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Antimicrobial quinolones, their compositions and uses

a technology of quinolones and quinolones, applied in the field of antimicrobial compounds, can solve the problems of limited capacity of existing antibacterials to overcome the threat, few antimicrobials are produced that are truly clinically acceptable, and a significant threat to public health in the developed world, so as to reduce the susceptibility to microbial resistance, improve pharmacology, and reduce the effect of toxicity

Inactive Publication Date: 2004-02-12
THE PROCTER & GAMBLE COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0031] It has been found that the compounds of this invention, and compositions containing these compounds, are effective antimicrobial agents against a broad range of pathogenic microorganisms with advantages in low susceptibility to microbial resistance, reduced toxicity, and improved pharmacology.

Problems solved by technology

However, many such attempts to produce improved antimicrobials yield equivocal results.
Indeed, few antimicrobials are produced that are truly clinically-acceptable in terms of their spectrum of antimicrobial activity, avoidance of microbial resistance, and pharmacology.
Examples of bacterial infections resistant to antibiotic therapy have been reported in the past; they are now a significant threat to public health in the developed world.
Hence existing antibacterials have limited capacity in overcoming the threat of resistance.

Method used

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  • Antimicrobial quinolones, their compositions and uses
  • Antimicrobial quinolones, their compositions and uses
  • Antimicrobial quinolones, their compositions and uses

Examples

Experimental program
Comparison scheme
Effect test

example a

PRECURSOR EXAMPLE A

[0142] 182

3-methoxy-2,4,5-trifluorobenzoyl chloride

[0143] 3-Methoxy-2,4,5-difluorobenzoic acid (43.9 g) is suspended in dichloromethane (30 mL) and oxalyl chloride (25 mL) is added followed by 4 drops of dry dimethyl formamide (DMF). The mixture is stirred at room temperature for 6 hours and the solvent is removed by evaporation to afford the desired product.

Ethyl 2,4,5-trifluoro-3-methoxy-benzoyl acetate

[0144] Monoethyl malonate (26.4 g) is dissolved in tetrahydrofuran (THF) (700 mL). The solution is cooled at -50.degree. C. and n-butyllithium (160 mL 2.5 M) is added, keeping the temperature below -50.degree. C. The temperature is initially raised to 0.degree. C. and cooled back to -50.degree. C. 3-methoxy-2,4,5trifluorobenzoyl chloride (20.6 g) is added, keeping the temperature at -50.degree. C., then the reaction mixture is warmed to room temperature. Hydrochloric acid is added until the pH becomes acidic. The organic phase is washed with sodium bicarbonate and...

example 1

7-(Trans-3-amino-4-ethyl-piperidine-1-yl)-1-Cyclopropyl-1,4-dihydro-6-fluo- ro-8-methoxy-4-oxo-quinoline-3-carboxylic acid hydrochloride

[0202] 189

[0203] 1-Cyclopropyl-1,4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-- carboxylic acid (Precursor A) (0.059 g), Trans,3-tert-butoxycarbonylamino-- 4-ethyl-piperidine (Precursor F) (0.048 mg) and triethylamine (0.075 mL) are dissolved in N-methyl-pyrrolidone (2 mL). The reaction mixture is stirred at 80.degree. C. for 5 hours, then is poured on an ice / water mixture. The pH is lowered to 2 with diluted HCl and the resulting precipitate is filtered. The solid is then suspended in ethanol and 6N HCl is added. After 18 hours at room temperature, the desired final product is collected by filtration.

example 2

7-[Trans-3-amino-4-(2-hydroxy-ethyl)-piperidine-1-yl]-1-Cyclopropyl-1,4-di- hydro-6-fluoro-8-methoxy-4-oxo-quinoline-3-carboxylic acid hydrochloride

[0204] 190

[0205] A procedure similar to Example 1 above is used, using 1-Cyclopropyl-1,4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-carbox- ylic acid (Precursor A) and Trans 4-(2-hydroxy-ethyl)-3tertbutoxycarbonyla- mino-piperidine (Precursor G) as the starting materials. The procedure utilizes the same reaction conditions and molar ratio of reactants as Example 1.

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Abstract

Compounds of the following formula: 1 are effective antimicrobial agents.

Description

CROSS REFERENCE[0001] This application claims priority under Title 35, United States Code 119(e) from Provisional Application Serial No. 60 / 255,634, filed Dec. 14, 2000.FIELD OF THE INVENTION[0002] The subject invention relates to novel antimicrobial compounds, their compositions and their uses.BACKGROUND[0003] The chemical and medical literature describes compounds that are said to be antimicrobial, i.e., capable of destroying or suppressing the growth or reproduction of microorganisms, such as bacteria. For example, such antibacterials and other antimicrobials are described in Antibiotics. Chemotherapeutics, and Antibacterial Agents for Disease Control (M. Grayson, editor, 1982), and E. Gale et al., The Molecular Basis of Antibiotic Action 2d edition (1981).[0004] The mechanism of action of these antibacterials vary. However, they are generally believed to function in one or more of the following ways: by inhibiting cell wall synthesis or repair; by altering cell wall permeability...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A01N43/42A01N43/90A61K31/4545A61K31/4709A61K31/4738A61K31/5383A61P31/04A61P43/00C07D401/04C07D455/02C07D471/04C07D498/06C07D513/04
CPCA01N43/42A01N43/90C07D513/04C07D455/02C07D471/04C07D401/04A61P31/04A61P43/00
Inventor LEDOUSSAL, BENOITHU, XIUFENG ERICALMSTEAD, JI-IN KIMGRAY, JEFFREY LYLE
Owner THE PROCTER & GAMBLE COMPANY
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