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Preparation method of dienogest

A technology for dienogest and compounds, which is applied in the field of preparation of dienogest, can solve the problems of dark color and low purity of crude products, and achieves the effects of cheap and easy-to-obtain raw materials and reduced production costs.

Active Publication Date: 2021-01-12
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Based on this, it is necessary to provide a preparation method of dienogest, which fundamentally solves the problems of low purity and dark color of the crude product in the acidolysis deprotection process, and greatly simplifies the production process , reducing the production cost of the enterprise

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  • Preparation method of dienogest

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preparation example Construction

[0036] One embodiment of the present invention provides a method for preparing dienogest, comprising the following steps:

[0037] S101: providing a compound of the structure shown in formula (II);

[0038]

[0039] Can adopt existing method to prepare the compound shown in formula (II), do not carry out special limitation here, should be understood as all within the scope of protection of the present invention, preferably adopt following method to make the compound shown in structure of formula (II):

[0040] S1011: providing a compound represented by formula (III);

[0041]

[0042] Existing methods can be used to prepare the compound represented by formula (III), which is not particularly limited here, and should be understood as being within the protection scope of the present invention.

[0043] S1012: reacting the compound represented by the formula (III) with lithium cyanide to prepare the compound with the structure represented by the formula (II);

[0044] ...

Embodiment 1

[0080] (1) Preparation of the compound shown in formula (II), i.e. 17α-cyanomethyl-17β-hydroxyl-5,9-androstadiene-3,17-dione-3,3-ethylene ketal

[0081]

[0082] In the reaction flask, add 120ml of 2.5mol / L n-butyllithium, lower the temperature to below -50°C, add 240ml of tetrahydrofuran, continue to cool down to below -50°C, and start to drop the mixed solution of acetonitrile and tetrahydrofuran (8.0g / 20ml ), the dropwise addition was completed, stirred for 5 minutes, and 17β-hydroxyl-5,9-androstadiene-3,7-dione-3,3-ethylene ketal was added dropwise (source: Hunan Xinhe Xinbio Pharmaceutical Co., Ltd., purity ≥ 99.30%, mono-hetero<0.10%) tetrahydrofuran solution (30g / 100ml), 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 32 g, a yield of 106%, and a purity of 98....

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Abstract

The invention relates to a preparation method of dienogest. The preparation method comprises the following steps: providing a compound with a structure shown as a formula (II); and carrying out an acidolysis deprotection reaction on the compound shown in the formula (II) in an aqueous fluoboric acid solution to prepare a compound with a structure shown in a formula (I). According to the preparation method of the dienogest, the problems of low purity and dark color of a crude product of an acidolysis deprotection process are fundamentally solved, a production process is greatly simplified, andthe production cost of an enterprise is reduced.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method 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 2002 under the product name Climodien. In 2007, dienogest tablets (1 mg) were launched in Japan for th...

Claims

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Application Information

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