Patent ID: 6476029
Filing Date: 2002-11-05
Classification: A61P,C07D,C07F

Abstract:
7-Alkyl- and cycloalkyl-substituted imidazotriazinones of the formula (I) in whichR1 represents straight-chain or branched alkyl having up to 4 carbon atoms, R2 represent straight-chain alkyl having at least 5 carbon atoms or branched alkyl having at least 3 carbon atoms, or represents cycloalkyl having 3 to 10 carbon atoms, R3 and R4 are identical or different and represent hydrogen, or represent straight-chain or branched alkenyl having up to 8 carbon atoms, or represent 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- to trisubstituted by identical or different substituents from the group consisting of trifluoromethyl, trifluoromethoxy, hydroxyl, halogen carboxyl, benzyloxycarbonyl, straight-chain or branched alkoxy, alkoxycarbonyl and alkylthio having each case 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, HN&boxH;SOâ€”R9â€², â€”P(O)(OR10)(OR11), â€ƒin which a and b are identical or different and represent a number 0 or 1, A represents a radical CO or SO2, R7, R7â€², R8 and R8â€² are identical or different and represent hydrogen, or represent 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/or O, where the ring systems listed above are optionally mono- to trisubstituted by identical or different substituents from the group consisting of hydroxyl, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, halogen, straight-chain or branched alkoxy and 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 represent hydrogen or straight-chain or branched alkyl having up to 5 carbon atoms, or R7, R7â€², R8 and R8â€² represent straight-chain or branched alkoxy having up to 6 carbon atoms, or represent straight-chain or branched alkyl having up to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of hydroxyl, halogen, aryl having from 6 to 10 carbon atoms, straight-chain or branched alkoxy and 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 represent 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, or straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by hydroxyl, R9 and R9â€² are identical or different and represent aryl having 6 to 10 carbon atoms or benzyl, or represent straight-chain or branched alkyl having up to 4 carbon atoms, R10 and R11 are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, and/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 ring heteroatoms from the group consisting of S, N; O or a radical of the formula â€”NR17, where the alkyl chain may optionally also be attached via a ring nitrogen atom, in which R17 represents hydrogen, hydroxyl, formyl, trifluoromethyl, straight-chain or branched acyl or alkoxy having in each case up to 4 carbon atoms, or represents straight-chain or branched alkyl having up to 6 carbon atoms which is optionally mono- to polysubstituted by identical or different substituents from the group consisting of hydroxyl and straight-chain or branched alkoxy having up to 6 carbon atoms, and where aryl and the heterocycle are optionally mono- to trisubstituted by identical or different substituents from the group consisting of nitro, halogen, â€”SO3H, straight-chain or branched monohydroxy-substituted alkyl, alkylthio or alkoxy having in each case up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy and/or by a radical of the formula â€”(SO2)eâ€”R18R19, in which e represents a number 0 or 1, R18 and R19 are identical or different and represent hydrogen, phenyl, benzyl or straight-chain or branched alkyl or acyl having in each case up to 6 carbon atoms, and/or R3 or R4 represent radicals of the formulae â€”NR20 R21 or â€”(O)â€”Eâ€”NR22R23, in which R20 and R21 have the meaning of R18 and R19 given above and are identical to or different from this meaning, or together with the nitrogen atom form a 5- or 6-membered saturated heterocycle having a further ring heterocycle from the group consisting of S and O or a radical â€”NR24, in which R24 has the meaning of R16 given above and is identical to or different from this meaning, E is a straight-chain alkylene group having up to 5 carbon atoms, R22 and R23 have the meaning of R18 and R19 given above and are identical to or different from this meaning, and/or R3 or R4 represent radicals of the formulae â€ƒor represent cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or represent a 5- to 7-membered partially unsaturated, saturated and unsaturated, optionally benzo-fused heterocycle which may contain up to 4 heteroatoms from the group consisting of S, N; O or a radical of the formula â€”NR25 which may optionally also be attached via a ring nitrogen atom, in which R25 has the meaning of R16 given above and is identical to or different from this meaning, or represents carboxyl, formyl or straight-chain or branched acyl having up to 5 carbon atoms, and where cycloalkyl, aryl and/or the heterocycle are optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, 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€”OR26, (SO2)fNR27R28, â€”P(O)(OR29)(OR30), in which R26 represents a radical of the formula â€ƒrepresents cycloalkyl having 3 to 7 carbon atoms, or hydrogen or straight-chain or branched alkyl having up to 5 carbon atoms which is optionally substituted by cycloalkyl having 3 to 7 carbon atoms, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, hydroxyl, carboxyl or phenyl, which for its part may be mono- to trisubstituted by identical or different substituents from the group consisting of straight-chain or branched alkoxy having up to 4 carbon atoms, hydroxyl and halogen, f is a number 0 or 1, R27 and R28 have the meaning of R18 and R19 given above and are identical to or different from this meaning or represent a radical of the formula â€”COâ€”NH2, R29 and R30 have the meaning of R10 and R11 given above and are identical to or different from this meaning, and/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/or O or by groups of the formulae â€”SO2â€”R31, P(O)(OR32)(OR33) or â€”NR34R35, in which R31 is hydrogen or has the meaning of R9 given above and is identical to or different from this meaning, R32 and R33 have the meaning of R10 and R11 given above and are identical to or different from this meaning, R34 and R35 are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by hydroxyl or 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 has the meaning of R16 given above and is identical to or different from this meaning, 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, 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, or represents cycloalkyl having 3 to 8 carbon atoms, or represents straight-chain or branched alkyl having up to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of hydroxyl, trifluoromethyl, pyridyl, carboxyl, straight-chain or branched alkoxy and alkoxycarbonyl having in each case up to 6 carbon atoms, or R37 represents a radical of the formula â€”(CO)gâ€”G, in which g represents a number 0 or 1, G 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/or O, where the ring systems listed above are optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, straight-chain or branched alkoxy, alkyl or alkylthio having in each case up to 6 carbon atoms, hydroxyl and trifluoromethyl, and the heterocycle mentioned under R3 and R4, formed via the nitrogen, is optionally mono- to trisubstituted, optionally also geminally, by identical or different substituents from the group consisting of hydroxyl, formyl, carboxyl, straight-chain or branched acyl and alkoxycarbonyl having in each case up to 6 carbon atoms and groups of the formulae â€”P(O)(OR38)(OR39) and â€”(CO)g)â€”NR40R41, in which R38 and R39 have the meaning of R10 and R11 given above and are identical to or different from this meaning, g represents a number 0 or 1, and R40 and R41 are identical or different and have the meaning of R18 and R19 given above, and/or the heterocycle mentioned under R3 and R4, formed via the nitrogen, is optionally substituted by straight-chain or branched alkyl having up to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents 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 and alkoxycarbonyl having in each case up to 6 carbon atoms or by a radical of the formula â€”SO3H, â€”NR42R43 or P(O)OR44OR45, in which R42 and R43 are identical or different and represent hydrogen, phenyl, carboxyl, benzyl or straight-chain or branched alkyl or alkoxy having in each case up to 6 carbon atoms, R44 and R45 are identical or different and have the meaning of R10 and R11 given above, and/or the alkyl is optionally substituted by benzyloxy or aryl having 6 to 10 carbon atoms, which for its part may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, hydroxyl, straight-chain or branched alkoxy or alkylthio having in each case up to 6 carbon atoms, or by a group of the formula â€”NR42â€²R43â€², in which R42â€² and R43â€² have the meaning of R42 and R43 given above and are identical to or different from this meaning, and/or the heterocycle mentioned under R3 and R4, formed via a 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 ring heteroatoms from the group consisting of S, N and/or O, optionally also attached via an N function, where the ring systems for their part may be substituted by halogen, hydroxyl or by straight-chain or branched alkyl, alkylthio 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 â€ƒin which R44 represents hydrogen or straight-chain or branched alkyl or alkoxycarbonyl having in each case up to 6 carbon atoms, R45 and R45â€² are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, R46 represents hydroxyl or straight-chain or branched alkoxy having up to 6 carbon atoms, R5 and R6 are identical or different and represent hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms, hydroxy or represents straight-chain or branched alkoxy having up to 6 carbon atoms, or their salts or stereoisomeric forms.