Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation of levo flurbi profen

A technology of flurbiprofen and racemization, which is applied in the field of preparation of levoflurbiprofen, can solve the problems that the optical purity of levoflurbiprofen can only reach 73%, and is beneficial to industrial production, with mild reaction conditions, Effect of production cost reduction

Inactive Publication Date: 2004-12-22
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
View PDF1 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the patent "Preparation Method of Optically Pure 2-fluoro-α-methyl-[1,1'-diphenyl]-4-acetic acid" (publication number: CN1326922A) applied by our laboratory in 2001, it can be prepared Obtaining the optical purity of 99% dexflurbiprofen, but the optical purity of levoflurbiprofen can only reach 73%

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
  • Preparation of levo flurbi profen
  • Preparation of levo flurbi profen
  • Preparation of levo flurbi profen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] 234.3 grams of racemic flurbiprofen (purity 95%) were dissolved in 1515 milliliters of absolute ethanol, and 144.2 grams of (2R, 3S)-2-amino-3-hydroxyl-3-p-methylsulfone phenylpropionic acid ethyl ester was added (purity 91%), heated and co-flowed for 15 minutes, cooled to room temperature, precipitated crystals, filtered to obtain 227.4 grams of crude salt, and this crude salt was recrystallized twice with absolute ethanol to obtain 162.8 grams of pure product, its single crystal X- The ray spectrogram is shown in Figure 1. Suspend it in 470 ml of ethyl acetate, add 670 ml of 2N sulfuric acid aqueous solution, separate the layers, extract the inorganic phase with ethyl acetate (2 × 150ml), combine the organic phases, wash with 300 ml of 2N sulfuric acid aqueous solution, and then wash with water ( 4 × 200ml), dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 72.8 grams of crude acid, which was dissolved in 280 milliliters of glacial acetic acid, ...

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

PropertyMeasurementUnit
optical purityaaaaaaaaaa
optical purityaaaaaaaaaa
Login to View More

Abstract

A process for preparing leavo-flurbiprofen includes dissolving dl-flurbiprofen in solvent, adding (2R, 3S)-2-amino-3-hydroxy-3-p-methylsulfonyl phenylpropionate, raecting, cooling, crystallizing, filtering, recrystallizing, suspending in organic solvent, adding inorganic acid or its aqueous solution, separating liquid, and concentrating organic phase. Its advantages are high output rate and high optical purity (more than 99%).

Description

technical field [0001] The present invention relates to a kind of utilizing (2R, 3S)-2-amino-3-hydroxy-3-p-thymphenylpropionate to resolve racemic flurbiprofen (2-fluoro-α-methyl-[1 , 1'-diphenyl]-4-acetic acid) to directly prepare levoflurbiprofen ((R)-2-fluoro-α-methyl-[1,1'-diphenyl]-4-acetic acid) Methods. Background technique [0002] Flurbiprofen is a non-steroidal anti-inflammatory drug, which can reduce inflammation and analgesia, and is used to treat rheumatic diseases. It is its racemate that is currently sold and clinically used in the market. However, the pharmacological activities of levoflurbiprofen and dexflurbiprofen ((R)-2-fluoro-α-methyl-[1,1'-diphenyl]-4-acetic acid) are not the same, The anti-inflammatory activity of flurbiprofen mainly comes from dex-flurbiprofen, and levo-flurbiprofen has good anticancer activity, and has entered phase two clinical trials as a drug for the treatment of prostate cancer (Wechter, W.J., et al. Cancer Res., 2000, 60(8), ...

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): C07C51/42C07C57/58
Inventor 谈忠兴蒋昌盛刘汉泉林国强
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com