GB853799A - Diquaternary compounds and process of preparing same - Google Patents

Abstract

The invention comprises compounds of the general formula: <FORM:0853799/IV(b)/1> wherein Alk is an alkylene group containing 2-5 carbon atoms in the straight chain between the N atom, R1 and R2 are C1-3 alkyl groups or, together with the adjacent nitrogen atom, a heterocyclic ring, R3, R4 and R5 are C1-3 alkyl groups, X is a substituted or unsubstituted benzyl, 1-naphthylmethyl, 1-indanyl or 9-fluorenyl group the said substitutents being in the ring once being one or more halogen atoms. C1-4 alkyl and C1-4 alkoxy groups, or when X is benzyl or 1-naphthymethyl, additionally on the a -carbon atom, and being a C1-4 alkyl group of a substituted or unsubstituted phenyl group wherein the substitutents are the same as those on the phenyl a naphthyl nuceli of the benzyl a 1-naphthyemethyl groups respectively, and A is a pharmacologically acceptable anion, and the preparation thereof by reacting diamines of the general formula: <FORM:0853799/IV(b)/2> wherein R6, R7 and R8 are the same as R1, R2 and R4 except they may additionally be hydrogen atoms. Diamines of formula (II) are prepared by reductive condensation of an diamine and an appropriate (aromatic) aldehyde or ketone; condensation of a diamine with an acid chloride followed by reduction of the amide; or reductive condensation of a primary amine and an aromatic aldehyde or ketone followed by condensation with a dialkyl-amino substituted alkyl halide. An additional alkyl group is introduced by reacting the amine with a carbonyl group in the presence of a reducing agent, for example, formic acid.ALSO:Pharmaceutical compositions comprise as active ingredient compounds of the general formula: <FORM:0853799/VI/1> wherein Alk is an alkylene group containing 2-5C in the straight chain between the N-atoms, R1 and R2 are C1-3 alkyl groups or, together with the adjacent N atom a heterocylic ring, R3, R4 and R5 are C1-3 alkyl groups X is a substituted or unsubstituted benzyl, 1-naphthylmethyl, 1-indanyl, or 9-fluorenyl group, the said substituents being in the ring and being one or more halogen atoms C1-4 alkyl or alkoxy groups, or when X is a benzyl or 1-naphthyl methyl group additionally on the a -carbon atom, and being a C1-4 alkyl group or a phenyl group, optionally substituted as in the benzyl a naphthylmethyl groups above and A is a pharmacologically acceptable organic or inorganic anion, together with a pharmaceutically acceptable carrier. Compositions include tablets, capsules, troches, lozenges or solutions the last named both for oral and parenteral administration.