GB578226A - Improvements in or relating to the manufacture of phenanthridine compounds - Google Patents

Abstract

Phenanthridine derivatives, including quaternary salts, having trypanocidal potency, are produced by the cyclisation, using a pentavalent phosphorus compound, of an acylated o-xenylamine carrying one or more nuclearly - substituted carbamic ester radicals, preferably in the form of carbalkoxyamido groups. Ring-closure is effected either by a brief heat-treatment with phosphorus oxychloride alone, or by phosphorus oxychloride in the presence of nitrobenzene or other non-reactive liquid of high boiling-point. The urethanes so obtained readily hydrolyse to yield the free primary amines, e.g. on heating with moderately-concentrated sulphuric acid, and such amines are convertible into aminophenanthridinium salts; moreover, such urethanes may be quaternated and thereafter hydrolysed to form the corresponding amino-phenanthridiuium salts. Phenanthridine derivatives carrying mixed substituents and having the general formula <FORM:0578226/IV/1> wherein X represents an alkyl or aralkyl group and Y represents the anion of an acid, R1 may represent-NH2, -NHCOCH3 or-NH.COOEt and R2 may represent -NO2 or -NH2, are also made available by this process, and a new route is provided through a compound of this general formula, wherein R1=-NH.COOEt and R2=-NO2 to the corresponding diamine (R1=R2=NH2). Numerous examples are given. Specification 372,859 is referred to. Specifications 511,353 and 520,273 also are referred to in the Provisional Specification.