GB999237A - Quinoline derivatives - Google Patents

Abstract

The invention comprises compounds of the formulae <FORM:0999237/C2/1> wherein A represents a divalent straight or branched chain aliphatic hydrocarbon group containing 2 to 6 carbon atoms, R and R1 represent, the same or different, a hydrogen atom or an alkyl group containing up to 4 carbon atoms and B represents a single bond or a group -A1-NH-, in which A1 has the same significance as A and is attached to the nitrogen atom of the ethylenediamine group, and non-toxic acid addition salts thereof and the preparation thereof by reacting a 7-chloroquinoline of the formula <FORM:0999237/C2/2> with a compound of the formula <FORM:0999237/C2/3> where (a) Y represent a halogen atom or phenoxy group, one of V and W represents a group -ANH-, the group A being attached to a nitrogen atom of the ethylenediamine group, and the other represents the symbol B in the formula I; (b) Y represents the group <FORM:0999237/C2/4> , wherein X represents the acid residue of a reactive ester, Z represents a hydrogen atom, an alkanoyl group of up to 4 carbon atoms or a benzoyl group, V represents a single bond and W represents B1, i e a single bond or the group -A1-NZ-; and, if necessary, removing from the resultant product the group Z The compounds are also prepared by reacting two molecules of a 7-chloroquinoline of the formula II wherein Y represents a halogen atom or phenoxy group with one molecule of a compound of the formula <FORM:0999237/C2/5> and where B represents a group identical with that represented by -HN-A-, by reacting two molecules of a 7-chloroquinoline of the formula <FORM:0999237/C2/6> with one molecule of a compound of the formula <FORM:0999237/C2/7> Compounds of the formula III may be made by condensing equimolecular proportions of a compound of the formula II and a compound of the formula IV <FORM:0999237/C2/8> wherein Y, V and W have the significance set out under the heading (a) above. Where V represents a single bond and W represents the group -A-NZ-, compounds of the formula III may be made by condensing equimolecular proportions of compounds of the formulae V and VI. 1,10 - Diamino - 4,7 - diazadecane is prepared by catalytic reduction of 1,8-dicyano-3,6-diazooctane which is made by condensation of acrylonitrile with ethylene diamine. N - Ethyl - N,N - bis(2 - aminoethyl)amine is made by dephthalimidation of N-ethyl-N,N-bis (2-phthalimido-ethyl)amine which is made by the condensation of N-ethyl-N,N-bis(2-chloroethyl) amine with potassium phthalimide. Pharmaceutical compositions for oral, rectal and parenteral administration, which have antimalarial, amoebicidic and anthelmintic properties and which may take the form of tablets, pills, dispersible powders, granules, emulsions, solutions, suspensions, syrups and elixirs comprise compounds of the general formula I and addition salts thereof.