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Claims for Patent: 6,362,178

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Claims for Patent: 6,362,178

Title: 2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors
Abstract:The 2-phenyl-substituted imidazotriazinones having short, unbranched alkyl radicals in the 9-position are prepared from the corresponding 2-phenyl-imidazotriazinones by chlorosulphonation and subsequent reaction with the amines. The compounds inhibit cGMP-metabolizing phosphodiesterases and are suitable for use as active compounds in pharmaceuticals, for the treatment of cardiovascular and cerebrovascular disorders and/or disorders of the urogenital system, in particular for the treatment of erectile dysfunction.
Inventor(s): Niewohner; Ulrich (Wermelskirchen, DE), Es-Sayed; Mazen (Langenfeld, DE), Haning; Helmut (Wuppertal, DE), Schenke; Thomas (Gladbach, DE), Schlemmer; Karl-Heinz (Wuppertal, DE), Keldenich; Jorg (Wuppertal, DE), Bischoff; Erwin (Wuppertal, DE), Perzborn; Elisabeth (Wuppertal, DE), Dembowsky; Klaus (Boston, MA), Serno; Peter (Gladbach, DE), Nowakowski; Marc (Wuppertal, DE)
Assignee: Bayer Aktiengesellschaft (Leverkusen, DE)
Application Number:09/554,162
Patent Claims: 1. A compound of the formula (I) ##STR412##

in which R.sup.1 represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, R.sup.2 represents straight-chain alkyl having up to 4 carbon atoms, R.sup.3 and R.sup.4 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 represents 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 --SO.sub.3 H, --(A).sub.a --NR.sup.7 R.sup.8, --O--CO--NR.sup.7' R.sup.8', --S(O).sub.b --R.sup.9, --P(O)(OR.sup.10)(OR.sup.11), ##STR413##

in which a and b are identical or different and each represents a number 0 or 1, A represents a radical CO or SO.sub.2, R.sup.7, R.sup.7', R.sup.8 and R.sup.8' are identical or different and each represents hydrogen, or represents 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 --(SO.sub.2).sub.c --NR.sup.12 R.sup.13, in which c represents a number 0 or 1, R.sup.12 and R.sup.13 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 5 carbon atoms, or R.sup.7, R.sup.7', R.sup.8 and R.sup.8' each represent straight-chain or branched alkoxy having up to 6 carbon atoms, or represents 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 --(CO).sub.d --NR.sup.14 R.sup.15, in which R.sup.14 and R.sup.15 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 R.sup.7 and R.sup.8 and/or R.sup.7' and R.sup.8' 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 --NR.sup.16, in which R.sup.16 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 represents straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by hydroxyl, R.sup.9 represents aryl having 6 to 10 carbon atoms, or represents straight-chain or branched alkyl having up to 4 carbon atoms, R.sup.10 and R.sup.11 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, and/or the alkyl chain listed above under R.sup.3 /R.sup.4 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 --NR.sup.17, in which R.sup.17 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- 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, and where aryl and the heterocycle are optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of nitro, halogen, --SO.sub.3 H, 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 --SO.sub.2 --NR.sup.18 R.sup.19, in which R.sup.18 and R.sup.19 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, and/or R.sup.3 or R.sup.4 represents a group of the formula --NR.sup.20 R.sup.21, in which R.sup.20 and R.sup.21 have the meanings of R.sup.18 and R.sup.19 given above and are identical to or different from them, and/or R.sup.3 or R.sup.4 represents adamantyl, or represents radicals of the formulae ##STR414## or 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 --NR.sup.22, in which R.sup.22 has the meaning of R.sup.16 given above and is identical to or different from it, 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- 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 --SO.sub.3 H, --OR.sup.23, (SO.sub.2).sub.e NR.sup.24 R.sup.25, --P(O)(OR.sup.26)(OR.sup.27), in which e represents a number 0 or 1, R.sup.23 represents a radical of the formula ##STR415## represents cycloalkyl having 3 to 7 carbon atoms, or represents 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, and/or alkyl which is optionally substituted by radicals of the formulae --CO--NR.sup.28 R.sup.29 or --CO--R.sup.30, in which R.sup.28 and R.sup.29 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 8 carbon atoms, or R.sup.28 and R.sup.29 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 R.sup.30 represents phenyl or adamantyl, R.sup.24 and R.sup.25 have the meanings of R.sup.18 and R.sup.19 given above and are identical to or different from them, R.sup.26 and R.sup.27 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them 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 O, or by groups of the formula --SO.sub.2 --R.sup.31, P(O)(OR.sup.32)(OR.sup.33) or --NR.sup.34 R.sup.35, in which R.sup.31 represents hydrogen or has the meaning of R.sup.9 given above and is identical to or different from it, R.sup.32 and R.sup.33 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them, R.sup.34 and R.sup.35 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 R.sup.34 and R.sup.35 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 --NR.sup.36, in which R.sup.36 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 R.sup.3 and R.sup.4 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 --NR.sup.37, in which R.sup.37 represents hydrogen, hydroxyl, formyl, trifluoromethyl, straight-chain or branched acyl, alkoxy or alkoxycarbonyl 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- 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 --(D).sub.f --NR.sup.38 R.sup.39, --CO--(CH.sub.2).sub.g --O--CO--R.sup.40, --CO--(CH.sub.2).sub.h --OR.sup.41 or --P(O)(OR.sup.42)(OR.sup.43), 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 --CO or --SO.sub.2, R.sup.38 and R.sup.39 are identical or different and each has the meaning of R.sup.7 and R.sup.8 given above, R.sup.40 represents straight-chain or branched alkyl having up to 6 carbon atoms, R.sup.41 represents straight-chain or branched alkyl having up to 6 carbon atoms, R.sup.42 and R.sup.43 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, or R.sup.37 represents a radical of the formula --(CO).sub.i --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, --SO.sub.3 H, straight-chain or branched alkoxy having up to 6 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy, or by a radical of the formula --SO.sub.2 --NR.sup.44 R.sup.45, in which R.sup.44 and R.sup.45 have the meaning of R.sup.18 and R.sup.19 given above and are identical to or different from them, or E represents radicals of the formulae ##STR416## and the heterocycle listed under R.sup.3 and R.sup.4, 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 --P(O)(OR.sup.46)(OR.sup.47), ##STR417## in which R.sup.46 and R.sup.47 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them, R.sup.48 represents hydroxyl or straight-chain or branched alkoxy having up to 4 carbon atoms, j represents a number 0 or 1, and R.sup.49 and R.sup.50 are identical or different and have the meanings of R.sup.14 and R.sup.15 given above, and/or the heterocycle listed under R.sup.3 and R.sup.4, 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 --SO.sub.3 H, --NR.sup.51 R.sup.52 or P(O)OR.sup.53 OR.sup.54, in which R.sup.51 and R.sup.52 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, R.sup.53 and R.sup.54 are identical or different and have the meanings of R.sup.10 and R.sup.11 given above, and/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 --NR.sup.51' R.sup.52', in which R.sup.51' and R.sup.52' have the meanings of R.sup.51 and R.sup.52 given above and are identical to or different from them, and/or the heterocycle listed under R.sup.3 and R.sup.4, 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 R.sup.3 and R.sup.4 together with the nitrogen atom form radicals of the formulae ##STR418## R.sup.5 and R.sup.6 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.

2. A compound of the formula (I) according to claim 1 in which R.sup.1 represents straight-chain or branched alkyl having up to 3 carbon atoms, R.sup.2 represents straight-chain alkyl having up to 3 carbon atoms, R.sup.3 and R.sup.4 are identical or different and each represents hydrogen or represents straight-chain or branched alkenyl or alkoxy having in each case up to 6 carbon atoms, or represents a straight-chain or branched alkyl chain having up to 8 carbon atoms which is optionally interrupted by an oxygen atom and which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, fluorine, chlorine, carboxyl, benzyloxycarbonyl, straight-chain or branched alkoxycarbonyl having up to 5 carbon atoms, and by radicals of the formulae --SO.sub.3 H, --(A).sub.a --NR.sup.7 R.sup.8, --O--CO--NR.sup.7' R.sup.8', --S(O).sub.b --R.sup.9, 13 P(O)(OR.sup.10)(OR.sup.11), ##STR419## in which a and b are identical or different and each represents a number 0 or 1, A represents a radical CO or SO.sub.2, R.sup.7, R.sup.7', R.sup.8 and R.sup.8' are identical or different and each represents hydrogen, or cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, piperidinyl and pyridyl, where the abovementioned ring systems are optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, fluorine, chlorine, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms, or by a group of the formula --(SO.sub.2).sub.c --NR.sup.12 R.sup.13, in which c represents a number 0 or 1, R.sup.12 and R.sup.13 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, or R.sup.7, R.sup.7', R.sup.8 and R.sup.8' each represent straight-chain or branched alkoxy having up to 3 carbon atoms, or represents straight-chain or branched alkyl having up to 7 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydroxyl, fluorine, chlorine, phenyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms, or by a group of the formula --(CO).sub.d --NR.sup.14 R.sup.15, in which R.sup.14 and R.sup.15 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, and d represents a number 0 or 1, or R.sup.7 and R.sup.8 and/or R.sup.7' and R.sup.8' together with the nitrogen atom form a pyrrolidinyl, morpholinyl, piperidinyl or triazolyl ring or radicals of the formulae ##STR420## in which R.sup.16 represents hydrogen, phenyl, benzyl, morpholinyl, pyrrolidinyl, piperidinyl, piperazinyl or N-methylpiperazinyl, or represents straight-chain or branched alkyl having up to 5 carbon atoms which is optionally substituted by hydroxyl, R.sup.9 represents straight-chain or branched alkyl having up to 3 carbon atoms, R.sup.10 and R.sup.11 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, and/or the alkyl chain listed under R.sup.3 /R.sup.4 is optionally substituted by cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, pyridyl, quinolyl, pyrrolidinyl, pyrimidyl, morpholinyl, furyl, piperidinyl, tetrahydrofuranyl or by radicals of the formulae ##STR421## in which R.sup.17 represents hydrogen, hydroxyl, formyl, trifluoromethyl, straight-chain or branched acyl or alkoxy having in each case up to 3 carbon atoms, or represents straight-chain or branched alkyl having up to 4 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl and straight-chain or branched alkoxy having up to 4 carbon atoms, and where phenyl and the heterocycles are optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of nitro, fluorine, chlorine, --SO.sub.3 H, straight-chain or branched alkyl or alkoxy having in each case up to 4 carbon atoms, hydroxyl, and/or by a radical of the formula --SO.sub.2 --NR.sup.18 R.sup.19, in which R.sup.18 and R.sup.19 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, and/or R.sup.3 or R.sup.4 represents a group of the formula --NR.sup.20 R.sup.21, in which R.sup.20 and R.sup.21 have the meanings of R.sup.18 and R.sup.19 given above and are identical to or different from them, and/or R.sup.3 or R.sup.4 represents adamantyl, or represents radicals of the formulae ##STR422## or represents cyclopentyl, cyclohexyl, cycloheptyl, phenyl, morpholinyl, oxazolyl, thiazolyl, quinolyl, isoxazolyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl or represents radicals of the formulae ##STR423## in which R.sup.22 has the meaning of R.sup.16 given above and is identical to or different from it, or represents carboxyl, formyl or straight-chain or branched acyl having up to 3 carbon atoms, and where cycloalkyl, phenyl and/or the heterocycles are optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, triazolyl, trifluoromethyl, trifluoromethoxy, carboxyl, straight-chain or branched acyl or alkoxycarbonyl having in each case up to 5 carbon atoms, nitro and/or by groups of the formulae --SO.sub.3 H, --OR.sup.23, (SO.sub.2).sub.e NR.sup.24 R.sup.25, --P(O)(OR.sup.26)(OR.sup.27), in which e represents a number 0 or 1, R.sup.23 represents a radical of the formula ##STR424## represents cyclopropyl, cyclopentyl, cyclobutyl, cyclohexyl or cycloheptyl, represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms which may optionally be substituted by cyclopropyl, cyclopentyl, cyclohexyl, benzyloxy, tetrahydropyranyl, tetrahydrofuranyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms, 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 3 carbon atoms, hydroxyl, fluorine and chlorine, and/or where alkyl is optionally substituted by radicals of the formulae --CO--NR.sup.28 R.sup.29 or --CO--R.sup.30, in which R.sup.28 and R.sup.29 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 5 carbon atoms, or R.sup.28 and R.sup.29 together with the nitrogen atom form a morpholinyl, pyrrolidinyl or piperidinyl ring, and R.sup.30 represents phenyl or adamantyl, R.sup.24 and R.sup.25 have the meanings of R.sup.18 and R.sup.19 given above and are identical to or different from them, R.sup.26 and R.sup.27 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them and/or cycloalkyl, phenyl and/or the heterocycles are optionally substituted by straight-chain or branched alkyl having up to 4 carbon atoms which is optionally substituted by hydroxyl, carboxyl, pyridyl, pyrimidyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, triazolyl or by groups of the formula --SO.sub.2 --R.sup.31, --P(O)(OR.sup.32)(OR.sup.33) or --NR.sup.34 R.sup.35, in which R.sup.31 has the meaning of R.sup.9 given above and is identical to or different from it, R.sup.32 and R.sup.33 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them, R.sup.34 and R.sup.35 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 5 carbon atoms which is optionally substituted by hydroxyl or straight-chain or branched alkoxy having up to 3 carbon atoms, or R.sup.34 and R.sup.35 together with the nitrogen atom form a morpholinyl, triazolyl or thiomorpholinyl ring or a radical of the formula ##STR425## in which R.sup.36 represents hydrogen, hydroxyl, straight-chain or branched alkoxycarbonyl having up to 5 carbon atoms or straight-chain or branched alkyl having up to 4 carbon atoms which is optionally substituted by hydroxyl, or R.sup.3 and R.sup.4 together with the nitrogen atom form a morpholinyl, thiomorpholinyl, pyrrolidinyl, piperidinyl ring, or a radical of the formula ##STR426## in which R.sup.37 represents hydrogen, hydroxyl, formyl, trifluoromethyl, straight-chain or branched acyl, alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms, or represents straight-chain or branched alkyl having up to 5 carbon atoms which is optionally mono- to trisubstituted 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 4 carbon atoms, or by groups of the formula --(D).sub.f --NR.sup.38 R.sup.39, --CO--(CH.sub.2).sub.g --O--CO--R.sup.40, --CO--(CH.sub.2).sub.h --OR.sup.41 or P(O)(OR.sup.42)(OR.sup.43), in which g and h are identical or different and each represents a number 1, 2 or 3, and f represents a number 0 or 1, D represents a group of the formula --CO or --SO.sub.2, R.sup.38 and R.sup.39 are identical or different and have the meanings of R.sup.7 and R.sup.8 given above, R.sup.40 represents straight-chain or branched alkyl having up to 4 carbon atoms, R.sup.41 represents straight-chain or branched alkyl having up to 4 carbon atoms, R.sup.42 and R.sup.43 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, or R.sup.37 represents a radical of the formula --(CO).sub.i --E, in which i represents a number 0 or 1, E represents cyclopentyl, cyclohexyl, cycloheptyl, benzyl, phenyl, pyridyl, pyrimidyl or furyl, where the abovementioned ring systems are optionally mono- or disubstituted by identical or different substituents selected from the group consisting of nitro, fluorine, chlorine, --SO.sub.3 H, straight-chain or branched alkoxy having up to 4 carbon atoms, hydroxyl, trifluoromethyl, trifluoromethoxy or by a radical of the formula --SO.sub.2 --NR.sup.44 R.sup.45, in which R.sup.44 and R.sup.45 have the meanings of R.sup.18 and R.sup.19 given above and are identical to or different from them, or E represents radicals of the formulae ##STR427## and the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally mono- to trisubstituted, optionally 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 5 carbon atoms, nitro and groups of the formulae --P(O)(OR.sup.46)(OR.sup.47), ##STR428## .dbd.NR.sup.48 or --(CO).sub.j NR.sup.49 R.sup.50 in which R.sup.46 and R.sup.47 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them, R.sup.48 represents hydroxyl or straight-chain or branched alkoxy having up to 3 carbon atoms, j represents a number 0 or 1, and R.sup.49 and R.sup.50 are identical or different and have the meanings of R.sup.14 and R.sup.15 given above, and/or the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally substituted by straight-chain or branched alkyl having up to 5 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydroxyl, fluorine, chlorine, carboxyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 4 carbon atoms, or by a radical of the formula --SO.sub.3 H, --NR.sup.51 R.sup.52 or --P(O)OR.sup.53 R.sup.54, in which R.sup.51 and R.sup.52 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 4 carbon atoms, R.sup.53 and R.sup.54 are identical or different and have the meanings of R.sup.10 and R.sup.11 given above, and/or the alkyl is optionally substituted by phenyl which for its part may be mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, hydroxyl, straight-chain or branched alkoxy having up to 4 carbon atoms, or by a group of the formula --NR.sup.51' R.sup.52', in which R.sup.51' and R.sup.52' have the meanings of R.sup.51 and R.sup.52 given above and are identical to or different from them, and/or the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally substituted by phenyl, pyridyl, piperidinyl, pyrrolidinyl or tetrazolyl, 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 5 carbon atoms, or R.sup.3 and R.sup.4 together with the nitrogen atom form radicals of the formulae ##STR429## R.sup.5 and R.sup.6 are identical or different and each represents hydrogen, hydroxyl or represents straight-chain or branched alkoxy having up to 4 carbon atoms,

and their salts, hydrates, N-oxides and structural isomers.

3. A compound of the formula (I) according to claim 1 in which R.sup.1 represents straight-chain or branched alkyl having up to 3 carbon atoms, R.sup.2 represents straight-chain alkyl having up to 3 carbon atoms, R.sup.3 and R.sup.4 are identical or different and each represents hydrogen or represents straight-chain or branched alkenyl or alkoxy having in each case up to 4 carbon atoms, or represents a straight-chain or branched alkyl chain having up to 6 carbon atoms which is optionally interrupted by an oxygen atom and which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, fluorine, chlorine, carboxyl, straight-chain or branched alkoxycarbonyl having up to 4 carbon atoms, and/or by radicals of the formulae --SO.sub.3 H, --(A).sub.a --NR.sup.7 R.sup.8, --O--CO--NR.sup.7' R.sup.8', --S(O).sub.b --R.sup.9, --P(O)(OR.sup.10)(OR.sup.11), ##STR430## in which a and b are identical or different and each represents a number 0 or 1, A represents a radical CO or SO.sub.2, R.sup.7, R.sup.7', R.sup.8 and R.sup.8' are identical or different and each represents hydrogen, or represents cyclopentyl, cyclohexyl, cycloheptyl, phenyl, piperidinyl and pyridyl, where the abovementioned ring systems are optionally mono- or disubstituted by identical or different substituents selected from the group consisting of hydroxyl, nitro, carboxyl, fluorine, chlorine, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or by a group of the formula --(SO.sub.2).sub.c --NR.sup.12 R.sup.13, in which c represents a number 0 or 1, R.sup.12 and R.sup.13 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, or R.sup.7, R.sup.7', R.sup.8 and R.sup.8' each represent methoxy, or represent straight-chain or branched alkyl having up to 6 carbon atoms which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of hydroxyl, fluorine, chlorine, phenyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or by a group of the formula --(CO).sub.d --NR.sup.14 R.sup.15, in which R.sup.14 and R.sup.15 are identical or different and each represents hydrogen, methyl or ethyl, and d represents a number 0 or 1, or R.sup.7 and R.sup.8 and/or R.sup.7' and R.sup.8' together with the nitrogen atom form a morpholinyl, piperidinyl or triazolyl ring or radicals of the formulae ##STR431## in which R.sup.16 represents hydrogen, phenyl, benzyl, morpholinyl, pyrrolidinyl, piperidinyl, piperazinyl or N-methylpiperazinyl, or represents straight-chain or branched alkyl having up to 3 carbon atoms which is optionally substituted by hydroxyl, R.sup.9 represents methyl, R.sup.10 and R.sup.11 are identical or different and each represents hydrogen, methyl or ethyl, and/or the alkyl chain listed under R.sup.3 /R.sup.4 is optionally substituted by cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, morpholinyl, furyl, tetrahydrofuranyl, or by radicals of the formulae ##STR432## in which R.sup.17 represents hydrogen, hydroxyl, formyl, acetyl or alkoxy having up to 3 carbon atoms, or represents straight-chain or branched alkyl having up to 3 carbon atoms which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of hydroxyl or straight-chain or branched alkoxy having up to 3 carbon atoms, and where phenyl and the heterocycles are optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, --SO.sub.3 H, straight-chain or branched alkyl or alkoxy having in each case up to 3 carbon atoms, hydroxyl, and/or by a radical of the formula --SO.sub.2 --NR.sup.18 R.sup.19, in which R.sup.18 and R.sup.19 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, and/or R.sup.3 or R.sup.4 represents a group of the formula --NR.sup.20 R.sup.21, in which R.sup.20 and R.sup.21 have the meanings of R.sup.18 and R.sup.19 given above and are identical to or different from them, and/or R.sup.3 or R.sup.4 represents adamantyl, or represents radicals of the formulae ##STR433## or represents cyclopentyl, cyclohexyl, cycloheptyl, phenyl, morpholinyl, oxazolyl, thiazolyl, quinolyl, isoxazolyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl, or represents radicals of the formulae ##STR434## in which R.sup.22 has the meaning of R.sup.16 given above and is identical to or different from it, or represents formyl or acetyl, and where cycloalkyl, phenyl and/or the heterocycles are optionally mono- or disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, triazolyl, carboxyl, straight-chain or branched acyl or alkoxycarbonyl having in each case up to 4 carbon atoms, nitro, and/or by groups of the formulae --SO.sub.3 H, --OR.sup.23, (SO.sub.2).sub.e NR.sup.24 R.sup.25, --P(O)(OR.sup.26)(OR.sup.27), in which e represents a number 0 or 1, R.sup.23 represents a radical of the formula ##STR435## represents cyclopropyl, cyclopentyl, cyclobutyl or cyclohexyl, represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms which is optionally substituted by cyclopropyl, cyclohexyl, benzyloxy, tetrahydropyranyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, benzyloxycarbonyl or phenyl which for its part may be mono- or disubstituted by identical or different substituents selected from the group consisting of methoxy, hydroxyl, fluorine or chlorine, and/or where alkyl is optionally substituted by radicals of the formulae --CO--NR.sup.28 R.sup.29 or --CO--R.sup.30, in which R.sup.28 and R.sup.29 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, or R.sup.28 and R.sup.29 together with the nitrogen atom form a morpholinyl, pyrrolidinyl or piperidinyl ring, and R.sup.30 represents phenyl or adamantyl, R.sup.24 and R.sup.25 have the meaning of R.sup.18 and R.sup.19 given above and are identical to or different from them, R.sup.26 and R.sup.27 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them and/or cycloalkyl, phenyl and/or the heterocycles are optionally substituted by straight-chain or branched alkyl having up to 3 carbon atoms, which is optionally substituted by hydroxyl, carboxyl, pyridyl, pyrimidyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, triazolyl or by groups of the formula --SO.sub.2 --R.sup.31, P(O)(OR.sup.32)(OR.sup.33) or --NR.sup.34 R.sup.35, in which R.sup.31 represents methyl, R.sup.32 and R.sup.33 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them, R.sup.34 and R.sup.35 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms which is optionally substituted by hydroxyl or methoxy, or R.sup.34 and R.sup.35 together with the nitrogen atom form a morpholinyl, triazolyl or thiomorpholinyl ring or a radical of the formula ##STR436## in which R.sup.36 represents hydrogen, hydroxyl, straight-chain or branched alkoxycarbonyl having up to 3 carbon atoms or straight-chain or branched alkyl having up to 3 carbon atoms which is optionally substituted by hydroxyl, or R.sup.3 and R.sup.4 together with the nitrogen atom form a morpholinyl, thiomorpholinyl, pyrrolidinyl, piperidinyl ring, or a radical of the formula ##STR437## in which R.sup.37 represents hydrogen, hydroxyl, formyl, straight-chain or branched acyl, alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or represents straight-chain or branched alkyl having up to 4 carbon atoms which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of hydroxyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or by groups of the formula --(D).sub.f --NR.sup.38 R.sup.39, --CO--(CH.sub.2).sub.g --O--CO--R.sup.40, --CO--(CH.sub.2).sub.h --OR.sup.41 or --P(O)(OR.sup.42)(OR.sup.43), in which g and h are identical or different and each represents a number 1 or 2, and f represents a number 0 or 1, D represents a group of the formula --CO or --SO.sub.2, R.sup.38 and R.sup.39 are identical or different and have the meanings of R.sup.7 and R.sup.8 given above, R.sup.40 represents straight-chain or branched alkyl having up to 3 carbon atoms, R.sup.41 represents straight-chain or branched alkyl having up to 3 carbon atoms, R.sup.42 and R.sup.43 are identical or different and each represents hydrogen, methyl or ethyl, or R.sup.37 represents a radical of the formula --(CO).sub.i --E, in which i represents a number 0 or 1, E represents cyclopentyl, benzyl, phenyl, pyridyl, pyrimidyl or furyl, where the abovementioned ring systems are optionally mono- or disubstituted by identical or different substituents selected from the group consisting of nitro, fluorine, chlorine, --SO.sub.3 H, straight-chain or branched alkoxy having up to 3 carbon atoms, hydroxyl, or by a radical of the formula --SO.sub.2 --NR.sup.44 R.sup.45, in which R.sup.44 and R.sup.45 have the meanings of R.sup.18 and R.sup.19 given above and are identical to or different from them, or E represents radicals of the formulae ##STR438## and the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally mono- to trisubstituted, optionally 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 3 carbon atoms, or groups of the formulae --P(O)(OR.sup.46)(OR.sup.47), ##STR439## .dbd.NR.sup.48 or --(CO).sub.j NR.sup.49 R.sup.50 in which R.sup.46 and R.sup.47 have the meanings of R.sup.10 and R.sup.11 given above and are identical to or different from them, R.sup.48 represents hydroxyl or methoxy, j represents a number 0 or 1, and R.sup.49 and R.sup.50 are identical or different and have the meanings of R.sup.14 and R.sup.15 given above, and/or the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally substituted by straight-chain or branched alkyl having up to 4 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, fluorine, chlorine, carboxyl, cyclopropyl, cycloheptyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or by a radical of the formula --SO.sub.3 H, --NR.sup.51 R.sup.52 or P(O)OR.sup.53 OR.sup.54, in which R.sup.51 and R.sup.52 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 3 carbon atoms, R.sup.53 and R.sup.54 are identical or different and have the meanings of R.sup.10 and R.sup.11 given above, and/or the alkyl is optionally substituted by phenyl which for its part may be mono- to disubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, hydroxyl, methoxy, or by a group of the formula --NR.sup.51' R.sup.52', in which R.sup.51' and R.sup.52' have the meanings of R.sup.51 and R.sup.52 given above and are identical to or different from them, and/or the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally substituted by phenyl, pyridyl, piperidinyl, pyrrolidinyl or tetrazolyl, if appropriate 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 3 carbon atoms, or R.sup.3 and R.sup.4 together with the nitrogen atom form radicals of the formulae ##STR440## R.sup.5 and R.sup.6 are identical or different and each represents hydrogen, hydroxyl or represents straight-chain or branched alkoxy having up to 3 carbon atoms,

and their salts, hydrates, N-oxides and structural isomers.

4. A compound of the formula (I) according to claim 1 in which R.sup.1 represents methyl or ethyl, R.sup.2 represents ethyl or propyl, R.sup.3 and R.sup.4 are identical or different and each represents a straight-chain or branched alkyl chain having up to 5 carbon atoms which is optionally substituted up to two times by identical or different substituents selected from the group consisting of hydroxyl and methoxy, or R.sup.3 and R.sup.4 together with the nitrogen atom form a piperidinyl, morpholinyl, thiomorpholinyl ring, or a radical of the formula ##STR441## in which R.sup.37 represents hydrogen, formyl, straight-chain or branched acyl or alkoxycarbonyl having in each case up to 3 carbon atoms, or represents straight-chain or branched alkyl having up to 3 carbon atoms which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of hydroxyl, carboxyl, straight-chain or branched alkoxy or alkoxycarbonyl having in each case up to 3 carbon atoms, or by groups of the formulae --(D).sub.f --NR.sup.38 R.sup.39 or --P(O)(OR.sup.42)(OR.sup.43), in which f represents a number 0 or 1, D represents a group of the formula --CO, R.sup.38 and R.sup.39 are identical or different and each represents hydrogen or methyl, R.sup.42 and R.sup.43 are identical or different and each represents hydrogen, methyl or ethyl, or R.sup.37 represents cyclopentyl, and the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally mono- or disubstituted, optionally 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 3 carbon atoms, or groups of the formulae --P(O)(OR.sup.46)(OR.sup.47) or --(CO).sub.j NR.sup.49 R.sup.50, in which R.sup.46 and R.sup.47 are identical or different and each represents hydrogen, methyl or ethyl, j represents a number 0 or 1, and R.sup.49 and R.sup.50 are identical or different and each represents hydrogen or methyl and/or the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally substituted by straight-chain or branched alkyl having up to 3 carbon atoms which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of hydroxyl, carboxyl, or by a radical of the formula P(O)OR.sup.53 OR.sup.54, in which R.sup.53 and R.sup.54 are identical or different and each represents hydrogen, methyl or ethyl, and/or the heterocycles listed under R.sup.3 and R.sup.4, which are formed together with the nitrogen atom, are optionally substituted by pyrrolidinyl or piperidinyl attached via nitrogen, R.sup.5 represents hydrogen, and R.sup.6 represents ethoxy or propoxy,

and their salts, hydrates, N-oxides and isomeric forms.

5. A compound of the according to claim 1 having the following structures:

6. Process for preparing a compound according to claim 1, characterized in that initially compounds of the formula (II) ##STR454##

in which R.sup.1 and R.sup.2 are each as defined above in claim 1, and L represents straight-chain or branched alkyl having up to 4 carbon atoms,

are converted with compounds of the general formula (III) ##STR455##

in which R.sup.5 and R.sup.6 are each as defined above in claim 1,

in a two-step reaction first in the system consisting of ethanol and second in the system consisting of phosphorus oxytrichloride/dichloroethane into the compounds of the general formula (IV) ##STR456##

in which R.sup.1, R.sup.2, R.sup.5 and R.sup.6 are each as defined above in claim 1,

which are reacted in a further step with chlorosulphonic acid to give the compounds of the formula (V) ##STR457##

in which R.sup.1, R.sup.2, R.sup.5 and R.sup.6 are each as defined above in claim 1,

which are finally reacted with amines of the formula (VI)

in which R.sup.3 and R.sup.4 are each as defined above in claim 1,

in inert solvents.

7. Pharmaceuticals which comprise at least one 2-phenyl-substituted imidazotriazinone according to claim 1 and pharmacologically acceptable formulating agents.

8. A method of treating chronic heart failure or erectile dysfunction, comprising administering to a mammal an effective amount of a compound according to claim 1.
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