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Process for preparing desogestrel

A technology of desogestrel and its compound, which is applied in the field of preparation of the compound desogestrel, can solve the problems of difficult separation and purification, reduced practical significance, and many reaction by-products, and achieves convenient purification, short reaction route, and improved quality and the effect of the yield

Active Publication Date: 2009-06-03
湖南科益新生物医药有限公司
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Problems solved by technology

Apparently, this synthetic route is also relatively long, and the biketalization of the 3,17 diketone group of compound 17 has the problem of poor selectivity, many reaction by-products, and difficult separation and purification, resulting in a low yield. The hydroxyl group at position 1 and the hydroxyl group at position 17 of compound 15 were oxidized twice using CrO 3 It is an oxidizing agent, which brings inconvenience to post-processing and reduces the practical significance of this route

Method used

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  • Process for preparing desogestrel
  • Process for preparing desogestrel
  • Process for preparing desogestrel

Examples

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Embodiment Construction

[0054] The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention. Unless otherwise specified, the weight-to-volume ratio mentioned in the examples refers to the ratio of the weight of the solid to the volume of the liquid (1:1 is 1 g of solid to 1 ml of liquid).

[0055] With 11α-hydroxyl-18-methyl-estr-4-ene-3,17-dione as the starting material (with 18-methyl-estr-4-ene-3,17-dione as the substrate , obtained by transformation with Rhizopus niger (from Institute of Microbiology, Chinese Academy of Sciences. Yield 39%, melting point: 189-192° C., [α]=-10°) followed by the following steps to prepare desogestrel.

[0056] (1) 3,3-ethylene disulfide-11α-hydroxyl-18-methyl-estr-4-en-17-one (compound 3)

[0057] Add glacial acetic acid (75ml) into the reaction vessel, start stirring, put in compound 2 (15g, 49.60mmol) and ethanedithiol (5.0ml, 59.66mmol), adjust the temperature to 25°C, and add 4.5ml of bor...

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Abstract

The invention provides a process for preparing desogestrel. Taking 11Alpha-oxhydryl-18-methyl-estr-4-ene-3, 17-diketone as an initiator in the process, desogestrel is obtained through seven reaction steps as follows: (1) 3-carbonyl is processed through dithio ketal protection to obtain a compound 3; (2) 17-carbonyl is processed through dibasic alcohol ketal protection to obtain a compound 4; (3) 3-thioketal is eliminated through a Birch reduction reaction to obtain a compound 5; (4) 11Alpha-oxhydryl is oxidized to obtain a compound 6; (5) 11-carbonyl is processed through a Wittig reaction to obtain a compound 7; (6) 17-ketal is de-protected through hydrolyzation to obtain a compound 8; and (7) 17-carbonyl is processed through ethynation to obtain a target compound. The process for preparing desogestrel has short reaction route, obtains products with higher purity quotient in high yield and high selectivity, and has the advantages of simple operation, safety and convenient purification. Furthermore, the invention is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound. Specifically, it relates to a preparation method of the compound desogestrel. Background technique [0002] Desogestrel (Desogestrel) has another name called desogestrel, and its chemical name is 13β-ethyl-11-methylene-18,19-dinorgestrel-4-en-20-yne-17β-alcohol ( 13β-Ethyl-11-methylene-18, 19-dinorpregn-4-en-20-yn-17β-o1), the structural formula is shown in formula (I): [0003] [0004] Desogestrel is a powerful progestogen, which is characterized by no androgen and estrogen activity, and has a significant ovulation inhibitory effect. It is widely used as a contraceptive in clinical practice. Its effect is reliable, the cycle is well controlled, and it does not reduce plasma density. Lipoprotein (HDL), beneficial to lipid metabolism, without side effects such as weight gain and androsis. [0005] The preparation method of desogestrel is a lot, and U.S. Patent (US3927046) disclo...

Claims

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Application Information

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IPC IPC(8): C07J1/00A61P15/18
CPCY02P20/55
Inventor 高建永王永斋
Owner 湖南科益新生物医药有限公司
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