Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-07-08
1999-06-08
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514300, 514312, 544362, 544363, 546123, 546156, A61K 31495, A61K 3147, C07D40102, C07D40104
Patent
active
059104988
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to a novel pyridonecarboxylic acid derivative or salt thereof having improved antibacterial action and peroral absorption and an antibacterial agent comprising the same.
BACKGROUND ART
Among compounds having pyridonecarboxylic acid as a basic skeleton, many are known to be useful as synthetic antibacterial agents because they have superior antibacterial action and a broad antibacterial spectrum. Inter alia, norfloxacin (JP-A 141286/1978), enoxacin (JP-A 31042/1980), ofloxacin (JP-A 46986/1982), ciprofloxacin (JP-A 76667/1983), tosufloxacin (JP-A 228479/1985), etc. are widely used in clinical treatment as an infectious disease remedy.
These compounds, however, are still unsatisfactory in antibacterial activity, enteral absorption, metabolic stability and side effect, especially phototoxicity and cytotoxicity.
DISCLOSURE OF THE INVENTION
The present invention has been made under the above-mentioned circumferences and its object is to provide novel pyridonecarboxylic acid derivatives or salts thereof which are satisfactory in antibacterial action, enteral absorption, metabolic stability and side effects, especially phototoxicity and cytotoxicity, and an antibacterial agent comprising the same.
In view of the foregoing circumstances, the present inventors have carried out on extensive investigation with a view toward obtaining clinically improved synthetic antibacterial agents. As a result, it has been found that compounds represented by the formula (1) described below exhibit excellent antibacterial activities against gram negative and gram positive bacteria, are very low toxic, and are quite useful as synthetic antibacterial agents, leading to the completion of the invention.
More specifically, the present invention provides a pyridonecarboxylic acid derivative represented by the following general formula (1): ##STR2## wherein R.sup.1 is a hydrogen atom or carboxy protecting group, R.sup.2 is a nitro or substituted or unsubstituted amino group, R.sup.3 is a halogen atom, each of R.sup.4 and R.sup.5, which may be the same or different, is a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group, R.sup.6 is a hydrogen atom, halogen atom, hydroxy group, lower alkyl group or amino group, R.sup.7 is a hydrogen atom or halogen atom, A is a nitrogen atom or --CX.dbd. wherein X is a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group, and Z is a halogen atom or a saturated cyclic amino group which may have a substituent, or a salt thereof.
The present invention also provides an antibacterial agent comprising the pyridonecarboxylic acid derivative or salt thereof as an active ingredient.
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention is described below in detail. In conjunction with the substituents in the pyridonecarboxylic acid derivative of general formula (1) according to the invention, the term "lower" means that the substituents have 1 to 7 carbon atoms, especially 1 to 5 carbon atoms when they have a chain structure and 3 to 7 carbon atoms when they are cyclic.
In general formula (1), the carboxy protecting group represented by R.sup.1 is an ester residue of a carboxylic ester, for example, ester residues which are relatively easily cleaved to liberate a corresponding free carboxyl group. Exemplary groups are those groups which are eliminated by such treatment under moderate conditions as hydrolysis and catalytic reduction, for example, lower alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, pentyl group, hexyl group, and heptyl group; lower alkenyl groups such as vinyl group, allyl group, 1-propenyl group, butenyl group, pentenyl group, hexenyl group, and heptenyl group; aralkyl groups having 7 to 11 carbon atoms such as benzyl group; and aryl groups having 6 to 14 carbon atoms such as phenyl group and naphthyl group, or those groups which are readily eliminated in a living body, for example, lower alkanoyloxy lower alkyl groups such
REFERENCES:
patent: 4146719 (1979-03-01), Irikura
Amano Hirotaka
Hayashi Norihiro
Hirao Yuzo
Kuramoto Yasuhiro
Niino Yoshiko
Dentz Bernard
Wakunaga Seiyaku Kabushiki Kaisha
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