Verfahren zur Herstellung von Azidobenzolsulfonylharnstoffen

摘要

The invention comprises benzenesulphonyl ureas of the formula and physiologically tolerable salts thereof with bases, wherein R1 is (a) a saturated or unsaturated aliphatic hydrocarbon radical of 2-8 carbon atoms, which, when it contains 3-8 carbon atoms, may be interrupted by oxygen and/or sulphur, (b) an alicyclic hydrocarbon radical of 3-8 carbon atoms which may be interrupted by an oxygen and/or sulphur atom, (c) a benzyl radical or (d) a b -phenethyl radical. The compounds are prepared by (a) reacting a benzenesulphonyl isocyanate or a compound which during the reaction forms or behaves as an isocyanate, e.g. a benzenesulphonyl carbamic ester, thiocarbamic ester or carbamic halide or a benzenesulphonyl urea, N1-acyl urea or bis-benzenesulphonyl urea, with an amine R1NH2; (b) reacting an isocyanate of the formula R1NCO or a compound which forms or behaves as an isocyanate, e.g. a carbamic ester, thiocarbamic ester or carbamic halide, with a benzenesulphonamide; (c) reacting a guanidine, isourea ether or a tertiary amine salt of a mono R1 substituted parabanic acid, with a benzenesulphonyl halide and hydrolysing the resulting sulphonyl isourea ether, sulphonyl guanidine or sulphonyl parabanic acid; (d) treating a benzenesulphonyl thiourea to replace the sulphur atom of the urea group by oxygen, e.g. by reaction with oxides or salts of heavy metals or oxidizing agents or (e) diazotizing a corresponding aminobenzenesulphonyl urea and treating the product with toluenesulphonamide to give the corresponding azidobenzenesulphonyl urea. Pharmaceutical preparations for the oral treatment of diabetes comprise the above sulphonyl ureas in admixture or conjunction with a carrier, preferably in the form of tablets.