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A method for reducing residual palladium in abiraterone acetate

A technology for abiraterone acetate and palladium residues, applied in the directions of steroids, organic chemistry, etc., can solve problems such as high toxicity, and achieve the effects of low cost, high removal capacity, and reduction of palladium residues

Active Publication Date: 2021-11-30
山东安弘制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example: Chinese patent document CN107840866A provides a kind of preparation method of abiraterone acetate, this method uses the compound of formula II to process abiraterone acetate, but this method still uses organophosphorus reagent to remove palladium catalyst, there is bigger toxicity

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  • A method for reducing residual palladium in abiraterone acetate
  • A method for reducing residual palladium in abiraterone acetate
  • A method for reducing residual palladium in abiraterone acetate

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Embodiment 1

[0051] A method for reducing residual palladium in abiraterone acetate, comprising steps as follows:

[0052] (1) Preparation of Abiraterone Acetate Intermediate Reaction Solution

[0053] Mix 20g of 17-iodo-androst-5,16-dien-3β-ol with 10g of methyl(3-pyridyl)borane, 0.2g of bistriphenylphosphinepalladium dichloride, 40g of sodium carbonate, 200mL of Methyl sulfoxide was added into the reaction flask, the temperature was raised to 85° C. and the temperature was maintained for 3 hours, and the obtained reaction solution was directly filtered while hot to obtain the abiraterone acetate intermediate reaction solution.

[0054] (2) Adding 15 mL of a mass concentration of 30% sodium bisulfite solution to the abiraterone acetate intermediate reaction solution obtained in 200 mL of step (1), stirred at 85° C. for 2 h; then added 3 g of activated carbon for adsorption for 30 minutes, and then Filtrate directly while it is hot, cool the filtrate to 7°C for crystallization for 2 h, filt...

Embodiment 2

[0059] A method for reducing residual palladium in abiraterone acetate, comprising steps as follows:

[0060] (1) Preparation of Abiraterone Acetate Intermediate Reaction Solution

[0061] As described in embodiment 1 step (1).

[0062] (2) Adding 10mL of mass concentration to 200mL of the abiraterone acetate intermediate reaction solution obtained in step (1) is a 30% sodium bisulfite solution, stirred at 83°C for 2h; then added 3g of activated carbon for adsorption for 30 minutes, and then Filtrate directly while it is hot, cool the filtrate to 6°C for crystallization for 2 hours, filter, wash the filtered precipitate with purified water twice, and dry at 75°C for 12 hours to obtain 12.23 g of abiraterone acetate intermediate, with a molar yield of 69.7% .

[0063] (3) Preparation of Abiraterone Acetate

[0064] As described in embodiment 1 step (3).

[0065] Use inductively coupled plasma mass spectrometry (ICP-MS) to detect that the palladium content in the prepared ab...

Embodiment 3

[0067] A method for reducing residual palladium in abiraterone acetate, comprising steps as follows:

[0068] (1) Preparation of Abiraterone Acetate Intermediate Reaction Solution

[0069] As described in embodiment 1 step (1).

[0070] (2) Adding 15mL of mass concentration to 200mL of the abiraterone acetate intermediate reaction liquid obtained in step (1) is a 30% sodium bisulfite solution, stirred at 83°C for 2h; then added 2g of activated carbon for adsorption for 30 minutes, and then Filtrate directly while it is hot, cool the filtrate to 6°C to crystallize for 2 hours, filter, wash the filtered precipitate with purified water twice, and dry at 75°C for 12 hours to obtain 12.42 g of abiraterone acetate intermediate, with a molar yield of 70.8% .

[0071] (3) Preparation of Abiraterone Acetate

[0072] As described in embodiment 1 step (3).

[0073] Use inductively coupled plasma mass spectrometry (ICP-MS) to detect that the palladium content in the prepared abiratero...

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Abstract

The invention provides a method for reducing palladium residues in abiraterone acetate, comprising the steps of: 17-iodine-androst-5,16-diene-3β-alcohol and alkyl (3-pyridyl) borane Reaction under the action of a palladium catalyst to obtain the abiraterone acetate intermediate reaction solution; add sodium bisulfite solution to the obtained abiraterone acetate intermediate reaction solution, and stir at high temperature; add activated carbon to absorb, filter, and cool the filtrate to crystallize. filtering, washing, and drying to obtain the abiraterone acetate intermediate; acylation reaction between the abiraterone acetate intermediate and acetic anhydride to obtain the abiraterone acetate. The method of the invention has simple process, high ability to remove free palladium ions, and can effectively reduce the palladium content in abiraterone acetate.

Description

technical field [0001] The invention relates to a method for reducing residual palladium in abiraterone acetate, belonging to the technical field of medicinal chemistry. Background technique [0002] Abiraterone acetate, a prodrug of abiraterone, is rapidly converted in vivo to abiraterone, a selective, irreversible steroid of CYP17 (17α-hydroxylase and C17,20-lyase) Body inhibitors, which prevent testosterone synthesis in testes, adrenal glands, and tumors by inhibiting enzyme activity, used in combination with prednisone or prednisolone to treat castration in patients who have failed androgen castration therapy and docetaxel chemotherapy Treatment of resistant metastatic prostate cancer (mCRPC). The chemical name of abiraterone acetate is (3β)-17-(3-pyridyl)-androst-5,16-diene-3-acetate, and its structural formula is as shown in formula I below: [0003] [0004] Regarding the synthesis of abiraterone acetate, there are a series of patent documents CN111349138A, US560...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J43/00
CPCC07J43/003
Inventor 徐宝旺申新德孔改兰李同强
Owner 山东安弘制药有限公司