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

Method for preparing thiazolidine acetate coprising phenyl propylidene

A technology of thiazolidine acetic acid and phenylpropenylidene is applied in the preparation field containing phenylpropenylidene thiazolidine acetic acid, and can solve the problems of low reaction yield, complicated post-processing, difficulty in recovery and application, etc.

Inactive Publication Date: 2006-03-08
YANGTZE RIVER PHARM GRP CO LTD
View PDF0 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent J.P.62-51955, U.S.4.464.382, E.P.0 047109 discloses 5-[(1Z,2E)-2-methyl-3-phenylpropenylidene]-4-oxo-2-thioxo-3-thiazole The synthesis method of alkane acetic acid, the synthesis of rhodanine acetic acid adopts glycine to form sodium salt first, and then uses dioxane as a solvent to condense with excess ammonia water. The intermediate is not separated, and directly reacts with sodium chloroacetate to form rhodanine acetic acid, dioxane It is difficult to recycle and apply mechanically after ring-adding ammonia water, and the post-treatment is complicated
Condensation of α-methylcinnamaldehyde (1) with rhodanine acetic acid (4) generates 5-[(1Z,2E)-2-methyl-3-phenylpropenylidene]-4-oxo-2-thio- In 3-thiazolidineacetic acid compound (5), the reaction yield is very low

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
  • Method for preparing thiazolidine acetate coprising phenyl propylidene
  • Method for preparing thiazolidine acetate coprising phenyl propylidene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0011] Synthesis of α-Methylcinnamaldehyde 1

[0012] Dissolve 26.1g NaOH in 285ml water, stir to dissolve, add 135.3g benzaldehyde, add 37g propionaldehyde dropwise at below 50°C, after the addition is complete, continue to stir and react for 2 hours. After the reaction, separate the oil layer, distill under reduced pressure, and recover For benzaldehyde, the fraction with bp of 120-124°C / 9-13mmHg is collected, and the yield is about 80% for propionaldehyde.

[0013] Rhodanine acetic acid is the synthesis of compound 4:

[0014] a. Dissolve 40g of glycine in a mixture of 33ml of water and 100ml of ammonia water, add 35ml of carbon disulfide dropwise at a temperature below 10°C, react at room temperature for 2 hours, add 150ml of ethanol to crystallize, filter, rinse with ethanol and dry to obtain the disulfide compound 2 .

[0015] b. Add 57.5g of chloroacetic acid, 32.5g of sodium carbonate and 144ml of water into a 500ml three-necked flask, add all of the above-mentioned ...

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

This invention relates to a preparation method for a diabetes-curing medicine 5-[(1Z, 2E)-2-methyl-3-benzyl ethylene tine]-4-oxy-2-sulfo-3-thiazolidine acetic acid, with benzaldehyde as raw material. Add alpha-methyl cinnamaldehyde (1), rhodanine acetic acid compound (4) and ammonia water in mol ratio of 1: 0.1~5: 1~5 into polar solvent, then react for 1~ 24h under 0~100 deg.C, and finally the 5-[(1Z, 2E)-2-methyl-3-benzyl ethylene tine]-4-oxy-2-sulpho-3-thiazolidine acetic acid is acquired. In this method, as adding the reagent ammonia water, the yield is considerably raised.

Description

technical field [0001] The invention relates to a method for preparing a medicine for treating diabetes from benzaldehyde, that is, a preparation method containing phenylacrylidene thiazolidine acetic acid. Background technique [0002] A kind of phenylacrylidene thiazolidine acetic acid, namely 5-[(1Z, 2E)-2-methyl-3-phenylpropenylidene]-4-oxo-2-thio-3-thiazolidine acetic acid (English name Epalrestat, Chinese name: Epalrestat) is a new type of drug for the treatment of diabetes, which blocks the glucose metabolism "sorbitol pathway" by inhibiting the activity of aldose reductase (AR). The curative effect is definite, the side effect is small, and the effect is rapid. The results of clinical trials show that the blood concentration of epalrestat 50-200mg is positively correlated with the dose. Drug distribution is mainly in the kidney and liver, but hardly distributed in the brain and reproductive organs. This product does not pass through the placenta and is rarely dist...

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): C07D277/36A61P3/10
Inventor 孙海盛张玉斌杨成刘栋王耀兵游明霞
Owner YANGTZE RIVER PHARM GRP CO LTD
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