Patent NZ-520926-A (NZ)
Title: 8,8a-dihydro-indeno[1,2-d]thiazole derivatives, substituted in position 8a, a method for their production and their use as medicaments, e.g. anorectic agents
Inventor: JAEHNE GERHARD
IPC: C07D277/60
Filed: 2001-02-12
Abstract: Compounds of formula (I) are described wherein: R1, R1' are independently selected from the group consisting of H, F, Cl, Br, I, CF3, NO2, CN, COOH, COO(C1-6)-alkyl, CONH2, CONH(C1-6)-alkyl, CON((C1-6)-alkyl)2, (C1-6)-alkyl, (C2-6)-alkenyl, (C2-6)-alkynyl, O-(C1-6)-alkyl, where in the alkyls radicals one or more hydrogens 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(C1-6)-alkyl, SO2N((C1-6)-alkyl)2, S-(C1-6)-alkyl, S-(CH2)n-phenyl, SO-(C1-6)-alkyl, SO-(CH2)n-phenyl, SO2-(C1-6)-alkyl, SO2-(CH2)n-phenyl, wherein n can be 0-6, wherein the phenyl radical may be substituted up to two times; NH2, NH-(C1-6)-alkyl, N((C1-6)-alkyl)2, NH(C1-C7)-acyl, phenyl, biphenylyl, O-(CH2)n-phenyl, wherein n can be 0-6 , 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, wherein any of rings may be optionally substituted one to 3 times; 1,2,3-triazol-5-yl, tetrazol-5-yl, wherein the rings can be substituted by methyl or benzyl; R2 is H, (C1-6)-alkyl, (C3-6)-cycloalkyl, (CH2)n-phenyl, (CH2)n-thienyl, (CH2)n-pyridyl, (CH2)n-furyl, C(O)-(C1-6)-alkyl, C(O)-(C3-6)-cycloalkyl, C(O)-(CH2)n-phenyl, C(O)-(CH2)n-thienyl, C(O)-(CH2)n-pyridyl or C(O)-(CH2)n-furyl, wherein n can be 0-5, wherein any of phenyl, thienyl, pyridyl or furyl may be optionally substituted up to two times; R3 is Cl, Br, CH2-COO(C1-6)-alkyl, CH2-COOH or CH2-CONH2; R4 is (C1-8)-alkyl, (C3-7)cycloalkyl, (C2-6)-alkenyl, (C2-6)-alkynyl, (C4-7)-cycloalkenyl, where in the alkyl radicals one or more or all of the hydrogens can be replaced by fluorine or one hydrogen may be replaced by OH, OC(O)CH3, OC(O)H, O-CH2-Ph or O-(C1-4)-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, wherein n is 1-6 or (CH2)n-aryl wherein n can be 0-6, wherein the aryl radical may be optionally substituted up to two times by; pyrrolidin-1-yl, morpholin-1-yl, piperdin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, (CH2)n-phenyl, O-(CH2)n-phenyl, S-(CH2)n-phenyl, SO2-(CH2)-phenyl, where n can be 0-3, or (CH2)n-A-R8 where n can 1-6; A is O, NH, N-(C1-6)-alkyl, NCHO, N(CO-CH3), S, SO or SO2; R8 is (C1-8)-alkyl, (C3-8)-cycloalkyl, where in the alkyl radicals one or more or all of the hydrogens can be replaced by fluorine or one hydrogen may be replaced by OH, OC(O)CH3, OC(O)H, O-CH2-Ph or O-(C1-4)-alkyl; (CH2)m-aryl, wherein m is 0-6 and the aryl can be substituted up to two times by F, Cl, Br, OH, CF3, NO2, CN, OCF3, O-(C1-6)-alkyl, S-(C1-6)-alkyl, SO-(C1-6)-alkyl, (CH2)n-SO2-(C1-6)-alkyl, (CH2)n-SO2-NH2, (CH2)n-SO2-N(-CH-N(CH3)2), (CH2)n-SO2-NH(C1-8)-alkyl, (CH2)n-SO2-N((C1-8)-alkyl)2, (CH2)n-SO2-NH(C3-8)-cycloalkyl, (CH2)n-SO2-N((C3-8)-cycloalkyl)2, (C1-6)-alkyl, (C3-6)-cycloalkyl, COOH, COO(C1-6)-alkyl, COO(C3-6)-cycloalkyl, CONH2, CONH(C1-6)-alkyl, CON((C1-6)-alkyl)2, CONH(C3-6)-cycloalkyl, NH2, NH(C1-6)-alkyl, N((C1-6)-alkyl)2, NH-CO-(C1-6)-alkyl, NH-CO-phenyl, NH-SO2-phenyl, where the phenyl ring may be substituted; NH-SO2-(C1-8)-alkyl, N(C1-6)-alkyl-SO2-(C1-8)-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. The compounds are useful in medicaments for the treatment and prevention of obesity or type II diabetes