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Etoricoxib purification and preparation method

A technology of etoricoxib and purification method, applied in the field of medicinal chemistry, can solve the problems of low purity, many impurities, difficult to remove, etc., and achieve the effect of improving product purity

Active Publication Date: 2019-04-05
CHINA RESOURCES DOUBLE CRANE PHARMA COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The product obtained by this method has low purity, is not easy to crystallize, and has many impurities, especially the impurity M, whose content is greater than 0.1%. Because its physical and chemical properties are similar to the raw materials, it is not easy to remove, and it needs to be refined many times to control the limit at 0.1%. Below, the yield loss is greater

Method used

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  • Etoricoxib purification and preparation method
  • Etoricoxib purification and preparation method
  • Etoricoxib purification and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] 1) Preparation of etoricoxib (compound AYTKX05)

[0138] 1.1) Add compound AYTKX17 (800.0g, 3.109mol), methanol (7200ml) and sodium tungstate (20.51g, 0.062mol) to a 20L reactor, stir to obtain a yellow suspension, and slowly add 10% hydrogen peroxide ( 2325.9g, 6.840mol), control the temperature below 50°C, after the dropwise addition, control the temperature between 40-50°C for 2h, TLC shows that the reaction is basically complete, add sodium sulfite (78.4g, 0.622mol) solution dissolved in 800ml of water , stirred for 20 minutes, then lowered the temperature to 5-10°C and stirred for 1 hour, filtered with suction, washed the filter cake with 500ml of purified water × 2, and dried to constant weight at 45-55°C to obtain 827.1g of light yellow solid with a yield of 92.0% . Add the light yellow solid (825.0g) obtained in step 1.1) into a 10L three-necked flask, add acetonitrile (3300ml) and purified water (2475ml), heat up to reflux and stir for 0.5h, the solution is a ...

Embodiment 2

[0146] 1) Preparation of etoricoxib (compound AYTKX05)

[0147] 1.1) Add compound AYTKX17 (20.0g, 77.72mmol), 180ml methanol and sodium tungstate (0.51g, 1.55mmol) into a 500mL reaction kettle, stir to obtain a yellow suspension, slowly dropwise add 30% hydrogen peroxide (26.44g, 233.15mol), control the temperature below 60°C, and control the temperature between 55-60°C for 1h after the dropwise addition, TLC shows that the reaction is basically complete, lower the temperature to 5-10°C and stir for 1h, filter with suction, and filter the cake with purified water 30ml×2 washes, air-dried at 45-55°C to constant weight to obtain 17.5g light yellow solid. Add the obtained light yellow solid (17.5g) into a 500mL three-necked flask, add acetonitrile (106ml) and purified water (210ml), heat up to reflux and stir for 0.5h, the solution is a suspension, cool down and crystallize, and control the temperature for 5-10 Stir at ℃ for 1 hour, filter with suction, wash the filter cake with...

Embodiment 3

[0153] 1) Preparation of etoricoxib (compound AYTKX05)

[0154] 1.1) Add AYTKX17 (20.0g, 77.72mmol), 200ml methanol and sodium tungstate (0.51g, 1.55mmol) into a 500mL reaction kettle, stir to obtain a yellow suspension, slowly add 30% hydrogen peroxide (26.44g, 233.15 mol), control the temperature below 60°C, after the dropwise addition, control the temperature between 55-60°C and react for 2h, TLC shows that the reaction is basically complete, lower the temperature to 5-10°C and stir for 1h, filter with suction, filter cake with purified water 30ml× 2 washing, air-drying at 45-55° C. to constant weight to obtain 19.22 g of a light yellow solid with a yield of 85.46%. Add the obtained pale yellow solid (18.5g) into a 500mL three-necked flask, add acetonitrile (130ml) and purified water (220ml), heat up to reflux and stir for 0.5h, the solution is a suspension, cool down and crystallize, and control the temperature for 5-10 Stir at ℃ for 1 h, filter with suction, wash the fil...

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Abstract

The invention relates to an etoricoxib purification method which includes the operation: performing reduction reaction on etoricoxib crude drugs to be purified and reduction agents in solvents. The invention further relates to a method for preparing etoricoxib. The purity of the finished etoricoxib prepared by the preparation method is higher than 99.9%, the total content of an impurity F, an impurity 20 and an impurity 21 is lower than 0.001%, and no impurity M is detected.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for purifying etoricoxib, and also relates to a method for preparing etoricoxib. Background technique [0002] Etoricoxib (etoricoxib) is a highly selective cyclooxygenase-2 (COX-2) inhibitor with anti-inflammatory, analgesic and antipyretic effects. It is developed and produced by Merck and has been sold in 84 countries around the world. and regional listings. Etoricoxib exerts antipyretic, analgesic and anti-inflammatory effects by inhibiting COX-2 and reducing the production of prostaglandins and thromboxanes. It has the advantages of quick onset, strong analgesia, long half-life, and mild gastrointestinal reactions. Traditional non-steroidal anti-inflammatory drugs (NSAIDs) have been improved, and at the same time can reduce the incidence of adverse reactions such as gastrointestinal tract, and are proven effective coxibs for the treatment of acute gou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 何阳李涛涛许俊博谢红
Owner CHINA RESOURCES DOUBLE CRANE PHARMA COMPANY
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