Patent NZ-509395-A (NZ)
Title: Polycyclic thiazolidin-2-ylidene amines useful in treating obesity and diabetes
Inventor: JAHNE GERHARD
IPC: C07D277/60
Filed: 1999-07-03
Abstract: A polycyclic thiazolidin-2-ylidene amine or a physiologically tolerable salt thereof or a physiologically functional derivative thereof has the formula I wherein: A) Y is a direct bond, -CH2- or -CH2-CH2- and X is CH2, CH(CH3), CH(C2H5) or CH(C3H7); R1 is CN; COOH; COO-alkyl; CONH2; CONH-alkyl; CON(alkyl)2; alkyl; alkenyl; alkynyl; O-CH2-CF3; O-CH2-CF2-CF3; O-alkyl and the alkyl radicals may be substituted; S-alkyl; S-(CH2)n- phenyl; SO-alkyl; SO-(CH2)n-phenyl; SO2-alkyl; SO2-(CH2)n- phenyl and the phenyl radical may be substituted; NH2; NH- alkyl; N(alkyl)2; NH-acyl; phenyl; 1,2,3-triazol-5-yl, biphenyl; O-(CH2)n-phenyl, 1- or 2-naphthyl; 2-, 3- or 4- pyridyl; tetrazol-5-yl, 2- or 3-furanyl or 2- or 3-thienyl and the phenyl, biphenyl, naphthyl, pyridyl, 1,2,3-triazol-5- yl, tetrazol-5-yl, furanyl or thienyl rings in each case may be substituted; R1' is H, F, Cl, Br, I, CH3, CF3, O-alkyl, NO2, SO2-NH2, SO2NH-alkyl, SO2N[alkyl]2 or R1; R2 is H, alkyl, cycloalkyl, optionally substituted (CH2)n'- phenyl, (CH2)n'-thienyl, (CH2)n'-pyridyl, (CH2)n'-furyl, C(O)-(CH2)n'-phenyl, C(O)-(CH2)n'-thienyl, C(O)-(CH2)n'- pyridyl, or C(O)-(CH2)n'-furyl; n' is 0-5; and n is 0 to 6; R3 is H, alkyl, F, CN, N3, O-alkyl, CH2COO-alkyl, CH2-COO- cycloalkyl, CH2-COOH, CH2-CONH2, CH2-CONHCH3, CH2-CON(CH2)2 or optionally substituted (CH2)n'-phenyl, (CH2)n'-thienyl, (CH2)n'-pyridyl, or (CH2)n'-furyl; R4 and R5 are independently is alkyl, cycloalkyl, optionally substituted (CH2)n'-phenyl, (CH2)n'-thienyl, (CH2)n'- pyridyl, or (CH2)n'-furyl or together form a -CH2-CH2-, -CH2- C(CH3)2-, --CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2- or B) R1 and R1' independently are H; F; Cl; Br; I; NO2 ; CN; COOH; COO-alkyl; CONH2; CONH-alkyl; CON[alkyl]2; alkyl; alkenyl; alkynyl; O-alkyl; O-CH2-CF3 or O-CH2-CF2-CF3 and the alkyl radicals may be substituted; S-alkyl; S-(CH2)n- phenyl; SO-alkyl; SO--(CH2)n-phenyl; SO2-alkyl; or SO2- (CH2)n phenyl; and the phenyl may be substituted; SO2NH- alkyl; SO2N[alkyl]2; NH2; NH-alkyl; N(alkyl)2; NH-acyl; phenyl; biphenyl; or O-(CH2)n-phenyl; 1,2,3-triazol-5-yl, tetrazol-5-yl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl and the phenyl, 1, 2,3-triazol- 5-yl, tetrazol-5-yl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case may be substituted; R3 is alkyl, F, CN, N3, O-alkyl, CH2COO-alkyl, CH2-COO- cycloalkyl, CH2-COOH, CH2-CONH2, CH2-CONHCH3, CH2-CON(CH2)2 or optionally substituted (CH2)n'-phenyl, (CH2)n'-thienyl, (CH2)n'-pyridyl, or (CH2)n'-furyl; and X, Y, R2, R4 and R5 are as defined above or C) R2 is alkyl, alkenyl, alkynyl, cycloalkyl, (CH2)n'- phenyl, (CH2)n'-thienyl, (CH2)n'-pyridyl, (CH2)n'-furyl, C(O)-(CH2)n'-phenyl, C(O)-CH2)n'-thienyl, C(O)-(CH2)n'- pyridyl, or C(O)-(CH2)n'-furyl, and wherein phenyl, thienyl, pyridyl, and furyl in each case may be substituted; R3 is as defined above for part A); R1 and R1' are as defined above for Part B) and X, Y, R4 and R5 are as defined above or D) X is optionally substituted CH(phenyl); R1 and R1' are as defined for part B and Y, R2 to R5 are as defined above for part A or E) R1 is H, F, Cl, Br, I, CH3, CF3, or O-alkyl; R1' is H, F, Cl, Br, I, or NO2; R2 is H; R3 is H, or alkyl; R4 and R5 are independently optionally substituted phenyl and X and Y are as defined above for part A. The compounds are useful for treating obesity and diabetes,