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

Method for synthesizing prasugrel intermediate and method for synthesizing prasugrel

A synthetic method and intermediate technology, applied in the chemical and pharmaceutical fields, can solve the problems of high synthesis cost, reduced reaction efficiency, low yield, etc., and achieve the effect of convenient operation

Inactive Publication Date: 2009-09-16
SHANGHAI RECORD PHARM CO LTD
View PDF0 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route is relatively simple, but the yield of the key substitution linking the two fragments is too low (32%), resulting in a greatly reduced reaction efficiency, and thus the synthesis cost is too high

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 synthesizing prasugrel intermediate and method for synthesizing prasugrel
  • Method for synthesizing prasugrel intermediate and method for synthesizing prasugrel
  • Method for synthesizing prasugrel intermediate and method for synthesizing prasugrel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0026] The present invention is further illustrated by the following examples, but the scope of the present invention is not limited.

[0027] The first step: the synthesis of 1-cyclopropyl-2-(2-fluorophenyl)-2-(2-(thiophen-2-yl)ethylamine)ethanone, the reaction formula is:

[0028]

[0029] 2-Thienylethylamine (2.3g, 18.1mmol) was dissolved in 80ml of dichloromethane, potassium carbonate (2.5g, 18.1mmol) was added, and the 2 Slowly add 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (3.82g, 14.8mmol) in dichloromethane solution dropwise under protection. , washed with water (50ml×3), the organic layer was separated, dried with anhydrous sodium sulfate, suction filtered, and evaporated to dryness under reduced pressure. After separation by column chromatography, 3.14g of light yellow liquid was obtained, with a yield of 73%.

[0030] 1 H NMR (400MHz, CDCl 3 )δ: 0.72-1.08 (4H, m), 1.87 (1H, m), 2.75 (1H, m), 2.85 (1H, m), 3.00 (2H, m), 4.95 (1H, s), 6.79-7.30 (7H, m).ES...

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 belongs to the field of chemical engineering and pharmacy, and relates to a method for synthesizing a prasugrel intermediate and a method for synthesizing prasugrel. The method for synthesizing the prasugrel intermediate comprises that: 2-bromine-1-cyclopropyl-2-(2-fluorophenyl) ethyl ketone and 2-ethylamine thiophene are condensated under the action of alkali; then, after the reactant reacts with formaldehyde, 1-cyclopropyl-2-(6,7-dihydro-thieno[3,2-c]pyridine-5(4H)-yl)-2-(2-fluorophenyl) ketone after cycization of protonic acid. The method for synthesizing the prasugrel by the intermediate comprises that: after the intermediate 1-cyclopropyl-2-(6,7-dihydro-thieno[3,2-c]pyridine-5(4H)-yl)-2-(2-fluorophenyl)ketone is oxidized, the reactant is esterified with acetic anhydride to obtain the prasugrel. Synthesis of the prasugrel by the method can obtain products with high yield and simple operation steps.

Description

technical field [0001] The invention belongs to the field of chemical industry and pharmacy, and relates to a preparation process of a compound. More specifically, the invention relates to a synthesis method of a prasugrel intermediate, and a method for synthesizing prasugrel from the intermediate. Background technique [0002] Prasugrel (prasugrel) is an oral antiplatelet drug jointly developed by Eli Lilly and its partner Daiichi Pharmaceutical Sankyo, and has currently received priority approval from the FDA. Prasugrel is an oral platelet inhibitor, an anticoagulant drug. This product was originally developed for patients with acute coronary syndrome requiring percutaneous coronary intervention, including patients requiring stenting. If approved, this product will be sold under the trade name Efient in the United States. [0003] The existing synthetic route of prasugrel in the prior art is mainly the original synthetic route of Sankyo Company, with o-fluorobenzyl bromi...

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
IPC IPC(8): C07D495/04A61P7/02
Inventor 朱高军黄艳珍薛涛张芳江
Owner SHANGHAI RECORD PHARM 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