Quinolone derivative or salt thereof and antibacterial containin

Details Quinolone derivative or salt thereof and antibacterial containin Quinolone derivative or salt thereof and antibacterial containin

1993-08-19

1995-05-02

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546123, C07D47104, C07D47102, A61K 31435, A61K 3141

Patent

active

054120985

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP 92/01712, filed Dec. 25, 1992.


TECHNICAL FIELD

The present invention relates to novel quinolone derivatives and salts thereof having excellent antibacterial activity and oral-route absorption, and antibacterial agents containing the compounds.


BACKGROUND ART

Among the compounds which have pyridonecarboxylic acid as a basic skeleton, many are known to be useful as synthetic antibacterial agents due to their excellent antibacterial activities and a broad antibacterial spectrum. Mention may be given to norfloxacin (Japanese Patent Application Kokai No. 141286/1978), enoxacin (Japanese Patent Application Kokai No. 31042/1980), ofloxacin (Japanese Patent Application Kokai No. 46986/1982), cyprofloxacin (Japanese Patent Application Kokai No. 76667/1983) and the like, which have widely found a clinical utility as therapeutic agents for infectious diseases.
These compounds, however, are not sufficiently satisfactory in terms of antibacterial activities, intestinal tract absorption, metabolic stability, minimized adverse side effects, and the like, and hence novel compounds which meet these requirements have been desired.
Under the above circumstances, the present inventors have conducted careful studies with a view toward obtaining clinically excellent synthetic antibacterial agents, and have found that the compounds represented by formula (1) described hereinafter provide excellent oral absorption, exhibit excellent antibacterial activities against gram negative and gram positive bacteria and thus are very useful as synthetic antibacterial agents, leading to the completion of the invention.


DISCLOSURE OF THE INVENTION

The present invention is to provide quinolone derivatives represented by the below-described formula (1), salts thereof and antibacterial agents containing the derivatives or salts: ##STR2## wherein R.sup.1 represents a hydrogen atom, halogen atom or a carboxyl protective group, R.sup.2 represents a hydrogen atom, halogen atom or a lower alkyl group, X represents a hydrogen atom or a halogen atom, Y represents a halogen atom, a cyclic amino group which may have a substituent, a cyclo- lower alkenyl group which may have a substituent, or a group R.sup.3 --(CH.sub.2).sub.m --A--(wherein R.sup.3 represents a hydrogen atom or an amino group which may have a substituent, A represents an oxygen atom or a sulfur atom and m represents a number of 0 to 3), Z represents a nitrogen atom or a group C--R.sup.4 (wherein R.sup.4 represents a hydrogen atom or a halogen atom), W represents a five-membered heterocyclic group which may have a substituent and which has 3 or more hetero-atoms, among which at least 2 hetero-atoms are nitrogen atoms, and n represents a number of 0 to 2.
Since the present compounds (1) exhibit excellent antibacterial activities and are highly safe, they are useful as pharmaceuticals for the human and animals, medicines for fishes, pesticides, preservatives for foods, and the like.


BEST MODE FOR CARRYING OUT THE INVENTION

In the present invention, the term "lower" used in the expressions of the substituents of the quinolone derivatives or their salts (1) means that the group referred to has 1-7, preferably 1-5 carbon atoms when the substituents are linear or branched, and has 3-7 carbon atoms when the substituents are cyclic.
The carboxy protective group represented by R.sup.1 is the ester residue of a carboxylic acid ester, and encompasses any groups which are relatively easily cleaved and produce corresponding free carboxyl groups. Examples of the carboxy protective group include those removable upon treatment under mild conditions such as hydrolysis or catalytic reduction, such as lower alkyl groups (e.g., methyl, ethyl, n-propyl, t-butyl, etc.), lower alkenyl groups (e.g., allyl, etc.), aralkyl groups (e.g., benzyl, etc.) or aryl groups (e.g., phenyl, etc.); and those readily removable in a living body, such as lower alkanoyloxy-lower alkyl groups (e.g., acetoxymethyl, pivaloyloxymethyl, etc.), lower alkoxycarbonyloxy-lower alkyl groups (e

REFERENCES:
patent: 4617308 (1986-10-01), Mich et al.
patent: 5137892 (1992-08-01), Chu et al.
patent: 5153203 (1992-10-01), Yatsunami et al.
patent: 5245037 (1993-09-01), Kuramoto et al.

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