GB988773A - Sulphonyl ureas - Google Patents

Abstract

The invention comprises hydrindenesulphonylureas (indanesulphonylureas) of the formula <FORM:0988773/C2/1> and salts such as the alkali and alkaline earth metal salts thereof, wherein R is an alkyl e.g. methyl, ethyl, propyl, isopropyl, butyl, t-butyl or amyl, alkenyl e.g. allyl, cycloalkyl e.g. cyclobutyl, cyclopentyl or cyclohexyl, aryl e.g. naphthyl, phenyl or an aralkyl group e.g. a phenethyl or benzyl group. The compounds are made by (a) reacting a salt of the hydrindenesulphonamide, such as an alkali-metal or alkaline earth metal salt, with an isocyanate R.NCO or a corresponding carbamoyl chloride or urethane; (b) reacting a hydrindenesulphonamide with a chloroformic ester, phosgene or an unsubstituted urethane or urea and reacting the resulting product with a primary amine; (c) reacting a hydrindenesulphonamide with a substituted thiourea and either desulphurizing the product or converting it to the guanidine analogue by treatment with silver nitrate and subsequently hydrolysing with a base to the sulphonyl urea compound and (d) reacting a hydrindenesulphonyl chloride with an isourea alkyl ether and hydrolysing the product. Ethyl hydrindene-4-sulphonyl carbamate is made by reacting hydrindene-4-sulphonic acid with thionyl chloride, treating the resulting hydrindene-4-sulphonyl chloride with ammonia to give the sulphonamide and reacting this with ethyl chlorocarbonate. 1 - n - Butyl - 3 - (hydrindene - 4 - sulphonyl)-thiourea is made by reacting hydrindene-4-sulphonamide with 1-n-butyl-thoiurea. 1 - n - Propyl - 3 - (hydrindene - 4 - sulphonyl)-guanidine hydrochloride is made by treating hydrindene-4-sulphonyl chloride with n-propylguanidine. 1 - (Hydrindene - 5 - sulphonyl) urea is made by reacting hydrindene-5-sulphonamide and urea. Pharmaceutical preparations having hypoglycemic activity comprise the above compounds of the invention embodied in conventional dosage forms such as tablets or capsules.