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Preparation method of abiraterone acetate

A technology of abiraterone acetate and abiraterone, which is applied in the field of medicine to achieve the effect of shortening the reaction steps and improving the yield

Inactive Publication Date: 2012-12-26
北京万全阳光医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

lead to high end product cost

Method used

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  • Preparation method of abiraterone acetate
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  • Preparation method of abiraterone acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 : Preparation of (3β)-17-iodo-androst-5,16-dien-3-ol acetate (compound II).

[0025]

[0026] I II

[0027] In a 250ml three-necked flask, add 39.8 g (0.1 mmol) of compound I, 300 ml of acetonitrile, and 20 g of triethylamine, and add 9.4 g (0.12 mmol) of acetyl chloride dropwise into the reaction system at room temperature. After dropping, heat up to 70°C and react for 4 hours. TLC spotting test shows that the reaction is complete. Cool to room temperature, distill and remove the solvent to obtain a residue. Add 50ml of water, extract with ethyl acetate (20ml×3), anhydrous sodium sulfate After drying, the desiccant was filtered off, and the filtrate was distilled under reduced pressure to obtain 38.7 g of white solid, yield: 97.9%.

[0028] MS(+1):441.

[0029] 1 HNMR: δ (ppm, CDCl 3 ), 6.41-6.42 (t, 1H), 5.37-5.39 (t, H), 3.41-3.43 (q, 2H), 2.87-2.89 (m, 1H), 2.21-2.23 (d, 1H), 2.124-2.13 (d, 1H), 2.01 (s, 3H), 1.96-1.97 (d...

Embodiment 2

[0031] Example 2 : Preparation of Abiraterone Acetate (Compound TM)

[0032]

[0033] In a 250ml three-necked flask with reflux condensation, add 22.0 grams of (3β)-17-iodo-androst-5,16-dien-3-ol acetate (compound II, 0.05mol), 15.3g 3- Iodopyridine (compound III, 0.075 mol). Stir, add copper powder 15.8g (0.25mol), quickly heat up to 210°C, react for 4 hours, TLC detects that the reaction is complete, cool, add ethyl acetate, 100 ml each time, elute 3 times, combine the organic phase, 50mL saturated salt Wash once with water, separate the organic phase, dry over anhydrous sodium sulfate for 3 h, filter off the desiccant, and concentrate the organic phase to obtain an off-white solid. The obtained off-white solid was recrystallized once from ethyl acetate-petroleum ether (2:1, 300 mL), and the white solid was dried in vacuum to obtain 11.7 g. The obtained 11.7 g white solid was recrystallized from ethanol (120 mL), and the obtained white solid was vacuum-dried to obtain...

Embodiment 3

[0037] Example 3 : (Preparation of (3β)-17-iodo-androst-5,16-dien-3-ol acetate (compound II).

[0038]

[0039] I II

[0040] In a 250ml three-neck flask, add 39.8 g (0.1 mmol) of compound I, 300 ml of dichloromethane, and 18 g of sodium bicarbonate, and add 9.4 g (0.12 mmol) of acetyl chloride dropwise to the reaction system at room temperature. After dropping, heat up to 75°C to react for 4 hours, TLC spotting test shows that the reaction is complete, cool to room temperature, filter off the inorganic salt, distill the organic solvent, remove the solvent, and obtain a residue, add 50ml of water, extract with ethyl acetate (20ml× 3), dried over anhydrous sodium sulfate, filtered off the desiccant, and distilled the filtrate under reduced pressure to obtain 39.2 g of white solid, yield: 88.9%.

[0041] NMR data are the same as Example 1.

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Abstract

The invention belongs to the filed of medical technology, and particularly discloses a preparation method of abiraterone acetate, which comprises the following steps that compound I is acetylated to obtain compound II in an organic solvent, and compound II is coupled with halogenated pyridine to obtain the target product. The invention provides a preparation method of abiraterone acetate which can reduce the cost.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method of abiraterone acetate. Background technique [0002] Abiraterone acetate, chemical name (3β)-17-(3-pyridinyl)-Androsta-5,16–dien-3-ol acetate (ester), combined with prednisone (steroid) for advanced (Metastatic) Castration-refractory prostate cancer who have been treated with docetaxel. [0003] In prostate cancer patients, the male hormone testosterone stimulates the growth of prostate tumors. Drugs or surgery can reduce testosterone production or block the effects of testosterone. However, in some cases prostate cancer can continue to develop even when testosterone levels are low. This is called castration-resistant prostate cancer. Abiraterone acetate targets a protein called cytochrome P450 17A1 (CYP17A1), which is important for testosterone production. Abiraterone acetate decreases testosterone production which prevents cancer cells fro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00
Inventor 翟富民王传申卞松陈拥军
Owner 北京万全阳光医药科技有限公司
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