Preparation method for celecoxib

A technology of celecoxib and cyclization reaction, which is applied in the direction of organic chemistry, can solve the problems of poor quality, and achieve the effect of good quality, less waste, and high purity

Inactive Publication Date: 2013-05-15
HENAN DONGTAI PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Although the yield is slightly

Method used

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  • Preparation method for celecoxib

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Embodiment 1

[0014] Example 1: Preparation of 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione

[0015] Add 160 ml of methyl tert-butyl ether and 6.48 g (0.12 mol) of sodium methoxide to a 250 ml three-necked flask, and add 42.4 g (0.3 mol) of ethyl trifluoroacetate at a temperature of 25°C. Stir for 10 minutes. 13.4 g (0.3 mol) of p-methylacetophenone was slowly added dropwise, and the dropwise addition was completed in about 30 minutes. The temperature was raised to reflux for 12 hours and the reaction was completed. The solvent was distilled off under reduced pressure first under normal pressure to obtain a light yellow oily substance. Neutralize to PH4-5 with 10% hydrochloric acid. Extract three times with 20 ml of methyl tert-butyl ether, and combine the organic layers. The solvent was evaporated, and the crystals were left to stand to obtain 22.5 g of 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione crystals, with a yield of 98.0%.

Embodiment 2

[0016] Example 2: Preparation of 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione

[0017] Add 160 ml of methyl tert-butyl ether and 10.2 g (0.15 mol) of sodium ethoxide to a 250 ml three-necked flask, and add 42.4 g (0.3 mol) of ethyl trifluoroacetate at a temperature of 25°C. Stir for 10 minutes. 13.4 g (0.3 mol) of p-methylacetophenone was slowly added dropwise, and the dropwise addition was completed in about 30 minutes. The temperature was raised to reflux for 12 hours and the reaction was completed. The solvent was distilled off under reduced pressure first under normal pressure to obtain a light yellow oily substance. Neutralize to PH4-5 with 10% hydrochloric acid. Extract three times with 20 ml of methyl tert-butyl ether, and combine the organic layers. The solvent was evaporated, and the crystals were left to stand to obtain 22.8 g of 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione crystals, with a yield of 99.1%.

Embodiment 3

[0018] Example 3: Preparation of 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione

[0019] Add 160 ml of methyl ethyl ether and 15.36 g (0.16 mol) of sodium tert-butoxide to a 250 ml three-necked flask, and add 42.4 g (0.3 mol) of ethyl trifluoroacetate at a temperature of 25°C. Stir for 10 minutes. 13.4 g (0.3 mol) of p-methylacetophenone was slowly added dropwise, and the dropwise addition was completed in about 30 minutes. The temperature was raised to reflux for 12 hours and the reaction was completed. The solvent was distilled off under reduced pressure first under normal pressure to obtain a light yellow oily substance. Neutralize to PH4-5 with 10% hydrochloric acid. Extract three times with 20ml of methyl ethyl ether, and combine the organic layers. The solvent was evaporated, and the crystals were left to stand to obtain 22.7 g of 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione crystals, with a yield of 98.5%.

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Abstract

The invention relates to a preparation method for celecoxib, and belongs to the field of chemical pharmaceuticals. The method comprises the step of performing cyclization reaction on 4, 4, 4-trifloro-1-(4-tolyl)-1, 3-butanedione and p-sulfamine phenylhydrazine or 4-sulfamine phenylhydrazine hydrochloride in a solvent to obtain a celecoxib coarse product, wherein the solvent for cyclization reaction is a low molecular organic acid or a low molecular organic acid aqueous liquor. According to the method, the product is high in yield, good in purity, easy to purity, good in quality and low in cost; and the method is environment-friendly in condensation process, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of a non-steroidal anti-inflammatory drug, in particular to a preparation method of celecoxib, which belongs to the field of chemical pharmacy. Background technique [0002] Traditional non-steroidal anti-inflammatory drugs, such as aspirin, ibuprofen, diclofenac sodium, and indomethacin, inhibit cyclooxygenase-II (COX-2) while inhibiting cyclooxygenase-1 (COS-1). There are also undesirable inhibitory effects, resulting in gastrointestinal side effects and even severe digestive tract damage. The COX-2 inhibitors represented by celecoxib are a new generation of non-steroidal anti-inflammatory drugs, which can selectively inhibit COX-2 and have no obvious inhibitory effect on COX-1. It has significant anti-inflammatory, antipyretic and analgesic effects, but does not cause digestive tract damage. It is an excellent anti-inflammatory analgesic drug. It has been reported that celecoxib also has preventive an...

Claims

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Application Information

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IPC IPC(8): C07D231/12
Inventor 苗青刘发光刘康宋晓星李志江李恒远
Owner HENAN DONGTAI PHARM
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