GB1139856A - N'-substituted n-aryl sulphonyl ureas, their production and use - Google Patents

Abstract

1,139,856. N - Aryl - sulphonyl carbamoyl derivatives. J. R. GEIGY A.G. 14 Sept., 1967 [15 Sept., 1966], No. 41877/67. Heading C2C. Novel compounds (and salts thereof) of the general formula wherein R 1 represents H, F, Cl, Br, -NH 2 or alkyl, alkoxy, alkylthio or an alkanoyl group and R 2 represents H, or R 1 R 2 represents -(CH 2 ) 3 - or -(CH 2 ) 4 - are prepared: (a) by reacting 1,2,4,5 - tetrahydro - 3H - 3 - benzazepine (or an alkali metal derivative thereof) with either a benzenesulphonyl isocyanate or a reactive functional derivative of a carbamic acid (b) by reacting a reactive functional derivative of 1,2,4,5 - tetrahydro - 3H - 3 - benzazepine- 3-carboxylic acid (e.g. the 3-carbonyl chloride which is obtained by the interaction of phosgene and 1,2,4,5 - tetrahydro - 3H - 3 - benzazepine) with a sulphonamide (c) by desulphurizing a compound of the general formula (e.g.. the intermediate compound wherein R 2 is H and R 1 1 is a 4-methyl group which is obtained by the interaction of p-tolyl-sulphonyl isothiocyanate and 1,2,4,5-tetrahydro-3H-3-benzazepine); or (d) by hydrolysing a compound of the general formula (e.g. the intermediate compound wherein X is Cl, R 2 is H and R 1 <SP>1</SP> is a 4-methyl group which is obtained by interaction of the intermediate referred to in (c) above and phosgene). In the above methods (a), (b), (c) and (d) R 1 <SP>1</SP>R 2 has the same meaning as R 1 R 2 , R 2 is an defined above and R 1 <SP>1</SP> is the same as R 1 except that it may also be a group convertible to an amino group by hydrolysis, reduction or reductive cleavage. Pharmaceutical preparations having a hypoglycaemic action contain as active ingredient the above novel compounds and administration may be orally or parenterally.