Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1992-12-08
1995-05-30
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546156, A61K 3147, C07D21556
Patent
active
054201403
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR92/00319 filed Apr. 10, 1992.
This invention relates to the field of medicinal chemistry and more particularly to that of difluorinated quinolones.
More particularly it has as a subject matter difluoroquinolones which are substituted in position 7 with a piperidine ring.
Specifically it has as a subject matter the 7-(piperidinyl-1) 6,8-difluoro 4-oxo 1,4-dihydroquinoline 3-carboxylic acids of the general formula I ##STR4## wherein R represents a hydrogen, a lower alkyl radical, a lower (hydroxy alkyl) radical, the acyl moiety of an organic carboxylic acid having from 1 to 10 carbon atoms or a carboxamido grouping of formula ##STR5## wherein Y is a lower alkyl radical, a lower alkenyl radical, a phenyl, or a substituted phenyl radical, a phenyl radical or a substituted phenyl radical of the formula ##STR6## wherein Z represents a halogen atom and p is equal to 1, 2 or 3.
Among the compounds of general formula I, it may more particularly cited: I.sub.A ##STR7## wherein R has the above-given definitions. the compounds for which R.sub.1 is a fluoromethyl radical, having the formula I.sub.B ##STR8## wherein R has the above-given definitions. the compounds for which R.sub.1 is a vinyl radical, having the formula I.sub.C ##STR9## wherein R has the above-given definitions. and having the formula I.sub.D ##STR10## wherein R is defined as previously X represents hydrogen or a halogen atom
This invention also relates to the salts of the compounds of general formula I with a mineral or organic base. In fact the compounds of general formula I are very slightly soluble in water or in the aqueous medium such as the biological media. It appears thus wanted to increase their capacity to be dissolved and hence to their diffusion.
This invention also relates to the salts of the compounds of general formula I for which R is a hydrogen or a lower alkyl radical or a lower hydroxy alkyl radical with a mineral or organic acid, preferably a therapeutically-compatible acid.
Moreover the [4-aminomethyl piperidino] derivatives of general formula I show an asymetric carbon atom ##STR11## and may therefore be resolved into their optical isomers.
Among these salts of the compounds of general formula I with a mineral or organic base, it may more precisely cited the alkali metal salts, the earth-alkaline metal salts, the salts of iron, the salts of Aluminium, the salts of Magnesium and of the other non-toxic metals they may also be cited the alkylamine salts having from 1 to 6 carbon atoms, the salts of a hydroxyalkylamine, the salts of a cycloalkylamine, the salts of a (dicycloalkyl) amine, the salts of a di(cycloalkyl) alkylamine, the osamine salts, the basic amino acids salts, the quaternary ammonium salts, the phenyl alkylamine salts, the (heteroaryl) alkylamine salts, and the heteroarylamine salts.
Among these salts one prefers the alkali metal salts such as the sodium, the lithium or the ammonium salts, the alkylamine salts such as the methylamine salt, the ethylamine salt or the isopropylamine salt; the hydroxyalkylamine salts such as the amino ethanol or di(amino ethanol) salts or the tromethanol salts, the osamine salts such as the N-methyl glucamine salts, the basic amino acid salts such as the lysine salts, the arginine salts or the sarcosine salts as well as the quaternary ammonium salts such as choline or carnitine.
Among the addition salts with a mineral or organic acids, it may more particularly be cited the halohydrates such as the hydrochlorides, the hydrobromides, or the hydroiodides; the sulphates, the nitrates, the phosphates, the hypophosphites, or the metaphosphates; the salts of a carboxylic acid such as the acetates, the propionates, the lactates, the gluconates the benzoates, the salicylates, the gentisates, the thiophene carboxylates, or the indolyl acetates; the addition salts with a sulphonic acid such as a methane sulfonate, a trifluoromethane sulfonate, an ethane sulfonate, an isethionate, a camphosulphonate, a benzene sulphonate or a p.toluene sulphonate; the addition salts
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Bouchara S.A.
Dentz Bernard
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