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Desogestrel preparation method and midbody compound

A technology of desogestrel and steroidal compounds, applied in the direction of steroidal compounds, organic chemistry, etc., can solve the problems of high cost of process route, low purity of desogestrel, unfavorable industrial production, etc., and achieve simple and easy process, The effect of cost reduction and high yield

Inactive Publication Date: 2016-08-31
CHINA RESOURCES ZIZHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The disadvantages of the above preparation method are mainly: the obtained desogestrel has a low purity and does not meet the pharmaceutical standard EP8.0, and further purification is required, resulting in high cost of the process route
At the same time, the Raney nickel catalyst used in the preparation of N-2 compounds is not easy to transport and store, and is a dangerous product, which is not conducive to industrial production

Method used

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  • Desogestrel preparation method and midbody compound
  • Desogestrel preparation method and midbody compound
  • Desogestrel preparation method and midbody compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Preparation of Compound VII

[0040] Distill 50ml of liquid ammonia into the reaction vessel, add 3g (0.43mol) of lithium metal, and react for 0.5 hours at -50-70℃. After dissolving 10g (0.026mol) of compound II in 100ml of tetrahydrofuran, drop it into the reaction In the container, react for 2h, and then slowly add 15ml of absolute ethanol dropwise. After the reaction is completed by thin layer chromatography, slowly rise to room temperature, add 50ml of purified water, precipitate a yellow solid, then filter and dry to obtain compound VII with a weight of 7.2 g, the molar yield is 94.8%.

[0041] MS(m / z): 287.4[M+H] + , 1 H-NMR(CDCl 3 ), δ5.68 (1H, t, 4-CH), δ 2.85 (2H, t, 12-CH 2 ), δ2.67(2H, t, 16-CH 2 ); 13 C-NMR, δ 215.8 (C-17), δ 210.3 (C-11), δ 137.3 (C-5), δ 122.1 (C-4).

Embodiment 2

[0042] Example 2: Preparation of Compound VIII

[0043] Add 200ml (0.2mol) of n-butyllithium / n-hexane solution to 100ml of tetrahydrofuran, slowly inject acetylene gas at 15-30°C for 1 to 2 hours, and then add 10g (0.035mol) of compound VII into the reaction vessel , React at a temperature of 15-30 ℃ for 0.5 to 1 hour, after the completion of the reaction detected by thin layer chromatography, add 20ml saturated ammonium chloride solution and 50ml dichloromethane, extract the organic phase, dry over anhydrous magnesium sulfate, and then reduce pressure Concentrated to obtain compound VIII with a weight of 9.5 g and a molar yield of 87.0%.

[0044] MS(m / z): 314.4[M+H] + , 1 H-NMR(CDCl 3 ), δ 5.67 (1H, t, 4-CH), δ 5.35 (1H, s, 17-OH), δ 3.09 (1H, s, 17-OH), δ 2.89 (2H, t, 12 -CH 2 ); 13 C-NMR, δ219.7(C-11), δ137.7(C-5), δ122.2(C-4), δ84.1(C-20), δ81.1(C-17), δ73 .6(C-22).

Embodiment 3

[0045] Example 3: Preparation of Compound VIII

[0046] 14g (0.125mol) potassium tert-butoxide was added to 100ml of ether, and acetylene gas was slowly introduced at a temperature of 15-30°C for 1 to 2 hours, and then 10g (0.035mol) of compound VII was added to the reaction vessel. React at 30°C for 0.5 to 1 hour. After TLC detects the completion of the reaction, add 20ml of saturated ammonium chloride solution and 50ml of dichloromethane, extract the organic phase, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain compound VIII The weight is 9.1g, and the molar yield is 83.3%.

[0047] MS(m / z): 314.4[M+H] + , 1 H-NMR(CDCl 3 ), δ 5.67 (1H, t, 4-CH), δ 5.35 (1H, s, 17-OH), δ 3.09 (1H, s, 17-OH), δ 2.89 (2H, t, 12 -CH 2 ); 13 C-NMR, δ219.7(C-11), δ137.7(C-5), δ122.2(C-4), δ84.1(C-20), δ81.1(C-17), δ73 .6(C-22).

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Abstract

The invention relates to a novel steroidal compound and application of the novel steroidal compound in a desogestrel preparation process. The novel compound easy to separate is obtained through 17-bit selective ethynylation of 13beta-ethyl pregnane-4, 5-alkene-11, 17-diketone. When the compound is used for preparing desogestrel, simplicity and convenience in operation are achieved, and yield is high.

Description

Technical field [0001] The invention relates to a steroid compound and its application in the process of preparing desogestrel. Background technique [0002] Desogestrel is a potent oral progestin. The progestin activity is 18 times stronger than norethindrone and 1 times stronger than norethindrone. And there is no androgenic and estrogenic activity. The drug has reliable effects and good safety when used for contraception. The composite tablet of the drug and ethinyl estradiol is often used as a long-acting oral contraceptive in clinical practice. [0003] There are many methods for preparing desogestrel. Patent CN201010208944 discloses a method for synthesizing desogestrel. The method uses ethyl triketone compound (I) as a starting material and performs thioketal on the 3-position carbonyl group. Protection and ketal protection of the 17-position carbonyl group to obtain (III), then the Peterson reaction is carried out on the 11-position to construct the 11-position double bon...

Claims

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Application Information

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IPC IPC(8): C07J11/00
Inventor 张冲杨龙蒋彬唐娜邓强耿聪聪
Owner CHINA RESOURCES ZIZHU PHARMA
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