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US 2004/0167135 A1Published application
Dihydropyrimidines
AssigneeBayer Aktiengesellschaft
InventorsJurgen Stoltefuss, Siegfried Goldmann, Thomas Kramer, Karl-Heinz Schlemmer, Ulrich Niewohner, Arnold Paessens, Erwin Graef, Stefan Lottmann, Karl Deres, Olaf Weber, Jorn Stolting
Life of this patent
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Abstract
The invention relates to compounds of the general formulae (I) and (Ia) 1 The invention furthermore relates to processes for preparing the compounds of the formulae (I) and (Ia) and to their use as medicaments, in particular for the treatment and prophylaxis of hepatitis B.
Claims16
Compounds of the general formula (I)
- 159
- or their isomeric form (Ia)
- 160
- in which
- R1 represents phenyl, furyl, thienyl, triazolyl, pyridyl, cycloalkyl having 3 to 6 carbon atoms or represents radicals of the formulae
- 161
- where the abovementioned ring systems are optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, trifluoromethyl, nitro, cyano, trifluoromethoxy, carboxyl, hydroxyl, (C1-C6)-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—NR9R10, SO2—CF3 and -A-CH2—R11,
- in which
- R6 represents phenyl which is optionally substituted by halogen,
- R7, R1, R9 and R10 are identical or different, and each represents hydrogen, phenyl, hydroxyl-substituted phenyl, hydroxyl, (C1-C6)-acyl or (C1-C6)-alkyl, which for its part may be substituted by hydroxyl, (C1-C6)-alkoxycarbonyl, phenyl or hydroxyl-substituted 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, (C1-C6)-alkyl and (C1-C6)-alkoxy,
- R2 represents a radical of the formula —XR12 or —NR13R14,
- in which
- X represents a bond or oxygen,
- R12 represents hydrogen, straight-chain or branched (C1-C6)-alkoxycarbonyl or a straight-chain, branched or cyclic saturated or unsaturated (C1-C6)-hydrocarbon radical which optionally contains one or two identical or different hetero chain members from the group consisting of O, CO, NH, —NH—(C1-C4)-alkyl, —N-((C1-C4)-alkyl)2, 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 —NR15R16,
- in which
- R15 and R16 are identical or different, and each represents hydrogen, benzyl or (C1-C6)-alkyl,
- R13 and R14 are identical or different, and each represents hydrogen, (C1-C6)-alkyl or cycloalkyl having 3 to 6 carbon atoms,
- R3 represents hydrogen, amino or
- represents a radical of the formula
- 162
- or
- 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, (C1-C6)-alkoxycarbonyl, a 5- to 7-membered heterocyclic ring, (C1-C6)-alkylthio and (C1-C6)-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 (C1-C6)-alkoxycarbonyl,
- and/or may be substituted by groups of the formulae —OSO2—CH3 or (CO)a—NR R18,
- 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 (C1-C6)-alkyl which is optionally substituted by (C1-C6)-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, (C1-C6)-alkyl and (C1-C6)-alkoxy,
- or (C1-C6)-alkyl is optionally substituted by groups of the formulae NH—CO—CH3 or NH—CO—CF3, 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
- 163
- R4 represents hydrogen, (C1-C4)-alkyl, (C2-C4)-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, (C1-C6)-alkoxy, (C1-C6)-alkyl, (C1-C6)-alkylthio, carbalkoxy, (C1-C6)-acyloxy, amino, nitro, mono- and (C1-C6)-dialkylamino,
- and salts thereof.
37 more elements
Compound of the formula:
- 185
- and salts thereof.
Compound of the formula:
- 186
Dependencies are inferred from the claim text.