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Method for purifying etoricoxib

A technology of etoricoxib and purification method, applied in the field of raw material drug preparation, can solve the problems of high price and high production cost, and achieve the effects of simple operation and obvious purification effect

Inactive Publication Date: 2015-06-17
WEIHAI KANGBANGDE MEDICINE TECH DEVCO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] Compared with the above method, the reaction reagent used in this method is more expensive, and it also uses very expensive tetrakis(triphenylphosphine) palladium, the production cost is too high, and it is limited to laboratory applications

Method used

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  • Method for purifying etoricoxib
  • Method for purifying etoricoxib
  • Method for purifying etoricoxib

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Embodiment 1, In a 100L reactor, mix 5.6Kg compound I (21.6mol), 44.5Kg methanol, 0.45Kg 2N sulfuric acid, 0.13Kg sodium tungstate (dissolved in 4.0Kg water). Slowly raise the temperature to 45-55°C, keep it between 45-55°C, slowly add 13.2Kg hydrogen peroxide (30%) dropwise (about 3 hours to complete the dropwise addition), continue the heat preservation reaction for 1 hour after the dropwise addition, add 50Kg of water, slowly Cool down to -5°C and stir for 4 hours, filter with suction, and dry the filter cake in an oven at 70°C for 12 hours to obtain Compound II 5.8Kg, yield 92.6%, HPLC purity 94.16%, by-product III 5.02%.

Embodiment 2

[0042] Embodiment 2, In a 250mL three-neck flask, mix 23.0g of compound II (0.08mol) and 119mL of tetrahydrofuran, and keep warm at 0-5°C. 17.8 g potassium tert-butoxide (0.16 mol) was added and stirred for 1 hour. 56.5 g of compound IV (0.12 mol) was added to the reaction flask and stirred for 1 hour. The above reaction mixture was slowly added dropwise to a mixed system containing 38.2 g of acetic acid (0.64 mol) and 80 mL of tetrahydrofuran, and stirred for 2 hours. Add 47.7mL of ammonia water to the reaction flask, heat to reflux for about 5 hours, and concentrate. Then add 238mL of water, and extract the reaction mixture with 240mL of toluene. The liquid was separated, and the toluene phase was washed with 240 mL of saturated brine, and the toluene phase was evaporated to dryness under reduced pressure to obtain the crude etoricoxib as a viscous liquid. Dissolve the viscous liquid in 240 mL of methanol, add 0.18 g of lithium borohydride, stir for 0.5 hour, evaporate ...

Embodiment 3

[0043] Embodiment 3,In a 1000mL three-neck flask, mix 52.1g of compound II (0.18mol) and 450mL of tetrahydrofuran, and keep warm at 0-5°C. Add 40.3 g of potassium t-butoxide (0.36 mol) and stir for 1 hour. 82.6 g of compound IV (0.27 mol) was added to the reaction kettle and stirred for 1 hour. The above reaction mixture was slowly added dropwise to a mixed system containing 97.2 g of acetic acid (1.62 mol) and 180 mL of tetrahydrofuran, and stirred for 2 hours. Add 109.3 g of ammonia water to the reaction flask, heat to reflux for about 5 hours, and concentrate. 540 mL of water was added, and the reaction mixture was extracted with 540 mL of toluene. The liquid was separated, the toluene phase was washed with 540 mL of saturated saline, and the toluene phase was evaporated to dryness under reduced pressure to obtain the crude etoricoxib as a viscous liquid. Dissolve the viscous liquid in 360 mL of ethanol, add 1.0 g of sodium borohydride, stir for 0.5 hours, evaporate th...

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Abstract

The invention relates to a method for purifying etoricoxib, which belongs to the technical field of bulk drug preparation. A preparation method for etoricoxib is divided into six steps, a compound in a formula I is used for synthesizing etoricoxib through a step 1 and a step 2, and then step 3- step 6 are carried out to remove impurities. The method is suitable for industrial production, operation is simple, and purifying effect is obvious. The HPLC purity of the final product can reach more than 99.8%, and single impurity is less than 0.1%.

Description

technical field [0001] The invention relates to a method for purifying crude etoricoxib, and belongs to the technical field of preparation of crude drugs. Background technique [0002] Etoricoxib is a new type of non-steroidal anti-inflammatory drug developed by Merck. Road reaction light and other advantages. For the treatment of osteoarthritis (OA), rheumatoid arthritis and acute gouty arthritis, etc. The drug was first launched in Mexico in September 2001 and in the United States in 2002. [0003] The synthesis of prior art etoricoxib has the following several methods: [0004] One is the ring-forming method, which has the following two methods. [0005] method one [0006] [0007] U.S. Patent No. 6,369,275 pointed out that this method is prone to side reactions, requires anhydrous and oxygen-free reaction conditions, and has strict process requirements, which is not suitable for industrial production. [0008] Method Two [0009] Patent WO2013 / 105106 discloses...

Claims

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Application Information

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IPC IPC(8): C07D213/61
CPCC07D213/61
Inventor 杨修东卞常鑫吴荣贵穆孟亮
Owner WEIHAI KANGBANGDE MEDICINE TECH DEVCO
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