IE38177L - Heterocyclic disulphonamides - Google Patents

Abstract

1380009 Sulphonamides PFIZER Ltd 20 Aug 1973 [12 Aug 1972] 37720/72 Heading C2 The novel sulphonamides of general Formula I wherein R<SP>1</SP> represents F, Cl, Br or 3-CF 3 ; X represents O. S, -CH 2 - or a direct bond; y is 0, 1, or 2; m and n are independently 2 or 3 and when X is -CH 2 or a direct bond (R<SP>2</SP>) y represents up to two hydroxy or C 1-4 alkoxy groups or an oxo or C 1-4 alkylene dioxy group attached to the same or different carbon atoms of the heterocyclic ring provided that any oxygen atom in (R<SP>2</SP>) y is separated from the ring nitrogen atom by at least two carbon atoms or when X is O or S (R<SP>2</SP>) y represents up to two C 1-4 alkyl groups or a C 1-4 alkylene group attached to the heterocyclic ring, and their salts with pharmaceutically acceptable cations which may be prepared (except when (R<SP>2</SP>) y is an oxo group) by reacting, a compound of the Formula II with a cyclic amine of Formula III in a solvent such as acetone or dichloromethane, or if (R<SP>2</SP>) y is an oxo group by hydrolysis of the corresponding dialkyl or alkylene ketal, i.e. compounds in which (R<SP>2</SP>) y represents two alkoxy groups or an alkylene dioxy group. 1 - (4 - Methoxypiperidinosulphonyl)- 4- nitro - 2 - trifluoro - methyl benzene is prepared by reacting 4-methoxypiperidine with 4-nitro-2- trifluoromethylbenzene sulphonylchloride and is hydrogenated in methanol i.p.c. Pd. on charcoal to produce 4-(4-methoxypiperidinosulphonyl)-3- trifluoromethylaniline which is in turn diazotized and reacted with CuCl 2 and SO 2 in acetic acid to obtain 4 - (4 - methoxypiperidinosulphonyl)- 3-trifluoromethylbenzenesulphonyl chloride. Pharmaceutical compositions having cerebral vasodilator activity for oral or parenteral administration comprise a compound of the Formula I or pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier. [GB1380009A]