Patent NZ-520925-A (NZ)
Title: Substituted 8, 8a-dihydro-3aH-indeno[1,2-d]thiazoles, a method for their production and their use as medicaments
Inventor: JAEHNE GERHARD
IPC: A61P3/04
Filed: 2001-02-12
Abstract: Compounds of formula (I) are described wherein: R1, R1' are 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 alkyl, alkenyl, or alkynyl radicals one or more or all hydrogen 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)nphenyl, where n is 0-6 and the phenyl radical can be substituted; NH2, NH(C1-6)alkyl, N[(C1-6)alkyl]2, NH(C1-7)acyl, phenyl, biphenylyl, O(CH2)n-phenyl, 1,2,3-triazol-5-yl, or tetrazol-5-yl, where n is 0-6, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the rings can be substituted; 1,3,4-oxadiazol-2-yl; 2-amino-1,3,4-oxadiazol-5-yl, where the amino function can be mono- or disubstituted; 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 is 0-5 and in which any of phenyl, thienyl, pyridyl or furyl may be optionally substituted; R3 is H, (C1-6)-alkyl, F, Cl, Br, CN, N3, O-(C1-6)-alkyl, (CH2)n-phenyl, (CH2)n-thienyl, (CH2)n-pyridyl, (CH2)n-furyl, where n is 0-5 and in which any of phenyl, thienyl, pyridyl or furyl can be optionally substituted; (C2-6)-alkynyl, (C2-6)-alkenyl, OC(O)CH3, (CH2)n -C(O)O(C1-6)-alkyl, (CH2)n-C(O)OH, (CH2)n-C(O)NH2, (CH2)n-C(O)NHCH3 or (CH2)n-C(O)N(CH3)2, where n is 0-3; R4 is (C1-8)-alkyl, (C3-7)-cycloalkyl, (C2-6)-alkenyl, (C2-6)-alkynyl, (C4-7)-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-(C1-4)-alkyl; is (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 or (CH2)n-heteroaryl, where n is 0-6 wherein the aryl radical or the heteroaryl radical may be optionally substituted; (CH2)n -A-R8, where n is 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 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; is (CH2)m-aryl, wherein m is 0-6 and aryl is phenyl, thienyl or pyridyl and the aryl moiety may be optionally substituted up to two times; 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; R5 is H; R6 is Cl, Br, OH, O-(C1-6)-alkyl, O-(CH2)n -aryl, O-(CH2)n -heteroaryl wherein n is 0-6 and aryl is phenyl and heteroaryl is 2-, 3- or 4-pyridyl or 2- or 3-thienyl; O-C(O)-H, O-C(O)-(C1-6)-alkyl, O-C(O)-(C3-8)-cycloalkyl, O-C(O)-aryl, O-C(O)-heteroaryl, SH, S-(C1-6)-alkyl, S-(CH2)n -phenyl, wherein n is 0-6, S-C(O)-(C1-6)-alkyl, S-C(O)-(C3-8)-cycloalkyl, S-C(O)-phenyl; SO-(C1-6)-alkyl, SO-(CH2)n -phenyl, wherein n is 0-6, SO2-(C1-6)-alkyl, SO2-(CH2)n-phenyl, wherein n is 0-6, NH2, NH-(C1-6)-alkyl, NH-(C3-7)-cycloalkyl, N[(C1-6)-alkyl]2, morpholin-4-yl, pyrrolidin-1-yl, piperidin-1-yl, piperazin-1-yl, 1-methylpiperazin-4-yl, 1-benzylpiperazin-4-yl, NH-phenyl, NH-CH2-phenyl, NH-C(O)-(C1-6)-alkyl or NH-C(O)-phenyl; or R5 and R6 can together form at least =O, =NOH. The compounds are useful in medicaments for the treatment or prophylaxis of obesity or types II diabetes.