Title of Invention	NOVEL DIHYDROPYRIMIDINE COMPOUNDS OF THE GENERAL FORMULA ( I )
Abstract	"NOVEL DIHYDROPYRIMIDINE COMPOUNDS OF THE GENERAL FORMULA Novel dihydropyrimidine compounds of the general formula (I) or their isomeric form (la)

Full Text

FORM 2 THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS RULES, 2003 COMPLETE SPECIFICATION [See Section 10; rule 13] "NOVEL DIHYDROPYRIMIDINE COMPOUNDS OF THE GENERAL FORMULA (I)" BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Germany, of D-51368 Leverkusen, Germany, GRANTED 15-11-2007 The following specification particularly describes the invention and the manner in which it is to be performed: ORIGINAL 200/MUMNP/2003 The present invention relates to novel dihydropyrimidine compounds of the general formula (I). ' The present invention relates to novel dihydropyrimidine compounds, to processes for their preparation and to their use as medicaments, in particular for the treatment and prophylaxis of hepatitis B. Dihydropyrimidines having cardiovascular action are already known from the publication EP 103 796 A2. The present application describes dihydropyrimidine compounds (claims 1-7), method for the production thereof (claim 8), medicament containing one of the claimed dihydropyrimidines (claim 9). None of the compounds covered by claims 1-7, 9 and 10 is known from the prior art. The claimed compounds (I) and (la) differ from the compounds disclosed in Examples 23 and 24 of Dl in that the substituent in position 2 of the dihydropyrimidine ring is a substituted pyridyl, whereas the known compounds have a non-substituted pyridyl residue in position 2. The technical problem addressed by the present application was that of providing substances suitable for use as active agent in the treatment of hepatitis B infection. Since the dihydropyrimidine compounds disclosed in Dl are only known to have an effect on the cardiovascular system, the special physiological effect of the present compounds (i.e. their suitability for use as agents in the treatment of hepatitis B infections) is surprising, and it would not have been obvious for an expert to consider using dihydropyrimidine derivatives to resolve the technical problem addressed by the application. The present invention now provides novel dmydropyrimidine compounds of the general formula (I) or their isomeric form (la) in which Rl represents phenyl, furyl, thienyl, triazolyl, pyridyl, cycloalkyl having 3 to 6 carbon atoms or represents radicals of the formulae Le A 32 792-Foreign Countries or where the abovementioned ring systems are optionally mono- or polysub-stituted by identical or different substituents selected from the group con¬sisting of halogen, trifluoromethyl, nitro, cyano, trifluoromethoxy, carboxyl, hydroxyl, (C1C6)-alkoxy, (C1-C6)-alkoxycarbonyl and (C1-C6)-alkyl, which for its part may be substituted by aryl having 6 to 10 carbon atoms or halogen, and/or the ring systems mentioned are optionally substituted by groups of the formulae -S-R6, NR7R8, CO-NR'R10, S02-CF3, and -A-CH2-R11, in which R6 represents phenyl which is optionally substituted by halogen, R7, R8, R9 and R10 are identical or different, and each represents hydrogen, phenyl, hydroxyl-substituted phenyl, hydroxyl,acyl or alkyl, which for its part may be substituted by hydroxyl, (C,-C6)-alkoxycarbonyl, phenyl or hydroxyl-substituted phenyl, A represents a radical R" represents phenyl which is optionally mono- to polysubstituted by identical or different substituents selected from the group consisting of halogen, nitro, trifluoromethyl, alkyl and alkoxy, Le A 32 792-Foreign Countries R2 represents a radical of the formula in which X represents a bond or oxygen, R12 repesents hydrogen, straight-chain or branched ilkoxycarb- onyl or a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon radical which optionally contains one or two identical or different hetero chain members from the group consisting of alkyl, alkyl)2, S and S02 and which is optionally substituted by halogen, nitro, cyano, hydroxyl, aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10 carbon atoms, heteroaryl or a group of the formula -NR,5R16, in which R15 and R16 are identical or different, and each represents hydrogen, benzyl or alkyl, R13 and R14 are identical or different, and each represents hydrogen, alkyl or cycloalkyl having 3 to 6 carbon atoms, R3 represents hydrogen, amino or represents a radical of the formula represents formyl, cyano, trifluoromethyl or pyridyl, or represents a straight-chain, branched or cyclic saturated or unsaturated hydro¬carbon radical having up to 8 carbon atoms which is optionally mono- or Le A 32 792-Foreign Countries polysubstituted by identical or different substituents from the group con¬sisting of aryloxy having 6 to 10 carbon atoms, azido, cyano, hydroxyl, carboxyl, alkoxycarbonyl, a 5- to 7-membered heterocyclic ring, alkylthio and alkoxy, which for its part may be substituted by azido or amino, and/or is substituted by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or may be substituted by groups of the formulae NRl7R18, in which a represents a number 0 or 1, R17 and RIS are identical or different, and each represents hydrogen or aryl, aralkyl having 6 to 10 carbon atoms, or represents -alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted by identical or different sub¬stituents from the group consisting of hydroxyl, carboxyl, (C|-C6)-alkyl and _ alkoxy, or alkyl is optionally substituted by groups of the formulae or R17 and R18 together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy, Le A 32 792-Foreign Countries or R2 and R3 together form a radical of the formula R4 represents hydrogen, alkyl, alkenyl, benzoyl or represents acyl having 2 to 6 carbon atoms, Rs represents pyridyl which is substituted up to 3 times by identical or different substituents from the group consisting of halogen, hydroxyl, cyano, trifluoro-methyl, alkoxy, alkyl, alkylthio, carbalkoxy, (C,-C6)- acyloxy, amino, nitro, mono- and iialkylamino, and salts thereof. In the context of the invention, cycloalkyl having 3 to 6 carbon atoms or cyclo- alkyl represents cyclopropyl, cyclopentyl, cyclobutyl or cyclohexyl. Preference is given to cyclopentyl or cyclohexyl. Aryl generally represents an aromatic radical having 6 to 10 carbon atoms. Preferred aryl radicals are phenyl and naphthyl. In the context of the invention, acyl represents a straight-chain or branched acyl radical having 1 to 6 carbon atoms. Preference is given to a straight-chain or branched acyl radical having 1 to 4 carbon atoms. Particularly preferred acyl radicals are acetyl and propionyl. In the context of the invention, alkyl represents a straight-chain or branched alkyl radical having 1 to 6 carbon atoms. Examples which may be mentioned are: methyl, ethyl, propyl, isopropyl, tert-butyl, n-pentyl and n-hexyl. Le A 32 792-Foreign Countries Preference is given to a straight-chain or branched alkyl radical having 1 to 4 carbon atoms. In the context of the invention, alkenyl represents a straight-chain or branched alkenyl radical having 2 to carbon atoms. Preference is given to a straight-chain or branched alkenyl radical having 3 to 5 carbon atoms. Examples which may be mentioned are: ethenyl, propenyl, alkyl, n-pentenyl and n-hexenyl. In the context of the invention, alkoxy represents a straight-chain or branched alkoxy radical having 1 to 6 carbon atoms. Preference is given to a straight-chain or branched alkoxy radical having 1 to 4 carbon atoms. Examples which may be mentioned are: methoxy, ethoxy and propoxy. In the context of the invention, alkylthio represents a straight-chain or branched alkylthio radical having 1 to 6 carbon atoms. Preference is given to a straight-chain or branched alkylthio radical having 1 to 4 carbon atoms. Examples which may be mentioned are: methylthio, ethylthio and propylthio. In the context of the invention, alkoxycarbonyl represents a straight-chain or branched alkoxycarbonyl radical having 1 to 6 carbon atoms. Preference is given to a straight-chain or branched alkoxycarbonyl radical having 1 to 4 carbon atoms. Ex¬amples which may be mentioned are: methoxycarbonyl, ethoxycarbonyl and propoxy-carbonyl. A straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon radical includes, for example, the above-described ilkyl, alkenyl or ;ycloalkyl, preferably alkyl. The compounds according to the invention may exist in stereoisomeric forms which are related either as image and mirror image (enantiomers), or which are not related as image and mirror image (diastereomers). The invention relates both to the enantiomers Le A 32 792-Foreign Countries or diastereomers and to their respective mixtures. The racemic forms can, just like the diastereomers, be separated in a known manner into the stereoisomerically pure constituents. The compounds of the present invention include the isomers of the general formulae (I) and (la) and mixtures thereof. If R4 is hydrogen, the isomers (I) and (la) exist in a tautomeric equilibrium: The substances according to the invention may also be present as salts. In the context of the invention, preference is given to physiologically acceptable salts. Physiologically acceptable salts can be salts of the compounds according to the in¬vention with inorganic or organic acids. Preference is given to salts with inorganic acids, such as, for example, hydrochloric acid, hydrobromoic acid, phosphoric acid or sulphuric acid, or to salts with organic carboxylic or sulphonic acids, such as, for example, acetic acid, maleic acid, fumaric acid, malic acid, citric acid, tartaric acid, lactic acid, benzoic acid, or methanesulphonic acid, ethanesulphonic acid, phenyl-sulphonic acid, toluenesulphonic acid or naphthalenedisulphonic acid. Physiologically acceptable salts can also be metal or ammonium salts of the com¬pounds according to the invention. Particular preference is given to, for example, sodium, potassium, magnesium or calcium salts, and also to ammonium salts which are derived from ammonia, or organic amines, such as, for example, ethylamine, di- Le A 32 792-Foreign Countries or triethylamine, di- or triethanolamine, dicyclohexylamine, dimethylaminoethanol, arginine, lysine, ethylenediamine or 2-phenylethylamine. Preference is given to compounds of the general formulae (I) and (la) according to the invention in which R1 represents phenyl, furyl, thienyl, pyridyl, cyclopentyl or cyclohexyl or repre¬sents radicals of the formulae where the abovementioned ring systems are optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, trifluoromethyl, nitro, methyl, cyano, trifluoromethoxy, amino, hydroxyl, carboxyl, methoxycarbonyl and radicals of the formulae R2 represents a radical of the formula in which X represents a bond or an oxygen atom, Le A 32 792-Foreign Countries R12 represents hydrogen, alkenyl, alkoxycarbonyl or alkyl which are optionally substituted by pyridyl, cyano, phen-oxy, benzyl or by a radical of the formula in which R15 and R16 are identical or different, and each represents hydrogen, benzyl or alkyl, R13 and Ru are identical or different, and each represents hydrogen, alkyl or cyclopropyl, R3 represents hydrogen, amino or a radical of the formula or represents formyl, cyano, trifiuoromethyl, cyclopropyl or pyridyl, or represents (CrC4)-alkyl which is optionally substituted by halogen, (C,-C4)-alkoxycarbonyl, hydroxyl or by triazolyl, which for its part may be substi¬tuted up to 3 times by alkoxycarbonyl, and/or alkyl is optionally substituted by groups of the formulae or in which a represents a number 0 or 1, R17 and Rl8are identical or different, and each represents hydrogen, phenyl or benzyl, or Le A 32 792-Foreign Countries represents alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted by identical or different sub- stituents from the group consisting of hydroxyl, carboxyl, alkyl and alkoxy, and/or alkyl is optionally substituted by radicals of the formulae or R'7 and R18 together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy, or R2 and R3 together form a radical of the formula R4 represents hydrogen, methyl, benzoyl or acetyl, R5 represents pyridyl which is substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, bromoine, alkoxy and alkyl, and salts thereof. Le A 32 792-Foreign Countries Particular preference is given to compounds of the general formulae (I) and (la) according to the invention, in which R1 represents phenyl, furyl, thienyl, pyridyl, cyclopentyl, cyclohexyl or repre¬sents radicals of the formulae where the abovementioned ring systems are optionally substituted up to 2 times by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, trifluoromethyl, nitro, methyl, cyano, amino, trifluoromethoxy, carboxyl, methoxycarb-onyl and radicals of the formulae R2 represents a radical of the formula in which X represents a bond or an oxygen atom, Le A 32 792-Foreign Countries R12 represents hydrogen, alkenyl, alkoxycarbonyl or alkyl which are optionally substituted by pyridyl, cyano, phenoxy, benzyl or by a radical of the formula -NR,5R16, in which R15 and R16 are identical or different, and each represents hydrogen or methyl, R13 and Ru are identical or different, and each represents hydrogen, alkyl or cyclopropyl, R3 represents hydrogen, amino or represents a radical of the formula or represents formyl, cyano, trifluoromethyl, cyclopropyl or pyridyl, or represents alkyl which is optionally substituted by fluorine, chlorine, ilkoxycarbonyl, hydroxyl or by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or alkyl is optionally substituted by groups of the formulae or in which a represents a number 0 or 1, R17 and R18 are identical or different, and each represents hydrogen, phenyl or benzyl, or Le A 32 792-Foreign Countries represents alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or ben2yl, where phenyl or ben2yl are optionally mono- or disubstituted by identical or different substitu-ents from the group consisting of hydroxyl, carboxyl, alkyl and alkoxy, and/or or R17 and RIS together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy, or R2 and R3 together form a radical of the formula - R4 represents hydrogen, methyl, benzoyl or acetyl, R5 represents pyridyl which is substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, ilkoxy and alkyl, and salts thereof. Le A 32 792-Foreign Countries Very particular preference is given to compounds of the general formulae (I) and (la) according to the invention, in which R1 represents phenyl which is optionally substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, methyl and nitro, R2 represents in which X represents oxygen and R12 represents straight- chain or branched alkyl having up to 4 carbon atoms, R3 represents methyl, ethyl or cyclopropyl, or R2 and R3 together form a radical of the formula R4 represents hydrogen or acetyl, and R5 represents pyridyl which is substituted up to two times by identical or differ¬ent substituents from the group consisting of fluorine and chlorine, and salts thereof. Even more preference is given to compounds of the general formula (I) or (la) ac¬cording to the invention in which R5 represents 2-pyridyl which can be substituted by 1 to 2 fluorine atoms. Le A 32 792-Foreign Countries Very particular preference is also given to those compounds of the general formulae (I) and (la) according to the invention which are listed in Table A: Table A: Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Table A: (Continued) Le A 32 792-Foreign Countries Table A: (Continued) Very particular preference is given to the following compounds: Le A 32 792-Foreign Countries The compounds of the general formula (I) according to the invention can be prepared 5 by [A] reacting aldehydes of the general formula (II) in which 15 with amidines or their hydrochlorides of the formula (III) in which Le A 32 792-Foreign Countries in which R2 and R3 are each as defined above, if appropriate in the presence of inert organic solvents, with or without addition of base or acid, or [B] reacting compounds of the general formula (V) in which R1, R2 and R3 are each as defined above, with amidines of the general formula (III) in which Le A 32 792-Foreign Countries if appropriate in the presence of inert organic solvents at temperatures between 20°C and 150°C, with or without addition of base or acid, or [C] reacting aldehydes of the general formula (II) in which R' is as defined above, with compounds of the general formula (VI) in which R2 and R3 are each as defined above, and amidines of the general formula (III) as described above, or [D] reacting aldehydes of the general formula (II) with compounds of the general formula (IV) and imino ethers of the general formula (VII) Le A 32 792-Foreign Countries in which is as defined above, and R1 represents alkyl, in the presence of ammonium salts. The processes according to the invention can be illustrated using the following schemes as examples: [A] Solvents which are suitable for all process variants A, B, C and D are all inert organic solvents. These preferably include alcohols, such as ethanol, methanol, iso-propanol, ethers, such as dioxane, diethyl ether, tetrahydrofuran, glycol monomethyl ether, glycol dimethyl ether or glacial acetic acid, dimethyl formamide, dimethyl sulphoxide, acetonitrile, pyridine and hexamethylphosphoric triamide. Le A 32 792-Foreign Countries The reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out between 20 and 150°C, but preferably at the boiling point of the solvent in question. The reaction can be carried out at atmospheric pressure, or else at elevated pressure. In general, the reaction is carried out at atmospheric pressure. The reaction can be carried out with or without addition of base or acid; however, it has been found that a reaction according to the invention is preferably carried out in the presence of relatively weak acids, such as, for example, acetic acid or formic acid. The aldehydes of the general formula (II) used as starting materials are known or can be prepared by methods known from the literature (cf. T.D. Harris and G.P. Roth, J. Org. Chem. 146 (1979), German Offenlegungsschrift 2 165 260, July 1972, German Offenlegungsschrift 2 401 665, July 1974, Mijano et al., Chem. Abstr. (1963), 13 929 c, E. Adler and H.-D. Becker, Chem. Scand. 849 (1961), E.P. Papadopoulos, M. Mardin and Ch. Issidoridis, J. Org. Chem. Soc. 2543 (1956)). The ylidene keto esters of the formula (V) used as starting materials can be pre¬pared by methods known from the literature [cf. G. Jones, "The Knoevenagel Con¬densation", in Organic Reactions, The enaminocarboxylic esters of the formula (VI) and the imino ethers of the general formula (VII) used as starting materials are known or can be prepared by methods known from the literature [cf. S.A. Glickman and A.C. Cope, J. Am. Chem. Soc. The ketocarboxylic esters of the general formula (IV) used as starting materials are known or can be prepared by methods known from the literature [for example Le A 32 792-Foreign Countries D. Bonmann, "Umsetzung von Diketen mit Alkoholen, Phenolen und Mercaptanen", in Houben-Weyl, Methoden der organischen Chemie, Vol. VII/4, 230 ff (1968); Y. Oikawa, K. Sugano and 0. Yonemitsu, J. Org. Chem. 2087 (1978)]. Some of the compounds of the general formula (III) are known, or, in the case where R5 is difluorinated pyridyl, are novel, and they can be prepared by reacting com¬pounds of the formula (VIII) in which R5 is as defined above, in the customary way via the imino ethers and finally with ammonium chloride in methanol [cf. in this context W.K. Fife, Heterocycles 22, 93-96 (1984); T. Sakamoto, S. Kaneda, S. Nishimura, H. Yamanaka, Chem. Pharm. Bull. 33, 565-571 (1986)] or other processes known from the literature, such as, for example, Garigipati, Tetrahedron Lett. pp. 1969-1972, Boere et al., J. Organomet. Chem. 161, Caton et al., J. Chem. Soc. 1204. All process steps are carried out at atmospheric pressure and in a temperature range of from preferably from Thus, the invention also relates to an intermediate of the formula below Le A 32 792-Foreign Countries and its salts from which preferred end products can be prepared. With respect to the salts of this compound, reference is made to the abovementioned acid addition salts and in particular to the hydrochloride. This compound is prepared as described in the examples, and, in this respect, reference is also made to the reaction scheme shown below. The compounds of the formula (VIII) are known per se or can be prepared by known processes similarly to Example I and II by reacting pyridines of the general formula (IX) in which the hydrogen is ortho to the nitrogen and in which R5 is as defined above, initially at from 50 to 150°C, preferably at 100°C, in glacial acetic acid to give the corresponding N-oxides, followed by a reaction with trimethylsilyl cyanide (TMSCN) by processes known from the literature in the abovementioned inert solvents, preferably acetonitrile, THF, toluene at room temperature or at reflux temperature, if appropriate with addition of bases such as triethylamine or DBU, or by replacing, in compounds of the formula (X) in which Y and Z represent the substitution radicals of the pyridyl ring mentioned under R5, the chlorine with cyanide, using cyanides, such as potassium cyanide or copper cyanide, or by reacting, in the case where R5 represents difluoropyridyl, compounds of the formula Le A 32 792-Poreign Countries in which Y' and Z' are identical or different, and each represents chlorine or bromine, with alkali metal or ammonium fluorides, preferably potassium fluoride, by pro¬cesses known from the literature, in polar solvents, such as, for example, polyglycols and ethers thereof, DMSO or sulpholane, if appropriate with addition of phase-trans¬fer catalysts, in a halogen-fluorine exchange reaction. Thus, the invention also relates to a compound of the formula below from which the corresponding amidine intermediate can be prepared in the manner described in the examples: The above process is, with respect to the 3,5-difluoropyridyl compounds, illustrated in an exemplary manner by the following reaction scheme: Le A 32 792-Foreign Countries The antiviral activity of the compounds according to the invention was investigated following the methods described by Sells et al. (M.A. Sells, M.-L. Chen, and G. Acs (1987) Proc. Natl. Acad. Sci. and Korba et al. (B.E. Korba and J.L. Gerin (1992) Antiviral Research The antiviral tests were carried out in 96-well microtitre plates. Only growth medium and Hep served as virus control. Stock solutions of the test compounds (50 mM) were initially dissolved in DMSO, and further dilutions were prepared in the growth medium of HepG2.2.15. The com¬pounds according to the invention, usually in a test concentration of 100 (1st test concentration), were in each case pipetted into the second vertical test row of the microtitre plate and subsequently diluted, by a factor of 2 each time, up to 210-fold, using growth medium plus of foetal calf serum (volume 25 of a Hep cell suspension cells/ml) in growth medium plus foetal calf serum were then added to each well of the microtitre plate. J« Le A 32 792-Foreign Countries The test batch was incubated at days. The supernatant was subsequently siphoned off and discarded, and of freshly prepared growth medium were added to the wells. Once more, the compounds ac¬cording to the invention were added, in each case as a solution 10-fold-concentrated, in a volume of The batches were incubated for another 4 days. Before the supematants were harvested for determining the antiviral effect, the Hep cells were examined under the light microscope or by biochemical de- tection methods (for example Alamar Blue staining or Trypan Blue staining) for cy¬totoxic changes. The supematants were subsequently harvested and, by means of reduced pressure, siphoned onto 96-well dot blot chambers covered with a nylon membane (in accor¬dance with the specifications of the manufacturer). Determination of the cytotoxicity Substance-induced cytotoxic or cytostatic changes in the Hep cells were de- termined as changes in the cell morphology, for example under a light microscope. Such substance-induced changes of the HepG2.2.15 cells in comparison with un¬treated cells could be observed, for example, as cell lysis, vacuolization or changed cell morphology. 50% cytotoxicity means that of the cells have a morphology which is similar to the corresponding cell control. The compatibility of some of the compounds according to the invention was addi¬tionally tested on other host cells, such as, for example, HeLa cells, primary peripheral human blood cells or transformed cell lines, such as H-9 cells. At. concentrations of the compounds according to the invention no cyto- toxic changes were observed. Le A 32 792-Foreign Countries Determination of the antiviral activity After transfer of the supernatants onto the nylon membrane of the blot apparatus (see above), the supernatants of the HepG2.2.15 cells were denatured NaOH), neutralized and washed By incubation of the filters at 120°C for 2-4 hours, the DNA was subsequently baked onto the membrane. Hybridization of the DNA The viral DNA of the treated cells on the nylon filters was usually de- tected using non-radioactive digoxygenin-labelled hepatitis B-specific DNA probes which were in each case in accordance with the specifications of the manufacturer labelled with digoxygenin, purified and used for hybridization. The prehybridization and hybridization was carried out in 5 x SSC, 1 x blocking rea¬gent, 0.1% N-lauroylsarcosine, and 100 af DNA from herring sperm. The prehybridization was carried out at 60°C for 30 minutes and the specific hybridi¬zation was carried out using 20 to 40 ng/ml of the digoxygenated denatured HBV-specific DNA (14 hours, 60°C). The filters were subsequently washed. Determination of HBV DNA by digoxygenin antibodies The digoxygenin-labelled DNA was detected immunologically in accordance with the specifications of the manufacturer: The filters were washed and prehybridized in a blocking agent (in accordance with the specifications of the manufacturer). They were subsequently hybridized for 30 minutes using an anti-DIG antibody linked to alkaline phosphatase. After a washing step, the substrate of alkaline phosphatase, CSPD, was added, incubated with the filters for 5 minutes, subsequently wrapped in plastic film and incubated at 37°C for a further 15 minutes. The chemiluminescence of the Hepatitis B-specific DNA sig- Le A 32 792-Foreign Countries nals was visualized by exposition of the filters on an X-ray film (incubation, de¬pending on the signal strength: 10 minutes to 2 hours). The half-maximum inhibitory concentration inhibitory concentration 50%) was determined as the concentration at which the hepatitis B-specific band was re¬duced by 50% in comparison with an untreated sample by the compound according to the invention. Surprisingly, the treatment of the hepatitis B virus-producing HepG cells with the compounds according to the invention resulted in a reduction of viral DNA in the cell culture supernatant, the viral DNA being released by the cells into the cell cul¬ture supernatant in the form of virions. The compounds according to the invention have a novel unforeseeable and useful action against viruses. Surprisingly, they are antivirally active against hepatitis B (HBV) and are therefore suitable for treating virus-induced diseases, in particular acute and chronically persisting HBV virus infections. A chronic viral disease caused by HBV can lead to clinical pictures of various gravity; as is known, chronic hepati¬tis B virus infection frequently results in cirrhosis of the liver and/or hepatocellular carcinoma. Examples which may be mentioned of areas of indication for the compounds usable according to the invention are: The treatment of acute and chronic virus infections which may lead to an infectious hepatitis, for example infections with hepatitis B viruses. Particular preference is given to the treatment of chronic hepatitis B infections and the treatment of acute hepatitis B virus infection. The present invention encompasses pharmaceutical formulations which, in addition to non-toxic inert pharmaceutically acceptable excipients, contain one or more com- Le A 32 792-Foreign Countries pounds of the formulae (I), (la) or of Table A or which comprise one or more active compounds of the formulae (I), (la) and also encompasses processes for producing these formulations. In the abovementioned pharmaceutical formulations, the active compounds of the formulae (I), (la) .L should be present in a concentration of approximately 0.1- 99.5% by weight, preferably of approximately by weight of the total mixture. The abovementioned pharmaceutical formulations may, in addition to the compounds of the formulae (I), (la) also contain further pharmaceutical^ active com¬pounds. The abovementioned pharmaceutical formulations are produced in a customary manner by known methods, for example by mixing the active compound(s) with the exci-pient(s). In general, it has been found to be advantageous both in human and veterinary medicine to administer the active compound(s) in total amounts of from approximately 0.5 to approximately 500, preferably 1-100 mg/kg of body weight per 24 hours, if appropriate in the form of several individual doses, to obtain the desired results. An individual dose preferably contains the active compound(s) in amounts of from approximately 1 to approximately 80, in particular 1-30 mg/kg of body weight. How¬ever, it may be necessary to deviate from the specified dosages, depending on the nature and the body weight of the object to be treated, the nature and the severity of the disease, the formulation type and the administration of the medicament, and the time or interval within which administration is carried out. Le A 32 792-Foreign Countries Starting materials Example I 3-Fluoropyridine N-oxide mmol) of 3-fluoropyridine are dissolved in 74.00 ml of acetic acid. 22.20 ml of H202 are added, and the mixture is stirred at a bath temperature of 100°C for 7 hours. The mixture is then concentrated to 30 ml, 30 ml of water are added and the mixture is once more concentrated to 30 ml. The solution is stirred with dichlo-romethane, made alkaline by addition of'. the phases are separated and the aqueous phase is extracted twice with dichloromethane, dried and concentrated. Yield; m.p.: Example II 2-Cyano-3-fluoropyridine of the compound from Example I are dissolved in 50 ml of acetonitrile. Under argon, of trimethylsilylnitrile are added, and 12.80 ml of triethylamine are slowly admixed. The solution is stirred under re¬flux for 7 hours and then at room temperature overnight. The solution is then con¬centrated using a water pump, taken up in dichloromethane, shaken with 50 ml of 2N sodium carbonate, washed with water, dried and concentrated. Le A 32 792-Foreign Countries Yield (crude): Column chromatography: methylene chloride to methylene chloride/ethyl acetate 10:1 The oil solidifies! Example HI 2-Amidino-3-fluoropyridine hydrochloride 10.30 g (84.355 mmol) of the compound from Example II are dissolved in 30 ml of methanol. The solution is admixed with a solution of 0.40 g (17.391 mmol) of so¬dium in 65 ml of methanol and stirred at 20°C for 72 hours. 5.44 g (101.682 mmol) of ammonium chloride (ground in a mortar) and 17.39 mmol (1.04 ml) of acetic acid are added and the mixture is stirred at 40°C for 28 hours and cooled. Insoluble salt is filtered off with suction and the filtrate is concentrated, concentrated with acetone and subsequently stirred with acetone, filtered off with suction and washed. Yield: decomp. Example IV 2-cyano-3,5-dichloro-pyridine Le A 32 792-Foreign Countries Method 1: of 3,5-dichloro-pyridine 1-oxide (Johnson et al., J. Chem. Soc. B, are dissolved in 80 ml of and admixed successively with 21.8 ml (0.174 mol) of trimethylsilyl cyanide and 14.6 ml (0.158 mol) of dimethylcarbamoyl chloride and stirred at room temperature for 48 h. The mixture is admixed with 100 ml of a strengthsolution and stirred vigorously for 10 min. The phases are separated, the aqueous phase is extracted once with and the com- bined organic phases are dried and concentrated. The residue is chromatographed over silica gel using CH2C12 and recrystallized from a little methanol. This gives cyano-3,5-dichloro-pyridine Method 2: By the method of Troschuetz, R. et al., J. Heterocycl. Chem. 1996, 33, 1815-1821, 150 ml of diethylene glycol dimethyl ether (diglyme), of 2,3,5-trichloropyridine, of tetraphenylphosphonium bromide, 4.0 g (0.024 mol) of finely powdered potassium iodide and of copper(I) cyanide are added under nitrogen, and the mixture is stirred at reflux for 24 hours. Another 100 ml of diglyme, of tetraphenylphosphonium bromide, of finely powdered KI and (0.838 mol) of are subse- quently added, and the mixture is stirred at reflux for a further 89 hours. The mixture is cooled to room temperature and filtered off with suction, and the filtrate is freed distillatively from most of the diglyme. The residue is taken up in toluene and washed with an aqueous solution of Mohr's salt and then with solution (peroxide test). The mixture is then washed free of diglyme using water and filtered through Celite, the filtrate is dried over and the solution is concentrated. This gives dichloropyridine. Le A 32 792-Foreign Countries 3,5-Difiuoro-pyridine-2-carbonitrile 50 g (0.29 mol) of 3,5~dichloropyridine-2-carbonitrile (Example IV), 33.6 g (0.58 mol) of potassium fluoride and 10 g of polyethylene glycol 8000 are admixed with 125 ml of DMSO and heated at min. After cooling, the product, together with the DMSO, is distilled off under high vacuum, and the distillate is poured into water, extracted with toluene and dried over The product is re- acted further as a solution in toluene. (Rf value: 0.43, cyclohexane/ethyl acetate = 7.3) Example VI 3,5-difluoro-2-pyridinecarboximidamide hydrochloride of ammonium chloride are suspended in 1 1 of toluene and cooled to of trimethylaluminium (2 M in hexane, 0.624 mol) are added drop- wise, and the mixture is stirred at RT until the evolution of methane has ceased. The solution of 3,5-dichloro-pyridine-2-carbonitrile in toluene (solution from Example V) is then added dropwise, and the mixture is then stirred at 80°C overnight. After Le A 32 792-Foreign Countries cooling to from 0 to is added dropwise until the evolution of gas has ceased, the salts are filtered off with suction and washed to with a little MeOH. The mixture is concentrated using a rotary evaporator and the residue is dissolved in 500 ml of and once more filtered off with suction from inor- ganic salts. The mixture is concentrated using a rotary evaporator, giving 23.6 g of 3,5-difluoro-2-pyridinecarboximidamide as hydrochloride (m.p.: 183°C). 'H-NMR (s,broad,4H) ppm. Example VII Methyl 2-acetyI-3-(2-chloro-4-fluorophenyl)-2-propenoate (315mmol) of fluoro-benzaldehyde and of methyl acetoacetate are dissolved in of isopropanol and admixed with 1.7 ml of piperadine acetate. The mixture is stirred at room temperature overnight and then diluted with methylene chloride and extracted with water, dried over sodium sulphate and concentrated. The crude product is reacted further, as cis-trans mixture. Le A 32 792-Foreign Countries Preparation examples Example 1 Ethyl dihydro-pyrimidin- 5-carboxylate of 2-bromobenzaldehyde in 3.00 ml of ethanol are admixed successively with 65.0 mg of ethyl acetoacetate, 91.80 mg of the compound from Example III and 43.06 mg of sodium acetate, and the mixture is boiled for 6 hours. The mixture is cooled, concentrated, dissolved in 2 ml of IN HC1 and 4 ml of > and ethyl acetate, the phases are separated, the organic phase is extracted with 1 ml of IN HC1 and water and the combined aqueous phases are washed with ether. The aqueous phase is made alkaline using dilute ammonia solution, extracted with ethyl acetate, and the organic phase is washed with , dried and concentrated. The resi¬due is dissolved in a little ether and crystallized. The crystals are filtered off with suction, washed with ether and dried at 60°C under reduced pressure. TLC: pure (toluene/ethyl acetate = 4:1) Yield: m.p.: The compounds listed in Table 1 are prepared by the method of Example 1: Le A 32 792-Foreign Countries Table 1: Table 1 (Continued) Table 1 (Continued) Table 1 (Continued) Le A "i'l 792-Foreign Countries Table 1 (Continued) -i"! Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Table 1 (Continued) Le A 32 792-Foreign Countries Example 61 Methyl 4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridinyl)-6-methyl-l,4-dihy-dropyrimidine-5-carboxylate (see table) 4.5 g (23.2 mmol) of 3,5-difluoro-2-pyridinecarboximidamide hydrochloride (Ex¬ample VI) with 7.7 g (30 mmol) of methyl 2-acetyl-3-(2-chloro-4-fluorophenyl)-2-propenoate (Example VII) and 2.3 g (27.9 mmol) of sodium acetate are dissolved or suspended in 120 ml of isopropanol and boiled under reflux for 4 h. The mixture is cooled to room temperature and then filtered off with suction from in¬organic salts and concentrated. The residue is taken up in 30 ml of IN HC1 and 35 ml of ethyl acetate, and the phases are separated. The ethyl acetate phase is re-extracted once using 30 ml of IN HC1. The combined aqueous phases are extracted three times with 10 ml of diethyl ether each time. The aqueous phase is made alkaline using NaOH and extracted with ethyl acetate. The organic phases are dried over Na2S04 and concentrated. This gives of product. t The enantiomer was obtained after separation of the enantiomers on chiral col¬umns (Chiralpak AS from Baker, mobile phase n-heptane/ethanol=8:2). m.p.: 117°C (from ethanol) Spec, rot.: Le A 32 792-Foreign Countries Table 2 Le A 32 792-Foreign Countries Table 2 (continued) Le A 32 792-Foreign Countries Table 2 (continued) Le A 32 792-Foreign Countries Table 2 (continued) Le A 32 792-Foreign Countries Table 2 (continued) Le A 32 792-Foreign Countries Table 2 (continued) Le A 32 792-Foreign Countries Table 2 (continued) Le A 32 792-Foreign Countries Table 2 (continued) melting point in degrees Celsius Le A 32 792-Foreign Countries Patent claims Compounds of the general formula (I) or their isomeric form (la) in which Rl represents phenyl, furyl, thienyl, triazolyl, pyridyl, cycloalkyl having 3 to 6 carbon atoms or represents radicals of the formulae where the abovementioned ring systems are optionally mono- or polysubstituted by identical or different substituents selected from the Le A 32 792-Foreign Countries group consisting of halogen, trifluoromethyl, nitro, cyano, trifluoro-methoxy, carboxyl, hydroxyl, alkoxy, alkoxycarbonyl and ilkyl, which for its part may be substituted by aryl having 6 to 10 carbon atoms or halogen, and/or the ring systems mentioned are optionally substituted by groups of the formulae and in which R6 represents phenyl which is optionally substituted by halogen, R\ R8, R9 and R10 are identical or different, and each represents hydrogen, phenyl, hydroxyl-substituted phenyl, hydroxyl, (C,-C6)-acyl or (C,-C6)-alkyl, which for its part may be substituted by hydroxyl, (C,-C6)-alkoxycarbonyl, phenyl or hydroxyl-substituted phenyl, A represents a radical R" represents phenyl which is optionally mono- to polysubstituted by identical or different substituents selected from the group consisting of halogen, nitro, trifluoromethyl, alkyl and alkoxy, R2 represents a radical of the formula -XR12 or -NR13RU , in which represents a bond or oxygen, Le A 32 792-Foreign Countries R12 represents hydrogen, straight-chain or branched alkoxycarbonyl or a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon radical which optionally contains one or two identical or different hetero chain members from the group consisting of alkyl, alkyl)2, S and and which is optionally substituted by halogen, nitro, cyano, hydroxyl, aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10 carbon atoms, heteroaryl or a group of the formula -NRI5R16, in which R15 and R'6 are identical or different, and each represents hydrogen, benzyl or alkyl, R13 and R14 are identical or different, and each represents hydrogen, alkyl or cycloalkyl having 3 to 6 carbon atoms, R3 represents hydrogen, amino or represents a radical of the formula represents formyl, cyano, trifluoromethyl or pyridyl, or represents a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon radical having up to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of aryloxy having 6 to 10 carbon atoms, azido, cyano, hydroxyl, carboxyl, alkoxycarbonyl, a 5- to 7-membered heterocyclic ring, alkylthio andalkoxy, which for its part may be substituted by azido or amino, Le A 32 792-Foreign Countries and/or is substituted by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or may be substituted by groups of the formulae or in which a represents a number 0 or 1, R17 and R18 are identical or different, and each represents hydrogen or aryl, aralkyl having 6 to 10 carbon atoms, or represents alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted by identical or different substituents from the group consisting of hydroxyl, carboxyl, alkyl and i alkoxy, or ilkyl is optionally substituted by groups of the formulae or R17 and R18 together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy,or Le A 32 792-Foreign Countries R2 and R3 together fonn a radical of the formula R4 represents hydrogen, alkyl, alkenyl, benzoyl or represents acyl having 2 to 6 carbon atoms, R5 represents pyridyl which is substituted up to 3 times by identical or different substituents from the group consisting of halogen, hydroxyl, cyano, trifluoromethyl, alkoxy,alkyl, alkylthio, carbalkoxy, acyloxy, amino, nitro, mono- and dialkylamino, and salts thereof. 2. Compounds of the general formulae (I) and (la) according to Claim 1, in which R1 represents phenyl, furyl, thienyl, pyridyl, cyclopentyl or cyclohexyl or represents radicals of the formulae where the abovementioned ring systems are optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, trifluoromethyl, nitro, methyl, cyano, amino, trifiuoromethoxy, hydroxyl, carboxyl, methoxycarbonyl Le A 32 792-Foreign Countries and radicals of the formulae R2 represents a radical of the formula ■ in which X represents a bond or an oxygen atom, R12 represents hydrogen, alkenyl, alkoxycarbonyl or ilkyl which are optionally substituted by pyridyl, cyano, phenoxy, benzyl or by a radical of the formula in which R15 and RIS are identical or different, and each represents hydrogen, benzyl or alkyl, R13 and R14 are identical or different, and each represents hydrogen, alkyl or cyclopropyl, R3 represesents hydrogen, amino or a radical of the formula or represents formyl, cyano, trifiuoromethyl, cyclopropyl or pyridyl, or represents alkyl which is optionally substituted by halogen, -allcoxycarbonyl, hydroxyl or by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or alkyl is optionally substituted by groups of the formulae in which a represents a number 0 or 1, Rn and R,s are identical or different, and each represents hydrogen, phenyl or benzyl, or represents ilkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted by identical or different substitutents from the group consisting of hydroxyl, carboxyl, i alkyl and , , „, alkoxy, and/or (C,-C4)-alkyl is optionally substituted by radicals of the formulae or R17 and R18 together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy, or Le A 32 792-Foreign Countries R2 and R3 together form a radical of the formula R4 represents hydrogen, methyl, benzoyl or acetyl, R5 represents pyridyl which is substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, bromine, alkoxy and alkyl, and salts thereof. 3. Compounds of the general formulae (I) and (la) according to Claim 1 in which R1 represents phenyl, furyl, thienyl, pyridyl, cyclopentyl, cyclohexyl or represents radicals of the formulae where the abovementioned ring systems are optionally substituted up to 2 times by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, trifluoro-methyl, amino, nitro, , methyl, cyano, trifluoromethoxy, carboxyl, methoxycarbonyl and radicals of the formulae Le A 32 792-Foreign Countries 81 R2 represents a radical of the formula in which X represents a bond or an oxygen atom, R12 represents hydrogen, ^ _, alkenyl, alkoxycarbonyl or ilkyl which are optionally substituted by pyridyl, cyano, phenoxy, benzyl or by a radical of the formula -NR15R16, in which R15 and R16 are identical or different, and each represents hydrogen or methyl, R13 and R14 are identical or different, and each represents hydrogen, alkyl or cyclopropyl, or represents formyl, cyano, trifluoromethyl, cyclopropyl or pyridyl, or R3 represents hydrogen, amino or represents a radical of the formula Le A 32 792-Foreign Countries represents ilkyl which is optionally substituted by fluorine, chlorine, alkoxycarbonyl, hydroxyl or by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or alkyl is optionally substituted by groups of the formulae in which a represents a number 0 or 1, R17 and R18 are identical or different, and each represents hydrogen, phenyl or benzyl, or represents alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or disubstituted by identical or different substituents from the group consisting of hydroxyl, carboxyl, alkyl and alkoxy, and/or ilkyl is optionally substituted by radicals of the formulae or R17 and R18 together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy,or Le A 32 792-Foreign Countries R2 and R3 together form a radical of the formula R4 represents hydrogen, methyl, benzoyl or acetyl, R5 represents pyridyl which is substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, alkoxy and alkyl, and salts thereof. 4. Compounds of the general formulae (I) and (la) according to Claim 1, in which R1 represents phenyl which is optionally substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, methyl and nitro, R2 represents -XR12 in which X represents oxygen and R12 represents straight-chain or branched alkyl having up to 4 carbon atoms, R3 represents methyl, ethyl or cyclopropyl, or R2 and R3 together form a radical of the formula R4 represents hydrogen, or acetyl, and Le A 32 792-Foreign Countries R5 represents pyridyl which is substituted up to two times by identical or different substituents from the group consisting of fluorine and chlorine, and salts thereof. Compounds of the general formulae (I) and (la) according to any of Claims 1 to 4 in which R5 represents 2-pyridyl which is substituted by 1 or 2 fluorine atoms. Compounds according to Claim 1 of the structures below Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries Le A 32 792-Foreign Countries 7. Compounds according to Claim 1 of the structures below: or salts thereof. 8. Process for preparing the compounds according to Claims 1 to 7, characterized in that, [A] aldehydes of the general formula (II) in which is as defined above Le A 32 792-Foreign Countries are reacted with amidines or their hydrochlorides of the formula (III) in which R5 is as defined above, and compounds of the general formula (IV) in which R2 and R3 are each as defined above, if appropriate in the presence of inert organic solvents, with or without ad¬dition of base or acid, or [B] compounds of the general formula (V) in which Le A 32 792-Foreign Countries 97- are each as defined above, are reacted with amidines of the general formula (III) in which R5 is as defined above, if appropriate in the presence of inert organic solvents at temperatures between 20°C and 150°C, with or without addition of base or acid, or [C] aldehydes of the general formula (II) in which R' is as defined above, are reacted with compounds of the general formula (VI) Le A 32 792-Foreign Countries R2 and R3 are each as defined above, and amidines of the general formula (III) as described above, or aldehydes of the general formula (II) are reacted with compounds of the general formula (IV) and imino ethers of the general formula (VII) in which is as defined above, and represents alkyl, in the presence of ammonium salts. and salts thereof. Compound of the formula: Le A 32 792-Foreign Countries 10. Compound of the formula: [11. Medicaments, containing at least one compound of the general formula (I) or (la) according to one of Claims 1 to 7 and, if appropriate, containing further pharmaceutically active compounds. 12. Process for producing medicaments, characterized in that at least one compound of the general formula (I) or (la) according to one of Claims 1 to 7 is converted into a suitable administration form, if appropriate using customary auxiliaries and excipients. A$. Compounds of the general formula (I) or (la) according to one of Claims 1 to 7 for use as medicaments. 14. Use of compounds of the general formula (I) or (la) according to one of Claims 1 to 7 for producing a medicament. 15. Use of compounds of the general formula (I) or (la) according to one of Claims 1 to 7 for producing a medicament for treating acute or chronic viral diseases. 16. Use of compounds of the general formula (I) or (la) according to one of Claims 1 to 7 for producing a medicament for treating acute or chronic hepatitis B infections. We Claim: Novel dihydropyrimidine compounds of the general formula (I) or their isomeric form (la) wherein R1 represents phenyl, furyl, thienyl, triazolyl, pyridyl, cycloalkyl having 3 to 6 carbon atoms or represents radicals of the formulae where the abovementioned ring systems are optionally mono- or poly substituted by identical or different substituents selected from the group consisting of halogen, trifluoromethyl, nitro, cyano, trifiuoromethoxy, carboxyl, hydroxyl, alkoxy, alkoxycarbonyl and alkyl, which for its part may be substituted by aryl having 6 to 10 carbon atoms or halogen, and/or the ring systems mentioned are optionally substituted by groups of the formulae -S-R6, NR7R8, CO-NR9R10, and wherein R6 represents phenyl which is optionally substituted by halogen, R7, R8, R9 and R10 are identical or different, and each represents hydrogen, phenyl, hydroxyl-substituted phenyl, hydroxyl, acyl or alkyl, which for its part may be substituted by hydroxyl, alkoxycarbonyl, phenyl or hydroxylsubstituted phenyl, A represents a radical O, S, SO or SO2, R11 represents phenyl which is optionally mono- to polysubstituted by identical or different substituents selected from the group consisting of halogen, nitro, trifluoromethyl, alkyl and alkoxy, represents a radical of the formula wherein X represents a bond or oxygen, R12 represents hydrogen, straight-chain or branched (Ci-Ce)-alkoxycarbonyl or a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon radical which optionally contains one or two identical or different hetero chain members from the group consisting of -, — Vw. ~-,, alkyl, alkyl)?, S and SO2 and which is optionally substituted by halogen, nitro, cyano, hydroxyl, aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10 carbon atoms, heteroaryl or a group of the formula wherein R15 and R16 are identical or different, and each represents hydrogen, benzyl or alkyl, R13 and are identical or different, and each represents hydrogen, (Ci- alkyl or cycloalkyl having 3 to 6 carbon atoms, R3 represents hydrogen, amino or represents a radical of the formula represents formyl, cyano, trifluoromethyl or pyridyl, or represents a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon radical having up to 8 carbon atoms which is optionally mono- or polysubsututed by identical or different substituents from the group consisting of aryloxy having 6 to 10 carbon atoms, azido, cyano, hydroxyl, carboxyl, alkoxycarbonyl, a 5- to 7-membered heterocyclic ring, alkylthio and alkoxy, which for its part may be substituted by azido or amino, and/or is substituted by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or may be substituted by groups of the formulae or wherein a represents a number 0 or 1, R17 and R18 are identical or different, and each represents hydrogen or aryl, aralkyl having 6 to 10 carbon atoms, or represents alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted by identical or different substituents from the group consisting of hydroxyl, carboxyl, alkyl and alkoxy, or alkyl is optionally substituted by groups of the formulae or R17 and R18 together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy, or R2 and R3 together form a radical of the formula R4 represents hydrogen, alkyl, alkenyl, benzoyl or represents acyl having 2 to 6 carbon atoms, R5 represents pyridyl which is substituted up to 3 times by identical or different substituents from the group consisting of halogen, hydroxyl, cyano, trifluoromethyl, alkoxy, alkyl, alkylthio, carbalkoxy, acyloxy, amino, nitro, mono- and i dialkylamino, and salts thereof. 2. Novel dihydropyrimidine compounds of the general formulae (I) and (la) as claimed in claim 1, wherein R1 represents phenyl, furyl, thienyl, pyridyl, cyclopentyl or cyclohexyl or represents radicals of the formulae where the abovementioned ring systems are optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, trifiuoromethyl, nitro, methyl, cyano, amino, trifluoromethoxy, hydroxyl, carboxyl, methoxycarbonyl and radicals of the formulae R2 represents a radical of the formula wherein X represents a bond or an oxygen atom, R12 represents hydrogen, alkenyl, alkoxycarbonyl or alkyl which are optionally substituted by pyridyl, cyano, phenoxy, benzyl or by a radical of the formula whorein and are identical or different, and each represents hydrogen, benzyl or alkyl, and are identical or different, and each represents hydrogen. alkyl or cyclopropyl, R3 represesents hydrogen, amino or a radical of the formula represents formyl, cyano, trifluoromethyl, cyclopropyl or pyridyl, or represents alkyl which is optionally substituted by halogen, alkoxycarbonyl, hydroxyl or by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or alkyl is optionally substituted by groups of the formulae wherein a represents a number 0 or 1, and are identical or different, and each represents hydrogen, phenyl or benzyl, or represents alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or poly substituted by identical or different substitutents from the group consisting of hydroxyl, carboxyl, alkyl andalkoxy, and/or alkyl is optionally substituted by radicals of the formulae or R17 and R18 together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy, or and R3 together form a radical of the formula R4 represents hydrogen, methyl, benzoyl or acetyl, R5 represents pyridyl which is substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, bromine, alkoxy andalkyl, and salts thereof. 3. Novel dihydropyrimidine compounds of the general formulae (I) and (la) as claimed in claim 1 wherein R1 represents phenyl, fury!, thienyl, pyridyl, cyclopentyl, cyclohexyl or represents radicals of the formulae where the abovementioned ring systems are optionally substituted up to 2 times by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, trifluoromethyl, amino, nitro, SO2-CF3, methyl, cyano, trifluoromethoxy, carboxyl, methoxycarbonyl and radicals of the formulae R2 represents a radical of the formula wherein X represents a bond or an oxygen atom, R12 represents hydrogen, alkenyl, alkoxycarbonyl or alkyl which are optionally substituted by pyridyl, cyano, phenoxy, benzyl or by a radical of the formula wherein and are identical or different, and each represents hydrogen or methyl, R13 and R14 are identical or different, and each represents hydrogen, alkyl or cyclopropyl, R3 represents hydrogen, amino or represents a radical of the formula or represents formyl, cyano, trifluoromethyl, cyclopropyl or pyridyl, or represents alkyl which is optionally substituted by fluorine, chlorine, alkoxycarbonyl, hydroxyl or by triazolyl, which for its part may be substituted up to 3 times by alkoxycarbonyl, and/or alkyl is optionally substituted by groups of the formulae wherein a represents a number 0 or 1, R17 and R18 are identical or different, and each represents hydrogen, phenyl or benzyl, or represents alkyl which is optionally substituted by alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or disubstituted by identical or different substituents from the group consisting of hydroxyl, carboxyl, alkyl and alkoxy, and/or alkyl is optionally substituted by radicals of the formulae or and together with the nitrogen atom form a morpholine, piperidinyl or pyrrolidinyl ring, or R3 represents phenyl which is optionally substituted by methoxy, or R2 and R3 together form a radical of the formula R4 represents hydrogen, methyl, benzoyl or acetyl, R5 represents pyridyl which is substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, alkoxy and alkyl, and salts thereof. 4. Novel dihydropyrimidine compounds of the general formulae (I) and (la) as claimed in claim 1, wherein R1 represents phenyl which is optionally substituted up to 2 times by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, methyl and nitro, R2 represents -XR12 in which X represents oxygen and R12 represents straight-chain or branched alkyl having up to 4 carbon atoms, R3 represents methyl, ethyl or cyclopropyl, or R2 and R3 together form a radical of the formula R4 represents hydrogen, or acetyl, and R5 represents pyridyl which is substituted up to two times by identical or different substituents from the group consisting of fluorine and chlorine, and salts thereof. 5. Novel dihydropyrimidine compounds of the general formulae (I) and (la) as claimed in any of claims 1 to 4 in which R5 represents 2-pyridyl which is substituted by 1 or 2 fluorine atoms. 6. Novel dihydropyrimidine compounds as claimed in claim 1 of the structures below 7. Novel dihydropyrimidine compounds as claimed in claim 1 of the structures below: or salts thereof. 8. A process for preparing novel dihydropyrimidine compounds of the formula (I) as claimed in claims 1 to 7, wherein, [A] aldehydes of the general formula (II) wherein R1 is as defined above, are reacted with amidines or their hydrochlorides of the formula (III) wherein R5 is as defined above, and compounds of the general formula (IV) wherein R2 and R3 are each as defined above, if appropriate in the presence of alcohols, such as ethanol, methanol, isopropanol, ethers, such as dioxane, diethyl ether, tetrahydrofuran, glycol monomethyl ether, glycol dimethyl ether or glacial acetic acid, dimethyl formamide, dimethyl sulphoxide, acetonitrile, pyridine and hexamethylphosphoric triamide, with or without addition of acetic acid or formic acid. 9. Medicaments, containing at least one,compound of the general formula (I) or (la) as claimed in one of claims 1 to 7 present in a concentration of approximately 0.1 to /by weight and, if appropriate, containing further pharmaceutically aclive compounds. Dated this 05/02/2003 JITESH KUMAR OF REMFRY & SAGAR ATTORNEY FOR THE APPLICANT[S]

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