GB899037A - Benzothiadiazine compounds - Google Patents

Abstract

The invention comprises dihydrobenzothiadiazine compounds of the formula <FORM:0899037/IV (b)/1> in which R1 is an alkenyl radical, R2 is hydroge or an unsubstituted or halogen substituted aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aromatic or araliphatic hydrocarbon radical, R3 is hydrogen or an alkyl group, R4 is a halogen atom or an alkyl or haloalkyl group and R5 is hydrogen or an alkyl or alkenyl group, and physiologically tolerable salts, e.g. alkali-metal salts, of those compounds. The compounds are made by (a) reacting an appropriate dihydrobenzothiadiazine-1,1-dioxide, unsubstituted in the 2-position, or its alkali-metal salt, with a reactive ester of an alcohol R1OH such as a halide, sulphate or organic sulphonate or (b) reacting a 2 : 4-disulphamoyl aniline of the formula <FORM:0899037/IV (b)/2> with an aldehyde R2-CHO or a polymer or reactive derivative thereof. Preferred products include compounds wherein R4 is chlorine or a trifluoromethyl group, R5 is a hydrogen atom or an alkenyl group of 3-5 carbon atoms and R2 is an alkenyl group of 3-5 carbon atoms such as an allyl group. The products are used pharmaceutically (see Group VI). 2 : 4-Disulphamoyl anilines of the formula II above are made by reacting the corresponding 2 : 4-disulphonyl chlorides with an amine R1NH2 and treating the resulting 2-sulphamoyl-4\sulphochloride with ammonia or an amine R5NH2.ALSO:Pharmaceutical preparations having diuretic and sodiouretic activity comprise dihydrobenzothiadiazine compounds of the formula <FORM:0899037/VI/1> in which R1 is an alkenyl radical, R2 is hydrogen or an unsubstituted or halogen substituted aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aromatic or araliphatic hydrocarbon radical, R3 is hydrogen or an alkyl group, R4 is a halogen atom or an alkyl or haloalkyl group and R5 is a hydrogen atom or an alkyl or alkenyl group, or physiologically tolerable salts thereof (see Group IV (b)), in admixture or conjunction with a pharmaceutical carrier suitable for enteral, e.g. oral, or parenteral administration. The preparations suitably take the form of tablets, dragees, capsules, solutions, suspensions or emulsions and may contain, in addition to conventional excipients, stabilizing, preserving and wetting or emulsifying agents, salts for varying the osmotic pressure or buffers, and other therapeutic substances, e.g. hypotensive agents such as reserpine, rescinnamine, deserpidine, syrosingopine, germine, protoveratrine, hydralazine, dihydralazine and chlorisondamine.