7-alkyl- and cycloalkyl-substituted imidazotriazinones

7-Alkyl- and cycloalkyl-substituted imidazotriazinones of the formula (I)

• in which
• R1 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 —SO3H, —(A)a—NR7R8, —O—CO—NR7′R8′, —S(O)b—R9, HN═SO—R9′, —P(O)(OR10)(OR11),
• in which
• a and b are identical or different and represent a number 0 or 1,
• A represents a radical CO or SO2,
• R7, R7′, R8 and R8′ 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 —(SO2)c—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, R7′, R8 and R8′ 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 —(CO)d—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 R7′ and R8′ 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 —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 R9′ 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 —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, —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 —(SO2)e—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 —NR20 R21 or —(O)—E—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 —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
• or 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 —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 —SO3H, —OR26, (SO2)fNR27R28, —P(O)(OR29)(OR30),
• in which
• R26 represents a radical of the formula
• represents 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 —CO—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 —SO2—R31, P(O)(OR32)(OR33) or —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 —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 —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 —(CO)g—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 —P(O)(OR38)(OR39) and —(CO)g)—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 —SO3H, —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 —NR42′R43′,
• in which
• R42′ and R43′ 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
• in which
• R44 represents hydrogen or straight-chain or branched alkyl or alkoxycarbonyl having in each case up to 6 carbon atoms,
• R45 and R45′ 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.