Quinolone derivatives and processes for preparing the same

Details Quinolone derivatives and processes for preparing the same Quinolone derivatives and processes for preparing the same

1995-10-11

1998-06-23

Dentz, Bernard

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

5142315, 514294, 514300, 544 32, 544101, 546 94, 546113, 546123, A61K 3147, C07D21556

Patent

active

057705976

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/KR94/00005 filed Jan. 18, 1994.


TECHNICAL FIELD

The present invention relates to novel quinolone derivatives which have a broad antibacterial spectrum, and processes for preparing the same.


BACKGROUND ART

Nalidixic acid developed in 1963 is the first one of quinolonecarboxylic acid-type antibacterials. Quinolonecarboxylic acid-type antibacterials are known to exhibit strong antibacterial activity against aerobic Gram-negative bacteria and have been effectively used as a treatment for urethritis. Among these quinolone carboxylic acid-type antibacterials, especially norfloxacin, ciprofloxacin, of loxacin, etc. are clinically used. However, these prior art compounds suffer from the disadvantage that they have drastically inferior antibacterial activity against Gram-positive bacteria, while they have superior antibacterial activity against Gram-negative bacteria. Especially, these quinolone-type antibacterials are known to have weak antibacterial activity against Gram-positive bacteria such as Staphylococcus or Enterococcus which show high resistance to sepem-type or .beta.-lactam-type antibacterial agents.


DISCLOSURE OF INVENTION

The present invention provides novel quinolone derivatives of formula (I), (III) and (IV) below and processes for preparing the same. ##STR1## wherein, X.sub.1 represents hydrogen, amino group, halogen such as chloro, fluoro, or lower alkyl such as methyl; group; 3 carbon atoms or a straight chain or cyclic lower alkyl group having 1 to 3 carbon atoms which is substituted with a halogen atom, a phenyl group or a phenyl group substituted with one or two halogen atoms; group, ethoxycarbonyl group or nitryl group; and ##STR2## in which Y represents hydrogen, halogen, lower alkyl or alkoxy or together with R.sub.1 forms --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --OCH.sub.2 CH.sub.2 --, --OCH.sub.2 CH(CH.sub.3)--, --SCH,CH.sub.2 --, or --SCH.sub.2 CH(CH.sub.3)--. methoxymethyn, or methylmethyn. such as methyl or ethyl. X.sub.2 halogen is preferably fluorine. cyclopropyl or halogen substituted phenyl.
The present invention is described in detail hereinbelow.
The present invention provides novel quinolone carboxylic acid derivatives of formula (I), and specifically, to novel quinolone carboxylic acid derivatives of formula (I) below which have (II) at 7-position of quinolone nucleus and possess a broad spectrum of potent antibacterial activities, and to processes for preparing the same. ##STR3## wherein, X.sub.1, X.sub.2, Y.sub.1, Y.sub.2, R.sub.1, R.sub.2, and A are the same as defined above.
The present invention also provides novel quinolone carboxylic acid derivatives represented by the formula (III) and (IV) including mixtures thereof which show a broad spectrum of potent antibacterial activities, and to processes for preparing the same. ##STR4## wherein, X.sub.1, X.sub.2, Y.sub.1, Y.sub.2, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and A are the same as defined above. derivatives represented by the formula (II) which are used as a side chain at 7-position of novel quinolone carboxylic acid derivatives (I) and processes for preparing the same. ##STR5## wherein, Y.sub.1, Y.sub.2, and R.sub.2 are the same as defined above.
The present invention also provides novel processes for preparing formula (V) which are used as a side chain at 7-position of formula (IV) above. ##STR6## wherein, Y.sub.1 and R.sub.2 are the same as defined above.
Quinolone derivatives of formula (I) according to the present invention may be prepared by condensing optionally protected trans-2,8-diazabicyclo formula (VI-1) (P. D. Fernandes, "International Telesymposium on Quinolone", J. R. Prous Science, Barcelona, Spain, 1989. 1-143) in a solvent, in the presence of an inorganic or organic base, as described in the process (A). Inorganic bases used in this process include potassium carbonate and the like. Organic base used herein include The above reaction may be carried out at a temperature between room temperature and 150.degree. C. The reaction time is a

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