Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-08-04
1998-12-15
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546156, C07D40104, C07D47104, A61K 31435, A61K 3147
Patent
active
058497579
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to an antibacterial compound useful as medicines, animal drugs, fisheries drugs or antibacterial preservatives and to an antibacterial drug or antibacterial preparation which contains the same.
BACKGROUND ART
group as a substituent are disclosed in JP-A-64-56673 and JP-A-3-86875 (the term "JP-A" as used herein means an "unexamined published Japanese patent application), nothing is known about the quinolone derivative of the present invention which has the substituent derived from this amino-substituted condensed-bicyclic heterocyclic compound and also has a halogenocyclopropyl group at the 1-position.
Synthetic quinolone antibacterial agents having not only antibacterial activities but also excellent biological distribution such as oral absorbability, distribution into organs, urinary excretion ratio and the like have been found in recent years, and a number of such compounds are now supplied to the clinical field as chemotherapeutic agents effective against various infectious diseases. However, the presence of bacterial strains having low sensitivity to these drugs has been increasing in recent years in the clinical field. Also, like the case of Staphylococcus aureus (MRSA) having less sensitivity against .beta.-lactam antibiotics, strains having low sensitivity to synthetic quinolone antibacterial agents are increasing even among strains which are resistant to other drugs than synthetic quinolone antibacterial agents. In consequence, development of drugs having more higher efficacy has been called for in the clinical field.
DISCLOSURE OF INVENTION
The inventors of the present invention think that structures of the 7- and 1-position substituents are greatly concerned in the antibacterial activity, efficacy and safety of synthetic quinolone antibacterial agents. In consequence, the present inventors have conducted intensive studies to obtain a compound having high antibacterial activity against a broad range of bacteria including quinolone-resistant strains and found as the results that a quinolone derivative having a substituent group derived from an amino-substituted condensed-bicyclic heterocyclic compound at the 7-position shows strong antibacterial activity against Gram-positive and Gram-negative bacteria, particularly quinolone-resistant bacteria including MRSA, and that not only the antibacterial activity but also excellent efficacy and safety can be obtained by a quinolone derivative in which the 1-position is substituted with a halogenocyclopropyl group, particularly a fluorocyclopropyl group.
In the quinolone derivative of the present invention, a pair of enantiomer is attributed only to the 1-positioned halogenocyclopropane ring moiety even in the absence of stereoisomerism in other substituents. This is originated from a stereochemical relationship between pyridonecarboxylic acid moiety and halogen atom on the cyclopropane ring. When isomers formed in this way are racemic, these derivative is a mixture of enantiomers which could be used as a medicine as such.
On the other hand, when stereoisomerism is also present at other positions, particularly at the 7-position substitutent, in addition to the stereoisomerism of the halogenocyclopropene ring moiety, such quinolone derivative consists of diastereomers, meaning that 4 or more stereoisomers are present. Since the mixture of diastereomers is a mixture of compounds having different physical properties, it is difficult to administer the mixture as a medicine.
The present inventors have made intensive efforts to obtain a quinoline compound consisting of a single stereoisomer even in the case of a 1-(1,2-cis-2-halogenocyclopropyl)-substituted quinolone derivative which consists of diastereomers.
As the results, the present inventors have succeeded in obtaining each enantiomer of cis-2-fluorocyclopropylamine as a pure compound. The present inventors have also succeeded in obtaining each of the fluorocyclopropane ring-originated enantiomers of the quinolone derivative as a compound consisting of single iso
REFERENCES:
patent: 4649144 (1987-03-01), Matsumoto et al.
Kawakami Katsuhiro
Kawato Haruko
Kimura Ken-ichi
Kimura Youichi
Matsuhashi Norikazu
Daiichi Pharmaceutical Co. Ltd.
Kifle Bruck
Shah Mukund J.
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