IE32985L - Sulphanilamide derivatives - Google Patents

Abstract

1,263,561. Imidazolidine derivatives. J. R. GEIGY A.G. 14 March, 1969 [14 March, 1968 (2)], No. 13513/69. Heading C2C. Novel Compounds I (including salts thereof) wherein R 1 signifies alkyl or alkenyl of at most 5 carbons or an optionally alkyl-substituted cycloalkyl or cycloalkenyl group or a cycloalkyl-alkyl or cycloalkenyl-alkyl group of at most 7 carbons and R 2 is Me or Et, are obtained: (a) by reacting a Compound II (R 3 signifies H, Me, allyl, aryldiaryl- or triarylmethyl and X signifies NH 2 or a group which can be converted into NH 2 by hydrolysis, reduction or reductive cleavage) with a reactive cyanic acid derivative; (b) by reacting a Compound III with a nitrile, R 1 NH.CN or with an alkali or alkaline earth metal salt thereof; (c) by reducing a Compound V (R 1 <SP>1</SP> signifies C 3-5 alkenyl or C 5-7 cycloalkenyl); or (d) by reacting a functional derivative of a sulphonic acid VI with an imidazoline VII (also described as the hydrobromide) Compounds II, III and VII are in general prepared by standard methods. Intermediates to Compounds I, e.g. compounds wherein in place of NH 2 in I there is an MeCONH- group may be produced by methods (a) to (d). N - Tert. butyl - (2 - benzylamino) - propionamide (also described as the hydrochloride), obtained by the interaction of benzylamine and N - tert. - butyl - 2 - chloro - propionamide, reacts with lithium aluminium hydride to afford N<SP>1</SP>- tert.-butyl-N<SP>2</SP>-benzyl-1,2-propane-diamine; the diamine is debenzylated to give N<SP>1</SP>-tert.-butyl- 1,2 - propane - diamine dihydrobromide. The following related compounds are also described: N-butyl-2-benzylamino-propionamide and -butyramide, N<SP>1</SP>-butyl-N<SP>2</SP>-benzyl-1,2-propanediamine and -1,2-butanediamine,and N<SP>1</SP>-butyl-1,2-propane diamine and -1,2-butane-diamine. N-Butyl-andbenzyl-2-chloro-propionamides are obtained by reacting 2-chloro-propionyl chloride with butyl amine or benzylamine (N-butyl-2-chloro-butyramide is similarly obtained); N-benzyl-2-tert.- butylamino -propionamide, N<SP>1</SP>-benzyl-N<SP>2</SP>-tert.- butyl-1,2-propanediamine and N<SP>2</SP>-tert.-butyl-1,2- propane diamine hydrobromide are also described. Pharmaceutical preparations showing hypoglycaemic action contain I as active-ingredient; administration may be orally or parenterally. [GB1263561A]