GB889262A - Quinoline compounds - Google Patents

Abstract

The invention comprises quinolines which contain in the 3-position an unsubstituted or substituted guanidino group and which are unsubstituted or C-substituted by a lower alkyl or a lower alkoxy or an alkylene dioxy group, their physiologically tolerable acid addition salts, acyl derivatives and quaternary ammonium salts, pharmaceutical preparations containing these compounds (see Group VI)., and the preparation of the compounds by reacting a 3-aminoquinoline with an S-alkylisothiourea or a cyanamide and, if desired, in a resulting quinolyl-(3)-guanidine whose imino or amino groups are unsubstituted, substituting the latter by hydrocarbon radicals or acyl radicals and/or converting the resulting free compound into a salt or a salt into the free compound. Substituents of the guanido group include alkyl, alkylene (in which instance when the alkylene group is ethylene the guanido group is a 4,5-dihydroimidazoyl-(2)-amino group) and acyl groups. Acyl groups are derived from acids such as lower alkoxy carbonic, carbamic, lower alkanoic, lower alkenoic, lower alkynoic, b -cyclopentylpropionic, monohaloacetic, trifluoracetic, methoxy acetic, dimethylaminoacetic, b -dimethylaminopropionic, b -piperidinopropionic, benzoic, methoxybenzoic, 3,4,5-trimethoxybenzoic, 4-O-ethoxysyringic, 3,4-dichlorobenzoic, 3-nitrobenzoic, 3 dimethylaminobenzoic, nicotinic, isonicotinic, 2-furancarboxylic, 2-thiophenecarboxylic, phenyl- or diphenyl-acetic, b -phenylpropionic, p-methoxyphenylacetic, cinnamic, p-chlorocinnamic, 3,4,5-trimethoxycinnamic, pyridyl-(2)-acetic and thienyl-(2)-acetic acids. Lower alkyl and alkoxy groups contain 1 and 7 carbon atoms.ALSO:Pharmaceutical compositions having anti-hypertensive activity comprise quinolines substituted in the 3 position by guanidino groups and optionally C-substituted by lower alkyl or lower alkoxy groups (i.e. containing 1-7 carbon atoms), their acyl derivatives, acid addition or quaternary ammonium salts and a pharmaceutical carrier. The guanidino groups may be unsubstituted or substituted by alkyl or alkylene groups (in which latter instance the guanidino group is converted into a heterocyclic ring e.g. a - 4 : 5 - dihydro - imidazolyl - (2) - amino group with ethylene). Acyl derivatives are derived from aliphatic, monocyclic aromatic, heterocyclic araliphatic or heterocyclic-aliphatic carboxylic acids, salts from therapeutically useful organic and inorganic acids and quaternary ammonium salts from reactive esters of alkanols or aralkanols. The compositions are in a form suitable for enteral or parenteral administration such as tablets, dragees, capsules, solutions, suspensions or emulsions and may contain other therapeutically useful substances.