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Oxazolidinone compound containing pyridine and preparation method thereof

A technology of compound and alkyl, applied in the field of medicinal chemistry, can solve the problems such as the reduction of curative effect

Inactive Publication Date: 2011-09-14
SHENYANG J & HEALTH PHARMACY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, since the drug has been used for a long time, some drug-resistant bacteria have gradually emerged, reducing its efficacy, so it is necessary to find new drugs

Method used

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  • Oxazolidinone compound containing pyridine and preparation method thereof
  • Oxazolidinone compound containing pyridine and preparation method thereof
  • Oxazolidinone compound containing pyridine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 N-[[(5S)-3-fluoro-4-(2-aminopyrimidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide preparation of

[0057] 1.1 Preparation of N-[(2S)-2-acetoxy-3-chloropropyl]acetamide (IV)

[0058] 1.1.1 Preparation of (S)-1-amino-3-chloro-2-propanol hydrochloride

[0059] Dissolve 59.0g (0.56mol) of benzaldehyde in 150ml of ethanol, add dropwise 58.0ml (0.55mol) of ammonia water to the reaction solution, stir, and dropwise add 58ml (0.88mol) of (S)-epichlorohydrin to the reaction solution , Control the rate of addition to keep the reaction temperature below 40°C. After dropping, react at 35-40°C for 6h, then lower the reaction solution to room temperature and continue to react for 12h. Most of the solvent was distilled off under reduced pressure, and 100 ml of toluene was added. After stirring, the solution was raised to 35-40°C, and an aqueous hydrochloric acid solution (68ml hydrochloric acid, 77ml water) was added dropwise, and the solution was stirred at 35-40°C...

Embodiment 2

[0073] Example 2 N-[[(5S)-3-fluoro-4-(2-aminopyrimidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Preparation of hydrochloride

[0074] N-[[(5S)-3-fluoro-4-(2-aminopyrimidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide 5.2g (0.015mol) was added to 80% ethanol, under stirring, hydrochloric acid ethanol solution was added dropwise to pH = 2, heated to reflux, activated carbon was decolorized, filtered while hot, and dried to obtain N-[[(5S)-3-fluoro-4 -(2-aminopyrimidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide hydrochloride 5.4 g, yield 95.1%. mp: 227.3°C; [α] 20 D =-25.3 (c=1.00, DMSO).

Embodiment 3

[0075] Example 3 N-[[(5S)-3-fluoro-4-(2-aminopyrimidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Preparation of mesylate

[0076] N-[[(5S)-3-fluoro-4-(2-aminopyrimidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide 5.2g (0.015mol) was added to 80% ethanol, methanesulfonic acid was added dropwise under stirring until pH = 2, heated to reflux, activated carbon was decolorized, filtered while hot, and dried to obtain N-[[(5S)-3-fluoro-4 -(2-aminopyrimidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide methanesulfonate 6.2 g, yield 93.9%.

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Abstract

The invention provides an oxazolidinone compound containing pyridine shown in the formula I, a preparation method thereof, and an application of the compound in preparation of medicaments for treatingmicrobe-infected diseases.

Description

Technical field: [0001] The present invention relates to the field of medicinal chemistry, in particular to an oxazolidinone compound containing pyrimidine, or an optical isomer thereof, a pharmaceutically acceptable salt and / or solvate, a pharmaceutical composition containing them, a preparation method and application. Background technique: [0002] In recent decades, the abuse of antimicrobial drugs has led to a sharp increase in the mortality rate of infectious diseases. Clinically, the drug resistance of cells is increasing year by year, resulting in the reduction of the efficacy of some antibacterial drugs, or even ineffective, such as methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis and vancomycin-resistant enterococci; Pathogenic bacteria become conditional pathogens, such as Proteus, Pseudomonas aeruginosa and so on. The formation and development of all these drug-resistant strains have led to difficulties in treatment. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/10A61K31/506A61P31/00A61P31/04
Inventor 史秀兰
Owner SHENYANG J & HEALTH PHARMACY CO LTD