GB1010566A - New benzenesulphonyl-semicarbazides and process for preparing them - Google Patents

Abstract

The invention comprises benzenesulphonyl-semicarbazides of the formula <FORM:1010566/C2/1> and their physiologically tolerable salt with bases and acids, wherein X is a C1-5 alkyl group and -Z-Z1- is an alkylene chain of 3-4 carbon atoms, which may bear one or more C1-4 alkyl substituents. The compounds are prepared by (a) reacting a benzenesulphonyl isocyanate, or a compound which reacts as an isocyanate, with an N,N-alkylene hydrazine; (b) reacting an N,N-alkyleneimino-isocyanate, or a compound which reacts as an isocyanate, with an appropriate benzenesulphonamide; (c) forming a 1-benzenesulphonyl-3-alkyleneimino-parabamic acid and subjecting it to hydrolysis and (d) desulphurizing the corresponding benzenesulphonyl thiosemicarbazide, e.g. by treatment with oxides or salts of heavy metals, or by means of oxidizing agents such as hydrogen peroxide, sodium peroxide or nitrous acid. Compounds which react as isocyanates in processes (a) and (b) include corresponding carbamic or thiocarbamic esters, carbamoyl halides and N1-substituted-urea derivatives in which the N1-position may be substituted by an acyl group or one or two alkyl or aryl radicals or by a benzenesulphonyl radical to form a bis-benzenesulphonyl urea. The products form salts, e.g. with alkali-metals, organic bases and acids such as hydrochloric, sulphuric hydro-bromic and sulphamic acid. Pharmaceutical preparations for the oral treatment of diabetes comprise the above products in admixture or conjunction with a carrier. The preparations are preferably in dosage unit form, such as tablets, containing 0.05-0.5 grams per dosage unit, of the active compound.