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Method for synthesizing steroid progestogen

A progesterone and steroid technology, applied in the field of medicinal chemistry, can solve the problems of low yield and achieve high yield, low cost, and large-scale industrial production value

Inactive Publication Date: 2006-11-22
JIANGSU CHUANGUO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this process is that there are no ready-made raw materials. From the structural analysis, the preparation of raw materials also needs several steps of reaction, and the yield is low.

Method used

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  • Method for synthesizing steroid progestogen
  • Method for synthesizing steroid progestogen
  • Method for synthesizing steroid progestogen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1, 13-Ethyl-3-methoxy-estro-1,3,5(10),8(9)-tetraen-17β-alcohol

[0040] Dissolve 50 grams of 13-ethyl-3-methoxy-estro-1,3,5(10), 8(9)-tetraen-17β-alcohol-acetate in 500 ml of methanol, add 20 g Potassium hydroxide was heated, and potassium hydroxide was dissolved. After 2 hours of reaction, TLC detected that the reaction was complete. The solution was transferred to a single-necked flask, and part of the solvent was evaporated under reduced pressure. A solid appeared, which was analyzed with 3000 ml of water, filtered, and dried to obtain 40 grams of solids.

Embodiment 2

[0041] Example 2, 13-ethyl-3-methoxy-estro-1,3,5(10)-triene-9,11-epoxy-8α, 17β-diol

[0042] 40 grams of 13-ethyl-3-methoxy-estro-1,3,5(10),8(9)-tetraen-17β-alcohol was dissolved in 400 milliliters of benzene, 60 grams of peracid was added, 500 1 ml of diethyl ether, continue to react for 2 hours, TLC detects that the reaction is complete, add potassium carbonate solution to stop the reaction, separate the organic layer, extract the water layer with ethyl acetate, combine the organic layers, wash with water to medium size, wash with saturated saline, and anhydrous sulfuric acid The sodium was dried and distilled under reduced pressure to obtain a solid, which was filtered to obtain a white solid weighing 32 grams.

Embodiment 3

[0043] Example 3, 13-Ethyl-3-methoxy-estro-1,3,5(10),8(9)-tetraen-11-one 17β-alcohol

[0044] Dissolve 10 g of epoxide 13-ethyl-3-methoxy-estro-1,3,5(10)-triene-9,11-epoxy-8α,17β-diol in 50 mL of methanol , add dropwise 55 milliliters of 18% hydrochloric acid under stirring, stir for 1 hour after dripping, add 200 milliliters of water to make the product precipitate as much as possible, filter to obtain a white solid, wash with water until neutral, dry at room temperature, weighing: 9.25 grams.

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PUM

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Abstract

The invention discloses a synthetic method of steroidal gestagen and key medium I, II, III, IV in the drug chemical technological domain, which adopts 13 ethyl- 1,3,5(10),8(9)- estrange tetraenes-17-alcohol as raw material to synthesize deoxidation pregnancy and depending pregnancy.

Description

Technical field: [0001] The invention belongs to the technical field of medicinal chemistry. In particular it relates to methods for the synthesis of steroidal progestogens. Background technique: [0002] 13β-Ethyl-11-Methylene-18.19-Dianox-17α-Pregn-4-ene-20-Ethynyl-17β-Hydroxy is a steroidal progestin contraceptive that can inhibit ovulation and gonadotropin Secretion, the trade name is Marvelon. 13β-ethyl-11-methylene-18.19-bisanox-17α-pregnant-4-en-3-ketone-20-ethynyl-17β-hydroxyl is a derivative of desogestrel, and the Netherlands Organon company will It was developed into a single-root subcutaneous sustained-release long-acting contraceptive implant with the trade name Implanon. Its synthetic route has following several kinds: [0003] (1) Synthesis of 13β-ethyl-11-methylene-18.19-bisanth-17α-pregna-4-ene- from 11-hydroxyestr-5-ene-3,17-dione 20-ethynyl-17β-hydroxyl, see reaction formula 1: [0004] [0005] [0006] Reaction one ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00A61P15/18
Inventor 李金亮赵楠张薛鑫马玲
Owner JIANGSU CHUANGUO PHARMA CO LTD
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