GB1308210A - Benzene-sulphonyl urea compounds - Google Patents

Abstract

1308210 Benzenesulphonyl urea compounds SCHERICO Ltd 26 Aug 1970 [27 Aug 1969 14 Nov 1969 19 Dec 1969] 41106/70 Heading C2C Novel compounds of the Formula I their d- or l-isomers or racemates and pharmaceutically acceptable salts thereof, wherein X and X<SP>1</SP> are hydrogen, methyl, methoxy or halogen, Y is C 1-6 alkyl, hydroxy, C 1-6 alkoxyl or halogen and Y<SP>1</SP> is hydrogen, C 1-6 alkyl or alkoxy, hydroxy or halogen and R is hydrogen or methyl may be prepared by (a) reacting a reactive derivative including isocyanates of a carbamic acid, E<SP>1</SP>:NCOOH, with an amino compound E<SP>2</SP>:NH or a reactive derivative thereof, wherein one of E<SP>1</SP> and E<SP>2</SP> is and the other is (b) reacting a reactive derivative of an acid and a urea wherein p is 1 or 2; (c) reducing a compound of the Formula IA wherein W<SP>1</SP> and W<SP>2</SP> are hydrogen, halogen or diazonium, R<SP>2</SP> is a group removable by hydrogenolysis to give R 2 =H, n is 0 or 1 and M is one of the following groups wherein R<SP>1</SP> is hydrogen, methyl or a group removable by hydrogenolysis to give R<SP>1</SP> = H and L is a methylene or a group CHBH or C = B where B is oxygen or sulphur, wherein compound IA differs from compound I in at least one structural feature; (d) oxidizing a compound of the Formula XV wherein m is 0 or 1; (e) subjecting a compound XVI (i) to hydrolysis when A is imino or iminolether or (ii) reaction with mercuric oxide or silver oxide when A is sulphur; (f) modifying the substituents on the benzene rings to form X,X<SP>1</SP>, Y, Y<SP>1</SP> components as in Formula I. Pharmaceutical compositions of the compounds I with the usual excipients show antiarrhythmic and anti-angina activity when administered orally or parenterally.