Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-02-07
1995-12-26
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546156, C07D215233, C07D21538, A61K 31475
Patent
active
054788412
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR 93/00505, filed 25 May 1995.
A subject of the present invention is new quinolones and more particularly quinolones substituted by a piperidine ring.
More particularly a subject of the invention is new piperidinyl quinolone 3-carboxylic acids endowed with useful antibacterial properties.
Specifically a subject of the invention is new 6-fluoro-7-piperidine-quinolone-3-carboxylic acids of general formula I: ##STR2## in which R is hydrogen or fluorine radical, an acyl radical derived from an organic carboxylic acid, an alkyl carbonic acid or an aryl sulphonic acid or an arylamino carbonyl radical of form: ##STR3## in which Ar represents a mono- or bicyclic aromatic radical optionally substituted by one, two or three substituents chosen from lower alkyls, halogens and trifluoromethyl tertbutyl radical, a cyclopropyl radical, a (cyclopropyl) alkyl radical, a phenyl radical or a phenyl radical substituted by one, two or three substituents defined previously equal to 0 or 1.
Among the compounds of the invention five sub-groups are distinguished: ##STR4## in which R.sub.1 represents hydrogen, a linear or branched lower alkyl radical optionally substituted by a hydroxyl or an acyl radical defined as above ##STR5## in which R.sub.1 represents hydrogen, a linear or branched lower alkyl radical optionally substituted by a hydroxyl or an acyl radical derived from a carboxylic, carbonic or arylsulphonic acid ##STR6## in which R.sub.3 represents an isopropyl radical previously ##STR7## in which R.sub.3 represents a phenyl radical optionally substituted by one, two or three substituents previously ##STR8## in which R.sub.3 represents a (cyclopropyl) alkyl radical in which the alkyl remainder a has 1 to 3 carbon atoms previously.
Among the compounds of general formula (I), the compounds in which ZR.sub.1 is an ureido function are those which are currently preferred.
Particular emphasis is also given to the ureidic compounds of formula I.sub.F : ##STR9## in which R and R.sub.3 have the meanings provided previously halogen
Among the compounds of general formula I, the compounds in which ZR.sub.1 is an ureido function are those which are currently preferred.
The compounds according to the invention can be salified by the addition of a mineral or organic base. The main salts which can be used are those of alkali metals, alkaline-earth metals, ammonium, iron, aluminium, alkylamine salts, hydroxylalkylamine salts, phenylalkylamine salts, pyridylalkylamine salts, cyclanylamine salts, dicyclanylalkylamine salts . . .
Among the salts, sodium, lithium, ammonium, N-methylglucamine and tromethanol salts are those which are currently preferred.
These compounds can also be salified by a strong mineral or organic acid when R.sub.1 represents hydrogen, a lower alkyl radical or a lower (hydroxyalkyl) radical. Among these, the hydrochlorides, methanesulphonates, lactates or acetates are preferred examples.
Among the compounds of general formula I, there can be mentioned quite particularly: 1-cyclopropyl-7-((4-aminomethyl)-1-piperidinyl)-quinolone-3-carboxylic acid and its addition salts with a mineral or organic acid ylic acid and its addition salts with a mineral or organic acid.
The compounds according to the invention possess remarkable antibacterial properties, in particular against Gram positive bacteria.
Moreover, they possess the property of being moderately resorbed by general route in such a way that their elimination is essentially faecal.
Therefore they can be used effectively as medicaments for bacterial infections of the alimentary canal, for the treatment of bacterial dysenteries, of traveller's diarrhoea or of intestinal infections. They can also be used by topical route for the treatment of ocular infections or infections of the acoustic duct.
To this end, the compounds according to the invention will be used in the form of pharmaceutical compositions in which the active ingredient of general formula I or one of its salts, is added to or mixed with a pharmaceutically acceptable, non-toxic,
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Bouchara S.A.
Dentz Bernard
M. Mach D. Margaret
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