Preparation method of dienogest and method for recovering dienogest from dienogest mother liquor

A technology of dienogest and solvent, applied in the field of preparation of dienogest, can solve problems such as low yield, and achieve the effects of reducing three wastes, improving total yield and reducing production cost

Pending Publication Date: 2021-02-19
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some companies use concentrated hydrochloric acid to deprotect the product, and the purity of the crude product is ≥98% after twice recrystallization from acetone, and the yield is only 43.5%, which is very low.

Method used

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  • Preparation method of dienogest and method for recovering dienogest from dienogest mother liquor
  • Preparation method of dienogest and method for recovering dienogest from dienogest mother liquor
  • Preparation method of dienogest and method for recovering dienogest from dienogest mother liquor

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Embodiment 1

[0024] Step 1: Preparation of the shown compound B, namely 17α-cyanomethyl-17β-hydroxy-5,9-androstadiene-3,17-dione-3,3-ethylidene ketal

[0025]

[0026] In the reaction flask, add 150ml of 2.5mol / L n-butyllithium, lower the temperature to below -50°C, add 300ml of tetrahydrofuran, continue to cool down to below -50°C, and start to drop the mixed solution of acetonitrile and tetrahydrofuran (10.0g / 25ml ), the dropwise addition was completed, stirred for 5 minutes, and 17β-hydroxy-5,9-androstadiene-3,7-dione-3,3-ethylene ketal was added dropwise (source: Hunan Xinhe Xinbio Pharmaceutical Co., Ltd., purity ≥ 99.30%, monohetero<0.10%) tetrahydrofuran solution (38g / 125ml), dropwise, temperature control -50 ℃ ~ -90 ℃ for 30 minutes, the reaction is complete, drop dilute hydrochloric acid to terminate the reaction, separate layer, and the organic phase was concentrated under reduced pressure to a pale yellow oil with a weight of 40.5 g, a yield of 106.5%, and a purity of 97.6%. ...

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Abstract

The invention belongs to the technical field of steroid hormone drug preparation, and particularly relates to a preparation method of dienogest and a method for recovering the dienogest from dienogestmother liquor. The preparation method of the dienogest comprises the following steps: dissolving 17 alpha-cyanomethyl-17 beta-hydroxyl-5, 9-androstane diene-3, 17-diketone-3,3-ethyleneketal, adding fluoboric acid, carrying out acidolysis to remove protection, and after the reaction is completed, carrying out treatment to obtain the dinogestrol. The method for recovering the dienogestrol from thedienogestrol mother liquor comprises the following steps: dissolving the dienogestrol with a solvent to obtain the dienogestrol mother liquor, adding perchloric acid or concentrated hydrochloric acid,reacting for a period of time, heating to 45-55 DEG C, concentrating under reduced pressure, removing part of the solvent by concentrating until a solid is separated out, stopping concentrating, cooling, continuing the reaction, and treating to obtain the dienogestrol. The product provided by the invention has high purity and high yield.

Description

technical field [0001] The invention belongs to the technical field of preparation of steroid hormone drugs, and in particular relates to a method for preparing dienogest and a method for recovering dienogest from mother liquid of dienogest. Background technique [0002] Dienogest is a progestogen drug with the chemical name 17α-cyanomethyl-17β-hydroxyl-13β-methylsterane-4,9-dien-3-one, released in 1995 The compound preparation (2mg+0.03mg) of ethinyl estradiol and ethinyl estradiol was launched in Germany as a contraceptive, and it was launched in Australia in 2007 under the trade name Valette. In 2001, the compound preparation of dienogest and estradiol valerate (containing 2 mg of dienogest and 1 or 2 mg of estradiol valerate) was launched in Germany by Schering Company, and it was used for women who had been menopausal for more than one year. Hormone replacement therapy for hormone deficiency. It was launched in Denmark, France, Belgium and other European countries in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0094
Inventor 孙晓明杨文杰曾春玲靳志忠
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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