GB714070A - New phenanthridine compounds - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0714070/IV (b)/1> (wherein R represents an alkyl or alkenyl radical containing at least 2 carbon atoms, X represents an anion and Y represents NH2 or NO2), and the manufacture thereof by quaternating a phenanthridine of the formula <FORM:0714070/IV (b)/2> (wherein R1, R2 and R3 represent groups convertible into NH2), and subsequently converting R1 and R2 into NH2 groups, and similarly converting R3 except when it is NO2 and a final product in which Y is NO2 is desired. Advantageousl R1 and R2 are carbalkoxyamino groups which are converted to NH2 by acid hydrolysis after the quaternization, and R3 is NO2 which is subsequently reduced to NH2 if desired. The products are useful therapeutically as trypanocides. In examples: (1) 2 : 7 - dicarbethoxyamino - 9 - p - nitrophenylphenanthridine is heated with allyl iodide in nitrobenzene, the product is treated with silver methanesulphonate in aqueous alcohol, the resulting methanesulphonate is heated with a 2 : 1 mixture of concentrated sulphuric acid and water, and the hydrolysis mixture diluted with aqueous alcohol, neutralized with ammonia solution and treated with ammonium chloride to produce 2 : 7-diamino - 9 - p - nitrophenyl - 10 - allylphenanthridinium chloride; (2) the product of (1) is reduced with ferrous sulphate in the presence of an aqueous suspension of barium hydroxide; (3) the starting material of (1) is heated with propyl toluene-p-sulphorate in nitrobenzene, the product is hydrolysed as in (1), and the hydrolysis mixture poured into ice water, neutralized and treated with ammonium chloride to give 2 : 7-diamino-9-p-nitrophenyl-10-propylphenanthridinium chloride; (4) the product of (3) is reduced as in (2); (5) the quaternating agent in (3) is replaced by diethyl sulphate; (6) the product of (5) is reduced as in (2). Specifications 635,152 and 679,128 are referred to.