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Preparation methods and purposes of Proellex(R)-V and intermediate of Proellex(R)-V

The technology of a diketone and steroid compound is applied in the field of preparation and use of trapristone acetate and its intermediates, which can solve problems such as being unfavorable to industrialized production, and achieve the advantages of being beneficial to industrialized production, easy to obtain raw materials and reagents, and simple raw materials and reagents. Effect

Active Publication Date: 2014-05-07
CHINA RESOURCES ZIZHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the product of the first step reaction of this route needs to be purified by column chromatography; the second step reaction requires a low temperature reaction of -78°C, which is not conducive to the expansion of industrial production

Method used

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  • Preparation methods and purposes of Proellex(R)-V and intermediate of Proellex(R)-V
  • Preparation methods and purposes of Proellex(R)-V and intermediate of Proellex(R)-V
  • Preparation methods and purposes of Proellex(R)-V and intermediate of Proellex(R)-V

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: 17α-Hydroxy-21-bromo-19-norpregna-5(10),9(11)-diene-3,20-dione

[0035] In a dry reaction flask, add 20g of compound 17α-hydroxy-20-methoxy-19-norpregna-5(10), 9(11), 20-triene-3-one, and then add 200mL Dichloromethane and 5mL triethylamine were stirred to dissolve, and the temperature was lowered to about 0°C. An appropriate amount of about 10% bromodichloromethane solution was added dropwise into the reaction flask, and the reaction was kept warm, and the reaction of the raw materials was monitored by TLC until complete. Slowly pour the reaction system into 100 mL of cooled 1 mol / L hydrochloric acid solution, let stand, separate the two phases, extract the aqueous phase with an appropriate amount of dichloromethane, combine the organic phases, and wash once with saturated brine. Dry over anhydrous magnesium sulfate, filter, and rinse the filter cake with an appropriate amount of dichloromethane. The combined filtrates were concentrated under reduced press...

Embodiment 2

[0036] Example 2: 3,3-Dimethoxy-17α-hydroxy-21-bromo-19-norpregna-5(10),9(11)-dien-20-one

[0037] In a dry reaction flask, add 20 g of compound 3,3-dimethoxy-17α-hydroxy-20-methoxy-19-norpregna-5(10), 9(11), 20-triene , and then add 200mL of dichloromethane and 50mL of triethylamine in sequence, stir to dissolve, and cool down to about 0°C. An appropriate amount of about 10% bromodichloromethane solution was added dropwise into the reaction flask, and the reaction was kept warm, and the reaction of the raw materials was monitored by TLC until complete. Slowly pour the reaction system into 100 mL of cooled saturated sodium chloride solution, let it stand, separate the two phases, extract the aqueous phase with an appropriate amount of dichloromethane, combine the organic phases, and wash once with saturated brine. Dry over anhydrous magnesium sulfate, filter, and rinse the filter cake with an appropriate amount of dichloromethane. The combined filtrates were concentrated und...

Embodiment 3

[0038] Example 3: 17α-Hydroxy-21-acetoxy-19-norpregna-5(10),9(11)-diene-3,20-dione

[0039] Add the compound 2 prepared in Example 1 into the dry reaction bottle, add 400 mL of acetone, protect it under nitrogen, stir at room temperature, then add 50 g of potassium acetate, 34 g of potassium iodide, and 1.2 mL of acetic acid in sequence. The temperature was raised to reflux, and the raw materials were monitored by TLC to complete the reaction. Cool down to room temperature, filter, rinse the filter cake once with a small amount of acetone, combine the filtrates, and concentrate to dryness under reduced pressure. Add dichloromethane to dissolve, then wash with saturated brine and water successively, dry over anhydrous magnesium sulfate, filter, rinse the filter cake once with a small amount of dichloromethane, combine the filtrates, and concentrate to dryness under reduced pressure to obtain about 19.2 g of the target product 17α-Hydroxy-21-acetoxy-19-norpregna-5(10),9(11)-die...

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Abstract

The invention relates to an intermediate of Proellex(R)-V and preparation method and purpose thereof. The invention provides a 4-step method for preparing 3,3,20,20-di(ethylenedioxy)-17alpha,21-dihydroxy-19-norpregna-5(10),9(11)-diene, which has the advantages of mild reaction condition, easily controlled operation process, easily available raw materials and reagents, low cost and high yield, and the method is suitable for industrial production, and the obtained 3,3,20,20-di(ethylenedioxy)-17alpha,21-dihydroxy-19-norpregna-5(10),9(11)-diene can be used for further preparing Proellex(R)-V.

Description

technical field [0001] The present invention relates to the preparation of the steroidal compound 3,3,20,20-bis(ethylenedioxy)-17α,21-bishydroxy-19-norpregna-5(10),9(11)-diene Preparation methods and intermediates thereof. Background technique [0002] Compound 3,3,20,20-bis(ethylenedioxy)-17α,21-dihydroxy-19-norpregna-5(10),9(11)-diene (compound 1) was prepared as Terapristone acetate (chemical name is 17α-acetoxy-11β[4-(N,N-dimethylamino)phenyl]-21-methoxy-19-norpregna-4,9( 10)-diene-3,20-dione, the key intermediate of TelapristoneAcetate in English; telapristone acetate, also known as CDB-4124, is a selective progesterone receptor modulator, which can be used to treat Uterine fibroids, endometriosis, breast cancer, dysmenorrhea, etc. [0003] WO9741145 discloses that 3,3-(ethylenedioxy)-17α-hydroxyl-17β-cyano-estro-5(10), 9(11)-diene is used as raw material to obtain the compound through 5 steps of reaction 1, further prepare to obtain telapristone acetate, its techno...

Claims

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Application Information

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IPC IPC(8): C07J21/00C07J5/00C07J7/00C07J41/00
Inventor 田卫学史学松王海杨柳
Owner CHINA RESOURCES ZIZHU PHARMA
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