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Preparing method for pirfenidone

A technology of pirfenidone and pentenenitrile, applied in the field of preparation of pirfenidone, can solve the problems of 2-amino-5-picoline high price, unsatisfactory yield, complicated operation, etc. Industrialized production application, reduced production cost, good effect of reaction selectivity

Active Publication Date: 2016-02-17
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The initial raw material 2-amino-5-picoline in this method has high price, complex operation and unsatisfactory yield (67-69.1%)

Method used

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  • Preparing method for pirfenidone
  • Preparing method for pirfenidone
  • Preparing method for pirfenidone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the preparation of pirfenidone (I)

[0033] In the 500 milliliter four-neck flask that is connected with stirring, thermometer and distillation device, add 150 grams of N,N-dimethylformamide, 24.3 grams (0.3 moles) of 2-pentenenitrile, 0.8 grams of toluenesulfonic acid, 42.5 g (0.4 mol) of trimethyl orthoformate was stirred and reacted at 90 to 100° C. for 4 hours, while recovering the produced methanol. Cool to 80 to 85°C, add 30.6 g (0.33 mole) of aniline, stir and react at 90 to 95°C for 3 hours, while recovering the produced methanol. Cool to 20°C, add 250 grams of water, stir at 20°C for 2 hours for hydrolysis reaction, the imino group is hydrolyzed to form a carbonyl group, and pirfenidone is generated; filter, and the filter cake is recrystallized with 200 grams of isopropanol to obtain 51.5 grams of white solid pirfenidone Nitone (I), the yield is 92.7%, and the liquid phase purity is 99.9%.

Embodiment 2

[0034] Embodiment 2: the preparation of pirfenidone (I)

[0035] In the 500 milliliter four-neck flask that is connected with stirring, thermometer and distillation device, add 150 grams of N,N-dimethylformamide, 24.3 grams (0.3 moles) of 2-pentenenitrile, 0.7 grams of toluenesulfonic acid, 59.5 g (0.4 mol) of triethyl orthoformate was reacted with stirring at 100 to 105° C. for 4 hours, and the ethanol produced was recovered at the same time. Cool to 80-85°C, add 30.5 g (0.33 moles) of aniline, raise the temperature to 100-105°C and stir for 3 hours, while recovering the ethanol produced. Cooled to 20°C, added 250 grams of water, hydrolyzed at 20°C for 2 hours, filtered, and the filter cake was recrystallized with 200 grams of isopropanol to obtain 52.0 grams of white solid pirfenidone (I), yield 93.6%, liquid phase 99.9% pure.

Embodiment 3

[0036] Embodiment 3: the preparation of pirfenidone (I)

[0037] In a 500 ml four-neck flask connected with a stirring, thermometer and distillation device, add 150 g of N,N-dimethylformamide, 24.3 g (0.3 moles) of 2-pentenenitrile, 0.6 g of 98% concentrated sulfuric acid, 42.0 gram (0.4 moles) of trimethyl orthoformate, reacted with stirring at 95 to 105° C. for 4 hours, and simultaneously recovered the produced methanol. Cool to 80 to 85°C, add 29.0 g (0.31 mole) of aniline, stir and react at 95 to 105°C for 3 hours, while recovering the produced methanol. Cool to 20°C, add 250 grams of water, stir and hydrolyze for 2 hours at 20°C, filter, and recrystallize the filter cake with 200 grams of isopropanol to obtain 51.0 grams of white solid pirfenidone (I), with a yield of 91.8%. Phase purity 99.9%.

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PUM

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Abstract

The invention relates to a preparing method for pirfenidone. The method includes the steps that under the action of an acid catalyst, 2-pentenenitrile is used for reacting with trimethyl / triethyl orthoformate to generate 2-methyl-1-alkoxy-4-cyano-1,3-butadiene (II), and 2-methyl-1-alkoxy-4-cyano-1,3-butadiene (II) and aniline are condensed and then hydrolyzed to obtain pirfenidone. The used raw materials are low in price and easy to obtain, the process flow is short, and the preparing method is easy to operate, environmentally friendly, high in reaction selectivity and high in product yield and purity.

Description

technical field [0001] The invention relates to a preparation method of pirfenidone, belonging to the technical field of anti-fibrosis drug synthesis. Background technique [0002] Pyridone compounds are a class of effective anti-fibrosis compounds, among which pirfenidone is a representative compound, which has a broad-spectrum anti-fibrosis effect and has a significant effect on the treatment of idiopathic pulmonary fibrosis. Fibrotic diseases, especially idiopathic pulmonary fibrosis (IPF) is a rare, progressive and fatal lung disease. decline. Pirfenidone, the chemical name is 5-methyl-1-phenyl-2(1H)-pyridone, the English name is Pirfenidone, and the domestic trade name is Aisirui. It is developed by the American Marnac company and has anti-fibrosis Functional compound, the structural formula is as follows: [0003] [0004] Pirfenidone was authorized by the European Medicines Agency for marketing in February 2008, and was approved by the US Food and Drug Administr...

Claims

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Application Information

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IPC IPC(8): C07D213/64
CPCC07D213/64
Inventor 戚聿新鞠立柱陈军李新发孟凡杰
Owner XINFA PHARMA
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