Pyridonecarboxylic acid derivatives and intermediates for the sy

Details Pyridonecarboxylic acid derivatives and intermediates for the sy Pyridonecarboxylic acid derivatives and intermediates for the sy

1998-08-25

2000-01-25

Huang, Evelyn Mei

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

5142302, 5142292, 514300, 514312, 544 66, 544101, 546123, 546156, 548453, A61K 3147, A61K 31535, C07D21556, C07D47104, C07D49148

Patent

active

060179112

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to novel pyridonecarboxylic acid derivatives useful as antibacterial agents, and novel intermediates for the synthesis thereof.


BACKGROUND ART

A variety of antibacterial pyridonecarboxylic acid derivatives are known. For example, Japanese Patent Laid-Open No. 239857/'94 (corresponding to European Patent Application Laid-Open No. EP-A-603887) discloses compounds of the general formula (A) ##STR2## wherein: X.sub.1 and X.sub.2 are each a halogen atom; like; constituting the substituent group at the 7-position is composed of a first ring containing a nitrogen atom and a second ring containing an oxygen atom or the like. However, as to the substituent group on the first ring, these compounds differ from the compounds of the present invention which are represented by the formula (I) that will be given later. Moreover, in the compounds of the above formula (A) which are specifically described in the aforementioned Japanese Patent Laid-Open No. 239857/'94, only the following three groups are disclosed as examples of the bicyclic amino groups at the 7-position. ##STR3##
Moreover, Japanese Patent Laid-Open No. 192262/'94 (corresponding to European Patent Application Laid-Open No. EP-A-589318) discloses compounds of the general formula (B) ##STR4## wherein: X.sub.1 is halogen or nitro; ##STR5## in which R.sub.3 and R.sub.4 are each hydrogen, methyl or the like. However, the bicyclic amino group (Z) constituting the substituent group at the 7-position in these compounds differs from that present in the compounds of the present invention, as to the mode of fusion between the first ring containing a nitrogen atom and the second ring containing an oxygen atom.


DISCLOSURE OF THE INVENTION

According to the present invention, there are provided novel pyridonecarboxylic acid derivatives of the following general formula (I) [which may hereinafter referred to as the compounds (I) of the present invention], esters thereof and salts thereof. ##STR6## wherein: R represents a lower alkyl group, a lower alkenyl group or a lower cycloalkyl group (all of which may optionally be substituted by one or more halogen atoms), or represents a phenyl group which may optionally be substituted by one or more halogen atoms and/or an amino group; alkyl group, a lower alkoxy group or an amino group which may be protected; represents a hydrogen atom, a halogen atom or a cyano group, represents a lower alkoxy group, a lower alkyl group, a lower alkylthio group, a lower alkenyl group or a lower alkynyl group (all of which may optionally be substituted by one or more halogen atoms), or combines with R to form a bridge represented by the formula --O--CH.sub.2 --CH(CH.sub.3)--; hydrogen atom, a lower alkyl group or an amino-protecting group; different and each represent a hydrogen atom, a halogen atom or a lower alkyl group;
According to the present invention, there are also provided novel bicyclic amine compounds of the following general formula (II) and salts thereof which are useful as intermediates for the synthesis of pyridonecarboxylic acid derivatives of the above formula (I). ##STR7## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, m, n and p have the same meanings as described previously.
The compounds (I) of the present invention are structurally characterized by the fact that a conventionally unknown bicyclic amino group of the following general formula is joined to the 7-position of a specific pyridonecarboxylic acid or a position equivalent to the 7-position thereof. ##STR8## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, m, n and p have the same meanings as described previously.
The compounds (I) of the present invention, which have the above-described structural features, exhibit excellent antibacterial activity, especially against Gram-positive bacteria, and are hence useful as antibacterial agents.
The compounds of the present invention will be more specifically explained hereinbelow.
As used herein, the ter

REFERENCES:
patent: 4988709 (1991-01-01), Ogata et al.
patent: 5106854 (1992-04-01), Tsuji et al.
patent: 5395944 (1995-03-01), Petersen et al.
patent: 5654318 (1997-08-01), Takemura et al.

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