GB850982A - Improvements in and relating to substituted ureas - Google Patents

Abstract

The invention comprises thiophene sulphonyl ureas of the formula : <FORM:0850982/IV(b)/1> in which R is an alkyl, alkenyl, cycloalky or aralkyl residue or an alkyl radical interrupted by hetero atoms, e.g. O or S, X is hydrogen, halogen or a methyl, amino, acylamino or sulphonylamino group and Y is hydrogen, halogen or a methyl group and their preparation by the following methods (a) treating a sulphonamide of the formula <FORM:0850982/IV(b)/2> with an alkali metal salt of an isocyanate R,N = C = O or with a reactive functional derivative of a carbamic acid R,NH - COOH such as the ester, halide, amide or nitrile and partially hydrolysing the resulting thiophene sulphonyl guanidine in cases when this is formed as the initial product ; (b) treating a sulphonyl isocyanate of the general formula <FORM:0850982/IV(b)/3> or a reactive functional derivative of the corresponding thiophenesulphonyl carbamic acid such as an ester, halide, amide or nitrile with an amine RNH2 and when necessary partially hydrolysing the resulting thiophenesulphonyl guanidine if first obtained and (c) reacting a thiophene sulphonyl halide <FORM:0850982/IV(b)/4> wherein Z is chlorine or bromine, with an ether of the iso-form of a urea H2N-CO-NHR, especially the methyl or ethyl ether and partially hydrolysing the resulting thiophenesulphonyl isourea ether. The products are used as oral anti-diabetics. Examples describe the preparation of N-thiophenesulphonyl-(2)-N1-n-butyl urea and its 5-chloro and 5-bromo derivatives. Similarly prepared are N-thiophenesulphonyl-(2)-N1-n-propyl, -isopropyl, -isobutyl, -sec-butyl, -isoamyl and -cyclohexyl urea; N-(5-chloro-thiophenesulphonyl-(2))-N1-isopropyl, -n-butyl, -isobutyl, -sec-butyl, -isoamyl and -allyl urea, N-(5-bromothiophenesulphonyl-(2))-N1-n-propyl, -isopropyl, -isobutyl, sec-butyl, -isoamyl and -cyclohexyl urea and N(2 : 5-dibromothiophene-(2))- and N(2 : 5-dichlorothiophene-(2))-, N2-n-butyl urea.