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Method for preparing prucalopride

An organic solvent, dihydrobenzene technology, applied in the field of medicinal chemistry, can solve the problems of unsuitability for industrial production, low yield, long reaction route and the like

Inactive Publication Date: 2014-02-12
BEIJING VENTUREPHARM BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The synthesis of compound 2 in route 1 has been reported in the literature, but the reaction route is long and the yield is not high. At the same time, the amino group on the benzene ring in compound 2 makes the reaction prone to side reactions, forming by-products, and the reaction yield is low.
The compound in route 2 is difficult to synthesize, and there are few literature reports, so it is not suitable for industrial production

Method used

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  • Method for preparing prucalopride
  • Method for preparing prucalopride
  • Method for preparing prucalopride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Dissolve 12.1 g of 4-nitro-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid in 50 mL of tetrahydrofuran, add 8.1 g of CDI, and add 1-(3-methoxypropyl )-4-Piperidine ammonia 8.6g, heated up to 80°C to react, TLC detected the reaction, cooled to room temperature after the reaction, added 200mL of water, solid washed out, filtered to obtain N-[1-(3-methoxypropane Base)-4-nitro-5-chloro-2,3-dihydrobenzofuran-7-carboxamide, the yield was 95%.

Embodiment 2

[0021] Dissolve 12.1 g of 4-nitro-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid in 50 mL of N,N-dimethylformamide, add 8.1 g of CDI, and add 1- (3-Methoxypropyl)-4-piperidinamine 8.6g, heated up to 80°C to react, TLC detected the reaction, cooled to room temperature after the reaction, added 200mL of water, solid washed out, filtered to obtain N-[ 1-(3-methoxypropyl)-4-nitro-5-chloro-2,3-dihydrobenzofuran-7-carboxamide, the yield was 85%.

Embodiment 3

[0023] Dissolve 12.1 g of 4-nitro-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid in 50 mL of dichloromethane, add 8.1 g of CDI, and add 1-(3-methoxy Propyl)-4-piperidinium 8.6g, react at room temperature, TLC detects the reaction, after the reaction is completed, cool to room temperature, add 200mL of water, there is solid washing out, filter to get N-[1-(3-methoxypropyl )-4-nitro-5-chloro-2,3-dihydrobenzofuran-7-carboxamide, the yield is 65%.

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Abstract

The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of prucalopride. Prucalopride succinate is a 5-HT4 receptor stimulant with high selectivity and specificity, and is a novel intestinal motility drug. The drug has the characteristics of high selectivity, rapid onset and less untoward effect, and has wide clinical application prospect in the field of constipation treatment. The invention provides a new method for compounding prucalopride, wherein 4-nitro-5-chlor-2,3-dihydrobenzofuran-7-methanoic acid and 1-(3-methoxypropyl)-4-piperidinamine are employed as initial materials to prepare prucalopride; and the preparation method is simple and convenient to operate, less in side reaction, high in yield, mild in reaction condition and convenient for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for preparing prucalopride. Background technique [0002] The chemical name of prucalopride succinate is: N-[1-(3-methoxypropyl)-4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxamide succinate, It is a benzofuran compound developed by Belgium Movetis NV company in 2009. It is a highly selective and specific 5-HT 4 Receptor agonist, a new type of intestinal motility drug, was launched in the UK in 2010. Prucalopride can stimulate intestinal peristaltic reflex, enhance colonic contraction, and effectively relieve constipation symptoms. Using prucalopride to treat severe chronic constipation can significantly improve intestinal function in a short period of time. Its structural formula is as follows: [0003] [0004] With the continuous development of the economy, the extreme deterioration of the living environment and the gradual acceleration of people...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12
CPCC07D405/12
Inventor 刘亚男闫起强马苏峰
Owner BEIJING VENTUREPHARM BIOTECH
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