Novel synthesis method of Abiraterone acetate

A technology of abiraterone acetate and a new method, applied in the direction of steroids, organic chemistry, etc., can solve the problems of inconvenient transportation, high market price, flammability and explosion, etc.

Inactive Publication Date: 2014-02-12
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

But diethyl-3-pyridyl borane market price is very expensive, and the necessary methyl diethyl borate flash point of synthesis diethyl-3-pyridyl borane (see following formula) is low, inflammable and explosive , the transportation is very inconvenient, which makes the source of diethyl-3-pyridylborane used in the synthesis of abiraterone acetate become a big problem, and this will definitely become a problem restricting the large-scale production of abiraterone acetate bottleneck

Method used

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  • Novel synthesis method of Abiraterone acetate
  • Novel synthesis method of Abiraterone acetate
  • Novel synthesis method of Abiraterone acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 17-(3-pyridyl)androst-5,16-dien-3beta-ol

[0032] 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 - boric acid, 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 at 50-55°C overnight to obtain 41.9 g of solid.

Embodiment 2

[0034] 17-(3-pyridyl)androst-5,16-dien-3beta-ol

[0035] Add 750ml of THF to a 3L three-necked flask, and add 44.1g of 17-bromo-androst-5,16-dien-3beta-ol, 264mg of bistriphenylphosphinepalladium chloride and 16.44g of pyridine-3 - boric acid, 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 39.4 g of solid.

Embodiment 3

[0037] 17-(3-pyridyl)androst-5,16-dien-3beta-ol

[0038] Add 750ml of THF to a 3L three-necked flask, and add 52.8 grams of 17-trifluoromethanesulfonate-androst-5,16-diene-3beta-ol and 264mg of bistriphenylphosphine palladium chloride successively under stirring And 16.44 grams of pyridine-3-boronic acid, finally add 345ml 2mol / L Na2CO3 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 at 50-55°C overnight to obtain 43.5 g of solid.

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Abstract

The invention discloses a novel synthesis method of Abiraterone acetate. The synthesis method replaces expensive pyridine-3-diethylborane with pyridine-3-bronic acid, which is available in the market and can be easily synthesized, to carry out the Suzuki coupling reaction so as to synthesize Abiraterone ester in a high yield. The novel synthesis method of Abiraterone has the advantages of lower raw material cost, simple technology, controllable reaction conditions, and high reaction yield.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis technology, in particular to a synthesis method of Abiraterone acetate. 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 clinically fou...

Claims

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Application Information

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