Patent ID: 6362178
Filing Date: 2002-03-26
Classification: A61P,C07D,C07F

Abstract:
A compound of the formula (I) in whichR1 represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, R2 represents straight-chain alkyl having up to 4 carbon atoms, R3 and R4 are identical or different and each represents hydrogen or represents straight-chain or branched alkenyl or alkoxy having in each case up to 8 carbon atoms, or â€ƒrepresents a straight-chain or branched alkyl chain having up to 10 carbon atoms which is optionally interrupted by an oxygen atom and which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of trifluoromethyl, trifluoromethoxy, hydroxyl, halogen, carboxyl, benzyloxycarbonyl, straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms and/or by radicals of the formulae â€”SO3H, â€”(A)aâ€”NR7R8, â€”Oâ€”COâ€”NR7â€²R8â€², â€”S(O)bâ€”R9, â€”P(O)(OR10)(OR11), in whicha and b are identical or different and each represents a number 0 or 1, A represents a radical CO or SO2, R7, R7â€², R8 and R8â€² are identical or different and each represents hydrogen, or â€ƒrepresents cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms, a 5- to 6-membered unsaturated, partially unsaturated or saturated, optionally benzo-fused heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, where the abovementioned ring systems are optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydroxyl, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, halogen, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms or by a group of the formula â€”(SO2)câ€”NR12R13, in which c represents a number 0 or 1, R12 and R13 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 5 carbon atoms, or R7, R7â€², R8 and R8â€² each represent straight-chain or branched alkoxy having up to 6 carbon atoms, or â€ƒrepresents straight-chain or branched alkyl having up to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydroxyl, halogen, aryl having 6 to 10 carbon atoms, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms or by a group of the formula â€”(CO)dâ€”NR14R15, in which R14 and R15 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, and d represents a number 0 or 1, or R7 and R8 and/or R7â€² and R8â€² together with the nitrogen atom form a 5- to 7-membered saturated heterocycle which may optionally contain a further heteroatom from the group consisting of S and O or a radical of the formula â€”NR16, in which R16 represents hydrogen, aryl having 6 to 10 carbon atoms, benzyl, a 5- to 7-membered aromatic or saturated heterocycle having up to 3 heteroatoms from the group consisting of S, N and O which is optionally substituted by methyl, or â€ƒrepresents straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by hydroxyl, R9 represents aryl having 6 to 10 carbon atoms, or â€ƒrepresents straight-chain or branched alkyl having up to 4 carbon atoms, R10 and R11 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, â€ƒand/or the alkyl chain listed above under R3/R4 is optionally substituted by cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or by a 5- to 7-membered partially unsaturated, saturated or unsaturated, optionally benzo-fused heterocycle which may contain up to 4 heteroatoms from the group consisting of S, N and O or a radical of the formula â€”NR17, in which R17 represents hydrogen, hydroxyl, formyl, trifluoromethyl, straight-chain or branched acyl or alkoxy having in each case up to 4 carbon atoms, â€ƒor represents straight-chain or branched alkyl having up to 6 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydroxyl and straight-chain or branched alkoxy having up to 6 carbon atoms, â€ƒand where aryl and the heterocycle are optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of nitro, halogen, â€”SO3H, straight-chain or branched alkyl or alkoxy having in each case up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy and/or by a radical of the formula â€”SO2â€”NR18R19, in which R18 and R19 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, and/or R3 or R4 represents a group of the formula â€”NR20R21, in which R20 and R21 have the meanings of R18 and R19 given above and are identical to or different from them, and/or R3 or R4 represents adamantyl, or represents radicals of the formulae â€ƒor represents cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or represents a 5- to 7-membered partially unsaturated, saturated or unsaturated, optionally benzo-fused heterocycle which may contain up to 4 heteroatoms from the group consisting of S, N and O, or a radical of the formula â€”NR22, in which R22 has the meaning of R16 given above and is identical to or different from it, or â€ƒrepresents carboxyl, formyl or straight-chain or branched acyl having up to 5 carbon atoms, â€ƒand where cycloalkyl, aryl and/or the heterocycle are optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, triazolyl, trifluoromethyl, trifluoromethoxy, carboxyl, straight-chain or branched acyl or alkoxycarbonyl having in each case up to 6 carbon atoms, nitro and/or by groups of the formulae â€”SO3H, â€”OR23, (SO2)eNR24R25, â€”P(O)(OR26)(OR27), in which e represents a number 0 or 1, R23 represents a radical of the formula â€ƒrepresents cycloalkyl having 3 to 7 carbon atoms, or â€ƒrepresents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms which is optionally substituted by cycloalkyl having 3 to 7 carbon atoms, benzyloxy, tetrahydropyranyl, tetrahydrofuranyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, carboxyl, benzyloxycarbonyl or phenyl which for its part may be mono- or polysubstituted by identical or different substituents selected from the group consisting of straight-chain or branched alkoxy having up to 4 carbon atoms, hydroxyl and halogen, â€ƒand/or alkyl which is optionally substituted by radicals of the formulae â€”COâ€”NR28R29 or â€”COâ€”R30, in which R28 and R29 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 8 carbon atoms, or R28 and R29 together with the nitrogen atom form a 5- to 7-membered saturated heterocycle which may optionally contain a further heteroatom from the group consisting of S and O, and R30 represents phenyl or adamantyl, R24 and R25 have the meanings of R18 and R19 given above and are identical to or different from them, R26 and R27 have the meanings of R10 and R11 given above and are identical to or different from them â€ƒand/or cycloalkyl, aryl and/or the heterocycle are optionally substituted by straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by hydroxyl, carboxyl, by a 5- to 7-membered heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, or by groups of the formula â€”SO2â€”R31, P(O)(OR32)(OR33) or â€”NR34R35, in which R31 represents hydrogen or has the meaning of R9 given above and is identical to or different from it, R32 and R33 have the meanings of R10 and R11 given above and are identical to or different from them, R34 and R35 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by hydroxyl or by straight-chain or branched alkoxy having up to 4 carbon atoms, or R34 and R35 together with the nitrogen atom form a 5- to 6-membered saturated heterocycle which may contain a further heteroatom from the group consisting of S and O, or a radical of the formula â€”NR36, in which R36 represents hydrogen, hydroxyl, straight-chain or branched alkoxycarbonyl having up to 7 carbon atoms or straight-chain or branched alkyl having up to 5 carbon atoms which is optionally substituted by hydroxyl, or R3 and R4 together with the nitrogen atom form a 5- to 7-membered unsaturated or saturated or partially unsaturated, optionally benzo-fused heterocycle which may optionally contain up to 3 heteroatoms from the group consisting of S, N and O, or a radical of the formula â€”NR37, in which R37 represents hydrogen, hydroxyl, formyl, trifluoromethyl, straight-chain or branched acyl, alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms, â€ƒor represents straight-chain or branched alkyl having up to 6 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydroxyl, trifluoromethyl, carboxyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or by groups of the formula â€”(D)fâ€”NR38R39, â€”COâ€”(CH2)gâ€”Oâ€”COâ€”R40, â€”COâ€”(CH2)hâ€”OR41 or â€”P(O)(OR42)(OR43), in which g and h are identical or different and each represents a number 1, 2, 3 or 4, and f represents a number 0 or 1, D represents a group of the formula â€”CO or â€”SO2, R38 and R39 are identical or different and each has the meaning of R7 and R8 given above, R40 represents straight-chain or branched alkyl having up to 6 carbon atoms, R41 represents straight-chain or branched alkyl having up to 6 carbon atoms, R42 and R43 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, or R37 represents a radical of the formula â€”(CO)iâ€”E, in which i represents a number 0 or 1, E represents cycloalkyl having 3 to 7 carbon atoms or benzyl, represents aryl having 6 to 10 carbon atoms or a 5- to 6-membered aromatic heterocycle having up to 4 heteroatoms from the group consisting of S, N and O, where the abovementioned ring systems are optionally mono- or polysubstituted by identical or different constituents selected from the group consisting of nitro, halogen, â€”SO3H, straight-chain or branched alkoxy having up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy, or by a radical of the formula â€”SO2â€”NR44R45, in which R44 and R45 have the meaning of R18 and R19 given above and are identical to or different from them, or E represents radicals of the formulae â€ƒand the heterocycle listed under R3 and R4, which is formed together with the nitrogen atom, is optionally mono- or polysubstituted, if appropriate also geminally, by identical or different substituents selected from the group consisting of hydroxyl, formyl, carboxyl, straight-chain or branched acyl or alkoxycarbonyl having in each case up to 6 carbon atoms, nitro and groups of the formulae â€”P(O)(OR46)(OR47), â€ƒin which R46 and R47 have the meanings of R10 and R11 given above and are identical to or different from them, R48 represents hydroxyl or straight-chain or branched alkoxy having up to 4 carbon atoms, j represents a number 0 or 1, and R49 and R50 are identical or different and have the meanings of R14 and R15 given above, â€ƒand/or the heterocycle listed under R3 and R4, which is formed together with the nitrogen atom, is optionally substituted by straight-chain or branched alkyl having up to 6 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydroxyl, halogen, carboxyl, cycloalkyl or cycloalkyloxy having in each case 3 to 8 carbon atoms, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or by a radical of the formula â€”SO3H, â€”NR51R52 or P(O)OR53OR54, in which R51 and R52 are identical or different and each represents hydrogen, phenyl, carboxyl, benzyl or straight-chain or branched alkyl or alkoxy having in each case up to 6 carbon atoms, R53 and R54 are identical or different and have the meanings of R10 and R11 given above, â€ƒand/or the alkyl is optionally substituted by aryl having 6 to 10 carbon atoms which for its part may be mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, hydroxyl, straight-chain or branched alkoxy having up to 6 carbon atoms, or by a group of the formula â€”NR51â€²R52â€², in which R51â€² and R52â€² have the meanings of R51 and R52 given above and are identical to or different from them, â€ƒand/or the heterocycle listed under R3 and R4, which is formed together with the nitrogen atom, is optionally substituted by aryl having 6 to 10 carbon atoms or by a 5- to 7-membered saturated, partially unsaturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, optionally also attached via a nitrogen function, where the ring systems for their part may be substituted by hydroxyl or by straight-chain or branched alkyl or alkoxy having in each case up to 6 carbon atoms, or R3 and R4 together with the nitrogen atom form radicals of the formulae R5 and R6 are identical or different and each represents hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms, hydroxyl or represents straight-chain or branched alkoxy having up to 6 carbon atoms, and their salts, hydrates, N-oxides and structural isomers.