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|Title:||Quinoline carboxylic acid derivatives having 7-(4-amino-methyl-3-oxime) pyrrolidine substituent and processes for preparing thereof|
|Abstract:||The present invention relates to a novel quinolone compound having an excellent antibacterial activity. More specifically, the present invention relates to a novel quinoline(naphthyridine)carboxylic acid derivative represented by the following formula (I), which has an 4-aminomethyl-3-oximepyrrolidine substituent on 7-position of the quinolone nucleus and shows a superior antibacterial activity in contrast to the known quinolone antibacterial agents having a weak activity against gram-positive bacterial strains and also has a broad antibacterial spectrum and a highly improved pharmacokinetic property: ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and Q are defined as described in the specification.|
|Inventor(s):||Hong; Chang Y. (Daejeon, KR), Kim; Young K. (Kyungki-do, KR), Chang; Jay H. (Daejeon, KR), Kim; Se H. (Seoul, KR), Choi; Hoon (Daejeon, KR), Nam; Do H. (Daejeon, KR), Kwak; Jin H. (Daejeon, KR), Jeong; Yi N. (Daejeon, KR), Oh; Jeong I. (Daejeon, KR), Kim; Mu Y. (Daejeon, KR)|
|Assignee:||LG Chemical Ltd. (Seoul, KR)|
1. A naphthyridine carboxylic acid compound represented by the following formula (I) : ##STR267## and its pharmaceutically acceptable non-toxic salt, its physiologically
hydrolyzable ester, solvate and isomer, in which
R represents hydrogen, methyl or amino;
Q represents N;
R.sub.1 represents cyclopropyl, ethyl, or phenyl which is substituted with one or more fluorine atom(s);
R.sub.2 represents one of the following a) through e):
a) hydrogen, straight or branched C.sub.1 -C.sub.4 alkyl, cyclopropyl, cyclopropylmethyl, C.sub.3 -C.sub.6 alkynyl, 2-haloethyl, methoxymethyl, methoxycarbonylmethyl, aryl or allyl,
b) a group of the following formula (1), ##STR268## wherein X represents hydrogen, 2, 3 or 4-fluoro, cyano, nitro, methoxy, C.sub.1 -C.sub.4 alkyl, or 2,4-difluoro,
c) a group of the following formula (2), ##STR269## d) a heteroarylmethyl of the following formula (3), ##STR270## e) a group of the following formula (4), ##STR271## wherein n denotes 0 or 1, m denotes 0, 1 or 2 and X represents methylene, O or N, and
R.sub.3 and R.sub.4 independently of one another represent hydrogen or C.sub.1 -C.sub.3 alkyl or R.sub.3 and R.sub.4 together with a nitrogen atom to which they are attached can form a ring.
2. The compound of claim 1, wherein Q represents N, R represents hydrogen or amino, R.sub.1 represents cyclopropyl or 2,4-difluorophenyl, and R.sub.2 represents hydrogen, methyl, isopropyl, t-butyl, phenyl, homopropargyl, 2-fluoroethyl, benzyl, 2-fluorobenzyl, 2-methylbenzyl or 2-methoxybenzyl.
3. The compound of claim 2, wherein Q represents N, R represents hydrogen or amino, R.sub.1 represents cyclopropyl and R.sub.2 represents methyl, t-butyl, homopropargyl, 2-fluoroethyl, benzyl, 2-fluorobenzyl or 2-methoxybenzyl.
4. The compound of anyone of claims 1 to 3, wherein R.sub.3 and R.sub.4 are hydrogen.
5. An antibacterial composition comprising as an active component the compound of formula (I) as defined in claim 1, together with a pharmaceutically acceptable carrier.
6. The composition of claim 5 comprising 1 to 100 mg of the compound of formula (I) in a unit dosage form.