GB895625A - New benzene-sulphonyl benzyl-ureas and process of preparing them - Google Patents

Abstract

The invention comprises sulphonyl ureas of the formula <FORM:0895625/IV (b)/1> and salts thereof with pharmaceutically tolerable bases, wherein R is hydrogen or an alkyl or alkoxy radical containing up to 6 carbon atoms, A is hydrogen, methyl or ethyl and B is hydrogen or an alkyl or alkoxy radical of up to 3 carbon atoms, and their preparation by known methods for preparing sulphonyl ureas, viz.: reacting a benzene sulphonamide with an aralkyl isocyanate or a benzenesulphonyl isocyanate with an aralkylamine; reacting a benzene sulphonamide with an aralkyl urethane or a benzenesulphonyl urethane with an aralkylamine; reacting a benzene sulphonamide, suitably in the form of its salt, with an aralkyl carbamoyl halide, or a benzenesulphonyl carbamoyl halide with an aralkylamine; reacting a benzenesulphonamide with a compound containing the aralkyl urea residue B-C6H4.CHA.NH.CO.NH-; forming the corresponding isourea ether and hydrolysing; eliminating sulphur from the corresponding thiourea; hydrolysing the corresponding sulphonyl guanidine, and oxidising a corresponding sulphonyl or sulphinyl urea. N - p - Methylbenzenesulphonyl - N1 - benzyl - thiourea is made by the action of sodium p-toluenesulphonamide on benzyl mustard oil. N - p - isopropylbenzenesulphonyl - N1 - benzyl isourea methyl ether is made by treating benzyl urea with dimethyl sulphate and reacting the product with isopropylbenzene sulphochloride. Pharmaceutical preparations for the treatment of diabetes comprise the above sulphonyl ureas in admixture or conjunction with a pharmaceutical carrier, preferably in a form suitable for oral administration, such as a tablet, optionally containing such conventional excipients as talcum, starch, lactose, tragacanth or magnesium stearate. Specifications 604,259 and 808,071 are referred to.