GB906850A - Benzothiadiazine-dioxides - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0906850/IV (b)/1> (wherein R1 and R2 are hydrogen or halogen atoms or together form a further bond between the carbon atoms to which they are attached, R3 is a hydrogen atom or an alkyl group of at most 3 carbon atoms, R4 is a halogen atom or a trifluoromethyl group, R5 is a hydrogen or halogen atom or an alkyl group of at most 3 carbon atoms, R6 and R7 are hydrogen atoms or alkyl groups of at most 3 carbon atoms and n is 1 or 2) and their preparation (1) by reacting an appropriately substituted 4-amino-benzene-1,3-disulphonamide with the aldehyde X-CHO (X being the bicyclic alicyclic radical) or a functional derivative thereof; or (2) by reduction of the corresponding 3,4-unsaturatedbenzothiadiazine dioxides (which themselves can be prepared by the method of (1) replacing the aldehyde by the corresponding acid X-COOH). This second method cannot be used to prepare products in which R1 and R2 form an additional bond, but such products produced by method (1) may subsequently be reduced or converted by addition of halogen into the corresponding dihalogen compounds. Examples are given. Bicyclic alicyclic aldehydes X-CHO are prepared by diene synthesis from an unsaturated aldehyde and the corresponding substituted derivative of a cycloalkadiene. Bicyclic alicyclic acids X-COOH are prepared by diene synthesis from a corresponding substituted acrylic acid and a correspondingly substituted cycloalkadiene.ALSO:Pharmaceutical compositions, useful as diuretics, comprise compounds of the formula <FORM:0906850/VI/1> (wherein R1 and R2 are hydrogen or halogen atoms or together form a further bond between the carbon atoms to which they are attached, R3 is a hydrogen atom or an alkyl group of at most 3 carbon atoms, R4 is a halogen atom or a trifluoromethyl group, R5 is a hydrogen or halogen atom or an alkyl group of at most 3 carbon atoms, R6 and R7 are hydrogen atoms or alkyl groups of at most 3 carbon atoms and n is 1 or 2) and carriers therefor. They may take the form of tablets, dragees, capsules or ampoules for oral administration, suppositories for rectal administration, or ampoules containing the active ingredient in a suitable solvent for parenteral administration. Examples are given, additional physiologically active ingredients specified being reserpine, rescinnamine, serpentine and 1-(gammadimethylaminopropyl) - 3,4,4 - trimethyl - 3,5 - ethylene - piperidine dimethosulphate.