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Oxazolidinone derivatives as antimicrobials

A solvate, alkyl technology, applied in the field of substituted phenyl oxazolidinones and their synthesis

Inactive Publication Date: 2005-09-14
RANBAXY LAB LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite many disadvantages, vancomycin remains the drug of choice for the treatment of MRSA infections

Method used

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  • Oxazolidinone derivatives as antimicrobials
  • Oxazolidinone derivatives as antimicrobials
  • Oxazolidinone derivatives as antimicrobials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0194] (S)-N-[[3-[3-fluoro-4-(N-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (core I) analog

[0195] A heteroaryl group with a corresponding additional group can be introduced on the ring C nitrogen atom of the compound of formula I as follows:

[0196] General method:

[0197] Amines of formula VI with as suitable leaving groups (such as fluorine, chlorine, bromine, iodine, SCH 3 , SO 2 CH 3 、-SO 2 CF 3 , Tos or OC 6 h 5 etc.) R 12 The heteroaromatic compound of formula VII is reacted as shown in previous reaction scheme I. Q 1 , G, J and L are as defined in Formula II. The reaction is carried out in a suitable solvent such as dimethylformamide, dimethylacetamide, acetonitrile, dimethyl sulfoxide or ethylene glycol at a suitable temperature from -70°C to 180°C to give the compound of formula II.

[0198] In some cases, the presence of a suitable base such as triethylamine, diisopropylethylamine, potassium carbonate, potassium bicarbonate, dipotassium...

Embodiment 2

[0223] Analogs of (S)-N-[[4-(N-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (Core II)

[0224] Compound No. 6: (S)-N-[[3-[4-[N-1-(5-nitro-2-thienyl)piperazinyl]-phenyl]-2-oxo-5-oxa Preparation of oxazolidinyl]methyl]acetamide

[0225] Trifluoroacetic acid (S)-N-[[3-[4-(1-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (1.076mmol) and Acetone and K 2 CO 3 (200 mg) was stirred for 5 minutes, then filtered and concentrated under reduced pressure. The residue was dissolved in DMSO and stirred at room temperature. At room temperature, adding K 2 CO 3 (224mg, 1.61mmol) and 2-bromo-5-nitrothiophene (246mg, 1.18mmol) was stirred overnight. The reaction mixture was quenched with water and extracted with DCM. with anhydrous Na 2 SO 4 The organic layer was dried and concentrated under reduced pressure to obtain a crude product, which was purified by column chromatography. (Silica gel 100-200 mesh) Elution: 1-2% MeOH in DCM gave 75 mg of the title compo...

Embodiment 3

[0229] (S)-N-[[3-[3-fluoro-[4-(1-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]-2methyl]-chloropropane Analogs of amides (Core III)

[0230] Compound No. 7: (S)-N-[[3-[3-fluoro[4-[N-1-{4-(5-nitro-2-thienyl)piperazinyl}]-phenyl]- Preparation of 2-oxo-5-oxazolidinyl]methyl]-2-chloro-propionamide

[0231] (S)-N-[[3-fluoro-[4-(1-piperazinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl]-2-chloro-propionamide (WO 00 / 32599) (0.22 g, 0.454 mmol) was dissolved in acetonitrile. Here, N-ethyldiisopropylamine (0.117 g, 0.9 mmol) and 5-nitro-2-bromo-thiophene (0.13 g, 0.681 mmol) were added and the reaction mixture was heated at 60° C. for 6-8 hours. The reaction mixture was concentrated. The crude compound was purified by column chromatography eluting with 2% methanol in dichloromethane.

[0232]1 HNMR (CDCl 3 ): δppm 8.23(m, 1H, NH), 7.8(d, 1H, Ar-H), 7.47(m, 1H, Ar-H), 6.98(m, 1H, Ar-H), 6.95(m, 1H , Ar-H), 6.06(d, 1H, Ar-H), 4.79(m, 1H, CH), 4.45(m, 1H, CH), 4.0(m, 1H, CH), 3.81(m, 1H, CH)...

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PUM

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Abstract

The present invention relates to certain substituted phenyl oxazolidinones and to processes for the synthesis of the same. This invention also relates to pharmaceutical compositions containing the compounds of the present invention as antimicrobials. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as multiple-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms such as Bacterioides spp. and Clostridia spp. species, and acid fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.

Description

field of invention [0001] This invention relates to certain substituted phenyloxazolidinones and methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention as antibacterial agents. The compound is useful as an antimicrobial agent, effective against many human and veterinary pathogens, including gram-positive aerobic bacteria such as multi-resistant staphylococci, streptococci and enterococci, anaerobic organisms such as bacteroids and clostridia , and acid-resistant organisms such as Mycobacterium tuberculosis, Mycobacterium avium, and mycobacteria. Background of the invention [0002] The increasing antimicrobial resistance of Gram-positive bacteria has become a difficult management problem. Enterococci, although not traditionally virulent pathogens, have now been shown to cause approximately 40% mortality when associated with vancomycin resistance. Staphylococcus aureus, the traditional pathogen of po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P31/04C07D413/12C07D413/14
CPCC07D413/14C07D413/12A61P31/04
Inventor A·梅塔S·鲁德拉A·V·S·拉贾拉奥A·S·亚达夫A·拉坦
Owner RANBAXY LAB LTD
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