GB1124285A — Novel perhydro-1,2,4-thiadiazine dioxides-(1,1), their preparation and compositionscontaining them

USPTO Abstract

Novel perhydro - 1,2,4 - thiadiazine dioxides -(1,1) of general formulae <FORM:1124285/C2/1> wherein each of R1 and R2, which may be the same or different, is a hydrogen atom, an alkyl group having 1-8 carbon atoms, a cycloalkyl group, an aralkyl group, an aryl group, or a methylene group attached to a nitrogen atom of another perhydrothiadiazine dioxide nucleus, or where together with the perhydrothiadiazine dioxide ring, to which they are attached, form a ring of perhydrothiadiazine dioxide nuclei separated by methylene groups joining nitrogen atoms of different nuclei, R1 and R2 may also have substituents such as halogen, esterified carboxy or dialkylamino, and the physiologically acceptable acid addition salts thereof, are prepared by ring closure of a taurine amide of general formula (IV) R3-NH-CH2-CH2-SO2-NH-R4 in which R3 and R4 represent hydrogen atoms, alkyl groups having 1-8 carbon atoms, cycloalkyl groups, aralkyl or alkyl groups, or of an acid addition salt thereof, by reaction with formaldehyde or a substance liberating formaldehyde. Compounds of the first general formula above are also obtained by catalytic hydrogenation in the presence of a platinum oxide catalyst, of compounds wherein the perhydro - 1,2,4 - thiadiazine dioxide ring is joined to a similar ring by a methylene group attached to the 4-position of each ring. Pharmaceutical compositions having bactericidal and fungicidal activity and which may be administered orally or topically in the form of tablets, dragees, capsules, lozenges, suppositories, ampoules for injection, syrups, linctuses, ointments, lotions, pastes, solutions, or aerosol sprays, contain a compound of the first general formula above or a physiologically acceptable acid addition salt thereof, as the active ingredient. Taurine amides of the formula R3NHCH2CH2SO2NHR4 wherein R1 and R2 have the above significance, are prepared by reacting CH2 = CHSO2NHR1 with ammonia or a primary amide, or by reacting the phthalimido derivative of an acid halide of taurine with a primary amine and removing th phthalyl group in the product.