Polymorphs of abiraterone acetate and preparation method thereof

A technology of abiraterone acetate and abiraterone acetate, which is applied to the polymorphic form of abiraterone acetate and its preparation field, can solve the problem of different binding force of crystal particles, influence on drug dissolution rate, influence on drug fluidity and pressure. Issues such as tablet hardness, tablet weight variation, content uniformity, and physical stability

Inactive Publication Date: 2010-07-07
深圳万乐药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The marketed abiraterone acetate is a tablet, as a solid preparation, because different crystal forms affect the dissolution rate of the drug, and the difference in surface free energy of different crystal forms causes different binding forces between the crystal particles, which affects the flow of the drug properties and tablet hardness, difference in tablet weight, content uniformity and physical stability, so it is necessary to study its crystal form

Method used

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  • Polymorphs of abiraterone acetate and preparation method thereof
  • Polymorphs of abiraterone acetate and preparation method thereof
  • Polymorphs of abiraterone acetate and preparation method thereof

Examples

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Comparison scheme
Effect test

Embodiment 1

[0041] The preparation of embodiment 1 abiraterone acetate polymorph A

[0042] Add 30g of pure abiraterone acetate obtained through column purification into 140ml of ethyl acetate, stir and dissolve at room temperature, slowly add 700ml of petroleum ether after dissolution, concentrate the whole to 280ml, place at room temperature for crystallization, filter, and oven at 50°C After drying for 4 hours, 15.2 g of white crystals were obtained, yield: 76%.

[0043] HPLC test purity 99.9239%, the largest single impurity 0.0761%,

[0044] Moisture 0.00%

[0045] DSC melting point: 144.7-145.7°C

[0046] Specific rotation: -38.0 (C=1.0g / 100ml, ethanol)

Embodiment 2

[0047] Embodiment 2 Preparation of Abiraterone Acetate Polymorph A

[0048] Add 30 g of pure abiraterone acetate obtained through column purification into 180 mL of ethanol / n-hexane with a volume ratio of 1:9, heat and stir to dissolve, filter while hot after complete dissolution, place at room temperature for crystallization, filter, 50°C Oven-dried for 4 hours to obtain 12.5 g of white crystals, yield: 62.5%.

[0049] HPLC test purity 99.9812%, the largest single impurity 0.0155%,

[0050] Moisture 0.00%

[0051] DSC melting point: 144.9-146.0°C

[0052] Specific rotation: -39.98 (C=1.0g / 100ml, ethanol)

Embodiment 3

[0053] Embodiment 3 Preparation of Abiraterone Acetate Polymorph A

[0054] Add 30 g of pure abiraterone acetate obtained through column purification into 140 mL of ethanol / water with a volume ratio of 1:9, heat and stir to dissolve, filter while hot after complete dissolution, place crystallization at room temperature, filter, and dry in an oven at 70°C After drying for 2 hours, 16.5 g of white crystals were obtained, yield: 62.5%.

[0055] HPLC test purity 99.7903%, the largest single impurity 0.1065%,

[0056] Moisture: 0.00%

[0057] DSC melting point: 144.5-145.1°C

[0058] Specific rotation: -38.91 (C=1.0g / 100ml, ethanol)

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Abstract

The invention discloses polymorphs A, B, C and D of abiraterone acetate. A preparation method of the polymorphs comprises the step of re-crystallizing the abiraterone acetate subjected to the separation and the purification of a chromatographic column in different solvents. Through stable investigation, four polymorphs have favorable stability and flowability, can be used as raw materials for storage and transportation and are suitably applied to antitumor medicinal preparations.

Description

technical field [0001] The invention relates to polymorphic forms of pharmaceutical compounds, in particular to polymorphic forms of abiraterone acetate and a preparation method thereof. Background technique [0002] Abiraterone is an oral inhibitor of cytochrome oxidase P450 (CYP450) c17, which reduces androgen levels by inhibiting the key enzyme in androgen synthesis - CYP450c17, and has effects on androgen in the testis and other parts of the body Inhibition, for the treatment of advanced prostate cancer. Abiraterone acetate is the prodrug of Abiraterone, also known as Abiraterone-3-acetate, its structural formula is: [0003] [0004] The synthesis method of the compound is disclosed in WO-A-95 / 09178, but the crystal form of the compound is not involved, and there is no other document reporting the crystal form of abiraterone. It is known that the polymorphic form of a drug is of great significance to the physical and chemical properties of the drug, bioavailability...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00A61K31/58A61P35/00
Inventor 钱建彬刘飞键陈轶之张广明王庆秋郭才旺
Owner 深圳万乐药业有限公司
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