8,8A-dihydroindeno[1,2-D] thiazole derivatives which are substituted in the 8A-position; processes for their preparation and their use as medicaments

A compound of formula I,

• 8
• in which
• R1, R1′ are independently selected from H, F, Cl, Br, I, CF3, NO2, CN, COOH, COO(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, O—(C1-C6)-alkyl,
• wherein one or more of the hydrogens of the alkyl radicals may be replaced by fluorine, or one hydrogen may be replaced by OH, OC(O)CH3, OC(O)H, O—CH2—Ph, NH2, NH—CO—CH3 or N(COOCH2Ph)2;
• SO2—NH2, SO2NH(C1-C6)-alkyl, SO2N[(C1-C6)-alkyl]2, S—(C1-C6)-alkyl, S—(CH2)n-phenyl, SO—(C1-C6)-alkyl, SO—(CH2)n-phenyl, SO2—(C1-C6)-alkyl, SO2—(CH2)n-phenyl,
• wherein n is 0-6 and the phenyl radical may be optionally substituted up to two times by F, Cl, Br, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2;
• NH2, NH—(C1-C6)-alkyl, N[(C1-C6)-alkyl]2, NH(C1-C7)-acyl, phenyl, biphenylyl, O—(CH2)n-phenyl, wherein n is 0-6, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl, 2- or 3-thienyl,
• wherein any of the phenyl, biphenylyl, naphthyl, pyridyl, furanyl or thienyl rings may be optionally substituted one to 3 times by F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N[(C1-C6)-alkyl]2, SO2—CH3, COOH, COO—(C1-C6)-alkyl or CONH2;
• 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted in the 1-, 2- or 3-position by methyl or benzyl;
• or
• tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1- or 2-position by methyl or benzyl;
• R2 is H, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (CH2)n-phenyl, (CH2)n-thienyl, (CH2)n-pyridyl, (CH2)n-furyl, C(O)—(C1-C6)-alkyl, C(O)—(C3-C6)-cycloalkyl, C(O)—(CH2)n-phenyl, C(O)—(CH2)n-thienyl, C(O)—(CH2)n-pyridyl or C(O)—(CH2)n-furyl,
• wherein n is 0-5 and in which any of phenyl, thienyl, pyridyl or furyl may be optionally substituted up to two times by Cl, F, CN, CF3, (C1-C3)-alkyl, OH or O—(C1-C6)-alkyl;
• R3 is Cl, Br, CH2—COO(C1-C6)-alkyl, CH2—COOH or CH2—CONH2;
• R4 is (C1-C8)-alkyl, (C3-C7)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C4-C7)-cycloalkenyl,
• wherein one or more of the hydrogens of the alkyl radicals may be replaced by fluorine or one hydrogen may be replaced by OH, OC(O)CH3, OC(O)H, O—CH2—Ph or O—(C1-C4)-alkyl;
• (CH2)n-pyrrolidin-1-yl, (CH2)n-piperidin-1-yl, (CH2)n-morpholin-4-yl, (CH2)n-piperazin-1-yl, (CH2)n—N-4-methylpiperazin-1-yl, (CH2)n—N-4-benzylpiperazin-1-yl, (CH2)n-phthalimidoyl, where n is 1-6;
• (CH2)n-aryl, (CH2)n-heteroaryl,
• wherein n is 0-6 and aryl is phenyl, biphenylyl, or 1- or 2-naphthyl and heteroaryl is 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 2-, 4- or 5-thiazolyl, 2-, 4- or 5-oxazolyl, 1-pyrazolyl, 3- or 5-isoxazolyl, 2- or 3-pyrrolyl, 2- or 3-pyridazinyl, 2-, 4- or 5-pyrimidinyl, 2-pyrazinyl, 2-(1,3,5-triazinyl), 2- or 5-benzimidazolyl, 2-benzothiazolyl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, tetrazol-5-yl, indol-3-yl, indol-5-yl or N-methylimidazol-2-, -4- or -5-yl, and the aryl radical or the heteroaryl radical may be substituted up to two times by F, Cl, Br, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, S—(C1-C6)-alkyl, SO—(C1-C6)-alkyl, (CH2)n—SO2—(C1-C6)-alkyl, (CH2)n—SO2—NH2, (CH2)n—SO2—N(═CH—N(CH3)2), wherein n is 0-6;
• (C1-C6)-alkyl, (C3-C6)-cycloalkyl, COOH, COO(C1-C6)-alkyl, COO(C3-C6)-cycloalkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, CONH(C3-C6)-cycloalkyl, NH2, NH—CO—(C1-C6)-alkyl, NH—CO-phenyl, NH—SO2-(C1-C6)-alkyl or NH—SO2-phenyl,
• wherein the phenyl ring may be substituted up to two times by F, Cl, CN, OH, (C1-C6)-alkyl, O—(C1-C6)-alkyl, CF3, COOH, COO(C1-C6)-alkyl or CONH2;
• pyrrolidin-1-yl, morpholin-1-yl, piperidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, (CH2)n-phenyl, O—(CH2)n-phenyl, S—(CH2)n-phenyl, SO2—(CH2)n-phenyl, where n is 0-3, or (CH2)n—A—R8, where n is 1-6;
• A is O, NH, N—(C1-C6)-alkyl, NCHO, N(CO—CH3), S, SO or SO2;
• R8 is (C1-C8)-alkyl, (C3-C8)-cycloalkyl,
• wherein one or more of the hydrogens of the alkyl radicals may be replaced by fluorine, or one hydrogen may be replaced by OH, OC(O)CH3, OC(O)H, O—CH2—Ph or O—(C1-C4)-alkyl;
• (CH2)m-aryl or (CH2)m-heteroaryl,
• wherein m is 0-6 and aryl is phenyl and heteroaryl is thienyl or pyridyl and the aryl or heteroaryl moiety may be substituted up to two times by F, Cl, Br, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, S—(C1-C6)-alkyl, SO—(C1-C6)-alkyl, (CH2)n—SO2—(C1-C6)-alkyl, (CH2)n—SO2—NH2, (CH2)n—SO2—N(═CH—N(CH3)2), (CH2)n—SO2—NH(C1-C8)-alkyl, (CH2)n—SO2—N[(C1-C8)-alkyl]2, (CH2)n—SO2—NH(C3-C8)-cycloalkyl, (CH2)n—SO2—N[(C3-C8)-cycloalkyl]2, where n is 0-6;
• (C1-C6)-alkyl, (C3-C6)-cycloalkyl, COOH, COO(C1-C6)-alkyl, COO(C3-C6)-cycloalkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, CONH(C3-C6)-cycloalkyl, NH2, NH(C1-C6)-alkyl, N[(C1-C6)-alkyl]2, NH—CO—(C1-C6)-alkyl, NH—CO-phenyl, NH—SO2-phenyl,
• where the phenyl ring may be substituted up to two times by F, Cl, CN, OH, (C1-C6)-alkyl, O—(C1-C6)-alkyl, CF3, COOH, COO(C1-C6)-alkyl or CONH2,
• NH—SO2—(C1-C8)-alkyl, N(C1-C6)-alkyl-SO2—(C1-C8)-alkyl, pyrrolidin-1-yl, morpholin-1-yl, piperidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, (CH2)p-phenyl, O—(CH2)p-phenyl, S—(CH2)p-phenyl or SO2—(CH2)p-phenyl, wherein p is 0-3;
• and their physiologically acceptable salts and physiologically functional derivatives.