Claims
- 1. A compound corresponding to the structure (I A), (I B) or (II)
- 2. A compound according to claim 1, wherein the compound is present as a physiologically compatible salt.
- 3. A compound according to claim 1, wherein the compound is present as a pure enantiomer or a pure diastereomer.
- 4. A compound according to claim 1, wherein the compound is present as a mixture of enantiomers or a mixture of stereoisomers.
- 5. A compound according to claim 1, wherein
R1 and R2 are independently selected from the group consisting of H, O—R9, S—R10, C1-6-alkyl, aryl′ or —(C1-6-alkyl)-aryl′, wherein aryl′ is aryl1, aryl2, or aryl3, 26 wherein exactly one of the radicals R1 and R2 is H, or wherein one of the radicals R1 and R2 is aryl′ and the other radical of R1 and R2 is H or C1-12-alkyl, and where R29, R30 and R31 are independently selected from the group consisting of H, C1-6-alkyl, F, Cl, Br, I, OH, O—C1-6-alkyl, O-aryl1 and O—CH2-aryl1, R3 and R4 are H, or unsubstituted, singly substituted or multiply substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, aryl′ or —CH2-aryl′, where multiple substitution comprises replacement of multiple hydrogens bonded to one or more atoms by one or more substituents, and wherein at least one of the radicals R3 and R4 is H, or one of the radicals R1 and R2 together with one of the radicals R3 and R4 form W, where W is α′-CH═CH—CH2-β′, —CH═CH—CH2—CH2-β′, or α′-O—(CH2)m-β′ where m=2, 3, 4 or 5, or where W corresponds to 27 where the end of W identified by α′ is joined to the atom identified by α in the compound corresponding to structure (I A), (I B) or (II), the end of W identified by β′ is joined to the atom identified by β in the compound corresponding to structure (I A), (I B) or (II), the other radical of R1 and R2 is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl and the other radical of R3 and R4 is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, or sec.-hexyl; R5 is unsubstituted, singly substituted, or multiply substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, where multiple substitution comprises replacement of multiple hydrogens bonded to one or more atoms by one or more substituents, or R5 is aryl′, —(CH2)k-aryl′ where k=1,2, 3 or 4, heterocyclyl, or C(═O)R11; R6 is H, methyl, ethyl, —CN, fluorine, chlorine, bromine, iodine, —C(═O)R17 or —N═N-aryl1; R7 is H, aryl1, OR18, S(O)qR19 where q=0, 1 or 2, or R7 is unsubstituted, singly substituted, or multiply substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl, where multiple substitution comprises replacement of multiple hydrogens bonded to one or more atoms by one or more substituents, R8 is H or aryl′, or the radicals R7 and R8 together form Y, where Y is γ′-CR21═CR22—CR23═CR24-δ′, where the end of Y identified by γ′ is joined to the atom identified by γ in the compound corresponding to structure (II), and the end of Y identified by δ′ is joined to the atom identified by δ in the compound corresponding to structure (II); R9 is unsubstituted, singly substituted or multiply substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl or is —[(CH2)r—O]s—H where r=1, 2, 3, 4, 5 or 6 and s=1, 2, 3, 4, 5 or 6, where multiple substitution comprises replacement of multiple hydrogens bonded to one or more atoms by one or more substituents; R10 is aryl′; R11 is aryl′ or OR25; R17 is OR26; R18 is H or methyl; R19 is H, aryl1, or unsubstituted, singly substituted or multiply substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl, where multiple substitution comprises replacement of multiple hydrogens bonded to one or more atoms by one or more substituents; R21, R22, R23 and R24 are independently selected from the group consisting of H, fluorine, chlorine, bromine, iodine and OR28; R25 is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl, where R25 is not H when both R1 is aryl and R2 is alkyl; R26 is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl or sec.-hexyl; R28 is H, methyl or ethyl; Heterocyclyl is furan-2-yl, furan-3-yl, thien-2-yl, thien-3-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, where furanyl, thienyl and pyridinyl are unsubstituted, singly substituted or multiply substituted, and where multiple substitution comprises replacement of multiple hydrogens bonded to one or more atoms by one or more substituents; R29, R30 and R31, when occurring within R3, R4, R5, R7, R8, R10, R11, or R19, are independently selected from the group consisting of H, C1-6-alkyl, C3-8-cycloalkyl, (C1-6 alkyl)-C3-8-cycloalkyl, aryl, (C1-6-alkyl)-aryl, heterocyclyl, (C1-6 alkyl)-heterocyclyl, F, Cl, Br, I, —CN, —NC, —OR32, —SR33, —NO, —NO2, NH2, NHR34, NR35R36, —N—OH, —N—OC1-6-alkyl, —NHNH2, —N═N-aryl, —(C═O)R37, —(C═S)R37, or 28 where d=1, 2 or 3, and may be in any arbitrary ring position; R32 and R33 are independently selected from the group consisting of H, —C1-6-alkyl, —C3-8-cycloalkyl, —(C1-6-alkyl)-C3-8-cycloalkyl, -aryl, —(C1-6-alkyl)-aryl, -heterocyclyl, —(C1-6-alkyl)-heterocyclyl, (C═O)R38, —[(CH2)w—O]z—H or —[(CH2)w—O]z—C1-6-alkyl where w 1, 2, 3 or 4 and z=1, 2, 3, 4 or 5; R34 is C1-6-alkyl, —CH2-aryl or —(C═O)O-tert.-butyl; R35 and R36 are C1-6-alkyl or together are —(CH2)g— and form a ring where g=4 or 5; R37 is H, —C1-6-alkyl, —C3-8-cycloalkyl, —(C1-6-alkyl)-C3-8-cycloalkyl, -aryl, —(C1-6-alkyl)-aryl, -heterocyclyl, —(C1-6-alkyl)-heterocyclyl, —OR39, —NH2, —NHR34, NR35R36; R38 is H, —C1-6-alkyl, —C3-8-cycloalkyl, —(C1-6-alkyl)-C3-8-cycloalkyl, -aryl, —(C1-6-alkyl)-aryl; and R39 is H, —C1-6-alkyl, —C3-8-cycloalkyl, —(C1-6-alkyl)-C3-8-cycloalkyl, -aryl, —(C1-6-alkyl)-aryl, -heterocyclyl or —(C1-6-alkyl)-heterocyclyl.
- 6. A compound according to claim 1, wherein
R1 and R2 are independently selected from the group consisting of H, O—R9, S—R10, or unsubstituted, singly substituted, or multiply substituted methyl, ethyl, n-propyl, 2-propyl, n-butyl, tert.-butyl or n-hexyl, aryl′ or —CH2-aryl′, where aryl′ is aryl1, aryl2, or aryl3, 29 where R29, R30 and R31 are independently selected from the group consisting of H, methyl, ethyl, 2-propyl, n-butyl, tert.-butyl, n-hexyl, F, Cl, Br, I, OH, O-methyl, and O-ethyl, wherein exactly one of R1 and R2 is H, or wherein one of the radicals R1 and R2 is aryl′ and the other radical of R1 and R2 is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, tert.-butyl or n-hexyl, R3 and R4 are independently selected from the group consisting of H, methyl or aryl1, wherein the aryl1 substituents R29, R30 and R31 are independent selected from the group consisting of H, methyl and O-methyl, wherein at least one of the radicals R3 and R4 is H, or one of the radicals R1 and R2 together with one of the radicals R3 and R4 form W, where W is α′-CH═CH—CH2-β′, α′-CH═CH—CH2—CH2-β′, α′-O—(CH2)m-β′ where m=2, 3, 4 or 5, or where W corresponds to 30 where the end of W identified by α′ is joined to the atom identified by α in the compound corresponding to structure (I A), (I B) or (II), the end of W identified by β′ is joined to the atom identified by β in the compound corresponding to structure (I A), (I B) or (II), and the other radical of R1 and R2 and the other radical of R3 and R4 is H; R5 is methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, —(CH2)4—OH, cyclopropyl that is unsubstituted or singly substituted by C(═O)OH, C(═O)O-methyl or C(═O)O-ethyl, cyclopentyl, cyclohexyl, aryl1 or —(CH2)k-aryl1 where the aryl1 substituents R29, R30 and R31 are independently selected from the group consisting of H, —OH, —O-methyl, O—C6H5, CH3, CF3 or C(═O)OH and k=1 or 2, or R5 is heterocyclyl or C(═O)R11; R6 is H, —CN, bromine, —C(═O)R17 or —N═N-phenyl; R7 is H, methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl or tert.-butyl, or aryl1 where R29, R30 and R31 are independently selected from the group consisting of H, OH, or S(O)qR19 where q=0 or 2, R8 is H, aryl1 where the aryl1 substituents R29, R30 and R31 are independently selected from the group consisting of H, methyl or chlorine, or aryl3 where R29, R30 and R31 are H, or the radicals R7 and R8 together form Y, where Y is γ′-CR21═CR22—CR23═CR24-δ′, where the end of Y identified by γ′ is joined to the atom identified by γ in the compound corresponding to structure (II), and the end of Y identified by δ′ is joined to the atom identified by δ in the compound corresponding to structure (II); R9 is methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, n-amyl, isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, cyclopropyl, cyclopentyl, cyclohexyl, or —[(CH2)r—O]s—H where r=1, 2 or 3 and s=1 or 2; R10 is aryl1; R11 is aryl1 where R29, R30 and R31 are H or OR25; R17 is OR26; R19 is methyl or aryl1, where one of the aryl1 substituents R29, R30 and R31 is H or —NO2, and the two other aryl1 substituents of R29, R30 and R31 are H; R21 and R23 are H; R22 is H, fluorine or OR26; R24 is H or chlorine; R25 is H, methyl or ethyl, where R25 is not H when R1 is aryl and R2 is alkyl; R26 is H, methyl or ethyl; R28 is methyl or ethyl; and Heterocyclyl is furan-2-yl, furan-3-yl, thien-2-yl, thien-3-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, where furanyl, thienyl and pyridinyl are unsubstituted, singly substituted, or multiply substituted by —NO2, CH3 or C(═O)OH, where multiple substitution comprises replacement of multiple hydrogens bonded to one or more atoms by one or more substituents.
- 7. A compound according to claim 1, wherein
R1 and R2 are independently selected from the group consisting of H, O—CH2—CH2—OH, O-cyclohexyl, S-phenyl, methyl, phenyl, 3-fluorophenyl, 3-bromophenyl, 4-bromophenyl, 4-chlorophenyl, 4-fluorophenyl, 3-methylphenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 2,4-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 2-naphthyl or —CH2-phenyl, R3 and R4 are H, methyl or 4-methoxyphenyl, where at least one of R3 and R4 is H, or one of the radicals R1 and R2 together with one of the radicals R3 and R4 form W, where W is α′-CH═CH—CH2-β′, α′-CH═CH—CH2—CH2-β′, or α′-O—(CH2)m-β′ where m=2, 3, 4 or 5, or where W corresponds to 31 where the end of W identified by α′ is joined to the atom identified by α in the compound corresponding to structure (I A), (I B) or (II), the end of W identified by β′ is joined to the atom identified by β in the compound corresponding to structure (I A), (I B) or (II), and the other radical of R1 and R2 and the other radical of R3 and R4 are H; R5 is n-propyl, n-butyl, tert.-butyl, —(CH2)4—OH, cyclopropyl, cycloprop-2-yl-1-carboxylic acid ethyl ether, cyclohexyl, 4-trifluorophenyl, 4-phenoxyphenyl, 2-hydroxy-3-methoxyphenyl, 4-hydroxy-3-methoxyphenyl, 3-carboxy-2-hydroxyphenyl, —(CH2)2-phenyl, 5-carboxyfuran-2-yl, 5-methylfuran-2-yl, 5-nitrofuran-2-yl, 5-nitrothien-2-yl, pyridin-2-yl, pyridin-3-yl, C(═O)-phenyl, C(═O)OH or C(═O)Oethyl, where R5 is not C(═O)OH when both R1 is aryl and R2 is alkyl; R6 is H, —CN, bromine, —C(═O)OH, —C(═O)Oethyl or —N═N-phenyl; R7 is H, phenyl, OH, —S-methyl, —SO2-(4-nitrophenyl) or tert.-butyl; R8 is 4-chlorophenyl, 4-methylphenyl or 2-naphthyl; or the radicals R7 and R8 together form Y, where Y is γ′-CR21═CR22—CR23═CR24-δ′, where the end of Y identified by γ′ is joined to the atom identified by γ in the compound corresponding to structure (II), and the end of Y identified by δ′ is joined to the atom identified by δ in the compound corresponding to structure (II); and R21 is fluorine, methoxy or ethoxy.
- 8. A compound according to claim 1, wherein the compound is selected from the group consisting of:
3-bromo-5-(5-nitrofuran-2-yl)-7-m-tolyltetrahydropyrazolo[1,5-a]pyrimidine 3-bromo-7-(4-fluorophenyl)-7-methyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine 3-bromo-7-naphthalin-2-yl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine 2-(3-bromo-7-m-tolyltetrahydropyrazolo[1,5-a]-pyrimidin-5-yl)-cyclopropanecarboxylic acid ethyl ester 2-[3-bromo-7-(4-bromophenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylic acid ethyl ester 2-(3-bromo-7-naphthalin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-cyclopropanecarboxylic acid ethyl ester 3-bromo-7-(4-fluorophenyl)-7-methyl-5-(5-methylfuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine 3-bromo-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-bromo-7-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-bromo-7-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid 3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine 3-bromo-7-(4-methoxyphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine 5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-3,5-dicarboxylic acid diethyl ester; 5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-3,5-dicarboxylic acid diethyl ester 2-hydroxy-3-phenylazo-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester; 2-hydroxy-3-phenylazo-5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester 2-tert.-butyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester; 2-tert.-butyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester 3-bromo-2-phenyl-5,5a,6,8a-tetrahydro-3H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester; 3-bromo-2-phenyl-5,5a,6,8a-tetrahydro-4H-1,4,8b-triaza-as-indacene-5-carboxylic acid ethyl ester 7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylic acid diethyl ester 3-cyano-2-methylsulfanyl-7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 2-hydroxy-7-(4-hydroxyphenyl)-6-methyl-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-bromo-7-(4-hydroxyphenyl)-6-methyl-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta-[c]fluorene-3,5-dicarboxylic acid diethyl ester; 5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3,5-dicarboxylic acid diethyl ester 2-hydroxy-3-phenylazo-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-5-carboxylic acid ethyl ester; 2-hydroxy-3-phenylazo-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-5-carboxylic acid ethyl ester 7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylic acid diethyl ester 3-cyano-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-cyano-2-methylsulfanyl-7-(2,3,4-trimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid 7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylic acid-3-ethyl ester 3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-cyano-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3,5-dicarboxylic acid-3-ethyl ester 3-bromo-7-(2,4-dimethylphenyl)-2-phenyltetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylic acid 3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid 3-cyano-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylic acid 3-cyano-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid 7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol 3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-2-phenylazotetrahydropyrazolo[1,5-a]pyrimidine 7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrofuran-2-yl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine 7-(4-methoxyphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(2,4-dimethylphenyl)-5-(2-ethoxycarbonylcyclopropyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 2-[7-(2,4-dimethylphenyl)-2-hydroxy-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylic acid ethyl ester 2-[2-tert.-butyl-7-(2,4-dimethylphenyl)tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylic acid ethyl ester 2-[3-bromo-7-(2,4-dimethylphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylic acid ethyl ester 2-[3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylic acid ethyl ester 5-(2-ethoxycarbonylcyclopropyl)-7-(3-fluorophenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 2-[3-bromo-7-(3-bromophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropanecarboxylic acid ethyl ester 2-[7-(3-bromophenyl)-3-cyano-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylic acid ethyl ester 7-(2,4-dimethylphenyl)-5-(5-nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol 7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 7-(2,4-dimethylphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol 3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine 7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(4-methoxyphenyl)-5-(5-nitrothiophen-2-yl) tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 5-[3-bromo-7-(4-methoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-furan-2-carboxylic acid 5-benzoyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 5-benzoyl-7-(2,4-dimethylphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-benzoyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile 5-benzoyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone 5-benzoyl-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-benzoyl-7-(3,4-dimethoxyphenyl)tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile 5-benzoyl-7-(4-methoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 5-benzoyl-7-(4-methoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-benzoyl-7-(4-methoxyphenyl)tetrahydropyrazolo-[1,5-a]pyrimidine-3-carbonitrile 5-benzoyl-7-(3-fluorophenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [3-bromo-7-(3-fluorophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone [3-bromo-7-(3-bromophenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone 7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 3-bromo-7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine 7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(3,4-dimethoxyphenyl)-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(4-phenoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 3-[3-cyano-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoic acid 3-(3-cyano-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-hydroxybenzoic acid; 3-(3-cyano-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-hydroxybenzoic acid 3-(3-cyano-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoic acid 3-[2-tert.-butyl-7-(4-chlorophenyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoic acid 5-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 5-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-6-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-(4-hydroxy-3-methoxyphenyl)-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carboxylic acid ethyl ester; 5-(4-hydroxy-3-methoxyphenyl)-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta-[c]fluorene-3-carboxylic acid ethyl ester 4-(2-tert.-butyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-methoxyphenol; 4-(2-tert.-butyl-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluoren-5-yl)-2-methoxyphenol 5-(4-hydroxy-3-methoxyphenyl)-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile; 5-(4-hydroxy-3-methoxyphenyl)-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile 5-(4-hydroxy-3-methoxyphenyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 4-(2-tert.-butyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-2-methoxyphenol 4-(3-bromo-2-phenyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)-2-methoxyphenol 5-(2-hydroxy-3-methoxyphenyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 7-(4-chlorophenyl)-5-(2-hydroxy-3-methoxyphenyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 5-(4-hydroxybutyl)-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile; 5-(4-hydroxybutyl)-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile 5-(4-hydroxybutyl)-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-(4-hydroxybutyl)-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(4-chlorophenyl)-5-(4-hydroxybutyl)-7-methyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-butyl-2-methylsulfanyl-5,5a,6,10b-tetrahydro-3H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile; 5-butyl-2-methylsulfanyl-5,5a,6,10b-tetrahydro-4H-1,4,10c-triazacyclopenta[c]fluorene-3-carbonitrile 5-butyl-2-methylsulfanyl-7-phenylsulfanyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-butyl-7-phenylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-butyl-(4-chlorophenyl)-7-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-cyclopropyl-7-(2,4-dimethylphenyl)-3-phenylazotetrahydropyrazolo[1,5-a]pyrimidin-2-ol 2-tert.-butyl-5-cyclopropyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine 5-cyclopropyl-7-(2,4-dimethylphenyl)-2-methyl-sulfanyltetrahydro-pyrazolo[1,5-a]pyrimidine-3-carbonitrile 2-tert.-butyl-5-cyclopropyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine 3-bromo-5-cyclopropyl-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine 5-cyclopropyl-7-(4-methoxyphenol)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 5-cyclopropyl-3,5,5a,6,7,11b-hexahydro-1,4,11c-triazacyclopenta[c]phenanthrene-3-carbonitrile 7-(2,4-dimethylphenyl)-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 7-(2,4-dimethylphenyl)-3-phenylazo-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol 3-bromo-7-(2,4-dimethylphenyl)-2-phenyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine 7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-phenethyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(3,4-dimethoxyphenyl)-5-phenethyl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-cyclopropyl-7-(2-hydroxyethoxy)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 2-(2-tert.-butyl-5-cyclopropyltetrahydropyrazolo-[1,5-a]pyrimidin-7-yloxy)-ethanol 5-cyclopropyl-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylic acid ethyl ester; 5-cyclopropyl-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylic acid ethyl ester 5-cyclopropyl-3-phenylazo-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacen-2-ol; 5-cyclopropyl-3-phenylazo-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacen-2-ol 7-cyclohexyloxy-5-cyclopropyltetrahydropyrazolo-[1,5-a]pyrimidin-3-carboxylic acid ethyl ester 7-cyclohexyloxy-5-cyclopropyl-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidin-3-carbonitrile 7-(4-chlorophenyl)-5-cyclohexyltetrahydropyrazolo-[1,5-a]pyrimidin-3-carbonitrile 5-cyclohexyl-7-(2-hydroxyethoxy)-tetrahydropyrazolo-[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 5-cyclohexyl-3,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylic acid ethyl ester; 5-cyclohexyl-4,5,5a,6,7,8a-hexahydro-8-oxa-1,4,8b-triaza-as-indacene-3-carboxylic acid ethyl ester 5-cyclohexyl-7-cyclohexyloxytetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 7-(2,4-dimethylphenyl)-3-phenylazo-5-propyltetrahydropyrazolo[1,5-a]pyrimidin-2-ol 7-(2,4-dimethylphenyl)-2-methylsulfanyl-5-propyltetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 5-tert.-butyl-7-(2,4-dimethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 2,5-di-tert.-butyl-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine 3-bromo-5-tert.-butyl-7-(3,4-dimethoxyphenyl)-2-phenyltetrahydropyrazolo[1,5-a]pyrimidine 2-[3-cyano-6,7-bis-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-cyclopropanecarboxylic acid ethyl ester 3-cyano-6,7-bis-(4-methoxyphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid 4-[3-bromo-6-methyl-2-phenyl-5-(4-trifluoromethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl]-phenol 7-(4-hydroxyphenyl)-6-methyl-2-methylsulfanyl-5-(4-trifluoro-methylphenyl)-tetrahydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 7-(4-hydroxyphenyl)-6-methyl-5-(4-trifluoromethylphenyl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 2-(4-nitrophenylsulfonyl)-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]-pyrimidine 3-(4-chlorophenyl)-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine 5-phenylsulfanyl-7-pyridin-2-yl-3-p-tolyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine 7-methoxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene 7-ethoxy-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene 7-fluoro-4-phenylsulfanyl-2-pyridin-2-yl-3,4-dihydro-2H-9-thia-1,4a-diazafluorene 3-naphthalin-2-yl-5-phenylsulfanyl-7-pyridin-2-yl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine 7-phenyl-3-phenylazo-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol 7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 3-phenylazo-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-2-ol 3-bromo-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine 7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-tetrahydropyrazolo[1,5-a]pyrimidine 3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrofuran-2-yl)-2-phenyl-tetrahydropyrazolo[1,5-a]pyrimidine 3-cyano-7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-cyano-7-(3,4-dimethoxyphenyl)-tetrahydropyrazolo-[1,5-a]pyrimidine-5-carboxylic acid ethyl ester 3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine 7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 7-(3,4-dimethoxyphenyl)-2-methylsulfanyl-5-(5-nitrofuran-2-yl)-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile, and 7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester.
- 9. A process for the preparation of compounds corresponding to structure (I A) or (I B) as well as their pharmaceutically acceptable salts
- 10. A process according to claim 9, wherein the reaction of the heterocyclylamine corresponding to structure (III A) or (III B) with the aldehyde corresponding to structure (IV) and with the olefin corresponding to structure (V) is carried out in a one-pot process.
- 11. A process according to claim 9, wherein the acid is trifluoroacetic acid.
- 12. A process according to of claim 9, wherein the reaction is carried out in an organic solvent at a temperature of 0° to 100° C. and at a reaction time of 0.25 to 12 hours.
- 13. A process according to claim 9, wherein the reaction is carried out at a temperature of 15 to 40° C.
- 14. A process for the preparation of compounds corresponding to structure (II) or pharmaceutically acceptable salts thereof
- 15. A process according to claim 14, wherein the reaction of the heterocyclylamine corresponding to structure (VI) with the aldehyde corresponding to structure (IV) and with the olefin corresponding to structure (V) is carried out in a one-pot process.
- 16. A process according to claim 14, wherein the acid is trifluoroacetic acid.
- 17. A process according to claim 14, wherein the reaction is carried out in an organic solvent at a temperature of 0° to 100° C. and at a reaction time of 0.25 to 12 hours.
- 18. A process according claim 14, wherein the reaction is carried out at a temperature of 15° to 40° C.
- 19. Substance library containing at least one compound corresponding to structure (I A), (I B) or (II)
- 20. A medicament comprising at least one compound corresponding to structure (I A), (I B) or (II)
- 21. A medicament according to claim 20, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a physiologically compatible salt.
- 22. A medicament according to claim 20, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a pure enantiomer or a pure diastereomer.
- 23. A medicament according to claim 20, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a mixture of enantiomers or a mixture of stereoisomers.
- 24. A method for treating pain comprising administering a pharmaceutically effective amount of a compound corresponding to structure (I A), (I B) or (II)
- 25. A method according to claim 24, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a physiologically compatible salt.
- 26. A method according to claim 24, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a pure enantiomer or a pure diastereomer.
- 27. A method according to claim 24, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a mixture of enantiomers or a mixture of stereoisomers.
- 28. A method for treatment or prophylaxis of epilepsy, schizophrenia, neurodegenerative conditions, Alzheimer's disease, Huntington's disease and Parkinson's disease, cerebral ischaemias, infarcts, psychoses due to raised amino acid levels, cerebral oedemas, insufficiency states of the central nervous system, hypoxias, anoxias, AIDS dementia, encephalomyelitis, Tourette's syndrome, perinatal asphyxia, or tinnitus comprising administering a pharmaceutically effective amount of a compound corresponding to structure (I A), (I B) or (II),
- 29. A method according to claim 28, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a physiologically compatible salt.
- 30. A method according to claim 28, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a pure enantiomer or a pure diastereomer.
- 31. A method according to claim 28, wherein the compound corresponding to structure (I A), (I B) or (II) is present as a mixture of enantiomers or a mixture of stereoisomers.
- 32. A method of ligand-binding a nucleoside transport protein, adenosine kinase, adenosine deaminase, or A1, A2, or A3 receptors comprising providing a compound corresponding to formula (I A) or (I B)
- 33. A method according to claim 32, wherein the compound corresponding to structure (I A) or (I B) is present as a physiologically compatible salt.
- 34. A method according to claim 32, wherein the compound corresponding to structure (I A) or (I B) is present as a pure enantiomer or a pure diastereomer.
- 35. A method according to claim 32, wherein the compound corresponding to structure (I A) or (I B) is present as a mixture of enantiomers or a mixture of stereoisomers.
- 36. A method for preventing or treating a medical condition or illness affected by modulating nucleoside transport proteins, adenosine kinase, adenosine deaminase, or A1, A2, or A3 receptors comprising administering a pharmaceutically effective amount of a compound corresponding to formula (I A) or (I B)
- 37. A method according to claim 36, wherein the compound corresponding to structure (I A) or (I B) is present as a physiologically compatible salt.
- 38. A method according to claim 36, wherein the compound corresponding to structure (I A) or (I B) is present as a pure enantiomer or a pure diastereomer.
- 39. A method according to claim 36, wherein the compound corresponding to structure (I A) or (I B) is present as a mixture of enantiomers or a mixture of stereoisomers.
- 40. A method for preventing or treating pain, neuropathic pain, respiratory pathway conditions, cancer, cardiac arrhythmias, ischaemias, epilepsy, Huntington's disease, malfunctions and diseases of the immune system, inflammatory conditions and diseases, neonatal hypoxia, neurodegenerative conditions, Parkinson's disease, kidney failure, schizophrenia, sleep disturbances, strokes, thromboses, urinary incontinence, diabetes, psoriasis, septic shock, cerebral trauma, glaucoma or congestive insufficiency comprising administering a pharmacuetically effective amount of a medicament according to claim 20.
- 41. The method of claim 36, wherein
R1 and R2 are independently selected from the group consisting of H, O—CH2—CH2—OH, O-cyclohexyl, S-phenyl, methyl, phenyl, 3-fluorophenyl, 3-bromophenyl, 4-bromophenyl, 4-chlorophenyl, 4-fluorophenyl, 3-methylphenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 2,4-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 2-naphthyl and —CH2-phenyl, R3 and R4 are H, methyl or 4-methoxyphenyl, where at least one of the radicals R3 and R4 is H, or one of the radicals R1 and R2 together with one of the radicals R3 and R4 form W, where W is α′-CH═CH—CH2-β′, α′-CH═CH—CH2—CH2-β′, or α′-O—(CH2)m-β′ where m=2, 3, 4 or 5, or where W corresponds to 51 where the end of W identified by α′ is joined to the atom identified by α in the compound corresponding to structure (I A) or (I B), the end of W identified by β′ is joined to the atom identified by β in the compound corresponding to structure (I A) or (I B), and the other radical of R1 and R2 and the other radical R3 and R4 are H; R5 is n-propyl, n-butyl, tert.-butyl, —(CH2)4—OH, cyclopropyl, cycloprop-2-yl-1-carboxylic acid ethyl ether, cyclohexyl, 4-trifluorophenyl, 4-phenoxyphenyl, 2-hydroxy-3-methoxyphenyl, 4-hydroxy-3-methoxyphenyl, 3-carboxy-2-hydroxyphenyl, —(CH2)2-phenyl, 5-carboxyfuran-2-yl, 5-methylfuran-2-yl, 5-nitrofuran-2-yl, 5-nitrothien-2-yl, pyridin-2-yl, pyridin-3-yl, C(═O)-phenyl, C(═O)OH or C(═O)Oethyl, where R5 is not C(═O)OH when both R1 is aryl and R2 is alkyl; R6 is H, —CN, bromine, —C(═O)OH, —C(═O)Oethyl or —N═N-phenyl; and R7 is H, phenyl, OH, —S-methyl, —SO2-(4-nitrophenyl) or tert.-butyl.
- 42. A pharmaceutical composition comprising at least one compound corresponding to structure (I A), (I B) or (II)
Priority Claims (2)
Number |
Date |
Country |
Kind |
101 12 197.0 |
Mar 2001 |
DE |
|
101 53 344.6 |
Oct 2001 |
DE |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of International Patent Application No. PCT/EP02/02722, filed Mar. 13, 2002, designating the United States of America, and published in German as WO 02/072585, the entire disclosure of which is incorporated herein by reference. Priority is claimed based on Federal Republic of Germany patent application no. DE 101 12 197.0, filed Mar. 14, 2001, and based on Federal Republic of Germany patent application no. DE 101 53 344.6, filed Oct. 29, 2001.
Continuations (1)
|
Number |
Date |
Country |
Parent |
PCT/EP02/02722 |
Mar 2002 |
US |
Child |
10660794 |
Sep 2003 |
US |