GB724217A - Improvements in or relating to derivatives of phenthiazine - Google Patents

Abstract

The invention comprises phenthiazine derivatives of the formula <FORM:0724217/IV (b)/1> in which the phenthiazine ring is substituted in the 1- or 3-position (Beilstein nomenclature) by an alkyl group (with not more than 6 and preferably not more than 4 carbon atoms) and in which the grouping -A-NR1R2 either a dimethylaminopropyl or a pyrrolidinopropyl chain, and their salts. It also comprises phenthiazine derivatives of the above formula in which the phenthiazine ring is substituted by an alkoxy group, together with their salts obtainable by the conversion of m-alkoxy-substituted diphenylamines by the application of known methods for the conversion of a diphenylamine into an N-(tertiaryaminoalkyl)-phenthiazine. These compounds may be obtained from the appropriately substituted phenthiazine and a dimethylaminopropyl halide or a pyrrolidinopropyl halide. The 1- and 3-substituted phenthiazines are obtained, as a mixture from a m-alkyl or -alkoxy diphenylamine by known methods, e.g. heating with sulphur. The mixture is not necessarily separated before reaction with the tertiary aminoalkyl halide since a mixed product may be used therapeutically as a "potentiator" for anaesthetics and analgesics. Reaction may be effected in presence of an acid binding agent in a solvent, or without an acid-binding agent by adding a solution of tertiary-amino-alkyl halide to the molten phenthiazine compound. As an alternative dimethylamine or pyrrolidine may be reacted with an N-halogenopropylphenthiazine with the appropriate 1- or 3-substituent. In example (1) 10-(31-dimethylamino-11-propyl)-3-methyl-phenthiazine is prepared by reacting 3-methyl-phenthiazine with 3-dimethylamino-1-chloropropane in the presence of sodamide. Similarly prepared are (2) 10-(31-dimethylamino - 11 - propyl) - methoxy - phenthiazine and its oxalate and iodomethylate; (3) 10-(31-pyrrolidino - 11 - propyl) - 3 - methyl - phenthiazine and its oxalate; (4) 10-(31-pyrrolidino-11-propyl) - methoxy - phenthiazine; (5) 10 - (21 - dimethylamino - 11 - propyl) - methoxy - phenthiazine; (6) 10 - (31 - dimethylamino - 11 - propyl) - ethoxy - phenthiazine and its oxalate; (7) 31 - dimethylamino - 11 - propyl) - butoxy - phenthiazine and its oxalate. The alkoxy - derivatives are produced from starting materials obtained by reacting a m-alkoxy-diphenylamine with sulphur, and hence the products have the alkoxy group in the 1- or 3-position or are mixtures of the 1- and 3-alkoxy compounds. Specifications 608,208, 632,277 and 714,218 are referred to.