GB1174152A - Sulphanilamide Derivatives and Process for Their Production - Google Patents

Abstract

1,174,152. 1-Sulphanilyl-imidazolidines. J. R. GEIGY A.G. 23 March, 1967 [24 March, 1966], No. 13708/67. Heading C2C. Novel compounds of formula (wherein R is C 1-5 alkyl, a monocycloaliphatic hydrocarbon group of up to 10 carbon atoms optionally substituted by one or two C 1-3 alkyl groups, or a monocycloaliphatic hydrocarbonmethyl or -ethyl group wherein the monocycloaliphatic radical contains up to 10 carbon atoms) and their pharmaceutically acceptable addition salts with organic or inorganic acids, are prepared by reacting a reactive functional derivative of a para-X-benzenesulphonic acid (wherein X is a radical convertible into an amino group by hydrolysis, reduction or reductive cleavage) with a compound of formula or with an acid addition salt of such a compound in the presence of an acid binding agent, converting the group X in the product to amino, and if desired salifying the resulting compound of Formula I with an appropriate organic or inorganic acid. 2 - Amino - 2 - imidazolines of Formula III are prepared from 2-imino-imidazolidine by reaction with an alkyl halide or monocycloaliphatic halide, or from N-(R)-ethylenediamines (i) by reaction with cyanogen chloride, or (ii) by reaction with CS 2 to form 1-(R)- imidazolidine - 2 - thiones which are converted with CH 3 I into 2-methylthio-2-imidazolinium iodides which are reacted with ammonia, or (iii) by reaction with a salt of S-methyl-isothiourea and heating the resulting salt of an N-(2-substituted amino-ethyl)-guanidine. The compounds of Formula I and their pharmaceutically acceptable salts with organic and inorganic acids are stated to possess hypoglycaemic activity and may be made up with carriers into pharmaceutical compositions suitable for oral or parenteral administration.