Pyridonecarboxylic acid derivatives or their salts and antibacte

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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Details

514300, 546123, 546156, A61K 31435, A61K 3147, C07D47102, C07D21516

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active

059984368

DESCRIPTION:

BRIEF SUMMARY
This application claims the benefit under 35 U.S.C. .sctn.371 of prior PCT International Application No. PCT/JP96/02710, which has an International filing date of Sep. 20, 1996, which designated the United States of America, the entire contents of which are hereby incorporated by references.


TECHNICAL FIELD

The present invention relates to novel pyridonecarboxylic acid derivatives or salts thereof having excellent antibacterial properties and oral absorption, and antibacterial agents containing the same.


BACKGROUND ART

Many compounds having basic skeleton of pyridonecarboxylic acid are known to be useful synthetic antibacterials for their excellent antibacterial properties and wide antibacterial spectrum. Among such compounds, norfloxacin (Japanese Patent Application Laid-Open No. 53-141286), enoxacin (Japanese Patent Application Laid-Open No. 55-31042), ofloxacin (Japanese Patent Application Laid-Open No. 57-46986), ciprofloxacin (Japanese Patent Application Laid-Open No. 58-76667), tosufloxacin (Japanese Patent Application Laid-Open No. 60-228479), and the like are widely used in clinical practice for treating infections.
These compounds, however, need further improvements in antibacterial activities, intestinal absorption, metabolic stability, and side effects, and in particular, in phototoxicity, cytotoxicity.
Accordingly, an object of the present invention is to provide novel compounds which are sufficient in such aspects.


DISCLOSURE OF THE INVENTION

In view of such situation, the inventors of the present invention have made an intensive study to find compounds which would be excellent synthetic antibacterial agents in clinical practice, and found that novel compounds represented by the following general formula (1) has good antibacterial properties to gram negative and positive bacteria as well as an extremely low toxicity, and therefore, would be a very useful synthetic antibacterial. The present invention has been accomplished on the bases of such a finding. ##STR2## [In the formula, R.sup.1 represents hydrogen atom or a carboxyl protective group; R.sup.2 represents hydroxyl group, a lower alkoxy group, or a substituted or unsubstituted amino group; R.sup.3 represents hydrogen atom or a halogen atom; R.sup.4 represents hydrogen atom or a halogen atom; R.sup.5 represents a halogen atom or an optionally substituted saturated cyclic amino group; R.sup.6 represents hydrogen atom, a halogen atom, nitro group, or an optionally protected amino group; X, Y and Z may be the same or different and respectively represent nitrogen atom, --CH.dbd. or --CR.sup.7 .dbd. (wherein R.sup.7 represents a lower alkyl group, a halogen atom, or cyano group) (with the proviso that at least one of X, Y and Z represents the nitrogen atom), and W represents nitrogen atom or --CR.sup.8 .dbd. (wherein R.sup.8 represents hydrogen atom, a halogen atom, or a lower alkyl group.)]
Accordingly, the present invention provides pyridonecarboxylic acid derivatives represented by the general formula (1), above, or their salts, and antibacterial agents containing the pyridonecarboxylic acid derivatives or their pharmaceutically acceptable salts as their effective components.


BEST MODE FOR CARRYING OUT THE INVENTION

The novel pyridonecarboxylic acid derivatives of the present invention are represented by the general formula (1) as shown above, and the term "lower" used for the substituents of the pyridonecarboxylic acid derivatives represented by the general formula (1) designates that the substituent comprises 1 to 7 carbon atoms, and preferably 1 to 5 carbon atoms in the case of a linear substituent, and that the substituent comprises 3 to 7 carbon atoms in the case of a cyclic substituent.
In the general formula (1), R.sup.1 represents hydrogen atom or a carboxyl-protective group, and the term, carboxyl-protective group herein designates an ester residue of a carboxylate ester, and the carboxyl protective group may be any carboxylate ester residue which cleaves relatively easily to generate the corresponding free carboxyl grou

REFERENCES:
patent: 4994599 (1991-02-01), Chu
patent: 5519016 (1996-05-01), Kimura
patent: 5631256 (1997-05-01), Demuth
patent: 5703231 (1997-12-01), Randall

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