GB901643A - Phenanthridinium salts and their preparation - Google Patents

Abstract

The invention comprises: (a) amidinophenyldiazoaminophenanthridinium salts of the general formula <FORM:0901643/IV (b)/1> (wherein Am represents -C(:NH)NH2, R1 a C1-6 alkyl group, R2 an aryl group, R3 a C1-6 alkoxy group or a halogen atom and Y a pharmaceutically acceptable anion) and their acid addition salts (including insoluble salts, e.g. amsonates, embonates and suramin salts); (b) the preparation of compounds I, in admixture with isomeric azo dyestuffs (see Group IV(c)) from which they may or may not be separated, by diazotizing a compound of the general formula <FORM:0901643/IV (b)/2> and coupling the resulting diazonium salt with an equimolecular proportion of a phenanthridinium salt of the general formula <FORM:0901643/IV (b)/3> and (c) pharmaceutical compositions comprising at least one compound I, with or without the isomeric azo dyestuff, in association with a significant amount of a pharmaceutical carrier. Compounds I can also be prepared by diazotizing a compound III and coupling the resulting diazonium salt with a compound II. The pharmaceutical compositions, which are active against blood parasites, e.g. trypano somes, may be in forms suitable for parenteral or oral administration, e.g. solutions, suspensions, emulsions, tablets, pills, dispersible powders, granules, syrups, elixirs and capsules. 4 - Amino-3-bromobenzamidine monohydrochloride, 3-amino - 4 - chlorobenzamidine dihydrochloride and 3-amino-4-methoxybenzamidine dihydrochloride are prepared from the correspondingly substituted benzonitriles. 3-Amino-4-chlorobenzonitrile is prepared by reducing 4-chloro-3-nitrobenzonitrile.ALSO:Azo dyestuffs of the general formula <FORM:0901643/IV (b)/1> (wherein R1 represents a C1-6 alkyl group, R2 represents an aryl group, Y represents an anion, one Z represents the group <FORM:0901643/IV (b)/2> and the others hydrogen atoms, Am represents -C(:NH)NH2 and R3 represents a C1-6 alkoxy group or a halogen atom) are obtained as by-products in the preparation of diazoamino compounds (see Group IV(b)) by diazotizing a compound of the general formula <FORM:0901643/IV (b)/3> and coupling the resulting diazonium salt with an equimolecular proportion of a phenanthridinium salt of the general formula <FORM:0901643/IV (b)/4> The two products may be separated by, for example, fractional crystallization from methanol.