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Preparation method of abiraterone acetate

A technology of abiraterone acetate and alcohol acetate, which is applied in the field of preparation of abiraterone acetate, can solve problems such as yield reduction, influence industrialization effect, and be difficult to purify, achieve reliable quality, promote economic and technological development, and improve raw materials. easy-to-get effect

Active Publication Date: 2013-12-18
南京广祺医药科技有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Chinese patent No. CN101044155 research points out, because basic catalyst 2,6-di-tert-butyl-4-methylpyridine (DTBMP) is used in the preparation process of triflate, the elimination reaction of acetyl group easily occurs, making The yield is reduced and it is difficult to purify, which affects the industrialization effect of the process
[0016] In summary, although the synthetic route of abiraterone acetate involved in the current published literature reports has been optimized and improved in the reaction sequence, coupling mode, hydroxyl protection and deprotection, its preparation cost, yield There are still many deficiencies in aspects such as waste discharge and three wastes, especially how to reduce reaction steps, improve chemical selectivity and reduce side reactions, which have important practical significance for the economic and technological development of abiraterone acetate raw materials

Method used

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

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Embodiment 1

[0032] Under nitrogen atmosphere, 3-bromopyridine (1.88 g, 12 mmol) and 15 mL of anhydrous ether were added to a dry reaction flask, the temperature was lowered to -78 °C, n-butyllithium n-hexane solution (2.5 M, 5 mL) was added dropwise, and the mixture was stirred. The reaction was carried out for 45 minutes. Keeping at -78°C, 25 mL of tetrahydrofuran solution of dehydroepiandrosterone acetate (3.3 g, 10 mmol) was added dropwise to the system. It was naturally warmed to room temperature and the reaction was stirred for 24 hours. At 0°C, the reaction was quenched with saturated ammonium chloride solution, and after stirring, extracted with dichloromethane three times, the organic phases were combined, washed with water and saturated brine successively, and dried over anhydrous magnesium sulfate. The dichloromethane was recovered under reduced pressure, and the residue was recrystallized from ethyl acetate / n-hexane to obtain 1.74 g of 17-(3-pyridine)-17-hydroxy-androst-5-ene-...

Embodiment 2

[0034] Under nitrogen atmosphere, 17-(3-pyridine)-17-hydroxy-androst-5-en-3β-ol acetate (II) (2.05 g, 5 mmol) and 25 mL of toluene were added to a dry reaction flask, and stirred. Methyl N-(triethylammoniumsulfonyl)carbamate (Burgess reagent) (1.28 g, 5 mmol) was added, the reaction was carried out at room temperature for 1 hour, the temperature was raised to 85°C, and the reaction was continued for 1 hour. Additional Burgess reagent (1.28 g, 5 mmol) was added, and the reaction was carried out at room temperature for 1 hour. The temperature was raised to 85° C. and the reaction was continued for 1 hour. TLC detection reaction was completed. After cooling, the reaction was quenched with ice water. The organic phase was separated and the aqueous phase was extracted twice with toluene. The organic phases were combined, washed successively with water and brine, and dried over anhydrous sodium sulfate. Toluene was recovered under reduced pressure, and the residue was recrystalli...

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Abstract

The invention discloses a preparation method of abiraterone acetate (I). The preparation method comprises the following steps of: based on dehydroepiandrosterone acetate as a raw material, performing addition reaction with 3-pyridyllithium to generate 17-(3-pyridyl)-17-hydroxy-androst-5-ene-3 beta-ol acetate (II); performing elimination reaction on the intermediate (II) under the action of a Burgess reagent to get abiraterone acetate (I). The preparation method has the advantages of simple process, easiness in obtainment of raw materials and controllable quality, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis method design and preparation of bulk drugs and intermediates, in particular to a preparation method of abiraterone acetate. Background technique [0002] Abiraterone acetate (the chemical name is 17-(3-pyridyl)-androsta-5,16-dien-3β-ol acetate, I) is an orally effective drug developed by Centocor Oftho in the United States. The androgen biosynthesis inhibitor; approved by the US Food and Drug Administration (FDA) and the European Medicines Evaluation Agency (EMEA) in 2011, the trade name is Zytiga. The drug is clinically used in combination with prednisone to treat metastatic advanced prostate cancer that is resistant to traditional hormone therapy. It can not only reduce the level of prostate specific antigen, but also help shrink the tumor and prolong the period of advanced prostate cancer. patient's life. Recently, the US Food and Drug Administration and the European Agency for the...

Claims

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Application Information

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IPC IPC(8): C07J43/00
Inventor 许学农
Owner 南京广祺医药科技有限公司
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