GB797474A - Sulphonylurea derivatives - Google Patents

Abstract

The invention comprises compounds of the general formula: <FORM:0797474/IV (b)/1> wherein W is an amino group, an acylated amino group or a nitro group and R is a saturated or unsaturated open chain or cyclic hydrocarbon radical containing at least one hetero atom selected from sulphur, oxygen, nitrogen and their alkali metal salts, together with processes for the manufacture thereof by (1) reacting a compound of the general formula: <FORM:0797474/IV (b)/2> or an alkali metal salt thereof with an isocyanic acid ester, RNCO; (2) reacting a compound of the general formula: <FORM:0797474/IV (b)/3> or a benzenesulphonyl compound capable of producing such a benzenesulphonyl isocyanate by splitting or transposition under the reaction conditions, with an amine of the general formula R.NH2; this amine may be a constituent of a salt-like nature of the benzene sulphonyl compound used as starting material; (3) reacting a compound of the general formula: <FORM:0797474/IV (b)/4> with an isourea alkyl ester of the general formula HN = C(O.Alkyl).NHR, and treating the resulting substituted sulphonylisourea with a hydrogen halide; (4) reacting a compound of the general formula: <FORM:0797474/IV (b)/5> with an oxidizing agent or a hydrolysing agent; (5) reacting a substituted carbamic acid chloride with a sulphanilamide salt; and (6) treating a sulphanilguanidine with an alkaline hydrolysing agent. In examples p-nitrobenzenesulphonamide is condensed with 3-ethoxypropyl isocyanic ester, the product isolated and reduced by hydrogen in the presence of a nickel catalyst to yield N1 - 3 - ethoxypropyl - N2 - sulphanilyl urea; bis - (acetylsulphanilyl) - urea is reacted with 3-methoxypropylamine to form the 3-methoxypropylamine salt of bis-(acetylsulphanilyl)-urea which is converted into N1-3-methoxypropyl - N2 - acetylsulphanilyl urea by heating, N1 - 3 - methoxypropyl - N2 - sulphanilyl urea being obtained on saponification; bis - (acetylsulphanilyl) - urea is similarly reacted with threo - l - 4 - phenyl - 5 - amino - 1,3-dioxane, b - ethoxyethylamine, 3 - ethylmercaptopropylamine and 3-methylmercaptopropylamine to yield the corresponding N1-substituted - N2 - sulphanilylureas; and acetyl sulphanilylmethyl urethane is reacted with 3-propoxypropylamine, a - aminopyridine, 2-ethoxy - 5 - aminopyridine, 2 - aminopyrimidine, 2,4 - dimethyl - 6 - amino - pyrimidine and 4-aminopyridine, any salts formed being decomposed by heat, to give the corresponding N1-substituted-N2-acetylsulphanilyeureas from which the amino compounds are prepared by saponification.