Patent IL-113193-A (IL)
Title: N-pyrazin-2-yl- and n-pyrimidin-5-yl- sulphonamides, process for their preparation and pharmaceutical compositions containing them
IPC: C07D213/75
Filed: 1995-03-30
Abstract: Compounds having endothelin receptor antagonistic activity of the formula wherein Q is a naphthyl or biphenyl group; A1, A2 and A3 are attached to a phenyl or benzene ring of Q and are independently selected from hydrogen, (1-6C) alkyl, amino (1-6C) alkyl, hydroxy (1-6C) alkyl, N-[(1-4C) alkyl] amino (1-6C) alkyl, N,N-di(1-4C) alkyl] amino (1-6C) alkyl, (2-6C) alkyl, (2-6C) alkenyl, (2-6C) alkynyl, halogeno (1-6C) alkyl, (1-6C) alkoxy, dihalogeno (1-6C) alkoxy, trihalogeno (1-6C) alkoxy, (2-6C) alkenyloxy, (1-4C) alkoxy (1-6C) alkyl, (1-4C) alkylthio (1-6C) alkyl, (1-4C) 1856 ט" ז באב התשס" ב - July 25, 2002 alkylsulphinyl (1-6C) alkyl, (1-4C) alkylsulphonyl (1-6C) alkyl, (1-4C) alkylsulphonyl (1-6C) alkyl, (1-4C) alkylenedioxy, (3-6C) cycloalkyl, (3-8C) cycloalkyl (1-6C) alkyl, phenyl, phenyl (1-6C) alkyl, phenoxy, phenyl (1-6C) alkoxy, halogeno, hydroxy, mercapto, cyano, nitro, carboxy, (1-6C) alkoxycarbonyl, (2-6C) alkenyloxycarbonyl, phenyloxycarbonyl, phenyl (1-6C) alkoxycarbonyl, (1-6C) alkanoyl, benzoyl, (1-6C) alkylthio, (1-6C) alkylsulphinyl, (1-6C) alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, (1-6C) alkanoylamino, trifluoroacetyl, trifluoroacetamido, N-[(1-4C) alkyl] trifluoroacetamido, benzamido, N-[(1-4C) alkyl] benzamido, carbamoyl, (1-4C) alkylcarbamoyl, di-(1-4C) alkylcarbamoyl, phenylcarbamoyl, sulphamoyl, N-(1-4C) alkylsulphamoyl, N,N-di (1-4C) alkylsulphamoyl, N-phenylsulphamoyl, (1-6C) alkanesulphonamido, benzenesulphonamido, ureido, 3-(1-6C) alkylureido, 3-phenylureido, thioureido, 3-(1-6C) alkylthioureido, 3-phenylthioureido and a group -NRaRb in which Ra and Rb are independently selected from hydrogen, (1-6C) alkyl, phenyl (1-4C) alkyl and (1-6C) alkyl bearing a carboxy or (1-4C) alkoxycarbonyl group, or the group -NRaRb taken together complete a 1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 1-piperidinyl or 2-oxo-1-piperidinyl ring; W, X, Y and Z are independently selected from the following combinations: (1) W and Z are both CR2; X and Y are both N; and (2) W and Y are both CR2; X and Z are both N, R2 has any of the values defined above for A1, A2, or A3; R1 is selected from (1-6C) alkyl, amino (1-6C) alkyl, hydroxy (1-6C) alkyl, N-[(1-4C) alkyl] amino (1-6C) alkyl, N,N-[di(1-4C) alkyl] amino (1-6C) alkyl, (2-6C) alkenyl, 2-[(1-6C) alkoxycarbonyl] ethenyl, 2-phenylethenyl, (2-6C) alkynyl, (1-6C) alkoxycarbonylethynyl, phenylethynyl, halogeno (1-6C) alkyl, (1-3C) alkoxy, dihalogeno (1-3C) alkoxy, trihalogeno (1-3C) alkoxy, (2-6C) alkenyloxy, (1-4C) alkoxy (1-6C) alkyl, (1-4C) alkylthio (1-6C) alkyl, (1-4C) alkylsulphinyl (1-6C) alkyl, (1-4C) alkylsulphonyl (1-6C) alkyl, (3-6C) cycloalkyl, (3-8C) cycloalkyl (1-6C) alkyl, phenyl (1-6C) alkyl, phenyl (1-3C) alkoxy, halogeno, hydroxy, mercapto, nitro, carboxy, (1-6C) alkoxycarbonyl, (2-6C) alkenyloxycarbonyl, phenyloxycarbonyl, phenyl, (1-6C) alkoxycarbonyl, (1-6C) alkanoyl, benzoyl, (1-6C) alkylthio, (1-6C) alkylsulphinyl, (1-6C) alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, (1-6C) alkanoylamino, trifluoroacetyl, trifluoroacetamide, N-[(1-4C) alkyl] trifluoroacetamido, benzamido, N-[(1-4) alkyl] benzamido, carbamoyl, (1-4C) alkylcarbamoyl, di- (1-4C) alkylcarbamoyl, phenylcarbamoyl, sulphamoyl, N-(1-4C) alkylsulphamoyl, N,N-di(1-4C) alkylsulphamoyl, N-phenylsulphamoyl, (1-6C) alkanesulphonamido, benezenesulphonamido, ureido, 3-(1-6C) alkylureido, 3-phenylureido, thioureido, 3-(1-6C) alkylthioureido, 3-phenylthioureido and a group -NRaRb in which Ra and Rb are independently selected from hydrogen, (1-6C) alkyl, phenyl (1-4C) alkyl and (1-6C) alkyl bearing a carboxy or (1-4C) alkoxycarbonyl group, or the group -NRaRb taken together complete a 1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 1-piperidinyl or 2-oxo-1-piperidinyl ring; or when Y is CR2, R1 together with the adjacent R2 is (3-5C) alkylene or (3-5C) alkenylene which together with the carbon atoms to which R1 and the adjacent R2 are attached complete a 5-7 m