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

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
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Example Embodiment

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

[0035] In a dry reaction flask, add 20g of compound 17α-hydroxy-20-methoxy-19-norgestrel-5(10), 9(11), 20-trien-3-one, and then add 200mL Dichloromethane and 5 mL of triethylamine are stirred to dissolve, and the temperature is lowered to about 0°C. Approximately 10% bromine dichloromethane solution was added dropwise to the reaction flask, the reaction was kept warm, and the TLC monitored the raw material reaction to completion. The reaction system was slowly poured into 100 mL of a cooled 1mol / L hydrochloric acid solution, left to stand, the two phases were separated, the aqueous phase was extracted with an appropriate amount of dichloromethane, the organic phases were combined, and washed once with saturated brine. Dry with anhydrous magnesium sulfate, filter, and rinse the filter cake with an appropriate amount of dichloromethane. The filtrates were combined and concentrated under reduced pr...

Example Embodiment

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

[0037] In the dry reaction flask, add 20g compound 3,3-dimethoxy-17α-hydroxy-20-methoxy-19-norgestrel-5(10),9(11),20-triene , Then add 200mL dichloromethane and 50mL triethylamine in sequence, stir to dissolve, and cool to about 0℃. Approximately 10% bromine dichloromethane solution was added dropwise to the reaction flask, the reaction was kept warm, and the TLC monitored the raw material reaction to completion. The reaction system was slowly poured into 100 mL of cooled saturated sodium chloride solution, left to stand, the two phases were separated, the aqueous phase was extracted with an appropriate amount of dichloromethane, the organic phases were combined, and washed once with saturated brine. Dry with anhydrous magnesium sulfate, filter, and rinse the filter cake with an appropriate amount of dichloromethane. The filtrates were combined and concentrated under reduced pressure t...

Example Embodiment

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

[0039] The compound 2 prepared in Example 1 was added to a dry reaction flask, 400 mL of acetone was added, protected by nitrogen, stirred at room temperature, and then 50 g of potassium acetate, 34 g of potassium iodide, and 1.2 mL of acetic acid were added in sequence. The temperature was raised to reflux, and TLC monitored the raw material reaction to completion. Cool to room temperature, filter, rinse the filter cake once with a small amount of acetone, combine the filtrate, and concentrate to dryness under reduced pressure. Add dichloromethane to dissolve, then wash with saturated brine and water in turn, dry with anhydrous magnesium sulfate, filter, rinse the filter cake once with a small amount of dichloromethane, combine the filtrates, concentrate under reduced pressure to dryness, obtain about 19.2g of the target product 17α-hydroxy-21-acetoxy-19-norgestrel-5(10),9(11)-diene-3,20-dione...

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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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