GB856443A - Aniline derivatives - Google Patents

Abstract

The invention comprises disulphamoyl-anilines of the formula: <FORM:0856443/IV(b)/1> wherein R1 is halogen, e.g. Cl, Br or F, amino, nitro or C1-5 alkyl or alkoxy, R2 is hydrogen or a C1-5 alkyl radical, R3 is hydrogen, C1-5 alkyl, C1-12 alkanoyl, or a mononuclear aroyl radical or a mononuclear aralkanoyl or aralkenyl radical, containing not more than four carbon atoms in the alkanoyl or alkenoyl residue and R4 and R5 are hydrogen, C1-5 alkyl or C1-6 alkanoyl or form with the nitrogen atom a piperidino, pyrrolidino or morpholino ring, R3 and R3 both being C1-5 alkyl groups when R4 and R5 are both hydrogen; and sodium and potassium salts of those compounds of the above formula wherein R4 is hydrogen and R5 is hydrogen or an alkyl or alkanoyl radical. The invention comprises also processes for preparing compounds of the above formula by treating the corresponding disulphonyl chlorides (obtainable by chlorosulphonating a substituted aniline) with ammonia or an amine NHR4R5 and if desired acylating the product to produce compounds wherein R3, R4 and R5 are acyl groups. Compounds wherein R1 is an amino group may also be prepared by reducing the corresponding nitro compound. Specified products include 5-chloro-2:4-di-(N-methyl-sulpha-moyl)-aniline and the corresponding N-formyl aniline : 2:4-di-(N-acetylsulphamoyl)-, (N:N-dimethylsulphamoyl)- and (piperidino-sulphonyl)-5-chloro-aniline; 5-butyl-2:4-di (N-n-butylsul-phamoyl)- N:N-lauroyl-propyl -aniline; 2:4-di(N:N - n - butyl-ethyl - sulphamoyl) - 5 - methyl - aniline; 2:4-di-(4-morpholinylsulphonyl)-5- propoxy - N-butyl-aniline and 2:4-di- (N:N-dimethylsulphamoyl)-5-propoxy-N-cinnamoyl-aniline. Specifications 826,921, 826,922 and 826,923 are referred to.ALSO:Pharmaceutical compositions having diuretic and natriuretic activity comprise compounds of the formula: <FORM:0856443/VI/1> wherein R1 is halogen, e.g. Cl, Br or F, amino, nitro or C1-5 alkyl or alkoxy, R2 is hydrogen or a C1-5 alkyl radical, R3 is hydrogen, C1-5 alkyl, C1-12 alkanoyl, a mononuclear aroyl radical or a mononuclear aralkanoyl or aralkenoyl radical, containing not more than four carbon atoms in the alkanoyl or alkenoyl residue and R4 and R5 are hydrogen, C1-5 alkyl or C1-6 alkanoyl, or form with the nitrogen atom a pipenidino, pyrrolidino or morpholino ring, R2 and R3 both being C1-5 alkyl groups when R4 and R5 are both hydrogen, or sodium or potassium salts of those compounds wherein R4 is hydrogen and R5 is an alkaonyl or alkyl radical (see Group IV(b)); and a pharmaceutical carrier. The composition may suitably take the form of an injectable solution or the compounds may be admixed with a solid carrier, suitably in the form of tablets. An example describes tablets containing 5-chloro-2 : 4 - disulphamoylaniline. Specifications 826,921, 826,922 and 826,923 are referred to.