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Steroid compound, preparation method therefor and use of steroid compound

A steroid compound and compound technology, applied in the field of steroid compound and its preparation and use, can solve the problems affecting the quality of the final product, the single starting material, and the high cost, achieve the simple and easy availability of raw materials and reagents, reduce the overall cost, Fast response time

Active Publication Date: 2016-10-26
CHINA RESOURCES ZIZHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the starting material is single, the cost is high, and the impurities produced in the fourth and fifth steps are more, which affects the quality of the final product

Method used

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  • Steroid compound, preparation method therefor and use of steroid compound
  • Steroid compound, preparation method therefor and use of steroid compound
  • Steroid compound, preparation method therefor and use of steroid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1: 3,3-Dimethoxy-17α-ethynyl-17β-hydroxy-estro-5(10),9(11)-diene

[0059]Under the protection of nitrogen, add 1.2 L of tetrahydrofuran and 400 g of potassium hydroxide into the dry reaction flask, then lower the temperature to below 5° C., and pass through acetylene gas. Add 1L of acetone, raise the temperature to 35°C-40°C, keep flowing acetylene gas, and stir for 2 hours. Dissolve 100g of 3,3-dimethoxy-estro-5(10), 9(11)-dien-17-one in 1L of tetrahydrofuran, and add it dropwise to the reaction solution. After the dropwise addition, control the temperature at 35 ℃~40℃ for 1 hour. After the reaction was completed, 750 mL of saturated ammonium chloride solution was added and the reaction mixture was stirred for 10 min. The organic layer was separated, and the aqueous layer was extracted with 300 mL of tetrahydrofuran. The combined organic layers were washed with 750 mL of saturated ammonium chloride, concentrated under reduced pressure to 600 mL, poured into ...

Embodiment 2

[0061] Example 2: 3,3-Dimethoxy-21-(phenyl-sulfinyl)-19-norpregna-5(10), 9(11), 17(20), 20-tetraene

[0062] Add 105g 3,3-dimethoxy-17α-ethynyl-17β-hydroxy-estro-5(10), 9(11)-diene, 1400mL dichloromethane, 130mL triethyl Amine and 25mL glacial acetic acid, lower the temperature to 0~-10°C, add dropwise 120mL of methylene chloride solution containing 63g of phenylsulfinyl chloride, keep the dropwise addition temperature not exceeding 0°C, after the dropwise addition, add 210mL of water and 105mL of methanol , and stirred for 30 minutes. The organic layer was separated, washed with 1N hydrochloric acid and saturated sodium carbonate solution, and finally washed with water until neutral. The organic layer was dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. Add isopropyl ether to the residue, cool to 0°C and stir for 30 minutes, and filter to obtain 120 g of 3,3-dimethoxy-21-(phenyl-sulfinyl)-19-norpregna-5(10),9 (11), 17(20), 20-tetraen...

Embodiment 3

[0064] Example 3: 3,3-Dimethoxy-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene

[0065] Add 120g of 3,3-dimethoxy-21-(phenyl-sulfinyl)-19-norpregna-5(10), 9(11), 17(20), 20 -tetraene, 7.2g of sodium methoxide and 3600mL of anhydrous methanol, the temperature was raised to 60°C-65°C and stirred for 3h, then 36mL of trimethyl phosphite was added, and the reaction was continued for 1h with heat preservation and stirring. After the reaction was completed, the reaction solution was poured into 8 L of water, and a pale yellow solid was precipitated. After stirring for 30 minutes, filter to obtain 82g 3,3-dimethoxy-17α-hydroxyl-20-methoxy-19-norpregna-5(10), 9(11), 20-triene .

[0066] MS(m / z): 374[M] + ; 1 H-NMR (CDCl 3 ): δ0.81 (3H, 18-CH 3 ), δ3.11-3.13 (6H, -O-CH 3 and -O-CH 3 ), δ5.05-5.02 (2H, 20-=CH 2 ), δ3.43 (3H, -O-CH 3 ), δ5.30(1H, 11-H); 13 C-NMR: 211.64(19-C), 136.02(C-5), 130.06(C-9), 126.06(C-10), 117.68(C-11), 98.79(C-3), 89.76(C- 17), 48.28 (-O...

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Abstract

The invention relates to a steroid compound, a preparation method therefor and use of the steroid compound. The existing methods for preparing 3,3,20,20-bis(ethylenedioxy)-17alpha-hydroxyl-19-norpregna-5(10),9(11)-diene have the problems that starting materials are single, the cost is relatively high, the product quality is poor, the methods are not suitable for industrial production, and the like. The novel steroid compound, the preparation method therefor and the use of the compound, provided by the invention, have the advantages that the steroid compound can be used for preparing 3,3,20,20-bis(ethylenedioxy)-17alpha-hydroxyl-19-norpregna-5(10), 9(11)-diene; and the preparation method is high in yield and product quality, mild in reaction conditions, rich and readily available in raw material and relatively low in cost, thereby facilitating industrial production.

Description

technical field [0001] The present invention relates to the preparation method of steroidal compound 3,3,20,20-bis(ethylenedioxy)-17α-hydroxyl-19-norpregna-5(10),9(11)-diene and use. Background technique [0002] Compound 3,3,20,20-bis(ethylenedioxy)-17α-hydroxy-19-norpregna-5(10),9(11)-diene is the key to the preparation of ulipristal acetate intermediate. Ulipristal acetate is a steroid with antiprogestogenic and anticorticoid activity, used in the treatment of gynecological diseases, contraception, treatment of Cushing's syndrome and glaucoma, etc. And the preparation method of 3,3,20,20-bis(ethylenedioxy)-17α-hydroxyl-19-norpregna-5(10),20-bis(ethylenedioxy)-diene disclosed in literature has: [0003] U.S. Patent No. 5,929,262, with 3,3-(ethylenedioxy)-17α-hydroxyl-17β-cyano-estradiol-5(10), 9(11)-diene as raw material through 3-step reaction to obtain 3 , 3,20,20-bis(ethylenedioxy)-17α-hydroxy-19-norpregna-5(10),9(11)-diene, the total yield was 55%. The process rou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J21/00C07J31/00
CPCC07J21/006C07J31/006
Inventor 王海史学松田卫学
Owner CHINA RESOURCES ZIZHU PHARMA