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Method for synthesizing 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone

A technology for norpregnantine and methylpregnantine, which is applied in the directions of steroids, organic chemistry and the like, can solve the problems of high cost and low yield, and achieve the effects of low cost and short synthesis process.

Active Publication Date: 2017-06-13
丽江映华生物药业有限公司 +1
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  • Claims
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Problems solved by technology

This process route mainly obtains 17α-hydroxyprogesterone through the oxidation of 17(20) double bond, and the yield is low and the cost is high

Method used

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  • Method for synthesizing 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone
  • Method for synthesizing 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone

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Embodiment Construction

[0016] The present invention will be further described below in conjunction with the examples.

[0017] The present invention uses 17α-hydroxy-19-norpregna-4-ene-3,20-dione as raw material, and synthesizes 6-methylene-17α-hydroxy-19-norpregne 4-ene-3,20-dione, the specific route is as follows.

[0018]

[0019] 1. Preparation of 3-ethoxy-17α-hydroxy-19-desmethylpregna-4-en-20-one

[0020] 17α-Hydroxy-19-norpregna-4-ene-3,20-dione (3 g, 9.5 mmol) was dissolved in absolute ethanol (15 mL), p-toluenesulfonic acid monohydrate (0.07 g) was added, and then Triethyl orthoformate (2.82g, 19mmol) was added, the reaction solution was stirred at 20°C for 30min, heated to 80°C and continued to stir and react for 30min, most of the solvent was concentrated under reduced pressure, a small amount of ethyl acetate was added to help dissolve, and an excess of petroleum oil was added. The ether was nearly turbid, placed in a -7°C refrigerator overnight, the precipitated crystals were filte...

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Abstract

The invention provides a method for synthesizing 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone. The method comprises the steps of (1) using 17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone for preparing 3-ethyoxyl-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-20-ketone; (2) using the product in the step (1) for preparing 3-ethyoxyl-6-(N-methyl-N-phenyl) aminomethyl-17 alpha-hydroxy-19-desmethyl pregnene-4,6-diene-20-ketone; (3) using the product in the step (2) for preparing the 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone. According to the method provided by the invention, the 6-methylene-17 alpha-hydroxy-19-desmethyl pregnene-4-alkene-3,20-diketone is synthesized through three-step reaction, a synthetic process is simple and short, and low in cost, and the yield achieves 55 percent or above.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing 6-methylene-17α-hydroxy-19-norpregna-4-ene-3,20-dione. Background technique [0002] 6-methylene-17α-hydroxy-19-norpregn-4-ene-3,20-dione is an important intermediate in the synthesis of nomegestrol, the compound is represented by structural formula 1, it and acetic anhydride The fourth-generation progestogen nomegestrol is obtained through esterification reaction and double bond displacement. [0003] [0004] Nomegestrol is a new type of high-efficiency oral progestogen, which has the characteristics of good contraceptive effect, less toxic and side effects, convenient and safe use. In addition, nomegestrol has a good effect on endometrial displacement (Chinese Pharrnacological Bulletin 2004Nov; 20(11): 1215-7) and reversing the multidrug resistance of drug-resistant breast cancer cell lines (ChinaOncol.March 2002Vol24. No.2). [0005] The existing ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/0045
Inventor 张小元陆何林宋树勇王钱刚黄云生
Owner 丽江映华生物药业有限公司
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