5:1 as eluant.
Yield: 2.3 g (29 % of theory)
Rf value: 0.5 (aluminium oxide, toluene/ethyl acetate = 5:1)
C13H20N2O4
ESI mass spectrum: m/z = 267 [M-H~]
Example XIX
4-(N-ethyl-N-tert.butoxvcarbonyl-aminomethyl)-nitrobenzene 2.2 g of 4-(ethylaminomethyl)-nitrobenzene are dissolved in 50 ml of ethyl acetate and stirred with 2.6 g of di-tert-butyl. dicarbonate (tert.butoxycarbonyl-anhydride) for 30 minutes at room temperature. Then the solution is washed with water and evaporated down. Yield: 3.4 g of theory

Rf value: 0.3 (silica gel, methylene chloride/methanol =
50:1)
Melting point: 85 °C
The following compounds are prepared analogously to Example XIX:
(1) 4-[N-(4-chlorophenyl-methyl)-N-tert.butoxycarbonyl-aminomethyl] -nitrobenzene
(2) 4-(N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene
(3) 4-(N-cyclohexyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene
(4) 4-(N-isopropyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene

(5) 4-(N-methyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene
(6) 4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene
(7) 4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene
(8) 4-(N-methoxycarbonylmethyl-N-tert.butoxycarbonyl-aminomethyl) -nitrobenzene
(9) 4-(N-benzyl-N-tert.butoxycarbonyl-aminomethyl)-nitrobenzene

(10) 4- [N- (3-trifluoroacetylamino-propyl) -N-methylsulphonyl-
amino]-nitrobenzene
Prepared from 4- [N- (3-amino-propyl) -N-methylsulphonyl-amino] -nitrobenzene and trifluoroacetic acid anhydride
(11) 4-[(4-tert.butoxycarbonyl-piperazin-1-yl)-methyl] -
nitrobenzene
Example XX
4-(piperidin-1-yl-methvl)-aniline
37.0 g of 4-(piperidin-1-yl-methyl)-nitrobenzene are dissolved
in 3 00 ml of methanol, 8.0 g of Raney nickel are added and the
mixture is hydrogenated for 85 minutes with 3 bars of hydrogen
at room temperature. The catalyst is filtered off and the
filtrate is evaporated down.
Yield: 24.0 g (75 % of theory),
R£ value: 0.4 (silica gel, methylene chloride/methanol = 9:1)
C12H18N2
ESI mass spectrum: m/z = 191 [M+H+]
The following compounds are prepared analogously to Example VIII:
(1) 4-[(2,6-dimethyl-piperidin-l-yl)-methyl]-aniline
(2) N-(2-dimethylamino-ethyl)-N-methylsulphonyl-p-phenylenediamine
(3) 3-(dimethylaminomethyl)-aniline
(4) 4-(dimethylaminomethyl)-aniline
(5) 4-(2-dimethylamino-ethyl)-aniline
(6) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-aniline

(7) 4-[N-(3-dimethylamino-propyl)-N-acetyl-amino]-aniline
(8) 4-[N-(2-dimethylamino-ethyl)-N-benzoyl-amino]-aniline
(9) 4-[N-(2-dimethylamino-ethyl)-N-propionyl-amino]-aniline

(10) 4-[N-(2-dimethylamino-ethyl)-N-butyryl-amino]-aniline
(11) 4-[N-(2-dimethylamino-ethyl)-N-isobutyryl-amino]-aniline
(12) 4-(N-tert.butoxycarbonyl-aminomethyl)-aniline
(13) 4-(N-ethyl-N-tert.butoxycarbonyl-aminomethyl)-aniline

(14) 4-[N-(4-chlorophenyl-methyl)-N-tert.butoxycarbonyl-aminomethyl] -aniline
(15) 4-(N-cyclohexyl-N-tert.butoxycarbonyl-aminomethyl)-aniline
(16) 4-(N-isopropyl-N-tert.butoxycarbonyl-aminomethyl)-aniline
(17) 4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)-aniline
(18) 4-(N-methyl-N-tert.butoxycarbonyl-aminomethyl)-aniline
(19) 4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)-aniline
(2 0) 4-(N-methoxycarbonyl-methyl-N-tert.butoxycarbonyl-aminomethyl) -aniline
(21) 4-(N-benzyl-N-tert.butoxycarbonyl-aminomethyl)-aniline
(22) 4-(pyrrolidin-1-yl-methyl)-aniline

(23) 4-(morpholin-4-yl-methyl)-aniline
(24) 4- (hexamethyleneirninomethyl) -aniline
(25) 4-(4-hydroxy-piperidin-l-yl-methyl)-aniline
(26) 4-(4-methoxy-piperidin-1-yl-methyl)-aniline
(27) 4-(4-methyl-piperidin-l-yl-methyl)-aniline
(28) 4-(4-ethyl-piperidin-l-yl-methyl)-aniline
(29) 4-(4-isopropyl-piperidin-l-yl-methyl)-aniline
(30) 4-(4-phenyl-piperidin-l-yl-methyl)-aniline
(31) 4-(4-benzyl-piperidin-l-yl-methyl)-aniline
(32) 4-(4-ethoxycarbonyl-piperidin-l-yl-methyl)-aniline
(33) 4-(N,N-dipropyl-aminomethyl)-aniline
(34) 4-(4-tert.butoxycarbonyl-piperazin-1-yl-methyl)-aniline
(35) 4-(2-morpholin-4-yl-ethyl)-aniline
(36) 4-(2-pyrrolidin-l-yl-ethyl)-aniline
(37) 4-(2-piperidin-l-yl-ethyl)-aniline
(38) 4-(N-propyl-N-benzyl-aminomethyl)-aniline
(39) 4-[N-(n-hexyl)-N-methyl-aminomethyl]-aniline
(40) 4-[N-methyl-N-(4-chlorobenzyl)-aminomethyl]-aniline

41) 4-[N-methyl-N-(4-bromobenzyl)-aminomethylJ-aniline
(42) 4-[N-methyl-N-(4-methylbenzyl)-aminomethyl]-aniline
(43) 4-[N-methyl-N-(4-fluorobenzyl)-aminomethyl]-aniline
(44) 4-[N-methyl-N-(3-chlorobenzyl)-aminomethyl]-aniline
(45) 4-[N-methyl-N-(3,4-dimethoxybenzyl)-aminomethyl]-aniline
(46) 4-[N-methyl-N-(4-methoxybenzyl)-aminomethyl]-aniline
(47) 4-(N-2,2,2-trifluoroethyl-N-benzyl-aminomethyl)-aniline
(48) 4-[N-2,2,2-trifluoroethyl-N-(4-chlorobenzyl)-aminomethyl]-aniline
(49) 4-(thiomorpholin-4-yl-methyl)-aniline
(50) 4-(l-oxo-thiomorpholin-4-yl-methyl)-aniline
(51) 4-(1,l-dioxo-thiomorpholin-4-yl-methyl)-aniline
(52) 4-(azetidion-1-yl-methyl)-aniline
(53) 4-(3,4-dihydropyrrolidin-l-yl-methyl)-aniline
(54) 4-(3,4-dihydropiperidin-l-yl-methyl)-aniline
(55) 4-(2-methoxycarbonyl-pyrrolidin-l-yi-methyl)-aniline
(56) 4-(3,5 -dimethyl-piperidin-1-yl-methyl)-aniline
(57) 4-(4-phenyl-piperazin-l-yl-methyl)-aniline
(58) 4-(4-phenyl-4-hydroxy-piperidin-1-yl-methyl)-aniline

(59) 4-[N-(3,4,5-trimethoxy-benzyl)-N-methyl-aminomethyl]-aniline
(60) 4-[N-(3,4-dimethoxy-benzyl)-N-ethyl-aminomethyl]-aniline
(61) 4-(N-benzyl-N-ethyl-aminomethyl)-aniline
(62) 4-[N-(2,6-dichlorobenzyl)-N-methyl-aminomethyl]-aniline
(63) 4-[N-(4-trifluoromethylbenzyl)-N-methyl-aminomethyl]-aniline
(64) 4-(N-benzyl-N-isopropyl-aminomethyl)-aniline
(65) 4-(N-benzyl-N-tert.butyl-aminomethyl)-aniline
(66) 4-(diethylamino-methyl)-aniline
(67) 4-(2-diethylamino-ethyl)-aniline
(68) 4-(N,N-diisopropyl-aminomethyl)-aniline
(69) 4-(N,N-diisobutyl-aminomethyl)-aniline
(70) 4-(2,3,4,5-tetrahydro~benzo(d)azepin-3-yl-methyl)-aniline
(71) 4-(2,3-dihydro-isoindol-2-yl-methyl)-aniline

(72) 4-(6,7-dimethoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline
(73) 4-(l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline
(74) 4-[N-(2-hydroxy-ethyl)-N-benzyl-aminomethyl]-aniline

75) 4- [N-(1-ethyl-pentyl)-N-(pyridin-2-yl-methyl)-
aminomethyl]-aniline
(76) 4-(piperidin-1-yl-methyl)-3-nitro-aniline
(77) 4-(piperidin-1-yl-methyl)-3-amino-aniline
(78) 4-(N-benzyl-N-methyl-aminomethyl)-aniline
(79) 4-(N-ethyl-N-methyl-aminomethyl)-aniline
(80) 4-(N-phenethyl-N-methyl-aminomethyl)-aniline

(81) 4-[N-(3,4-dihydroxy-phenethyl)-N-methyl-aminomethyl]-aniline
(82) 4-[N-(3,4,5-trimethoxy-phenethyl)-N-methyl-aminomethyl] -aniline
(83) 4- [N-(3,4-dimethoxy-phenethyl)-N-methyl-aminomethyl]-aniline
(84) 4- [N-(3,4-dimethoxy-benzyl)-N-methyl-aminomethyl]-aniline
(85) 4- [N- (4-chloro-benzyl)-N-methyl-aminomethyl]-aniline
(86) 4-[N-(4-bromo-benzyl)-N-methyl-aminomethyl]-aniline
(87) 4- [N- (4-fluoro-benzyl)-N-methyl-aminomethyl]-aniline
(88) 4-[N-(4-methyl-benzyl)-N-methyl-aminomethyl]-aniline
(89) 4- [N-(4-nitro-phenethyl)-N-methyl-aminomethyl]-aniline
(90) 4-(N-phenethyl-N-benzyl-aminomethyl)-aniline

(91) 4-(N-phenethyl-N-cyclohexyl-aminomethyl)-aniline
(92) 4-[N-(2-(pyridin-2-yl)-ethyl)-N-methyl-aminomethyl]-aniline
(93) 4-[N-(2-(pyridin-4-yl)-ethyl)-N-methyl-aminomethyl]-aniline
(94) 4-[N-(pyridin-4-yl-methyl)-N-methyl-aminomethyl]-aniline
(95) 4-(N,N-dibenzylaminomethyl)-aniline
(96) 4-[N-(4-nitro-benzyl)-N-propyl-aminomethyl]-aniline
(97) 4-[N-benzyl-N-(3-cyano-propyl)-aminomethyl]-aniline
(98) 4-(N-benzyl-N-allyl-aminomethyl)-aniline
(99) 4-[N-benzyl-N-(2,2,2-trifluoroethyl)-aminomethyl]-aniline

(100) 4-[(benzo(1,3)dioxol-5-yl-methyl)-methyl-aminomethyl]-aniline
(101) 4-(7-chloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline

(102) 4-(7,8-dichloro-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline
(103) 4-(7-methoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline
(104) 4-(7-methyl-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline

(105) 4-(7,8-dimethoxy-2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-aniline
(10 6) 4-(6,7-dichloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline
(107) 4-(6,7-dimethyl-1,2,3,4-tetrahydro-isoquinolin-2-yl-
methyl)-aniline
(108) 4-(6-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl) -
aniline
(109) 4-(7-chloro-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl) -aniline
(110) 4-(6-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline
(111) 4-(7-methoxy-l,2,3,4-tetrahydro-isoquinolin-2-yl-methyl)-aniline
(112) 4-(2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl-methyl)-aniline
(113) 4-(7-amino-2,3,4,5-tetrahydro-azepino(4,5-b)pyrazin-3-yl-methyl)-aniline
(114) 4-(2-amino-5,6,7,8-tetrahydro-azepino(4, 5-d)thiazol-6-yl-methyl)-aniline
(115) 4-(5,6,7,8-tetrahydro-azepino(4, 5-d) thiazol-6-yl-methyl) -aniline

(116) 4-(4-methyl-piperazin-l-yl)-aniline
(117) 4-[N-(2-dimethylamino-ethyl)-N-methyl-amino]-aniline

(118) 4-[N-(3-dimethylamino-propyl)-N-methyl-amino]-aniline
(119) N-(3-dimethylamino-propyl)-N-methylsulphonyl-p-phenylenediamine
(12 0) 4-[(N-dimethylaminocarbonylmethyl-N-methylsulphonyl)-amino]-aniline
(121) N-(4-aminophenyl)-N-methyl-methanesulphonamide
(122) 4-(imidazol-4-yl)-aniline
(123) 4-(tetrazol-5-yl)-aniline
(124) 4-[N-(2-dimethylamino-ethyl)-N-propionyl-amino]-aniline

(125) N-(dimethylaminomethylcarbonyl)-N-methyl-p-phenylenediamine
(126) N-[(2-dimethylamino-ethyl)-carbonyl]-N-methyl-p-phenylenediamine

(127) 4-(N-acetyl-N-dimethylaminocarbonylmethyl)-amino)-aniline
(128) N-methylaminocarbonylmethyl-N-methylsulphonyl-p -phenylenediamine
(12 9) N-aminocarbonylmethyl-N-methylsulphonyl-p-phenylenediamine
(130) 4-(imidazolidin-2,4-dion-5-ylidene-methyl)-aniline
(131) 4-(imidazolidin-2,4-dion-5-yl-methyl)-aniline

(132) 4-(2-oxo-pyrrolidin-l-yl-methyl)-aniline
(133) N-cyanomethyl-N-methylsulphonyl-p-phenylenediamine
(134) 4-[2-(imidazol-4-yl)-ethyl] -aniline
(135) 4-[(4-methyl-piperazin-l-yl)-methyl]-aniline
(136) 4- [N- (2- (N-bejizyl-N-methyl-amino) -ethyl) -N-methylsulphonyl-amino]-aniline
(137) 4-[N-(3-(N-benzyl-N-methyl-amino)-propyl)-N-methylsulphonyl-amino]-aniline
(13 8) N-cyclohexyl-p-phenylenediamine
(13 9) 4-(pyridin-4-yl-methyl)-aniline
(140) 4-(imidazol-1-yl-methyl)-aniline
(141) 4-benzyl-aniline
(142) N-(3-trifluoroacetylamino-propyl)-N-methylsulphonyl-p-phenylenediamine
(143) tert.butyl 4-amino-phenylacetate
(144) 4-(imidazol-2-yl)-aniline
(145) 4-(l-methyl-imidazol-2-yl)-aniline
(14G) 4-(l-ethyl-imidazol-2-yl)-aniline
(147) 4-(l-benzyl-imidazol-2-yl)-aniline
(148) 4-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-amino-ani1ine
(149) 4-[N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino]-3-chloro-aniline
(150) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-3-amino-aniline
(151) 4-[N-(2-dimethylamino-ethyl)-N-acetyl-amino]-3-bromo-aniline
(152) 4-[2-(4-hydroxy-piperidin-l-yl)-ethyl-amino]-aniline
(153) N-(2-dimethylamino-ethyl)-N-ethylsulphonyl-p-phenylenediamine

(154) N-(2-dimethylamino-ethyl)-N-propylsulphonyl-p-phenylenediamine
(155) N-(2-dimethylamino-ethyl)-N-isopropylsulphonyl-p-phenylenediamine
(156) N-(2-dimethylamino-ethyl)-N-butylsulphonyl-p-phenylenediamine
(157) N-(2-dimethylamino-ethyl)-N-benzylsulphonyl-p-phenylenediamine
(158) N-(2-dimethylamino-ethyl)-N-phenylsulphonyl-p-phenylenediamine
(159) 4-((3-hydroxy-pyrrolidin-l-yl)-methyl)-aniline
(160) 4-[N-(2-dimethylamino-ethyl)-N-(furan-2-carbonyl)-
amino]-aniline
(161) 4-[N-(2-dimethylamino-ethyl)-N-(2-methoxy-benzoyl)-amino]-aniline
(162) 4-[N-(2-dimethylamino-ethyl)-N-(pyridine-3-carbonyl)-amino]-aniline
(163) 4-[N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)-amino]-aniline .,"
(164) N-(piperidin-1-yl-methylcarbonyl)-N-methyl-p-phenylenediamine
(165) N-(morpholin-4-yl-methylcarbonyl)-N-methyl-p-phenylenediamine
(166) N- [ (4-benzyl-piperazin-l-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine
(167) N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl-p-phenylenediamine
(168) 4-(5-methyl-imidazol-4-yl)-aniline
(169) N-[(2-dimethylamino-ethyl)-carbonyl]-N-isopropyl-p-phenylenediamine
(170) N-[(2-dimethylamino-ethyl)-carbonyl]-N-benzyl-p-phenylenediamine
(171) N-(N-aminocarbonylmethyl-N-methyl-amino)-methylcarbonyl)-N-methyl-p-phenylenediamine
(172) N-[(N-benzyl-N-methyl-amino)-methylcarbonyl]-N-methyl-p-phenylenediamine

(173) N-[di-(2-methoxyethyl)-amino-methylcarbonyl]-N-methyl-p-phenylenediamine
(174) N- f (2- (4-tert.butoxycarbonyl-piperazin-1-yl)-ethyl)-carbonyl]-N-methyl-p-phenylenediamine
(175) N-[(2-(piperidin-1-yl)-ethyl)-carbonyl]-N-methyl-p-phenylenediamine
(176) N-[(2-(N-benzyl-N-methyl-amino)-ethyl)-carbonyl]-N-methyl-p-phenylenediamine
(177) N-(dimethylaminomethylcarbonyl)-N-isopropyl-p-phenylenediamine
(178) N-(piperidin-1-yl-methylcarbonyl)-N-isopropyl-p-phenylenediamine
(179) N-[(4-tert.butoxycarbonyl-piperazin-1-yl)-methylcarbonyl]-N-isopropyl-p-phenylenediamine
(180) N- [ (N-benzyl-N-methyl-amino) -methylcarbonyl]-N-benzyl-p-phenylenediamine
(181) N-(dimethylaminomethylcarbonyl)-N-benzyl-p-phenylenediamine
(182) N-(piperidin-1-yl-methylcarbonyl)-N-benzyl-p-phenylenediamine
(183) 4-(1,2,4-triazol-l-yl-methyl)-aniline
(184) 4-(1,2,3-triazol-2-yl-methyl)-aniline
(185) 4-(1,2,3-triazol-l-yl-methyl)-aniline

(186) 4-[(N-ethoxycarbonylmethyl-N-methyl-amino)-methyl]-aniline
(187) 4-[(N-aminocarbonylmethyl-N-methyl-amino)-methyl]-aniline
(188) 4-(azetidin-1-yl-methyl)-aniline
(189) 4-[(di-(2-methoxy-ethyl)-amino)-methyl]-aniline
(190) 4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]-aniline
(191) 4-[N-(N-tert.butoxycarbonyl-3-amino-propyl)-N-methyl-
aminomethyl]-aniline
(192) 4-[(N-(methylcarbamoyl-methyl)-N-methyl-amino)-methyl]-aniline
(193) 4-[(N-(dimethylcarbamoyl-methyl)-N-methyl-amino)-methyl]-aniline
(194) 4-[(N-propyl-N-methyl-amino)-methyl] -aniline
(195) 4-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)-methyl]-
aniline
(196) 4- [ (N-(3-dimethylamino-propyl)-N-methyl-amino)-methyl]-aniline
(197) 4-[(N-(2-methoxy-ethyl)-N-methyl-amino)-methyl]-aniline
(198) 4-[(N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl]-aniline
(199) 4-[(N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl]-aniline

(200) 4-(3-oxo-piperazin-l-yl-methyl)-aniline
(201) N-[di-(2-hydroxyetttyl)-amino-methylcarbonyl]-N-methyl-p-
phenylenediamine
(202) N- [ (N- (2-methoxyethyl) -N-methyl-aiuino) -m.ethylcarban.Yll -
N-methyl-p-phenylenediamine
l
(203) N-[(N-(2-dimethylamino-ethyl)-N-methyl-amino)-
methylcarbonyl]-N-methyl-p-phenylenediamine
(204) N-[(4-methyl-piperazin-l-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine
(205) N-[(imidazol-1-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine
(206) N-[(phthalimido-2-yl)-methylcarbonyl]-N-methyl-p-phenylenediamine
Example XXI
4-(4-hvdroxvmethyl-piperidin-l-yl-methvl-amino)-aniline 1.1 g of 4-(4-ethoxycarbonyl-piperidin-l-yl-methyl-amino)-aniline are suspended in 15 ml of tetrahydrofuran. 175 mg of lithium borohydride are added at room temperature, stirred for 24 h, another 175 mg of lithium borohydride are added and after a further 7.5 hours 15 ml of water are added and the mixture is stirred for 10 minutes. It is extracted three times with 15 ml of ethyl acetate. The combined organic phases are washed with water and saturated saline solution, dried over sodium sulphate and concentrated by rotary evaporation. The residue is purified over a silica gel column with methylene chloride/methanol/ammonia 4:1:0.01 as eluant. Yield: 20 0 mg (2 7 % of theory)

Rf value: 0.4 (silica gel, methylene chloride/methanol/ammonia 4:1:0.01)
Melting point: 157°C Example XXII
methyl 4-methoxycarbonylmethyl-3-nitro-benzoate 54.3 g of methyl 3-nitro-benzoate and 29.0 g of methyl chloroacetate are dissolved in 10 0 ml of dimethylformamide and this solution is added dropwise at -10°C to a solution of 78.5 g of potassium-tert. butoxide in 500 ml of dimethylformamide. The mixture is stirred for another 10 minutes at room temperature and after this time the solution is poured onto 350 ml of concentrated hydrochloric acid in 2 1 of ice water. The solution is stirred for 0.5 hours, the precipitate obtained is suction filtered and washed with water. The product is recrystallised from 150 ml of methanol and dried at 4 0°C in vacuo.
Yield: 48.3 g of (51 % of theory), contains about 20 % of
methyl 6-methoxycarbonylmethyl-3-nitro-benzoate
Rf value: 0.7 (silica gel, petroleum ether/ethyl acetate =
1:1)
Melting point: 65-73 °C
The following compound is prepared analogously to Example XXII:
(1) ethyl 4-methoxycarbonylmethyl-3-nitro-benzoate Prepared from ethyl 4-thoxycarbonylmethyl-3-nitro-benzoate
Example XXIII
methyl 2-indolinone-6-carboxylate
4 8.3 g of methyl 4-methoxycarbonylmethyl-3-nitro-benzoate are
dissolved in 800 ml of concentrated acetic acid, 5.0 g of

palladium on carbon (10%) are added and the solution is hydrogenated for 2.5 hours at room temperature and 5 0 psi. The catalyst is filtered off and the filtrate is evaporated down. The residue is taken up in 150 ml of tert.-butylmethyl ether, filtered again and dried in vacuo at 100°C.
Yield: 28.6 g (98 % of theory),
R£ value: 0.4 (silica gel, methylene chloride/methanol = 10:1)
Melting point: 208-211 °C
The following compound is prepared analogously to Example XXIII:
(1) ethyl 2-indolinone-6-carboxylate Prepared from ethyl 4-methoxycarbonylmethyl-3-nitro-benzoate
Example XXIV
1-acetyl-3-(l-ethoxy-1-phenylmethylene)-6-ethoxycarbonyl-
2-indolinone
15.0 g of ethyl 2-indolinone-6-carboxylate, 49.6 ml of triethyl orthobenzoate and 150 ml of acetic anhydride are stirred for 4 hours at 110°C. After this time the solvent is removed, the residue is recrystallised from petroleum ether and dried in vacuo at 50°C.
Yield: 16.9 g (61 % of theory),
Rf value: 0.5 (silica gel, petroleum ether/methylene
chloride/ethyl acetate =5:4:1)
Melting point: 98-100°C
C22H21N05
The following compounds are prepared analogously to Example XXIV:
(1) 1-acetyl-3-(l-ethoxy-1-phenylmethylene)-6-methoxycarbonyl-2-indolinone

Preparation of the final compounds:
Example 1
3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene!- 6-carbamoyl-2-indolinone-trifluoroacetate
300 mg of resin obtained according to Example II are suspended
in 3 ml of dimethylformamide and shaken with 0.2 g of 4-
(piperidin-1-yl-methyl)-aniline for 22 hours at 70°C. Then it
is filtered off and the resin is washed several times with
methylene chloride, methanol and dimethylformamide. Then 1 ml
of methanolic ammonia is added for 2 hours in order to
eliminate the acetyl group. Then after further washing 4 ml of
10% trifluoroacetic acid in methylene chloride are added
during another 60 minutes, the resin is separated off and the
solution is evaporated down.
Yield: 69 mg
Rf value: 0.1 (silica gel, methylene chloride/methanol = 9:1)
C2eH28N402
Mass spectrum: m/z = 452 (m+)
The following compounds are prepared analogously to Example 1:
(1) 3-Z-(1-Anilino-l-phenyl-methylene)-6-carbamoyl-2-
indolinone
Prepared from the resin obtained according to Example II and
aniline
C22H17N302
Mass spectrum: m/z = 355 (m+)
(2) 3-Z-[1-(4-dimethylaminomethyl-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-dimethylaminomethyl-aniline
C25H24N402
Mass spectrum: m/z = 412 (m+)

(3) 3-Z-[1-(4-(2-diethylamino-ethyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-(2-diethylamino-ethyl)-aniline
C28H30N4O2
Mass spectrum: m/z = 454 (m+)
(4) 3-Z-[1-(4-(morpholin-4-yl-methyl)-anilino)-1-phenyl-
methylene]-6 -carbamoyl-2 -indolinone-1ri fluoroacetate
Prepared from the resin obtained according to Example II and
4-(morpholin-4-yl-methyl)-aniline
Rf value: 0.50 (silica gel, methylene chloride/methanol = 4:1)
C27H26N403
Mass spectrum: m/z = 454 (m+)
(5) 3-Z- [1-(4-(l-oxo-thiomorpholin-4-yl-methyl)-anilino)-
1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-(l-oxo-thiomorpholin-4-yl-methyl)-aniline
Rf value: 0.3 0 (silica gel, methylene chloride/methanol = 9:1)
C27H26N403S
Mass spectrum: m/z = 486 (m+)
(6) 3-Z-[l-(4-(l,l-dioxo-thiomorpholin-4-yl-methyl)-anilino)-
1-phenyl-methylene]-6 -carbamoyl-2 -indolinone-tri fluoroacetate
Prepared from the resin obtained according to Example II and
4-(1,l-dioxo-thiomorpholin-4-yl-methyl)-aniline
Rf value: 0.30 (silica gel, methylene chloride/methanol = 9:1)
C27H26N404S
Mass spectrum: m/z = 502 (m+)
(7) 3-Z-[1-(4-(benzylaminomethyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate

Prepared from the resin obtained according to Example II and
4-[N-(phenyl-methyl)-N-tert.butoxycarbonyl-aminomethyl]-
aniline
Rf value: 0.40 (silica gel, methylene chloride/methanol =4:1)
C30H26N4O2
Mass spectrum: m/z = 474 (m+)
(8) 3-Z- [1-(4-(amino-methyl)-anilino)-1-phenyl-methylene]-
6-carbamoyl-2-indolinone-trifluoroacetate
Prepared f rom the resin obtained according to Example II and
4-(N-tert.butoxycarbonyl-aminomethyl)-aniline
Rf value: 0.10 (silica gel, methylene chloride/methanol =4:1)
C23H20N4O2
Mass spectrum: m/z = 384 (m+)
(9) 3-Z- [1-(4-(2,6-dimethylpiperidin-l-yl-methyl)-anilino)-
1-phenyl-methylene]- 6-ca^bamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-(2,6-dimethylpiperidin-i-yl-methyl)-aniline
Rf value: 0.45 (silica gel, methylene chloride/methanol =4:1)
C30H32N4O2
Mass spectrum: m/z = 480 (m+)
(10) 3-Z-[1-(4-(pyrrolidin-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2 -indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-(pyrrolidin-l-yl-methyl)-aniline
Rf value: 0.15 (silica gel, methylene chloride/methanol =4:1)
^"27-"-26-"-"4^2
Mass spectrum: m/z = 438 (m+)
(11) 3-Z- [1-(3-(dimethylaminomethyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
3-dimethylaminomethyl-aniline
Rf value: 0.23 (silica gel, methylene chloride/methanol =4:1)

C25H24N403
Mass spectrum: m/z = 412 (m+)
(12) 3-Z-[1-(3-(N-methyl-N-ethyl-aminomethyl)-anilino)-
1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
3- (N-methyl-N-ethyl-aminomethyl)-aniline
Rf value: 0.23 (silica gel, methylene chloride/methanol = 4:1)
C26H26N402
Mass spectrum: m/z .= 426 (m+)
(13) 3-Z-[1-(3-(methylaminomethyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-(N-tert.butoxycarbonyl-N-methyl-aminomethyl)-aniline
Rf value: 0.06 (silica gel, methylene chloride/methanol =4:1)
C24H22N402
Mass spectrum: m/z = 399 (m+H+)
(14)- 3-Z- [1- (3-hydroxymethyl-anilino) -1-phenyl-methylene] -
6 -carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example II and
3-amino-benzyl alcohol
Rf value: 0.7 (silica gel, methylene chloride/methanol =4:1)
C23H19N303
Mass spectrum: m/z = 385 (m+)
(15) 3-Z- [1- (4- (methoxycarbonylmethyl-aminomethyl) -anilino) -
1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4- (N-methoxycarbonylmethyl-N-tert.butoxycarbonyl-aminomethyl) -
aniline
Rf value: 0.4 0 (silica gel, methylene chloride/methanol = 9:1)
C26H24N404
Mass spectrum: m/z = 457 (m+H+)

(16) 3-Z-[1-(4-(N-methylsulphonyl-N-(dimethylaminocarbonyl-
methyl)-amino)-anilino)-1-phenyl-methylene]-6-carbamoyl-
2-indolinone
Prepared from the resin obtained according to Example II and
4-(N-methylsulphonyl-N-(dimethylaminocarbonylmethyl)-amino) -
aniline
Rf value: 0.40 (silica gel/ methylene chloride/methanol = 9:1)
C27H27N505S
Mass spectrum: m/z - 533 (m+)
(17) 3-Z-[1-(4-(N-acetyl-aminomethyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone
Prepared from the resin obtained according to Example II and
4-(N-acetyl-aminomethyl)-aniline
R£ value: 0.70 (silica gel, methylene chloride/methanol = 4:1)
C2SH22N403
Mass spectrum: m/z = 426 (m+)
(18) 3-Z-[1-(3,4-dimethoxy-anilino)-1-phenyl-methylene]-
6 -carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example II and
3,4-dimethoxy-aniline
Rf value: 0.40 (silica gel, methylene chloride/methanol = 9:1)
C24H21N304
Mass spectrum: m/z = 415 (m+)
(19) 3-Z-[1-(4-(morpholin-4-yl)-anilino)-1-phenyl-methylene]-
6 -carbamoyl-2 -indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-morpholin-4-yl-aniline
Rf value: 0.2 0 (silica gel, methylene chloride/methanol = 9:1)
C26H24N403
Mass spectrum: m/z = 440 (m+)
(20) 3-Z-[1-(4-acetylamino-anilino)-1-phenyl-methylene]-
6-carbamoyl-2 -indolinone

Prepared from the resin obtained according to Example II and
4 -acetylamino-aniline
Rf value: 0.25 (silica gel, methylene chloride/methanol = 9:1)
C24H20N4O3
Mass spectrum: m/z = 412 (m+)
(21) 3-Z- [1-(4-amino-anilino)-1-phenyl-methylene]-6-carbamoyl-
2-indolinone
Prepared from the resin obtained according to Example II and
4-amino-aniline
Rf value: 0.40 (silica gel, methylene chloride/methanol = 9:1)
C22H18N402
Mass spectrum: m/z = 370 (m+)
(22) 3-Z-[1-(4-N-methyl-N-acetyl-amino-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone
Prepared from the resin obtained according to Example II and 4-(N-methyl-N-acetyl-amino)-aniline
Mass spectrum: m/z = 426 (m+)
(23) 3-Z-[1-(4-ethoxycarbonyl-anilino)-1-phenyl-methylene]-
6-carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example II and
ethyl 4-amino-benzoate
C25H21N304
Mass spectrum: m/z = 427 (m+)
(24) 3-Z-[1-(4-carboxy-anilino)-1-phenyl-methylene]-
6 -carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example II and
4-amino-benzoic acid
Rf value: 0.11 (silica gel, methylene chloride/methanol = 9:1)
C23H17N304
Mass spectrum: m/z = 398 (m-H+)

(25) 3-Z-[1-(4-benzylcarbamoyl-anilino)-1-phenyl-methylene]-
6 -carbamoyl- 2 -indolinone
Prepared from the resin obtained according to Example II and
4-amino-benzoic acid-benzylamide
R£ value: 0.21 (silica gel, methylene chloride/methanol = 9:1)
C30H24N4O3
Mass spectrum: m/z = 488 (m+)
(26) 3-Z-[1-(cyclohexyl-amino)-1-phenyl-methylene]-6-
carbamoyl-2-indolinone
Prepared from the resin obtained according to Example II and
cyclohexylamine
Rf value: 0.60 (silica gel, methylene chloride/methanol = 9:1)
C22H23N302
Mass spectrum: m/z = 361 (m+)
(27) 3-Z-[1-(4-amino-cyclohexyl-amino)-1-phenyl-methylene]-
6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-amino-cyclohexylamine
C22H24N402
Mass spectrum: m/z = 376 (m+)
(28) 3-Z-[1-(N-methyl-piperidine-4-yl-amino)-1-phenyl-
methylene] -6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
4-amino-1-methyl-piperidine
Rf value: 0.15 (silica gel, methylene chloride/methanol =4:1)
C22H24N402
Mass spectrum: m/z = 376 (m+)
(29) 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-methyl-
methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example 11(2)
and 4-(piperidin-1-yl-methyl)-aniline
Rf value: 0.3 0 (silica gel, methylene chloride/methanol = 4:1)

C23H2SN402
Mass spectrum: m/z = 390 (m+)
(30) 3-Z-[1-(3-dimethylaminomethyl-anilino)-1-methyl-
methylene]-6-carbamoyl-2 -indolinone-trifluoroacetate
Prepared from the resin obtained according to Example 11(2)
and 3-dimethylaminomethyl-aniline
Rf value: 0.51 (silica gel, methylene chloride/methanol = 4:1)
C H N O "
Mass spectrum: m/z = 351 (m+H+)
(31) 3-Z-[1-(4-(N-methyl-N-benzyl-aminomethyl)-anilino)-
1-methyl-methylene]-6 -carbamoyl-2 -indolinone-trifluoroacetate
Prepared from the resin obtained according to Example 11(2)
and 4-(N-methyl-N-benzyl-aminomethyl)-aniline
Rf value: 0.73 (silica gel, methylene chloride/methanol = 4:1)
C26H26N402
Mass spectrum: m/z = 426 (m+)
(32) 3-Z-[1-(4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)-
amino)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone-
trifluoroacetate
Prepared from the resin obtained according to Example 11(2)
and 4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)-amino)-
aniline
C22H27N504S
Mass spectrum: m/z = 458 (m+H+)
(33) 3-Z- [1-(4-chloro-anilino)-1-methyl-methylene]-6-
carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example 11(2)
and 4-chloro-aniline
Rf value: 0.10 (silica gel, methylene chloride/methanol = 9:1)
C17H14C1N302
Mass spectrum: m/z = 327/329 (m+)

(34) 3-Z-[1-(3-chloro-anilino)-1-methyl-methylene]-6-
carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example 11(2)
and 3-chloro-aniline
Rf value: 0.11 (silica gel, methylene chloride/methanol = 9:1)
C17H14C1N302
Mass spectrum: m/z = 327/329 (m+)
(35) 3-Z-[1-(4-methoxycarbonyl-anilino)-1-methyl-methylene]-
6 -carbamoyl-2-indolinone
Prepared from the resin obtained according to Example 11(2)
and methyl 4-amino-benzoate
Rf value: 0.11 (silica gel, methylene chloride/methanol = 9:1)
C19H17N304
Mass spectrum: m/z = 351 (m+)
(36) 3-Z-[1-(4-carboxy-anilino)-1-methyl-methylene]-6-
carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example 11(2)
and 4-amino-benzoic acid
C18H15N304
Mass spectrum: m/z = 336 (m-H+)
(37) 3-Z-[1-(4-methyl-3-nitro-anilino)-1-methyl-methylene]-
6-carbamoyl-2-indolinone
Prepared from the resin obtained according to Example 11(2)
and 4-methyl-3-nitro-aniline
R£ value: 0.82 (silica gel, methylene chloride/methanol =4:1)
C1BH16N404
Mass spectrum: m/z = 352 (m+)
(38) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-propyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example 11(4)
and 4-(piperidin-1-yl-methyl)-aniline
Rf value: 0.37 (silica gel, methylene chloride/methanol =4:1)

C2SH30N4O2
Mass spectrum: m/z = 418 (m+)
(39) 3-Z-[1-(3-dimethylaminomethyl-anilino)-1-propyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example 11(4)
and 3-dimethylaminomethyl-aniline
R£ value: 0.42 (silica gel, methylene chloride/methanol =4:1)
C22H26N402
Mass spectrum: m/z = 3 78 (m+)
(40) 3-Z-[1-(4-(N-methyl-N-benzyl-aminomethyl)-anilino)-1-pro-
pyl-methylene]-6-carbamoyl-2 -indolinone-trifluoroacetate
Prepared from the resin obtained according to Example 11(4)
and 4-(N-methyl-N-benzyl-aminomethyl)-aniline
Rf value: 0.81 (silica gel, methylene chloride/methanol =4:1)
C28H3oN402
Mass spectrum: m/z = 454 (m+)
(41) 3-Z- [1-(4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)-
amino)-anilino)-1-propyl-methylene]-6-carbamoyl-2-indolinone-
trif luoroace tat e
Prepared from the resin obtained according to Example 11(4)
and 4-(N-methylsulphonyl-N-(2-dimethylamino-ethyl)-amino)-
aniline
Rf value: 0.59 (silica gel, methylene chloride/methanol = 4:1)
C24H31Ns04S
Mass spectrum: m/z = 486 (m+H+)
(42) 3-Z-[1-(4-chloro-anilino)-1-propyl-methylene]-6-
carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example 11(4)
and 4-chloro-aniline
Rf value: 0.17 (silica gel, methylene chloride/methanol = 9:1)
C19H18C1N302
Mass spectrum: m/z = 355/357 (m+)

(43) 3-Z-[1-(3-chloro-anilino)-1-propyl-methylene]-6-
carbamoyl- 2 -indolinone
Prepared from the resin obtained according to Example 11(4)
and 3-chloro-aniline
Rf value: 0.12" (silica gel, methylene chloride/methanol = 9:1)
C19H18C1N302
Mass spectrum: m/z = 355/357 (m+)
(44) 3-Z-[1-(4-methoxycarbonyl-anilino)-1-propyl-methylene]-
6 -carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example 11(4) and methyl 4-amino-benzoate " Rf value: 0.8 (silica gel, methylene chloride/methanol = 4:1) C21H21N304 Mass spectrum: m/z = 379 (m+)
(45) 3-Z-[1-(4-carboxy-anilino)-1-propyl-methylene]-
6 -carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example 11(4)
and 4-amino-benzoic acid
C20H19N3O4
Mass spectrum: m/z = 364 (m-H+)
(46) 3-Z-[1-(4-methyl-3-nitro-anilino)-1-propyl-methylene]-
6 -carbamoyl-2 -indolinone
Prepared from the resin obtained according to Example 11(4)
and 4-methyl-3-nitro-aniline
Rf value: 0.86 (silica gel, methylene chloride/methanol = 4:1)
C30H20N4O4
Mass spectrum: m/z = 380 (m+)

Example 2
3-Z-[1-(3-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene]- 6-carbamoyl-2-indolinone-trifluoroacetate
2.0 g of resin obtained according to Example II are reacted
analogously to Example 1 with 2.0 g of 3-aminobenzyl alcohol
in 20 ml of dimethylformamide for 22 hours at 70°C. Then the
solvent is suction filtered and the resin is washed several
times with dimethylformamide and methylene chloride. Then 200
mg of the moist charged resin are suspended in 2 ml of
methylene chloride and left to stand with 0.2 ml of
methanesulphonic acid chloride and 0.1 ml of triethylamine for
2 hours at room temperature. Then the resin is washed several
times with methylene chloride, suspended in 2 ml of methylene
chloride and combined with 0.2 ml of piperidine. After 1 hour
the resin is washed with methylene chloride and
dimethylformamide and then treated with trifluoroacetic acid
analogously to Example 1.
Yield: 15 mg
Rf value: 0.3 0 (silica gel, methylene chloride/methanol = 4:1)
C28H28N402
Mass spectrum: m/z = 452 (m+)
The following compounds are prepared analogously to Example 2:
(1) 3-Z-[1-(3-(diethylaminomethyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
diethylamine
Rf value: 0.80 (silica gel, methylene chloride/methanol =4:1)
C27H28N402
Mass spectrum: m/z = 440 (m+)
(2) 3-Z-[1-(3-(benzylaminomethyl)-anilino)-1-phenyl-
methylene]-6-carbamoyl-2-indolinone-trifluoroacetate

Prepared from the resin obtained according to Example II and
benzylamine
Rf value: 0.80 (silica gel, methylene chloride/methanol =4:1)
C30H26N4O2
Mass spectrum: m/z = 474 (m+)
(3) 3-Z- [1- (3- (N-methyl-N-benzyl-atninomethyl) -anilino) -
1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
N-methyl-benzylamine
Rf value: 0.80 (silica gel, methylene chloride/methanol =4:1)
C31H28N402
Mass spectrum: m/z = 488 (m+)
(4) 3-2- [1-(3-(butylaminomethyl)-anilino)-1-phenyl-methylene]-
6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
butylamine
Rf value: 0.40 (silica gel, methylene chloride/methanol =4:1)
C27H28N402
Mass spectrum: m/z = 440 (m+)
(5) 3-Z-[l-(3-(aminomethyl)-anilino)-1-phenyl-methylene]-
6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and
ammonia
C23H20N402
Mass spectrum: m/z = 3 85 (m+H+)
(6) 3-Z- [1-(3-(N-(3-dimethylaminopropyl)-N-methyl-amino¬
methyl) -anilino)-1-phenyl-methylene]- 6-carbamoyl^-indolinone-
trifluoroacetate
Prepared from the resin obtained according to Example II and
l-dimethylamino-3-methylaminopropane
Rf value: 0.67 (silica gel, methylene chloride/methanol =4:1)
C2gH33N502

Mass spectrum: m/z = 484 (m+H+)
(7) 3-Z-[1-(3-(N-(2-dimethylaminoethyl)-N-methyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone-trifluoroacetate
Prepared from the resin obtained according to Example II and 1-dimethylamino-2-methylaminoethane Rf value: 0.4 0 (silica gel, methylene chloride/methanol = 4:1)
Mass spectrum: m/z = 470 (m+H+)
Example 3
3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene] -6-ethoxycarbonvl-2-indolinone ____
1.5 g of l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 1.1 g of 4-(piperidin-1-yl-
methyl)-aniline are dissolved in 15 ml of dimethylformamide
and stirred for 45 minutes at 100°C. After cooling 5.0 ml of
piperidine are added and the mixture is stirred for another 3
hours at room temperature. The solvent is removed and the
residue purified over an aluminium oxide column (activity:
2-3) with methylene chloride/ethanol (100:3) as eluant.
Yield: 1.1 g (58% of theory),
Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol =
100:3)
C30H31N3O3
Mass spectrum: m/z = 481 [M+]
The following compounds are prepared analogously to Example 3:
(1) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-ethoxycarbonyl-2-indolinone and 4-bromoaniline Rf value: 0.4 (silica gel, toluene/ethyl acetate = 5:1)

C24Hx3BrN203
Mass spectrum: m/z = 462/464 [M+]
(2) 3-Z-[1-(3-(dimethylaminomethyl) -anilino)-1-phenyl-
methylene]-6 -ethoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 3-(dimethylaminomethyl)-
aniline
Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol =
30:1)
C27H27N303
ESI mass spectrum: m/z = 442 [M+H+]
(3) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene) -6~
ethoxycarbonyl-2-indolinone and 4-(dimethylaminomethyl)-
aniline
R£ value: 0.7 (aluminium oxide, ethyl acetate/ethanol = 20:1)
C27H27N303
ESI mass spectrum: m/z = 442 [M+H+]
(4) 3-Z- [1- (4- [ (2,6-dimethyl-piperidin-l-yl)-methyl]-anilino)
1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from- l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-[ (2 , 6-dimethyl-piperidin-l-
yl) -methyl]-aniline
Rf value: 0.6 (silica gel, methylene chloride/ethanol = 5:1)
C32H35N303
Mass spectrum: m/z = 509 [M+]
(5) 3-Z- [1-(4-(2-dimethylamino-ethyl)-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-ethoxycarbonyl-2-indolinone and 4-(2-dimethylamino-ethyl)-aniline

Rf value: 0.2 (silica gel, methylene chloride/ethanol =5:1)
C28H29N303
Mass spectrum: m/z = 455 [M+]
(6) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(l-ethoxy-1-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-acetyl-amino)-aniline
Rf value: 0.4 (aluminium oxide, methylene chloride/ethanol =
20:1)
C30H32N4O4
Mass spectrum: m/z = 512 [M+]
(7) 3-Z-[1-(4-tert.butyloxycarbonyl-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4 -tert.butyloxycarbonyl-
aniline
Rf value: 0.4 (aluminium oxide, methylene chloride/ethanol =
4 0:1)
Mass spectrum: m/z = 484 [M+]
(8) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-(3-dimethylamino-propyl)-
N-acetyl-amino)-aniline
RBvalue: 0.2 (aluminium oxide, methylene chloride/ethanol =
4C:1)
C11H34N404
Mass spectrum: m/z = 526 [M+]

(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-)-1-phenyl-methylene]-6-ethoxycarbonyl-2-
l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
-2-indolinone and N-(2-dimethylamino-ethyl)-N-
1-p-phenylenediamine
(aluminium oxide, methylene chloride/ethanol =
m/z = 548 [M+]
-(4-methyl-piperazin-l-yl)-anilino)-1-phenyl-thoxycarbonyl-2 -indolinone
1-acetyl-3-(1-ethoxy-l-phenylmethylene)-6--2-indolinone and 4-(4-methyl-piperazin-l-yl)-
aluminium oxide, ethyl acetate)
rum: m/z = 483 [M+H+]
-(N-(2-dimethylamino-ethyl)-N-methyl-amino)-lyl-methylene]- 6-ethoxycarbonyl-2 -indolinone L-acetyl-3-(1-ethoxy-l-phenylmethylene)-6--2-indolinone and 4-(N-(2-dimethylamino-ethyl)-i-aniline aluminium oxide, methylene chloride/ethanol =
:um: m/z = 485 [M+H+]
- (N-(3-dimethylamino-propyl)-N-methyl-amino)-lyl-methylene]-6-ethoxycarbonyl-2-indolinone L-acetyl-3-(1-ethoxy-l-phenylmethylene)-6--2-indolinone and 4-(N-(3-dimethylamino-propyl)--aniline aluminium oxide, ethyl acetate)

(9) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
methylsulphonyl-p-phenylenediamine
R£ value: 0.3 (aluminium oxide, methylene chloride/ethanol =
40:1)
C29H32N405S
Mass spectrum: m/z = 548 [M+]
(10) 3-Z-[1-(4-(4-methyl-piperazin-l-yl)-anilino)-l-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(4-methyl-piperazin-l-yl)-
aniline
Rf value: 0.3 (aluminium oxide, ethyl acetate)
C29H30N4O3
ESI mass spectrum: m/z = 483 [M+H+]
(11) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-methyl-amino)-aniline
Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol =
20:1)
C29H32N403
ESI mass spectrum: m/z = 485 [M+H+]
(12) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-(3-dimethylamino-propyl)-
N-methyl-amino)-aniline
Rf value: 0.5 (aluminium oxide, ethyl acetate)

C30H34N4O3
ESI mass spectrum: m/z = 499 [M+H+]
(13) 3-Z- [1-(4-(N-methyl-acetylamino)-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-amino-N-methyl-acetanilide
Rf value: 0.3 (silica gel, methylene chloride/ethanol = 15:1)
C27H25N304
Mass spectrum: m/z = 455 [M+]
(14) 3-Z- [1-(4-(N-methyl-methylsulphonylamino)-anilino)-1-
phenyl-methylene]-6-e thoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and N-(4-aminophenyl)-N-methyl-
methanesulphonamide
Rf value: 0.8 (aluminium oxide, ethyl acetate)
C26H25N305S
Mass spectrum: m/z ■= 491 [M+]
(15) 3-Z- [1- (4-(N- (3-dimethylamino-propyl)-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and N-(3-dimethylamino-propyl)-N-
methylsulphonyl-p-phenylenediamine
Rf value: 0.6 (silica gel, methylene chloride/ethanol/ammonia
=5:2:0.01)
C30H34N4O5S
ESI mass spectrum: m/z = 563 [M+H+]
(16) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-
methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-
dimethylaminocarbonylmethyl-N-methylsulphonyl)-amino)-aniline
Rf value: 0.6 (silica gel, methylene chloride/ethanol = 10:1)
C29H30N4O6S
ESI mass spectrum: m/z = 561 [M-H~]
(17) 3-Z-[1-(4-(imidazol-4-yl)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl- 2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(imidazol-4-yl)-aniline
Rr value: 0.5 (silica gel, methylene chloride/ethanol/ammonia
= 10:1:0.01)
C27H22N403
Mass spectrum: m/z = 450 [M+]
(18) 3-Z-[1-(4-(tetrazol-5-yl)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(tetrazol-5-yl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/ethanol = 5:1)
C25H20N6O3
ESI mass spectrum: m/z = 451 [M-JT]
(19) 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)-anilino)-1-
phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-benzyl-N-methyl-
aminomethyl) -aniline
Rf value: 0.4 (silica gel, methylene chloride/ethanol = 10:1)
C33H31N303
ESI mass spectrum: m/z = 516 [M-H~]
(20) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propionyl-amino)-
aniline)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2 -indol inone and 4- [N- (2-dimeth.ylamino-ethyl) -
N-propionyl-amino]-aniline
Rf value: 0.2 (silica gel, methylene chloride/ethanol = 5:1)
C31H34N404
ESI mass spectrum: m/z = 525 [M-H~]
(21) 3-Z-[1-(4-(pyrrolidin-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(pyrrolidin-1-yl-methyl)-
aniline
Rf value: 0.1 (silica gel, methylene chloride/ethanol = 5:1)
C29H29N303
ESI mass spectrum: m/z = 466 [M-H"]
(22) 3-Z-[1-(4-(N-methyl-N-phenethyl-aminomethyl)-anilino)-1-
phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-phenethyl-N-methyl-
aminomethyl)-aniline
Rf value: 0.4 (silica gel, methylene chloride/ethanol = 10:1)
C34H33N3O3
ESI mass spectrum: m/z = 530 [M-H"]
(23) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and N-dimethylaminomethylcarbonyl-
N-methyl-p-phenylenediamine
Rf value: 0.1 (silica gel, methylene chloride/ethanol = 10:1)
C23H30N4O4
ESI mass spectrum: m/z = 497 [M-H"]

(24) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-ethylsulphonyl-
amino)-andlino)-l-phenyl-methylene]-6-ethoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
ethylsulphonyl-p-phenylenediamine
Rf value: 0.6 (silica gel, methylene chloride/ethanol = 5:1)
C30H34N4O5S
ESI mass spectrum: rh/z = 561 [M-H"]
(25) 3-Z-[1-(4-(N-tert.butoxycarbonyl-N-ethyl-aminomethyl)-
anilino)-l-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and 4-(N-tert.butoxycarbonyl-N-
ethyl-aminomethyl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C32H35N3Os
ESI mass spectrum: m/z = 54 0 [M-H"]
(26) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-ethyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-ethyl-methylene)-6-
ethoxycarbonyl-2-indolinone and 4-(piperidin-1-yl-methyl)-
aniline
Rf value: 0.9 (silica gel, methylene chloride/ethanol = 5:1)
C26H31N303
ESI mass spectrum: m/z = 432 [M-H"]
(27) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-
amino)-anilino)-1-ethyl-methylene]-6-ethoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-ethyl-methylene)-6-
ethoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
methylsulphonyl-p-phenylenediamine
Rf value: 0.3 (silica gel, methylene chloride/ethanol = 5:1)
C2SH32N405S

ESI mass spectrum: m/z = 499 [M-H~]
(28) 3-2-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(dimethylaminomethyl)-
aniline
R£ value: 0.6 (silica gel, methylene chloride/methanol = 5:1)
C26H2SN303
ESI mass spectrum: m/z = 428 [M+H+]
(29) 3-Z-[1-(4-[(2,6-dimethyl-piperidin-l-yl)-methyl]-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)~6-
methoxycarbonyl-2-indolinone and 4-[(2,6-dimethyl-piperidin-l-
yl) -methyl]-aniline
Rf value: 0.5 (RP 8, methanol/five percent saline solution =
4:1)
C31H33N303
ESI mass spectrum: m/z = 4 96 [M+H+]
(30) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-ti¬me thyl sulphonyl -p-phenylenediamine
Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1) C28H30N4O5S ESI mass spectrum: m/z = 533 [M-H~]
(31) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(3-dimethylamino-propyl)-N-
methylsulphonyl-p-phenylenediamine
Rf value: 0.5 (aluminium oxide, methylene chloride/methanol =
30:1)
C29H32N405S
ESI mass spectrum: m/z = 547 [M-H~]
(32) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-
methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-dimethylaminocarbonyl¬methyl -N-methylsulphonyl) -amino)-aniline
Rf value: 0.5 (aluminium oxide, methylene chloride/methanol = 20:1) C28H28N4OsS ESI mass spectrum: m/z = 547 [M-IT]
(33) 3-Z-[1-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-acetyl-N-
dimethylaminocarbonylmethyl)-amino)-aniline
R£ value: 0.6 (silica gel, methylene chloride/methanol = 10:1)
C29H28N4Os
ESI mass spectrum: m/z = 511 [M-H~]
(34) 3-Z- [1-(4- (N-dimethylaminocarbonylmethyl-amino)-anilino)-
1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-dimethylaminocarbonyl¬methyl) -amino)-aniline
Rf value: 0.6 (aluminium oxide, methylene chloride/methanol = 30:1) C27H26N404

ESI mass spectrum: m/z = 469 [M-H"]
(35) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(3-dimethylamino-propyl)-N-
acetyl-p-phenylenediamine
Rf value: 0.5 (aluminium oxide, methylene chloride/methanol =
20:1)
C30H33N4O4
ESI mass spectrum: m/z = 511 [M-H"]
(36) 3-Z-[1-(4-(N-methylaminocarbonylmethyl-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-methylaminocarbonylmethyl-
N-methylsulphonyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C27H26N406S
ESI mass spectrum: m/z = 533 [M-H"]
(37) 3-Z-[l-(4-((imidazolidin-2,4-dion-5-ylidene)-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((imidazolidin-2,4-dion-5-
ylidene)-methyl)-aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1)
C27H20N4O5
ESI mass spectrum: m/z = 479 [M-H"]
(38) 3-Z- [1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-
amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-
indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-((2-dimethylamino-ethyl)-
carbonyl)-N-methyl-p-phenylenediamine
Rf value: 0.5 (aluminium oxide, methylene chloride/methanol =
20:1)
C29H30N4O4
ESI mass spectrum: m/z = 497 [M-H"]
(39) 3-Z-[l-(4-(N-tert.butoxycarbonyl-aminomethyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-tert.butoxycarbonyl-aminomethyl) -aniline
Rf value: 0.3 (aluminium oxide, methylene chloride/methanol = 20:1) C25H29N305 ESI mass spectrum: m/z = 498 [M-H"]
(40) 3-Z-[1-(4-(2-oxo-pyrrolidin-l-yl-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(2-oxo-pyrrolidin-l-yl-
methyl) -aniline
Rf value: 0.3 (silica gel, methylene chloride/methanol = 20:1)
C28H2SN304
ESI mass spectrum: m/z = 466 [M-H"]
(41) 3-Z-[l-(4-(N-aminocarbonylmethyl-N-methy1sulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-aminocarbonylmethyl-N-
methylsulphonyl-p-phenylenediamine
Rf value: 0.7 (silica gel, methylene chloride/methanol = 5:1)
C26H24N406S
ESI mass spectrum: m/z = 519 [M-H"]

(42) 3-Z-[1-(4-(thiomorpholin-4-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(thiomorpholin-4-yl-
methyl)-aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol = 15:1)
C28H27N303S
ESI mass spectrum: jh/z = 484 [M-H~]
(43) 3-Z-.[l- (4- (1, l-dioxo-thiomorpholin-4-yl-methyl) -anilino) -
1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(1,l-dioxo-thiomorpholin-4-
yl-methyl)-aniline
Rf value-. 0.5 (silica gel, methylene chloride/methanol = 10:1)
C2BH27N305S
ESI mass spectrum: m/z = 516 [M-H~]
(44) 3-2- [1- (4- (N-cyanomethyl-N-methylsulphonyl-amino)-
anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-cyanomethyl-N-methyl-
sulphonyl-p-phenylenediamine
Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1)
C2SH22N405S
ESI mass spectrum: m/z = 501 [M-H"]
(45) 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylaminomethyl)-
anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-ethyl-N-
tert.butoxycarbonyl-aminomethyl)-aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol =10:1)
C31H33N305
ESI mass spectrum: m/z = 526 [M-H"]

(46) 3-Z- [1-(4-(N-benzyl-N-raethyl-aminomethyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-benzyl-N-methyl-
aminomethyl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C32H29N303
ESI mass spectrum: rti/z = 502 [M-H"]
(47) 3-Z- [1-(4-(l-oxo-thiomorpholin-4-yl-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(l~ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(l-oxo-thiomorpholin-4-yl-
methyl)-aniline
R£ value: 0.7 (silica gel, methylene chloride/methanol = 10:1)
C28H27N304S
ESI mass spectrum: m/z = 500 [M-H"]
(48) 3-Z- [1-(4-(2-(imidazol-4-yl)-ethyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(2-(imidazol-4-yl)-ethyl)-
aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol = 5:1)
C2aH24N403
ESI mass spectrum: m/z = 463 [M-H"]
(49) 3-Z-[1-(4-(morpholin-4-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(morpholin-4-yl-methyl)-
aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C28H27N304
ESI mass spectrum: m/z = 468 [M-H"]

(50) 3-Z-[1-(4-((4-methyl-piperazin-l-yl)-methyl)-anilino)-1-
phenyl -methylene] - 6 -methoxycarbonyl"- 2 - indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((4-methyl-piperazin-l-yl) -
methyl)-aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol 5:1)
C29H30N4O3
ESI mass spectrum: m/z = 481 [M-H~]
(51) 3-Z- [1- (4- ( (2-(N-benzyl-N-methyl-amino) -ethyl)-N-
methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(2-(N-benzyl-N-methyl-amino) -ethyl)-N-methylsulphonyl-amino)-aniline
Rf value: 0.7 (silica gel, methylene chloride/methanol = 10:1) C34H34N405S ESI mass spectrum: m/z = 609 [M-H"]
(52) 3-Z- [1-(4-cyclohexylamino-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-cyclohexyl-p-phenylenediamine Rf value: 0.8 (silica gel, methylene chloride/methanol = 10:1)
ESI mass spectrum: m/z = 451 [M-H"]
(53) 3-Z-[1-(4-(pyridin-4-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(pyridin-4-yl-methyl)-
aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol/ammonia
= 5:1:0.01)

C29H23N303
ESI mass spectrum: m/z = 460 [M-H"]
(54) 3-Z- [1- (4-(imidazol-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(imidazol-1-yl-methyl)-
aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol/ammonia
= 10:1:0.01)
C27H22N403
ESI mass spectrum: m/z = 449 [M-H"]
(55) 3-Z- [1-(4-(imidazol-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(imidazol-1-yl-methyl)-
aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol/ammonia
=10:1:0.01)
C27H22N403
ESI mass spectrum: m/z = 449 [M-H"]
(56) 3-Z-[1-(N-methyl-piperidine-4-yl-amino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-amino-1-methyl-piperidine
Rf value: 0.3 (silica gel, methylene chloride/methanol = 5:1)
C23H25N303
ESI mass spectrum: m/z = 3 90 [M-H"]
(57) 3-Z- [1-(4-(imidazol-4-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(imidazol-4-yl-methyl)-aniline

Rf value: 0.2 (silica gel, methylene chloride/methanol = 5:1)
C27H22N403
ESI mass spectrum: m/z = 449 [M-H~]
(58) 3-Z-[1-(4-((4-hydroxy-piperidin-l-yl)-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((4-hydroxy-piperidin-l-yl) -methyl)-aniline/
Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1) C29H29N303 ESI mass spectrum: m/z = 482 [M-JT]
(59) 3-Z-[1-(4-((4-methoxy-piperidin-l-yl)-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((4-methoxy-piperidin-l-yl) -methyl)-aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1) C30H31N3O4 ESI mass spectrum: m/z = 496 [M-H"]
(60) 3-Z-[1-(4-benzyl-anilino)-1-phenyl-methylene]-6-methoxy-
carbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-benzyl-aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol - 10:1)
C30H24N2O3
Melting point: 224°C
(61) 3-Z-[1-(4-(N-(3-trifluoroacetylamino-propyl)-N-
methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-(3-trifluoroacetylamino-propyl) -N-methylsulphonyl-p-phenylenediamine

Rf value: 0.5 (aluminium oxide, methylene chloride/methanol =
20:1)
C29H27F3N406S
ESI mass spectrum: m/z = 615 [M-H"]
(62) 3-Z- [1-(4-tert.butoxycarbonylmethyl-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
ethoxycarbonyl-2-indolinone and tert.butyl 4-
aminophenylacetate
Rr value: 0.5 (aluminium oxide, ethyl acetate)
C30H30N2O5
ESI mass spectrum: m/z = 497 [M-H"]
(63) 3-Z- [1-(4-tert.butoxycarbonyl-anilino)-1-ethyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-ethylmethylen)-6-
ethoxycarbonyl-2-indolinone" and 4-tert.butoxycarbonyl-aniline
R£ value: 0.4 (aluminium oxide, methylene chloride/ethanol =
20:1)
C25H28N205
ESI mass spectrum: m/z = 435 [M-H"]
(64) 3-Z- [1- (4- (4-tert.butoxycarbonyl-piperazin-1-yl-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(4-tert.butoxycarbonyl-
piperazin-1-yl-methyl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C33H36N405
ESI mass spectrum: m/z = 567 [M-H"]
(65) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(1-methyl-imidazol-2-yl)-
aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1)
C27H22N403
ESI mass spectrum: m/z = 449 [M-H"]
(66) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-
amino)-3-nitro-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-
2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 6-(N-(2-dimethylamino-ethyl)-
N-methylsulphonyl-amino)-3-amino-nitrobenzene
Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1)
C28H29Ns07S
ESI mass spectrum: m/z = 578 [M-H"]
(67) 3-2-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-
amino) -3-amino-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-
2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-methylsulphonyl-amino)-3 -amino-ani1ine
Rf value: 0.5 (aluminium oxide, methylene chloride/methanol =
20:1)
C28H31N505S
ESI mass spectrum: m/z = 548 [M-H"]
(68) 3-Z-[1-(4-((3-(N-benzyl-N-methyl-amino)-propyl)-N-methyl¬
sulphonyl-amino) -anilino)-l-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(3-(N-benzyl-N-methyl-
amino)-propyl)-N-methylsulphonyl-amino)-aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1)
C3SH36N405S

ESI mass spectrum: m/z = 623 [M-JT]
(69) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-
amino)-3-chloro-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-methylsulphonyl-amino)-3-chloro-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C28H29C1N40SS
ESI mass spectrum: m/z = 567/569 [M-H"]
(70) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-
dimethylaminomethylcarbonyl-N-methyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C28H28N404
ESI mass spectrum: m/z = 483 [M-H"]
(71) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-acetyl-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C29H30N4O4
ESI mass spectrum: m/z = 497 [M-H"]
(72) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propionyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-propionyl-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C30H32N4O4
ESI mass spectrum: m/z = 511 [M-H"]
(73) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-butyryl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-butyryl-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C31H34N404
ESI mass spectrum: m/z = 525 [M-H"]
(74) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-isobutyryl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-isobutyryl-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C31H34N404
ESI mass spectrum: m/z = 525 [M-H"]
(75) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzoyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-benzoyl-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C34H32N404
ESI mass spectrum: m/z = 559 [M-H"]
(76) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-
amino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-amino-aniline

R£ value: 0.5 (aluminium oxide, methylene chloride/methanol =
20:1)
C29H31Ns04
ESI mass spectrum: m/z = 512 [M-H~]
(77) 3-Z-[1-(4-(4-hydroxymethyl-piperidin-l-yl-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(4-hydroxymethyl-piperidin-
1-yl-methyl-amino)-aniline
Rf value: 0.3 (silica gel, methylene chloride/methanol = 5:1)
C30H31N3O4
ESI mass spectrum.: m/z = 496 [M-H~]
(78) 3-Z-[1-(4-(2-(4-hydroxy-piperidin-l-yl)-ethyl)-anilino)-
1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(2-(4-hydroxy-piperidin-l-
yl) -ethyl-amino) -aniline
Rf value: 0.3 (silica gel, methylene chloride/methanol =5:1)
C30H31N3O4
ESI mass spectrum: m/z = 496 [M-H~]
(79) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
propylsulphonyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C30H34N4O5S
ESI mass spectrum: m/z = 561 [M-H~]
(80) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-butylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
butylsulphonyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C31H36N405S
ESI mass spectrum: m/z = 575 [M-H"]
(81) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-phenylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
phenylsulphonyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C33H32N4OsS
ESI mass spectrum: m/z = 595 [M-H"]
(82) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
benzylsulphonyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C34H3«N4OsS
ESI mass spectrum: m/z = 609 [M-H"]
(83) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-ethylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(2-dimethylamino-ethyl)-N-
ethylsulphonyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C29H32N405S
ESI mass spectrum: m/z = 547 [M-H"]

(84) 3-Z-[1-(4-((imidazolidin-2, 4-dion-5-yl)-methyl)-anilino)-
1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((imidazolidin-2,4-dion-5-
yl)-methyl)-aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1}
C27H22N405
ESI mass spectrum: jh/z = 481 [M-H~]
(85) 3-Z- [1-(4-((3-hydroxy-pyrrolidin-l-yl)-methyl)-anilino)-
1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-
methoxycarbony1-2-indolinone and 4-((3-hydroxy-pyrrolidin-l-yl) -methyl)-aniline
Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1) C28H27N304 ESI mass spectrum: m/z = 468 [M-H"]
(86) 3-Z- [1-(4-(cyclohexylyl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(cyclohexyl-methyl)-aniline (Eur. J. Med. Chem. Chim. Ther. 1992, 27, 537-544) Rj. value: 0.6 (silica gel, methylene chloride/methanol = 10:1) C30H30N2O3 ESI mass spectrum: m/z = 465 [M-H~]
(87) 3-Z- [1-(4-(cyclohexyl-carbonyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(cyclohexyl-carbonyl)-
aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C30H28N3O4
ESI mass spectrum: m/z = 479 [M-H"]

(88) 3-Z-[1-(4-diethylaminomethyl-anilino)-1-phenyl-
methylene]- 6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(l~ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(diethylamino-methyl)-
aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1)
C28H29N303
ESI mass spectrum: rti/z = 454 [M-H~]
(89) 3-Z-[1-(4-(N-(n-hexyl)-N-methyl-aminomethyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(n-hexyl)-N-methyl-aminomethyl) -aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol = 10:1) C31H35N303 ESI mass spectrum: m/z = 496 [M-H~].
(90) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(furan-2-
carbonyl)-amino)-anilino)-1-phenyl-methylene] -6-
methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbony1-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-(furan-2-carbonyl)-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C32H30N4O5
ESI mass spectrum: m/z = 549 [M-H~]
(91) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(2-methoxy-
benzoyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxy-
carbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-N-(2-methoxy-benzoyl)-amino)-aniline Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)

C35H34N405
ESI mass spectrum: m/z = 589 [M-H"]
(92) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(pyridine-3-
carbonyl)-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl) -
N-(pyridine-3-carbonyl)-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C33H31Ns04
ESI mass spectrum: m/z = 560 [M-H"]
(93) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-(phenyl-acetyl)-amino)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C35H34N404
ESI mass spectrum: m/z = 573 [M-H"]
(94) 3-Z-[1-(4-(N-ethyl-N-methyl-aminomethyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-ethyl-N-methyl-
aminomethyl) -aniline
Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1)
C27H27N303
ESI mass spectrum: m/z = 440 [M-H"]
(95) 3-Z- [1-(4-(imidazol-2-yl)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(imidazol-2-yl)-aniline
R£ value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C26H20N4O3
ESI mass spectrum: m/z = 435 [M-H"]
(96) 3-Z-[1-(4-(l-ethyl-imidazol-2-yl)-anilino)-l-phenyl-
methylene]- 6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(i-ethyl-imidazol-2-yl)-
aniline ."
R£ value: 0.4 (silica gel, methylene chloride/methanol = 10:1)
C23H24N403
ESI mass spectrum: m/z = 463 [M-H"]
(97) 3-Z-[1-(4-(l-benzyl-imidazol-2-yl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(l-benzyl-imidazol-2-yl)-
aniline
Rf value: 0.3 (silica gel, methylene chloride/methanol = 20:1)
C33H26N403
ESI mass spectrum: m/z = 525 [M-H"]
(98) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-
isopropylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N- (2-d.imethylamino-ethyl) -N-
isopropylsulphonyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C30H34N4OsS
ESI mass spectrum: m/z = 561 [M-H"]
(99) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N-methyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(piperidin-1-yl-
methylcarbonyl)-N-methyl-p-phenylenediamine
R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C31H32N404
ESI mass spectrum: m/z = 523 [M-H~]
(100) 3-Z- [1-(4-(N-(morpholin-4-yl-methylcarbonyl)-N-methyl-
amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(morpholin-4-yl-
methylcarbonyl)-N-methyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C30H30N4Os
ESI mass spectrum: m/z = 525 [M-H~]
(101) 3-Z- [1-(4-(N-((4-benzyl-piperazin-l-yl)-methylcarbonyl) -
N-methyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbony1-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-((4-benzyl-piperazin-l-yl) -
methylcarbonyl)-N-methyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C37H37N504
ESI mass spectrum: m/z = 614 [M-H~]
(102) 3-Z- [1-(4-(N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl-
amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(pyrrolidin-1-yl-
methylcarbonyl)-N-methyl-p-phenylenediamine
R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C3oH3oN404
ESI mass spectrum: m/z = 509 [M-H~]

(103) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-
bromo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-(2-dimethylamino-ethyl)-
N-acetyl-amino)-3-bromo-aniline
Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1)
C29H29BrN404
ESI mass spectrum: m/z = 575/577 [M-H~]
(104) 3-Z-[1-(4-(5-methyl-imidazol-4-yl)-anilino)-1-phenyl-
methylene] -6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(5-methyl-imidazol-4-yl)-
aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia
=10:1:0.01)
C27H22N403
ESI mass spectrum: m/z = 449 [M-H~]
(105) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-
isopropyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-((2-dimethylamino-ethyl)-
carbonyl)-N-isopropyl-p-phenylenediamine
Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1)
C31H34N404
ESI mass spectrum: m/z = 525 [M-H"]
(106) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-
benzyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-
2-indolinone

Prepared from 1-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-((2-dimethylamino-ethyl)-
carbonyl)-N-benzyl-p-phenylenediamine
Rf value: 0.1 (silica gel, methylene chloride/methanol = 10:1)
C31H34N404
ESI mass spectrum: m/z"= 525 [M-H"]
(107) 3-Z-[1-(4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-butyl-N-
tert.butoxycarbonyl-aminomethyl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C33H37N305
ESI mass spectrum: m/z = 554 [M-H*]
(108) 3-Z-[1-(4-(N-((N-aminocarbonylmethyl-N-methyl-amino)-
methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(N-aminocarbonylmethyl-N-
methyl-amino)-methylcarbonyl)-N-methyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C29H29NsOs
ESI mass spectrum: m/z = 526 [M-H"]
(109) 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl)-
N-methyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-((N-benzyl-N-methyl-amino)-
methylcarbonyl)-N-methyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C34H32N404
ESI mass spectrum: m/z = 559 [M-H"]

(110) 3-Z- [1- (4-(N-(di-(2-methoxyethyl)-amino-methylcarbonyl)-
N-methyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-(di-(2-methoxyethyl)-amino-methylcarbonyl )-N-methyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C32H36N406 ESI mass spectrum: m/z = 571 [M-H"]
(111) 3-Z-[1-(4-(N-((2-(4-tert.butoxycarbonyl-piperazin-1-yl)-
ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(l-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-((2-(4-tert.butoxycarbonyl-
piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-p-phenylenediamine
Rf value: 0.8 (silica gel, methylene chloride/methanol = 5:1)
C36H41N506
ESI mass spectrum: m/z = 638 [M-H"]
(112) 3-Z- [1- (4- (N- ( (2- (piperidin-1-yl) -ethyl).-carbonyl) -N-
methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-
2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N~((2-(piperidin-1-yl)-
ethyl)-carbonyl)-N-methyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 5:1)
C32H34N404
ESI mass spectrum: m/z = 537 [M-H"]
(113) 3-Z- [1- (4- (N-((2-(N-benzyl-N-methyl-amino)-ethyl)-
carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-((2-(N-benzyl-N-methyl-amino) -ethyl)-carbonyl)-N-methyl-p-phenylenediamine

Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1)
C35H34N404
ESI mass spectrum: m/z = 573 [M-H"J
(114) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-isopropyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-
(dimethylaminomethylcarbonyl)-N-isopropyl-p-phenylenediamine Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C30H32N4O4 ESI mass spectrum: m/z = 511 [M-H~]
(115) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N-
isopropyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(piperidin-1-yl-
methylcarbonyl)-N-isopropyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C33H36N404
ESI mass spectrum: m/z = 551 [M-H"]
(116) 3-Z-[1-(4-(N-((4-tert.butoxycarbonyl-piperazin-1-yl)-
methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-
methylene] - 6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-((4-tert.butoxycarbonyl-
piperazin-1-yl)-methylcarbonyl)-N-isopropyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C37H43N506
ESI mass spectrum: m/z = 652 [M-H"]

(117) 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl) -N-benzyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-((N-benzyl-N-methyl-amino) -methylcarbonyl)-N-benzyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1) C40H36N4O4 ESI mass spectrum: m/z = 635 [M-H"]
(118) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-benzyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and N-(dimethylaminomethyl-
carbonyl)-N-benzyl-p-phenylenediamine
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C34H32N404
ESI mass spectrum: m/z = 559 [M-H"]
(119) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N-benzyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(5-methyl-imidazol-4-yl)-
aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
L.37ri36JN4U4
ESI mass spectrum: m/z = 559 [M-H"]
(120) 3-Z-[1-(4-(l,2,4-triazol-2-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(1,2,4-triazol-l-yl-methyl)-aniline , R£ value: 0.5 (silica gel, methylene chloride/methanol = 10 .-1)

C26H21N503
ESI mass spectrum: m/z = 450 [M-H~]
(121) 3-Z- [1-(4-(1,2,3-triazol-2-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl~2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(1,2,3-triazol~2-yl-
methyl)-aniline
Rr value: 0.5 (silica gel, methylene chloride/methanol = 20:1)
C„H21N503
ESI mass spectrum: m/z = 450 [M-H"]
(122) 3-Z- [1- (4-(1,2,3-triazol-l-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-(1,2,3-triazol-l-yl-methyl) -aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol - 9:1) C26H21N503 ESI mass spectrum: m/z = 450 [M-H~]
(123) 3-Z-[1-(4-((N-aminocarbonylmethyl-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((N-aminocarbonylmethyl-N-
methyl-amino)-methyl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C27H26N404
ESI mass spectrum: m/z = 469 [M-H"]
(124) 3-Z-[1-(4-((di-(2-methoxy-ethyl)-amino)-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((di-(2-methoxy-ethyl)-
amino)-methyl)-aniline

Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C30H33N3O5
ESI mass spectrum: m/z = 514 [M-H"]
(125) 3-Z-[1-(4-(pyrrolidin-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(pyrrolidin-1-yl-methyl)-
aniline ,
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C28H27N303
ESI mass spectrum: m/z = 452 [M-H"]
(126) 3-Z- [1-(4-((di-(2-hydroxy-ethyl)-amino)-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2~indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((di-(2-hydroxy-ethyl)-
amino)-methyl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C28H23N305
ESI mass spectrum: m/z = 486 [M-H"]
(127) 3-Z-[1-(4-((N-ethoxycarbonylmethyl-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((N-ethoxycarbonylmethyl-N-methyl-amino)-methyl)-aniline Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol =
40:1)
C29H29N305
ESI mass spectrum: m/z = 498 [M-H"]
(128) 3-Z-[1-(4-(azetidin-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(azetidin-1-yl-methyl)-
aniline
R£ value: 0.5 (silica gel, methylene chloride/methanol/ammonia
= 9:1:0.5)
C27H2SN303
ESI mass spectrum: m/z *= 438 [M-H~]
(129) 3-Z-[1-(4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)-
anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(N-propyl-N-
tert .butoxycarbonyl-aminomethyl)-aniline
Rf value.- 0.5 (silica gel, methylene chloride/methanol = 9:1)
C32H3SN305
ESI mass spectrum: m/z - 540 [M-H"]
(130) 3-Z-[1-(4((N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-
amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-
2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((N-(2-(2-methoxy-ethoxy)-
ethyl)-N-methyl-amino)-methyl)-aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol = 9:1)
C30H33N3O5
ESI mass spectrum: m/z = 514 [M-H"]
(131) 3-Z- [1- (4- ( (N- (tert.butoxycarbonyl-3-amino-propyl)-N-
methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-methoxy¬
carbonyl -2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6 -
methoxycarbonyl-2-indolinone and 4-(N-(N-tert.butoxycarbonyl-
3-amino-propyl)-N-methyl-aminomethyl)-aniline
R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C33H38N405
ESI mass spectrum: m/z = 571 [M+H+]

(132) 3-Z- [1-(4-( (N-(methylcarbamoyl-methyl)-N-methyl-amino) -
methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((N-(methylcarbamoyl-
methyl)-N-methyl-amino)-methyl)-aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9.-1)
C28H28N404
ESI mass spectrum: m/z *= 483 [M-H"]
(133) 3-Z- [1-(4-((N-(dimethylcarbamoyl-methyl)-N-methyl-
amino) -methyl) -anilino) -1 -phenyl-methylene] -6-methoxycarbonyl-
2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((N-(dimethylcarbamoyl-
methyl)-N-methyl-amino)-methyl)-aniline
Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1)
C29H30N4O4
ESI mass spectrum: m/z = 497 [M-H"]
(134) 3-Z- [1-(4-methyl-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-methyl-aniline
Rf value: 0.4 (silica gel, methylene chloride/methanol = 9:1)
C24H20N2O3
ESI mass spectrum: m/z - 383 [M-H"]
(135) 3-Z- [1-(4-((N-propyl-N-methyl-amino)-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((N-propyl-N-methyl-amino)-
methyl)-aniline
R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C28H29N303

ESI mass spectrum: m/z = 454 [M-H"]
(136) 3-Z-[1-(4-((N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((N-(2-hydroxy-ethyl)-N-
methyl-amino)-methyl)-aniline
Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol =
40:1)
C27H27N304
ESI mass spectrum: m/z = 456 [M-H"]
(137) 3-Z-[1-(4-((N-(2-dimethylamino-ethyl)-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-methoxycarbonyl-2-indolinone and 4-((N-(2-dimethylamino-ethyl) -N-methyl-amino)-methyl)-aniline
Rf value: 0."5 (silica gel, methylene chloride/methanol = 9:1) C29H32N403 ESI mass spectrum: m/z = 483 [M-H"]
(138) 3-Z-[1-(4-((N-(3-dimethylamino-propyl)-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-((N-(3-dimethylamino-
propyl)-N-methyl-amino)-methyl)-aniline aniline
R£ value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C30H34N4O3
ESI mass spectrum: m/z = 497 [M-H"]
(139) 3-Z-[1-(4-(3-oxo-piperazin-l-yl-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

Prepared from l-acetyl-3-(1-ethoxy-l-phenylmethylene)-6-
methoxycarbonyl-2-indolinone and 4-(3-oxo-piperazin-1-yl-
methyl)-aniline aniline
R£ value: 0.46 (silica gel, methylene chloride/methanol = 9:1)
C28H26N404
ESI mass spectrum: m/z = 481 [M-H~]
Example 4
3-Z-[1-(4-carboxy-anilino)-1-phenyl-methylene]-6-ethoxy-
carbonyl-2 -indolinone
485 mg of 3-Z- [1-(4-tert.butoxycarbonyl-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone are dissolved in 15
ml of methylene chloride and 6.0 ml of trifluoroacetic acid
are added. The mixture is stirred for 2 hours at room
temperature. Then the solvent is removed and the residue
recrystallised from ether.
Yield: 375 mg (87 % of theory),
Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1)
C25H20N2O5
Mass spectrum: m/z = 428 [M+]
The following compounds are prepared analogously to Example 4 :
(1) 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-aminomethyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia
= 5:1:0.01)
C24H21N303
ESI mass spectrum: m/z = 398 [M-H"]
(2) 3-Z- [1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone

Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylamino-
methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
R£ value: 0.4 (silica gel, methylene chloride/methanol/ammonia
= 10:1:0.01) C26H2SN303 ESI mass spectrum: m/z = 426 [M-H~]
(3) 3-Z- [1-(4-carboxymethyl-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-tert.butoxycarbonylmethyl-anilino)-1-
phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
Rf value: 0.1 (aluminium oxide, methylene
chloride/ethanol/ammonia = 5:1:0.01)
C26H22N2Os
ESI mass spectrum: m/z = 441 [M-H~]
(4) 3-Z-[1-(4-carboxy-anilino)-1-ethyl-methylene]-6-ethoxy-
carbonyl-2 -indolinone
Prepared from 3-Z-[1-(4-tert.butoxycarbonyl-anilino)-1-ethyl-
methylene]-6-ethoxycarbonyl-2-indolinone
Rf value: 0.1 (aluminium oxide, methylene chloride/ethanol =
20:1)
ESI mass spectrum: m/z = 3 79 [M-H"]
(5) 3-Z- [1-(4-(piperazin-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-(4-tert.butoxycarbonyl-piperazin-l-yl-
methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-
indolinone
Rf value: 0.1 (silica gel, methylene chloride/methanol/ammonia
= 10:1:0.01)
C28H28N403
ESI mass spectrum: m/z = 469 [M+H+]

(6) 3-Z-[1-(4-butylaminomethyl-anilino) -1-phenyl-methylene]-6-
methoxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-(N-butyl-N-tert.butoxycarbonyl-
aminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C28H29N303
ESI mass spectrum: m/z = 454 [M-H~]
(7) 3-Z-[1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
Prepared from 3-Z- [1-(4-(N-tert.butoxycarbonyl-N-ethyl-
aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-
indolinone
R£ value: 0.3 (silica gel, methylene chloride/methanol/ammonia
= 10:1:0.01)
C27H27N303
ESI mass spectrum: m/z = 442 [M+H+]
(8) 3-Z-[1-(4-ethylaminomethyl-anilino) -1-phenyl-methylene]-6-
carbamoyl-2-indolinone
Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylamino-
methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone
R£ value: 0.2 (silica gel, methylene chloride/methanol/ammonia
= 5:1:0.01)
C2SH24N402
ESI mass spectrum: m/z = 411 [M-H"]
(9) 3-Z-[1-(4-(N- (piperazin-1-yl-methylcarbonyl)-N-isopropyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from 3-Z- [1- (4-(N-((4-tert.butoxycarbonyl-piperazin-1-yl) -methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone

Rf value: 0.35 (silica gel, methylene chloride/methanol = 9:1)
C32H35Ns04
ESI mass spectrum: m/z = 552 [M-H~]
(10) 3-Z-[1-(4-(N-((2-(piperazin-1-yl)-ethyl)-carbonyl)-N-
methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-
2-indolinone
Prepared from 3-Z-[1-(4-(N-((2-(4-tert.butoxycarbonyl-
piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-
phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone
R£ value: 0.4 (silica gel, methylene chloride/methanol/ammonia
= 5:1:0.01)
C31H33N504
ESI mass spectrum: m/z = 540 [M+H+]
(11) 3-Z-[1-(4-(N-propyl-aminomethyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl- 2 -indolinone
Prepared from 3-Z-[1-(4-(N-propyl-N-tert.butoxycarbonyl-
aminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Rf value: 0.35 (silica gel, methylene chloride/methanol = 9:1)
C27H27N303
ESI mass spectrum: m/z = 440 [M-H~]
(12) 3-Z-[1-(4-((N-(3-amino-propyl)-N-methyl-amino)-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-((N-(tert.butoxycarbonyl-3-amino-
propyl) -N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Rf value: 0.3 5 (silica gel, methylene chloride/methanol = 9:1)
C2aH30N4O3
ESI mass spectrum: m/z = 471 [M+H+]

Example 5
3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene] -6-
e thoxycarbonyl - 2 - indol inone "
100 mg of 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)-anilino)-
1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone are
dissolved in 20 ml of ethanol, 0.2 ml of IN hydrochloric acid
are added and the mixture is hydrogenated for 70 minutes at
room temperature and 50 psi hydrogen pressure. The reaction
solution is filtered and the filtrate concentrated by rotary
evaporation. The residue is dried in vacuo at 100°C.
Yield: 50 mg (53 % of theory),
Rf value: 0.3 (silica gel, methylene chloride/ethanol/ammonia
=5:1:0.01)
C26H2SN303
ESI mass spectrum: m/z = 426 [M-H"]
The following compounds are prepared analogously to Example 5:
(1) 3-Z-[1-(4-methylaminomethyl-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Prepared from 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
R£ value: 0.2 (silica gel, methylene chloride/methanol/ammonia
= 10:1:0.01)
C2SH23N303
ESI mass spectrum: m/z = 412 [M-H"]
(2) 3-Z^[1-(4-(N-(2-methylamino-ethyl)-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from 3-Z-[1-(4-((2-(N-benzyl-N-methyl-amino)-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

Rf value: 0.3 (silica gel, methylene chloride/methanol/ammonia
= 10:1:0.01)
C27H28N405S
ESI mass spectrum: m/z = 519 [M-H"]
(3) 3-Z- [1-(4-(N-(2-amino-ethyl)-N-methylsulphonyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-(N-cyanomethyl-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia
= 5:1:0.01)
C26H26N4OsS
ESI mass spectrum: m/z = 505 [M-H"]
(4) 3-Z-[1-(4-(N-(3-methylamino-propyl)-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from 3-Z-[1-(4-(N-(3-(N-benzyl-N-methyl-amino)-
propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Rf value: 0.3 (silica gel, methylene chloride/methanol/ammonia
= 5:1:0.01)
C28H30N4O5S
ESI mass spectrum: m/z = 533 [M-H ]
(5) 3-Z-[1-(4-(N-(piperazin-1-yl-methylcarbonyl)-N-methyl-
amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from 3-Z-[1-(4-(N-((4-benzyl-piperazin-l-yl)-
methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Rf value: 0.5 (silica gel, methylene chloride/methanol = 9:1)
C30H31NsO4
ESI mass spectrum: m/z = 524 [M-H"]

(6) 3-Z-[1-(4-(N-(methylamino-methylcarbonyl)-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)-
methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Rf value: 0.3 (silica gel, methylene chloride/methanol = 9:1)
C27H26N404
ESI mass spectrum: m/z = 469 [M-H~]
(7) 3-Z-[1-(4-(N-((2-methylamino-ethyl)-carbonyl)-N-methyl-
amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from 3-Z- [1- (4-(N-((2-(N-benzyl-N-methyl-amino)-
ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
Rf value: 0.3 (silica gel, methylene chloride/methanol/ammonia
= 5:1:0.01)
C2BH28N404
ESI mass spectrum: m/z = 483 [M-H"]
Example 6
3-Z-[1-(4-ureidomethyl-anilino)-1-phenyl-methylene]-6-methoxy-
carbonvl-2 -indolinone
300 mg of 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone are dissolved in 15 ml of methanol and 200 ml of triethylamine are added. Then 4 00 mg of potassium cyanate in 5 ml of water are added. After 2 days of stirring at room temperature the reaction solution is concentrated by rotary evaporation, the residue taken up in methylene chloride and washed once with water and once with saturated sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated by rotary evaporation. The residue is dried in vacuo at 10 0°C.
Yield: 100 mg of (21 % of theory),

Rf value: 0.7 (silica gel, methylene chloride/methanol = 5:1)
C25H22N404
ESI mass spectrum: m/z = 441 [M-H~]
Example 7
3-Z-[1-(4-guanidinomethyl-anilino)-1-phenyl-methylene]-6-
methoxycarbonvl-2 -indolinone
300 mg of 3-Z- [1- (4,-aminomethyl-anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone are dissolved in 5 ml of dimethylformamide and 300 ml of triethylamine are added. Then 700 mg of 3,5-dimethylpyrazol-l-carboxylic acid amidine in 5 ml of dimethylformamide are added. After one day of stirring at room temperature the reaction solution is concentrated by rotary evaporation. The residue is dried at 100°C in vacuo.
Yield: 200 mg (87 % of theory),
Rf value: 0.1 (Reversed phase RP 8, methanol/five percent
saline solution = 6:4)
^25^23^03
Mass spectrum: m/z = 441 [M+]
Example 8
3-Z-[1-(4-acetylaminomethyl-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
100. mg of 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone are dissolved in 5 ml of glacial acetic acid, 0.1 ml of acetic anhydride is added and the mixture is stirred for 10 minutes at room temperature. After this time the reaction solution is poured onto saturated soda solution and extracted four times with methylene chloride. The combined organic phases are washed with saturated saline solution, dried over sodium sulphate and concentrated by rotary evaporation. The residue is dried at 100°C in vacuo.

Yield: 20 mg (23 % of theory),
Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1)
C26H23N304
ESI mass spectrum: m/z = 440 [M-H"]
The following compounds are prepared analogously to Example 8:
(1) 3-Z-[1-(4-(N-methylsulphonyl-aminomethyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl- 2 -indolinone
Prepared from 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone and methanesulphonyl
chloride/triethylamine
Rf value: 0.7 (silica gel, methylene chloride/methanol = 5:1)
ESI mass spectrum: m/z = 476 [M-H"]
(2) 3-Z-[1-(4-(4-benzoyl-piperazin-l-yl-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
Prepared from 3-Z- [1-(4-(piperazin-1-yl-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2-indolinone and benzoyl
chloride
Rf value: 0.7 (silica gel, methylene chloride/methanol = 10:1)
C3SH32N404
ESI mass spectrum: m/z = 571 [M-H"]
(3) 3-Z-[1-(4-((N-(3-acetylamino-propyl)-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-
indolinone
Prepared from 3-Z-[1-(4-((N-(3-amino-propyl)-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-
indolinone
Rf value: 0.3 (silica gel, methylene chloride/methanol = 9:1)
C30H32N4O4
ESI mass spectrum: m/z = 511 [M-H ]

Example 9
3-Z-[l-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene1-6-carboxy-2-indolinone
0.8 g of 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone are dissolved in 30 ml of ethanol, 8.3 ml of IN sodium hydroxide solution are added and the mixture is stirred for 1 hour at 8 0°C. After cooling, it is neutralised with 8.3 ml of IN hydrochloric acid. The precipitate formed is suction filtered, washed with water, ethanol and ether and dried in vacuo at 100°C.
Yield: 0.7 g of (89 % of theory),
RE value: 0.2 (silica gel, methylene chloride/methanol = 5:2)
C28H27N303
Mass spectrum: m/z = 453 [M+]
The following compounds are prepared analogously to Example 9:
(1) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene] -6-carboxy-
2-indolinone
Prepared from 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-
6 -ethoxycarbony1-2-indolinone
Rf value: 0.4 (silica gel, toluene/ethyl acetate = 5:1)
C22H15BrN203
ESI mass spectrum: m/z = 43 5/43 7 [M+H+]
(2) 3-Z-[1-(3-(dimethylaminomethyl)-anilino)-1-phenyl-
methylene]-6-carboxy-2-indolinone
Prepared from 3-Z-[1-(3-(dimethylaminomethyl)-anilino)-
1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
Rf value: 0.7 (Reversed phase RP 8, methanol/five percent
saline solution =4:1)
C25H23N303
ESI mass spectrum: m/z = 414 [M+H+]

(3) 3-Z-[1-(4-(dimethylaminomethyl)-anilino) -1-phenyl-
methylene]- 6-carboxy-2-indolinone
Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-
1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
Rf value: 0.7 (Reversed phase RP 8, methanol/five percent
saline solution =4:1)
C25H23N303
ESI mass spectrum: m/z = 412 [M-H"]
(4) 3-Z-[1-(4- [ (2,6-dimethyl-piperidin-l-yl)-methyl]-anilino)-
1-phenyl-methylene]- 6-carboxy-2-indolinone
Prepared from 3-Z-[1-(4-[ (2,6-dimethyl-piperidin-l-yl)-
methyl] -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-
indolinone
Rf value: 0.6 (Reversed phase RP 8, methanol/five percent
saline solution = 4:1)
C30H31N3O3
ESI mass spectrum: m/z = 482 [M+H+]
(5) 3-Z-[1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-
methylene]- 6-carboxy-2 -indolinone
Prepared from 3-Z- [1-(4-(l-methyl-imidazol-2-yl) -anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Rf value: 0.6 (Reversed phase RP 8, methanol/five percent
saline solution =4:1)
C26H20N4O3
ESI mass spectrum: m/z = 435 [M-H"]
(6) 3-Z-[1-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)-
anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone
Prepared from 3-Z-[1-(4-(N-acetyl-N-
dimethylaminocarbonylmethyl-amino) -anilino) -1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Rf value: 0.3 (silica gel, methylene chloride/methanol = 10:1)
C28H26N405
ESI mass spectrum: m/z = 497 [M-H"]

(7) 3-Z- [1-(4-ethylaminomethyl-anilino)-1-phenyl-methylene]-6-
carboxy-2-indolinone
Prepared from 3-Z-[1-(4-ethylaminomethyl-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
Rf value: 0.6 (Reversed phase RP 8, methanol/five percent
saline solution = 4:1)
C2SH23N303
ESI mass spectrum: m/z = 412 [M-H~]
(8) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -
anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone
Prepared from 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-
methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-
2-indolinone
Rf value: 0.6 (Reversed phase RP 8, methanol/five percent
saline solution = 4:1)
C27H26N404
ESI mass spectrum: m/z = 469 [M-H"]
(9) 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylaminomethyl)-
anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone
Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-ethylamino¬
methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-
indolinone
Rf value: 0.4 (silica gel, methylene chloride/methanol = 10:1)
C30H31N3O5
ESI mass spectrum: m/z = 512 [M-H"]
(10) 3-Z-[1-(4-((N-carboxymethyl-N-methyl-amino)-methyl)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-((N-ethoxycarbonylmethyl-N-methyl-
amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl
-2-indolinone

Rf value: 0.4 (silica gel, methylene chloride/methanol =6:1)
C27H25N305
ESI mass spectrum: m/z = 470 [M-H ]
Example 10
3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-methoxvcarbonyl-2 -indolinone
0.9 g of 3-Z- [1- (4-,"(piperidin-l-yl-methyl) -anilino) -l-phenyl-methylene]-6-carboxy-2-indolinone are suspended in 35 ml of dimethylformamide and 0.4 g of carbonyldiimidazole are added. The mixture is stirred for 14 hours at 80°C. After this time
2 0 ml of methanol are added and the mixture is stirred for
another 3 hours at 50°C. The solvent is removed and the
residue is purified over a silica gel column with methylene
chloride/methanol (3:1) as eluant.
Yield: 0.5 g of (49% of theory),
RE value: 0.5 (aluminium oxide, methylene chloride/methanol =
3 0:1)
C29H29N303
ESI mass spectrum: m/z = 468 [M+H+]
The following compounds are prepared analogously to Example 10:
(1) 3-Z-[1-(4-(piperidin-l-yl-methyl)-anilino)-1-phenyl-
methylene]- 6-benzyloxycarbonyl-2 -indolinone
Prepared from 3-Z- [1-(4-(piperidin-l-yl-methyl)-anilino)-
1-phenyl-methylene]-6-carboxy-2-indolinone and benzyl alcohol
Rf value: 0.6 (aluminium oxide, methylene chloride/methanol =
30:1)
C3SH33N303
Mass spectrum: m/z = 543 [M+]
(2) 3-Z-[1-(4-(piperidin-l-yl-methyl)-anilino)-1-phenyl-
methylene]-6-isopropyloxycarbonyl-2 -indolinone

Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and isopropanol Rf value: 0.4 (aluminium oxide, methylene chloride/isopropanol
= 30:1)
Mass spectrum: m/z = 495 [M+]
(3) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene] -6-propyloxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-
1-phenyl-methylene]-6-carboxy-2-indolinone and n-propanol
Rf value: 0.7 (silica gel, methylene chloride/methanol =" 5:1)
C31H33N303
Mass spectrum: m/z = 495 [M+]
(4) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene] -6-butyloxycarbonyl-2-indolinone
Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-
1-phenyl-methylene]-6-carboxy-2-indolinone and n-butanol
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C32H35N303
Mass spectrum: m/z = 509 [M+]
(5) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-6-carbamoyl-
2 -indolinone
Prepared from 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-
6-carboxy-2-indolinone and ammonia
Rf value: 0.5 (silica gel, methylene chloride/methanol = 10:1)
C22H16BrN203
Mass spectrum: m/z = 432/434 [M-H~]
(6) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene]-6-ethylcarbamoyl-2 -indolinone
Prepared from 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and ethylamine gas Rf value: 0.6 (silica gel, methylene chloride/methanol = 5:1)

C30H32N4O2
Mass spectrum: m/z = 480 [M+]
(7) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-
methylene]-6-[(2-methoxy-ethoxy)-carbonyl]-2-indolinone
Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)~
l-phenyl-methylene]-6-carboxy-2-indolinone and methylglycol
Rf value: 0.8 (silica gel, methylene chloride/methanol = 4:1)
C25H23N303
ESI mass spectrum: m/z = 470 [M-H"]
(8) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl-
methylene]-6-[(2-dimethylamino-ethoxy)-carbonyl]-2-indolinone
Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-
l-phenyl-methylene]-6-carboxy-2-indolinone and
2-dimethylaminoethanol aniline
Rf value: 0.5 (silica gel, methylene chloride/methanol = 5:2)
C29H32N403 •
ESI mass spectrum: m/z = 483 [M-JTJ
(9) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl-
methylene]-6-[(2-N-tert.butoxycarbonyl-amino-ethoxy)-
carbonyl]-2-indolinone
Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl-methylene]-6-carboxy-2-indolinone and 2-N-tert .butoxycarbonyl-amino-ethanol aniline
Rf value: 0.8 (silica gel, methylene chloride/methanol = 5:2) C32H36N405 ESI mass spectrum: m/z = 412 [M-H"]
(10) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl-
methylene]-6-[(2,2,2-trifluoroethoxy)-carbonyl]-2-indolinone

Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-
1-phenyl-methylene]- 6-carboxy-2-indolinone and 2,2,2-
trifluoroethanol aniline
R£ value: 0.5 (silica gel, methylene chloride/methanol = 5:1)
C27H24F3N303
ESI mass spectrum: m/z = 494 [M-H~]
Example 11
3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methvlene]-6-carbamoyl-2-indolinone
0.9 g of 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone, 0.8 g of TBTU and 0.4 g of HOBT are suspended in 25 ml of dimethylformamide and 1.0 ml of triethylamine are added. The mixture is stirred for 15 minutes at room temperature. After this time ammonia gas is introduced at 10-15°C over a period of 15 minutes and the mixture is stirred for 1.5 hours at room temperature. The precipitate formed is suction filtered, washed with water, ethanol and ether and dried at 10 0°C in vacuo.
Yield: 0.6 g (64 % of theory),
Rf value: 0.4 (Reversed phase RP 8, methanol/five percent
saline solution = 6:4)
C28H28N402
ESI mass spectrum: m/z = 453 [M+H+]
The following compounds are prepared analogously to Example 11:
(1) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-dimethylcarbamoyl-2-indolinone Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and dimethylamine hydrochloride/diisopropylethylamine

R£ value: 0.5 (silica gel, methylene chloride/methanol = 5:1)
C30H32N4O2
ESI mass spectrum: m/z = 481 [M+H+]
(2) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene] -6-(N-ethyl-N-methyl-carbamoyl)-2-indolinone
Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-
1-phenyl-methylene]-6-carboxy-2-indolinone and N-ethyl-
N-methyl-amine
Rf value: 0.5 (aluminium oxide, methylene chloride/ethanol =
20:1)
C31H34N402
ESI mass spectrum: m/z = 495 [M+H+]
(3) 3-Z- [1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene] - 6-methylcarbamoyl-2-indolinone
Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-
1-phenyl-methylene]-6-carboxy-2-indolinone and methylamine
hydrochloride/diisopropylethylamine
Rf value: 0.3 (aluminium oxide, methylene chloride/ethanol =
20:1)
C29H30N4O2
ESI mass spectrum: m/z = 467 [M+H+]
(4) 3-Z-[1-(3-(dimethylaminomethyl)-anilino)-1-phenyl-
methylene] -6-methylcarbamoyl-2-indolinone
Prepared from 3-Z-[1-(3-(dimethylaminomethyl)-anilino)-
1-phenyl-methylene]-6-carboxyl-2-indolinone and methylamine
hydrochloride/triethylamine
Rf value: 0.3 (silica gel, methylene chloride/ethanol = 2:1)
C26H26N402
Mass spectrum: m/z = 426 [M+]
(5) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-
methylene] -6-(2-hydroxyethyl-carbamoyl)-2-indolinone

Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-
1-phenyl-methylene]- 6-carboxy-2-indolinone and
ethanolamine/diisopropylethylamine
Rf value: 0.5 (aluminium oxide, methylene chloride/methanol =
20:1)
C30H32N4O3
ESI mass spectrum: m/z = 4 95 [M-H~]
(6) 3-Z- [1- (4- (pipe.ridin-1-yl-methyl) -anilino) -1-phenyl-
methylene]-6-diethylcarbamoyl-2 -indolinone
Prepared from 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-indolinone and diethylamine hydrochloride/diisopropylethylamine R£ value: 0.8 (aluminium oxide, methylene chloride/methanol =
10:1)
C32H36N402
ESI mass spectrum: m/z = 509 [M+H+]
(7) 3-Z-[IT(4-(N-tert.butoxycarbonyl-ethylaminomethyl)-
anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone
Prepared from 3-Z-[1-(4-(N-tert.butoxycarbonyl-
ethylaminomethyl)-anilino)-1-phenyl-methylene]-6-carboxy-2-
indolinone
Rf value: 0.3 (silica gel, toluene/ethyl acetate/ethanol =
4:2:1)
C30H32N4O4
ESI mass spectrum: m/z = 511 [M-H"]
(8) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone
Prepared from 3-Z-[1-(4-(N-dimethylaminomethylcarbohyl-N-
methyl-amino)-anilino)-1-phenyl-methylene]-6-carboxy-2-
indolinone
Rf value: 0.5 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01)

C27H27N503
ESI mass spectrum: m/z = 468 [M-H"]
Example 12
3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
x citric acid
3.25 g of citric acid monohydrate are placed in 50 ml of methanol and 5.0 g of 3-Z-[1-(4-(N-dimethylaminomethyl-carbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone are added at room temperature. The solution formed is evaporated down, the residue is washed with ether and recrystallised from ethyl acetate. Yield: 6.3 g (90 % of theory),
Rf value: 0.6 (silica gel, methylene chloride/methanol/ammonia =5:1:0.01) Melting point: 198°C C28H28N4Os x C6H807
ESI mass spectrum: m/z = 483 [M-H"]
Elemental analysis: calc: C 60.34 H 5.37 N 8.28
found: 59.98 5.25 8.13
The following compound is prepared analogously to Example 12:
(1) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone x methanesulphonic acid
Prepared from 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone and methanesulphonic acid
Rf value: 0.6 (silica gel, methylene chloride/methanol/ammonia = 5:1:0.01) Melting point: 275°C C26H25N303 x CH403S ESI mass spectrum: m/z = 426 [M-H"]

Elemental analysis: calc.: C 61.92 H 5.59 N 8.03 S 6.12
found: 61.43 5.87 7.85 5.39
The following compounds may be prepared analogously to the foregoing Examples:
(1) 3-Z-(1-anilino-1-phenyl-methylene)-6-ethoxycarbonyl-2-indolinone
(2) 3-Z-[1-(4-nitro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(3) 3-Z- [1-(4-fluoro-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone
(4) 3-Z- [1-(4-chloro-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone
(5) 3-Z-[1-(4-iodo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(6) 3-Z- [1-(4-cyano-anilino)-1-phenyl-methylene]-6-ethoxy-carbonyl-2 -indolinone
(7) 3-Z-[1-(4-methoxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(8) 3-Z-[1-(4-ethoxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(9) 3-Z-[1-(4-trifluoromethyl-anilino)-1-phenyl-methylene]-
6-ethoxycarbonyl-2-indolinone
(10) 3-Z-[1-(4-methyl-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone

(11) 3-Z-[1-(4-methylmercapto-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(12) 3-Z-[1-(4-aminomethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(13) 3-Z-[1-(4-(isopropylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(14) 3-Z-[1-(4-(anilinomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(15) 3-Z-[1-(4-(propylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(16) 3-Z-[1-(4-(butylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(17) 3-Z-[1-(4-(isobutylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(18) 3-Z-[1-(4-(cyclohexylaminomethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(19) 3-Z-[1-(4-(benzylaminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(20) 3-Z-[1-(4-((N-ethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(21) 3-Z-[1-(4-((N-methyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(22) 3-Z-[1-(4-((N-isopropyl-N-methyl-amino)-methyl)-anilino) 1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone

(23) 3-Z- [1-(4-((N-ethyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(24) 3-Z- [1-(4-((N-ethyl-N-isopropyl-amino)-methyl)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(25) 3-Z-[1-(4-(dipropylaminomethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(26) 3-Z- [1-(4-(diisopropylaminomethyl)-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone
(27)" 3-Z-[1-(4-((N-benzyl-N-ethyl-amino)-methyl)-anilino)-1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone
(28) 3-Z-[1-(4-(dibenzylaminomethyl)-anilino)-1-phenyl-
methylene]-6-ethoxycarbony1-2 -indolinone
(29) 3-Z- [1-(4-(3,6-dihydro-2H-pyridin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(30) 3-Z- [1-(4-(3,5-dimethyl-piperidin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(31) 3-Z-[1-(4-(azepan-1-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(32) 3-Z- [1-(4-(piperazin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(33) 3-Z- [1-(4-(morpholin-4-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(34) 3-Z- [1-(4-(thiomorpholin-4-yl-methyl)-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone

(35) 3-Z-[1-(4-(l-oxo-thiomorpholin-4-yl-methyl)-anilino)-
1-phenyl-methylene]-6 -ethoxycarbonyl- 2 -indolinone
(36) 3-Z- [1- (4- (1,l-dioxo-thiomorpholin-4-yl-methyl)-anilino)-1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone
(37) 3-Z-[1-(4-(acetylamino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(38) 3-Z-[1-(4-(2-amino-ethyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(39) 3-Z-[1-(4-(2-methylamino-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(40) 3-Z- [1- (4-.(2-ethylamino-ethyl) -anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(41) 3-Z-[1-(4-(2-diethylamino-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(42) 3-Z-[1-(4-(2-piperidin-l-yl-ethyl)-anilino)-1-phenyl-methylene]- 6 -ethoxycarbonyl-2 -indolinone
(43) 3-Z-[1-(4-(2-acetylamino-ethyl)-anilino)-l-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(44) 3-Z-[1-(4-(3-amino-propyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(45) 3-Z-[1-(4-(3-dimethylamino-propyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(46) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(47) 3-Z-[1-(4-(N-methylaminomethylcarbonyl-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl~2-indolinone
(48) 3-Z- [1-(4-(N-ethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(49) 3-Z-11- (4- lE-diethylaminomethylcarbonyl-TSI-methyl-amino) anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(50) 3-Z- [1- (4- (N- (pipejridin-1-yl-methylca-rbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(51) 3-Z-[1-(4-(N-(morpholin-4-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(52) 3-Z- [1-(4-(N-(piperazin-1-yl-methylcarbonyl)-N-methyl-amino]-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl~2-indolinone
(53) 3-Z-[1-(4-(N-(2-amino-ethylcarbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(54) 3-Z-[1-(4-(N-(2-methylamino-ethylcarbonyl)-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(55) 3-Z-[1-(4-(N-(2-diethylamino-ethylcarbonyl)-N-methyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(56) 3-Z-[1-(4-(N-acetyl-N-(2-aminoethyl) -amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(57) .3-Z-[1-(4-(N-acetyl-N-(2-methylamino-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(58) 3-Z-[1-(4-(N-acetyl-N-(2-methylamino-propyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(59) 3-Z-[1-(4-(N-acetyl-N-(2-piperidin-l-yl-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(60) 3-Z-[1-(4-(N-acetyl-N-(aminocarbonylmethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(61) 3-Z-[1-(4-(N-acetyl-N-(dimethylaminocarbonylmethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(62) 3-Z-[1-(4-(N-acetyl-N-(piperidin-1-yl-carbonylmethyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(63) 3-Z-[1-(4-(N-methyl-N-(aminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(64) 3-Z-[1-(4-(N-methyl-N-(methylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(65) 3-Z-[l-(4-(N-methyl-N-(dimethylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(66) 3-Z-[1-(4-(N-methyl-N-(piperidin-1-yl-carbonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(67) 3-Z-[1-(4-(N-(2-aminoethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(68) 3-Z-[1-(4-(N-(2-methylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(69) 3-Z-[1-(4-(N-(2-ethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(70) 3-Z-[1-(4-(N-(2-disthylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(71) 3-Z-[1-(4-(N-(2-pyrrolidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(72) 3-Z-[1-(4-(N-(2-piperidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(73) 3-Z-[1-(4-(N-(2-piperazin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(74) 3-Z-[1-(4-(N-(2-(morpholin-4-yl)-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone

(75) 3-Z-[l-(4-(N-(aminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(76) 3-Z-[1-(4-(N-(methylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone

(77) 3-Z-[1-(4-(N-(ethylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(78) 3-Z-[1-(4-(N-(N-(2-dimethylamino-ethyl)-N-methyl-amino)-carbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]- 6-ethoxycarbonyl-2 -indolinone
(79) 3-Z-[l-(4-(N-(diethylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(80) 3-Z-[1-(4-(N-(pyrrolidin-1-yl-carbonylmethyl)-N-methyl¬
sulphonyl -amino) -anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(81) 3-Z-[1-(4-(N-(piperidin-1-yl-carbonylmethyl)-N-
methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(82) 3-Z-[1-(4-(N-(piperazin-1-yl-carbonylmethyl)-N-
methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(83) 3-Z- [1- (4- (N- ( (morpholin-4-yl)-carbonylmethyl)-N-methyl¬
sulphonyl-amino) -anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(84) 3-Z-[1-(4-(2-dimethylamino-ethoxy)-anilino)-1-phenyl-
methylene] - 6-ethoxycarbonyl-2 -indolinone
(85) 3-Z-[1-(4-(3-dimethylamino-propoxy)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2 -indolinone
(86) 3-Z-[1-(4-(aminocarbonylmethyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone

(87) 3-Z-[1-(4-(2-aminocarbonyl-ethyl)-anilino)-1-phenyl-
methylene]-6-ethoxycarbonyl-2-indolinone
(88) 3-Z-[1-(4-(pyridin-2-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(89) 3-Z-[1-(4-(pyridine-3-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(90) 3-Z-[1-(4-(pyridin-4-yl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(91) 3-Z-[1-(4-(N-acetyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(92) 3-Z-[1-(4-(N-ethylcarbonyl-N-(dimethylaminocarbonyl-methyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(93) 3-Z-[1-(carbamoylmethyl-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(94) 3-Z-[1-(4-dimethylcarbamoylmethyl-anilino)-1-phenyl-methylene] -6 -ethoxycarbonyl-2 -indolinone
(95) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-methylene]-6 -ethoxycarbonyl-2 -indolinone
(96) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-propylidene]-6-ethoxycarbonyl-2 -indolinone
(97) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-butylidene]-6-ethoxycarbonyl-2 -indolinone

(98) 3-Z- [1- (4- (N- (3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-methylene]-6-ethoxycarbonyl-2-indolinone
(99) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-ethylidene]-6-ethoxycarbonyl-2-indolinone

(100) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-propylidene]-6-ethoxycarbonyl-2-indolinone
(101) 3-Z- [1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone
(102) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-methylene]-6-ethoxycarbonyl-2-indolinone
(103) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-propylidene]-6-ethoxycarbonyl-2-indolinone
(104) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone
(105) 3-Z-[1-(4-tetrazol-5-yl-anilino)-methylene]-6-ethoxycarbonyl-2 -indolinone
(106) 3-Z-[1-(4-tetrazol-5-yl-anilino)-ethylidene] -6-ethoxy-carbonyl-2 -indolinone

(107) 3-Z- [1- (4-tetrazol-5-yl--anilino) -propylidene] -6-ethoxy-carbonyl-2 -indolinone
(108) 3-Z-[1-(4-tetrazol-5-yl-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone
(109) 3-Z-[1-(4-carboxy-anilino)-methylene] -6-ethoxycarbonyl-2-indolinone

(110) 3-Z-[1-(4-carboxy-anilino)-propylidene]-6-ethoxycarbonyl-2 -indolinone
(111) 3-Z- [1-(4-carboxy-anilino)-butylidene] -6-ethoxycarbonyl-2-indolinone
(112) 3-Z- [1-(4-(N-(3-dimethylamino-propionyl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-l-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(113) 3-Z- [1-(4-(N-(4-dimethylamino-butyryl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(114) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(2-dimethylamino-ethylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(115) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(3-dimethylamino-propylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(116) 3-Z-[1-(4-((2-hydroxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(117) 3-Z-[1-(4-((2-methoxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(118) 3-Z-[1-(4-((2-dimethylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(119) 3-Z-[1-(4-((3-dimethylamino-propyl)-amino-methyl)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(120) 3-Z-[1-(4-((N-tert.butoxycarbonyl-2-amino-ethyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(121) 3-Z-[1-(4-((N-tert.butoxycarbonyl-3-amino-propyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(122) 3-Z- [1- (4- ( (2.-amino-ethyl) -amino-methyl) -anilino) -1-pheny1-methylene]-6-ethoxyc arbony1-2 -indo1inone
(123) 3-Z-[1-(4-((3-amino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(124) 3-Z-[1-(4-((2-acetylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(125) 3-Z-[1-(4-((3-acetylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(126) 3-Z-[1-(4-((2-methylsulphonylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(127) 3-Z-[1-(4-((3-methylsulphonylamino-propyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(128) 3-Z-[1-(4-(N-(N-tert.butoxycarbonyl-2-amino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(129) 3-Z-[1-(4-(N-(2-amino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(130) 3-Z-[1-(4-(N-(2-acetylamino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(131) 3-Z-[1-(4-(N-(2-methylsulphonylamino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(132) 3-Z-[1-(4-(carboxymethyl-amino-methyl)-anilino)-1-phenyl-methylene-] -6-ethoxycarbonyl-2-indolinone

(133) 3-Z-[1-(4-(ethoxycarbonylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(134) 3-Z-[1-(4-(carbamoylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(135) 3-Z-[1-(4-(dimethylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(136) 3-Z-[1-(4-(methylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(137) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-amino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(138) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-nitro-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(13 9) 3-Z-[l-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-acetylamino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone

(140) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methylsulphonylamino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(141) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-cyano-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(142) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-hydroxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(143) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methoxy-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2 -indolinone

(144) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-ethoxycarbonyl~anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(145) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-carboxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(146) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-carbamoyl-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(147) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-chloro-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(148) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-fluoro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(149) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-bromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(150) 3-Z- [1- (4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(151) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(152) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3,5-dibromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(153) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3,5-dichloro-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(154) 3-Z- [1-(4-(dimethylaminomethyl)-3-amino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(155) 3-Z- [1-(4-(dimethylaminomethyl)-3-nitro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone

(156) 3-Z- [1-(4-(dimethylaminomethyl)-3-acetylamino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(157) 3-Z-[1-(4-(dimethylaminomethyl)-3-(methylsulphonylamino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(158) 3-Z- [1-(4-(dimethylaminomethyl)-3-cyano-anilino)-1-
phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(159) 3-Z-[1-(4-(dimethylaminomethyl)-3-hydroxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(160) 3-Z-[1-(4-(dimethylaminomethyl)-3-methoxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(161) 3-Z-[1-(4-(dimethylaminomethyl)-3-(ethoxycarbonyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(162) 3-Z-[1-(4-(dimethylaminomethyl)-3-carboxy-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(163) 3-Z-[1-(4-(dimethylaminomethyl)-3-carbamoyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(164) 3-Z-[1-(4-(dimethylaminomethyl)-3-chloro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(165) 3-Z-[1-(4-(dimethylaminomethyl)-3-fluoro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(166) 3-Z-[1-(4-(dimethylaminomethyl)-3-bromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(167) 3-Z-[1-(4-(dimethylaminomethyl)-3-methyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(168) 3-Z-[1-(4-(dimethylaminomethyl)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(169) 3-Z-[1-(4-(dimethylaminomethyl)-3,5-dibromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(170) 3-Z-[1-(4-(dimethylaminomethyl)-3,5-dichloro-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(171) 3-Z- [1-(4-(N-((4-methyl-piperazin-l-yl)-methylcarbonyl) -N-methyl-amino) -anilino) -1-phenyl-methylene] - 6-ethoxycarbonyl-2-indolinone
(172) 3-Z-[1-(4-(N-(imidazo~l-yl-methylcarbonyl)-N-methyl-amino) -anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(173) 3-Z- [1- (4- (N-„"(phthalimido-2-yl-methylcarbonyl) -N-methyl-amino) -anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone

(174) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(175) 3-Z- [1-(4-(N-acetylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(176) 3-Z-[1-(4-(N-methylsulphonylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(177) 3-Z-[1-(4-(N-((N-(2-methoxyethyl) -N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6 -ethoxycarbony1-2 -indolinone

(178) 3-Z- [1-(4- (N-((N-(2-dimethylaminoethyl)-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(179) 3-Z-[1-(4-(N-((di-(2-hydroxyethyl)-amino)-methylcarbonyl)-N-methyl-amino)-anilino) -1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(180) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino) -methylene] -6-ethoxycarbonyl-2-indolinone

(181) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-ethylidene]-6-ethoxycarbonyl-2-indolinone
(182) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-propylidene]-6-ethoxycarbonyl-2-indolinone
(183) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-butylidene]-6-ethoxycarbonyl-2-indolinone
(184) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-methylene]-6-ethoxycarbonyl-2 -indolinone
(185) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-ethylidene]-6-ethoxycarbonyl-2-indolinone
(186) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-propylidene]-6-ethoxycarbonyl-2 -indolinone
(187) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-butylidene]-6-ethoxycarbonyl-2 -indolinone
(188) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(189) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(190) 3-Z-[1-(4-((imidazolidin-2/4-dion-5-ylidene)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(191) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(192) 3-Z-[1-(4-(N-tert.butoxycarbonyl-aminomethyl)-anilino) 1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(193) 3-Z-[1-(4-(2-oxo-pyrrolidin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(194) 3-Z-[1-(4-(N-aminocarbonylmethyl-N-methylsulphonyl-
amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(195) 3-Z-[1-(4-(N-cyanomethyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(196) 3-Z-[1-(4-(2-(imidazol-4-yl)-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(197) 3-Z-[1-(4-((2-(N-benzyl-N-methyl-amino)-ethyl)-N-
methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(198) 3-Z-[1-(4-cyclohexylamino-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(199) 3-Z-[1-(4-(imidazol-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(200) 3-Z-[1-(4-(imidazol-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(201) 3-Z-[1-(N-methyl-piperidine-4-yl-amino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(202) 3-Z-[1-(4-(imidazol-4-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(203) 3-Z-[1-(4-((4-hydroxy-piperidin-l-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(204) 3-Z- [1- (4- ( (4-methoxy-piperidin-l-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(205) 3-Z-[1-(4-benzyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(206) 3-Z- [1-(4-(N-(3-trifluoroacetylamino-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(207) 3-Z- [1-(4-(4-tert.butoxycarbonyl-piperazin-1-yl-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(208) 3-Z-[1-(4-(1-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(209) 3-Z- [1-(4-(l-methyl-imidazol-2-yl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(210) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-3-amino-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(211) 3-Z-[1-(4-((3-(N-benzyl-N-methyl-amino)-propyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(212) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl) -N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(213) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-butyryl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone

(214) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-isobutyryl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(215) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzoyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(216) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-amino-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(217) 3-Z-[l-(4-(4-hydroxymethyl-piperidin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(218) 3-Z-[1-(4-(2-(4-hydroxy-piperidin-l-yl)-ethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(219) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-propylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(220) 3-Z- [1- (4- (N- (2-dimethylamino-ethyl)-N-butylsulphonyl-
amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-
2-indolinone
(221) 3-Z- [1- (4- (N- (2-dimethylamino-ethyl)-N-phenylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(222) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-benzylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(223) 3-Z-[1-(4-((imidazolidin-2,4-dion-5-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(224) 3-Z-[1-(4-((3-hydroxy-pyrrolidin-l-yl)-methyl)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(225) 3-Z-[1-(4-(cyclohexylyl-methyl)-anilino) -1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(226) 3-Z-[1-(4-(cyclohexyl-carbonyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(227) 3-Z-[1-(4-diethylaminomethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(228) 3-Z-[1-(4-(N-(n-hexyl)-N-methyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(229) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(furan-2-carbonyl)-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2 -indolinone
(230) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl) -N-(2-methoxy-benzoyl)-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(231) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(pyridine-3-
carbonyl)-amino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(232) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-(phenyl-acetyl)-
amino)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(233) 3-Z-[1-(4-(imidazol-2-yl)-anilino)-l-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(234) 3-Z-[1-(4-(l-ethyl-imidazol-2-yl)-anilino)-l-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone

(235) 3-Z-[1-(4-(l-benzyl-imidazol-2-yl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(236) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-isopropylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(237) 3-Z- [1- (4- (N-,"( (4-benzyl-piperazin-l-yl) -methylcarbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(238) 3-Z-[1-(4-(N-(pyrrolidin-1-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(239) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-3-bromo-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(240) 3-Z-[1-(4-(5-methyl-imidazol-4-yl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(241) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(242) 3-Z-[1-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-benzyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(243) 3-Z-[1-(4-(N-butyl-N-tert.butoxycarbonyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(244) 3-Z-[1-(4-(N-((N-aminocarbonylmethyl-N-methyl-amino)-
methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-
6-ethoxycarbonyl-2 -indolinone
(245) 3-Z-[1-(4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(246) 3-Z- [1- (4- (N-,"(di- (2 - me thoxy ethyl) -amino-methylcarbonyl) -N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(247) 3-Z-[1-(4-(N-((2-(4-tert.butoxycarbonyl-piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6 -ethoxycarbonyl-2 -indolinone
(248) 3-Z-[1-(4-(N-((2-(piperidin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(249) 3-Z-[1-(4-(N-((2-(N-benzyl-N-methyl-amino)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(250) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-isopropyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(251) 3-Z-[1-(4-(N-(piperidin-1-yl-methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(252) 3-Z-[1-(4-(N-((4-tert.butoxycarbonyl-piperazin-1-yl)-methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone

(253) 3-Z- [1- (4-(N-((N-benzyl-N-methyl-amino)-methylcarbonyl) N-benzyl-amino) -anilino) -1-phenyl-methylene] -6-ethoxycarbonyl 2-indolinone
(254) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-benzyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(255) 3-Z- [1- (4- (N-,"(piperidin-l-yl-methylcarbonyl) -N-benzyl-amino) -anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(256) 3-Z-[l-(4-(l,2,4-triazol-2-yl-methyl)-anilino)-1-phenyl-methylene]-6 -ethoxycarbony1-2 -indolinone
(257) 3-Z- [1-(4-(l,2,3-triazol-2-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(258) 3-Z- [1-(4-(1,2,3-triazol-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(259) 3-Z- [1- (4-( (N-aminocarbonylmethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone

(260) 3-Z-[1-(4-((di-(2-methoxy-ethyl)-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(261) 3-Z-[1-(4-((di-(2-hydroxy-ethyl)-amino)-methyl)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(262) 3-Z-[1-(4-((N-ethoxycarbonylmethyl-N-methyl-amino) -methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone

(263) 3-Z- [1- (4-(azetidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(264) 3-Z-[1-(4-(N-propyl-N-tert.butoxycarbonyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(265) 3-Z-[1-(4-((N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(266) 3-Z- [1-(4- ( (N-(tert.butoxycarbonyl-3-amino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-
ethoxycarbonyl-2 -indolinone
(267) 3-Z-[1-(4-((N-(methylcarbamoyl-methyl)-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(268) 3-Z-[1-(4-((N-(dimethylcarbamoyl-methyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(269) 3-Z-[1-(4-((N-propyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(270) 3-Z-[1-(4-((N-(2-dimethylamino-ethyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(271) 3-Z-[1-(4-((N-(3-dimethylamino-propyl)-N-methyl-amino)-
methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-
2-indolinone
(272) 3-Z-[1-(4-((N-(2-methoxy-ethyl)-N-methyl-amino)-methyl)-
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(273) 3-Z- [1-(4-((N-(2-hydroxy-ethyl)-N-methyl-amino)-methyl) -
anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(274) 3-Z-[1-(4-((N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-2-indolinone
(275) 3-Z- [1- (4- (3-oxo-piperazin-l-yl-methyl)-anilino)-1-phenyl-methylene] -6,-ethoxycarbonyl-2-indolinone
(276) 3-Z- [1-(4-(N-(piperazin-1-yl-methylcarbonyl)-N-isopropyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(277) 3-Z- [1- (4-(N-((2-(piperazin-1-yl)-ethyl)-carbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(278) 3-Z- [1- (4- ( (N-(3-amino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(279) 3-Z-[1-(4-(N-(3-methylamino-propyl) -N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-ethoxycarbonyl-
2-indolinone
(280) 3-Z-[1-(4-Ureidomethyl-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2 -indolinone
(281) 3-Z-[1-(4-guanidinomethyl-anilino)-1-phenyl-methylene] -6 -ethoxycarbonyl-2-indolinone
(282) 3-Z-[1-(4-(N-methylsulphonyl-aminomethyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(283) 3-Z-[1-(4-(4-benzoyl-piperazin-l-yl-methyl)-anilino) -1-
phenyl-methylene]-6-ethoxycarbonyl-2-indolinone

(284) 3-Z-[1-(4-((N-(3-acetylamino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(285) 3-Z-[1-(4-((N-(3-methylsulphonylamino-propyl)-N-methyl-amino) -methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(286) 3-Z-[1-(4-((N-carboxymethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone
(287)3-Z-(1-anilino-l-phenyl-methylene)-6-methoxycarbonyl-2-indolinone
(288) 3-Z-[1-(4-nitro-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone
(289) 3-Z- [1-(4-fluoro-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2-indolinone
(290) 3-Z- [1-(4-chloro-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2-indolinone
(291) 3-Z-[1-(4-bromo-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2-indolinone
(292) 3-Z- [1-(4-iodo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(293) 3-Z-[1-(4-cyano-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone
(294) 3-Z-[1-(4-carboxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(295) 3-Z-[1-(4-methoxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(296) 3-Z- [1-(4-ethoxy-anilino)-1-phenyl-methylene]-6-methoxy-carbonyl-2 -indolinone

(297) 3-Z- [1-(4-trifluoromethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(298) 3-Z- [1-(4-methylmercapto-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(299) 3-Z- [1-(4-(isopropylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone
(300) 3-Z-[1-(4-(anilinomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(301) 3-Z- [1-(4-(isobutylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(302) 3-Z-[1-(4-(cyclohexylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone

(303) 3-Z- [1-(4-(benzylaminomethyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(304) 3-Z-[1-(4-((N-methyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(305) 3-Z- [1-(4-((N-isopropyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(306) 3-Z-[1-(4-((N-ethyl-N-propyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(307) 3-Z- [1-(4-((N-ethyl-N-isopropyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(308)"3-Z- [1- (4-(dipropylaminomethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(309) 3-Z- [1-(4-(diisopropylaminomethyl)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(310) 3-Z-[1-(4-((N-benzyl-N-ethyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(311) 3-Z-[1-(4-(dibenzylaminomethyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone
(312) 3-Z-[1-(4-(3,6-dihydro-2H-pyridin-l-yl-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(313) 3-Z-[1-(4-(3,5-dimethyl-piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(314) 3-Z-[1-(4-(azepan-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(315) 3-Z- [1- (4- (2-amino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(316) 3-Z- [1- (4-(2-methylamino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(317) 3-Z- [1-(4- (2-ethylamino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(318) 3-Z-[1-(4-(2-dimethylamino-ethyl)-anilino)-1-phenyl-methylene]- 6 -methoxycarbonyl-2 -indolinone

(319) 3-Z-[1-(4-(2-diethylamino-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(320) 3-Z- [1- (4-(2-piperidin-l-yl-ethyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(321) 3-Z-[1-(4-(2-acetylamino-ethyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone

(322) 3-Z-[1-(4-(3-amino-propyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(323) 3-Z- [1-(4-(3-dimethylamino-propyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(324) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(325) 3-Z-[1-(4-(N-ethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(326) 3-Z-[1-(4-(N-diethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(327) 3-Z-[1-(4-(N-dipropylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(328) 3-Z-[1-(4-(N-((N-ethyl-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
(329) 3-Z- [1-(4-(N-((N-ethyl-N-propyl-amino)-methylcarbonyl)-
N-methyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2-indolinone

(330) 3-Z-[1-(4-(N-((N-methyl-N-propyl-amino)-methylcarbonyl)-
N-methyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl- 2 -indolinone
(331) 3-Z- [1- (4- (N-"dimethylaminomethylcarbonyl-N-ethyl-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(332) 3-Z- [1- (4- (N-dirnethylaminomethylcarbonyl-N-propyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(333) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-butyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(334) 3-Z-[l-(4-(N-(2-amino-ethylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(335) 3-Z-[1-(4-(N-(2-diethylamino-ethylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(336) 3-Z-[1-(4-(N-acetyl-N-(2-aminoethyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(337) 3-Z-[1-(4-(N-acetyl-N-(2-methylamino-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(338) 3-Z-[1-(4-(N-acetyl-N-(3-methylamino-propyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(339) 3-Z-[1-(4-(N-acetyl-N-(2-piperidin-l-yl-ethyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(340) 3-Z-[1-(4-(N-acetyl-N-(aminocarbonylmethyl)-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(341) 3-Z-[1-(4-(N-acetyl-N-(piperidin-1-yl-carbonylmethyl)-
amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-
indolinone
(342) 3-Z-[1-(4-(N-methyl-N-(aminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(343) 3-Z-[1-(4-(N-methyl-N-(methylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(344) 3-Z-[1-(4-(N-methyl-N-(dimethylaminocarbonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(345) 3-Z-[1-(4-(N-methyl-N-(piperidin-1-yl-carbonyl)-amino) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(346) 3-Z- [1-(4-(N-(2-ethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(347) 3-Z- [1-(4-(N-(2-diethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(348) 3-Z-[1-(4-(N-(2-pyrrolidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(349) 3-Z- [1- (4-(N-(2-piperidin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(350) 3-Z- [1- (4-(N-(2-piperazin-l-yl-ethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone

(351) 3-Z- [1- (4- (N- (2- (4-morphc-1 in-1-yl) -ethyl) -N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2 -indolinone
(352) 3-Z-[1-(4-(N-(ethylaminocarbonylmethyl)-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(353) 3-Z- [1- (4- (N-,"(diethylaminocarbonylmethyl) -N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(354) 3-Z-[1-(4-(N-(pyrrolidin-1-yl-carbonylmethyl)-N-methyl-sulphonyl-amino)-anilino)-1-phenyl-methylene] -6-
methoxycarbonyl-2 -indolinone
(355) 3-Z-[1-(4-(N-(piperidin-1-yl-carbonylmethyl)-N-methyl-
sulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
(356) 3-Z-[1-(4-(N-(piperazin-1-yl-carbonylmethyl)-N-methyl-
sulphonyl-amino)-anilino)-1-phenyl-methylene] -6-
methoxycarbonyl-2 -indolinone
(357) 3-Z-[1-(4-(N-((morpholin-4-yl)-carbonylmethyl)-N-methyl-
sulphonyl-amino)-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2-indolinone
(358) 3-Z-[1-(4-(2-dimethylamino-ethoxy)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2 -indolinone
(359) 3-Z-[1-(4-(3-dimethylamino-propoxy)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(360) 3-Z-[1-(4-(aminocarbonylmethyl)-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2-indolinone

(361) 3-Z- [1-(4-(2-aminocarbonyl-ethyl)-anilino)-1-phenyl-
methylene]-6-methoxycarbonyl-2-indolinone
(362) 3-Z- [1-(4-(pyridin-2-yl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(363) 3-Z-[1-(4-(pyridine-3-yl)-anilino)-1-phenyl-methylene]-6 -methoxycarbonyl-2,- indolinone
(364) 3-Z- [1-(4((N-phenethyl-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(365) 3-Z- [1-(4-(N-acetyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone
(366) 3-Z- [1-(4-(N-ethylcarbonyl-N-(dimethylaminocarbonyl-methyl)-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(367) 3-Z- [1-(4-(N-methyl-N-methylsulphonyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -iridolinone
(368) 3-Z- [1-(4-carboxymethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(369) 3-Z- [1-(4-carbamoylmethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(370) 3-Z- [1-(4-dimethylcarbamoylmethyl-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(371) 3-Z-[1-(4-tetrazol-5-yl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(372) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-methylene]-
6-methoxycarbonyl-2 -indolinone
(373) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-ethylidene]-
6-methoxycarbonyl-2 -indolinone
(374) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-propylidene]-6-methoxycarbonyl-2-indolinone
(375) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-butylidene]-6-methoxycarbonyl-2 -indolinone
(376) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-methylene]-6-methoxycarbonyl-2-indolinone
(377) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-ethylidene]-6-methoxycarbonyl-2-indolinone
(378) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-propylidene]-6-methoxycarbonyl-2-indolinone
(379) 3-Z-[1-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-butylidene]-6-methoxycarbonyl-2-indolinone
(380) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-methylene]-6-methoxycarbonyl-2-indolinone
(381) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-ethylidene]-6-methoxycarbonyl-2-indolinone
(382) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-propylidene]-6-methoxycarbonyl-2-indolinone
(383) 3-Z-[1-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-anilino)-butylidene]-6-methoxycarbonyl-2-indolinone

(384) 3-Z- [1-(4-tetrazol-5-yl-anilino)-methylene]-6-methoxy¬carbonyl - 2 -indolinone
(385) 3-Z- [1-(4-tetrazol-5-yl-anilino)-ethylidene]-6-methoxy¬carbonyl -2 -indolinone

(386) 3-Z- [1-(4-tetrazol-5-yl-anilino)-propylidene]-6-methoxy¬carbonyl -2 -indolinone
(387) 3-Z-[1-(4-tetrazol-5-yl-anilino)-butylidene]-6-methoxy¬carbonyl -2 -indolinone
(388) 3-Z-[1-(4-carboxy-anilino)-methylene] -6-methoxycarbonyl -2-indolinone
(389) 3-Z-[1-(4-carboxy-anilino)-ethylidene] -6-methoxycarbonyl-2 -indolinone
(390) 3-Z-[1-(4-carboxy-anilino)-propylidene]-6-methoxy¬carbonyl - 2 - indolinone
(391) 3-Z-[1-(4-carboxy-anilino)-butylidene]-6-methoxycarbonyl-2 -indolinone
(392) 3-Z-[1-(4-(N-benzyl-N-methyl-aminomethyl)-anilino)-1-
methyl-methylene]-6-methoxycarbonyl-2 -indolinone
(3 93) 3-Z-[l-(4-(2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone
(394) 3-Z- [1-(4-((benzo(1,3)dioxol-5-yl-methyl)-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone

(395) 3-Z-[1-(4-(N-phenethyl-N-methyl-aminomethyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone
(396) 3-Z-[1-(4-(N-(3,4-dimethoxy-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone
(397) 3-Z-[1-(4-(N-(4-Chloro-benzyl)-N-methyl-amino-methyl)-anilino)-l-methyl-m£thylene]-6-methoxycarbonyl-2-indolinone
(398) 3-Z-[1-(4-(N-(4-methylbenzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone
(399) 3-Z-[1-(4-(N-(4-fluoro-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone
(400) 3-Z-[1-(4-(N-(4-bromo-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-methoxycarbonyl-2-indolinone
(401) 3-Z-[1-(4-(N-(3-dimethylamino-propionyl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(402) 3-Z-[1-(4-(N-(4-dimethylamino-butyryl)-N-dimethylaminocarbonylmethyl-amino)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(403) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(2-dimethylamino-ethylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(404) 3-Z-[1-(4-(N-dimethylaminocarbonylmethyl-N-(3-dimethylamino-propylsulphonyl)-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(405) 3-Z-[1-(4-((2-hydroxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(406) 3-Z- [1-(4-((2-methoxy-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(407) 3-Z-[1-(4-((2-dimethylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(408) 3-Z-[1-(4-((3-dimethylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(409) 3-Z-[1-(4-((N-tert.butoxycarbonyl-2-amino-ethyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(410) 3-Z-[1-(4-((N-tert.butoxycarbonyl-3-amino-propyl)-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indol.inone
(411) 3-Z-[1-(4-((2-amino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(412) 3-Z-[1-(4-((3-amino-propyl)-amino-methyl)-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(413) 3-Z-[1-(4-((2-acetylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(414) 3-Z- [1-(4-((3-acetylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(415) 3-Z-[1-(4-((2-methylsulphonylamino-ethyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(416) 3-Z- [1-(4-((3-methylsulphonylamino-propyl)-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(417) 3-Z- [1-(4-(N-(N-tert.butoxycarbonyl-2-amino-ethyl)-N-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(418) 3-Z- [1- (4- (N-,(2-amino-ethyl) -N-methyl-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(419) 3-Z-[1-(4-(N-(2-acetylamino-ethyl)-N-methyl-amino-methyl) -anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(420) 3-Z- [1-(4-(N-(2-methylsulphonylamino-ethyl)-N-methyl-amino-methyl) -anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(421) 3-Z- [1-(4-(carboxymethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(422) 3-Z-[1-(4-(ethoxycarbonylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(423) 3-Z-[1-(4-(carbamoylmethyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(424) 3-Z-[1-(4-(dimethylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(425) 3-Z-[1-(4-(methylcarbamoyl-methyl-amino-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(426) 3-2- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-amino-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(427) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-nitro-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(428) 3-Z-[1-(4-(N-plmethylaminomethylcarbonyl-N-methyl-amino)-3-acetylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(429) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methylsulphonylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(430) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-cyano-anilino)-l-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(431) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-hydroxy-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
(432) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methoxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(433) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-ethoxycarbonyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(434) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-
amino)-3-carboxy-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone

(435) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-carbamoyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(436) 3-2-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-chloro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(437) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-fluoro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(438) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-bromo-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(439) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-methyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(44 0) 3-Z-[l-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-methoxycarbony1-2 -indolinone
(441) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-
amino)-3,5-dibromo-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
(442) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-
amino)-3,5-dichloro-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2 -indolinone
(443) 3-Z- [1- (4- (dimethylaminomethyll.-3-amino-anilino) -1-
phenyl-methylene]-6-methoxycarbony1-2 -indolinone

(444) 3-Z-[1-(4-(dimethylaminomethyl)-3-nitro-anilino)-1-
phenyl-methylene]- 6-methoxycarbonyl-2-indolinone
(445) 3-Z-[1-(4-(dimethylaminomethyl)-3-acetylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(446) 3-Z-[1-(4-(dimethylaminomethyl)-3-methylsulphonylamino-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(447) 3-Z-[1-(4-(dimethylaminomethyl)-3-cyano-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(448) 3-Z-[1-(4-(dimethylaminomethyl)-3-hydroxy-anilino)-1-pheny1-methylene]-6-methoxycarbonyl-2-indolinone
(449) 3-Z-[1-(4-(dimethylaminomethyl)-3-methoxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(450) 3-Z-[1-(4-(dimethylaminomethyl)-3-ethoxycarbonyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(451) 3-Z-[l-(4-(dimethylaminomethyl)-3-carboxy-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(452) 3-Z-[1-(4-(dimethylaminomethyl)-3-carbamoyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(453) 3-Z-[1-(4-(dimethylaminomethyl)-3-chloro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(454) 3-Z-[1-(4-(dimethylaminomethyl)-3-fluoro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(455) 3-Z-[1-(4-(dimethylaminomethyl)-3-bromo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl- 2-indolinone

(456) 3-Z-[1-(4-(dimethylaminomethyl)-3-methyl-anilino)-1-
phenyl-methylene]-6-methoxycarbonyl- 2-indolinone
(457) 3-Z-[1-(4-(dimethylaminomethyl)-3-trifluoromethyl-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(458) 3-Z-[1-(4-dimethylaminomethyl-3,5-dibromo-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(459) 3-Z-[1-(4-(dimethylaminomethyl) -3 , 5-dichloro-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone

(460) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene] -6-[(2-hydroxy-ethoxy)-carbonyl] -2-indolinone
(461) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene] -6- [ (ethoxycarbonyl-methoxy) -carbonyl] -2-indolinone
(462) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-1-phenyl-methylene] -6-[(carboxy-methoxy)-carbonyl]-2-indolinone
(463) 3-Z-[1-(4-(dimethylaminomethyl) -anilino)-1-phenyl-methylene] -6-[(carbamoyl-methoxy)-carbonyl] -2-indolinone

(464) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-[(2-hydroxy-ethoxy) -carbonyl]-2-indolinone
(465) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(ethoxycarbonyl-methoxy) -carbonyl]-2-indolinone
(466) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino) -1-phenyl-methylene] -6- [ (carboxy-methoxy) -carbonyl]-2-indolinone

(467) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(carbamoyl-methoxy)-carbonyl]" - 2 - indolinone
(468) 3-Z- [1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2-methoxy-ethoxy)-carbonyl]-2-indolinone
(469) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2-dimethylamino-ethoxy)-carbonyl]-2-indolinone
(470) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-
amino)-anilino)-1-phenyl-methylene]-6-[(2-(N-
tert.butoxycarbonyl-amino)-ethoxy)-carbonyl]-2-indolinone
(471) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2-amino-ethoxy)-carbonyl]-2-indolinone
(472) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-[(2,2,2-trifluoroethoxy)-carbonyl]-2-indolinone
(473) 3-Z-[1-(4-(N-((4-methyl-piperazin-l-yl)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(474) 3-Z-[1-(4-(N-(imidazo-1-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(475) 3-Z- [1-(4-(N-(phthalimido-2-yl-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

(476) 3-Z-[1-(4-(N-aminomethylcarbonyl-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(477) 3-Z-[1-(4-(N-acetylaminomethylcarbonyl-N-methyl-amino)-
anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(478) 3-Z-[1-(4-(N-methylsulphonylaminomethylcarbonyl-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 - i ndo 1 i none „"
(479) 3-Z-[1-(4-(N-((N-(2-methoxyethyl)-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(480) 3-Z-[1-(4-(N-((N-(2-dimethylaminoethyl)-N-methyl-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-
6-methoxycarbonyl-2 -indolinone
(481) 3-Z-[1-(4-(N-((di-(2-hydroxyethyl)-amino)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(482) 3-Z-[1-(4-tert.butoxycarbonylmethyl-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2 -indolinone
(483) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-methylene]-6-methoxycarbonyl-2-indolinone
(484) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-ethylidene]-6-methoxycarbonyl-2-indolinone
(485) 3-Z-[1-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-propylidene]-6-methoxycarbonyl-2-indolinone
(486) 3-Z-[l-(4-(N-dimethylaminomethylcarbonyl-N-methyl-amino) -anilino)-butylidene]-6-methoxycarbonyl-2-indolinone

(487) 3-Z-[1-(4-(dimethylaminomethyl)-anilino)-methylene]-6-methoxycarbonyl-2-indolinone
(488) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-ethylidene]-6-methoxycarbonyl- 2 -indolinone
(489) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-propylidene]-6-methoxycarbonyl-2 -indolinone
(490) 3-Z- [1-(4-(dimethylaminomethyl)-anilino)-butylidene]-6-methoxycarbonyl-2 -indolinone
(491) 3-Z- [1-(4-tert.butyloxycarbonyl-anilino)-1-phenyl-methylene]- 6-methoxycarbonyl-2 -indolinone
(492) 3-Z- [1-(4-(N-(2-dimethylamino-ethyl)-N-methyl-amino)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone

(493) 3-Z- [1- (4-(N-(3-dimethylamino-propyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone
(494) 3-Z- [1-(4-(N-methyl-acetylamino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(495) 3-Z- [1-(4-(imidazol-4-yl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2 -indolinone
(496) 3-Z- [1-(4-((N-(dioxolan-2-yl-methyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-
2-indolinone
(497) 3-Z- [1-(4-(N-benzyl-N-methyl-amino-methyl)-anilino)-1-
methyl-methylene]-6-carbamoyl-2-indolinone

(498) 3-Z-[l-(4-(2,3,4,5-tetrahydro-benzo(d)azepin-3-yl-methyl) -anilino) -1-methyl-methylene] -6-carbamoyl-2-indolinone
(499) 3-Z-[1-(4-((benzo(1,3)dioxol-5-yl-methyl)-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-carbamoyl~2-indolinone
(500) 3-Z-[1-(4-(N-phenethyl-N-methyl-amino-methyl)-anilino)-
1-methyl-methylene]- 6-carbamoyl-2 -indolinone
l
(501) 3-Z-[1-(4-(N-(3,4-dimethoxy-benzyl)-N-methyl-amino-
methyl)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone
(502) 3-Z-[1-(4-(N-(4-Chloro-benzyl)-N-methyl-amino-methyl)-
anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone
(503) 3-Z-[1-(4-(N-(4-methyl-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone
(504) 3-Z-[1-(4-(N-(4-fluoro-benzyl)-N-methyl-amino-methyl)-anilino)-1-methyl-methylene]-6-carbamoyl-2-indolinone
(505) 3-Z-[1-(4-(N-(4-bromo-benzyl)-N-methyl-amino-methyl)-anilino) -1-methyl-methylene]-6-carbamoyl-2-indolinone
(506) 3-Z- [1- (4-( (N- (2-methoxy-ethyl)-N-methyl-amino)-methyl)-anilino) -1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone
(507) 3-Z-[1-(4-(dimethylaminomethyl)-anilino) -1-phenyl-methylene]-6- [ (2-amino-ethoxy)-carbonyl]-2-indolinone
(508) 3-Z-[1-(4-((N-(3-methylsulfonylamino-propyl)-N-methyl-amino)-methyl)-anilino)-1-phenyl-methylene] -6-methoxycarbonyl-2-indolinone

Example 13
Dry ampoule containing 75 mg of active substance per 10 ml
Composition:
Active substance 75.0 mg
Mannitol 50.0 mg
water for injections ad 10.0 ml
Preparation:
Active substance and mannitol are dissolved in water. After packaging the solution is freeze-dried. To produce the solution ready for use, the product is dissolved in water for injections.
Example 14
Dry ampoule containing 35 mg of active substance per 2 ml
Composition:
Active substance 35.0 mg
Mannitol 100.0 mg
water for injections ad 2.0 ml
Preparation:
Active substance and mannitol are dissolved in water. After
packaging, the solution is freeze-dried.
To produce the solution ready for use, the product is dissolved in water for injections.

Example 15
Tablet containing 50 mg of active substance
Composition:
(1) Active substance 50.0 mg
(2) Lactose 98.0 mg
(3) Maize starch 50.0 mg
(4) Polyvinylpyrrolidone 15.0 mg
(5) Magnesium stearate 2 . 0 mg
215.0 mg
Preparation:
(1), (2) and (3) are mixed together and granulated with an aqueous solution of (4). (5) is added to the dried granulated material. From this mixture tablets are pressed, biplanar, faceted on both sides and with a dividing notch on one side. Diameter of the tablets: 9 mm.
Example 16
Tablet containing 350 mg of active substance
Composition:
(1) Active substance 350.0 mg
(2) Lactose 136.0 mg
(3) Maize starch 80.0 mg
(4) Polyvinylpyrrolidone 30.0 mg
(5) Magnesium stearate 4.0 mg
600.0 mg
Preparation:
(1), (2) and (3) are mixed together and granulated with an aqueous solution of (4). (5) is added to the dried granulated material. From this mixture tablets are pressed, biplanar, faceted on both sides and with a dividing notch on one side. Diameter of the tablets: 12 mm.
Example 17
Capsules containing 50 mg of active substance Composition:
(1) Active substance 50.0 mg
(2) Dried maize starch 58.0 mg
(3) Powdered lactose 50.0 mg
(4) Magnesium stearate 2.0 mg
160.0 mg
Preparation:
(1) is triturated with (3). This trituration is added to the mixture of (2) and (4) with vigorous mixing.
This powder mixture is packed into size 3 hard gelatine capsules in a capsule filling machine.
Example 18
Capsules containing 350 mg of active substance

Composition:
(1) Active substance 350.0 mg
(2) Dried maize starch 46.0 mg
(3) Powdered lactose 3 0.0 mg
(4) Magnesium stearate 4.0 mg
4 3 0.0 mg
Preparation:
(1) is triturated with (3). This trituration is added to the mixture of (2) and (4) with vigorous mixing.
This powder mixture is packed into size 0 hard gelatine capsules in a capsule filling machine.
Example 19
Suppositories containing 100 mg of active substance
1 suppository contains:
Active substance 100.0 mg
Polyethyleneglycol (M.W. 1500) 600.0 mg Polyethyleneglycol (M.W. 6000) 460.0 mg Polyethylenesorbitan monostearate 840.0 mg
2,000.0 mg
Preparation:
The polyethyleneglycol is melted together with polyethylene sorbitan monostearate. At 40°C the ground active substance is homogeneously dispersed in the melt. It is cooled to 38°C and poured into slightly chilled suppository moulds.

We claim:
1. Indolinones of general formula I

(I),

wherein
X denotes an oxygen atom,
R1 denotes a hydrogen atom,
R2 denotes a carboxy group, a straight-chain or branched C1-4-alk-
oxycarbonyl group,
a straight-chain or branched C1-3-alkoxy-carbonyl group, which is
terminally substituted in the alkyl moiety by a phenyl group,
a straight-chain or branched C2-3-alkoxy-carbonyl group which is
terminally substituted in the alkyl moiety by a C1-3-alkoxy—or
di-(C1-3-alkyl)-amino group,
an aminocarbonyl or methylaminocarbonyl group, an
ethylaminocarbonyl group optionally substituted in the 2 position of
the ethyl group by a hydroxy group or, if R4 does not denote an
aminosulphonyl-phenyl or N-(C1-5-alkyl)-C1-3-alkylaminocarbonyl-
phenyl group, it may also denote a di-(C1-2-alkyl)-aminocarbonyl
group,
R3 denotes a C1-4-alkyl group or a phenyl group which may be
substituted by a fluorine, chlorine or bromine atom, by a
trifluoromethyl, C1-3-alkyl, hydroxy or C1-3-alkoxy group,
R4 denotes a C5-6-cycloalkyl group,

wherein the methylene group in position 4 of the cyclohexyl group may
be substituted by an amino group or replaced by a -N(C1-3-alkyl)
group,
a phenyl group, a phenyl group disubstituted by C1-3-alkyl, C1-3-alkoxy
or nitro groups, wherein the substituents may be identical or different,
or
a phenyl group substituted by the group R6, which may additionally be substituted by a chlorine or bromine atom or by an amino or nitro group, wherein
R6 denotes a fluorine, chlorine or bromine atom,
a C1-3-alkyl, C1-3-alkoxy, nitro, or amino or C5-6-cycloalkyl group,
an imidazolyl or tetrazolyl group bound via a carbon atom, wherein the
abovementioned heteroaromatic groups in the carbon skeleton may be
substituted by a C1-3-alkyl group or a hydrogen atom bound to a
nitrogen atom may be replaced by a C1-3-alkyl or phenyl-C1-3-alkyl
group,
the group of formula

a carboxy, C1-4-alkoxycarbonyl or C5-7-cycloalkyl-carbonyl group,
a 5 or 6-membered cycloalkyleneimino group, wherein
the methylene group in position 4 of the piperidino group may be
replaced by an -NH group,
an unbranched C1-3-alkyl group terminally substituted by the group R7,
wherein
R7 denotes a C5-7-cycloalkyl group,
wherein in a 5 or 6-membered cycloalkyl group a -(CH2)2 group may be
replaced by a -CO-NH group, a -(CH2)3 group may be replaced by an -
NH-CO-NH- or a -(CH2)4 group may be replaced by an -NH-CO-NH-CO

group, whilst in each case a hydrogen atom bound to a nitrogen atom
may be replaced by a C1-3-alkyl group,
a phenyl or pyridinyl group or a pyrrolyl, imidazolyl or triazolyl group
bound via a carbon or nitrogen atom, wherein the abovementioned
heteroaromatic groups in the carbon skeleton may be substituted by a
C1-3-alkyl group,
a hydroxy group,
an amino, C1-6-alkylamino, di-(C1-6-alkyl)-amino, henyl-C1-3-alkylamino
or N-(C1-3-alkyl)-phenyl-C1-3-alkylamino group,
a co-hydroxy-C2-3-alkyl-amino, di-(to-hydroxy-C2-3-alkyl)-amino or
di-(co-(C1-3-alkoxy)-C2-3-alkyl)-amino group,
a C1-3-alkylcarbonylamino-C2-3-alkyl-N-(C1-3-alkyl)-aniino group,
a C1-3-alkylsulphonylamino group,
a N-(C1-3-alkyl)-hydroxycarbonyl-C1-3-alkyl-amino group,
a guanidino group wherein a hydrogen atom may be replaced by a
C1-3-alkyl group,
a group of formula
-N(R8)-CO-(CH2)n -R9 (II), wherein R8 denotes a hydrogen atom or a C1-3-alkyl group,
n denotes one of the numbers 0 or 1 and
R9 denotes an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino or C1-3-alkoxy group, a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an -NH, -N(C1-3-alkyl) or -N(C1-3-alkyl-carbonyl) group, or, if n denotes one of the numbers 1, 2 or 3, R9 may also denote a hydrogen atom,
a group of formula
-N(R10)-(CH2)m-(CO)0-Rn (III),
wherein
R10 denotes a C1-3-alkyl group,
m denotes one of the numbers 1, 2 or 3,

o denotes the number 1 or, if m is one of the numbers 2 or 3, o may
also denote the number 0 and
R11 denotes an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino,
C1-4-alkoxy or methoxy-C1-3-alkoxy group or a 5- or 6-membered
cycloalkyleneimino group, wherein the methylene group in position 4
of the piperidino group may be replaced by an -NH, -N(C1-3-alkyl) or
-N(C1-3-alkyl-carbonyl) group,
an azetidino, pyrrolidino, piperidino, 2,6-dimethyl-piperidino—or
azepino group, wherein
the methylene group in position 3 of the pyrrolidino group may be
substituted by a hydroxy group,
the methylene group in position 4 of the piperidino group may be
substituted by a hydroxy or hydroxy-C1-3-alkyl group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl,
sulphonyl, -N(C1-3-alkyl) or -N(benzoyl) group,
wherein a methylene group linked to an imino-nitrogen atom of the
pyrrolidino or piperazino group may be replaced by a carbonyl group,
or Re denotes a straight-chain C1-3-alkyl group which is terminally
substituted by a carboxy or C1-3-alkoxy-carbonyl group, a group of
formula
-N(R12)-CO-(CH2)p-R13 (IV),
wherein
R12 denotes a C1-3-alkyl or phenyl-C1-3-alkyl group,
p denotes one of the numbers 1 or 2 and
R13 denotes C1-4-alkylamino, di-(C1-4-alkyl)-amino, N-(C1-3-alkyl)-benzylamino, di-(2-methoxy-ethyl)-amino, or aminocarbonyl-methyl-N-(methyl)-amino group,
a pyrrolyl, pyrazolyl or imidazolyl group bound via a nitrogen atom and
optionally substituted by a C1-3-alkyl group,
a pyrrolidino, piperidino, morpholino or a piperazino group optionally
substituted in the 4 position by a C1-3-alkyl, phenyl-C1-3-alkyl or
C1-4-alkoxycarbonyl group or, if p denotes the number 1 or 2, it may
also denote a hydrogen atom, a group of formula-N(R14)-(CH2)q-(CO)r-R15 (V),
wherein
R14 denotes a hydrogen atom, a C1-4-alkyl, phenylcarbonyl,
phenyl-C1-3-alkylcarbonyl, furyl-carbonyl, pyridinyl-carbonyl,
C1-4-alkylsulphonyl, phenylsulphonyl or phenyl-C1-3-alkylsulphonyl group,
q denotes one of the numbers 1, 2 or 3,
r denotes the number 1 or, if q is one of the numbers 2 or 3, it may also denote the number 0 and
R15 denotes an amino, C1-4-alkylamino, di-(C1-4-alkyl)-amino, or N-(Ci-4-alkyl)-benzylamino group, or a group of formula
-N(R16)-S02-R17 (VI),
wherein
R16 denotes a C1-3-alkyl group optionally terminally substituted by a
cyano, trifluoromethyl-carbonylamino group and
R17 denotes a C1-3-alkyl group,
wherein all the single-bonded phenyl groups contained in the groups mentioned under Re may be substituted by a methoxy group and
R5 denotes a hydrogen atom,
wherein a hydrogen atom bound to a nitrogen atom in the
abovementioned groups may be replaced by an acetyl or
tert.butoxycarbonyl group,
the carboxy groups contained in the abovementioned groups may also
be present in the form of the tert.butoxycarbonyl precursor group,
the tautomers, the diastereomers, the enantiomers, the mixtures such
as herein described and the salts such as herein described.
2. Indolinones of general formula I as claimed in claim 1, wherein
X denotes an oxygen atom,
R1 and R5 each denote a hydrogen atom,
R2 denotes a methoxycarbonyl, ethoxycarbonyl or aminocarbonyl
group,
R3 denotes a phenyl group and

R4 denotes a phenyl group monosubstituted by the group Re, wherein
Re denotes an N-methyl-imidazol-2-yl group,
an unbranched C1-3-alkyl group which is terminally substituted by a
C1-4-alkylamino, di-(C1-4-alkyl)-amino, piperidino or
2,6-dimethyl-piperidino group, a group of formula
-N(R12)-CO-(CH2)p-R13 (IV),
wherein
R12 denotes a C1-3-alkyl group,
p denotes one of the numbers 1 or 2 and
R13 denotes a di-(C1-3-alkyl) -amino group, or a group of formula
-N(R14)-(CH2)q-(CO)r-R15 (V),
wherein
R14 denotes a C1-3-alkyl-carbonyl or C1-3-alkylsulphonyl group, q denotes one of the numbers 1, 2 or 3,
r denotes the number 1 or, if q is one of the numbers 2 or 3, r may
also denote the number 0 and
R15 denotes a di-(C1-3-alkyl)-amino group, the tautomers, the
diastereomers, the enantiomers, the mixtures such as herein
described and the salts such as herein described.
3. The following substituted indolinones of general formula I as claimed in claim 1:
(a) 3-Z-[l-(4-(piperidin-l-yl-methyl)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl- 2 -indolinone,
(b) 3-Z-[(l-(4-(piperidin-l-yl-methyl)-anilino)-l-phenyl-methylene]-6-carbamoyl-2-indolinone,
(c) 3-Z-[l-(4-(piperidin-l-yl-methyl)-anilino)-l-phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(d) 3-Z- [ 1 - (4- (dimethylaminomethyl) -anilino)-1 -phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(e) 3-Z-[l-(4-((2,6-dimethyl-piperidin- l-yl)-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,

(f) 3-Z-[l-(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(g) 3-Z-[l-(4-(N-(3-dimethylamino-propyl)-N-acetyl-amino)-anilino)-l-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(h) 3-Z-[ 1 -(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-
anilino)-1 -phenyl-methylene]-6-ethoxycarbonyl-2-indolinone,
(i) 3-Z-[l-(4-(dimethylaminomethyl)-anilino)-l-phenyl-methylene]-
6-methoxycarbonyl-2-indolinone,
(j) 3-Z-[l-(4-(N-acetyl-N-dimethylaminocarbonylmethyl-amino)-
anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(k) 3-Z-[l-(4-ethylaminomethyl-anilino)-l-phenyl-methylene]-6-
methoxycarbonyl- 2 -indolinone,
(1) 3-Z-[l-(4-(l-methyl-imidazol-2-yl)-anilino)-l-phenyl-methylene]-
6-met±io3tycarbonyl-2 -indolinone,
(m) 3-Z-[ 1 -(4-(N-dimethylaminomethylcarbonyl-N-methyl-aniino)-
anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone>
(n) 3-Z-[l-(4-(N-(2-dimethylamino-ethyl)-N-methylsulphonyl-amino)-
anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(o) 3-Z-[ l-(4-(N-(3-dimethylamino-propyl)-N-methylsulphonyl-ami-
no)-anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(p) 3-Z-[ 1 -(4-(N-dimethylaminocarbonylmethyl-N-methylsulphonyl-
amino)-anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(q) 3-Z-[ l-(4-(N-((2-dimethylamino-ethyl)-carbonyl)-N-methyl-
amino)-anilino)-1 -phenyl-methylene]-6-methoxycarbonyl-2-indolinone,
(r) 3-Z-[ 1 -(4-(N-(2-dimethylamino-ethyl)-N-acetyl-amino)-anilino)-1 -
phenyl-methylene]-6-methoxycarbonyl-2-indolinone and
(s) 3-Z-[ l-(4-methylaminomethyl-anilino)-1-phenyl-methylene]-6-
methoxycarbonyl-2-indolinone,
4. Process for preparing the compounds as claimed in claims 1 to
3, wherein
a) a compound of general formula

wherein
X and R3 are defined as in claims 1 to 3,
R2 has the meanings given for R2 in claims 1 to 3,
Ris denotes a hydrogen atom or a protecting group for the nitrogen
atom of the lactam group, wherein one of the groups R2 and R18 may
also denote a bond to a solid phase optionally formed via a spacer and
the other one of the groups R2 and R18 has the abovementioned
meanings, and Z1 denotes a halogen atom, a hydroxy, alkoxy or aryl-
alkoxy group, is reacted with an amine of general formula

wherein
R4 and R5 are defined as in claims 1 to 3, and subsequently, if
required, any protecting group used for the nitrogen atom of the
lactam group is cleaved or a compound thus obtained is cleaved from
a solid phase, or
b) in order to prepare a compound of general formula I wherein
R2 has the meanings given in claims 1 to 3, with the exception of the
carboxy group, a compound of general formula

wherein
R1 and R3 to R5 are defined as in claims 1 to 3, or a reactive derivative
thereof, is reacted with a compound of general formula
H - R19 (X), wherein
R19 denotes a C1-6-alkanol, a C4-7-cycloalkanol or an aromatic alcohol, a C1-6-alkanol which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C1-3-alkoxy-carbonyl, aminocarbonyl, C1-3-alkylamino-carbonyl or di-(C1-3-alkyl)-aminocarbonyl group, a C2-6-alkanol which is terminally substituted in the alkyl moiety by a chlorine atom or a hydroxy, C1-3-alkoxy, amino, C1-3-alkylamino or di-(C1-3-alkyl)-amino group,
an amino or methylamino group, an ethylamino group optionally substituted in the 2 position of the ethyl group by a hydroxy or C1-3-alkoxy group or a di-(C1-2-alkyl)-amino group, or
c) in order to prepare a compound of general formula I, wherein R4
denotes a C1-4-alkyl group substituted by the group R7, wherein
R7 denotes an amino, C1-7-alkylamino, di-(C1-7-alkyl)-amino,
phenylamino, N-phenyl-C1-3-alkyl-amino, phenyl-C1-3-alkylamino,
N-(C1-3-alkyl)-phenyl-C1-3-alkylamino or di-(phenyl-C1-3-alkyl)-amino
group,
a co-hydroxy-C2-3-alkyl-amino, N-(C1-3-alkyl)-co-hydroxy-C2-3-alkyl-amino,
di-(co-hydroxy-C2-3-alkyl)-amino, di-(co-(C1-3-alkoxy)-C2-3-alkyl)-amino or
N-(dioxolan-2-yl)-C1-3-alkyl-amino group,
a C1-3-alkylcarbonylamino-C2-3-alkyl-amino or
C1-3-alkylcarbonylamino-C2-3-alkyl-N-(C1-3-alkyl)-amino group,

a C1-3-alkylsulphonylamino, N-(C1-3-alkyl)-C1-3-alkylsulphonylamino,
C1-3-alkylsulphonylamino-C2-3-alkyl-amino or
C1-3-alkylsulphonylamino-C2-3-alkyl-N-(C1-3-alkyl)-amino group, a group of formula
-N(R10)-(CH2)m-(CO)o-R11 (III),
wherein
R10 denotes a hydrogen atom, a C1-3-alkyl group, a C1-3-alkylcarbonyl,
arylcarbonyl, phenyl-C1-3-alkylcarbonyl, C1-3-alkylsulphonyl,
arylsulphonyl or phenyl-C1-3-alkylsulphonyl group,
m denotes one of the numbers 1, 2, 3 or 4,
o denotes the number 1 and
R11 denotes an amino, C1-4-alkylamino, di-(C1-4-alkyl)-amino,
phenylamino, N-(C1-4-alkyl)-phenylamino, benzylamino,
N-(C1-4-alkyl)-benzylamino, C1-4-alkoxy or C1-3-alkoxy-C1-3-alkoxy
group, a di-(C1-4-alkyl)-amino-C1-3-alkylamino group optionally
substituted in the 1 position by a C1-3-alkyl group, or a 4- to 7-
membered cycloalkyleneimino group, wherein the cycloalkylene moiety
may be fused to a phenyl ring or in each case the methylene group in
the 4 position of a 6- or 7-membered cycloalkyleneimino group may be
replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl,
-NH, -N(C1-3-alkyl), -N(phenyl), -N(C1-3-alkyl-carbonyl) or -N(benzoyl)
group,
a C4-7-cycloalkylamino, C4-7-cycloalkyl-C1-3-alkylamino or
C4-7-cycloalkenylamino group wherein position 1 of the ring is not
involved in the double bond and wherein the abovementioned groups
may each additionally be substituted at the amino-nitrogen atom by a
C5-7-cycloalkyl, C2-4-alkenyl or C1-4-alkyl group,
or a 4- to 7-membered cycloalkyleneimino group, wherein
the cycloalkylene moiety may be fused to a phenyl group or to an
oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group
optionally substituted by a fluorine, chlorine, bromine or iodine atom,
by a nitro, C1-3-alkyl, C1-3-alkoxy or amino group, and/or
one or two hydrogen atoms may each be replaced by a C1-3-alkyl,
C5-7-cycloalkyl or phenyl group and/or the methylene group in the 3 position of a 5-membered
cycloalkyleneimino group may be substituted by a hydroxy, hy-
droxy-C1-3-alkyl, C1-3-alkoxy or C1-3-alkoxy-C1-3-alkyl group,
in each case the methylene group in the 3 or 4 position of a 6- or 7-
membered cycloalkyleneimino group may be substituted by a hydroxy,
hydroxy-C1-3-alkyl, C1-3-alkoxy, C1-3-alkoxy-C1-3-alkyl,
C1-4-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl,
di-(C1-3-alkyl)-aminocarbonyl, phenyl-C1-3-alkylamino or N-(C1-3-alkyl)-phenyl-C1-3-alkylamino group or
may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, -NH, -N(C1-3-alkyl-), -N(phenyl), -N(phenyl-C1-3-alkyl-), -N(C1-3-alkyl-carbonyl-), -N(C1-3-alkoxy-carbonyl-), -N(benzoyl-) or -N(phenyl-C1-3-alkyl-carbonyl-) group,
wherein a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5- to 7-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group,
a compound of general formula

wherein
R3, R5 and X are defined as in claims 1 to 3,
R2 has the meanings given for R2 in claims 1 to 3,
also denote a bond to a solid phase optionally formed via a spacer and the other one of the groups R2 and R18 has the abovementioned meanings, A denotes a Ci-4-alkyl group and Z2 denotes a leaving group, is reacted with an amine of general formula
H—R7, (XII),
wherein
R7 has the meanings given for R7 hereinbefore, and subsequently, if
necessary, any protecting group used for the nitrogen atom of the
lactam group is cleaved, or a compound thus obtained is cleaved from
a solid phase, and
subsequently, if desired, a compound of general formula I thus
obtained which contains an alkoxycarbonyl group is converted by
hydrolysis into a corresponding carboxy compound, or
a compound of general formula I thus obtained which contains an
amino or alkylamino group is converted by reductive alkylation into a
corresponding alkylamino or dialkylamino compound, or
a compound of general formula I thus obtained which contains an
amino or alkylamino group is converted by acylation or sulphonation
into a corresponding acyl or sulphonyl compound or
a compound of general formula I thus obtained which contains a
carboxy group is converted by esterification or amidation into a
corresponding ester or aminocarbonyl compound or
a compound of general formula I thus obtained which contains a
cycloalkyleneimino group wherein a methylene group is replaced by a
sulphur atom is converted by oxidation into a corresponding sulphinyl
or sulphonyl compound, or a compound of general formula I thus obtained which contains a nitro
group is converted by reduction into a corresponding amino
compound, or a compound of general formula I thus obtained wherein R4 denotes a
phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group is converted, by reaction with a corresponding cyanate, isocyanate or carbamoyl halide, into a corresponding ureacompound of general formula I
Ri8 denotes a hydrogen atom or a protecting group for the nitrogen
atom of the lactam group, wherein one of the groups R2 and R18 may

a compound of general formula I thus obtained wherein R4 denotes a phenyl group substituted by an amino, alkylamino, aminoalkyl or N-alkyl-amino group is converted, by reaction with a corresponding compound which transfers the amidino group or by reaction with a corresponding nitrile, into a corresponding guanidino compound of general formula I, or if necessary any protecting group used during the reactions to protect reactive groups is cleaved or subsequently, if desired, a compound of general formula I thus obtained is resolved into the stereoisomers thereof or
a compound of general formula I thus obtained is converted into the salts thereof, particularly, for pharmaceutical use, into the physiologically acceptable salts thereof with an inorganic or organic acid or base.
Dated this 26th day of April, 2007.
(SHUKADEV KHURAIJAM)
OF REMFRY & SAGAR
ATTORNEY )FOR THE APPLICANTS

Documents:

in-pct-2002-362-mum-cancelled pages(25-06-2007).pdf

in-pct-2002-362-mum-claims(granted)-(25-06-2007).doc

in-pct-2002-362-mum-claims(granted)-(25-06-2007).pdf

in-pct-2002-362-mum-correspondence(23-08-2007).pdf

in-pct-2002-362-mum-correspondence(ipo)-(23-08-2006).pdf

in-pct-2002-362-mum-form 1(26-03-2002).pdf

in-pct-2002-362-mum-form 13(05-05-2003).pdf

in-pct-2002-362-mum-form 18(30-11-2005).pdf

in-pct-2002-362-mum-form 1a(25-06-2007).pdf

in-pct-2002-362-mum-form 2(granted)-(25-06-2007).doc

in-pct-2002-362-mum-form 2(granted)-(25-06-2007).pdf

in-pct-2002-362-mum-form 3(25-06-2007).pdf

in-pct-2002-362-mum-form 3(26-03-2002).pdf

in-pct-2002-362-mum-form 5(25-06-2007).pdf

in-pct-2002-362-mum-form-pct-ipea-409(26-03-2002).pdf

in-pct-2002-362-mum-form-pct-isa-210(26-03-2002).pdf

in-pct-2002-362-mum-petition under rule 137(25-06-2007).pdf

in-pct-2002-362-mum-petition under rule 138(25-06-2008).pdf

in-pct-2002-362-mum-power of authority(25-06-2007).pdf

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Patent Number

210415

Indian Patent Application Number

IN/PCT/2002/00362/MUM

PG Journal Number

44/2007

Publication Date

02-Nov-2007

Grant Date

03-Oct-2007

Date of Filing

26-Mar-2002

Name of Patentee

BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG.

Applicant Address

55216 INGELHEIM AM RHEIN

Inventors:

#	Inventor's Name	Inventor's Address
1	ARMIN HECKEL	GESCHWISTER-SCHOLL-STRASSE 71, D-88400 BIBERCH
2	GERALD JURGEN ROTH	AKAZEIENWEG 47, D-88400 BIBETRCH
3	RAINER WALTER	PROBSTRASSE 3, D-88400 BIBERCH
4	JACOBUS VAN MEEL	WEISSES KREUZ GASSE 61, A-2340 MODLING
5	NORBERT REDEMANN	KOHLESRAIN 48, D-88400 BIBERCH
6	ULRIKE TONTSCH-GRUNT	OETKERWEG 23, A-2500 BADEN
7	WALTER SPEVAK	LEOBERNDORFERSTRASSE 36, A-2105 OBERROHRBACH
8	FRANK HILBERG	PILGRAMGASSE 18/22, A-1050 WIEN

PCT International Classification Number

C07D209/34

PCT International Application Number

PCT/EP00/09867

PCT International Filing date

2000-10-09

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	19949208.5	1999-10-13	Germany