Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-08-10
2000-02-15
Seaman, D. Margaret
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546156, 548405, A61K 31475, C07D215233, C07D20930
Patent
active
060253703
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a quinolone-carboxylic acid derivative represented by the general formula [1] or its salt: ##STR2## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group; R.sup.2 represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R.sup.3 represents at least one member selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio group, a nitro group, a cyano group, an acyl group, a protected or unprotected hydroxyl group, and a protected or unprotected, or substituted or unsubstituted amino group; R.sup.4 represents at least one member selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or imino group, a protected or unprotected, or substituted or unsubstituted amino group, an alkylidene group, an oxo group and a group forming a cycloalkane ring together with the carbon atom to which R.sup.4 is bonded; R.sup.5 represents a hydrogen atom or a substituted or unsubstituted alkyl, cycloalkyl, alkylsulfonyl, arylsulfonyl, acyl or aryl group; R.sup.6 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or amino group, or a nitro group; and A represents CH or C-Y in which Y represents a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, or a protected or unprotected hydroxyl group, the quinolone-carboxylic acid derivative or its salt exhibiting a strong antibacterial activity against Gram-positive bacteria and Gram-negative bacteria, particularly against MRSA.
BACKGROUND ART
Compounds having a quinolonecarboxylic acid skeleton are used as a quinolone type synthetic anti-bacterial agent for curing infectious diseases, but no compound having a carbon-carbon bond between the carbon atom of an isoindoline ring and the carbon atom at the 7-position of a quinolonecarboxylic acid skeleton has been reported at all.
Norfloxacin, Ciprofloxacin, Ofloxacin and the like which have been widely used in clinic as a quinolone type synthetic antibacterial agent are not sufficient in activity against Gram-positive bacteria, in particular, MRSA. Accordingly, there is desired the development of synthetic antibacterial agents which are effective also against these bacteria and have a broad antibacterial spectrum.
DISCLOSURE OF THE INVENTION
Under such circumstances, the present inventors earnestly investigated and consequently found that the compound of the general formula [1] or its salt having a carbon-carbon bond between the carbon atom of an isoindoline ring and the carbon atom at the 7-position of a quinolonecarboxylic acid skeleton exhibits a strong antibacterial activity and is a very safe compound, whereby the present invention has been accomplished. The compound of the present invention is described below in detail.
In the present specification, unless otherwise specified, the term "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; the term "alkyl group" means a straight chain or branched chain C.sub.1-10 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl or the like; the term "lower alkyl group" means a straight chain or branched chain C.sub.1-5 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or the like; the term "alkenyl group" means a straight chain or branched chain C.sub.1-10 alkenyl group such as vinyl, allyl, isopropenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl or the like; the term "lower alkenyl group" means a straight chain or branched chain C.sub.2-5 alkenyl group such as vinyl, allyl or the like; the term "alkylidene group" means a straight chain or branched chain C.sub.1-10 alk
REFERENCES:
Chemical Abstracts 125:86618, abstract of Todo, 1995.
Hayashi Kazuya
Narita Hirokazu
Takahata Masahiro
Todo Yozo
Watanabe Yasuo
Seaman D. Margaret
Toyama Chemical Co., Ltd.
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