Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-01-26
1995-07-04
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514213, 540492, 540575, 540597, A61K 3155, A61K 31505, C07D24308, C07D24300
Patent
active
054300282
DESCRIPTION:
BRIEF SUMMARY
This application is a Rule 37 CFR 1.371 of PCT/JP93/00694 filed May 25, 1993.
TECHNICAL FIELD
The present invention relates to a novel 5-aminoquinolone carboxylic acid derivative or a salt thereof, which has an excellent antibacterial activity against Gram-negative bacteria including tolerant bacteria, and Gram-positive bacteria, and an antibacterial agent containing such a derivative or salt as an active ingredient.
BACKGROUND ART
Synthetic antibacterial agents such as nalidixic acid and piromidic acid have heretofore been known as therapeutic agents for infective diseases. However, these agents have involved a drawback that they exhibit insufficient effect on intractable diseases such as pyocyanic infection.
Meanwhile, quinolone carboxylic acid derivatives substituted with a fluorine atom at 6 position, such as norfloxacin, ofloxacin, cyprofloxacin and sparfloxacin have been developed and widely used clinically because of their strong antibacterial activities against Gram-negative bacteria.
However, the conventional synthetic antibacterial agents have involved drawbacks in low bioavailability because of their poor absorptivity in a living body, and in low antibacterial activity against Gram-positive bacteria, in particular, tolerant bacteria such as methicillin-resistant Staphylococcus aureus.
Therefore, it is an object of the present invention to provide an antibacterial agent which has strong antibacterial activities against both Gram-negative bacteria and Gram-positive bacteria including tolerant bacteria, and also has superior absorptivity.
In view of the foregoing circumstances, the present inventor has synthesized a great number of quinolone derivatives to investigate their antibacterial activities and absorptivity into the living body. As a result, it has been found that 5-aminoquinolone carboxylic acid derivatives represented by the general formula (1), which will be described subsequently, and salts thereof exhibit extremely enhanced antibacterial activities against Gram-positive bacteria, in particular, tolerant bacteria thereof compared with that of the conventional quinolone carboxylic acid derivatives while retaining good antibacterial activities against Gram-negative bacteria, and also have excellent absorptivity, leading to completion of the present invention.
DISCLOSURE OF THE INVENTION
The present invention is directed to a 5-aminoquinolone carboxylic acid derivative represented by the following general formula (1): ##STR2## wherein R.sup.1 means a hydrogen atom, an amino group, a linear or branched alkyl group having 1-5 carbon atoms and an alkylamino group containing a linear or branched alkyl group having 1-5 carbon atoms, R.sup.2 denotes a hydrogen atom or a linear or branched alkyl group having 1-5 carbon atoms, X stands for a halogen atom, Y means CH.sub.2, NH, CHR.sup.3 NR.sup.3 (R.sup.3 denoting a linear or branched alkyl group having 1-5 carbon atoms) or an oxygen atom, and Z stands for an oxygen atom or two hydrogen atoms, or a salt thereof, and an antibacterial agent containing such a derivative or salt as an active ingredient.
BEST MODE FOR CARRYING OUT THE INVENTION
The 5-aminoquinolone carboxylic acid derivative according to the present invention is represented by the general formula (1). In the formula, examples of the linear or branched alkyl group having 1-5 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and n-pentyl.
Examples of the salt of the compound (1) according to the present invention include alkali metal salts, inorganic acid salts and organic acid salts. More specifically, the alkali metal salts include lithium, sodium and potassium salts, and the like. The inorganic acid salts include hydrochlorides, sulfates, nitrates, hydrobromides, phosphates and the like. The organic acid salts include acetates, fumarates, maleates, lactates, succinates, citrates, malates, oxalates, methanesulfonates, benzenesulfonates, p-toluenesulfonates and the like.
The compound (1) of the present invention can be prepared by reacting
REFERENCES:
patent: 4795751 (1989-01-01), Matsumoto et al.
patent: 4894458 (1990-01-01), Masuzawa et al.
Asaoka Takemitsu
Kaihoh Terumitsu
Konno Fujiko
Kuraishi Tadayuki
Matsuda Hideaki
Grumbling Matthew V.
Shah Mukund J.
SS Pharmaceutical Co., Ltd.
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