IE32674L - Sulphanilamide derivatives - Google Patents

Abstract

1,261,572. Imidazolidine derivatives; preparation thereof. J. R. GEIGY A.G. 14 March, 1969 [14 March, 1968 (4)], No. 13508/69. Heading C2C. Compounds I (including salts thereof) wherein R 1 signifies C 1-5 alkyl, or an optionally alkyl-substituted cycloalkyl or cycloalkenyl group, or a cycloalkyl-alkyl or cycloalkenylalkyl group of not more than 7 carbons are prepared: (a) by reacting a compound II (wherein R 2 signifies H, Me aryl-, diaryl- or triaryl-methyl, or allyl and X is a group which can be converted by reduction, reductive cleavage or hydrolysis into NH 2 or if R 2 is H, X can be NH 2 ) with a reactive derivative of cyanic acid; (b) by reacting a compound III with a nitrile, R 1 NH.CN, or alkali or alkaline earth metal salt thereof (X is NH 2 or a group which can be converted by reduction, reductive cleavage or hydrolysis into NH 2 ); (c) by reacting a benzene sulphonamide, X.C 6 H 4 .SO 2 NH 2 , with a reactive ester (e.g. a halide) of a hydroxy compound, CH 2 .OH.CH 2 N(R 1 ).CN {X is as defined in (b)}; (d) by reacting an amine, R 1 .NH 2 with a reactive ester of a compound VII (e.g. a bromide) wherein X<SP>1</SP> is a residue which can be converted by hydrolysis, reductive cleavage or reduction into NH 2 ; (e) by heating an acid addition salt IX (Y is halogen); (f) by reducing a compound X in which R 1 <SP>1</SP> signifies C 3-5 alkenyl or optionally alkyl-substituted cycloalkenyl or cycloalkenylalkyl and X is as defined in (b); (g) by reacting a compound XI with a reactive diester of ethylene glycol; and (h) by reacting a compound XII with a reactive ester of a hydroxy compound R 1 OH. Compounds II, III, VII, IX, X, XI and XII 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 NO 2 - or Me.CO.NH- group, may be produced by methods (a) to (h). N<SP>1</SP> - cyano - N4 - acetyl - sulphanilamide (as the sodium salt) is obtained by the interaction of disodium cyanamide and N-acetyl-sulphanilyl chloride. 4 - (2 - Imidazoline - 2 - ylsulphamoyl) - acetanilide is obtained by the interaction of N- acetyl-sulphanilyl chloride and 2-amino-2-imidazoline hydrochloride. Pharmaceutical preparations showing hypoglycaemic action contain I as active ingredient; administration may be orally or parenterally. [GB1261572A]