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Purification method of abiraterone acetate

A technology of abiraterone acetate and a purification method, which is applied in the field of purification of raw material drug abiraterone acetate, can solve the problems of unfavorable scale-up production, easy residual impurities, difficult filtration, etc., and achieve easy operation, simplified purification process, and reagent saving Effect

Inactive Publication Date: 2011-04-27
深圳万乐药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] However, there are disadvantages in the purification method of this process, that is, when methanesulfonic acid and abiraterone acetate are salified, a thick suspension is formed, which is difficult to filter. Abiraterone mesylate needs to be recrystallized and purified and then freed with alkali to obtain abiraterone acetate, which increases the operation time and difficulty, and is not conducive to industrial scale-up production

Method used

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  • Purification method of abiraterone acetate
  • Purification method of abiraterone acetate
  • Purification method of abiraterone acetate

Examples

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Effect test

Embodiment 1

[0021] Embodiment 1 Preparation of Abiraterone Acetate Crude Product

[0022] Add 100 g of dehydroepiandrosterone acetate to 1 L of dichloromethane, add 56 mL of trifluoromethanesulfonic acid under stirring, and stir the solution at room temperature for 5 minutes, then add 33.1 g of 2,6-lutidine within 25 minutes. 1L dichloromethane solution, and stirred at room temperature for 3.5 hours, after adding 1.5L water to quench the reaction, layered separation, the aqueous phase was extracted with 750mL dichloromethane, the organic phases were combined, and washed with 750mL 2N HCl solution, layered separation, Anhydrous Na 2 SO 4 After drying and treating the organic phase with 70 g of activated carbon for 10 minutes, suction filtration, the filtrate was concentrated under reduced pressure to obtain 127.5 g of brown oil;

[0023] After dissolving 127.5g of brown oil in 1.3L of tetrahydrofuran (THF), 0.97g of Pd(PPh 3 ) 2 Cl 2 , 61.1 g diethyl (3-pyridyl) borane and 550 mL 2M N...

Embodiment 2

[0024] Embodiment 2 Purification of Abiraterone acetate crude product (trifluoromethanesulfonic acid is a salt-forming reagent)

[0025] Add 82.75g of abiraterone acetate crude oil to 250mL of ethyl acetate to completely dissolve it, then add it to a 1L three-necked flask, then add 250mL of methyl tert-butyl ether, stir and cool the mixture to -5~5°C, then add dropwise 21.35g of trifluoromethanesulfonic acid, after dripping, stirred at -5~5℃ for 1 hour, removed the ice bath, warmed up to room temperature, stirred at constant temperature for 2 hours, filtered with suction, and dried the filter cake to obtain 45.3g of off-white particles of albino acetate Biterone trifluoromethanesulfonate (HPLC purity 97.05%, only 1 impurity with content > 1%), yield 54.74%;

[0026] The above-mentioned abiraterone acetate trifluoromethanesulfonate was added to a 1L three-neck flask, and then 250mL of dichloromethane and 250mL of 20% Na 2 CO 3 Aqueous solution, after stirring for 20 minutes, ...

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Abstract

The invention provides a purification method of abiraterone acetate. The method comprises the following steps of: reacting trifloromethanesulfonic acid serving as a salt forming reagent with crude abiraterone acetate to obtain dry and easily-purified abiraterone acetate trifluoromethanesulfonic salt with the purity of over 97 percent; and performing a free reaction on the abiraterone acetate trifluoromethanesulfonic salt without a purification step so as to obtain abiraterone acetate, wherein the purity of the abiraterone acetate obtained by the free reaction is over 97 percent. The method simplifies purification process, saves reagent and is easy to operate and suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, and further relates to a method for purifying a raw drug abiraterone acetate. Background technique [0002] Male hormones such as testosterone, which are produced primarily in the testes but also in the adrenal glands and elsewhere in the body, can stimulate the growth of prostate cancer. Abiraterone acetate was invented by researchers at the Royal Marsden Hospital (a world-renowned cancer research and treatment center) in southwest London. The drug is the key enzyme 17α-hydroxylase in the synthesis of androgen - C17,, 2-lyase (also called steroid) 17α-monooxygenase inhibitor or human cytochrome P450 17α An effective and selective oral inhibitor that reduces androgen levels by inhibiting the key enzyme in androgen synthesis - CYP450c17, and has inhibitory effects on androgen in the testis and other parts of the body. Abiraterone acetate has been shown to suppress androgen in prostate cancer p...

Claims

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Application Information

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IPC IPC(8): C07J43/00
Inventor 钱建彬朱勇秦怀伟李瑞远尹志媛张广明
Owner 深圳万乐药业有限公司
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