Synthetic method of ulipristal acetate

A technology of ulipristal acetate and a synthesis method, applied in the directions of steroids, organic chemistry, etc., can solve the problems of unsuitability for large-scale production, unfriendly reagents, troublesome post-processing, etc., and achieves low cost, operation and post-processing. Convenience and simple route

Active Publication Date: 2013-01-16
SUZHOU KANGRUN PHARMA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The purpose of the present invention is to provide a new method for the synthesis of ulipristal acetate, which avoids the disadvantages of using highly toxic and environmentally unfriendly reagents in the existing route, complex operation, troublesome post-treatment, and unsuitable for large-scale production.

Method used

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  • Synthetic method of ulipristal acetate
  • Synthetic method of ulipristal acetate
  • Synthetic method of ulipristal acetate

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Embodiment

[0035] The first step: the synthesis of compound 27

[0036] Add raw material 12 (3.14 g, 10 mmol) and potassium tert-butoxide (11.2 g, 100 mmol) to a mixed solvent of 150 ml ethylene glycol dimethyl ether and 63 ml tert-butanol at room temperature and stir to dissolve; Under nitrogen protection, a solution of p-toluenesulfonylmethyl isocyanide (3.9 g, 20 mmol) in 50 ml of ethylene glycol dimethyl ether was slowly dropped in, and the mixture was stirred at room temperature until the reaction was complete. After adding 100 ml of saturated ammonium chloride aqueous solution, the reaction solution was separated, and the aqueous layer was extracted once with ethyl acetate. The organic layers were combined, washed with water and brine respectively, dried over anhydrous magnesium sulfate, filtered and spin-dried to obtain a brown oily crude product, which was subjected to column chromatography to obtain light yellow oily compound 27 (2.5 g, yield 75%).

[0037] 1 HNMR (400MHz, CDC...

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Abstract

The invention relates to a synthetic method of ulipristal acetate. According to the method, 3, 3-(ethylenedioxy group) steroidal estrogen-5(10), 9(11)-diene17-ketone is used as a raw material and reacted with tosylmethyl isocyanide under the condition of alkalinity to obtain 3, 3-(ethylenedioxy group) steroidal estrogen-5(10), 9(11)-diene17-cyanogen; the 3, 3-(ethylenedioxy group) steroidal estrogen-5(10), 9(11)-diene17-cyanogen and a methyl grignard reagent are reacted to obtain methyl ketone; the methyl ketone and trialkyl ester phosphate are reacted in the oxidation environment under alkalinity conditions to obtain 3, 3-ethylenedioxy group-17 alpha-hydroxyl-19-norpregna-5(10), 9(11)-diene-20-ketone; the 3, 3-ethylenedioxy group-17 alpha-hydroxyl-19-norpregna-5(10), 9(11)-diene-20-ketone uses ethylene glycol to protect 20-carbonyl under the acid catalysis to obtain a key intermediate; and the intermediate is synthesized into a target product through four steps of reaction by means of known methods. The synthetic method is concise in paths, easy to operate, convenient to post-process, low in cost, high in total yield and easy to amplify, and raw materials are easily obtained.

Description

technical field [0001] The invention relates to a new method for synthesizing ulipristal acetate. Background technique [0002] Ulipristal acetate (ulipristal acetate, 1), the chemical name is 17α-acetoxy-11β(4-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20 - Diketone is a selective progesterone receptor modulator researched and developed by French HRA pharmaceutical company. In May 2009, it was approved by the European Commission for marketing under the product name EllaOne. In August 2010, it was approved by the U.S. FDA to go on the market. The trade name is Ella, which can be used as an emergency contraceptive for women within 120 hours of unprotected sexual intercourse or contraceptive failure. This product is the first and only drug specially designed and used for emergency contraception that has been approved worldwide so far. The main mechanism of its contraceptive effect may be to inhibit or delay ovulation. In addition, ulipristal acetate is being studied for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
Inventor 徐卫良储玉平扈田进徐炜政
Owner SUZHOU KANGRUN PHARMA
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