GB716206A - Improvements in or relating to new phenthiazine derivatives - Google Patents

Abstract

The invention comprises phenthiazine compounds of the formula <FORM:0716206/IV (b)/1> in which R is hydrogen, chlorine, bromine, methyl or methoxy in the 6- or 8- position, X is 1- or 3-Cl or Br, A is a divalent straight or branched chain of 2-5 C, and R1 and R2 are methyl, ethyl, or jointly the residue of a heterocyclic ring, with the exception of those compounds of the above type claimed in Specifications 716,207, 716,227 and 716,230. The products are obtainable as hydrochlorides or other salts by the action of a tertiary aminoalkyl halide corresponding to the residue A-N< above on a phenothiazine unsubstituted in the 10-position or by the action of a secondary amine on a 10-haloalkyl phenthiazine, followed by conversion into other salts, if desired. In examples, chlorophenthiazine, bromophenthiazine, obtainable as isomeric mixtures of the 1- and 3-substituted compounds by cyclization of a m-halo-diphenylamine with sulphur, are treated with 1-dimethylamino-2-chloropropane, 1-dimethylamino - 2 - chloroethane, 1 - diethylamino - 2 - chloroethane, 1 - diethylamino - 2 - chloropropane, 3 - dimethylamino - 2 : 2 - dimethyl - 1 - chloropropane, 3 - dimethylamino - 1 - chloropropane, 3 - dimethylamino - 3 - methyl - 1 - chlorobutane, 2 - dimethylamino -1-chlorobutane, and other alkyl halides, and b -chloroethyl - N - morpholine to give the corresponding 10-dialkylamino- or heterocyclicalkyl-phenthiazines. Similar products are described from phenthiazines substituted by halogen and methyl, and halogens (examples 14 and 15), and halogen and methoxy (example 18); 10-(51-chloro-11-pentyl) chlorophenthiazine and other haloalkylphenthiazines are treated with dimethylamine to give the corresponding dimethylaminoalkylphenthiazines. Mixtures of straight and branched chain isomeric products are sometimes obtained when a tertiary aminoalkyl halide having halogen and nitrogen on adjacent C atoms is combined with the phenthiazine compound. Dichlorphenthiazine is obtained by condensing sulphur and 3 : 31-dichlorodiphenylamine in presence of iodine. Chlormethoxyphenthiazine is obtained by condensing sulphur and 3-chloro-31-methoxy-diphenylamine.