Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-04-25
1997-09-16
Grumbling, Matthew V.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546156, C07D215233, A61K 3147
Patent
active
056681470
DESCRIPTION:
BRIEF SUMMARY
This is a national phase application filed under 35 U.S.C 371 of PCT/JP94/01815 filed Oct. 27, 1994.
1. Technical Field
The present invention relates to new quinolinecarboxylic acid derivatives and salts thereof having antibacterial activities, which are useful as a medicine, a veterinary drug, a fishery drug, an agricultural chemical, a preservative, an industrial sterilizer, and the like, and new pyrrolidine derivatives and salts thereof which are intermediates for synthesizing the quinolinecarboxylic acid derivatives.
2. Background Art
Quinolone antibacterial agents developed in recent years, for example, Norfloxacin, Ofloxacin, Ciprofloxacin and Tosufloxacin, which have broad antibacterial spectra and excellent antibacterial activities against gram-positive bacteria and gram-negative bacteria, are now frequently used for treatments of various bacterial infectious diseases. Recently, however, since the third generation cephem drugs, which have a little weak antibacterial activity against gram-positive bacteria, have been generally used, infectious diseases with gram-positive bacteria centering around staphylococcus are increasing; further, appearance of resistant strains such as MRSA (methicillin-resistant staphylococcus) has become a large problem in the field of clinical medicine.
Commercially available quinolone antibacterial agents have a defect of lacking a strong antibacterial activity against gram-positive bacteria such as streptococcus and enterococcus. Additionally, their antibacterial activity against resistant strains such as MRSA are still insufficient. Therefore, a newly developed drug has been desired.
Under these circumstances, the present inventors earnestly made a study for proving an excellent synthetic antibacterial agent in which the above requirements are improved and consequently found that the quinolinecarboxylic acid derivatives and salts thereof shown below have broad antibacterial activity and especially strong antibacterial activity against gram-positive bacteria and resistant strains thereof, particularly MRSA, to complete the present invention.
DISCLOSURE OF THE INVENTION
The present invent ion provides quinolinecarboxylic acid derivatives which are represented by the general formula (I) ##STR3## wherein R.sub.1 is a C.sub.1 to C.sub.6 alkyl group which may be substituted, a C.sub.2 to C.sub.6 alkenyl group which may be substituted, a C.sub.3 to C.sub.7 cycloalkyl group which may be substituted or an aryl group which may be substituted, protected, amino group or a C.sub.1 to C.sub.6 alkylamino group each of which may be protected; a C.sub.1 to C.sub.6 dialkylamino group or a C.sub.1 to C.sub.6 alkyl group, ##STR4## wherein A' is hydrogen atom, a halogen atom, a C.sub.1 to C.sub.6 alkyl group, a C.sub.1 to C.sub.6 alkoxyl group which may be substituted, cyano group, or nitro group, and A' may form a ring with R.sub.1 ; the ring may include oxygen atom, nitrogen atom, or sulfur atom as a constituent atom; the ring may be substituted with a C.sub.1 to C.sub.6 alkyl group, may be protected, thereof, which are represented by the general formula (II) ##STR5## wherein X is hydroxymethyl group, aminomethyl group or amino group each of which may be protected, and salts thereof.
Further, the present invention provides antibacterial agents which comprise the compounds represented by the above general formula (I) or salts thereof as active ingredients and, additionally, methods of treating a bacterial infectious diseases wherein the compounds represented by the above general formula (I) are used.
The feature of the compounds of the present invention is that when a pyrrolidine residue with trifluoromethyl group combines to quinolinecarboxylic acid, the resulting compound has a broad antibacterial spectra and a strong antibacterial activity, especially, against gram-positive bacteria including MRSA.
BEST MODE FOR CARRYING OUT THE INVENTION
Examples of the C.sub.1 to C.sub.6 alkyl group which may be substituted, represented by R.sub.1, in the general formula (I) are, for instance, me
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Arika Tadashi
Fukui Hideto
Maejima Tetsuro
Nakano Jun
Senda Hisato
Grumbling Matthew V.
Kaken Pharmaceutical Co. Ltd.
Rao Deepak R.
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