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Preparation and purification method of deferacoxib

A technology of diracoxib and a purification method, applied in the direction of organic chemistry and the like, can solve the problems of low product yield and low purity, and achieve the effects of high product purity, simplified purification steps and simple operation.

Active Publication Date: 2022-04-08
JIANGSU TIANHE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Purpose of the invention: In order to solve the technical problems of low product yield and low purity in the existing preparation methods, the present invention provides a method for preparing and purifying deracoxib. The process of the present invention is more conducive to industrial production, reduces production costs, and improves Product yield and quality

Method used

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  • Preparation and purification method of deferacoxib
  • Preparation and purification method of deferacoxib
  • Preparation and purification method of deferacoxib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of deracoxib

[0042] S1: Add 180g of 30% sodium methoxide methanol solution to a 1L reaction flask, add 300g of methyl tert-butyl ether, add 30g of 3-fluoro-4-methoxyacetophenone, 31g of ethyl difluoroacetate, and heat up to 50°C After stirring for 5 hours, the solution was distilled to dryness. Add 100mL of water and 21g of 30% hydrochloric acid solution; add 43.9g of 4-sulfonylaminophenylhydrazine hydrochloride and 90mL of ethanol, heat up at 80-85°C and reflux for 5 hours, cool to 5°C, filter with 20mL The filter cake was rinsed with ethanol, and dried to obtain 68.5 g of crude product of deracoxib.

[0043] S2: Purification of crude deracoxib: Add 68.5 g of crude deracoxib and 340 g of water into a 1L reaction bottle, heat to 90°C, add 30% aqueous sodium hydroxide solution dropwise, and adjust the pH to 12-13. Cool the reaction solution to 20-30°C, and filter with suction to obtain deracoxib sodium salt.

[0044] S3: Put the deracox...

Embodiment 2

[0045] Embodiment 2: the preparation of deracoxib

[0046] Add 300g of 30% sodium methoxide methanol solution to a 2L reaction flask, add 540g of methyl tert-butyl ether, add 60g of 3-fluoro-4-methoxyacetophenone, 57.5g of ethyl difluoroacetate, heat up to 50°C and stir After 5 hours, the solution was distilled to dryness. Add 200mL of water and 42g of 30% hydrochloric acid solution; add 85g of 4-sulfonylaminophenylhydrazine hydrochloride and 200ml of ethanol, heat up at 80-85°C and reflux for 5 hours, cool down to 5°C, filter with suction, and use 40mL of ethanol The filter cake was rinsed and dried to obtain 138.2g crude product of deracoxib.

[0047]Add 138.2 g of crude deracoxib and 552.8 g of water into a 1 L reaction bottle, heat to 90°C, add dropwise 30% aqueous sodium hydroxide solution, and adjust the pH to 12-13. Cool the reaction solution to 20-30°C, and filter with suction to obtain deracoxib sodium salt.

[0048] Put deracoxib sodium salt into a 1L reaction bot...

Embodiment 3

[0049] Embodiment 3: the preparation of deracoxib

[0050] Add 15kg of 30% sodium methoxide methanol solution into a 100L reactor, add 24g of methyl tert-butyl ether, add 3kg of 3-fluoro-4-methoxyacetophenone, 2.7kg of ethyl difluoroacetate, heat up to 50°C and stir After 6 hours, the solution was distilled to dryness. Add 10L of water and 2.1kg of 30% hydrochloric acid solution; add 4.2kg of 4-sulfonylaminophenylhydrazine hydrochloride and 9L of ethanol, heat up at 80-85°C and reflux for 6 hours, cool down to 5°C, filter with The filter cake was rinsed with 2 L of ethanol, and dried to obtain 6.95 kg of crude product of deracoxib.

[0051] Add 6.95kg of crude deracoxib and 35kg of water into a 100L reaction kettle, heat to 90°C, add 30% aqueous sodium hydroxide solution dropwise, and adjust the pH to 12-13. Cool the reaction solution to 20-30°C, and filter with suction to obtain deracoxib sodium salt.

[0052] Put deracoxib sodium salt into a 100L reaction kettle, add 35kg...

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Abstract

The invention discloses a preparation and purification method of deferacoxib. According to the present invention, the delaricoxib crude product is synthesized by using the 3-fluoro-4-methoxyacetophenone, the ethyl difluoroacetate, the sodium methoxide, the methyl tert-butyl ether, the 4-sulfonylamino phenylhydrazine hydrochloride and the ethanol through the one-pot method, such that the operation process is reduced, and the reaction time is shortened; according to the invention, the obtained delaricoxib crude product is subjected to acid-base refining to obtain the delaricoxib finished product, and the high-purity delaricoxib finished product is prepared.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a preparation and purification method of deracoxib. Background technique [0002] Deracoxib is a new type of non-steroidal anti-inflammatory drug, which belongs to the cyclooxygenase-2 (COX-2) inhibitor, and is used to relieve pain and anti-inflammation caused by dog ​​surgery and osteoarthritis. It is currently the first A non-steroidal anti-inflammatory drug of the COX-2 inhibitor class for use in animals. At present, the patent CN107686465 optimizes the solvent for the preparation of deracoxib. Contents of the invention [0003] Purpose of the invention: In order to solve the technical problems of low product yield and low purity in the existing preparation methods, the present invention provides a method for preparing and purifying deracoxib. The process of the present invention is more conducive to industrial production, reduces production costs, and improves Product yi...

Claims

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Application Information

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IPC IPC(8): C07D231/12
Inventor 张来平薛晨张嫚赵志美李庚草
Owner JIANGSU TIANHE PHARMA CO LTD
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