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Purification method of abiraterone

A technology of abiraterone and purification method, which is applied in the fields of organic chemistry and steroids, and can solve the problems of high cost, time-consuming, complicated operation, etc.

Inactive Publication Date: 2012-12-12
成都伊诺达博医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the purification of abiraterone involved in this route requires column chromatography, which is complicated to operate, time-consuming and high in cost, which will become a bottleneck restricting the large-scale production of abiraterone acetate

Method used

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  • Purification method of abiraterone

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Preparation of 17-(3-pyridyl)androst-5,16-dien-3beta-ol (abiraterone)

[0031] Add 750ml of THF to a 3L three-necked flask, and add 50g of 17-iodo-androst-5,16-dien-3beta-ol, 264mg of bistriphenylphosphinepalladium chloride and 16.44g of pyridine-3-di Ethylborane, finally add 345ml 2mol / L Na 2 CO 3 solution. Heat to reflux, control the internal temperature at 85-90°C, and monitor the completion of the reaction by TLC. Cool the reaction solution to room temperature, add 1500ml of water to the reaction solution, stir for solid precipitation, stir for 30min, and filter. The filter cake was stirred and washed 4 times with water. The filter cake was air-dried overnight at 50-55° C. to obtain 26.3 g of crude abiraterone.

Embodiment 2

[0033] Purification of 17-(3-pyridyl)androst-5,16-dien-3beta-ol (abiraterone)

[0034] Add 34.9g of Abiraterone to 350ml of THF at room temperature, and stir until dissolved. Under an ice bath, cool to 0-5°C, add 4.9g of concentrated sulfuric acid dropwise, and control the internal temperature not to exceed 10°C. After the dropwise addition, continue to stir in an ice bath for 30 min, filter, stir and wash with pre-cooled THF (50ml×2), and drain to obtain the crude abiraterone sulfate. Add the obtained abiraterone sulfate to 200ml of ethanol / water (4:1) mixed solvent, heat to reflux to dissolve, slowly cool to room temperature, add ice bath, and stir for 2h. Filter and wash with pre-cooled ethanol (40ml×2). After draining, dissolve the solid in 100ml of water, add 40% NaOH solution dropwise under ice bath, and adjust the pH to 8-9. Filter and wash with pure water (40ml×2). Blow drying at 50-60°C to obtain 32.8g of abiraterone, HPLC: 99.6%, single impurity <0.1%.

Embodiment 3

[0036] Purification of 17-(3-pyridyl)androst-5,16-dien-3beta-ol (abiraterone)

[0037] Add 34.9g of Abiraterone to 350ml of THF at room temperature, and stir until dissolved. Under an ice bath, cool to 0-5°C, add 11.4g of trifluoroacetic acid dropwise, and control the internal temperature not to exceed 10°C. After the dropwise addition was completed, continue to stir in an ice bath for 30 minutes, filter, stir and wash with pre-cooled THF (50ml×2), and drain to obtain the crude product of abiraterone trifluoroacetate. Add the obtained abiraterone trifluoroacetate into 200ml of ethanol / water (4:1) mixed solvent, heat to reflux to dissolve, slowly cool to room temperature, add ice bath, and stir for 2h. Filter and wash with pre-cooled ethanol (40ml×2). After draining, dissolve the solid in 100ml of water, add 40% NaOH solution dropwise under ice bath, and adjust the pH to 8-9. Filter and wash with pure water (40ml×2). Blow drying at 50-60°C to obtain 33.1 g of abiraterone, H...

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Abstract

The invention discloses a purification method of abiraterone. The method comprises the following steps: salifying an abiraterone crude product and acid, recrystallizing in an appropriate solvent, and adding alkali for ionization to obtain the abiraterone pure product, of which the HPLC (high performance liquid chromatography) purity is higher than 99.5% and the single impurity content is less than 0.1%. The invention has the advantages of simple technique and high crystallization yield, and is easy to control.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis technology, and in particular relates to a purification method of abiraterone. Background technique [0002] Prostate cancer is a malignant tumor that occurs in male prostate tissue and is the result of abnormal and disordered growth of prostate acinar cells. Prostate cancer incidence varies markedly by geographic and ethnic origin. In developed countries and regions such as Europe and the United States, it is the most common malignant tumor in men, and its mortality rate ranks second among various cancers; in Asia, its incidence rate is lower than that in Western countries, but it has shown a rapid upward trend in recent years. Studies have found that the male hormone testosterone can stimulate the growth of prostate tumors, so clinical treatment generally uses drugs or surgery to reduce the production of testosterone or block the effect of testosterone. But it has been clinica...

Claims

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Application Information

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IPC IPC(8): C07J43/00
Inventor 付清泉岳利剑周平林强廖显波赵茂先秦艳
Owner 成都伊诺达博医药科技有限公司
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