GB884738A - Sulphonyl-urethanes and a process for preparing them - Google Patents

Abstract

The invention comprises sulphonyl urethanes of the formula R.SO2.NH.COO.CH2CH2.O.R, wherein R is a phenyl radical optionally bearing one or two halogen or C1-6 alkyl or alkoxy substituents or is a naphthyl-(2), 5,6,7,8-tetrahydronaphthyl-(2), phenylalkyl (of up to 10 carbon atoms), 4-phenoxyphenyl, 4-diphenyl or an alkyl, cycloalkyl or cycloalkyl-alkyl radical of up to 8 carbon atoms and R1 is an alkyl radical of 1-4 carbon atoms and non-toxic basic salts thereof; and their preparation (a) by reacting a sulphonyl isocyanate RS2NCO or a compound convertible thereto under the reaction conditions with an a -hydroxy-b -alkoxyethane; (b) by re-esterifying a sulphonylurethane RSO2NHCOOR2 (R2 is a lower alkyl group) with an a -hydroxy-b -alkoxy-ethane; (c) by splitting a sulphonyl urea RSO2.NH.CO.NHR2, an acyl sulphonyl urea RSO2.NH.CO.NH.3 (R3 is an aliphatic, aromatic or mixed aliphatic/aromatic acyl radical) or a substituted sulphonyl urea R.SO2.NH.CO.N1-(in which the N1 atom is disubstituted), by treatment with a a -hydroxy-b -alkoxy ethane and (d) by reacting a sulphonamide RSO2NH2 or its alkali-metal salt with a haloformic ester. Suitably R is phenyl or a p-chloro-, m-chloro-, 3,4-dichloro-, p-ethyl-, p-isopropyl-, m-methyl, p-methyl, o-methyl-, p-methoxy-, 3,4-dimethoxy- or 2-methyl-6-chloro-phenyl group or is a 2-naphthyl, benzyl, cyclohexyl or butyl group and R1 is methyl, or R is p-methylphenyl and R1 is ethyl or butyl. The compounds are used for the treatment of coccidiosis in poultry suitably in the form of a salt such as an alkalimetal salt. N-(4-Chlorobenzenesulphonyl)-N1-butyryl urea is made by p heating 4-chlorobenzenesulphonylurea and butyric anhydride in the presence of concentrated sulphuric acid. Specification 845,042 is referred to.ALSO:Preparations for the treatment of poultry coccidiosis comprise sulphonyl urethanes of the formula R.SO2.NH.COO.CH2CH2.O.R1 wherein R is a phenyl radical optionally bearing one or two halogen or C1-6 alkyl or alkoxy substituents, or is a naphthyl-(2), 5 : 6 : 7 : 8-tetrahydronaphthyl-(2), phenylalkyl (of up to 10 carbon atoms), 4-phenoxyphenyl, 4-diphenyl, or alkyl, cycloalkyl or cycloalkyl-alkyl radical of up to 8 carbon atoms and R1 is an alkyl radical of 1-4 carbon atoms or non-toxic basic salts thereof (see Group IV (b)) in admixture with a pharmaceutical carrier. Preferred preparations comprise the sulphonyl urethane or salt thereof in admixture with tetracycline base, or tetracycline hydrochloride, or a tetracycline derivative such as pyrrolidinomethyl-tetracycline, a substance delaying the oxidation of tetracycline, e.g. sodium pyrrosulphate and a carrier. Specification 845,042 is referred to.