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Quinolonecarboxylic acid derivatives or salts thereof

A technology of quinolone carboxylic acid and derivatives, applied in the field of novel quinolone carboxylic acid derivatives and their salts

Inactive Publication Date: 2004-06-02
TOYAMA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] On the other hand, people are still controversial about the safety of quinolone synthetic antibacterial agents, such as phototoxicity and mutagenicity

Method used

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  • Quinolonecarboxylic acid derivatives or salts thereof
  • Quinolonecarboxylic acid derivatives or salts thereof
  • Quinolonecarboxylic acid derivatives or salts thereof

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0390]12.24g of 2,6-dibromotoluene was dissolved in 120ml of toluene, and 2.94g of cyclopropylamine, 0.45g of tris(dibenzylideneacetone)dipalladium, 0.91 g of (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'binaphthyl and 6.12 g of tert-butoxysodium (Original text: natrium tert-butokisid). The mixed solution was stirred at 80°C for 1 hour under the atmosphere of argon. After cooling the reaction mixture, 210 ml of ice water and 60 ml of ethyl acetate were added, and the pH was adjusted to pH 1 with 6 mol / mL hydrochloric acid. The insoluble matter was filtered off, and the organic layer was extracted. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography [hexane:toluene=2:1] to obtain 9.31 g of N-cyclopropyl-3-bromo-2-methylaniline as a pale yellow oil.

[0391] IR (pure) cm -1 :3420

[0392] NMR (CDCl 3 ...

reference example 2

[0399] 0.68 g of N-cyclopropyl-3-bromo-2-methylaniline was dissolved in 0.65 g of diethyl ethoxymethylene malonate, and stirred at 130° C. for 4 hours. After distilling off generated methanol, 4.07 g of polyphosphoric acid was added, followed by stirring at 130° C. for 25 minutes. 20 ml of freezing point chloroform and 20 ml of water were added to the reaction mixture, and the organic layer was extracted. The extracted organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography [toluene:ethyl acetate=4:1] to obtain 0.47 g of 7-bromo-1-cyclopropyl-8-methyl-4 as a pale yellow crystal -Ethyl carbonyl-1,4-dihydro-3-quinolinecarboxylate.

[0400] IR(KBr)cm -1 : 1683, 1636

[0401] NMR (CDCl 3 )δ value: 0.8-1.6 (7H, m), 2.86 (3H, s), 3.8-4.2 (1H, m), 4.39 (2H, q, J = 7.2Hz), 7.60 (1H, d, J = 8.4 Hz), 8.16(1H, d, J=8.4Hz), 8.67(1H, s)

[0402] Melting ...

reference example 3

[0408] With 4.76g of 3-bromo-5-(cyclopropylamino)-4-methylbenzoic acid tert-butyl ester and 4.7g of ethoxymethylene malonate diethyl ester at 130°C Stir for 8 hours. After the generated ethanol was distilled off under reduced pressure, it was purified by silica gel column chromatography [hexane: ethyl acetate = 4: 1] to obtain 5.09 g of 2-{[3-bromo-5-(tert. -Butylcarboxy)cyclopropyl-2-toluidineamino]methylene}malonate diethyl.

[0409] NMR (CDCl 3 )δ value: 0.6-0.9 (4H, m), 1.1-1.4 (6H, m), 1.59 (9H, s), 2.34 (3H, s), 3.1-3.3 (1H, m), 3.6-4.3 (4H , m), 7.6-7.7 (2H, m), 8.1-8.2 (1H, m)

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Abstract

The present invention relates to a novel quinolonecarboxylic acid derivatives represented by general formula which have potent antibacterial effects on gram-positive bacteria, in particular, Propionibacterium acnes, wherein R<1> represents hydrogen or a carboxyl-protective group; R<2> represents optionally substituted cycloalkyl; R<3> represents hydrogen, halogeno, optionally substituted alkyl, alkoxy or alkylthio, optionally protected hydroxy or amino, or nitro; R<4> represents optionally substituted alkyl or alkoxy; Z represents halogeno, optionally substituted alkyl, alkenyl, cycloalkyl, alkoxy, alkylthio, amino or pyridin-4-yl or pyridin-3-yl optionally having one or more substituents selected from among optionally substituted hydroxy and amino.

Description

technical field [0001] The present invention relates to a novel quinolone carboxylic acid derivative and its salt. In particular, novel quinolone carboxylic acid derivatives and salts thereof have strong antibacterial effects on Gram-positive bacteria, especially Propionibacterium acnes (Corynebacterium acnes). Background technique [0002] It is well known that derivatives of 4-carbonylquinoline-1,4-dihydroxy-3-carboxylic acid have antibacterial activity. For example, at the seventh position of 4-carbonylquinoline-1,4-dihydroxyl-3-carboxylic acid, the pyridine can combined compound. [0003] In addition, the first position of 4-carbonylquinoline-1,4-dihydroxyl-3-carboxylic acid is a compound with a cyclopropyl group, such as the well-known Siprofloxacin (original text: Shiprofloxacin) Sasin) headed by many compounds. [0004] In addition, the derivatives of 4-carbonylquinoline-1,4-dihydroxy-3-carboxylic acid, that is, quinolones for external use on the skin, only Najifl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04
CPCC07D401/04Y02P20/55A61P31/04A61K31/47
Inventor 林一也鬼头德典满山顺一山川哲规黑田宏川渊启代
Owner TOYAMA CHEM CO LTD
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