Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-08-04
1999-11-23
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514258, 514267, 514291, 514293, 514296, 514300, 514312, 514412, 544234, 544235, 544236, 544238, 544250, 544279, 546 80, 546 83, 546 89, 546 92, 546123, 546156, 548515, A61K 3147, A61K 3140, C07D20952, C07D40104
Patent
active
059901063
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to novel compounds useful as antibacterial agents, and bicyclic amines useful as intermediates for the synthesis thereof.
BACKGROUND ART
A variety of antibacterial pyridonecarboxylic acid derivatives are known. For example, Japanese Patent Application Laid-Open No. 56673/'89 describes pyridonecarboxylic acids of the general formula ##STR2## wherein R represents a lower alkyl group, a halogenated lower alkyl group, a lower alkenyl group, a cycloalkyl group, or a phenyl group which may have one or more substituents; X represents a nitrogen atom or C--A in which A represents a hydrogen atom or a halogen atom; Y represents a hydrogen atom or a halogen atom; and Z represents a group of the formula ##STR3## in which R.sub.1 represents a hydrogen atom, a lower alkyloxycarbonyl group, or an acyl group that may be substituted by one or more halogen atoms; two of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are connected directly or through a lower alkyl chain to form a ring, and the others represent hydrogen atoms; and n is 0 or 1, provided that R.sub.25 and R.sub.3 are directly connected. However, no specific example of a compound of the above formula (A) in which R.sub.4 and R.sub.5 are connected through an ethylene chain to form a ring is disclosed therein.
Moreover, European Patent Application Laid-Open No. 0343524 discloses pyridonecarboxylic acid derivatives of the general formula ##STR4## wherein R.sub.1 is hydrogen, hydroxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, oxo, halogen, or amino which may optionally be substituted by C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkanoyl; R.sub.2 is azido, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkanoyl, or amino which may optionally be substituted by C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkanoyl: A is ##STR5## R.sub.3 is hydrogen or a carboxyl-protecting group; R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 cycloalkyl, mono- or difluorophenyl, or a five-membered or six-membered heterocyclic group which may optionally be substituted by halogen and/or C.sub.1 -C.sub.4 alkyl; R.sub.5 is hydrogen, amino, hydroxy or C.sub.1 -C.sub.4 alkoxy; R.sub.6 is halogen: X is CH-(C.sub.1 --C.sub.4 alkyl), C.dbd.CH.sub.2, N--H or N--(C.sub.1 -C.sub.4 alkyl); Z is CQ or N; Q is hydrogen, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 alkyl or cyano; m is an integer of 0 or 1; and n and p are each an integer of 1 to 3. However, they do not include any compound in which n is 0.
Furthermore, Chemical Abstract, 66, 37500b (1967) and Japanese Patent Application Laid-Open No. 11729/'81 disclose compounds of the formula ##STR6## wherein R represents a hydrogen atom or a carboxyl group.
Conventional pyridonecarboxylic acid derivatives substituted by a bicyclic amino group, such as those represented by the above general formulae (A) and (B), are useful as antibacterial agents. However, their antibacterial activities and, in particular, in vivo antibacterial activities are not always satisfactory.
The present invention has been completed as a result of extensive investigations conducted with a view to developing a pyridonecarboxylic acid derivative showing a further enhancement in antibacterial activity and, in particular, in vivo antibacterial activity.
DISCLOSURE OF THE INVENTION
According to the present invention, there are provided novel bicyclic amino group-substituted pyridonecarboxylic acid derivatives of the general formula (I) joined to the 7-position of the pyridonecarboxylic acid or a position equivalent to the 7-position thereof. ##STR7## wherein R.sub.1 and R.sub.2 may be the same or different and each represents a hydrogen atom, a lower alkyl group or an amino-protecting group; R.sub.3 and R.sub.4 may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an oxo group, a lower alkoxy group or a lower alkyl group; and n is an integer of 0 or 1.
According to the present invention, there ar
REFERENCES:
duPont, Chem. Abstr., vol. 66 (1967) p 3554, Abstract No. 37500b.
Chiba et al., Chem. Abstr., vol. 111, No. 17, Oct. 23, 1989 Abstract No. 111-153779w.
Chiba Katsumi
Minami Akira
Sakamoto Masato
Tominaga Yukio
Coleman Brenda
Dainippon Pharmaceutical Co., Ltd.
Shah Mukund J.
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