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Method for preparing abiraterone acetate

A technology of abiraterone acetate and pyridine boric acid, applied in the directions of steroids, organic chemistry, etc., can solve the problems of increasing operation time and difficulty, unfavorable scale-up production, easy residual impurities, etc., achieves strong practical value, reduces raw material costs, The effect of easy purification

Inactive Publication Date: 2014-03-26
重庆瑞泊莱医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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, and the filter cake obtained by filtration is viscous and easily retains impurities. Abiraterone acetate 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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  • Method for preparing abiraterone acetate
  • Method for preparing abiraterone acetate
  • Method for preparing abiraterone acetate

Examples

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Embodiment 1

[0031]

[0032] Get 15g formula I compound, after dissolving with 100mL dioxane, transfer to a 250mL there-necked flask equipped with thermometer, reflux condenser and argon conduit; Under argon protection, add 3-pyridineboronic acid ( 4.8g), potassium carbonate aqueous solution (50mL) with a molar concentration of 2mol / L, and bis(triphenylphosphine)palladium dichloride (35mg); heated to reflux under stirring, and the reaction was completed (about 8 hours of reflux reaction), Add 50mL ethyl acetate and 50mL water to the reaction system, separate the liquid, extract the water phase with 3×50mL ethyl acetate; collect the organic phase, wash with 2×50mL water first, then wash with 2×50mL saturated brine; Dry over sodium sulfate, filter, and concentrate the organic solvent in the dry filtrate to obtain 15 g of brown oil; add ethyl acetate-n-hexane mixed solvent with a volume ratio of 1:4 to this oil, and stir at room temperature for 3 hours to make After full analysis and cryst...

Embodiment 2

[0034] Get 15g formula I compound, after dissolving with 50mL toluene, transfer to a 250mL there-necked flask equipped with thermometer, reflux condenser and argon conduit; ), a potassium carbonate aqueous solution (50mL) with a molar concentration of 2mol / L and bis(triphenylphosphine)palladium dichloride (35mg); heated to reflux under stirring, and the reaction was completed (about 8 hours of reflux reaction), to the reaction Add 50mL ethyl acetate and 50mL water to the system, separate the liquids, and extract the aqueous phase with 3×50mL ethyl acetate; collect the organic phase, wash it with 2×50mL water first, and then wash it with 2×50mL saturated brine; anhydrous sulfuric acid Dry over sodium, filter, and concentrate the organic solvent in the dry filtrate to obtain 14 g of brown oil; add ethyl acetate-n-hexane mixed solvent with a volume ratio of 1:4 to this oil, stir at room temperature for 3 hours to fully analyze Crystallization, to obtain 7.5g of dark gray solid, m...

Embodiment 3

[0036]Take 15g of the compound of formula I, dissolve it with 90mL of tetrahydrofuran, and transfer it to a 250mL three-neck flask equipped with a thermometer, reflux condenser and argon gas conduit; under the protection of argon, add 3-pyridineboronic acid pinacol ester to the system (8.2g), dipotassium hydrogen phosphate aqueous solution (50mL) with a molar concentration of 2mol / L, and tetrakis(triphenylphosphine)palladium (30mg); heated to reflux under stirring, and the reaction was completed (about 8 hours of reflux reaction), Add 50mL ethyl acetate and 50mL water to the reaction system, separate the liquid, extract the water phase with 3×50mL ethyl acetate; collect the organic phase, wash with 2×50mL water first, then wash with 2×50mL saturated brine; Dry over sodium sulfate, filter, and concentrate the organic solvent in the dry filtrate to obtain 14.5 g of brown oil; add ethyl acetate-n-hexane mixed solvent with a volume ratio of 1:4 to this oil, and stir at room tempera...

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Abstract

The invention discloses a method for preparing abiraterone acetate. The method comprises the following steps of: (A) carrying out Suzuki coupling reaction on a formula I compound and 3-pyridineboric acid or a 3-pyridineboric acid derivative in a mixed solvent formed by an organic aprotic solvent and water under the action of a metal palladium catalyst and alkali; (B) after the reaction is finished, adding ethyl acetate and the water to a reaction system for liquid separation; collecting organic phases, sequentially washing by using the water and a saturated salt solution, drying and concentrating to obtain an oily crude product; (3) adding a crystallizing solvent to the oily crude product, and stirring for crystallization; (D) collecting solids for recrystallization. The method disclosed by the invention has the advantages of simple process, low cost and easiness for obtaining of raw materials, easiness for purifying treatment, high yield, low cost, high finished product purity, and the like, completely meets the requirement for industrialized batch production and has very high practical value.

Description

technical field [0001] The invention relates to a method for preparing abiraterone acetate, belonging to the technical field of organic synthesis. Background technique [0002] Abiraterone acetate, also known as abiraterone-3-acetate, is a prodrug of abiraterone, and its chemical structure is: [0003] [0004] Abiraterone acetate is an oral cytochrome oxidase CYP450c17 inhibitor, which reduces androgen levels by inhibiting the key enzyme CYP450c17 in androgen synthesis, and has inhibitory effects on androgen in the testis and other parts of the body. It is used for Treatment of prostate cancer. [0005] The compound and its synthesis method were first disclosed in WO9320097A. The synthesis route is to use dehydroepiandrosterone acetate as raw material to prepare its trifluoromethanesulfonyl derivative (formula I), and then combine it with diethyl (3-pyridyl) Abiraterone acetate (formula II) is obtained by borane condensation in two steps, and the synthetic route is as ...

Claims

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Application Information

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IPC IPC(8): C07J43/00
Inventor 高河勇陈琳舒芬彭焕庆杨理君
Owner 重庆瑞泊莱医药科技有限公司
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