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Abiraterone acetate trifluoroacetate, and preparation method and application thereof

A technology of abiraterone acetate and trifluoroacetate, applied in carboxylate preparation, steroids, organic chemistry, etc., can solve the problems of low product purity and yield, unfavorable large-scale production, and many impurities. Achieve the effects of stable quality, simple operation of salt formation and purification, and high yield

Active Publication Date: 2013-08-21
SHANGHAI ACEBRIGHT PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In summary, it can be seen that the existing methods for purifying abiraterone acetate all have the following disadvantages: product purity and yield are low; impurities are many and the content is high; the final product form obtained is oily; it needs to pass through the column layer Analysis and purification methods are required to obtain products that meet pharmaceutical standards; the cost is high and it is not conducive to large-scale production

Method used

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  • Abiraterone acetate trifluoroacetate, and preparation method and application thereof
  • Abiraterone acetate trifluoroacetate, and preparation method and application thereof
  • Abiraterone acetate trifluoroacetate, and preparation method and application thereof

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Embodiment 1

[0033] Embodiment 1: Preparation of abiraterone acetate trifluoroacetate

[0034] ① Preparation of Abiraterone Acetate Crude Product

[0035] a) Add 33g of dehydroepiandrosterone acetate into a dry 1L four-necked bottle, vacuumize and protect with argon; add 400ml of dichloromethane, stir to dissolve; control the temperature at 0-30°C, and add trifluoromethanesulfonic anhydride dropwise 23.5ml, the dropwise addition time is 10-20 minutes, after the dropwise addition, the internal temperature is 0-30°C and stirred for 10 minutes; dropwise add 200ml of dichloromethane solution containing triethylamine, the temperature is kept at 0-30°C, the dropwise addition time 35 to 40 minutes; after the dropwise addition, stir at an internal temperature of 0 to 30°C for 1 hour, and perform thin layer chromatography (monitored by TLC); add 250ml of ice water dropwise to stop the reaction, then add 250ml of dichloromethane, separate and collect The dichloromethane layer and the water layer we...

Embodiment 2

[0041] Embodiment 2: be used for purifying abiraterone acetate

[0042] a) Transfer the above-mentioned 28.1g of abiraterone acetate trifluoroacetate to a 500ml single-necked bottle, add 300ml of isopropanol, heat to reflux, cool down to room temperature after dissolving, filter with suction, and wash the filter cake with a small amount of ice isopropanol , drying the filter cake to obtain 21.66g light yellow solid, which is purified abiraterone acetate trifluoroacetate, and the mass yield is 77.1%;

[0043] b) Add 21.66 g of the light yellow solid obtained in 200 ml of dichloromethane, stir to make it substantially dissolved, then add an aqueous solution of sodium carbonate with a mass percent concentration of 20%, control the pH of the aqueous phase>10, then stir at room temperature for 1 hour, Separation, the aqueous layer was extracted twice with 100ml dichloromethane, the dichloromethane layers were combined, dried over anhydrous sodium sulfate, suction filtered and conce...

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Abstract

The invention discloses abiraterone acetate trifluoroacetate, and a preparation method and an application thereof. The trifluoroacetate is obtained by a salt formation reaction of abiraterone acetate and trifluoroacetic acid. The abiraterone acetate trifluoroacetate provided by the invention is solid, and can be subjected to self purification through re-crystallization. Medical-standard abiraterone acetate with purity higher than 99.5% and single impurity lower than 0.1% can be easily obtained by ionizing and re-crystallizing the purified abiraterone acetate trifluoroacetate. With the method provided by the invention, a defect of the requirement on abiraterone acetate column chromatography purification of prior art is solved, and the salt formation reagent is cheap. Salt formation and purification operations are simple and feasible, yield is high, and quality is stable. The purpose for producing high-purity abiraterone acetate with low cost and simple process is realized, and abiraterone acetate large-scale production requirement can be satisfied.

Description

technical field [0001] The invention relates to abiraterone acetate trifluoroacetate and a preparation method and application thereof, belonging to the technical field of organic chemistry. Background technique [0002] Abiraterone acetate (ZYTIGA) is converted into abiraterone in the body. Abiraterone is an oral inhibitor of cytochrome oxidase P450 (CYP450)c17, which inhibits androgen synthesis by inhibiting the enzyme CYP450c17, which is the testis A key enzyme in the synthesis of hormones in other parts of the body. On April 28, 2011, the U.S. Food and Drug Administration (FDA) approved abiraterone acetate (Abiraterone acetate, Zytiga) combined with prednisone (prednisone, steroids) in the treatment of advanced (metastatic) Surgical removal of refractory prostate cancer treated with cetaxel (chemotherapy). The chemical structural formula of Abiraterone acetate is as follows: [0003] [0004] WO9320097A first reported the compound and its synthetic method, using deh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00C07C53/18C07C51/41
CPCC07J43/00C07J43/003C07C53/10
Inventor 安晓霞毛锋旺黄成军
Owner SHANGHAI ACEBRIGHT PHARMA CO LTD
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