GB895430A - Tryptamine derivatives and acid addition salts thereof - Google Patents

Abstract

The invention comprises tryptamines of the formula <FORM:0895430/IV (b)/1> or acid addition salts thereof wherein Ar represents a monocarbocyclic aryl group, preferably phenyl or phenyl substituted by one or more of the following atoms or groups: halogen, C1-4, alkyl, C1-4 alkoxy, C1-4 alkylmercapto, nitro hydroxy, C1-4 acyloxy or methylenedioxy, R1 is a hydrogen atom or a C1-4 alkyl or a monocarbocyclic aryl group as defined above and R is a C1-4 alkyl group, and the preparation thereof by reacting a 1-ArCH2-2-R1-5-RS-3-phthalimidoethylindole with hydrazine hydrate. 1-ArCH2-2-R1-5RS-3- Phthalimido - ethylindoles are prepared by reacting a monocarbocyclic aryl aldehyde with a 4-alkylmercaptoaniline to give a Schiff base, which is reduced to N - monocarbocyclic arylmethyl - 4 - alkylmercaptoaniline, the amine is converted into the nitrosoamine which in turn is reduced to the N - monocarbocyclic arylmethyl - 4 - alkyl - mercapto - phenylhydrazine and the last named compound is reacted with g -phthalimidobutyraldehyde or 3-phthalimidopropyl ketones. The hydrazines may also be prepared by reacting a 4 - alkylmercaptophenyl - hydrazine with a monocarbocyclic arylmethyl halide and an alkali metal amide in liquid ammonia and in the presence of a condensation catalyst such as ferric salts, iron or ferric oxide. g -Phthalimidobutyraldehyde is prepared by reducing g -phthalinidobutyronitrile with stannous chloride and hydrolysing the stannic aldimonium chloride formed. 3-Phthalimidopropyl alkyl and monocarbocyclic aryl ketones are prepared by reacting potassium phthalimide with a 3-chloropropyl alkyl ketone and by reacting g -phthalimido butyroyl chloride with a monocarbocyclic aryl hydrocarbon respectively.ALSO:Hypertensive compositions comprise tryptamines of the formula <FORM:0895430/VI/1> or addition salts thereof with inorganic or organic acids, wherein Ar is a monocarbocyclic aryl group (including phenyl optionally substituted by the following atoms or groups: halogen, C1-4-alkyl, C1-4-alkoxy, C1-4-alkyl-mercapto, nitro, hydroxy, C1-4 acyloxy, methylenedioxy), R is a C1-4-alkyl group and R1 is a hydrogen atom or a C1-4-alkyl or a monocarbocyclic aryl group as defined above, optionally in combination with other hypertensive agents, e.g. reserpine, in forms suitable for enteral or parenteral administration (e.g. tablets, capsules or sterile solutions).