GB730213A - Antispasmodics - Google Patents

Abstract

The invention comprises: (1) substituted o -aminoalkylphenothiazines of formula <FORM:0730213/IV (b)/1> wherein A is sulphur, or an -NR- group, R being hydrogen or methyl, R1 is an alkylene group containing from 2 to 4 carbon atoms, R2 and R3 are lower alkyl groups, each containing up to 4 carbon atoms inclusive or together with the N denote a monocyclic, heterocyclic, nitrogen-containing ring; and acid-addition salts and methyl or ethyl halide quaternary ammonium salts thereof; (2) methyl or ethyl halide quaternary ammonium salts of an o -aminoalkylphenothiazine-10-carboxylate of formula <FORM:0730213/IV (b)/2> wherein R1, R2 and R3 have the same significance as before. The compounds (1) are prepared by reacting a phenothiazine-10-carboxylic acid halide (e.g. the chloride or bromide) with an R2, R3 - aminoalkylamine or an R2, R3 aminoalkylmercaptan, preferably in an inert solvent (e.g. benzene) and acid-addition salts may be prepared directly from the reaction mixture by acidifying with a dilute acid, e.g. hydrochloric, hydrobromic, phosphoric, sulphuric, fumaric, maleic, tartaric, succinic and citric acid. Methyl or ethyl halide quaternary ammonium salts (1) and (2) are prepared by treating the substituted o -aminoalkyl-phenothiazine - 10 - carboxamide, - thiocarboxylate, or -carboxylate in a dry solvent (e.g. ether) with an excess of methyl or ethyl halide and recrystallizing from ethanol. The examples describe the preparation of b -diethylaminoethyl phenothiazine - 10 - carboxylate methiodide and ethobromide, N - (b - diethylaminoethyl)-N - methyl - phenothiazine - 10 - carboxamide and the hydrochlorides of N-(b -diethylaminoethyl) - phenothiazine - 10 - carboxamide, N-(b - dimethylaminoethyl) - phenothiazine - 10-carboxamide and b -diethylaminoethyl phenothiazine - 10 - thiocarboxylate. Reference is also made to compounds in which R2 and R3 are each butyl groups or together with the amine nitrogen form a morpholino or piperidino group and to compounds in which R1 is a butylene group. Reference has been directed by the Comptroller to Specification 708,896.