Unlock instant, AI-driven research and patent intelligence for your innovation.

Novel oxazolidinone compound

A compound, oxazolidine technology, applied in the field of medicinal chemistry, can solve the problem that the antibacterial spectrum cannot fully cover upper respiratory tract infection

Active Publication Date: 2013-10-23
南京汇诚制药有限公司
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, a variety of oxazolidinone derivatives have been disclosed, but so far, only linezolid (ZYVOX) has been approved as a single antibacterial agent in the oxazolidinone class for the treatment of microbial infections, but it has been used for a long time In the latter part, reversible thrombocytopenia and other myelosuppressive reactions appeared, and the antibacterial spectrum of the drug could not sufficiently cover the upper respiratory tract infections caused by Haemophilus influenzae, Moraxella catarrhalis and atypical pathogens, so the new anti-infection agents are still in great demand

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel oxazolidinone compound
  • Novel oxazolidinone compound
  • Novel oxazolidinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The synthesis of embodiment 1 (3-fluoro-4-bromophenyl) benzyl carbamate

[0073] Weigh 20.3g of 3-fluoro-4-bromoaniline into a 500ml three-necked reaction flask, add 140ml of methanol and 70ml of water, stir to dissolve, add 18g of sodium bicarbonate and 18g of benzyl chloroformate at 0~10℃, The reaction was carried out for 1 hour. The reaction solution was poured into 300ml of ice water, a large amount of white solid was precipitated, filtered and dried to obtain the title compound, ESIMS (m / z): 325 (M+H) + , calculated value: 324.1.

Embodiment 2

[0074] The synthesis of embodiment 23-fluoro-4-(4-hydroxymethylphenyl) benzyl carbamate

[0075] Weigh 17.4g of benzyl (3-fluoro-4-bromophenyl)carbamate in a 500ml single-necked bottle, add 180ml of toluene, 11.4g of 4-hydroxymethylphenylboronic acid, 22.2g of potassium carbonate, 60ml of ethanol, and 60ml of water and Pd(PPh 3 ) 4 3.15 g, heated to complete the reaction under the protection of nitrogen, then stopped the reaction, and cooled to room temperature. The reaction solution was concentrated and extracted with ethyl acetate (3×30 ml). The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. Filtration, concentration, and the residue was purified by column chromatography to obtain the title compound, ESIMS (m / z): 352 (M+H) + , calculated value: 351.1.

Embodiment 3

[0076] Synthesis of Example 3 (R)-3-[4-(4-aminomethylphenyl)-3-fluorophenyl]-5-hydroxymethyloxazolidin-2-one

[0077] Step A: Synthesis of benzyl 3-fluoro-{4-[(isoindoline-1,3-diketonyl)methyl]phenyl}phenylcarbamate

[0078] Weigh 0.72g of benzyl 3-fluoro-4-(4-hydroxymethylphenyl)phenylcarbamate into a 100ml single-necked bottle, add 25ml of anhydrous tetrahydrofuran and 0.88g of phthalimide at 0-10°C , triphenylphosphine 1.57g, slowly dropwise added diethyl azodicarboxylate (DEAD) anhydrous THF solution (0.5ml dissolved in 5ml) under nitrogen protection, and reacted at 0-10°C for 4 hours. The reaction solution was concentrated and extracted with dichloromethane (3×50ml), 5% NaHCO 3 Wash with aqueous solution (2×30ml), combine the organic layers, wash with saturated brine, and dry over anhydrous sodium sulfate. Filtration, the title compound purified by column chromatography, ESIMS (m / z): 479 (M-H) - , calculated value: 480.1.

[0079] Step B: Synthesis of benzyl 3-fluoro-...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a novel and effective oxazolidinone derivative, as well as an isomer, a pharmaceutically acceptable salt, a chemical protection form and a prodrug thereof.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a novel oxazolidinone derivative, a preparation method, a pharmaceutical composition containing the derivative, and the use of the derivative in anti-infective diseases. Background technique [0002] The rapid development of drug-resistant bacteria of various antibiotics and antibacterial drugs has seriously threatened the life and health of patients with infectious diseases. Exploring new drugs against drug-resistant Gram-positive bacteria has become a research hotspot in the medical field at home and abroad. Oxazolidinone antibacterial drugs are a new class of chemically fully synthetic antibacterial drugs developed after sulfonamides and fluoroquinolones in the past 30 years. They can kill Gram-positive pathogens by inhibiting protein synthesis at a very early stage. Efficacy of multidrug-resistant Gram-positive bacteria. [0003] In the prior art, a variety of oxazolidinone ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D487/04C07D263/22A61K31/421A61K31/427A61K31/422A61K31/443A61K31/496A61K31/4985A61K31/5377A61K31/5513A61P31/00
Inventor 王勇张仓沙向阳王利娟张迪
Owner 南京汇诚制药有限公司