Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1988-12-02
1990-07-10
Bond, Robert T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07F 502
Patent
active
049407945
DESCRIPTION:
BRIEF SUMMARY
This invention relates to new 1-substituted-6-fluoro-7-substituted-8-optionally fluoro-substituted-4-oxo-1,4-dihydro-quinoline-3-carboxylic-acid-boric acid-anhydride derivatives of the Formula I ##STR2## and to a process for the preparation thereof.
In the general Formula I CR.sup.5 R.sup.6 R.sup.7 (wherein R.sup.5, R.sup.6 and R.sup.7 stand for hydrogen or halogen) or phenyl optionally substituted by 1 or 2 halogen atoms, aliphatic acyloxy group containing 2 to 6 carbon atoms being optionally substituted by halogen, or an aromatic acyloxy group containing 7 to 11 carbon atoms,
BACKGROUND OF THE INVENTION
Ethyl(1-p-fluorophenyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carb oxylate) is an intermediate for the preparation of 1-p-fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-q uinoline-carboxylic acid of antibacterial activity (24th Intersci. Conf. Antimicrob. Agents. Chemother. 1984. Abst. 72-78). The latter compound can be prepared from ethyl-(1-p-fluorophenyl-6-fluor-7-chloro-4-oxo-1,4-dihydro-quinoline-3-car boxylate) in two steps. The 1-p-fluorophenyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-q uinoline-carboxylic acid can be prepared by reacting 1-p-fluorophenyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxyli c acid (obtained by hydrolyzing the ester) with 1-methyl-piperazine in the presence of a solvent at a temperature of 100.degree. C. for 20 hours (European Patent Specification No. 131839).
The ethyl-(1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carbo xylate) is an intermediate for the preparation of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline-car boxylic acid which has antibacterial activity (Eur. J. Clin. Microbiol. 1983., 2, 111). The latter compound can be obtained from ethyl-(1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carbo xylate) in two steps. After hydrolyzing the ester, the 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid thus obtained is reacted with piperazine in the presence of a solvent at a temperature of 135.degree.-140.degree. C. for two hours and thus 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperazinyl)-quinoline-3-carb oxylic acid can be prepared (German Off. No. 30 33 157 and No. 31 42 854).
The 1-substituted-6,7,8-trifluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid derivatives (GB patent No. 2057440, Belgian patent specification 887574, European patent No. 106489 and No. 15049, German patent No. 3433924, Japanese patent Nos. 60006684 and 61085381, Portugal patent No. 80187) are intermediates for the preparation of 7-substituted-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives (J. Med. Chem. 1986. 29, 445; Drugs Fut. 1984. 9, 246; 23rd Intersci. Conf. Antimicrob. Agents Chemother. 1983. Abstr. 658; 7th Int. Symp. Fut. Trends Chemother. 1986, 80).
DESCRIPTION OF THE INVENTION
According to the present invention 1-(optionally halo-substituted)ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-substituted-quinol ine-3-carboxylic acid derivatives, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(optionally substituted piperazino)-quinoline-3-carboxylic acid derivatives and 1-substituted-6-fluoro-1,4-dihydro-4-oxo-7(optionally substituted piperazino)-quinoline-3-carboxylic acid derivatives can be prepared in a simple manner by applying the new compounds of the general Formula I as starting material.
The compounds of the Formula I (wherein R, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as stated above) can be obtained by reacting a compound of the Formula ##STR3## wherein R.sup.8 stands for hydrogen or alkyl containing 1 to 4 carbon atoms and fluoroborate of the Formula III thereof or a triacyloxy borate derivative of the Formula V substituted by halogen or aryl containing 6 to 10 carbon atoms.
Borone trifluoride, boron tribromide, boron trichloride and complexes or aqueous solutions of these compounds can be used as compounds of the Formula IV. Preferably complexes of ethers or alcohols may be used (e.g. a complex of
REFERENCES:
patent: 4803274 (1989-02-01), Hermecz et al.
patent: 4806645 (1989-02-01), Hermecz et al.
Halogh Maria
Hermecz Istvan
Horvath Agnes
Kereszturi Geza
Marmarosi Katalin
Bond Robert T.
Chinoin Gyogyszer - es Vegyeszeti Termekek Gyara Rt.
Dubno Herbert
Myers Jonathan
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