Title of Invention

NEW IMIDAZOTRIAZINONES

Abstract

Imidazotriazinones of the following general formula (I) (I), in which R1 represents (Ci-C6)-alkyl, R2 represents (C3-C8)-cycloalkyl or (Ci-Ci2)-alkyl, R3 represents (Ci-CeJ-alkyl, R4 represents a radical of the formula -NH-CO-NR17 R18, in which R17 and R18 are identical or different and represent hydrogen or (Ci-Ce)-alkyl which is optionally substituted by hydroxyl or by a radical of f formulae or -NR19R20 in which R19 and R20 are identical or different and represent hydrogen, phenyL or (C1-C6)-alkyl or R17 and R18 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R21 represents hydrogen or (Ci -C6)-alkyl, a represents either 1 or 2 R22 represents hydroxyl or (Ci-C6)-alkyl which is optionally substituted by hydroxyl, or RW and/or R18 represent (C6-C12)-aryl which is optionally substituted by halogen trifluoroethyl or by -SCF3 or R17 represents hydrogen and R18 represents a radical of the formula -SO2-R23, in which R23 represents (C1-C6)-alkyl or (C6-C12)-aryl which is optionally substituted by halogen or represents a radical of the formulae and its tautomers and its pharmaceutically acceptable salts, hydrates and prodrugs.

Full Text

FROM 2 THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS RULES, 2003 COMPLETE SPECIFICATION [See Section 10; rule 13] "NEW IMIDAZOTRIAZINONES BAYER AKTIENGESELLSCHAFT, a body corporate organized under the laws of Germany, D-51368 Leverkusen, Germany, The following specification particularly describes the invention and the manner in which it is to be performed: The present invention relates to novel imidazotriazinones, to processes for their preparation and to their use as medicaments, in particular as inhibitors of cGMP-metabolizing phosphodiesterases. The published specificiation DE-OS 2811780 describes imidazotriazines as broncho-dilators having spasmolytic activity and inhibitory activity against phosphodiesterases which metabolize cyclic adenosine monophosphate (cAMP-PDEs. nomenclature according to Beavo: PDE III and PDE IV). An inhibitory action against phosphodiesterases which metabolize cyclic guanosine monophosphate [cGMP-PDEs, nomeclature according to Beavo and Reifsnyder (Trends in Pharmacol. Sci. 11, 150-155, 1990) PDE I, PDE II and PDEV] has not been described. Furthermore, FR-22 13 058, CH-59 46 71. DE-22 55 172: DE-23 64 076 and EP-000 9384 describe imidazotriazinones which do not have a substituted aryl radical in the 2 position and are likewise said to be bronchodilatators having cAMP-PDE-inhibitory action. WO-A-99/24433 likewise describes imidazotriazinones as inhibitors of cGMP-meta-bolizing phosphodiesterase; however, these compounds, by definition, all have a sulfonamide group in the phenyl ring, in the position para to the alkoxy group. An increase in the cGMP concentration can lead to beneficial antiaggregatory, antithrombotic, antiprolific. antivasospastic. vasodilative, natriuretic and diuretic effects. It can influence the short- or long-term modulation of vascular and cardiac inotropy, of the pulse and of cardiac conduction (.1. C. Stoclet, T. Keravis, N. Komas and C. Kugnier. Exp. Opin. Invest. Drugs (1995). 4 (]]), 1081-1100). Inhibition of cGMP-PDEs can also enhance erections. Accordingly, such compounds are suitable for treating erectile dysfunction. The present invention accordingly relates to novel imidazotriazinones of the general formula (I) in which 5 R1 represents (C]-C6)-alkyl. R2 represents (C3-C8)-cycloalkyl or (C]-C]2)-alkyl. R3 represents (CpC^-alkyl, R4 represents a radical of the formulae in which R5. R6 and R7 are identical or different and represent vinyl or (C]-C6)-alkyl which is optionally substituted up to 3 times by identical or different substituents from the group consisting of trifluoromethyl, halogen. (CrC6)-alkoxy or by radicals of the formulae in which 5 R8 represents hydrogen or (CpC^-alkyl. or R5. R6 and/or R7 represents (C^-C^)"31"}7} which is optionally substituted up to 3 10 times by identical or different substituents from the group consisting of halogen, trifluoromethyl. nitro. cyano. carboxyl. (Cj-C^-alkyl and (Cj-C^)- „n or 15 R5 represents quinolyl or a 5- to 6-membered aromatic or saturated heterocycle having up to 3 beieroatoms from the group consisting of S. N and O. which heterocycle may optionally be substituted up to 3 times, in the case of an N function also via this N function, by identical or different substituents from 20 the group consisting of halogen and (C]-C6)-alkyl or R5 represents a radical of the formulae 25 in which 5 R9 and R10 are identical or different and represent hydrogen. (Cj-Cg^alkyl or phenyl. or ] 0 R4 represents carboxyl or represents a radical of the formulae 15 in which R1] and R12 are identical or different and represent hydrogen or (C1-C4)-alkyl. 20 R] ? represents (C ] -C6)-alkyl. R'4 represents (C]-C6)-alkyl which is optionally substituted up to 3 times by identical or differem substituents from the group consisting of 25 hydroxy!, phenyl or by a radical of the formula -NR15R16. in which R15 and R16 are identical or different and represent hydrogen, phenyl or (C]- 5 C4)-alkyl which for its part may be substituted by phenyl, or R4 represents a radical of the formula -NH-CO-NR] 7R] 8. 10 in which R]7 and R'8 are identical or different and represent hydrogen or (Cj-C^-alkyl which is optionally substituted by hydroxyl or by a radical of the formulae in which 20 R19 and R20 are identical or different and represent hydrogen, phenyl or (Cj- C6)-alkyl or R17 and R]8 together with the nitrogen atom to which they are attached form 25 a heterocyclic ring of the formulae in which R2 ] represents hydrogen or (C ] -C^-alkyl, 5 , a represents either 1 or 2. R22 represents hydroxyl or (CrC6)-alkyl which is optionally substituted by hydroxyl, 10 or R'7 and/or R18 represent (C6-C]2)-aryl which is optionally substituted by halogen, trifluoroethyl or by -SCF3 15 or R'7 represents hydrogen and R18 represents a radical of the formula -SO^-R2^, 20 in which R23 represents (C]-C6)-alky] or (C6-C]2)-aryl which is optionally substituted by halogen. 25 or represents a radical of the formulae or R4 represents a radical of the formula -NH-CO-R24; in which R24 represents a radical of the formula R25 JL26 in which R25 and R26 are identical or different and represent hydrogen. (CrC6)-alkyl or (CrC6)-alkoxycarbonyl. or R24 represents (C]-C6)-alkyl which is optionally substituted by (C6-C]2)-aryl which for its pan may be substituted by hydroxy] or (C]-C6)-alkoxy or (CrC6>alkyl optionally substituted by a radical of the formula -(S02)b-R27. in which b represents either 0 or 1 and R27 represents a radical of the formulae or R4 represents (Cj-C^-alkyl which is optionally substituted up to 3 times by identical or different radicals from the group consisting of hydroxy], azide, phenyl or by radicals of the formulae -NR28R29. -O-CO-R30 or -P(0){0-[(CrC6)-alky]]}2: in which R28 and R— are identical or different and represent hydrogen, phenyl or (Cr C6)-alkyl which is optionally substituted by hydroxy]. (Cj-C^-alkoxy or phenyl. or R28 and R29 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R31 and R32 are identical or different and represent hydrogen or (Cj-C^-alkyl R33 represents (C]-C6)-alkyl. benzyl, (CrC6)-alkoxycarbonyL (Cj-Cfc)-alkylcarbonyl. carboxyl, pyridyl, pyrimidyl or phenyl which is optionally substituted by (CrC6)-alkoxy. and R30 represents (CrC6)-alkyl; or 15 (C]-C]2)-all substituied up to 2 times by identical or different substituents from the group consisting of halogen, phenyl, tetrahydrofuranyl. tetrahydropyranyl. (CrC6)-alkoxycarbonyl. aminocarbonvl or by (CpC^-alkyl. where the latter may optionally be substituted by hydroxyl. (CrC6)-alkoxy or by a radical of the 20 formulae NR34R3$ or -O-CO-R36, in which R34 and R35 are identical or different and represent hydrogen or (C]-C6)- 25 alkvl. R36 represents (C]-C6)-alkyl. or 30 R4 represents a radical of the formula -CO-R3' in which R37 represents a radical of the formulae -(CH2)C-NR39R40 or CH2-P(0)(OR41)(OR42)r in which R38 represents hydrogen or (CrC6)-alkyl. c represents either 0 or L R39 and R40 are identical or different and represent hydrogen or (C]-Cg)-alky] which is optionally substituted by hydroxy!. R4] and R42 are identical or different and represent (C]-C6)-alkyl. or R4 represents a 5-membered heterocycle having up to 3 heieroatoms from the group consisting of S. N and 0. which heterocycle is optionally substituted aJio^efher up to 3 times, in the case of an N function a)so via this N function. by identical or different substituents from the group consisting of halogen. trifluoromethyl or by phenyl which for its part may be mono- or polysubstituted by halogen or trifluoromethyl. and/or is optionally substituted by (C3-C6-cycloalkyl, pyrryl or by (C1-C12)-alkyl 5 which for its part may be substituted by cyano, trifluoromethyl, (C1-C6)- alkoxycarbonyl, C1-C6-alkoxy, amino or by phenyl or nitro-substituted phenyl, and/or may optionally be substituted by -NR43R44; -NH-CO-CO-R45, -NH-CO-R46, NH -NH-CO-CH2-R47, -CO-R4^ or —N—^ 10 in which R43 and R44 are identical or different and represent hydrogen, benzyl, (C^-C^-alkyl or phenyl which is optionally substituted by halogen or trifluoromethyl, IS R4- represents (C1-C6)-alkoxy, R46 represents (C1-C6)-alkyl or phenyl. 20 R47 represents hydroxy], (C1-C6)-alkoxy or a radical of the formula -O-CO-R49 in which R49 represents (C1-C4)-alkyl 25 R48 represents a radical of the formula -CH2-CN or phenyl which is optionally substituted by halogen, trifluoromethyl or (C1-C6)-alkoxy, and their automers and their pharmaceutically acceptable sahs. hydranes and prodrugs. Depending on the substitution pattern, the compounds of the general formula (I) according to the invention may exist in stereoisomeric forms which are either like image and mirror image (enantiomers), or which are not like image and mirror image 5 (diastereomers). The invention relates both to the enantiomers or diastereomers and to their respective mixtures. The racemic forms can, just like the diastereomers, be separated in a known manner into the stereoisomerically uniform constituents. Certain compounds of the general formula (I) may furthermore be present in 10 tautomeric forms. This is known to the person skilled in the art, and such compounds are also within the scope of the invention. Physiologically acceptable, i.e. pharmaceuticaly acceptable, salts can be salts of the compounds according to the invention with inorganic or organic acids. Preference is 15 given to salts with inorganic acids such as, for example, hydrochloric acid, hydrobromic acid, phosphoric acid or sulfuric acid, or salts with organic carboxylic or sulfonic acids such as. for example, acetic acid, propionic acid, maleic acid, fumaric acid, malic acid, citric acid, tartaric acid, lactic acid, benzoic acid, or methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid 20 or naphthalenedisulfonic acid. Pharmaceutical!}' acceptable salts that may be mentioned are also salts with cusiomary bases, such as, for example, alkali metal salts (for example sodium salts or potassium salts), alkaline earth metal salts (for example calcium salts or magnesium 25 salts) or ammonium salts derived from ammonia or organic amines such as, for example, diethylamine. triethylamine, ethyldiisopropylamine, procaine, dibenzylamine, N-methylmorpholine, dihydroabietylamine or methylpiperidine. "Hydrates" according to the invention are those forms of the compounds of the above 30 general formula (1) which, in solid or liquid state, form a molecular compound (solvate) with water by hydration. In the hydrates, the water molecules form an adduct bv intramolecular forces, in particular hydrogen bonds. Solid hydrates contain water as water of crystallization in stoichiometric ratios, it not being necessary for the water molecules to be equivalent with respect to their binding state. Examples of hydrates are sesquihydrates, monohydrates. dihydrates or trihydrates. Also suitable are the hydrates 5 of salts of the compounds according to the invention. "Prodrugs" accordingjo the invention are forms of the compounds of the above general formula (I) which, for their part, may be biologically active or inactive, but which can be converted into the corresponding biologically active form (for example 10 metabolically, solvolytically or by other means). (C1-C12)-Alkyl denotes a straight-chain or branched alky] radical having 1 to 12 carbon atoms. Examples which may be mentioned are: methyl, ethyl, n-propyl, isopropyl. n-butyl, isobutyl, tert-buryl. n-pentyl and n-hexyl. Derived from this definition are, in ] 5 an analogous manner, the corresponding alky] groups having fewer carbon atoms, such as. for example, (C1-C6)-alky] and (C1-C4)-alkyl. Generally, preference is given to (C1-C4)-alky]. (C3-C8)-Cycloalkyl denotes a cyclic alkyl radical having 3 to 8 carbon atoms. Examples 20 which may be mentioned are: cyclopropyl. cyclobuty]. cyclopentyl, cyclohexyl. cycloheptyl or cyclooctyl. Derived from this definition are. in an analogous manner, the corresponding cycloalky] groups having fewer carbon atoms, such as, for example, (C3-C5)-cyc]oalkyl. Preference is given to cyclopropyl, cyclopentyl and cyclohexyl. 25 (C1-C6)-Alkoxy denotes a straight-chain or branched alkoxy radical having 1 to 6 carbon atoms. Examples which may be mentioned are: methoxy. ethoxy. n-propoxy. isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy and n-hexoxy. Derived from this definition are. in an analogous manner, the corresponding alkoxy groups having fewer carbon atoms, such as. for example, (C1-C6)-alkoxy and (C1-C4)-a]koxy. In 30 general, preference is given to (C1-C4)-alkoxy. Also derived from this definition is the meaning of the coiTesponding component of other, more complex substituents. such as, for example, alkoxycarbonyl. (C6-C12)-Aryl denotes an aromatic radical having 6 to 12 carbon atoms. Examples 5 which may be mentioned are: phenyl and naphtbyl. 5- to 6-membered aromatic or saturated heterocvcle having up to 3 heteroatoms from the group consisting of S. N and O denotes either a heteroaromatic radica] which is attached via a ring carbon atom of the heteroaromatic compound or. if appropriate, also 10 via a ring nitrogen atom of the heteroaromatic compound; examples which may be mentioned are: pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl. thiazolyl, oxazolyl or isoxazolyl, preference being given to pyridyl, pyrimidyl, pyridazinyl, fury] and thienyl, or denotes a saturated heterocycle which is attached via a ring carbon atom or a ring nitrogen atom, or denotes a (C5-C6)- 15 cycloalkyl radical as mentioned above; examples which may be mentioned are: letrahydrofuryl, pyrrolidinyl, piperidinyl, piperazinyl. morpholinyl, thiomorpholinyl, cyclopentyl and cyclohexyl, piperidinyl. morpbohny] and pyrrolidinyl being preferred. Preference is given to compounds of the general formula (I) according to the 20 invention in which R1 represents (C1-C4)-alkyl, 25 R- represents cyclopentyl, cycloheptyl or (C1-C10)-alkyl, R-" represents (C1-C4)-alkyL 30 R4 represents a radical of the formulae f 10 in which R5. R6 and R7 are identical or different and represent vinyl or (C1-C4)-alkyl which is optionally substituted up 3 times by identical or different substituents from the group consisting of trifluoromethyl, chlorine, (C1-C4)-alkoxy or by radicals of the formulae F F F F re II II /CF3 —O—C—C—F , — C—C—F II II CF3 F F F F /"A or —N O \ / in which R8 represents hydrogen, methyl or ethyl. 15 or R5. R6 and/or R7 represent phenyl which is optionally substituted up to 3 times by identical or different substituents from the group consisting of halogen, trifluoromethyl. nitro. cyano. carboxyl, (C1-C4)-alkyl and (C1-C4)-alkoxy 20 or R5 represents quinolyl or a radical of the formulae which may optionally be substituted up to 2 times by identical or different substituents from the group consisting of chlorine and (C1-C4)-alky] or R5 represents a radical of the formulae in which R9 and R10 are identical or different and represent hydrogen, (C1-C6)-alkyl or phenyl. or R4 represents carboxyl or represents a radical of the formulae in which Rn and R12 are identical or different and represent hydrogen or (C1-C4)-alkyl, R13 represents (C1-C4)-alkyl. R14 represents (C1-C4)-alkyl which is optionally substituted up 3 times by identical or different substituents from the group consisting of hydroxy], phenyl or by a radical of the formula -NR15R'6 . in which R15 and R16 are identical or different and represent hydrogen, phenyl or (C1-C4) -alkyl which for its part may be substituted by phenyl, or R4 represents a radical of the formula -NH-CO-NR17R18, in which R17 and R18 are identical or different and represent hydrogen or (C1-C4)-alkyl which is optionally substituted by hydroxy! or by a radical of the formulae or-NR19R20r in which R19 and R20 are identical or different and represent hydrogen, phenyl or (C1-C4) -alkyl or 7 and R18 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R2] represents hydrogen or (C1-C4)-alkyl. a represents either 1 or 2. R22 represents hydroxyl or (C1-C4)-alkyl which is optionally substituted by hvdroxyl. R17 and/or R18 represent phenyl which is optionally substituted by chlorine, trifluoroethyl or by -SCF3 or R] 7 represents hydrogen and R18 represents a radical of the formula -S02-R23 . in which R23 represents (C1-C4)-alkyl or phenyl which is optionally substituted by halogen. or represents a radical of the formulae or R4 represents a radical of the formula -NH-CO-R24. in which R24 represents a radical of the formula in which R25 and R26 are identical or different and represent hydrogen, (C1-C4)-alkyl or (C1-C4)-alkoxycarbonyl, or R24 represents (C1-C4)-alkyl which is optionally substituted by phenyl which for its part may be substituted by hydroxy] or (C1-C4)-alkoxy or (C1-C4)-alkyl optionally substituted by a radical of the formula -(S02)b-R27, in which b represents either 0 or 1 and R27 represents a radical of the formulae represents (C1-C11)-alkyl which is optionally substituted up to 3 times by identical or different substituents from the group consisting of hydroxyl. azide. pheny] or by radicals of the formulae -NR28R29; -O-CO-R30 or -P(O){O-[(C1-C6)-alkyl]}2; in which R28 and R29 are identical or different and represent hydrogen, phenyl or (C1-C4) -alkyl which is optionally substituted by hydroxyl. (C1-C4)-alkoxy or phenyl. or R28 and R29 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R31 and R32 are identical or different and represent hydrogen or (C1-C4)-alkyl R33 represents (C1-C4)-alky]. benzyl. (C1-C4)-alkoxycarbonyl. (C1-C4)-alkylcarbonyl. carboxyl. pyridyl. pyrimidyl or pheny] which is optionally substituted by (C1-C4)-alkoxy. and R30 represents (C1-C6)-alkyL or (C1-C11)-alkyl is optionally substituted by triazolyl which for its part may be substituted up to 2 times by identical or different substituents from the group consisting of halogen, phenyl, tetrahydrofuranyl. tetrahydropyranyl, (C1-C4) alkoxycarbony], aminocarbony! or by (C1-C4)-alkyl. where the latter may optionally be substituted by hydroxy]. (C1-C4)-a]koxy or by a radical of the formulae NR34R35 or -O-CO-R36. r— - ■ ■ - in which R34 and R35 are identical or different and represent hydrogen or (C1-C4)-alkyl. R36 represents (C1-C4)-alkyl. R4 represents a radical of the formula -CO-R37. in which R37 represents a radical of the formulae 10 -(CH2)C-NR39R40 or - CH2-P(O)(OR4 1 )(OR42); in which R38 represents hydrogen or (C1-C4)-aikyl. c represents either 0 or 1. R39 and R40 are identical or different and represent hydrogen or (C1-C4)-alkyl which is optionally substituted by hydroxy]. R41 and R42 are identical or different and represent (C1-C4)-alkyl. 15 or R4 represents a radical of the formula 20 which is optionally substituted altogether up to 3 times, in the case of the pyrazole also via the N function, by identical or different substitutents from the group consisting of chlorine, trifluoromethyl or by phenyl which for its part may be mono- or polysubstituted by chlorine or trifluoromethyl. and/or is optionally substituted by cyclopentyl. cyclohexyl, pyrryl or by (C1-C12)- 5 alkyl which for its part may be substituted by cyano, trifluoromethyl, (C1-C4) alkoxycarbonyl. (C1-C4)-alkoxy. amino or by phenyl or nitro-substituted phenyl. and/or may optionally be substituted by -NR43R44, -NH-CO-CO-R45, -NH-CO-R46, 10 in which R43 and R44 are identical or different and represent hydrogen, benzyl, ((C1-C4))-alkyl or phenyl which is optionally substituted by halogen or trifluoromethyl. 15 R45 represents (C1-C5)-alkoxy. R46 represents (C1-C5)-alkyl or phenyl. 20 R47 represents hydroxyl, (C1-C4)-alkoxy or a radical of the formula -O-CO-R49 in which R49 represents (C]-C3)-alkyl 25 R48 represents a radical of the formula -CH2-CN or phenyl which is optionally substituted by chlorine, trifluoromethyl or (C1-C4)-alkoxy, and their tauiomers and their pharmaceutical!}' acceptable salts, hydrates and 30 prodrugs. 10 Particular preference is given to compounds of the general formula (I) according to the invention. in which R1 represents (C1-C4)-alkyl. R2 represents cyclopentyl, cyclohexyl, cycloheptyl or (C1-C10)-alkyl, R3 represents (C1-C4)-alkyl, R4 represents a radical of the formulae 15 in which R5. R6 and R7 are identical or different and represent vinyl or (C1-C4)-alky] which is 20 optionally substituted up to 3 times by identical or different substituents from 25 in which R8 represents hydrogen, methyl or ethyl. the group consisting of trifluoromethyl. chlorine. (C1-C4)-alkoxy or by radicals of the formulae or R5. R6 and/or R7 represent phenyl which is optionally substituted up to 3 times by identical or different substituents from the group consisting of halogen, cyano, (C1-C4)-alky] and (C1-C4)-alkoxy or R5 represents a radical of the formulae which may optionally be substituted up to 2 times by identical or different substituents from the group consisting of chlorine and (C1-C4)-alkyl 15 or R- represents a radical of the formula -NR9R10 20 in which R9 and R10 are identical or different and represent hydrogen, (C1-C4)-alky] or phenyl. 25 or R4 represents carboxyl or represents a radical of the formulae -CO-R13 or-O-R14, 5 in which R13 represents (C1-C4)-alkyl. 10 R14 represents (C1-C4)-alkyl which is optionally substituted up to 3 times by identical or different substituents from the group consisting of hydroxy] or by a radical of the formula -NR15R16, in which 15 R15 and R16 are identical or different and represent hydrogen or (C1-C4)-alkyl which for its pan may be substituted by phenyl, or 20 R4 represents a radical of the formula -NH-CO-NR,7R18, in which R'7 and R18 are identical or different and represent hydrogen or (C1-C4)-alkyl 25 which is optionally substituted by hydroxyl. or R17 and R18 together with the nitrogen atom to which they are attached form 30 a heterocyclic ring of the formulae in which R21 represents hydrogen or (C1-C4)-alkyl. and/or R18 represent phenyl which is optionally substituted by chlorine, trifluoroethyl or by -SCF3 represents hydrogen and represents a radical of the formula -SO2-R23 - in which R23 represents (C1-C4)-a]kyl or phenyl which is optionally substituted by halogen. or represents a radical of the formulae R4 represents a radical of the formula -NH-CO-R24, in which R24 represents (C1-C4)-alky] which is optionally substituted by phenyl which for its part may be substituted by hydroxy! or (C1-C4)-alkoxy or (C1-C4)-alkyl is optionally substituted by a radical of the formula -(S02)b-R27, in which b represents either 0 or 1 and R27 represents a radical of the formulae or R4 represents (C1-C6)-alkyl which is optionally substituted up to 3 times by identical or different substituents from the group consisting of hydroxy], phenyl or by radicals of the formulae -NR28R29 or -O-CO-R30 , in which R28 and R29 are identical or different and represent hydrogen, phenyl or(C1-C4) -alkyl which is optionally substituted by hydroxyl, (C1-C4)-alkoxy or phenyl. or R28 and R29 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R3] and R32 are identical or different and represent hydrogen or (C1-C4)-alky] R33 represents (C1-C4)-alkyl. benzyl. (C1-C4)-alkoxycarbonyl. (C1-C4)-alkylcarbonyl. carboxyl. pyridyl. pyrimidyl or phenyl which is optionally substituted by (C1-C4)-alkoxy. and R30 represents (C1-C6)-alkyl. or (C1-C4)-alkyl is optionally substituted by triazolyl which for its part may opiionally be substituted up to 2 times by identical or different substituents from the group consisting of (C1-C4)-alkyl. where the latter may optionally be substituted by hydroxy! or (C1-C4)-alkoxy. in which or R4 represents a radical of the formula -CO-R37. in which R37 represents a radical of the formulae in which R38 represents hydrogen or (C1-C4)-alkyl. c represents either 0 or 1. R39 and R40 are identical or different and represent hydrogen or (C1-C4)-alky) which is optionally substituted by hydroxy!. or R4 represents a radical of the formula 10 which is optionally substituted altogether up to 3 times, in the case of the pyrazole also via the N function, by identical or different substituents from the group consisting of trifluoromethyl or by phenyl which for its part may be mono- or polysubstituted by chlorine or trifluoromethyl. and/or is optionally substituted by cyclopentyl. cyclohexyl or by (C1-C6)-alkyl which for its part may be substituted by (C1-C4)-alkoxy. amino or by phenyl,. and/or may optionally be substituted by -NR43R44, -NH-CO-R46, -NH-CO-CH2-R47 15 or -CO-R48 : in which R43 and R44 are identical or different and represent hydrogen, benzyl, (C1-C4)-alkyl 20 or phenyl which is optionally substituted by halogen or trifluoromethyl, R46 represents (C1-C4)-alkyl or phenyl, R47 represents hydroxyl or (C1-C4)-alkoxy. 25 R48 represents phenyl which is optionally substituted by chlorine, trifluoromethyl or (C1-C4)-alkoxy. and their tautomers and their pharmaceutically acceptable salts, hydrates and prodrugs. Very particular preference is given to the compounds according to the invention 5 having the structures below: . and their tautomers and their pharmaceutical]}-' acceptable salts, hydrates and prodrugs. The compounds of the general formula (I) according to the invention are obtained when [A] in the case that R4 is a radical as defined above which is attached via a nitrogen atom, compounds of the general formula (11) R1, R2 and R3 are as defined above are initially converted, by reaction with HNO3/CF3CO2H. into the compounds of the genera] formula (III) in which R1. R2 and R3 are as defined above. in a next step reduced with Ho/Pd-C to give amines of the general formula (IV) in which R1. R2 and R3 are as defined above. and finally reacted with compounds of the general formula (V) A - D (V), in which 5 if A represents the radicals R5, R6 or R7 listed above under R4, ] 0 D represents the radical -SO2CI. and if A represents the radical R24 listed above under R4 . 15 D represents the radical -CO-C1 and if 20 A represents the radicals R17 or R]8 listed above under R4, D represents the radicals -NH-CO-CL -N=C=0 or -S02-NOO. in inert solvents, if appropriate in the presence of a base and/or an auxiliary. 25 or [B] if R4 represents a radical as defined above which is attached via -NH-CO. alternatively compounds of the general formula (IV) are initially reacted with a 30 bifunctional spacer B and then with compounds of the general formula (VI) HNR49R50 (VI); in which if 5 B denotes a radical of the formula Cl-CH2-CO-Cl, R49 and R50 together with the nitrogen atom to which they are attached are within the scope of the meaning of R27 given above. 10 and if B denotes a radical of the formula Cl-CO-OCCl3. 15 R49 and R50 are within the scope of the meanings of R17 and R18 given above. and if B denotes a radical of the formula CISO2-N=C=O. 20 R49 and R50 together with the nitrogen atom to which they are attached are within the scope of the meaning of R23 given above. if appropriate in an inert solvents. 25 or [C] if R4 represents a radical as defined above which is attached via a carbon atom, compounds of the general formula (11) are initially converted by reaction with 30 formaldehyde/HCl into the compounds of the general formula (VII) in which R1, R2 and R3 are as defined above. and then, by methods familiar to the person skilled in the art, reacted • with amines to give the corresponding benzylamines. 0 • with phosphites to give the corresponding phosphonates, • with azide and subsequently alkynes to give the corresponding triazoles, or 15 [D] if R4 represents a radical as defined above which is attached via -CO- or represents one of the heterocycles listed above. initially compounds of the general formula (11) are, by reaction with Br-CH2-CO-Br 20 in the presence of A1C]3. converted into compounds of the general formula (VH1) in which R1, R2 and R3 are as defined above, and then, by methods familiar to the person skilled in the art. reacted • with Sm.l2 t° ?Jve tne corresponding acetophenones. • with Br2/NaOH 10 give carboxylic acids and then with amines to give the corresponding amides. • with NaBH4/NaOH to give epoxides and then with amines to give the corresponding a-hydroxyamines. • with KCN and then hydrazines to give the corresponding aminopyrazoles, • with thioureas to give the corresponding 2-aminothiazoles. • with thioamides to give the corresponding thiazoles • with phosphnes to give the corresponding p-ketophosphonates, • with amines to give the corresponding a-aminoketones or [E] in the case that R4 is a radical as defined above which is attached via an oxygen atom, compounds of the general formula (IX) in which R1. R2 and R3 are as defined above 10 are initially converted, by reaction with meta-chloroperbenzoic acid (m-CPBA) into compounds of the general formula (X) 15 in which R1. R2 and R3 are as defined above. and then reacted with the corresponding amines of the general formula (XI) Solvents which are suitable for the individual steps are the customary organic solvents which do not change under the reaction conditions. These preferably include ethers, such as diethyl ether, dioxane, tetrahydrofuran, glycol dimethyl ether, or hydrocarbons, such as benzene, toluene, xylene, hexane, cvclohexane or mineral oil fractions, or halogenated hydrocarbons, such as dichloromethane. trichloromethane, carbon tetrachloride, dichloroethane. trichloroethylene or chlorobenzene, or ethyl acetate, dimethylformamide, hexamethylphosphoric triamide. acetonitrile, acetone, dimethoxyethane or pyridine. It is also possible to use mixtures of the solvents mentioned. The reaction temperatures can generally be varied within a relatively wide range. In general, the reactions are carried out in a range of from -20°C to 200°C, preferably from 0°C to 70°C. The process steps according to the invention are generally carried out at atmospheric pressure. However, it is also possible to operate under elevated pressure or reduced pressure (for example in a range of from 0.5 to 5 bar). 5 The reactions can be carried out. for example, in a temperature range of from 0°C to room temperature and at atmospheric pressure. The compounds of the general formula (II) can be prepared by converting compounds of the general formula (XII) in which RJ is as defined above 15 by reaction of the nitrile group into the corresponding amidines. reacting these initially with hydrazine and then with compounds of the general formula (XIII) in which 20 R1 and R2 are as defined above. to the compounds of the general formula (XIV) in which R1, R2 and R3 are as defined above 5 and then cyclizing these by action of POCI3 to give compounds of the general formula (II). For details of this process, reference can be made to WO-A-99/24433, the content of which is hereby included in its entirety by reference. 10 Most of the compounds of the general formulae (III), (IV), (VII), (VIII) and (X) are novel and can be prepared as described above. 15 The compounds of the general formulae (V), (VI), (XI), (XII), (XIII) and (XIV) are known per se or can be prepared by customary methods. Some of the compounds of the genera] formula (IX) are novel, and they can be prepared by convening compounds of the general formula (XV) in which 20 R3 is as defined above by reaction of the nitrile group into the corresponding amidines, which are then reacted with hydrazine and subsequently with compounds of the general formula (XII) and finally cyclized with POCI3 to give the corresponding compounds of the general formula (IX). 5 The compounds of the general formula (XV) are known per se or can be prepared by customary methods. The compounds of the general formula (I) according to the invention have an 10 unforeseeable, useful spectrum of pharmacological action. They inhibit either one or more of the cGMP-metabolizing phosphodiesterases(PDE 1. PDEII and PDE V). This results in an increase of cGMP. The differentiated expression of the phosphodiesterases in different cells, tissues and organs and the differentiated 15 subcellular localization of these enzymes allows, in combination with the selective inhibitors according to the invention, the different cGMP-regulated processes to be addressed selectively. The compounds according to the invention moreover intensify the action of substances. 20 such as. for example. EDRF (endothelium-derived relaxing factor). ANP (atrial natriuretic peptide), of nitrovasodilators and other substances which increase the cGMP concentration by a mode different to that of phosphodiesterase inhibitors. Accordingly, the compounds of the general formula (I) according to the invention are 25 suitable for the prophylaxis and/or treatment of disorders in which an increase of the cGMP concentration is beneficial, i.e. cGMP-related diseases. These include cardiovascular disorders, disorders of the urogenital system and cerebrovascular disorders. 30 In the context of the present invention, the term "cardiovascular disorders" includes disorders such as. for example, hypertension, neuronal hypertonia, stable and unstable angina, peripheral and cardial vasculopathies, airhythmiae, thromboembolic disorders and ischemias such as myocardial infarction, stroke, transitory and ischemic attacks, angina pectoris, obstruction of peripheral circulation, prevention of restenoses after thrombolysis therapy, percutaneous transluminal angioplasty (PTA), percutaneous 5 transluminal coronary angioplasties (PTCA) and bypass. Furthermore, the compounds of the general formula (I) according to the invention may also be of importance for cerebrovascular disorders, cerebral ischemia, stroke, reperfusion damage, cerebral trauma, edema or cerebral thrombosis. 10 In addition, the present compounds are also suitable for improving perception, concentration power, learning power or memory power after cognitive disorders, such as occur, for example, in situations/illnesses/syndromes such as mild cognitive impairment, age-associated learning and memory disorders, age-associated memory 15 loss, vascular dementia, craniocerebral trauma, stroke, dementia which occurs after strokes (post-stroke dementia), post-traumatic craniocerebral trauma, general concentration disorders, concentration disorders in children with learning and memory problems. Alzheimer's disease, vascular dementia, dementia with Lew}' bodies, dementia with degeneration of the frontal lobes including Pick's disease, 20 Parkinson's disease, progressive nuclear palsy, dementia with corticobasa] degeneration, amyolateral sclerosis (ALS). Huntington's disease, multiple sclerosis, thalamic degeneration. Creutzfeld-Jacob dementia, HIV dementia, schizophrenia with dementia or Korsakoff psychosis. 25 Owing to their relaxing action on smooth muscles, they are suitable for treating disorders of the urogenital system such as hypertrophy of the prostate, incontinence and in particular for the treatment of erectile dysfunction and female sexual dysfunction. Activity of the phosphodiesterases (PDEs) 30 The cGMP-siimulable PDE ]1. the cGMP-inhibitable PDE 111 and the cAMP-specific PDE IV were isolated either from porcine or bovine heart myocardium. The Ca2"- calmodulin-stimulable PDE 1 was isolated from porcine aorta, porcine brain or preferably from bovine aorta. The cGMP-specific PDE V was obtained from porcine small intestine, porcine aorta, human blood platelets and preferably from bovine aorta. Purification was earned out by anionic exchange chromatography on MonoQ 5 Pharmacia essentially according to the method of M. Hoey and Miles D. Houslay. Biochemical Pharmacology, Vol. 40. 193-202 (1990) and C. Lugman et al. Biochemical Pharmacology Vol. 35 1743-1751 (1986). The enzyme activity was determined in a test batch of 100 u.1 in 20 mM tris/HCl buffer 10 pH 7.5 which contains 5 mM MgCl;2, 0.1 mg/ml bovine serum albumin and either 800 Bq of JHcAMP or JHcGMP. The final concentration of the corresponding nucleotides is 10'6 mol/1. The reaction is started by addition of the enzyme and the amount of enzyme is proportioned such that about 50% of the substrate is converted during the incubation time. To test cGMP-stimulate PDE II, JHcAMP is used as ]5 substrate and 10'6 mol/1 unlabeled cGMP are added to the mixture. To test Ca2+- calmodulin-dependent PDE 1. 1 u.M of CaG? and 0.1 u.M of calmodulin are additionally added to the reaction mixture. The reaction is stopped by addition of 100 u.1 of acetonitrile which contains 1 mM of cAMP and 1 mM of AMP. 100 u.1 of the reaction mixture are separated by HPLC. and the products of the separation are 20 determined on-line in a quantitative manner using a flow scintillation counter. What is measured is the substance concentration at which the reaction rate is reduced by 50%. Additionally, the "phosphodiesterase [3H] cAMP-SPA enzyme assay" and the "phosphodiesterase [JH] cGMP-SPA enzyme assay" from Amersham Life Science were used for testing. The test was carried out according to the test protocol of the 25 manufacturer. To detemiine the activity of PDE II. the [JH] cAMP SPA assay was used, and 10'e M cGMP were added to the reaction mixture to activate the enzyme. To measure PDE L 10"'M calmodulin and ] u.M CaCb were added to the reaction mixture. PDE V was measured using the [JH] cGMP SPA assay. 30 In principle, inhibition of one or more phosphodiesterases of this type results in an increase of the cGMP concentration. Thus, the compounds are of interest for all therapies in which an increase in the cGMP concentration is considered to be beneficial. The cardiovascular effects were investigated using normotensive and SH rats and dogs. 5 The substances were administered intravenously or orally. The study for erection-triggering action was carried out using awake rabbitsfH. Naganuma. T. Egashira, J. Fuji, Clinical and Experimental Pharmacology and Physiology 20, 177-183 (1993)]. The substances were administered orally or 10 parenterally. The novel active compounds and their physiologically acceptable salts (for example hydrochlorides, maleates or lactates) can be convened in a known manner into the customary formulations, such as tablets, coated tablets, pills, granules, aerosols, syrups, 15 emulsions, suspensions and solutions, using inert non-toxic, pharmaceutically suitable excipients or solvents. In this case, the therapeutically active compound should in each case be present in a concentration of from approximately 0.5 to 90% by weight of the total mixture, i.e. in amounts which are sufficient in order to achieve the dosage range indicated. 20 The formulations are prepared, for example, by extending the active compounds using solvents and/or excipients. if appropriate using emulsifiers and/or dispersants, it optionally being possible, for example, to use organic solvents as auxiliary solvents if the diluent used is water. 25 Administration is earned out in a customary manner, preferably orally, transdermally or parenterally, for example perlingually, buccally. intravenously, nasally, rectally or inhalatively. 30 For human use. in the case of oral administration, doses of from 0.001 to 50 mg/kg. preferably 0.01 mg/kg - 20 mg/kg. are generally administered. In the case of parenteral administration, for example nasally, buccally or inhalatively via mucosa, it is good practice to use doses of 0.001 mg/kg - 0.5 mg/kg. In spite of this, if appropriate it may be necessary to depart from the amounts 5 mentioned, namely depending on the body weight or the administration route, on the individual response toward the medicament, the manner of its fonnulation and the time or interval at which administration takes place. Thus, in some cases it may be adequate to manage with less than the abovementioned minimum amounts, while in other cases the upper limit mentioned has to be exceeded. In the case of the administration of 10 relatively large amounts, it may be advisable to divide these into several individual doses over the course of the day. The compounds according to the invention are also suitable for use in veterinary medicine. For use in veterinary medicine, the compounds or their non-toxic salts can be ] 5 administered in a suitable fonnulation in accordance with general veterinary practice. Depending on the kind of animal to be treated, the veterinary surgeon can determine the administration route and the dosage. The present invention is illustrated by the examples below: however, the invention is 20 by no means limited by these examples. In the structural formulae given below which contain the radical this always H denotes Preparation of the precursors Example 1A 2-Butyrylaminopropionic acid CH3 HO. X, If 22.27g (250 mmol) of D,L-alanine and 55.66 g (550 mmol) of triethylamine are dissolved in 250 ml of dichloromethane, and the solution is cooled to 0°C. 59.75 g (550 mmol) of trimethylsilyl chloride are added dropwise. and the solution is stirred 10 at room temperature for 1 hour and at 40°C for one hour. After cooling to -10°C. 26.64 g (250 mmol) of butyry] chloride are added dropwise. and the resulting mixture is stirred at -10°C for 2 hours and at room temperature for one hour. With ice-cooiing, 125 ml of water are added dropwise. and the reaction mixture is stirred at room temperature for 15 minutes. The aqueous phase is evaporated to dryness, the 15 residue is triturated with acetone and the mother liquor is filtered off with suction. Following removal of the solvent, the residue is chromatographed. The resulting product is dissolved in 3N aqueous sodium hydroxide solution, and the resulting solution is evaporated to dryness. The residue is taken up in cone. HC1 and again evaporated to dryness. The residue is triturated with acetone, the precipitated solid is 20 filtered off with suction and the solvent is removed under reduced pressure. This gives 28.2 g (71%) of a viscous oil which crystallizes after some time. 200 MHz 'H-NMR (DMSO-d6): 0.84 (L 3H); 1.22 (d. 3H); 1.50 (hex, 2H); 2.07 (t, 2H); 4.20 (quin, 1H); 8.09 (d, 1H). Example 2A 2-Butyrylaminobutyric acid 5 25.78 g of 2-aminobutyric acid (250 mmol) and 55.66 g (550mmol) of triethylamine are dissolved in 250 ml of dichloromethane. and the solution is cooled to 0°C. 59.75 g (550 mmol) of trimethylsilyl chloride are added dropwise, and the solution is stirred at room temperature for 1 hour and at 40°C for one hour. After cooling to -10°C, 26.64 g (250 mmol) of butyryl chloride are added dropwise. and the resulting 10 mixture is stirred at -10°C for 2 hours and at room temperature for one hour. With ice-cooling. 125 ml of water are added dropwise. and the reaction mixture is stirred at room temperature for 15 minutes. Aqueous sodium hydroxide solution is added to the organic phase, and the organic solvent is removed under reduced pressure. The residue is acidified and the precipitated solid is triturated once with water and twice 15 with petroleum ether and dried under reduced pressure at 45°C. 29.1 g (67%) of a colorless solid. 200 MHz 'H-NMR (DMSO-d6):0.88 ( 2t, 6H): 1.51 (quart.. 2H); 1.65 (m, 2H); 2.09 (t, 2H); 4.10 (m. 1H): 8.01 (dr 1H); 12.25 (s,m 1H). 20 Example 3A 2-(2-Ethy])butanoylaminopropionic acid cm HO- 24.5 g (0.275 mol) of D.L-alanine are initially charged in 250 ml of dichloromethane, and 61.2 g (0.605 mol) of triethylamine are added. The mixture is cooled to 0°C. and 65.7 g (0.605 mol) of trimethylsilyl chloride are added. The mixture is stirred at room temperature for one hour and at 40°C for one hour. The mixture is cooled to -10°C, 5 and 37 g (0.275 mol) of 2-ethylbutyryl chloride are slowly added dropwise. The mixture is stirred at -10°C for two hours and at room temperature overnight. The mixture is cooled in an ice bath, and 150 ml of water are added. 50 g (1.25 mol) of NaOH, dissolved in 100 ml of water, are added and the aqueous phase is separated off and concentrated. The residue is again taken up in water and acidified with 10 concentrated hydrochloric acid, the aqueous solution is extracted repeatedly with dichloromethane and the organic phase is dried over I^SCM and concentrated. Yield: 43.55 g (84.6% of theory) 200 MHz 'H-NMR (CDC13): 0.91 (t, 6H); 1.5 (d, 3H); 1.52-1.73 (m, 4H); 1.99 (m, 1H): 4.61 (quin, 1H); 6.25 (d, 1H); 6.76 (bs, 1H). 15 Example 4A 2-(2,2-Dimefhy])pemanoy]aminopropionic acid CH:. HO. A. 20 48.04 g (344.2 mmol) of D,L-alanine methyl ester hydrochloride and 76.67 g (757.2 mmol) of triethylamine are dissolved in 600 ml of dichloromethane, and 56 g (344.2 mmol) of 2.2-dimethylpentanoy] chloride in 50 ml of dichloromethane are added dropwise at 0°C. The mixture is stirred at RT for 2 h. filtered off and washed with 10% strength HCl solution, saturated sodium bicarbonate solution and saturated 25 sodium chloride solution. The mixture is dried over sodium sulfate and then concentrated. The residue is taken up in methanol, and a solution of 55 g (1377 mmol) of sodium hydroxide in 300 1 of water is added. The mixture is stirred at RT for 2 hours and then filtered off. and the methanol is evaporated under reduced pressure. The aqueous phase is acidified using concentrated hydrochloric acid solution and extracted with ethyl acetate (2 x). The combined ethyl acetate phases are dried over sodium sulfate and concentrated. The residue is crystallized from ether. Yield: 30 g (40.5%) 5 M.p.:168°C Example 5A 2-HeptanoylaminopropJonic acid 10 30 g (291 mmol) of D.L-alanine methyl ester hydrochloride and 64.77 g (640 mmol) of triethylamine are initially charged in 300 ml of dry methylene chloride at 0°C. 43.24 g (291 mmol) of heptanoy] chloride in 50 ml of methylene chloride are added dropwise. The mixture is allowed to warm to RT and stirred at this temperature for 15 2 h. The precipitate is filtered off and the methylene chloride phase is extracted with saturated sodium bicarbonate solution and with saturated sodium chloride solution and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is dissolved in 300 ml of methanol. 300 ml of water, in which 46.55 g (1164 mmol) sodium hydroxide are dissolved, are added to this solution, and the 20 mixture is stirred at RT for 2 h. The mixture is filtered, the methanol is evaporated using a rotary evaporator and the aqueous phase that remains is acidified to pH 1-2 using cone. Hcl. The precipitated product is filtered off and dried. Extraction of the aqueous phase with ethyl acetate gives a second product fraction. Yield: 50 g (85.4%) 25 'H-NMR (CD3OD): 0.9 (t. 3H); 1.2-1.4 (m. 9H): 1.6 (quin.r 2H); 2.2 (t. 2H): 4.38 (quar.. 1H). Example 6.A 2-Octanoylaminopropionic acid The preparation is carried out analogously to the procedure of example 1A using 16.5 g (0.185 mol) of D.L-alaniner 41.23 g (0.407 mol) of tri ethyl amine, 44.27 g (0.407 mol) of trimethylsilyl chloride and 30.12 g (0.185 mol) of octanoyl chloride. The product crystallizes from toluene/n-hexane. Yield: 34.3 g (86%) 'H-NMR (CD3OD): 0.9 (t, 3H); 1.2-1.4 (m; 11H); 1.6 (quin. 2H); 2.2 (t, 2H); 4.35 (quar 1H). 10 Example 7A 2-Decanoylaminopropionic acid CH, 15 20 The preparation is earned out analogously to the procedure of example 4A using 19.0 g (l84mmol) of D.L-alanine methyl ester hydrochloride and 35.14 g (184 mmol) of decanoyl chloride. Yield: 37.3 g (83.2%) 'H-NMR (CD?OD): 0.9 (t. 3H); 1.2-1.4 (m. 15H): 1.6 (m. 2H); 2.2 (t, 2H); 4.35 (quar.. 1H). Example 8A 2-(2-Ethy])octanoylaminopropionic acid 5 18.6 g (0.211 mol) of D.L-alanine and 46.6 g (0.41 mol) of triethylamine are initially charged in 300 ml of dichloromethane. At 0°C. 50.09 g (0.461 mol) of trimethylsilyl chloride are added dropwise. and the mixture is stirred at room temperature for 1 h and then at 40°C for 1 h. The solution is cooled to -10°C, and 40 g (0.21 mol) of 2-ethyloctanoyl chloride in 50 ml of dichloromethane are added dropwise. The 10 mixture is stirred at room temperature overnight. 100 ml of water are then added dropwise with ice-cooling and the mixture is stirred for 10 minutes. The phases are separated, the aqueous phase is reextracted twice with in each case 100 ml of dichloromethane and the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The residue is crystallized from toluene by 15 adding n-hexane and is dried at 60°C. Yield: 3.9 g (78.2%) 'H-NMR (CDC13): 0.9 (m. 6h); 1.25 (pseudo s; 8H); 1.45 (d. 3H); 1.4-1.7 (m, 4H); 2.0 (m. 1H): 4.6 (quin. 1H): 6.1 (d, 1H). 20 Example 9A 2-Cyclopenianoylaminopropionic acid 16.8 g (0.189 mol) of DX-alanine and 41.98 g (0.415 mol) of triethylamine are initially charged in 200 ml of dichloromethane. At 0°C. 45.07 g (0.415 mol) of trimethylsilyl chloride are added dropwise, and the mixture is stirred at room temperature for 1 h and then at 40°C for 1 h. The solution is cooled to -10°C. and 25 g (0.189 mol) of cyclopentanecarbonyl chloride are added dropwise. The mixture is stirred at -10°C for 2 h and at room temperature for 1 h. With ice-cooling, 100 ml of water are added dropwise. the mixture is stirred for 10 min. and the resulting precipitate is filtered off with suction. The precipitate is washed with 300 ml of water and then with 300 ml of diethyl ether and subsequently dried at 60°C. Yield: 25.8 g (73.9% of theory) 'H-NMR (CD3OD): 1.35 (d, 3H); 1.5 - 1.9 (m, 8H); 2.7 (quin, 1H); 4.5 (quar.; 1H): Example 10A 2-Cyclopentanoylaminobutyric acid 10.31 g of 2-aminobutyric acid (100 mmol) and 22.26 g (220 mmol) of triethylamine are dissolved in 100 ml of dichloromethane. and the solution is cooled to 0°C. 23.90 g (220 mmol) of trimethylsilyl chloride are added dropwise. and the solution is stirred at room temperature for 1 hour and at 40°C for one hour. After cooling to -10°C. I3.26g (lOOmmol) of cyclopentanecarbonyl chloride are added dropwise. and the resulting mixture is stirred at -10°C for 2 hours and at room temperature for one h. With ice-cooling. 50 ml of water are added dropwise. and the reaction mixture is stirred at room temperature for 15 minutes. The mixture is diluted with water and dichloromethane and the resulting precipitate is filtered off with suction: 11.1 g (55%) oJ a colorless solid. The dichloromethane phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is triturated with toluene and the precipitate is filtered off with suction: 5.75 g (28%) of a colorless solid. 200 MHz 'H-NMR (DMSO-d6): 0.88 (t, 3H); 1.61 (m, 10H); 2.66 (m, 1H); 4.09 (hex.. 1H); 7.97 (d, 1H); 12.44 (s, 1H). Example 11A 2-Cycloheptanoylaminopropionic acid 10 15 The preparation is carried out analogously to the procedure of example 4A using 20 g (143 mmol) of D.L-alanine methyl ester hydrochloride and 23.02 g (143 mmol) of cycloheptanoyl chloride. Yield: 16 g (52.4%) 'H-NMR (CD?OD): 1.35 (d. 3H); 1.45 - 1.65 (m. 8H): 1.7 - 1.95 (m. 4H); 2.35 (m. lH);4.25(quar.: 1H). 20 Example 12A 2 -Eth ox ybenzon i tri 1 e 25 g (210 mmol) of 2-bydroxybenzonitrile. 87g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide are refluxed in 500 ml of acetone overnight. The solid is filtered off. the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. This gives 30.0 g (97%) of a colorless liquid. 200 MHz 'H-NMR (DMSO-d6): 1-48 (tr 3H): 4.15 (quart, 2H); 6.99 (dts 2H); 7.51 (dt, 2H). Example 13A 2-Ethoxybenzami dine hydrochl ori de CH J 3 NH 'NH2 xHCI ^^ 2L4g (400 mmol) of ammonium chloride are suspended in 375 ml of toluene, and 10 the suspension is cooled to 0°C. 200 ml of a 2 M solution of trimethylaluminum in hexane are added dropwise, and the mixture is stirred at room temperature until the evolution of gas has ceased. Following addition of 29.44 g (200 mmol) of 2-ethoxybenzonitrile. the reaction mixture is stirred at 80°C (bath) overnight. The cooled reaction mixture is. with ice-cooling, added to a suspension of lOOg of silica 15 gel and 950 ml of chloroform, and the mixture is stirred at room temperature for 30 minutes. The mixture is filtered off with suction and the filter cake is washed with the same amount of methanol. The mother liquor is concentrated, the resulting residue is triturated with a mixture of dichloromethane and methanol (9:1). the solid is filtered off with suction and the mother liquor is concentrated. This gives 30.4 g 20 (76%) of a colorless solid. 200 MHz 'H-NMR (DMSO-d6): 1.36 (t. 3H): 4.12 (quart., 2H); 7.10 (t. 1H); 7.21 (d. 1H): 7.52 (m. 2H): 9.30 (s; broad. 4H). Example 14A 25 2-Propoxybenzonitrile 75 g (630 mmol) of 2-hydroxybenzonitrile. 174 g (1.26 mol) of potassium carbonate and 232.3 g (1.89 mol) of n-propy] bromide in 1 1 of acetone are refluxed overnight. The solid is filtered off, the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. B.p.: 89°C (0.7 mbar) Yield: 95.1 g (93.7% of theory) 10 Example 15A 2-Propoxybenzamidine hydrochloride '2 xHCI 21.41 g (400 ml) of ammonium chloride are suspended in 400 ml of toluene and cooled to 0-5°C. 200 ml of a 2 M solution of triethylaluminum in hexane are added 15 dropwise. and the mixture is stirred at room temperature until the evolution of gas has ceased. Following addition of 32.2 g (200 mmol) of 2-propoxybenzonitrile. the reaction mixture is stirred at 80°C (bath) overnight. The cooled reaction mixture is. with ice-cooling, added to a suspension of 300 g of silica gel and 2.85 ml of ice-cooled chloroform and stirred for 30 minutes. The mixture is filtered off with suction 20 and the filter cake is washed with the same amount of methanol. The solvent is distilled off under reduced pressure, the residue is triturated in 500 ml of a mixture of dichloromethane and methanol (9:1). the solid is filtered off and the mother liquor is concentrated. The residue is triturated with petroleum ether and filtered off with suction. This gives 22.3 g (52%) of product. 2: 200 MHz 'H-NMR (CD?OD): 1.05 (i. 3H): 1.85 (sex. 2H): 4.1 it. 2H): 7.0 - 7.2 (m. 2H); 7.5- 7.65 Example 16A 2-(2-Ethoxyphenyl)-5-methyl-7-propyl-3H-imidazo[5,l-f|[l,2.4]-triazin-4-one O 7.16 g (45 mmol) of 2-butanoylaminopropionic acid (example 1A) and 10.7 g of pyridine are dissolved in 45 ml of tetrahydrofuran and. after addition of a spatula tip of 4-dimethylaminopyridine. heated at reflux. 12.29 g (90 mmol) of monoethyl oxalyl chloride are slowly added dropwise. and the reaction mixture is refluxed for 3 hours. 10 The mixture is poured into ice-water and extracted 3 times with ethyl acetate, and the extracts are dried over sodium sulfate and concentrated. The residue is taken up in 15 ml of ethanol and refluxed with 2.15 g of sodium bicarbonate for 2.5 hours. The cooled solution is filtered. With ice-cooling. 2.25 g (45 mmol) of hydrazine monohydrate are added dropwise to 15 a solution of 9.03 g (45 mol) of 2-ethoxybenzamidine hydrochloride (example 13A) in 45 ml of ethanol. and the mixture is stirred at room temperature for 10 minutes. The ethanolic solution described above is added dropwise to this suspension, and the mixture is stirred at 70°C for 4 hours. The mixture is filtered, the solution is concentrated, the residue is partitioned between dichloromethane and water and the 20 organic phase is. after drying over sodium sulfate, concentrated. The residue is taken up in 60 ml of 1.2-dichloroethane. and 7.5 ml of phosphorus trichloride are added dropwise. After 2 hours of stimng under reflux, the mixture is cooled, diluted with dichloromethane and extracted twice with saturated sodium bicarbonate solution. The organic phase is dried and the solvent is removed under 25 reduced pressure. Chromatography with ethyl acetate and crystallization give 4.00 g (28.0% of theory) of a white solid. ]H-NMR (200MHz. CDC13): 1.02 (t. 3H). 1.56 (t. 3H). 1.89 (hex. 2H). 2.67 (s. 3H). 3.00 (t, 2H); 4.26 (quar, 2H), 7.05 (m. 2H), 7.50 (dt, IH), 8.17 (dd, IH), 10.00 (s, IH); TLC: Rr0.42 (dich]oromethane:methanol = 95:5). Example 17A 2-(2-Ethoxyphenyl)-5-ethyl-7-propyl-3H-imidazo[5,l-fJ[l,2,4]triazin-4-one 0 ,—CH, The preparation is carried out analogously to the procedure of example 16A using 29.06 g (167.8 mmol) of 2-butanoylaminobutyric acid (Example 2A) and 33.6 (167.8 mmol) of 2-ethoxybenzamidine hydrochloride (Example 13A). Purification is carried out by silica gel chromatography (mobile phase: CH2G2 / CH3OH 50:1). Yield: 7.4 g (12.4%) Rf = 0.46 (CH:C12 / CH?OH = 20:1) 'H-NMR (200 MHz. CDC13): 1.32 (tr 3H): 1.57 (t. 32H); 1.94 (m. 8H); 3.03 (quart, 2H); 3.64 (quhx IH): 4.27 (quart. 2H): 7.06 (d. IH): 7.12 (t, IH): 7.50 (du IH); 8.16 (dd, IH); 9.91 (s. IH). Example 18A 2-(2-Ethoxypheny])-5-methy]-7-(]-ethy]propyl)-3H-imidazo[5.1-fJ[h2,4]-triazin-4-one The preparation is carried out analogously to the procedure of example 16A using 21.45 g (0.1 mol) of 2-(2-etby])butyrylaminopropionic acid (example 3A) and 20.6 g (0.1 mol) of 2-etboxybenzamidine hydrochloride (example 13A). Purification is carried out by silica gel chromatography using the mobile phase dichloromethane/methanol 60:1. Yield: 7.22 g (21.3% of theory). 'H-NMR (200MHz: CDC13): 0.87 (t. 6H). 1.57 (t, 3H), 1.88 (m; 4H), 2.67 (s, 3H)T 3.28 (m. 1H). 4.28 (quar. 2H)r 7.05 (d. 1H). 7.13 (dt, 1H). 8.15 (dd5 1H). 10 15 Example 19A 2-(2-Ethoxypbeny]>5-methyl-7-(] J -dimethy]buty])-3H-irnidazo[5.] -f][l .2T4]triazii> 4-one O 20 The preparation is carried out analogously 10 the procedure of example 16A using 22.85 g (0.1 mol) of 2-(2.2-dimethyl)pentanoylaminopropionic acid (example 4A) and 20.6 g (0.1 mol) of 2-ethoxybenzamidine hydrochloride (example 13A). Purification is carried out by silica gel chromatography (mobile phase: CH1CI2 / CH?OH = 50:1). Yield: 6.56 g (18.5%) 'H-NMR (200 MHz; CD3OD): 0.82 (t. 3H); 1.1 (m, 2H); 1.45 (t, 3H); 1.5 (s, 6H): 1.95 (m, 2H); 2.57 (s; 3h); 4.2 (quar.r 2H); 7.1 (t, IH); 7.18 (d, IH); 7.52 (dt, IH); 7.72(dd,lH). Example 20A 2-(2-Ethoxyphenyl)-5-methyl-7-hexyl-3H-imida2o]5,l-f][l,2.4]triazin-4-one 10 The preparation is carried out analogously to the procedure of example 16A using 14.1 g (70 mmol) of 2-heptanoylaminopropionic acid (example 5A) and 14.05 g (70 mmol) of 2-etboxybenzamidine hydrochloride (example 13A). The purification of the product is cairied out by silica gel chromatography using the mobile phase petroleum ether / ethyl acetate 1:1. 15 Yield: 3.5 g (14.1%) 'H-NMR (CD?OD): 0.9 (t. 3H); 1.3 - 1.45 (m. 6H): 1.4 (t, 3H); 1.7-1.9 (m, 2H); 2.15 (sr 3H); 3.1 (t. 2H): 4.2 (quar.. 2H): 7.1 (t. IH): 7.15 (d, IH); 7.05 (td; IH); 7.7 (dd. IH). 20 Example 21A 2-(2-Ethoxypheny])-5-methyl-7-heptyl-3H-imdazo-[5.]-f|[1.2,4]triazin-4-one H,C O HN^^r^X .CH, The preparation is carried out analogously to the procedure of example 16A using 14.7 g (68.1 mmol) of 2-octanoylaminopropionic acid (example 6A) and 13.66 g (68.1 mmol) of 2-ethoxybenzamidine hydrochloride (example 13A). The purification of the product is carried out by silica gel chromatography using the mobile phase dichloromethane / methanol 50:1. Yield: 4.65 g (18.5%), oil 'H-NMR (CD3OD): 0.85 (t, 3H); 1.2-1.4 (m. 8H); 1.45 (t, 3H); 2.8 (quin, 2H); 2.6 (s, 3H); 3.0 (t 2H); 4.2 (quar, 2H); 7.1 (t, IH); 7.2 (d, IH); 7.55 (td, IH), 7.7 (dd, IH). Example 22A 2-(2-Ethoxyphenyl)-5-methyl-7-nonyl-3H-imidazo[5.]-fJ-[L2.4-]-triazin-4-one The preparation is carried out analogously to the procedure of example 16A using 17.0 g (70 mmol) of 2-decanoylaminopropionic acid (example 7A) and 14,05 g (70 mmol) of 2-ethoxybenzamidine hydrochloride (example 13A). The purification of the product is carried out by silica gel chromatography using the mobile phase petroleum ether / ethyl acetate 1:1. Yield: 3.5 g (14.1%) 'H-NMR (CD3OD): 0.9 (t. 3H): 1.3 - 1.45 (m. 6H): 1.4 (t, 3H); 1.7-1.9 (m, 2H): 2.15 (s, 3H): 3.1 (t. 2H): 4.2 (quar.. 2H); 7.1 (t. IH): 7.15 (d, IH); 7.05 (td. IH), 7.7 (dd, IH). Example 23 A 2-(2-Ethoxypheny])o-metby]-7-(2-ethy]hepTy])-3H'imida2o[5.]-f][].2,4]-ina2jn-4- one 10 The preparation is carried out analogously to the procedure of example 16A using 10.95 g (45 mmol) of 2-(2-ethyl)octanoylaminopropionic acid (example 8A) and 9.03 g (45 mmol) of 2-ethoxybenzamidine hydrochloride (example 13A). Purification is carried out by silica gel chromatography using cyclohexane/ethyl acetate. Yield: 7.22 g (21.3% of theory) 'H-NMR (200MHz. CDC13): 0.75-0.90 (m. 6H)T 1.10-1.40 (m. 8H), 1.50 (t, 3H). 1.80-2.05 (m. 4H). 2.70 (s. 3H); 3.40 (quin.. 1H). 4.30 (t, 2H)r 7.05-7.20 (pseudo quar. 2H): 7.50 (id. lH)r 8.20 (dd, 1H). 10.40 (s. 1H). 15 Example 24A 2-(2-Propoxyphenyl)-5-methy]-7-(2-ethylhepty])-3H-imidazo[5r]-fj[]r2,4]triazin-4-one 20 The preparation is carried out analogously to the procedure of example 16A using 10.95 g (45 mmol of 2-(2-ethyl)octanoylaminopropionic acid (example 8A) and 9.66 g (45 mmol) of 2-propoxybenzamidine hydrochloride (example 13A). Purification of the product is earned out by silica gel chromatography using the mobile phase dichloromethane / methanol 60:1. Yield: 3.7 g (20%), yellow oil 'H-NMR (CDC13): 0.75 - 0.9 (m, 6H); 1.15 (t, 3h); 1.1 - 1.35 (m, 8H); 1.75 - 2.1 (m, 6h): 2.7 (s, 3H); 3.4 (quin, 1H); 4.2 (t, 2H); 7.05 - 7.2 (pseudo quar, 2H); 7.5 (td, 1H): 8.2 (dd, 1H); 10.2 (broad, 1H). Example 25A 2-(2-Ethoxyphenyl)-5-methyl-7-cyclopentyl-3H-imidazo[5J-f)[L2,4]-triazin-4-one O 15 The preparation is carried out analogously to the procedure of example 16A using ]9.9g (lOOmmol) of 2-cyclopentanoylaminopropionic acid (example 9A) and 20 g (lOOmmol) of ethoxybenzamidine hydrochloride (example 13A). Purification is carried out by silica gel chromatography using methylene chloride/methanol 50:1. Yield: 7.1 g (20.9%) ]H-NMR (200 MHz. CD3OD): .45 (t. 3H): ] .65 - 1.80 (m. 2H); 1.80 - 2.00 (m, 4H): 2.05 - 2.20 (m, 2H); 2.60 (s. 3H); 3.65 (quin.. IH); 4.20 (quar., 2H); 7.10 (t, 1H): 7.15 (d, 1H); 7.50 (t. 1H); 7.70 (d, 1H). 20 Example 26A 2-(2-Propoxyphenyl)-5-methy]-7-cyclopenty]-3H-imidazo[5.]-f]f],2.4]-triazin-4-one The preparation is carried out analogously to the procedure of example 16A using 8.33 g (45.0 mmol) of 2-cyclopentanoylaminopropionic acid (example 9A) and 9.65 g (45.0 mmol) of 2-propoxybenzamidine hydrochloride (example 15A). Purification is carried out by silica gel chromatography using the mobile phase dichloromethane/methanol 50:1. The product can be crystallized from ethyl acetate/petroleum ether. Yield: 1.82 g (11.5% of theory) white solid. 'H-NMR (200MHZ. CDC13): 1.15 (t. 3H)r 1.70 (m. 2H)r 1.95 (m. 4H), 2.15 (m; 2H)r 2.65 (s. 3H): 3.65 (quin.: 1H). 4.15 (tr 2H): 7.05 (d. 1H). 7.10 (t, 1H). 7.50 (td, 1H). 8.20(dd, 1H). Example 27A 2-(2-Ethoxypheny])-5-ethyl-7-cyclopenty]-3H-imidazo[5.1-f][].2,4]triazin-4-one O /—CH3 The preparation is carried out analogously to the procedure of example 16A using 8.33 g (45.0 mmol) of 2-cyclopentanoylaminopropionic acid (example 9A) and 9.65 g (45.0 mmol) of 2-propoxybenzamidine hydrochloride (example 15A). Purification is carried out by silica gel chromatography using the mobile phase dichloromethane/methanol 50:1. The product can be crystallized from ethyl acetate/petroleum ether. Yield: 1.82 g (] 1.5% of theory) white solid. 'H-NMR (200MHz. CDC13): 1.15 (t, 3H)f 1.70 (m. 2H)r 1.95 (m. 4H), 2.15 (m. 2H). 2.65 (s. 3H). 3.65 (quin.: ]H)r 4.15 (l 2H). 7.05 (d. 1H). 7.10 (t. 1H). 7.50 (td: 1H). 8.20(dd,lH). Example 27A 2-(2-Ethoxyphenyl)-5-ethy]-7-cvclopentyl-3H-imidazo[5.1-f][1.2.4]triazin-4-one " ' 1 rCH- HX O HN' The preparation is carried out analogously to the procedure of example 16A using 8.77 g (44 mmol) of 2-cyclopemanoylaminobutyric acid (example 10A) and 8.83 g (44 mmol) of 2-ethoxybenzamidine hydrochloride (example 13A). The product is purified by silica gel chromatography using the mobile phase cyclohexane/ethyl acetate (6:4). Yield: 0.355 g (6.7%). white solid 'H-NMR (CDCI3): 1.32 (t. 3H); 1.57 (t, 3H); 1.94 (m, 8H); 3.03 (quar, 2H); 3.64 (quin, 1H); 4.27 (quarr 2H), 7.06 8d, 1H); 7.12 (t, 1H); 7.50 (t, 1H); 8.16 (dd, 1H): 9.91 (s, 1H). Example 28A 2-(2-Ethoxyphenyl)-5-methy]-7-cycloheptyl-3H-imidazo[55l-fJ[1.2,4]-triazin-4-one The preparation is carried out analogously to the procedure of example 16A using 10 14.9 g (70 mmol) of 2-cyclohepianoylaminopropionic acid (example 11A) and 14 g (70 mmol) of 2-ethoxybenzamidine hydrochloride (example 13). Purification of the product is carried out by silica gel chromatography using the mobile phase methylene chloride / methanol 10:1. then 50:1. Yield: 5.35 g (20.9%) 15 'H-NMR (CD3OD): 1.45 (t, 3H); 1.6 - 2.0 (m: 10H): 2.1 - 2.2 (m. 2H); 2.7 (s? 3H): 3.65 (quin.. 1H); 4.2 (quar.. 2H); 7.1 (t: 1H): 7.2 (d. 1H): 7.6 (tdf 1H); 7.75 (dd, 1H). Example 29A 20 2-(2-Ethoxypheny])-5-ethy]-7-cyclohepty]-3H-imidazof5.1-f|[3.2.4]-triazin-4-one CH, O ^,CK j MINI yz^y N The preparation is carried out analogously to the procedure of example 16A using 1.02 g (4.5 mmol) of 2-cycloheptanoylaminobutyric acid (example 12A) and 0.98 g (4.9 mmol) of 2-ethoxybenzamidine hydrochloride (example 13A). Purification is carried out by silica gel chromatography using ethyl acetate / cyclohexane 1:1. Yield: 0.391 mg(14%) !H-NMR (200 MHz; D6-DMSO): 8 = 1.21 (t: 3H, CH3), 1.30 (1, 3H; CH3), 1.40 -2.01 (m, 12H5 CH2), 2.86 (g; 2H. CH2), 3.32 (m, 1H: CH), 4.10 (g, 2H, CH2)r 7.05 (t, 1H); 7.15 (d, 1H), 7.51 (m, 2H), 11.50 (bs5 1H5 NH). Example 30A 4-Benzyloxy-2-bromophenol 183 g of 4-benzyloxyphenol (914 mmol) are brominaied according to the literature (.l.C.S Perkin 1. 1981. 2123). Following recrvstallizaiion from petroleum ether (with 5% ether), the product is obtained as a colorless solid. Yield: 189 g (74.1% of theory) MS (DC1, NH3): m/z (%) = 296/298 (M+18) (100) 'H-NMR (200 MHzr CDC13): 6 = 4.96 (s, 2 H); 5.19 (s. 1H); 6.70-6.95 (m, 2 H): 7.10 (d, 1 H); 7.39-7.45 (m. 5 H). Example 31A 5-Benzyloxy-2-ethoxybrombenzene H3CT O 10 186.18 g of 4-benzyloxy-2-bromophenol (667 mmol) (example 30A) and potassium carbonate (276.56 g. 2 mol) are initially charged in 2 1 of acetone. 74.7 ml of bromoethane (1 mol) are added dropwise, and the mixture is stirred at reflux for 24 h. The mixture is filtered off and concentrated. The resulting oily residue is dissolved in 1200 ml of ethanol. With vigorous stirring, the product is crystallized by slowly adding 900 ml of water. The product is filtered off with suction and the light-beige crystals are dried under high vacuum. Yield 178.9 g (95.1% of theory) MS (DC1. NH3): m/z (%) = 326/328 (M+18) (100) 'H-NMR (200 MHzr CDC13): 6 = 1.45 (t. 3 H); 4.05 (qr 2 H); 4.98 (s, 2 H). 6.79-6.90 (m. 2 H); 7.18-7.46 (m. 6 H). 15 Example 32A 5-BenzYloxy-2-ethoxvbenzonitrile 20 178.17 g of 5-benzyloxy-2-etboxybromobenzene (580 mmol) (example 31 A) are added to 57.14 g of copper cyanide (638 mmol). and the two components are mixed by shaking. Following addition of 65 ml of dry pyridine, the mixture is heated to 160°C. The mixture melts and forms a homogeneous solution. The solution is stirred at 160°C for 6 h. After cooling to about 100°C. toluene is added and the mixture is stirred until the reaction mixture has cooled. The mixture is filtered through kieselguhr, and the kieselguhr is washed repeatedly with toluene. The filtrate is then washed with dilute ammonia solution until the aqueous phase is no longer blue. The mixture is washed with saturated sodium chloride solution, dried and concentrated. 5 The resulting residue is recrystallized from 500 ml of ethanol, complete crystallization is achieved by addition of 100 ml of water. The crystals are filtered off with suction and washed repeatedly with petroleum ether. The brownish crystals are dried at 45°C under reduced pressure. Yield 140.4 g (92.5% of theory) 10 MS (DCI, NH3): m/z (%): 271 (M+18) (100) 'H-NMR (200 MHz, CDC13): 8 = 1.45 (t, 3 H). 4.08 (q, 2 H); 5.01 (s, 2 H); 6.85-6.90 (1 H); 7.10-7.18 (2 H), 7.31-7.42 (m, 5 H). 15 Example 33A 3-Benzvloxv-6-ethoxvbenzamidine hydrochloride 46.46 g of ammonium chloride (868.5 mol) are suspended in 650 ml of toluene, and the mixture is cooled to 0-5°C. Trimethylaluminum is added dropwise as a 2M 20 solution in hexane (445 ml, 888.3 mmol). and the mixture is then stirred at room temperature until the evolution of gas has ceased. 5-Benzyloxy-2-ethoxybenzonitrile (3 00 g, 394.8 mmol) (example 32A) is added, and the mixture is stirred at 80°C overnight. The cooled reaction mixture is, with ice-cooling, added to a suspension of 200 g of silica gel and 2 1 of dichloromethane. and the mixture is stirred for 30 min. 25 The mixture is filtered off with suction and the filter cake is washed with methanol. The organic phases are combined and concentrated. The resulting residue is triturated using a mixture of dichloromethane/methanol 9:1. filtered and concentrated using a rotary evaporator. The residue is then triturated with ether, and the colorless solid is filtered off with suction. Yield 59.4 g (49% of theory) ]H-NMR (300 MHz; D6-DMSO): 6 = 1.32 (t 3 H); 4.09 (q, 2 H); 5.15 (s, 2 H); 7.10- 7.49 (m, 8 H); 9.1-9.5 (m, 3). 10 Example 34A 2-[5-(benzyloxy)-2-ethoxypheny]]-7-cyclopentyl-5-methy]-3H-imidazo[5.1-f][1.2.4]triazin-4-one 4.07 g of 2-cyclopentanoylaminopropionic acid (22 mmol) (example 9A) are initially charged in 22 ml of dry tetrahydrofuran and 5.3 ml of pyridine (66 mmol). 0.13 g of 15 4-DMAP are added and the mixture is is heated under reflux. Ethyl oxaJyl chloride (6.7 ml. 44 mmol) is slowly added dropwise, and the resulting suspension is heated under reflux for two hours and then, after cooling, diluted with ethyl acetate and filtered, and the aqueous phase is washed with IN hydrochloric acid (2x). saturated sodium bicarbonate solution (2x) and saturated sodium chloride solution, dried over 20 sodium sulfate and concentrated. After drying under high vacuum, a yellow oil is obtained which is. dissolved in 13 ml of ethanol. added to a solution which is prepared as follows: 3.37 Q of 3-benzy]oxy-6-ethoxybenzamidme hydrochloride (11 mmol) (example 33A) are initially charged in 13 ml of ethanol. the mixture is cooled to 0°C and 1.13 g of hydrazine hydrate (16.5 mmol) are added dropwise. The mixture is warmed to ~ 40°C and stirred for 10 min. After the ethanolic solution has been added, the mixture is stirred at 70°C for 3.5 h. 5 The mixture is concentrated and dried under high vacuum, and the yellow foam is dissolved in 100 ml of 1,2-dichloroefhane. 2 ml of phosphorus oxychloride are added and the mixture is heated at reflux for 1.5 h. After cooling, the mixture is diluted with dichloromethane and washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried with magnesium 10 sulfate and concentrated. The dark residue is taken up in ethyl acetate, and after addition of petroleum ether precipitation occurs. The mixture is filtered off and the filtrate is then concentrated and the residue is chromatographed (cyclohexane/ethyl acetate 3:2). The product is recrystallized from ethyl acetate/petroleum ether. Yield 632 mg (12.9% of theory) 15 MS(DCLNH3):m/z(%)= 445 (M+H) (100) 'H-NMR (200 MHz. CDC13): 8 = 1.55 (t, 3 H); 1.20-2.21 (m. 8 H); 2.55 (s, 3 H); 3.61 (qui, 1 H): 4.21 (q. 2 H); 5.12 (s. 2 H); 6.98 (d. 1 H): 7.11 (dd, 1 H): 7.32-7.50 (m. 5H);7.78(d, 1 H); 10.10 (s, 1 H). 20 Example 35A 611 mg of the compound from example 34A (1.37 mmol) are suspended in 13 ml of ethanol. 13 ml of ether and a few drops of acetic acid are added (dissolution 25 incomplete). Under an atmosphere of argon. 200 mg of 10 % Pd/C are added to the suspension and the suspension is repeatedly flushed with hydrogen, then stirred vigorously under an H2 atmosphere (1 aim) for 2 h and finally filtered off through Celite. The filtrate is concentrated and dried under high vacuum and the residue is treated with ether/petroleum ether, filtered and dried under high vacuum. Yield 395 mg (81.5% of theory) MS (DCh NH3): m/z (%) = 355 (M+H) (100) Example 36A Ethoxy-5-hydroxybenzonitrile 10 40.02 g of 5-benzyloxy-2-ethoxybenzonitrile (158 mmol) (example 32A) and 5% Pd/C (4.0 g) are initially charged in 1 1 of methanol. The mixture is then hydrogenated under an atmosphere of hydrogen (1 atm) for about 4 h. The mixture is filtered through kieselguhr and evaporated and the crystalline residue is dried under reduced pressure. 15 Yield 25.5 g (99.6% of theory) 'H-NMR (200 MHz. CDC13): 8 - 1.43 (t. 3 H); 4.05 (q. 2 H). 6.75-6.88 (m, 1 H); 7.0-7.07 (mr 2 H). 20 Example 37A 5-Allyloxy-2-ethoxybenzonitrile H,C 25 g of 2-ethoxy-5-hydroxybenzoniirile (153.2 mmol) (example 36A) and potassium carbonate (63.52 g, 459.6 mmol) are initially charged in 750 ml of acetone. 19.9 ml of ally] bromide (229.8 mmol) are added, and the mixture is stirred under reflux overnight. The mixture is filtered off and concentrated giving a mobile orange oil. Yield 31 g (99.6% of theory) 'H-NMR (200 MHz, D6-DMSO): 5 = 1.45 (t, 3 H); 4.10 (q, 2 H); 5.28-5.95 (m, 2 H); 5.92-6.1 l.m 1 H); 6.85-6.92 (m, 1 H); 7.06-7.13 (m, 2 H). Example 38A 10 3-AUyloxy-6-efhoxybenzamidine hydrochloride 17.95 g of ammonium chloride (335.56 mmol) are suspended in toluene and cooled to 0-5°C. Trimethylaluminum (2M solution in hexane, 172 ml. 343.2 mmol) are 15 added dropwise. and the mixture is then stirred at room temperature until the evolution of gas has ceased. 5-Allyloxy-2-ethoxybenzonitrile (31 g, 152.5 mmol) (example 37A) is then added and the mixture is stirred at 80°C overnight. The cooled mixture is then added to a mixture of 100 g of silica gel and 1 1 of dichloromethane and stirred for 30 min. The mixture is filtered off with suction, the filter cake is 20 washed twice with methanol and the filtrate is concentrated. The residue that is obtained is stirred with dichloromethane/methanol 9:1. filtered off and concentrated using a rotary evaporator. The residue consists of a red-brownish semicrystalline material. Using acetone, 10 g of a colorless solid are obtained after filtration. The mother liquor gives, after concentration using a rotary evaporator, 21 g of a viscous 25 reddish oil which is dissolved in a little dichloromethane. The solution is seeded with a little product and allowed to stand overnight. Filtration with suction and washinp with a little acetone gives a further 6 g of solid. Yield 16 g (38.6% of theory) MS (DCI, NH3): m/z (%) = 221 (M-Cl) (100) 'H-NMR (200 MHz, D6-DMSO): 5 = 1.32 (t, 3 H); 4.08 (q, 2 H); 4.60 (d, 2 H); 5.35- 5.97 (m,2H); 5.94-6.15 (m, 1 H); 7.13-7.22 (m, 3 H); 9.2/9.35 (2x s, in total 4 H). Example 39A 2-[5-(A]]y]oxy)-2-ethoxypheny]]-7-cyclopentyl-5-methy]-3H-imidazo[5,l-fJ[1.2,4]triazin-4-one 'CH2 14 .82 g of 2-cycloentanoylaminopropionic acid (example 9A) (80 mmol) are initially charged in 80 ml of dry tetrahydrofuran and 19.4 ml of pyridine (240 mmol). 0.49 g of 4-DMAP is added and the mixture is is heated under reflux. Ethyl oxalyl chloride (17.9 ml. 160 mmol) is slowly added dropwise. and the resulting suspension is heated under reflux for two hours. The mixture is poured into ice-water and extracted three times with ethyl acetate. The extracts are dried and concentrated. The resulting oily residue is taken up in methanol, sodium bicarbonate is added and the mixture is boiled for 2.5 hours. After cooling, the mixture is filtered. The filtrate is added to a solution which was prepared as follows: 15 g of 3-allyloxy-6-ethoxybenzamidine hydrochloride (58.4 mmol) (example 38A) are initially charged in ethanol with ice-cooling. Over a period of lOmin, hydrazine hydrage (3.07 g. 61.3 mmol) is added dropwise. and the mixture is then stirred at room temperature for another 30 min. After 4 h at 70°C. the mixture is concentrated and the residue is taken up in 80 ml of 1.2-dichloroethane. mixed with 10 ml of phosphorus oxychloride and stirred under reflux for 1 h. The mixture is diluted with dichloromethane and neutralized usins sodium bicarbonate. The mixture is once more washed with water and then dried and concentrated using a rotary evaporator. The crude product is pre-purified by silica gel flash chromatography using cyclohexane/ethyl acetate 1:1. The resulting oily residue is crystallized using ether. Another crystallization from cyclohexane/ethyl acetate 1:1 5 gives 3.34 g of a solid. The mother liquor is concentrated using a rotary evaporator and chromatographed using dichloromethane/acetone 95:5. This gives a further 2.9 g of product. Yield 6.24 g (27.1% of theory) MS (DCL NH3): m/z (%) = 395 (M+H) (100) 10 'H-NMR (200 MHzr CDC13): 8 = 1.56 (t 3 H); 1.69-2.21 (m, 8 H); 2.65 (s, 3 H); 3.65 (qui. 1 H); 4.21 (q, 2 H); 4.59 (dd. 2 H); 5.30-5.51 (m, 2 H); 5.99-6.28 (m, 1 H); 6.95-7.09 (mr 2 H); 7.75 (d, 1 H); 10.10 (s, 1 H). 15 Example 40A 7-Cyc]openty]-2-[2-ethoxy-5-(2-oxirany]methoxy)phenyl]-5-methyl-3H-imidazo[5.1' fJ[].2.4]triazin-4-one 0 TH X H,C ^O HN 4.26 g (10.8 mmol) of the compound from example 39A are dissolved in 20 dichloromethane. Meta-chloroperbenzoic acid (7.64 g. technical grade, about 50%. 22.1 mmol) is added, and the mixture is stirred at room temperature for 7 h. The mixture is filtered, the filter cake is washed with dichloromethane and the filtrate is then washed with thiosulfrte solution and 3 times with sodium bicarbonate solution, dried and concentrated. Flash chromatography using ethyl acetate/cyclohexane 6:4 25 gives 1.6 g of the starting material LMP 45-1 and 460 mg of product. 10 62.9 mg (0.119 mmol) of the compound from example 19 are dissolved in 5 ml of dichloromethane and filtered through a small glass frit, and the filter residue is washed with 1 ml of dichloromethane. 1 ml of 1M HC1 in ether is added dropwise to the filtrate, giving a somewhat sticky precipitate which crystallizes after further stirring and scratching. After 15 minutes of stirring in 15 ml of ether, the crystalline product is filtered off with suction, washed with ether and dried under high vacuum. Yield: 36.3 mg (50.2% of theory). MS (ESI): 530 (M+H) for the free base, HPLC (analvtic): 97.4% RT: 4.70 min, column: Nucleosil CI 8 (125X4mm), mobile phase: 0.01m H3PO4/ acetonitrile (gradient), flow rate:2 ml/min, 200-400 ran. 15 Example 21 2-[5-(2,5-Dichlorothiophene-3-sulfonamido)-2-propoxyphenyl]'5-methy]-7-cyc]openty]-3H-imidazo [5,l-f][3,2,4]-triazin-4-one O 20 150 mg (0.408 mmol) of the compound from example 44A are reacted with 308 mg (1.224 mmol) of 2.5-dichlorothiophene-3-sulfonyl chloride and 0.33 ml (4.08 mmol) of pyridine in letrahydrofuran for 4 hours. Yield: 66.1 mg (27.8% of theory)- 'H NMR (300 MHz. DMSO): 0.93 (t. 3H). 1.58-2.10 (m. 10H), 2.45 (s. 3H), 3.47 (quin.. 1H). 3.97 (t. 2H), 7.12 (d. 1H). 7.22-7.31 (m. 3H). 10.57 (s, 1H), 11.48 (s, 1H): MS (ESI): 582 (M+H). 25 Example 22 2-[2-Propoxy-5-(4.4.4-trifluoro-]-butanesu]foT]y]amirio)pheny]]-5-methy]-7-cyc]opentyl-3H-imidazo[5.1-f][1.2.4]-triazin-4-one 5 150 mg (0.408 mraol) of the compound from example 44A are reacted with 183 mg (0.87 mmol) of 4.4.4-trifluoro-l-bmanesulfonyl chloride and 484 mg (6.12 mmol) of pyridine in 8 ml of tetrahydrofuran for 3 hours. Yield: 33.5 mg (15.2% of theory). MS (DCI/NH3): 542 (M+H) 10 HPLC (analytic): 97.5% RT: 6.99 mm. column: Nucleosil CI 8 (125X4mm)T mobile phase: 0.01m H3PO4 / acetonitrile (gradient), flow rate:2 ml/min. 200-400 ran; TLC: R,=0.64 (toluene:ethyl acetate = 2:8). 15 Example 23 2-[5*(3-Cyanobenzenesulfonamido)-2-propoxyphenyl]-5-methy]-7-cyclopentyl-3H-imidazo[5.1-f][1.2.4]-triazin-4-one 200 mg (0.566 mmol) of the compound from example 44A are reaccted with 342 mg (1.70 mmol) of 3-cyanobenzenesulfonyl chloride and 0.46 ml (5.66 mmol) of pyridine in 15 ml of tetrahydrofuran overnight. Yield: 58.8 mg (19.5% of theory). 5 !H-NMR (200 MHz, DMSO): 0.90 (t, 3H), 1.55-2.08 (m, 10H), 2.45 (s, 3H), 3.42 (quin., 1H), 3.93 (t, 2H), 7.06-7.28 (m, 3H), 7.82 (quar, 1H), 8.00 (d, 1H)5 8.12 (d, 2H), 10.38 (s, 1H), 11.42 (s, 1H); MS (ESI): 533 (M+H). 10 Example 24 2-[5-(y-Morpbolinopropanesu]fonylamino)-2-propoxy-phenyl]-5-methyl-7-cyclopentyl-3H-imidazo[5,l-f][l,2.4]-triazin-4-one 15 100 mg (0.272 mmol) of the compound from example 44A are reacted with 250 mg (1.09 mmol) of y-morpholinopropanesulfonyl chloride and 0.22 ml (2.73 mmol) of pyridine in 5 ml of tetrahydrofuran overnight. Yield: 137 mg (90.0% of theory). MS (DCI/NH3): 559 (M+H)r 20 HPLC (analytic): 90.0% RT: 4.68 min. column: Nucleosil CI8 (125X4mm), mobile phase: 0.01m H?P04/ acetonitrile (gradient), flow rate:2 ml/min. 200-400 nm: TLC: R(=0.28 (ethyl acetate:methanol = 9:1). Example 25 2-[5-(N.N-Bismethylsulfonyl)amino-2-propoxy-phenyl]-5-methyl-7-cyclopentyl-3H-imidazo[5,]-f][l,2,4]-triazin-4-one 37.9 mg (0.38 mmol) of triethylamine and 42.9 mg (0.38 mmol) of methanesulfonyl chloride are added successively to 55.1 mg (0.15 mmol) of the amino compound from example 44A in 5ml of tetrahydrofuran. and the mixture is stirred at room temperature for 1 hour. The reaction solution is concentrated, the residue is partitioned between water and ethyl acetate and the organic phase is separated off. dried and concentrated. The residue is chromaiographed on 30 ml of silica gel using dichloromethane and methanol in a gradient system. Yield: 51.7 mg (77.4% of theory). MS (ESI): 524 (M+H); TLC: RrO.52 (toluene:ethyl acetate = 6:4). 5.8 mg (8.7% of theoiy) of the monomesyl derivative = example 13 are isolated as a by-product. The following compounds (example 26 to example 35) are prepared analogously to the procedure of example 25: Example 26 2-[5-(N.N-Bisisopropylsulfonyl)amino-2-propoxyphenyl]-5-methyl-7-cyclopentyK 3H-imidazo[5,l-f][l,2,4]-triazin-4-one 10 150 mg (0.408 mmol) of the compound from example 44A are reacted with 116 mg (0.816 mmol) of 2-propanesulfonyl chloride and 0.12 ml (0.857 mmol) of triethylamine in 15 ml of tetrahydrofuran for 1 hour. Yield: 41.0 mg (17.4% of theory). MS (ESI): 580 (M+H). HPLC (analytic): 98.9% RT: 7.91 min. column: Kromasil (]25X2mm). mobile phase: 0.01m H?PO„ / acetonitrile (gradient), flow rate:2 ml/min. 200-400 nm: TLC: Rf=0.40 (toluene:ethyl acetate -1:1). Example 27 15 2-(5-lsopropylsulfonylamino-2-propoxyphenyl)-5-methyl-7-cyclopentyl-3H-imidazo [5;]-f][L2,4]-triazin-4-one In example 26, 11.4 mg (5.90% of theory) of the monoisopropyl derivative are isolated as a "by-product. MS (ESI): 474 (M+H)T TLC: Rf=0.35 (toluene:ethyl acetate = 1:1). Example 28 2-{2-Propoxy-5-[2-(2.2.2-trifluoro-l-trifluoromethy]ethoxy)ethanesulfonylamino]-phenyl}-5-methyl-7-cyclopentyl-3H-imidazo[5J-f][l,254]-tria2in-4-one 150 mg (0.408 mmol) of the compound from example 44A are reacted with 180 mg (0.612 mmol) of 2-(2.2.2-trifluoro-]-trifluoromethy]ethoxy)ethanesu]fony] chloride and 0.085 ml (0.612 mmol) of triethylamine for 1 hour. Yield: 77.0 mg (30.2% of theory). 'H-NMR (200 MHz. DMSO): 0.93 (t. 3H). 1.53-2.07 (mr 10H), 2.47 (s, 3H)r 3.42 (quin., 1H). 3.97 (t. 2H). 4.20 (t, 2H), 5.60 (quin.. 1H); 7.17 (d, 1H), 7.37 (ddr 2H). 9.88 (bsJH), 11.50 (bs;1H): MS (DCI/NH3): 626 (M+H). Example 29 2-(2-Propoxy-5-vinylsu]fonylaminophenyl)"5-methyl-7-cyclopenty]-3H-imida2o[5J-f][l,2,4]-triazin-4-one 10 During the preparation of example 28. the vinylsulfonylamido derivative is formed as a by-product. Yield: 64.5 mg (25.3% of theory). 'H-NMR (200 MHz. DMSO): 0.92 (t; 3H): 1.52-2.08 (m. 10H), 2.43 (s, 3H). 3.47 (quint.. IH). 3.97 (t. 2H)r 6.03 (dd. 2H). 6.79 (dd. IH). 7.13 (d. IH). 7.27 (d. 1H); 7.37 (m. 1 H)r 9.97 (bs. 1 H): 11.45 (bs. 1H); MS (DCI/NH3): 458 (M+H). Example 30 15 2-[2-Propoxy-5-(4.4.5.5.5-pentafluoropentanesulfonylamino)phenyl]-5-methyl-7- cyclopentyl-3H-imidazo[5.1-f)[1.2.4]-triazin-4-one 150 mg (0.408 mmol) of the compound from example 44A are treated with 160 mg (0.612 mmol) of 4.4.5,5,5-pentafluoropentanesulfonyl chloride and 62 mg (0.612 mmol) of tri ethyl amine in 8 ml of tetrahydrofuran for 1 hour. Yield: 171 mg (70.9% of theory). 'H-NMR (200 MHz, DMSO): 0.93 (t. 3H), 1.53-2.09 (m, 12H), 2.23-2.42 (m, 2H), 2.47 (s, 3H), 3.22 (t, 2H), 3.47 (quin., IH), 3.97 (t. 2H), 7.17 (d, IH), 7.37 (dd, 2H), 9.83 (s, IH), 11.48 (s, IH); MS (DCI/NH3): 592 (M+H). Example 31 2-[5-Bis(N.N-4.4,5,5,5-pemafluoropemanesu]fony])amino-2-propoxypheny]]-5-methyl-7-cyc)openty]-3H-imidazo[5.]-f)[].2,4]-triazin-4-one In example 30. 10.2 mg (4.20% of theory) of the bis derivative are isolated as a by¬product. MS (ESI): 816 (M+H). TLC: R,=0.74 (ioluene:ethy] acetate:fonnic acid = 2:7.5:0.5). Example 32 2-[5-Bis(N.N-4.4.4-trifluoro-l-butanesu]fonyl)amino-2-propoxyphenyl]-5-methyl-7-cyclopenty]-3H-imidazo[5,l-f][l,2,4]-triazin-4-one F F 150 mg (0.408 mmol) of the compound from example 44A are reacted with 529 mg (2.512 mmol) of 4,4.4-trifJuoro-l-butanesulfonyl chloride and 0.49 ml (3.516 mmol) of triethylamine in 12 ml of tetrahydrofuran for 5 hours. Yield: 194 mg (66.8% of theory). 'H-NMR (200 MHz. DMSO): 0.95 (t. 3H). 1.53-2.15 (m. 18H), 2.47 (s. 3H), 3.50 (quin.. 1H). 3.80 (t.4H). 4.08 (t.2H). 7.28 (d. 1H). 7.62 (m. 2H). 11.62 (s. 1H): MS(ESI):716(M+H). Example 33 2-[5-Bis(N.N-3-trif]uoromethylbenzenesulfonYl)amino-2-propoxyphenyl]-5-methyl-7-cyc]opentyl-3H-imidazo[5.1-f][1.2,4]-triazin-4-one 10 150 mg (0.408 mmol) of the compound from example 44A are reacted with 399 mg (1.632 mmol) of 3-(trifluoromethyl)benzenesulfonyl chloride and 0.239 ml (1.714 mmol) of pyridine in 8 ml of tetrahydrofuran for 3 hours. Yield: 169 mg (52.8% d.Th.). 'H-NMR (200 MHz; DMSO): 0.95 (t, 3H)T 1.57-2.00 (m. 10H)? 2.47 (s, 3H), 3.42 (m. 1H)T 4.07 (t. 2H). 7.22 (s. 1H)S 7.27 (s. 2H). 7.97 (ir 2H)T 8.07 (s, 2H). 8.17 (dr 2H). 8.27 (d.2H): 11.57 (s. 1H); MS (ESI): 784 (M+H). Example 34 2-(2-Propoxy-5-propanesulfonylaminopbeny])-5-methyl-7-cyclopenty]-3H-imidazo[5.3-f)[],2,4]-triazin-4-one 150 mg (0.408 mmol) of the compound from example 44A are treated with 116 mg (0.816 mmol) of 1 -propanesulfonyl chloride and 87 mg (0.816 mmol) of triethylamine in 15 ml of tetrahydrofuran for 1 hour. Yield: 72.6 mg (37.6% of theory). 'H-NMR (300 MHz, DMSO): 0.94 (quar, 6H), 1.58-2.05 (m, 12H), 2.48 (s, 3H), 3.02 (m, 2H), 3.45 (quin., IH), 3.98 (t, 2H), 7.13 (d, IH), 7.34 (dd, IH), 7.40 (d, IH), 9.63 (s, IH), 11.40 (s, IH); MS (ESI): 474 (M+H). Example 35 2-[5-Bis(N,N-propanesu]fony])amino-2-propoxyphenyl]-5-methyl-7-cyclopentyl-3H-imidazo[5,]-fj[l,2.4]-triazin-4-one o°°o In example 34, 73.3 mg (31.0% of theory) of the bis derivative are isolated as a by¬product. 'H-NMR (300 MHz. DMSO): 1.00 (tl, 9H)S 1.59-2.04 (m. 14H), 2.48 (s, 3H), 3.48 (quin.. 1H). 3.64 (t. 4H). 4.07 (t. 2H). 7.23 (d, 1H). 7.62 (m. 2H), 11.56 (s, 1H): MS (ESI): 580 (M+H). Example 36 2-f2-Elhoxy-5-C4-ethy]pjperazin-]-y]-su]fony]amino)pheny]]-5-methy]-7-propy]-3H-imidazo[5.1-fj[1.2,4]-triazin-4-one Under argon. 400 mg (1.22 mmol) of the amino compound from example 46A in 19.3 g (244 mmol) of pyridine are reacted with 1.22 g (4.89 mmol) of 4-ethyl-l-piperazinesulfonyl chloride hydrochloride at room temperature for 16 hours. The solution is then concentrated and the residue is taken up in toluene and re-concentrated. The residue is then partitioned between 170 ml of dichloromethane. 10 ml of NaHCC>3 solution and 5 ml of water, the organic layer is separated off, the aqueous layer is washed twice with dichloromethane and the organic phase is dried and concentrated. Purification of the crude product is carried out by chromatography on 140 ml of silica gel using ethyl acetate with acetone added in increasing proportions of from 11 % to 43%. Yield: 394 mg (64.0% of theory). TLC: Rf=0.48 (acetone). Formation of the hydrochloride: 383 mg (0.76 mmol) of the free base are dissolved in 2 ml of dichloromethane and stirred with 2 ml of 1 M HC1 in ether. 15 ml of ether are then added and the mixture is stiired for 20 minutes, resulting in the precipitation of a solid materia] which is filtered off with suction, washed with 15 ml of ether and dried under reduced pressure. Yield: 235 mg (51.1% of theory). 'H-NMR (200 MHz. DMSO): 0.95 (t. 3H)r 1.24 (m. 6H). 1.80 (hex, 2H). 2.58 (s. 3H). 2.83-3.90 (mm. 12H); 4.08 (quar.. 2H): 7.18 (d. 1H). 7.39 (d. 1H). 7.42 (s. 1H). 10.15 (s.lHX 12.02 (s.lH): MS (ESI): 504 (M+H). Example 37 2-[2-Ethoxy-5-(morpholinylsulfonamido)pheny]]-5-rnethyl-7-propy]-3H-imidazo[5.1-f][1.2,4]-triazin-4-one O 10 Analogously to the procedure of example 36. 150 mg (0.458 mmol) of the amino compound from example 46A are reacted with 680 mg (3.67 mmol) of morpholine N-sulfonyl chloride in 7.4 ml of pyridine under argon at 40°C for 8 hours. Yield: 128 mg (58.5% of theory). MS (DC1/NH3): 477 (M+H). HPLC (analytic): 92.8% RT: 5.13 min. column: Nucleosil C18 (125X4mm). mobile phase: 0.01m H?P04 / acetonitrile (gradient), flow rate:2 ml/min. 200-400 nm. Example 38 15 2-[2-Ethoxy-5-(4-ethylpiperazin-l -yl-sulfonylamino)phenyl]-7-(l -ethy 1 propyl)-5- methyl-3H-imidazo[5.]-fj[].2.4]-triazin-4-one O 10 The preparation was carried out analogously to the procedure of example 36 using 150mg (0.422 mmol) of the amino compound of example 48A and 421 mg (1.69 mmol) of 4-ethylpiperazinesulfonyl chloride hydrochloride in 6.81 ml of pyridine. The crude product is purified by chromatography on 100 ml of silica gel using ethyl acetate and acetone as mobile phase in a gradient system of from 9:1 to 1:1. Yield: 22.4 mg (10.0% of theory). MS (DCI/NH3): 532 (M+H): HPLC (analytic): 93.5% RT: 4.64 min. column: Nucleosil CI8 (125X4mm), mobile phase: 0.01m H3PO4 / acetonitriJe (gradient), flow rate:2 ml/min. 200-400 nm. 15 Example 39 2-t2-Ethoxy-5-(4-ethylpiperazin-l-yl-sulfonylamino)phenyl]-5-methyl-7-(2-ethyl-bepty])oH-imidazo[5.]-fJ[1.2.4]-triazin-4-one Q 20 The preparation is carried out analogously to the procedure of example 36 using 120mg (0.292 mmol) of the amino compound from example 50A and 581 mg (2.33 mmol) of 4-ethyl-piperazinesulfonyl chloride hydrochloride in 4.71 ml of pyridine at room lemperature. The crude product is purified by chromatography on 40 ml of silica gel using ethyl acetate and methanol as mobile phase. Yield: 63.6 mg (37.1% of theory). MS (ESI): 588 (M+H). TLC: Ri=0.57 (ethyl acetate:methanol = 8:2). 25 Example 40 2-[5-(4-Carboxybenzenesulfony]amino)-2-ethoxypheny]]-5-methyl-7-(2-ethy]hepty])-3H-imidazo[5J-fj[l,2.4]-triazin-4-one 0 Analogously to the procedure of example 36. 50 mg (0.12] mmol) of the amino compound from example 50A are reacted with 80.4 mg (0.364 mmol) of 4-chlorosulfonylbenzoic acid and 0.10 ml (1.22 mmol) of pyridine in 6 ml of letrahydrofuran overnight. The product is purified by chromatography on 40 ml of 10 silica gel using ethyl acetate and methanol as mobile phase in a gradient system of from 95:5 to 8:2. Yield: 65.4 mg (90.4% of theory). MS (DCI/NH3): 596 (M+H). HPLC (analytic): 90.4% RT: 7.08 min. column: Nucleosil CI8 (125X4mm), mobile 15 phase: 0.01 m H3PO4 / acetonitrile (gradient), flow rate:2 ml/min. 200-400 ran. 20 Example 41 2-[2-Ethoxy-5-(y-Morpholinopropanesulfony]amino)phenyl]-5-methyl-7-(2-ethyl-heptyl)-3H-imidazo[5.1 -f][l .2.4]-triazin-4-one Analogously to the procedure of example 36, 50 mg (0.121 mmol) of the amino compound from example 50A. are reacted with 111 mg (0.486 mmol) of y-morpholinopropanesulfony] chloride and 0.10 ml (1.22 mmol) of pyridine in 6 ml 5 of tetrahydrofuran overnight. Purification of the product on silica gel using ethyl acetate and methanol as mobile phase gives 66.3 mg (90.5% of theory). MS (ESI): 603 (M+H). HPLC (analytic): 95.9% RT: 7.05 min. column: Gromsil ODSB (125X4mm)r mobile phase: 0.01m H?P04 / acetonitrile (gradient), flow rate:2 ml/min. 200-400 nm. 0 Example 42 2-[2-Ethoxy-5-(l-methylimidazole-4-sulfonylamino)phenyl]-5-methyl-7-(2- ethylheptyl)-3H-imidazo[5.1-f|[].2.4]-triazin-4-one 15 Analogously to the procedure of example 36. 50 mg (0.121 mmol) of the amino compound from example 50A are reacted with 87.8 mg (0.486 mmol) of l-methylimidazole-4-sulfony] chloride and 0.10 ml (1.22 mmol) of pyridine in 6 mJ of tetrahydrofuran overnight. Purification of the product over silica gel using ethyl acetate and methanol as mobile phase gives 65.2 mg (96.6% of theory). MS (ESI): 556 (M+H)r HPLC (analytic): 92.9% RT: 6.74 minr column: Nucleosil CI 8 (125X4mm), mobile phase: 0.01m H3PO4/ acetonitrile (gradient), flow rate;2 ml/min. 200-400 nm. Example 43 2-[2-Ethoxy-5-methylsulfonylaminophenyl]-5"methyl-7-(2-ethylheptyl)-3H-imidazo-[5J-f][L2:4]-triazin-4-one O 15 Analogously to the procedure of example 36. 50 mg (0.121 mmol) of the amino compound from example 50A are reacted with 55.7 mg (0.486 mmol) of methanesulfony] chloride and 0.10 ml (1.22 mmol) of pyridine in 6 ml of tetrahydrofuran overnight. Purification of the product on silica gel using toluene and ethyl acetate from 8:2 to 5:5 gives 23.4 mg (39.3% of theory)- MS (ESI): 490 (M+H)r TLC: Rr=0.47 (toluene : ethyl acetate = 2:8). Example 44 2-[2-Ethoxy-5-isopropylsulfonylaminophenyl]-5-methyl-7-(2-ethylheptyl)-3H-irnidazo[5.1-f][1.2.4]-triazin-4-one O Analogously to the procedure of example 36. 50 mg (0.121 mmol) of the amino compound from example 50A are reacted with 333 mg (2.34 mmol) of isopropylsulfonyl chloride and 0.12 ml (1.46 mmol) of pyridine in 6 ml letrahydrofuran overnight. Purification of the product on 40 ml of silica gel using ethyl acetate and methanol as mobile phase gives 37.0 mg (49.0% of theory). MS(DC1/NH3):518(M+H)r TLC: R,=0.65 (toluene:ethyl acetate = 2:8). Example 45 15 2-[2-Ethoxy-5-(4-morpholinylsulfonamido)pheny]]-5'methyl-7-(2-ethylheptyl)-3H- imidazo[5.1-f][l,2.4]-triazin-4-one O Analogously to the procedure of example 36. 50 mg (0.121 mmol) of the amino compound from example 50A are reacted with 360 mg (1.94 mmol) of morpholine N-sulfonyl chloride and 0.10 ml (1.22 mmol) of pyridine in tetrahydrofuran overnight. Purification of the crude product on 40 ml of silica gel using toluene and ethyl acetate, 6:4 to 5:5. as mobile phase gives 9.3 mg (13.7% of theory). MS (ESI): 561 (M+H), HPLC (analytic): 94.8% RT: 7.74 min. column: Nucleosil CI8 (125X4mm), mobile phase: 0.01m H3PO4/ acetonitrile (gradient), flow rate:2 ml/min, 200-400 ran. 10 Example 46 2-[2-Ethoxy-5-(4-morpholinocarbony]amino)pheny]]-5-methy]-7-cyc]openTy]-3H-imidazo[5J-fj[1.2,4]-triazin-4-one 15 20 213 mg (0.601 mmol) of the amino compound from example 42A and 0.2 ml (1.43 mmol) of triethylamine are dissolved in 6 ml of tetrahydrofuran; the solution is cooled to 5°C, and 0.489 ml (4.22 mmol) of 4-morpholinocarbonyl chloride, dissolved in 4 ml of tetrahydrofuran. is injected. The reaction solution is stirred at room temperature overnight, ethyl acetate. NH4G solution and NaHCOs solution are added, the organic phase is separated off. the aqueous phase is re-extracted 3 times with ethyl acetate and the organic phases are combined, dried and concentrated. The product is chromatographed on 60 ml of silica gel using ethyl acetate/methanol as mobile phase. Yield: 275 mg (98% of theory). Yield 460 mg (9.3% of theory) MS (DC1, NH3): m/z (%) = 411 (M+H) (100) 'H-NMR (200 MHz; CDC13): S - 1.55 (t, 3 H); 1.68-2.21 (m, 8 H); 2.67 (s, 3 H): 2.80 (dd, 1 H); 2.95 (t, 1 H); 3.38-3.41 (m, 1 H); 3.67 (qui, 1 H); 3.98 (dd, 1 H); 4.12-4.32 (m, 3 H); 6.92-7.13 (m, 2 H); 7.78 (d, 1 H). Example 41A 2-(2-Ethoxy-5-nitrophenyl)-5-methyl-7-cyclopentyloH-imidazo[5J-fJ[1.2,4]-triazin-4-one O Using an ice-acetone bath. 48.6 ml of trifluoroacetic acid (TFA) and 12.1 ml of 70% strength nitric acid are cooled to -10°C. 3.0 g (8.86 mmol) of the compound from example 25A. dissolved in 7 ml of TFA are added dropwise, and the mixture is stirred at 0°C for 20 hours. The reaction solution is stirred into 400 ml of ice-water and 200 ml of dichloromethane and neutralized using about 200 ml of saturated sodium bicarbonate solution. The aqueous phase is separated off and extracted 3 times with dichloromethane, and the combined organic phases are dried and concentrated. The residue is chromatographed on silica gel using toluene with added ethyl acetate in a gradient from 1 ] to 60%. Yield: 2.56 g (75.5% of theory) 'H-NMR (200 MHz. DMSO): 1.37 (t. 3H), 1.58-2.00 (m. 8H). 2.49 (s. 3H), 3.50 (quin.. 1H). 4.26 iquar. 2H). 7.39 (d. 1H). 8.39-8.47 (m. 2H), 11.77 (s. 1H). Example 42A 2-(5-Amino-2-ethoxyphenyl)-5-methy]-7-cyclopentyl-3H-imidazo[5.1-f][ 1,2,4]-triazin-4-one O In 86 ml of ethanol and 86 ml of tetrahydrofuran 2.56 g (6.68 mmol) of the compound from example 41A are stirred in the presence of 288 mg of Pd/C (10%) under an H2 atmosphere for 20 hours. The reaction solution is filtered with suction through 30 ml of silica gel, the filter cake is washed with ethanol/tetrahydrofuran and ] 0 the filtrate is concentrated and dried under high vacuum overnight. The crude product is chromatographed on 500 ml of silica gel using toluene and ethyl acetate in a gradient system. Yield: 2.1 g (92.8% of theory) 'H-NMR (200 MHz. DMSO): 1.25 (t. 3H). 1.58-2.0 (m. 8H). 2.48 (s. 3H). 3.41-3.58 15 (quin., 1H). 3.97 (quar, 2H). 4.92 (s. 2H). 6.69-6.90 (dd and d, 3H), 11.34 (s. 1H). 20 Example 43A 2-(5-Nitro-2-propoxypheny])-5-methyl-7-cyclopentyl-3H-imidazo[5,l -f][ 1,2,4]-triazin-4-one Analogously to the procedure of example 41 A, 10.0 g (28.4 mmol) of the compound from example 26A are nitrated in 160 ml of trifluoroacetic acid and 40 ml of 70% strength nitric acid. The product is purified by silica gel chromatography using toluene and ethyl acetate in a gradient system. Yield: 5.15 g (45.7% of theory). 'H-NMR (200MHZ, DMSO): 0.95 (t, 3H). 1.60-1.93 (m. 8H). 1.93-2.10 (m, 2H), 2.50 (s, 3H). 3.50 (quin.. 1H). 4.17 (t. 2H). 7.40 (dd. ]H)r 8.38-8.46 (m. 2H), 11.62 (s. M). Example 44A 2-(5-Amino-2-propoxyphenyl)-5-methy]-7-cyclopentyl-3H-imidazo[5.] -f][ 1.2.4]-triazin-4-one O Analogously to the procedure of example 42AT 5.13 g (12.96 mmol) of the compound from example 43A are hydrogenated in tetrahydrofuran/ethanol (1:1) using 1.11 g of 10% Pd/C. The product is purified by silica gel chromatography using toluene and ethyl acetate as solvent gradient. Yield: 4.39 g (92.1% of theory). ]H-NMR (200MHz, DMSO): 0.91 (t, 3H)f 1.57-2.00 (mm, 10H), 2.45 (s, 3H), 3.41-3.58 (quin, 1H), 3.88 (L 2H), 4.93 (s. 2H)r 6.72 (dd, lH)r 6.80 (d, 1H), 6.90 (d, 1H). ] 1.30 (s, 1H). Example 45A 2-(2-Ethoxy-3-nitrophenyl)-5-methy]-7-propy]-3H-imidazo[5,l-f][L2,4]-triazin-4-one O 10 Analogously to the procedure of example 41 A. 1.5 g (4.80 mmol) of the compound from example 16A are nitrated in 27 ml of trifluoroacetic acid and 6.6 ml of 70% strength nitric acid. Yield: 1.73 g (83.7% of theory). MS (ESI): 358 (M+H). 15 HPLC (analytic): 83.0% RT: 5.86 min. column: Nucleosil CI 8 (125X4mm)f solvent: 0.01m H3PO4/ acetonitrile (gradient), flow rate: 2 ml/min: 200-400nm. TLC: Rr0.43 (toluene:ethyl acetate = 2:8). 20 Example 46A 2-(5-Amino-2-ethoxyphenyl)-5-methy]-7-propyl-3H-imidazo[5.]-fJ[1.2.4]-triazin-4- one Analogously to the procedure of example 42A, 1.72 g (4.63 mmol) of the compound from example 45A are hydrogenated in 150 ml of ethanol using 200 mg of 10% Pd/C. Yield: 862 mg (56.9% of theory). !H-NMR (200MHzr DMSO): 0.92 (t, 3H), 1.25 (t, 3H): 1.64-1.82 (hex, 2H), 2.50 (s. 3H), 2.82 (t, 2H), 3.90-4.01 (quar: 2H)r 4.93 (s. 2H).6.72 (dd, IH), 6.80 (d, IH). 6.90 (d, IH), 11.35 (s, IH): MS (DCI): 354 (M+H). TLC: Rf=0.33 (toluene:ethyl acetate = 1:9). E\ample 47A 2-(2-Ethoxy-5-nJtrophenyl)-5-methyl-7-(]-ethylpropy])-3H-imidazo[5.1-fj[ 1.2.4]-triazin-4-one O Analogously to the procedure of example 41 A. 2.0 g (5.88 mmol) of the compound from example 18A are nitraied in 33 ml of trifluoroacetic acid and 8.3 ml of 70% strength nitric acid. The product is purified by chromatography on 1000 ml of silica gel using toluene and ethyl acetate in a gradient system. Yield: 1.84 g (81.3% of theory). 'H-NMR (200MHz, DMSO): 0.73 (t, 6H), 1.16 (t: 3H), 1.61-1.82 (m, 4H), 2.50 (s. 3H), 3.01-3.18 (m, 1H): 4.00 (quar, 2H), 7.49 (t, IH), 7.91 (dd, IH), 8.12 (dd, 1H); 12.92 (s, IH). Example 48A 2-(5-Amino-2-ethoxypheny]>5-methyl-7-(]-ethylpropyl)-3H-imidazo[5,l-f][l,2,4]-triazin-4-one 0 15 Analogously to the procedure of example 42A. 1.84 g (4.77 mmol) of the compound from example 47A are hydrogenated in 150 g of ethanol using 200 mg of 10% Pd/C. Yield: 1.57 g (92.4% of theory). 'H-NMR (200MHz. DMSO): 0.75 (t, 6H), 1.24 (t, 3H). 1.66-1.84 (m, 4H), 2.50 (s. 3H). 3.11 (quin.. IH). 3.98 (quar. 2H). 4.93 (s. 2H). 6.71 (dd, IH). 6.78 (d, IH). 6.90 (d. IH), 11.33 (s, IH). 20 Example 49A 2-(2-Ethoxy-5-nitrophenyl)-5-methy]-7-(2-ethylheptyl)-3H-imidazo[5.1-f][1.2,4]-triazin-4-one Analogously to the procedure of example 41 A. 3.0 g (7.57 mmol) of the compound from example 23A are nitrated in 42.5 ml of trifluoroacetic acid and 10.7 ml of 70% strength nitric acid. The product is purified by chromatography on 500 ml of silica gel using cyclohexane and ethyl acetate in a gradient system of from 95:5 to 40:60. Yield: 1.95 g (58.4% of theory). TLC: Rj=0.65 (cyclohexane:ethyl acetate = 2:8). 10 Example 50A 2-(5-Amino-2-eThoxypheny])-5-methy]-7-(2-ethylhepH>3H-imidazof5.]-f|[L254]-triazin-4-one O 15 20 Analogously to the procedure of example 42A. 1.95 g (4.42 mmol) of the compound from example 49A are hydrogenated in 120 g of ethanol using 200 mg of 10% Pd/C. Chromatography on 400 ml of silica gel using cyclohexane and ethyl acetate in a gradient system from 90:10 to 40:60 gives 1.26 g (69.4% of theory). 'H-NMR (200MHz. DMSO): 0.70-0.83 (m. 6H). 1.11-1.80 (m. 12H). 1.62-1.81 (m. 3H). 2.50 (s. 3H). 3.11-3.25 (quin.. 1H). 3.97 (quar. 2H). 4.95 (s. 2H). 6.70-6.80 (m. 2H). 6.90 (d. 1H). 11.35 (s.lH). Example 51A 2-(2-Ethoxy-5-ch]oromethylpheny])-5-methyl-7-n-propyl-3H-imidazo[5.1-f][]52,4]-triazin-4-one A suspension of 1,50 g (4,8 mmol) of the compound from example 16A and 0.43 g (4.8 mmol) of paraformaldehyde in 25 ml of cone. HC1 was heated at 120°C for 2 h. The reaction mixture was poured into ice-water and extracted twice with ethyl acetate and then twice with CH^C^. The CH2C]2 phase was dried over MgS04 and concentrated under reduced pressure. This gave 1.22 g (70.4%) of the desired product. MS (DC1. NH3): m/z (%) = 361 [M+H] (100) 'H-NMR (200 MHz. D6-DMSO): 5 = 0.94 (tr 3H. CH3); 1.32 (L 3H. CH3); 1.82 (g. 2H. CH2); 2.61 (s, 3H. CH3); 3.02 (t. 2H? CH2); 4.12 (gf 2H. CH2); 4.81 (s; 2R CH2): 7.21 (d; 1H): 7.57 - 7.65 (m, 2H): 12.22 (bs, ]R NH). Example 52A 2-(2-Ethoxy-5-chloromethy]phenyl)-5-ethyl-7-n-propyl-3H-imidazo[5?l-fJ[K2,4]-triazin-4-one The preparation is carried out analogously to the procedure of example 51A using 1 g (3.06 mmol) of the compound from example 17A and 276 mg (3.06 mmol) of paraformaldehyde. Yield: 732 mg (59.6%) 10 Example 53A 2-(2-Ethoxy-5-chloromethylphenyl)-5-methyl-7-(Ll -dimethylbuty])-3H-irnidazo[5.1 -f] [ L2,4]-triazin-4-one H,C O HN 15 The preparation is carried out analogously to the procedure of example 51A using 1.5 g (4.2 mmol) of the compound from example 19A and 380 mg (4.2 mmol) of paraformaldehyde. Yield: 850 mg (49.8%) 'H-NMR (200 MHz. CDC13): 0.83 (tT 3H)r 1.05 - 1.2 (m. 2H); 1.55 (sr 6H); 1.6 (t. 3H); 1.95 - 2.1 (m. 2H): 2.65 (s. 3H): 4.3 (quar.. 2H): 4.62 (s. 2H); 7.05 (d. 1H): 7.53 (dd, 1H); 8.12 (d.lH); 9.9 (sr 1H). 20 Example 54A 2-(2-Ethoxy-5-ch]oromethy]pheny])-5-ethy]-7-cyc]opentyl-3H-imidazo[5J-f][L2!4]-triazin-4-one 5 A suspension of 1.0 g (2.8 mmol) of the compound from example 27A and 256 mg (2.8 mmol) of paraformaldehyde in 20 ml of cone. HC1 was heated at 120°C for 2 hT giving a homogeneous solution. This solution was poured into ice-water and extracted twice with CH2G2. and the organic phase was dried over MgS04 and concentrated under reduced pressure. Recrystallization from CH2CI2 / ether gave 10 314 mg (27.6 %) of the desired product. Concentration of the mother liquor gave a further 806 mg (70.9%) of product. MS (EI): m/z (%) = 400 [ VT ] (28) 'H-NMR (200 MHz. CDC13): 6-1.50 (L 3H. CH3). 1.61 (t. 3H; CH3), 1-62 - 2.45 (m. 8H; 4 x CH2), 3.33 (u 2Hr CH2)T 3.91 (m. IH. CH). 4.28 (g. 2H: CH20); 4.61 (s. 15 2R CH2), 7.10 (d,lH); 7.63 (ddT 1H)7 8.15 (d, 1H): 10.51 (bs. 1RNH). Example 55A 2-(2-Ethoxy-5-chloromethylpheny])-5-methyl-7-cycloheptyl-3H-imidazo[5J- 20 f][L2;4]-triazin-4-one 10 A suspension of 600 mg (1.6 mmol) of the compound from example 28A and 147 mg (1.6 mmol) of paraformaldehyde in 10 ml of cone. HC1 was heated at 120°C for a total of 4 h, with foaming reaction product being rinsed from the condenser. The mixture was poured into ice-water, the aqueous phase was extracted twice with ethyl acetate and the organic phase was dried over MgS04. The organic phase was concentrated and the residue was then triturated with ether, and precipitated product was filtered off. This gave 558 mg of a 9:1 - mixture of product and starting material and another 189 mg (26.5%) of product by concentration of the mother liquor. MS (DCIr NH3): m/z (%) = 415 [ M + H ] (100) 'H-NMR (200 MHz. Dfi-DMSO): 8 = 1.30 (L 3H. CH3). 1.45 - 2.15 (m: 12H. 6 x CH2). 2.60 (s. 3H, CH3). 3.45 (m. 1H. CH): 4.13 (g. 2H: CH2). 4.82 (s. 2R CH2). 7.19 (ddT lH)r 7.62 (m. 2H), 12.18 (bs. 1H.NH). 15 Example 56A 2-(2-Ethoxy-5-ch]oromethy]pheny])-5-ethy]-7-cyc]ohepty]-3H-imidazo[5,]-f] [1,2,4]-triazin-4-one Q ^ CH, 20 Analogously to example 51 A. 100 mg (0.26 mmol) of the compound from Example 29A in 2 ml of cone. HC1 were heated with 23.7 mg (0.26 mmol) of paraformaldehyde at 120°C for 2 h. Chromatographic purification (gradient: CH2CI2 : MeOH = 1 —-> 50 : 1) gave 60.8 mg (53.9%) of the desired product. MS (DCI, NH3): m/z (%) - 429 [ M + H ] (100) 5 'H-NMR (200 MHz, CDC13): 5 = 1.32 (t, 3H; CH3); 1.58 (t, 3H, CH3), 1.60 - 2.08 (m, 12H, 6 x CH2), 3.02 (g, 2R CH2), 3.44 (m; 1H, CH), 4.26 (g, 2H5 CH20), 4.63 (s, 2H. CH2), 7.06 (d, 1H), 7.54 (dds 1H), 8.16 (d, 1H), 9.84 (bs, 1H, NH). 10 Example 57A 2-[5-(2-Bromoacetyl)-2-ethoxypheny]]-5-methyl-7-propy]-3H-imidazo[5,]-f][ 1,2,4]-triazin-4-o Br A solution, cooled to 0°C. of 4g (12.8 mmol) of the compound from example 16A in 15 80 ml of CH2CI2 was initially admixed dropwise with 5.17g (25.6 mmol) of bromoacety] bromide and then, a little at a time, with 5.12g (38.4 mmol) of AICI3. The mixture was warmed to room temperature and then stirred for 30 min. and heated at reflux for 2 h. The reaction mixture was poured into ice-water and extracted once with CH2G2. and the organic phase was washed with sat. NaCl solution and 20 dried over MgSO^. The residue obtained after concentration under reduced pressure was triturated with ether, and the product was filtered off with suction. This gave 6.2g (> 95%) of the desired product as a mixture of phenacyl bromide and phenacyl chloride. MS (ESI): m/z = 435 [M (Br) + H ] (100). 389 f M (CIJ + H ] (85) 25 'H-NMR (200 MHz. D6-DMSO) : 6 = 0.94 (t. 3H. CH3). 1.32 (t. 3R CH3). 1.78 (m, 2H. CH2), 2.61 (s, 3FL CH3); 3.03 (t, 2H; CH2), 4.25 (g. 2H, CH2)r 4.89 (s, 2H, CH2 Br); 5.18 (s; 2H, CH2-C1), 7.34 (d. 1H)? 8.07 - 8.25 (m, 2H), 12.40 (bs, 1H, NH) Example 58A 2-[5-(2-BromoaceTyl)-2-ethoxyphenyl]-5-ethy]-7-propy]-3H-imidazo[5,l-f][l,2,4]triazin-4-one A solution, cooled to 0°C, of 1 g (3.1 mmol) of the compound from example 17A in 10 80 ml of CH2C12 was admixed dropwise with 1.2 g (6.1 mmol) of bromoacetyl bromide and a little at a time with 1.2 g (9.1 mmol) of AlCh. The reaction mixture was wanned to room temperature (30 min.) and then heated at reflux for 2 h and carefully poured into ice-water. Following extraction with CH2C12. dn'ing over MgS04 and concentration under reduced pressure, the residue was triturated with 15 ether. This gave 1.33 g (33% pure according to LC-MS) of the desired product which was reacted further without further purification. MS (ESI): m/z (%) - 447 [ M + H ] (100) 20 Example 59A 2-[5-(2-Bromoacetyl)-2-ethoxyphenyl]-5-methyl-7-cyc]opentyl-3H-imidazo[5.1' fj[L2.4]triazin-4-one The compound was obtained analogously to the compound from example 57A from 1 g (2.95 mmol) of the compound from example 25A and 1.19 g (5.9 mmol) of bromoacety] bromide in the presence of 1.18 g (8.86 mmol) of aluminum trichloride. M.p.: 186°C (ethyl acetate/ether) Yield: 770 mg (57%) Example 60A 2-[5-(2-Bromoacety])-2-ethoxypheny]]-5-methyK7-cyclohepty]oH-imidazo[5,l-f][1.2.4]triazin-4-one Analogously to example 57A. 1.36g (3.7 mmol) of the compound from example 28A were reacied with 1.5g (7.4 mmo]) of bromoacety] bromide and 1.48 g (1.1 mmol) of aluminum trichloride. Trituration with ether gave 1.2 g (66.3%) of the desired product. MS (DC! / NH3): m/z (%) = 487 f M + H ] (27 %) 'H-NMR (200 MHz. CDC13): o = 1.63 (t. 3H. CH3). 1.75 (bs. 6R). 1.89 - 2.42 (m. 6H). 2.94 (s. 3H. CH3). 3.75 (m. 1H. CH). 4.37 (s. 2H. CH2-Br). 4.43 (g. 2H. CH2). Preparation of the active compounds 10 15 20 -K Example 1 2-[2-Ethoxy-5-(4-morpho]iny]-sulfonamido)phenyl]-5-methyl-7-cyclopentyl-3H-imidazo-[5,l-f][l,254]-triazin-4-one O °u 250 mg (0.71 mmol) of the amino compound from example 42A are dissolved in 10 g of dichloromethane and cooled to 0°C. and 525 mg (2.83 mmol) of morpholine N-sulfony] chloride, dissolved in 5 g of dichloromethane. are added under argon. The mixture is stirred without cooling for 30 minutes, and 336 mg (4.24 mmol) of pyridine p.a. are then added dropwise. After a further 30 minutes, another 3.4 ml of pyridine are added dropwise. and the mixture is stirred at room temperature overnight. The reaction solution is concentrated under reduced pressure at 40°C. whereupon the color of the solution changes to an intensive red. The mixture is stirred with 20 ml of ammonium chloride solution, with addition of a little sodium bicarbonate solution, for about 10 minutes and then extracted 4 times with ethyl acetate, and the extracts are dried and concentrated. The red oil is dissolved in 10 ml of toluene, applied to 100 ml of silica gel and chromatographed using toluene/ethyl acetate in a gradient system of from 80:20 to 20:80. The desired fractions are combined, concentrated and dried under reduced pressure. Yield: 211 mg (59.0% of theory). 'H-NMR (200 MHz. DMSO): 1.31 (t. 3H). 1.55-2.10 (m. 8H). 2.48 (s, 3H), 3.10 (m. 4H). 3.41-3.51 (quin.. 1H). 3.55 |m. 4H). 4.09 (quarr 2H)r 7.10-7.26 (m. 2U% 7.38 (dd. 1H). 9.90 is. 1H). 11.51 (s. IHj. HPLC (analytic): 99.9% RT: 3.62 min. column: Nucleosil C18 (125X4mm)T mobile phase; 0.01 M H3PO4/ acetonirile (gradient), flow rate: 2ml/min. 200-400 ran. The following compounds are prepared analogously to the procedure of example 1 (example 2 to example 12): 10 Example 2 2-[2-Ethoxy-5-(4-methanesulfonylamino)phenyl]-5-methyl-7-cyclopentyl-3H-imidazo-[5,l-f][1.2.4]-triazin-4-one O 150 mg (0.42 mmol) of the compound from example 42A are reacted with 72.9 mg (0.64 mmol) of methanesulfonyl chloride. Yield: 172 mg (93.9% of theory). 'H-NMR (200 MHz. DMSO): 1.30 (t: 3H). 1.59-2.03 (m; 8H). 2.47 (s, 3H), 2.97 (s. 3H)r 3.47 (quin.. 1H). 3.99-4.14 (m. 2H). 7.17 (d. 1H), 7.33-7.40 (dd, 2H). 20 Example 3 2-[2-Ethoxy-5-(4-isopropylsulfonylamino)pheny]]-5-methy]-7-cyclopenty]-3H-imidazo-[5.]-f][1.2,4]-triazin-4-one 100 mg (0.28 mmol) of the compound from example 42A are reacted with 60.5 mg (0.42 mmol) of isopropylsulfonyl chloride. Yield: 112 mg (86.1% of theory). MS (DCI): 460 (M+H). HPLC (analytic): 81.6% RT: 5.85 min. column: Nucleosil CI 8 (125X4mm), mobile phase: 0.01M H?P04/ acetonirile (gradient), flow rate: 2 ml/min. 200-400 nmr TLC: Rf=0.55 (cyclohexane:ethyl acetate - 2:8). 10 Example 4 2-[5-(4-N.N-Dimethylsu]famoylamino)-2-ethoxypheny]]-5-methy]-7-cyclopenty]-3H-imidazo-[5.1-f][1.2.4]-triazin-4-one O 15 100 mg (0.28 mmol) of the compound from example 42A are stirred with 183mg (1.27 mmol) of N.N-dimethylsulfamoy) chloride and 0.30 ml (3.71 mmol) of pyridine for 2 days. Yield: 90.8 mg (69.7% of theory). 'H-NMR (300 MHz. DMSO): 1.30 (t. 3H). 1.59-2.07 (m. 8H). 2.47 (s. 3H). 2.70 (s, 6H), 3.45 (quin., 1H), 4.07 (quar, 2H); 7.10 (d, 1H), 7.32 (dd, 1H), 7.39 (d, 1H); MS (DCI): 461 (M+H). Example 5 2-[2-Ethoxy-5-(benzofurazane-4-sulfonylamino)phenyl]-5-methyl-7-cyclopentyl-3H-imidazo-[5.1-f][L2,4]-triazin-4-one O 120 mg (0.34 mmol) of the compound from example 42A are reacted with 111 mg 10 (0.509 mmol) of benzofurazane-4-sulfony] chloride and 0.17 ml (2.10 mmol) of pyridine. Yield: 109 mg (60.1% of theory). 'H-NMR (200 MHzr DMSO): 1.10 (t. 3H). 1.63-2.05 (m: 8H), 2.45 (sr 3H)T 3.39 (quin.. ]H)r 4.00 (quar. 2H). 7.04 (dr lH)r 7.12-7.28 (m, 2H)r 7.70 (dd. lH)r 8.09 (dr 1H). 8.38 (dr 1H). 10.84 (s.lH), 11.39 (s, 1H): 15 MS (DCI): 536 (M+H). 20 Example 6 2-[5-(4-n-Butoxybenzenesulfonylamino)-2-ethoxyphenyl]-5-methyl-7-cyclopentyl-3H-imidazo-[5.1-f][1.2,4]-triazin-4-one o o 150 mg (0.424 mmol) of the compound from example 42A are reacted with 186 mg (0.747 mmol) of 4-(n-butoxy)-benzenesulfonyl chloride and 0.34 g (4.30 mmol) of pyridine in 6 ml of tetrahydrofuran. Yield: 99.5 mg (41.4 % of theory). !H-NMR (300 MHz. DMSO): 0.92 (t. 3H). 1.25 (t, 3H), 1.40 (hex., 2H); 1.60-2.05 (m. 10H), 2.45 (s. 3H). 3.43 (quin.. IH). 4.00 (m. 4H); 7.03 (dd, 3H); 7.15-7.28 (m: 2H). 7.67 (d, 2H). 10.03 (s. IH), 11.43 (s. IH): MS (ESI): 566 (M+H). 10 15 Example 7 2-f5-Bis(N.K1-4-Butoxybenzenesulfonyl)amino-2-ethoxy-pheny]]-5-methy]-7-cyclo-pentyl-3H-imidazo[5.1-f)[1.2.4]-triazin-4-one O In example 6, 63.3 mg (19.2% of theory) of the bis derivative are isolated as a by¬product. 'H-NMR (200 MHz, DMSO): 0.95 (t. 6H), 1.30-1.52 (m, 8H), 1.65-2.03 (m, 11H), 2.47 (s; 3H), 3.47 (quin., 1H); 4.04-4.21 (m, 6H)T 7.06-7.25 (ra, 7H), 7.72 (d, 4H), 11.54 (s,lH); MS (ESI): 778 (M+H). Example 8 2-[2-Ethoxy-5-(l-methy]imidazole-4-su]fonylamino)phenyl]-5-methy]-7-cyc]openty]-3H-imidazo-[5.1-f][1.2;4]-triazin-4-one O 150 mg (0.424 mmol) of the compound from example 42A are reacted with 307 mg (1.70 mmol) of l-methylimidazole-4-sulfonyl chloride and 0.34 ml (4.24 mmol) of pyridine in 5 ml of tetrahydrofuran. Yield: 155 mg (73.8% of theory). ]H NMR (200 MHz. DMSO): 1.27 (L 3H). 1.55-2.10 (rm 8H), 2.47 (s, 3H), 3.47 (quint.. lH)r 3.65 (s. 3H). 4.02 (quar. 2H). 7.05 (d. IH). 7.30 (dd. 2H), 7.75 (dd, 2H), 10.13 (s.lH)J 1.47 (s.lH): MS (ESI): 498 (M+H). Example 9 2-f2-Ethoxy-5-f4-methy]piperazin-]-y]-sulfonylamino)pheny]]-5-methy]-" cyclopentyl-3H-imidazo-[5.1-f)[1.2.4]-triazin-4-one 120 mg (0.34 mmol) of the compound from example 42A are reacted with 319 mg (1.36 mmol) of 4-methyl-l-piperazinesulfonyl chloride in 8 ml (98.9 mmol) of pyridine overnight. Yield: 25.8 mg (14.7% of theory). 'H NMR (200 MHz.. CDCL3): 1.56 (t. 3H), 1.65-2.20 (m, 9H), 2.27 (s, 3H), 2.42 (t. 4H). 2.62 (s, 3H). 3.30 (t. 4H). 3.62 (quin., 1H).4.22 (quar, 2H); 7.02 (d. IH), 7.40 (dd. lH),7.97(d. IH), 10.00 (s, IH); MS(ESI):516(M+H). 15 Example 10 2-[5-(6-Ch]oroimidazo(2.1-b)thiazole-5-su)fonylamino)-2-ethoxyphenyl]-5-methy]-7-cyclopentyl-3H-imidazo[5.1-f][L2.4]-triazin-4-one O 149 mg (0.42 mmol) of the compound from example 42A are reacted with 328 mo (1.28 mmol) of 6-chloroimidazo(2.1-b)thiazole-5-sulfony] chloride and 0.68 ml (8.41 mmol) of pyridine in letrahydrofuran. initially ai room temperature and then ai Example 19 2-[5-(4-Methylpiperazin-]-y]-su]fony]amino)-2-propoxy-phenyl]-5-methy]-7-cyclo-pentyl-3H-imidazo[5,l-fJ[L2.4]-triazin-4-one O 10 150 mg (0.408 mmol) of the compound from example 44A are treated with 576 mg (2.45 mmol) of 4-methyl-l-piperazinesulfonyl chloride in 6.6 ml (81.6 mmol) of pyridine for 3.5 hours. Yield: 106 mg (48.8 % of theory). !H NMR (300 MHz; DMSO): 0.93 (t. 3H). ] .53-2.10 (m. 10H)r 2.17 (s; 3H). 2.27 (s. 4H): 2.47 (s. 3H); 3.08 (sr 4H)r 3.48 (quin.r IH). 3.97 (t. 2H): 7.13 (d. IH). 7.32 (dd. lH)r7.40(d. lH),9.87(s. 1H): 11.48 (s.lH); MS (ESI): 530 (M+H). 15 Example 20 2-[5-(4-Methylpiperazin-l-yl-sulfonylamino)-2-propoxyphenyl]-5-methyl-7-cyclo-pentyloH-imidazo [5.1-fj[L2.4]-triazin-4-one dihydrochloride O Analogously to the procedure of example 54. 230 mg (0.647 mmol) of the amino compound from example 48A are reacted with 284 mg (1.29 mmol) of 4-(trifluoromethylthio)pheny] isocyanate in 20 ml of tetrahydrofuran for 4 hours. The crude product is purified by silica gel chromatography using toluene and ethyl acetate as mobile phase. Yield: 138 mg (37.2% of theory). 'H-NMR (200 MHz. DMSO): 0.77 (t. 6H)r 1.30 (t. 3H). 1.63-1.81 (mr 4H). 2.50 (s. 3H). 3.1) (quin.. 1H). 4.09 (quar. 2H). 7.12 (d. lH)r 7.56 (d. 1H)? 7.62 (s: 4H); 7.68 (d. lH):8.34(s. 1H), 13.52 (s, 1H): MS (ESI): 575 (M+H). Example 56 l-{3-(7-(l-Ethy]propyl>5-methyl-4-oxo-3.4-dihydroimidazo[5;l-f)[L2:4]-triazin-2-yl)-4-ethoxy-phenyl}-3-(4-fluorophenylsulfonyl)-urea O 10 The preparation was carried out analogously to the procedure of example 54 using 230 mg (0.647 mmol) of the amino compound from example 48A and 260 mg (1.294 mmol) of 4-fluorobenzenesulfonyl isocyanate in 15 ml of tetrahydrofuran. The mixture is stirred at room temperature for 4 hours, and the crude product is then isolated on silica gel using toluene and ethyl acetate. Yield: 54.6 mg (15.2% of theory). MS (ESI): 557 (M+H), HPLC (analytic): 70.0% RT: 6.68 min, column: Nucleosil CI8 (125X4mm), mobile phase: 0.01m H3PO4/ acetonitrile (gradient), flow rate:2 ml/min, 200-400 nm. Example 57 l-{3-(7-Cyclopentyl-5-methyl-4-oxo-3,4-dihydroimidazo[5,l-f][l,2,4]-triazin-2-yl)-4-propoxyphenyl} -3-(4-fluorophenyIsulfonyl)-urea 15 20 -^N NH fiOi o 0 o The preparation is carried out analogously to the procedure of example 54 using 150 mg (0.408 mmol) of the amino compound from example 44A and 411 mg (2.04 mmol) of 4-fluorobenzenesulfonyl isocyanate in 12 ml of tetrahydrofuran, which are reacted overnight. Yield: 163 mg (70.1% of theory). 'H-NMR (400 MHz, DMSO): 0.90 (t, 3H), 1.54-2.08 (m, 10H), 2.45 (s, 3H), 3.45 (quin., 1H), 3.88 (t, 2H), 6.92 (d, 1H), 7.17 (t, 2H), 7.53 (d, 1H), 7.63 (s, 1H), 7.82 (m, 2H), 8.47 (s, 1H), 11.37 (s, 1H); MS (ESI): 569 (M+H). 10 Example 58 l-{3-[7-(2-EthylhepTyl)-5-methy]-4-oxo-3.4-dihydroimidazo[5J-f][h2!4]-triazin-2-y]]-4-ethoxyphenyl}-3-(4-fluorophenylsulfony])-urea O s; 0 w O Analogously to the procedure of example 54. 50 mg (0.121 mmol) of the amino compound from example 50A are reacted with 548 mg (2.72 mmol) of 4-fluorobenzenesulfonyl isocvanate in tetrahvdrofuran for 2 days. Purification of the crude product on silica gel using toluene and ethyl acetate. 4:6 to 3:7. as mobile phase, gives 36.2 mg (48.6% of theory). MS(ES1):613(M+H)r HPLC (analytic): 81.0% RT: 4.92 min. column: Nucleosil CI8 (125X4mm). mobile phase: 0.01m H?P04/ acetonitrile (gradient), flow rate:2ml/min. 200-400nm. 15 Example 59 10 15 12.4 ul (0.16 mmol) of chloroacetyl chloride were slowly added dropwise to a solution of 50 mg (0.14 mmc>l) of the amine example 42A in 1.2-dichloroethane and 21.6 ul (0.16mmol)ofEt3N. After 2 h. 1 ml of sat. NaHC03 solution was added and the mixture was filtered through lg of Extrelut (CH2CI2). The crude product was re-dissolved in 1.2-dichloroethane. 87.1 ul (0.34 mmol) of morpholine were added and the mixture was heated at 100°C for 10 h. The mixture was stirred at room temperature overnight. 0.5 ml of sat. NaHC03 solution was added and the mixture was filtered through 500 mg of Extrelut / 500 mg of Si02 (ethyl acetate). The concentrated crude product was purified by preparative thin-layer chromatography (CH2C12 : MeOH = 15:1). This gave 18.9 mg (34.5%) of the desired product (81% pure according to HPLC). MS (ESI): m/z (%) 481 [ M + H ] (100) 'H-NMR (200 MHz: D6-DMSO): 5 = 1.29 (t, 3H; CH3), 1.55 - 2.05 (m, 8H, CH2), 3.12 (s, 2H. CH2). 3.45 (m. 1H. CH). 3.63 (t. 4H. CH2), 4.07 (g, 2R CH2): 7.11 (d. 1H). 7.76 (m. 2H). 9.78 (bs. 1H; NH). 11.53 (bsT 1H. NH). Example 60 20 12.3 ul (0.014 mmol) of chlorosulfony] isocyanate were slowly added dropwise to a solution, cooled to 0°C, of 50 mg (0.014 mmol) of the amine example 42A in 10 1.2-dichloroetbane. The mixture was allowed to warm to room temperature and then stirred for another hour, and 12.3 mg (0.014 mmol) of morpholine and ] equivalent of morpholinomethyl-polystyrene (3.47 mmol/g) were added. The mixture was stirred overnight and then filtered through 1 g of silica gel (ethyl acetate), and the crude product was purified by preparative thin-layer chromatography (CH2CI2 : MeOH = 20:1). This gave 2.3 mg (3.0%) of the sulfonylurea derivative (91% pure according to HPLC) 'H-NMR (200 MHz, CDCI3): 8 = 1.55 (t: 3H. CH3). 1.64 - 2.15 (mr 8H). 2.63 (s, 3H. CH3); 3.51 (t. 4H. CH2). 3.64 (m. 1H). 3.78 (t. 4R CH2)r 4.23 (g, 2H. CH2): 6.38 (bsT 1H, NH), 7.02 (d. 1H), 7.73 (dd, 1H), 7.86 (dr 1H), 9.95 (bs, 1H, NH). Example 61 15 Initially. 7.4 ul (0.08 mmol) of chlorosulfonv] isocyanate were added dropwise to a solution, cooled to 0°C. of 30 mg (0.08 mmol) of the amine example 48A in 1.2-dichloroethane. The mixture was allowed to warm to room temperature and then stirred for another hour, and 7.3 mg (0.08 mmol) of morpholine and a suspension of 30 mg of morpholinomethyl-polystyrene (3.47 mmol/g) in 1.2-dichloroethane were 20 added. After 3 h. the reaction mixture was filtered and the crude product was purified chromatographically (gradient: CH2C12 + CH2C12 : MeOH = 100 + 40:1). This gave 4.8 mg (10.9%) of the sulfonylurea (91% pure according to HPLC). 'H-NMR (200 MHz, D6-DMSO): 5 = 0.75 (t 6R CH3), 1.29 (t, 3H, CH3); 1-72 (m: 4R CH2), 2.53 (s. CH3. shoulder o / D6-DMSO)? 3.12 (ms 1H, CH), 3.42 (bt, 4H. CH2), 3.59 (bt, 4H, CH2), 4.06 (g, 2H. CH2), 7.07 (d, 1H), 7.57 (m. 2H), 8.55 (bs.. 1H,NH), 11.45 (bs,lH,NH). 10 15 Example 62 Analogously to example 61, 30 mg (0.08 mmol) of the amine example 48A were converted into 9.5 mg (20.1%) of the sulfonylurea (86% pure according to HPLC). MS (ESI): m/z (%) = 561 [ M + H ] (30) 'H-NMR (300 MHz. D?COD): § = 0.80 (t. 6H. CH3). 1.42 (t, 3H. CH3), 1.83 (m, 4H. CH2. CH), 2.34 (s. 3H CH3), 2.52 (t. 4H. CH2). 2.54 (s. 3H. CH3), 3.57 (t. 4H. CH2). 4.17 (g. 2H. CH2), 7.09 (d. 1H), 7.49 (dd. 1H). 7.69 (d, 1H). Example 63 O^NH A second solution of 15 mg (0.04 mmol) of the amine example 50A in 1 ml of 5 dioxane was slowly added dropwise to a solution, cooled to -78°C. of 3.2 mg (0.02 mmol) of chlorosulfony] isocyanate in 1 ml of ether. A suspension was formed. which was briefly warmed to 0°C and then stirred at -78°C for 1 h. and 12.6 mg (0.14 mmol) of morpholine were then added at 0°C. After 2 h. 2 ml of 1 M H2S04 were added, and the mixture was filtered through 3 g of Extrelut (mobile phase: 10 CH2C12). The concentrated crude product was purified by preparative thin-layer chromatography (CH^Cb : MeOH = 20:1) giving 6.6 mg (30.2%) of the desired product. MS (ESI): m/z (%) = 603 [ M + H ] (100) 'H-NMR (300 MHz, D3COD): 6 = 0.86 (m. 6H. 2 x CH3), 1.24 (m, 8Hr 4 x CH2). 15 1.47 (L 3H, CH3)r 1.71 - 2.02 (m, 4H. 2 x CH2)r 2.63 (s, 3H. CH3), 3.63 - 3.85 (m. 7R 3 x CH2. CH). 4.23 (g. 2H. CH20). 7.18 (dr 1H). 7.76 (dd5 1H). 8.06 (d; 1H). Example 64 VNH 10 Analogously to example 63. 14.9 mg (0.04 mmol) of the amine example 50A were reacted with 3.2 mg (0.02 mmol) of chlorosulfony] isocyanate and 14.5 mg (0.14 mmol) of N-methylpiperazine. Preparative thin-layer chromatography gave 2.4 mg (10.8%) of the desired product. MS (ESI): m/z (%) = 616 [ M + H ] (100) 'H-NMR (200 MHz. CDC13): S = 0.83 (m. 6Hr 2 x CH3). 1.09 - 1.34 (m. 11H. 4 x CH2. CH3). 1.85 (m. 4H. 2 x CH2). 2.31 (sr 3H. CH3). 2.49 (btr 4R 2 x CH2). 2.65 (s. 3H. CH3)T 3.40 (bt 4H. 2 x CH2)r 4.01 (s, 2Hr CH2), 4.26 (g; 2H; CH2): 7.05 (d, 1H). 7.83 (ddr ]H)r 8.13 (d51H). 8.29 (bs5 1H). Example 65 I CH3 A solution of 50 mg (0.14 mmol) of the amine example 42A. 18.0 mg (0.17 mmol) of freshly distilled benzaldehyde and 23.5 mg (0.17 mmol) of diethyl phosphite was heated at 80°C for 20 h. The volatile components were removed under high vacuum and the residue was purified chromatographically (gradient: CH2CI2 + CH2G2 : MeOH = 10:1). The two product-containing fractions were combined and re-purified by preparative thin-layer chromatography (CH2Q2 : MeOH = 20:1). This gave 20.1 mg (24.5%) of the desired product. MS (ESI): m/z (%) = 580 [ M + H ] (100) 'H-NMR (200 MHz. D6-DMSO): 6 = 1.05 (t, 3H. CH3), 1.22 (m, 9H, 3 x CH2), 1.55 - 2.05 (m. 8H: 4 x CH2); 3.65 - 4.15 (m, 7H; 3 x CH2. CH), 5.02 (dd, 1H, CHN). 6.32 (ddr 1HT NH)r 6.90 (m, 2H). 7.05 (d; JH)r 7.29 (m, 3H), 7.52 (m, 2H)S 11.32 (bs, 1H;NH). 10 15 Example 66 19 uj (0.16 mmol) of diphosgene were added dropwise to a solution of 80 mg (0.23 mmol) of the amine example 48A in 1.4-dioxane. and the mixture was stirred for 20 h. Following concentration under reduced pressure, the residue was Twice taken up in benzene and re-concentrated. 30 mg (0.07 mmol) of the resulting carbamoyl chloride were, as a crude product, dissolved in 1 ml of 1,2-dichloroethane. 8.6 mg (0.09 mmol) of N-methylpiperazine were added and the mixture was stirred at room temperature for 20 h. Quenching with 0.5 ml of H2O and filtration through Extrelut / silica gel (CH2C12 : MeOH = 95:5) gave 30 mg (87%) of the urea derivative (90% pure according to HPLC). MS (DCI, NH3): m/z (%) 482 [ M + H ] (10) 'H-NMR (200 MHz, D6-DMSO): 0 - 0.75 (t, 6H. CH3), 1-28 (t, 3R CH3), 1.72 (m. 4R CH2), 2.22 (bt; 4R CH2): 3.12 (m, 1H; CH), 3.43 (bt 4R CH2), 3.91 (s, 3R CH3). 4.05 (g, 2R CH2)T 7.05 (d. 1H), 7.58 (m: 2H). 8.53 (bs, 1R NH), 11.48 (bsT 1RNH) Example 6? 10 Analogously to example 66, 30 mg (0.08 mmol) of the carbamoyl chloride were reacted with 7.51 (0.09 mmol) of morpholine. For work-up, 0.5 ml of 2 N HCl were added, and the mixture was filtered through 500 mg of Extrelut and 500 mg of Si02 (CH2C12). This gave 26.2 mg (77.9%) of the urea (95.2% pure according to HPLC). MS (DC1. NH3): m/z (%) 469 [ M + H ] (10 %); 382 [ M - 87 ] (100) 'H-NMR (200 MHz, D6-DMSO): 5 = 0.75 (t. 6H. CH3), 1.28 (t. 3H, CH3). 1.72 (m. 4H. CH2). 3.10 (m. 1H. CH). 3.42 (i. 4H. CH2). 3.59 (t. 4H. CH2), 4.06 (g. 2H, CH2). 7.05 (d. 1H) 7.58 (m. 2H). 8.57 (bs. 1H. NH), 1 ] .49 (bs. 1H. NH) Example 68 In a parallel synthesis analogously to example 78. the compounds of the table below were prepared from the chloromethyl compound example 53 A and the appropriate amine. ]f. after 24 h at RT. there was still starting material detectable in the TLC. 5 stirring was continued at 60°C for another 24 h. Example 95 Analogously to example 76. 50 mg (0.12 mmol) of the chloromethvl compound example 55A were reacied with 31.5 mg (0.36 mmol) of morpholine at 80°C for ]5h. Purification by thin-Jayer chromatography (CH2G2/MeOH = ]0:1) gave 25.5 mg (46%) of the desired product. MS (ESI): m/z (%) = 466 [M+H] (100) 'H-NMR (200 MHz. CDC13): 6 = 1.56 (L 3H. CH3): 1.57 - 2.12 (m, 12R 6 x CH2): 2.48 (bt 4H; 2 x CH2); 2.62 (s. 3H. CH3); 3.43 (m. JR CH): 3.52 (s; 2K CH2); 3.72 (bt. 4H, 2 x CH2): 4.25 (g. 2H. CH2): 7.01 (d. IH): 7.47 (dd: IH); 8.11 (d. IH); 9.89 (bsrlH,NH). E*ample 96 10 H3C Analogously to example 76, 50 mg (0.12 mmol) of the chloromethyl compound example 55A were reacted with 41.3 mg (0.36 mmol) of N-ethylpiperazine at 80°C for 15 h. Purification by thin-layer chromatography (CH2CI2 : MeOH = 5:1) gave 18.9 mg (32%) of the desired product (92% pure acording to HPLC). MS (ESI): m/z (%) = 493 [M+H] (56) 'H-NMR (200 MHzr CDC13): 8 = 1.09 (tr 3R CH3); 1.56 (t, 3H, CH3); 1.57 - 2.12 (m. 12H. 6 x CH2); 2.44 (g, 2H. CH2); 2.52 (bm. 8R 4 x CH2): 2.66 (s, 3Hr CH3); 3.42 (m. 1H: CH); 3.54 (s. 2H. CH2): 4.25 (g. 2H. CH2); 6.99 (df 1H); 7.43 (dd. 1H): 8.10 (d. lH);9.89(bs. 1H.NH). Example 97 HX. Analogously to example 76. 50 mg (0.12 mmol) of the chloromethyl compound 15 example 55A were reacted with 32 mg (0.36 mmol) of N-ethyl-2-aminoethanol at 80°C for 15h. Purification by preparative thin-layer chromatography (CH2C12 : MeOH = 20:1) gave 17.3 mg (31%) of the desired product (87% pure according to HPLC). MS (ESI): m/z (%) = 468 [M+H] (80) 'H-NMR (200 MHz, D6-DMSO): 6 = 0.99 (t 3R CH3); 1.28 (t, 3H; CH3); 1.42 -2.05 (m, 12H); 3.46 (g. 2R CH2); 3.55 (s. 2R CH2); 4.07 (g, 2H, CH2); 4.35 (m, 1R CH); 7.09 (d. IH); 7.43 (dd, IH); 7.49 (d. IH). Example 98 15 Analogously to example 76. 50 mg (0.12 mmol) of the chloromethyl compound example 55A were reacted with 61 mg (0.36 mmol) of 4-(l-dioxazinyl)piperidine. This gave 17 mg (26%) of the desired product. MS (ESI): m/z (%) - 549 [M+H] (50) 'H-NMR (200 MHz. CDC13): 6 - 1.5 - 2.1 (m. 25H): 2.63 (s. 3H. CH3): 2.93 (bd. IH): 3.45 (m. IH. CH); 3.52 (s. 2H. CH2); 4.02 (m. 2H. CH2); 4.2 - 4.4 (m. 4H, 2 x CH2): 6.95 (d? IH); 7.45 (ddr IH); 8.08 (dr IH); 9.85 (bs; 1H.NH). Example 99 10 Analogously to example 76. 60 mg (0.14 mmol) of the chloromethy] compound example 56A were heated with 36.6 mg (0.42 mmol) of morpholine at 80°C for 15 h. Preparative thin-layer chromatography (CH2C12 : MeOH = 10:1) gave 38.7 mg (57.7%) of the desired product. MS (ESI): mJz (%) = 480 [ M + H ] (100) 'H-NMR (200 MHz. CDC13): 6 = 1.33 (t. 3R CH3)- 1.58 (i. 3H. CH3)r 1.60 - 2.10 (m. 3 2H. 6 x CH2). 2.49 (m. 4H. 2 x CH2). 3.02 (g. 2H. CH2). 3.45 (m. 1H: CH). 3.54 (sr 2H. CH2). 3.73 (bt. 4H. 2 x CH2)T 4.25 (g. 2H. CH2). 7.02 (d. 1H). 7.46 (dd. 1H). 8.11 (d. ]H)r9.90(bs. 1H.NH). Example 100 20.8 ul (0.15 mmol) of EirN were added to a suspension of 50 mg (0.13 mmol) of the chloromethy] compound example 54A in 1 ml of triethyl phosphite, and the mixture 10 was initially heated at 100°C for 30 min and then stirred at room temperature for another 48 h. 0.5 ml of sat. NaHC03 solution was added, and the mixture was filtered through a two-phase cartridge (500 mg of Extrelut / 500 mg of S1O2, mobile phase: ethyl acetate). The mixture was concentrated under reduced pressure and purified by thin-layer chromatography (CH2CI2 : MeOH = 20:1). This gave 14.4 mg (23%) of the desired product. MS (ESI): m/z (%) = 503 [ M + H ] (100) 'H-NMR (200 MHz. CDC13): 5 = 1.30 (t. 6H, 2 x CH3), 1.58 (t, 3H; CH3), 1.61 - 2.17 (m: 8H. 4 x CH2). 3.02 (g. 2H. CH2): 3.19 (d. 2H. CH2P), 3.62 (m, 1H, CH). 4.07 (gs 4R 2 x CH2X 4.24 (g, 2R CH2); 7.02 (gr 1H), 7.45 (dt, 1H), 8.02 (t, 1H). 9.89 (bs, 1H.NH). Example 101 15 Analogously to example 100. 50 mg (0.14 mmol) of the chloromethyl compound example 51A were reacted with 1 ml of triethyl phosphite and 23.1 |il (0.17 mmol) of Et3N. Preparative thin-layer chromatography (CH2CI2 : MeOH = 20.1) gave 20 mg of the desired product, which was contaminated with the unsubstituted triazinone NUN 4792 (2:1 acccording to HPLC). 20 MS (ESI): m/z (%) = 463 [ M + H ] (100) 'H-NMR (200 MHz. CDCI3): 5-1.03 (t. 3H. CH3): 1.29 (t. 6H. 2 x CH2)t 1.58 (t. 3H. CHO. 1.89 im. 2H. CH2). 2.65 (s. 3H. CH.O. 3.02 (2. 2H. CH2\ 3.19 (d. 2H. CH2P)r 4.08 (mr 4H; 2 x CH2)r 4.25 (g. 2R CH2); 7.03 (d, 1H), 7.48 (dt, 1H), 8.05 (t. lH),9.95(bs, 1H,NH). Example 102 0.2 g (3.0 mmol) of NaN? was added to a suspension of 1 g (2.7 mmol) of the chloromethy! compound example 51A in 30 ml of DMF. and the mixture was stirred for 17 h. 1 M NaOH was added, and the mixture was extracted twice with ethyl acetate. The organic phase was dried over MgSC>4 and concentrated under high 10 vacuum (the sample was warmed only in a lukewarm water bath), giving 0.82 g (80.5%) of the desired product. MS (DC1. NH3): m/z (%) = 368 f M + H ] (100) 'H-NMR (200 MHz. D6-DMSO): 6 - 0.93 (t. 3H. CH3). 1.32 (t. 3H. CH3). 1.73 (m. 2H. CH2). 2.83 (L 2H. CH2). 4.12 (gT 2H. CH2). 4.45 (s, 2FL CH2)? 7.20 (ds 1H), 7.54 15 ■ (m. 1H); 11.57 (bs, 1H.NH). Example 103 CH, 20 48 mg (0.73 mmol) of NaN? were added to a suspension of 250 mg (0.66 mmol) of the chloromethy] compound example 52A in o ml of DMF. and the mixture was stirred at room temperature for 17 h. 1 N NaOH was added, and the mixture was then extracted twice with ethyl acetate and the extracts were concentrated under reduced pressure and purified chromatographically (gradient: cvclohexane : ethyl acetate = 5:1 + 1:2). This gave 68 mg (28%) of the azide (88% according to HPLC). MS (ESI): m/z (%) = 382 [M+H] (100) 'H-NMR (400 MHz, CDC13): 6 = 1.03 (ts 3R CH3); 1.33 (t, 3R CH3); 1.58 (t, 3R CH3); 1.89 (m. 2R CH2); 3.01 - 3.07 (m. 4R 2 x CH2); 4.26 (g, 2R CH2); 4.49 (sr 2R CH2): 7.07 (d: 1H); 7.46 (dd. 1H); 8.09 (d, 1H); 9.86 (bs. 1R NH). 10 Example 104 36 mg (0.55 mmol) of NaN3 were added to a suspension of 200 mg (0.5 mmol) of the chloromethyl compound example 54A in 6 ml of DMF. and after 17 h at room 15 temperature, 1 M NaOH was added. The aqueous phase was extracted twice with ethyl acetate and the organic phase was dried over MgS04 and concentrated under reduced pressure. Chromatographic purification (cvclohexane : ethyl acetate =1:1) gave 105 mg (52%) of the azide (75% according to HPLC). MS (ESI): m/z (%) = 408 [M+H] (100) 20 'H-NMR (200 MHz. CDC13): 8 = 1.32 (t. 3H. CH3): 1.57 (t. 3H. CH3); 1.68 - 2.25 (m. 8R CH2); 3.02 (g, 2H, CH2): 3.63 (m. 1H. CH); 4.27 (g. 2H. CH2); 4.39 (s, 2H. CH2):7.06(d, 1H); 7.45 (dd, 1H): 8.11 (d. 1H); 9.84 (bs. 1RNH). Example 105 Analogously to example 102. 150 mg of the chloromethyl compound example 55a were reacted. Chromatographic purification (gradient: CH2CI2 + CH2CI2 : MeOH = 1 + 10:1) gave 35.4 mg (23%) of the azide (67% pure according to HPLC). MS (ESI): m/z (%) - 422 [M+H] (100) 'H-NMR (400 MHzT CDCI3): 5 = 1.56 (tr 3H. CH3): 1.59 - 2.09 (m. 12R 6 x CH2): 2.64 (sr 3H. CH3): 3.45 (m. 1H. CH): 4.24 (g. 2H: CH2): 4.38 (s. 2H. CH2); 7.08 (d. 1H); 7.45 (dd. 1H): 8.09 (d. 1H): 9.82 (bs. 1H. NH). Example 106 fT O VN DMF was added dropwise to a suspension of 40 mg (0.11 mmol) of the azide example 102 in 1 ml of DME until a homogeneous solution was formed, and 13.3 mg (O.lo mmol) of methyl propiolate were then added dropwise. The mixture was heated under reflux for 20 h. the solvent was condensed off under high vacuum and 1 ml of H2O was added to the residue. Following filtration tlirough 1 g of Extrelut (mobile phase: ethyl acetate), the concentrated crude product was purified by preparative thin-layer chromatography (CH2C12 : MeOH = 20:1). This gave 24.3 mg (49.4 %) of the desired product as a mixture of regioisomers (12.5 : 1 according to NMR) MS (ESI): m/z (%) = 452 [ M + H ] (100) Main regioisomer: 'H-NMR (200 MHz, CDCI3): 5 = 1.03 (t. 3H. CH3). 1.57 (t, 3H, CH3), 1.98 (m, 2H. CH2). 2.64 (s. 3H. CH3). 2.99 (t. 2H. CH2). 3.95 (sr 3H. OCH3)T 4.27 (gs 2H: CH2); 5.62 (s, 2H: CH2): 7.08 (d, 1H), 7.43 (ddr 1H); 8.05 (s, 1H)} 8.11 (d, 1H), 9.79 (bs; 1RNH). The compounds of the table below were prepared in a parallel synthesis analogously to example 106 from the azide example 102. hi each case, a 3-fold excess of alkyne was used. Analogously to example 106. 67 mg (0.18 mmol) of the azide example 103 were heated under reflux with 21.4 mg (0.25 mmol) of methyl propiolaie for 20 h. The crude product was triturated with ether. This gave 29.6 mg (36.2%) of the product which was enriched with the main regioisomer (9.3 : 1 according to NMR). According to LC-MS. the mother liquor contained inter alia more of the regioisomeric product mixture (1 : 1.82). MS (ESI): m/z (%) = 466 [ M + H ] (100) Main regioisomer: 'H-NMR (200 MHz. CDC13): 5 = 1.04 (t. 3H. CH3). 1.35 (t. 3H. CH3)r 1.59 (t. 3H. CH3). 1-88 (m. 2H. CH2). 3.03 (mr 4H: 2 x CH2). 3.96 (s: 3H. OCH3)r 4.27 (g. 2H. CH2), 5.62 (s; 2H. CH2). 7.08 (d, 1H)T 7.43 (ddr 1H)? 8.12 (d. 1H), 9.82 (bs. 1R NH). Example 123 Analogously to example 106. 100 mg (0.25 mmol) of the azide example 104 were heated under reflux with 29.9 mg (0.36 mmol) of methyl propiolate for 20 h. The precipitated solid was filtered off and washed with ether, giving 47.8 mg (39.6%) of the product in the form of the main regioisomer. According to LC-MS, the mother liquor contained inter alia more regioisomeric product mixture (1 : 2.3). MS (ESI): m/z (%) = 492 [ M + H ] (100) Main regioisomer: ]H-NMR (200 MHzr CDC13): 6-1.32 (t. 3H. CH3). 1-58 (t, 3H. CH3). 1.66 - 2.18 (mr 8R 4 x CH2)r 3.03 (g: 2H, CH2). 3.62 (m. 1H. CH). 3.95 (s. 3R OCH3). 4.27 (g; 2H. CH2). 5.63 (s. 2H. CH2). 7.08 (d. 1H) 7.43 (dd. 1H). 8.05 (s, 1H). 8.10 (d. lH)f 9.88 (bs. 1H.NH). Example 124 H3C-Q Analosoush to example 106. 70 mg (0.17 mmol) of the azide example 100 were reacted with 20.3 me (0.24 mmol) of methyl propiolate. The crude product was recrystallized from ether. This gave 24.5 mg (29.2%) of the main regioisomer. According to LC-MS. the mother liquor contained a mixture of the two regioisomers (15 :22). MS (ESI): m/z (%) = 506 [ M + H ] (100) 5 'H-NMR (200 MHz, CDC13): 5-1.22 (t5 3H. CH3); 1.45 - 2.05 (m, 12R 6 x CH2); 2.65 (s; 3Hr CH3)r 3.48 (mr 1H, CH): 3.95 (sr 3Hr OCH3), 4.27 (g, 2H, CH2); 5.63 (s, 2Hr CH2): 7.08 (d; 1H): 7.43 (dd, 1H), 8.05 (s, 1H), 8.10 (d, 1H), 9.87 (bs, 1H.NH). Example 125 10 1 CH3 18.5 mg (0.18 mmol) of N-methylpiperazine were added to a suspension of 20 mg (0.046 mmol) of the phenacyl bromide example 57A in 0.5 ml of 1.2-dichloroethane. and the mixture was heated at 80°C for 4 h. 0.5 ml of sat. NaHC03 solution was 15 added after cooling, and the mixture was worked up by filtration through 500 mg of Extrelut / 500 mg of silica gel (mobile phase: ethyl acetate). The concentrated crude product was purified chromatographically (gradient: CH2CI2 +CH2CI2 : MeOH 10:1 + 5.1). This gave 18.4 mg (88%) of product. MS (ESI): m/z (%) = 453 [ M + H ] (60) 'H-NMR (200 MHz. CDCL3): 5 = 1.05 (t; 3H, CH3), 1.58 (t, 3H: CH3), 1.88 (m; 2H, CH2)r 2.65 (s, 3H. CH3). 2.75 (sr 3R CH3); 3.17 (g. 2H, CH2), 3.17 - 3.25 (m: 8H; 4 x CH2); 3.98 (s5 2H. CH2); 4.35 (g. 2Hr CH2). 7.13 (d, 1H), 8.08 (dd, 1H), 8.70 (d. lH),9.57(bs, 1H.NH) Example 126 A suspension of 25 mg (0.057 mmol) of the phenacy] bromide example 57A and 10 23.8 mg (0.23 mmol) of N-propyl-2-aminoethanol in 0.5 ml of 1.2-dichloromethane was heated at 80°C for 10h. 0.5 ml of sat. NaHC03 solution was added to the reaction mixture, which was then filtered through a biphasic cartridge (upper phase: 500 mg of Extrelut. 500 mg of silica gel) (mobile phase: ethyl acetate). Concentration gave 23.6 mg of crude product which was purified by preparative thin-layer 15 chromatography (CH2C12 : MeOH = 20:1). This gave 9.4 mg (35.8 %) of product. MS (ESI): m/z (%) = 456 (100) [ M + H ] 'H-NMR (200 MHz. CDCL3): 8 = 0.95 (L 3R CH3), 1.03 (L 3H; CH3), 1.43 - 1.68 (m. 5H)r 1.88 (m. 2H). 2.20 - 2.45 (m. 4H). 2.84 (bd. 2H). 3.02 (t. 2H). 4.25 (g. 2H)r 7.03 (d. 1H). 7.75 (dd. 1H). 8.38 (d. 1H). 9.82 (bs. 1H. NH). Example 127 10 I 2 27.7 mg (0.37 mmol) of N-methyl-2-aminoethanol were added to a suspension of 40 mg (0.09 mmol) of the phenacyl bromide example 57A in 0.5 ml of 1.2-dichloroethane. and the mixture was heated at 60°C for 4 h. 1 ml of H2O was added, and the mixture was filtered through 1 g of Extrelut (mobile phase: CH2C12). The crude product was initially purified chromatographically (gradient: CH2C12/Me01-1 40:1 + 10:1). and the product fraction was purified by preparative thin-layer chromatography (CH3C]2/MeOH 20:1). This gave 9.5 mg (24.1%) of the desired product as a mixture of the open-chain form 1 and the cyclized form 2. MS (ESI): m/z (%) - 428 [ M + H ] (100) 15 2: 'H-NMR (200 MHz. CDC13): 5 = 1.03 (lr 3H. CH3): 1.53 (tr 3H. CH3), 1.89 (m. 2H. CH2), 2.22 (i, 2H. CH2), 2.33 (s: 3H. CH3); 2.64 (s, 3H. CH3), 2.78 (bt, 2H: CH2): 3.02 (t 2H. CH2), 3.87 (dd. lH)r 4.19 (ddr 1H). 4.26 (g, 2H, CH2): 7.03 (dT 1H). 7.75 (dd. 1H). 8.38 (d. 1H), 9.79 (bs; 1H. NH). Example 143 10 Initially. 6.4 mg (0.05 mmol) of N-amidinothiourea were dissolved in 2 ml of hot EtOH and added to a hot solution of 21.4 mg (0.05 mmol) of the phenacyl bromide example 57A in 2 ml of CH3CN. and the mixture was heated under reflux for 3 h. After cooling. 0.7 ml of H2O was added, the mixture was filtered through 500 mg of Extrelut / 500 mg of SiO? (mobile phase: 1. ethyl acetate. 2. MeOH). and only the methanol phase was concentrated. The residue was purified by preparative thin-layer chromatography (CH2G2 : MeOH = 5:1). This gave 13.6 mg (60.9%) of the desired product. MS (ESI): m/z (%) - 453 [ M + H ] (100) 'H-NMR (300 MHzr D?COD with suppression of water): 6 = 0.90 (t, 3H? CH3), 1.35 (t. 3H. CH3X 1-75 (rm 2H. CH2). 2.49 (sr 3R CH3). 2.90 (t. 2H. CH2), 4.13 (g. 2H. CH20). 6.90 (s. 1H). 7.10 (d, 1H), 7.89 (dd, lH)r 8.07 (dr 1H). Example 144 A solution of 30 mg (0.07 mmol) of the phenacyl bromide example 57A and 12.7 mg (0.08 mmol) of N-benzylthiourea in DMF was initially heated at 60°C for 3 h, 7 mg 5 (0.07 mmol) of EhN were then added and the reaction mixture was. after a further 10 min. cooled to room temperature. The DMF was condensed off under high vacuum. 1 ml of sat. NaHCCh solution was added to the residue and the mixture was filtered through 1 a of Extrelui (mobile phase: CH2G2). The crude product was purified chromatographically (ethyl acetate : cyclohexane = 85:15). This gave 12.9mg 10 (37.2%) of the desired product. MS (DC! /NH3): m/z (%) = 501 [ M + H ] (100) 'H-NMR (400 MHz. CDCI3): 5 = ] .03 (t. 3H. CH3); 1.58 (tr 3H. CH3). 1.85 (m; 2R CH2)r 2.65 (s. 3R CH3). 2.93 (t, 2Hr CH2); 4.27 (g, 2H. CH20)r 4.96 (s, 2Hr CH2); 5.83 (s, lH)r 6.98 (df lH)f 7.15 - 7.29 (m; 6H), 7.99 (d, 1H). Example 154 In the reaction of example 153, 9.3 mg (34%) of the N-acetylpyrrazole are obtained as a by-product. LC-MS (ESI): m/z (%) = 512 (100%) [M+H] 'H-NMR (200 MHz. CDC13): 6 = 0.92 (t. 3R CH3); 1.32 (t, 3H; CH3); 1.74 (dd; 2H): 2.0 (s, 3H. CH3): 2.85 (tr 2H): 4.15 (g. 2H): 6.89 (sr IH); 7.22 (d. IH): 7.45 - 7.62 (m. 6H); 7.9 - 8.05 (m. 2H): 10.05 (bsr 1R NH); 11.63 (bs. 1H. NH). Example 155 H,C Analogously to example 153. 30 mg (0.08 mmol) of the nitrile example 151 were reacted with 13.5 mg (0.09 mmol) of ethyl 2-hydrazinoacetate at 50°C. After cooling to room temperature. 20 mg of aldehyde-functionalized Wang resin were added, and the mixture was stirred at 70°C for 2 h. 0.5 ml of sat. NaHCO? solution was added. the mixture was filtered through 500 mg of Extrelut / 500 mg of Si02 (mobile phase) and the concentrated crude product was initially purified chromatographically (ethyl acetate : cyclohexane = 5:1) and the product fraction was then purified again by preparative thin-layer chromatography (CH2CI2 : MeOH = 10:1). This gave 4.1 mg (10.8 %) of the desired product, in addition to 3.2 mg (8.4%) of starting material. MS (ESI): m/z (%) = 480 [ M + H ] (100) 'H-NMR (200 MHz: CDC13): 5 = 1.04 (t, 3H, CH3), 1.33 (t, 3R CH3); 1.58 (t, 3H; CH3). 1.89 (m; 2R CH2). 2.65 (s, 3H. CH3), 3.05 (t, 2H. CH2), 3.75 (bs, 2R CH2), 4.26 (g, 4R 2 x CH20). 4.86 (s; 2R NH2)r 5.98 (s, 1H), 7.05 (d, 1H), 7.89 (dd; 1H); 8.43 (dslH)5 9.86 (bsr 1H:NH). Example 156 41 pi (0.42 mmol) of phenylhydrazine were added dropwise to a solution of 150 mg (0.35mmol) of the nitrile example 60A in 3 ml of 2M trifluoroacetic acid in CH2C12. and the mixture was healed under reflux for 15 h. Addition of 3 ml of sat. NaHCCh solution and filtration tlirough 3 g of Extrelut (mobile phase: CH2C12) gave, after concentration under reduced pressure, the crude product, which was purified chromatographically (gradient: CH2C12 + CfyCb/MeOH = 50:1). This gave 149 mg (82%) of the desired product (91.3% pure according to HPLC). MS (DCJ. NH3;: m/z (%) - 524 [M +H j (J 00) 'H-NMR (200 MHz. CDCL3): 5 * ] .60 (t, 3H, CH3), 1.67 (bs, 6H, 3 x CH2), 1.82 - 2.17 (m, 6H, 3 x CH2), 2.76 (s, 3H; CH3), 3.63 (m, 1H. CH), 4.35 (g. 2H, CH2) 5.95 (s, 1H), 6.62 (bs, 2H, NH2), 7.12 (d, 1H), 7.36-7.68 (m, 5H, phenyl), 8.02 (dd, 1H), 8.63 (d, 1H), 10.54 (bs, 1H,NH). Example 157 At room temperature. 23.1 mg (0.21 mmol) of metboxyacety) chloride were added to a solution of 100 mg (0.21 mmol) of the aminopvn'azole example 153 in 2 ml of pyridine, and the mixture was stirred for 1 h. The pyridine was condensed off under high vacuum, 0.5 ml of sat. MaHCOj solution was added to the residue and the resulting precipitate was dissolved using ethyl acetate. The mixture was filtered through 500 mg of Extrelut / 500 mg of SiC>2 (mobile phase: ethyl acetate), and the crude product was recrystallized from ethyl acetate / ether. This gave 14.8 mg (12.8%) of the desired product. A further 55 mg (47.7%) were obtained by recrystallization of the product which precipitated on the cartridge during filtration. MS (ESI): m/z (%) = 542 [ M + H ] (100) 'H-NMR (200 MHz, D6-DMSO): 6 = 0.94 (t. 3H, CH3). 1.33 (t 3H. CH3), 1.74 (m. 2H. CH2). 2.86 (t. 2H. CH2). 3.32 (s. 3H. OCH3). 3.98 (s. 2H. CH2), 4.18 (g, 2H. CH20). 6.91 (s, 1H), 7.25 (d. 1H). 7.35 - 7.63 (m. 5H). 8.00 (m. 2H), 9.93 (bs, 1H. NH). 11.62 (bs. 1H.NH). Example J 58 Analogously to example 157. 25 mg (0.053 mmol) of the aminopyrrazole example 153 were reacted in 0.5 ml of pyridine with 7.3 mg (0.053 mmol) of ethyl oxalyl chloride at room temperature for 4 h. Chromatographic purification (gradient: CH2C12 + CH2C12 : MeOH = 50:1) gave 21.8 mg (71.9%) of the desired product. 10 MS (ESI): m/z (%) = 570 [ M + H ] (100) 'H-NMR (200 MHz. CDC13): 6-1.05 (t. 3H. CH3). 1-43 (t. 3H. CH3). 1.58 (t, 3R CH3), 1.90 (m. 2H. CH2). 2.65 (s. 3H. CH3). 3.04 (t. 2H. CH2). 4.30 (g. 2H. CH20)r 4.42 (g. 2H. CH20). 7.11 (± IH). 7.21 (s. IH), 7.45 - 7.65 (m. 5H)r 8.05 (dd, lH)r 8.60 (d, IH), 9.24 (bs, IH, NH), 9.79 (bs, IH, NH). Example 159 Analogously to example 157. 200 mg (0.43 mmol) of the aminopyrrazole example 153 in 4 ml of pyridine were reacted with 58.1 mg (0.43 mmol) of 2-acetoxyacety] chloride. The crude product was triturated with ether, giving 158 mg (65.1%) of the desired product. MS (ESI): m/z (%) = 570 [ M + H ] (100) 'H-NMR (200 MHz. D6-DMSO): 5 = 0.93 (t. 3H. CH5). 1.33 (t. 3R CH3)r 1.74 (m. 2H. CH2). 2.11 (s. 3H. CH3). 2.53 (s. 3H. CH3). 2.85 (t. 2H? CH2). 4.17 (g? 2H: CH2). 4.65 (s. 2H. CH2). 6.92 (s. 1H). 7.25 (d. ]H). 7.35 - 7.60 (m. 5H). 7.99 (m. 2H). 10.25 (bs. 1H. NH)T 11.63 (bs. 1R NH). Example 160 7.9 mg (0.19 mmol) of LiOH were added to a solution of 90 mg (0.16 mmol) of the amidopyrrazole example 159 in 2 ml of THF / H2O (1:1). and the mixture was stirred at room temperature for 30 min. The mixture was diluted with 1 ml of H2O and Tillered through 5 g of Extrelut (mobile phase: CfyCh)- The crude product was recrystallized from CH2CJ2. giving 49 mg (58.8 %) of the desired product. MS (ESI): m/z (%) - 528 [ M + H ] (3 00) 'H-NMR (200 MHz. D6-DMSO): 5 = 0.93 (t. 3H. CH3). 1.32 (m. 3H. CH3). 1.75 (m: 2H. CH2). 2.84 (t. 2H. CH2). 3.95 (s. 2H. CH2). 4.15 (g. 2H. CH2). 6.91 (s. 1H). 7.22 (d. 1H), 7.33 - 7.68 (m. 5H), 7.98 (mr 2H). Example 161 H3C X^ p F Analogously to example 156. 25 mg (0.068 mmol) of the nitrile example 151 were stin-ed with 14.3 mg (0.081 mmol) of 3-trifluorophenylhydrazine and 0.27 ml (0.135 mmoY) of a 0.5 M solution of irifluoroacelic acid in ] .2-dichloroethane ax room lemperature for 20 h. 0.5 ml of sat. "NaHCO? solution was added and the mixture was filtered through 0.5 g of Extrelut / 0.5g of SiCb (mobile phase: ethyl acetate), and the crude product was then dissolved in 0.5 ml of pyridine, and 157 ul (0.018 mmol) of 2-methoxyacetyl chloride were added. After 3 h at room lemperature. another 1 ml of sat. NaHCO.- was added, the mixture was filtered through 1 g of Extrelut (mobile phase: CHjC^) and the filtrate was concentrated under reduced pressure. Purification by thin-layer chromatography (CH2G2: MeOH = 20.1) gave 4.5 mg (40.1%) of the desired product (90% pure according to HPLC). MS (ESI): m/z (%) = 610 [M+H] (100) 'H-NMR (200 MHz. CDCI3): 8 = 1.05 (t. 3H. CH3); 1.57 (t, 3H. CH3); 1.90 (m, 2H, CH2): 2.67 (s. 3B: CB3): 3.07 {1. 2H. CH2): 3.47 (s. 3H. OCH5): 4.06 (s, 2H: CH2): 4.32 (g. 2H. CH2); 7.05 - 7.13 (m. 2H): 7.61 - 7.87 (m. 4H): 8.03 (dd, 1H); 8.59 (d. 1H); 8.68 (bs. 1H.NH); 9.88 (bs. 1H.NH). The compounds of the table below were prepared in a parallel synthesis analogously to example 161 from the nitrile example 151. the appropriate hydrazine and 2-methoxyacety] chloride. Example 168 2-f2-Ethoxy-5-(2-oxirany])pheny])-5-methy]-7-n-propy]oH-imidazof5.]-f)[].2.4]-triazin-4-one 57 mg (1.5 mmol) of NaBH4 (evolution of gas) and 1 ml of 2 N NaOH were added to a suspension, cooled to -20°C of 500 mg (1.12 mmol) of the phenacyl bromide example 57A in 2 ml of THF. The frozen solution was warmed to 0°C and stirred for 30 min. Addition of 10% strength acetic acid (strong evolution of gas) and two extractions with ethyl acetate gave, after drying of the extracts over MgS04 and concentration under reduced pressure, the crude product, which was purified chromatographically (gradient: CH2C13 : MeOH from 100% to 100:] + 50:1 + 30:1). The produci fraction was concentrated and then triturated with ether, giving 221.7 mg (54.2%) of the epoxide. MS (DC1. NH3): m/z (%) = 355 [ M + H ] (57) 'H-NMR (300 MHz. D?COD): 6 = 0.98 (t. 3H. CH3). 1.44 (t. 3H. CH3). 1.83 (m. 2H. CH2); 2.57 (s: 3H. CH3), 3.98 (t. 2H. CH2), 3.55 - 3.75 (m, 2H). 4.19 (g, 2R CH2): 4.87 (m, 1H), 7.17 (d, 1H). 7.58 (dd. 1H): 7.78 (d, 1H). Example 169 2-(2-Ethoxy-5-(2-oxiranyl)phenyl)-5-methyl-7-cycloheptyl-3H-imida2o[5.1-f][l,2.4]-triazin-4-one 20.2 mg (0.53 mmol) of NaBH4 (evolution of gas) and 2 ml of N NaOH solution were added to a suspension, cooled to -20°C. of 200 mg (0.41 mmol) of the phenacy] bromide example 60A in 0.8 ml of EtOH / 0.8 ml of THF. The mixture was allowed to warm to 0°C and. after 30 min. a 10% strength solution of glacial acetic acid was added (strong evolution of gas), the mixture was extracted with ethyl acetate and the extract was dried over MgSOo. The mixture was concentrated and the residue was purified chromaiographically (gradient: CH2CI2 : MeOH = 50:1). This gave 29 mg (17.3%) of the desired product and 104 mg (54%) of the ring-opening product example 170. MS (DC1. NH3): m/z (%) = 409 [ M + H ] (53) 'H-NMR (400 MHz. D?COD): 5-1.43 (t. 3H. CH3). 1.55 - 2.05 (rm 12H. 6 x CH2)r 2.57 (s. 3H. CH3). 3.45 (m. 1H. CH). 3.71 (2 x dd. 2H). 7.17 (d. 1H). 7.57 (dd. 1H). 7.78 (d:lH). Example 170 Ring-opening product: Analogously to example 171 .100 mg (0.28 mmol) of the epoxide example 168 were heated under reflux with 0.91 ml (5.6 mmol) of 1 -phenyl-3-butylamine in 2.5 ml of isopropanol for 24 h. After concentration under reduced pressure, the two regioisomers were separated by preparative chromatography. This gives 51.8 mg (36.5%) as second fraction MS (ESI): m/z (%) = 504 [ M+ H ] (100) 'H-NMR (200 MHz. CDCL3): 5 = 1.02 (t. 3H. CH3), 1.15 (d, 3H, CH3), 1.56 (t, 3H. CH3). 1.62 - 1.95 (m: 4H, 2 x CH2). 2.64 (s. 3H, CH3): 2.68 (m. 2H), 3.01 (m, 3H). 4.25 (g, 2H, CH2), 4.64 (dd, IH, CHO), 7.03 (d. IH). 7.12 - 7.33 (m, 5R phenyl), 7.53 (dd, IH), 8.09(d, IH) Example 174 In the reaction example 173. as first fraction. 21.4 mg (15.1%) of the regioisomer are obtained as a by-product. MS (ESI): m/z (%) = 504 [ M+ H ] (100) 'H-NMR (200 MHz, CDCL3): 5 = 0.93 -1.13 (m, 9H. 3 x CH3). 1.57 (t, 3H. CH3), 1.63 - 1.97 (mr 4H: 2 x CH2). 2.65 (s: 3Hr CH3). 2.65 (m. IH, CH), 2.99 (g, 2H, CH3). 3.42 - 3.75 (m, 2H). 3.92 (m, IH). 4.25 (g. 2H. CH2), 7.01 (d, IH), 7.05 - 7.44 (m. 6H). 8.04 (dd, IH), 9.90 (bs, IH. NH) Example 175 Analogously to example 171. 100 mg (0.28 mmol) of the epoxide example 168 were reacted with 0.48 ml (5.6 mmol) of isopropylamine. After chromatographic pre- purification (gradient: CH2C12 + CH2C12 / MeOH = 10:1). 77.9 mg (67%) of the regioisomer mixture were separated by preparative HPLC. 10 mg (8.6%) are obtained as second fraction. MS (ESI): m/z (%) = 4.14 [M+H] (65) 'H-NMR (200 MHz. CDCL3): 5 =1.03 (t. 3H. CH3). 1.09 (d. 6H. 2 x CH3)r1.55 (t. 3H. CH3). 1.88 (mf 2H: CH2): 2.64 (s. 3H. CH3)r 2.66 (dd, 1R). 2.88 (mr 1R CH); 2.95 (m. 3H. CH. CH2). 4.25 (g, 2H. CH2). 4.69 (dd. ]H)S 7.03 (d, 1H), 7.52 (dd, 1H). 8.09 (d. 1H). Example 176 In the reaction example 175. as first fraction. 20 mg (8.6%) of the regioisomer are obtained as a by-product. MS (ESI): m/z (%) = 414 [ M + H ] (65) 'H-NMR (200 MHzr CDCL3): 5 =1.04 (t, 3R CH3)r 1.07 (2 x d: 6H, 2 x CH3), 1.55 (t. 3H. CH3): 1.88 (m. 2H. CH2): 2.62 (s, 3H\ CH3). 2.75 (m. 1H: CH), 3.02 (t. 2H. CH2): 3.49 (dd. 1H). 3.72 (dd. 1H). 3.94 (dd. 1H). 4.25 (g. 2H. CH2)T 7.03 (d. 1H). 7.43 (dd:lH). 8.04 (d, 1H) A solution of 20 mg (0.05 mmol) of the epoxide example 169 and 589 mg (0.98 mmol) of isopropvlamine in 0.5 ml of isopropanol was heated at 80°C for 20 h. The mixture was concentrated and the residue was then purified by preparative thin- layer chromatography. This gave 15 mg (65.5%) of the desired product as a mixture of two regioisomers. MS (DCI, NH3): m/z (%) - 468 [ M + H ] (100) Main regioisomer: 'H-NMR (400 MHz, CDC13): 5 = 1.25 (2 x d, 6R 2 x CH3), 1.55 (t, 3R CH3), 1.57 - 2.10 (m, 12R 6 x CH2). 2.64 (s, 3H. CH3), 2.83 (dd, 1H). 3.08 (m, 2H), 3.43 (m, 1R CH), 4.23 (g, 2R CH20), 4.95 (dd, 1H. CH), 7.01 (d: 1H), 7.55 (dd, 1H), 8.10 (d: 1H). 2nd Regioisomer: 'H-NMR (400 MHz, CDC13): 5-1.12 (2d, 6H. 2 x CH3), 1.53 (t, 3R CH3), 1.57 - 2.10 (m. 12R 6 x CH2), 3.43 (m, 1H. CH).3.62 (dd. 1H); 3.75 (dd, 1H), 4.00 (dd, 1H). 4.23 (g. 2H. CH20), 7.03 (d, 1H). 7.50 (dd, 1H). 8.06 (d. 1H). Example 179 2-(2-Ethoxy-5-carboxy]phenyl)-5-methy]-7-n-propy]-3H-imidazo[5,l-fJ [1,2,4]-triazin-4-one CR O 1.1 g (6.9 mmol) of bromine, dropwise, and then 1 g (2.3 mmol) of the phenacyl bromide example 57A, a little at a time, were added at 10°C to a solution of 1.8 g (46 mmol) of NaOH in 10 ml of RO. The mixture was allowed to slowly warm to room temperature and, after 2 h, diluted with water and extracted once with CH2CI2. The aqueous phase was then acidified (pH 1) and extracted twice with CH2CI2 and five times with ethyl acetate. The organic phase was dried over MgS(>4 and concentrated under reduced pressure, and the residue was purified chromatographically (gradient: CRCl? + CH2C12 : MeOH = 20:1). The product fraction was once more triturated with CH2CI2. This gave 146 mg (17.8 %) of the desired product. MS (DCI, NH3): m/z (%) = 357 [ M + H ] (100) 'H-NMR (200 MHz, D6-DMSO): 5 = 0.94 (t, 3H, CH3), 1.35 (t, 3H; CH3), 1.75 (m, 2R CH2): 2.84 (t, 2H; CH2). 4.18 (g, 2H, CH2), 7.25 (d, 1H), 7.99 (dd, 1H), 8.10 (d, 1H). 11.62 (bs. 1H.NH), 12.92 (bs, 1H. COOH). Example 180 5.1 mg (0.04 mmol) of N-ethylpiperazine. 18 mg (0.06 mmol) of o-(benzotriazol-l-yl)-N.N.r\r.N'-tetramethy)uronium tetrafluoroborate (TBTU) and 10.8 mg of N-ethyldiisopropylamine were added 10 a solution of 20 mg (0.06 mmol) of the carboxylic acid example 179 in 2 ml of DMF. and the mixture was stirred at room temperature for 1 h. The DMF was condensed off under high vacuum. 0.5 ml of water were added to the residue and the mixture was filtered through a two-phase cartridge (500 mg of Extrelut / 500 mg of Si02, mobile phase: 1. ethyl acetate. 2. CH2C12 : MeOH = 10:1). The CH2C12 / MeOH phase was concentrated, and the residue was separated by preparative thin-layer chromatography. This gave 245 mg (96.5%) of the desired product. MS (DCI, NH3): m/z (%) = 453 [ M + H ] (100) 'H-NMR (400 MHz. D3COD): 6 = 0.98 (t. 3H, CH3)- 1.13 (t, 3H. CH3), 1.45 (t, 3H. CH3). 1.82 (m. 2H). 2.48 (g. 2H. CH2). 2.53 (bs. 4H, 2 x CH2), 2.57 (s. 3H, CH3), 2.95 (t. 2H. CH2). 3.45 (m. 4H. 2 x CH2). 4.25 (g. 2H. CH2). 7.23 (d. 1H). 7.63 (dd. 1H). 7.78 (d. 1H). Example 181 20 mg (0.06 mmol) of the carboxylic acid example 179 and 5.4 mg (0.06 mmol) of morpholine were added to a suspension, cooled to 0°C, of 77.8 mg (0.06 mmol) of polymer-bound N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDC) in 3 ml of CHCI3. The mixture was allowed to warm to room temperature overnight and then heated under reflux for 20 h. 1 ml of sat. MaHCO? solution was added and the mixture was filtered through 1 g of Extrelut (mobile phase: CH2G2). The concentrated residue was purified by preparative thin-layer chromatography (CH2G2 : JvleOH = 20:1). This gave 3.5 mg (14.7 %) of the desired product. MS (ESI): m/z (%) = 426 [ M + H ] (100) 'H-NMR (200 MHz: CDC13): 5 = 1.03 (t. 3H. CH3). 3.59 (t: 3R CH3), 1.87 (m, 2H; CH2); 2.64 (s. 3H. CH3)? 2.99 (t; 2H. CH2). 3.55 - 3.81 (m. 8H. 4 x CH2), 4.31 (g. 2R CH20). 7.10 (dr 1H). 7.62 (dd, 1H). 8.25 (d 1H), 9.89 (bs. 1 H: NH). Example 182 Analogously to example 181, 10 mg (0.03 mmol) of the carboxylic acid example 179 were reacted with 3.1 mg (0.031 mmol) of N-methylpiperazine and 38.4 mg (0.038 mmol) of polymer-bound EDC. Preparative thin-layer chromatography (CH2C12 : MeOH = 10:1) gave 4.2 mg (34.1%) of the desired product. MS (ESI): m/z (%) = 439 [ M + H ] (38) 'H-NMR (200 MHz. CDC13): 5 = 1.02 (1. 3H. CH3). 1.59 (L 3H. CH3). 1.85 (m. 2H. CH2): 2.34 (s; 3H. CH3)r 2.48 (bs. 4R 2 x CH2). 2.63 (s. 3H. CH3). 3.00 (L 2R CH2). 3.65 (bm. 4H. 2 x CH2). 4.31 (g. 2R CH2). 7.09 (d. ]H). 7.60 (dd. 1H). 8.24 (dr IH)r 9.83 (bs. 1H.NH). Example 183 1.7 ml of a 0.1 M solution of SmJ2 (0.17 mmol) in THF were added to a solution of 50 mg (0.12 mmol) of the phenacyl bromide example 57A. and the mixture was heated under reflux for 20 h. Two more times, in each case after 24 h. 1.7 ml of Sm.l2 solution were added. Cooling and filtration through 500 mg of silica gel gave 60 mg of crude product which was purified chromatographically (gradient: CH2CI2 + CH2C12 / MeOH 100:1 + 50:1). This gave 27.6 mg (67.5%) of the desired product (81% according to LC-MS) MS (ESI): m/z (%) = 355 [ M + H ] (100) 'H-NMR (200 MHz, CDC13): 5-1.05 (t. 3R CH3). 1.59 (t, 3R CH3), 1.91 (m, 2R CH2): 2.63 (ss 3R CH3): 2.64 (s.. 3H. CH3)r 3.02 (t. 2R CH2), 4.33 (g, 2R CH2)r 7.11 (d: 1H) 8.12 (dd; lH)r 8.72 (d. 1H). 9.64 (bsr 1RNH) Example 184 Analogously 10 example 183. 50 mg (0.10 mmol) of the phenacyl bromide example 60A were heated under reflux with 5.1 ml (0.51 mmol) of a 0.1 M solution of Sml2 in THF for 10 h. Purification by thin-layer chromatography (CH2C12 : MeOH = 20:1) gave 34.4 mg (34.4 %) of the desired product (94.1% according to HPLC). MS (ESI) m/z (%) = 409 [ M + H ] (100) 'H-NMR (200 MHz, CDCL3). 6 = 1.59 (is 3H. CH3); 1.60 -2.10 (m, 12R 6 x CH2), 2.63 (s. 6H, 2 x CH3). 3.43 (m. ]R CH). 4.33 (g. 2H. CH2)T 7.11 (d. 1H). 8.12 (dd, 1H), 8.72 (d. 1H), 9.82 (bs. 1R NH) Example 185 HX 0 HN A suspension of 180 mg of the epoxide example 40A (0.44 mmol) in 3.5 ml of isopropanol is slowly added to a solution of 1.9 ml of isopropylamine (21.9 mmol) in 1.5 ml of isopropanol. Immediately, a clear yellow solution is formed. After stirring overnight, the precipitated solid is filtered off with suction, washed with a little isopropanol and with petroleum ether and dried under high vacuum. Yield: 83.6 mg (39.9% of theory) MS (DC1. NH3): m/z (%) = 470 (M+H) (100) 'H-NMR (400 MHz. D4-MeOD): 5=1.11 (t. 6 H): 1.42 (t. 3 H); 1.70-1.78 (m, 2 H): 1.86-1.95 (m. 4 H): 2.10-2.18 (m. 2 H): 2.58 (s. 3 H): 2.69 (dd. 1 H): 2.85-2.90 (m. 2 H): 3.66 (qui, 1 H); 3.96-4.07 (m. 3 H): 4.14 (2 H): 7.09-7.17 (m. 2 H): 7.38 (d. 1 H). Example 186 lert-Butylamine (2.6 ml. 25 mmol) is initially charged in 1.5 ml of isopropanol, and the mixture is cooled to 0°C. A suspension of 205 mg of the epoxide example 40A (0.5 mmol) and 3.5 ml of isopropanol is then added. With stirring, the mixture is allowed to warm to room temperature and then stirred overnight. The mixture is concentrated using a rotary evaporator and the residue is purified by column chromatography using dichloromethane/methanol/ammonia solution 95:5:1. Yield: 177 mg (73% of theory) MS (ESl-pos): m/z (%) = 484 (M+H) (100), 428 (68), 325 (21) 'H-NMR (400 MHz: D4-MeOD): 5 - 1.15 (s. 9 H); 1.42 (t, 3 H); 1.68-1.78 (m, 2 H); 1.85-1.98 (m, 4 H): 2.07-2.16 (m. 2 H): 2.55 (s: 3 H); 2.68-2.81 (m, 2 H); 3.55 (qui, 1 H): 3.95-4.05 (m, 3 H): 4.14 (q, 2 H); 7.09-7.17 (2 H); 7.48 (d, 1 H). Example 187 A suspension of 205 mg of the epoxide example 40A (0.5 mmol) in 3.5 ml of isopropanol is added to an ice-cooled solution of l-methyl-3-phenylpropylamine (1.2 ml. 7.5 mmol) in 1.5 ml of isopropanol. With stirring, the mixture is allowed to warm to room temperature and then stirred overnight. Following concentration, the crude product is purified by column chromatography using dichloromethane/methanol/ammonia solution 97:3:1. The product fractions are concentrated using a rotary evaporator and the resulting residue is crystallized with ether. The product is filtered off with suction and dried under high vacuum. Yield: 192 mg (67.7% of theory) MS (DC1. NH3): m/z (%) = 560 (M+H) (100) ]H-NMR (200 MHz. D4-MeOD): 5 = 1.15 (d. 3 H): 1.42 (t, 3 H); 1.55-2.20 (m, 10 H): 2.55-3.92 WE CLAIM : 1. Imidazotriazinones of the following general formula (I) (I), in which R1 represents (Ci-C6)-alkyl, R2 represents (C3-C8)-cycloalkyl or (Ci-Ci2)-alkyl, R3 represents (Ci-CeJ-alkyl, R4 represents a radical of the formula -NH-CO-NR17 R18, in which R17 and R18 are identical or different and represent hydrogen or (Ci-Ce)-alkyl which is optionally substituted by hydroxyl or by a radical of f formulae or -NR19R20 in which R19 and R20 are identical or different and represent hydrogen, phenyL or (C1-C6)-alkyl or R17 and R18 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R21 represents hydrogen or (Ci -C6)-alkyl, a represents either 1 or 2 R22 represents hydroxyl or (Ci-C6)-alkyl which is optionally substituted by hydroxyl, or RW and/or R18 represent (C6-C12)-aryl which is optionally substituted by halogen trifluoroethyl or by -SCF3 or R17 represents hydrogen and R18 represents a radical of the formula -SO2-R23, in which R23 represents (C1-C6)-alkyl or (C6-C12)-aryl which is optionally substituted by halogen or represents a radical of the formulae and its tautomers and its pharmaceutically acceptable salts, hydrates and prodrugs. 2. Imidazotriazinones of the general formula (I) as claimed in claim 1, where R1 represents (C1-C4)-alkyl, R2 represents cyclopentyl, cycloheptyl or (C1-C10)-alkyl, R3 represents (C1-C4)-alkyl. R4 represents a radical of the formula -NH-CO-NR17R18, in which R17 and R18 are identical or different and represent hydrogen or (C1-C4)-alkyl which is optionally substituted by hydroxyl or by a radical of formulae in which R19 and R20 are identical or different and represent hydrogen, phenyl or (C1-C4)-alkyl or R17 and R18 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R21 represents hydrogen or (C1-C4)-alkyl a represents either 1 or 2 R22 represents hydroxyl or (C1-C4)-alkyl which is optionally substituted by hydroxyl, R17 and/or R18 represent phenyl which is optionally substituted by chlorine, trifluoroethyl or by -SCF3 or R17 represents hydrogen and R18 represents a radical of the formula -SO2-R23, in which R23 represents (C1-C4)-alkyl or phenyl which is optionally substituted by halogen, or represents its a radical of the formulae and its tautomers and its pharmaceutically acceptable salts, hydrates and prodrugs, 3. Imidazotriazinones of the general formula (I) as claimed in claim lor 2, where R1 represents (C1-C4)-alkyl, R2 represents cyclopentyl, cyclohexyl, cycloheptyl or (C1-C10)-alkyl, R3 represents (C1-C4)-alkyl, R4 represents a radical of the formula -NH-CO-NR17R18 in which R17 and R18 are identical or different and represent hydrogen or (C1-C4) -alkyl which is optionally substituted by hydroxyl, or R17 and R18 together with the nitrogen atom to which they are attached form a heterocyclic ring of the formulae in which R21 represents hydrogen or (C1-C4)-alkyl, or R17 and/or R18 represent phenyl which is optionally substituted by chlorine, trifluoroethyl or by -SCF3 or R17 represents hydrogen and R18 represents a radical of the formula -SO2-R23. in which R23 represents (C1-C4)-alkyl or phenyl which is optionally substituted by halogen, or represents a radical of the formulae and its tautomers and its pharmaceutically acceptable salts, hydrates and prodrugs, 5. Compounds of the general formula (I) as claimed in any of claims 1 to 4 for the prophylaxis and/or treatment of disorders. 6. Process for preparing imidazotriazinones as claimed in any of claims 1 to 4, characterized in that [A] in the case that R4 is a radical as defined above which is attached via a nitrogen atom, compounds of the general formula (II) (II), in which R2-R2 and R3 are as defined above are initially converted, by reaction with HNO3/CF3CO2H, into the compounds of the general formula (III) in which R1, R2 and R3 are as defined above, in a next step reduced with Fb/Pd-C to give amines of the general formula (IV) (IV), in which R1, R2 and R3 are as defined above, and finally reacted with compounds of the general formula (V) A-D (V), in which A represents the radicals R17 or R18 listed above under R4, D represents the radicals -NH-CO-Cl, -N=C=0 or -S02-N=C=0, in inert solvents, if appropriate in the presence of a base and/or an auxiliary. Medicament or pharmaceutical composition which comprises at least one compound of the general formula (I) as claimed in any of Claims 1 to 4 and one or more pharmacologically acceptable auxiliaries and carriers, as here in described. Dated this 13th day of August, 2002. (RITIISHKA NEGI) OF REMFRY 85 SAGAR ATTORNEY FOR THE APPLICANTS

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