GB839784A - Phenothiazine derivatives - Google Patents

Abstract

The invention comprises phenthiazine derivatives of the general formula <FORM:0839784/IV (b)/1> (wherein Ac represents an acyl radical, Y and Z represent hydrogen and/or halogen atoms or C1-4 alkyl groups, A represents oxygen, sulphur or an imido bridge which may be substituted, B represents a bivalent aliphatic radical which may be branched and/or substituted, and R1 and R2 represent alkyl radicals which may be branched, or they may be joined to one another or to a carbon atom of B to form a 5- or 6-membered nitrogen-containing heterocyclic ring, and wherein the substituents represented by Ac, Y and Z may be at any position in either of the homocyclic rings and may be in the same or different rings), and their acid addition and quaternary ammonium salts. These compounds possess spasmolytic and antihistaminic activity. The bases may be prepared from phenthiazines of the general formula <FORM:0839784/IV (b)/2> by: (a) reaction with phosgene to form a 10-carbonyl chloride which is then reacted with an aminoalcohol, aminothioalcohol or diamine; (b) (when A is NH) reaction with an aminoalkyl isocyanate in the presence of an acid or basic catalyst; (c) reaction with an aminoacyl halide of the general formula <FORM:0839784/IV (b)/3> (wherein Hal represents a halogen atom) in the presence of acid-binding or condensing agents; or (d) introduction by similar methods of a group -CO-A-B-E, wherein E represents a group which is convertible into <FORM:0839784/IV (b)/4> and is subsequently so converted. 1 - Methyl - x - propionylphenthiazine is prepared by reacting 1-methyl-10-acetylphenthiazine with propionyl chloride in the presence of aluminium chloride, and splitting off the 10-acetyl group by acid hydrolysis. 3 - Chloro - x - propionylphenthiazine is similarly prepared from 3-chloro-10-propionylphenthiazine.