Patent ID: 6656957
Filing Date: 2003-12-02
Classification: A61P,C07D,C07F

Abstract:
A compound of formula I whereinX represents an optionally halo-substituted (C2-4)alkynylene group bonded via vicinal unsaturated carbon atoms, R1 is (C1-4) alkyl, (C1-4)alkoxy, hydroxy(C1-4)alkyl, cyano, ethynyl, carboxy, (C1-4)alkoxycarbonyl, di(C1-4)alkylamino, (C1-6)alkylaminocarbonyl, trifluoromethylphenylaminocarbonyl, R2 is hydrogen, hydroxy, (C1-4) alkyl, hydroxy (C1-4) alkyl, (C1-4) alkoxy, carboxy, (C2-5)alkanoyloxy, (C1-4) alkoxycarbonyl, di(C1-4)alkylamino(C1-4)alkanoyl, di(C1-4)alkylaminomethyl, 4-(4-fluoro-benzoyl)-piperidin-1-yl-carboxy, 4-t.-butyloxycarbonyl-piperazin-1-yl-carboxy, 4-(4-azido-2-hydroxybenzoyl)-piperazin-1-yl-carboxy or 4-(4-azido-2-hydroxy-3-iodo-benzoyl)-piperazin-1-yl-carboxy, R3 is hydrogen, (C2-4) alkyl, carboxy, (C1-4)alkoxycarbonyl, (C1-4)alkylcarbamoyl, hydroxy(C1-4)alkyl, di(C1-4)alkylaminomethyl, morpholinocarbonyl or 4-(4-fluoro-benzoyl)-piperidin-1-yl-carboxy, R4 is hydrogen, hydroxy, (C1-4)alkoxy, carboxy, (C2-5)alkanoyloxy, (C1-4)alkoxycarbonyl, amino(C1-4)alkoxy, di(C1-4)alkylamino(C1-4)alkoxy, di(C1-4)alkylamino(C1-4)alkyl, carboxy (C1-4)alkylcarbonyl, (C1-4)alkoxycarbonyl(C1-4)alkoxy, hydroxy(C1-4)alkyl, di(C1-4)alkylamino(C1-4)alkoxy, m-hydroxy-p-azidophenylcarbonylamino(C1-4)alkoxy, and R5 is a group of formula â€ƒwherein Ra and Rb independently are hydrogen, hydroxy, halogen, nitro, cyano, carboxy, (C1-4)alkyl, (C1-4)alkoxy, hydroxy(C1-4)alkyl, (C1-4)alkoxycarbonyl, (C2-7)alkanoyl, (C2-5)alkanoyloxy, (C2-5)alkanoyloxy(C1-4)alkyl, trifluoromethyl, trifluoromethoxy, trimethylsilylethynyl, (C2-5)alkynyl, amino, azido, amino (C1-4)alkoxy, (C2-5)alkanoylamino(C1-4)alkoxy, (C1-4)alkylamino(C1-4)alkoxy, di(C1-4)alkylamino(C1-4)alkoxy, (C1-4)alkylamino, di(C1-4)alkylamino, monohalobenzylamino, thienylmethylamino, thienylcarbonylamino, trifluoromethylphenylaminocarbonyl, tetrazolyl, (C2-5)alkanoylamino, benzylcarbonylamino, (C1-4)alkylamino carbonylamino, (C1-4)alkoxycarbonyl-aminocarbonylamino or (C1-4)alkylsulfonyl, Rc is hydrogen, fluorine, chlorine, bromine, hydroxy, (C1-4)alkyl, (C2-5)alkanoyloxy, (C1-4)alkoxy or cyano, and Rd is hydrogen, halogen or (C1-4)alkyl, provided that in compounds wherein R2, R3 and R4 are hydrogen, when R1 is methyl, R5 is different from phenyl, 3-methylphenyl, 6-methylpyridin-2-yl and 3-methoxyphenyl, in free form or in form of a pharmaceutically acceptable salt.