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Estrone raw material medicine impurity, preparation method of estrone raw material medicine impurity, and application of estrone raw material medicine impurity being used as standard substance

A technology of estrone and benzylestrolone, which is applied in the field of medicinal chemistry, can solve the problems of qualitative analysis of estrone and fewer reports on impurity preparation processes, and achieve the effect of improving the quality of finished products and strengthening control

Active Publication Date: 2014-12-24
CHINA RESOURCES ZIZHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is imperative to conduct related research on estrone impurities. At present, there is no requirement for qualitative analysis of estrone in the domestic pharmacopoeia, and there are few reports on the preparation process of estrone.

Method used

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  • Estrone raw material medicine impurity, preparation method of estrone raw material medicine impurity, and application of estrone raw material medicine impurity being used as standard substance
  • Estrone raw material medicine impurity, preparation method of estrone raw material medicine impurity, and application of estrone raw material medicine impurity being used as standard substance
  • Estrone raw material medicine impurity, preparation method of estrone raw material medicine impurity, and application of estrone raw material medicine impurity being used as standard substance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Into a 100 mL one-necked bottle equipped with a reflux condenser, add 2.7 g of estrone, 6.9 g of anhydrous potassium carbonate, 50 mL of DMF and 2.05 g of benzyl bromide. Stir at room temperature for 24h. The reaction solution was introduced into 500 mL of ice water, and filtered to obtain 2.1 g of Zener yellow solid 3-benzylestradiolone.

Embodiment 2

[0017] In a 250mL dry three-necked bottle equipped with a thermometer and a condenser, add 683mg of magnesium chips, a small amount of iodine and 20mL of anhydrous tetrahydrofuran. Stir at room temperature under nitrogen protection, and add 0.01 mL of dibromomethane into the reaction flask. Heating to reflux under vigorous stirring, the reddish-brown color of iodine receded and the reaction solution turned gray, indicating that the reaction was initiated, and 8.0 g of 4-diphenyl bromide was continued to be added dropwise. Continue to reflux for 45 min after the dropwise addition.

[0018] The reaction solution was cooled to room temperature, and a solution of 3-benzylestradiolone (5.41 g) in tetrahydrofuran (30 mL) was added dropwise, and stirring was continued for 6 h after the addition was completed. A sufficient amount of saturated ammonium chloride solution was added dropwise to destroy the reaction, filtered, and the organic phase was separated and concentrated to drynes...

Embodiment 3

[0020] Put 4.5g of 3-benzyl-17-(4'-phenylphenyl)-estra-1,3,5(10)-triene-3,17β-diol into the reaction bottle, 30mL tetrahydrofuran, 0.2g palladium Carbon was replaced with hydrogen and stirred overnight at room temperature. Filtrate, evaporate the filtrate to dryness, and purify by column chromatography to obtain 3 g of light yellow solid 17-(4'-phenylphenyl)-estra-1,3,5(10)-triene-3,17-di-ol .

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Abstract

The invention relates to a novel impurity which is generated in an estrone synthesis process, and a preparation method and application of the novel impurity. The impurity is 3-benzyl-17-(4'-phenyl phenyl)-estra-1,3,5(10), 16,17 tetraalkene. The preparation method comprises the following steps: firstly, protecting three hydroxys of estrone, then performing grignard addition with 4-diphenyl bromine, further performing deprotection on the three hydroxys, and finally dehydrating so as to obtain the impurity. The method is economic and simple. The compound provided by the invention can be used as a standard substance for impurity control in an estrone production process.

Description

technical field [0001] The invention relates to a new related substance in the production process of estrone, its synthesis method and application, and belongs to the field of medicinal chemistry. Background technique [0002] Estrone is a sex hormone that can be detected in the urine of pregnant horses or pregnant women, and also exists in the ovaries or follicular fluid of other pregnant animals and the placenta of women. Due to the limitations of its existence and production, estrone is now mostly prepared by artificial synthesis. [0003] Estrone is an important intermediate for the synthesis of estradiol, ethinyl estradiol, estradiol cypionate and other estrogen drugs and 19-nor steroid drugs. [0004] With the improvement of domestic and foreign testing levels and the improvement of people's requirements for the quality of drugs, higher requirements have been put forward for estrone. Therefore, it is imperative to conduct related research on estrone impurities. At pr...

Claims

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Application Information

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IPC IPC(8): C07J1/00G01N30/02
Inventor 蒋盛铭侯刚孟琳褚国彪
Owner CHINA RESOURCES ZIZHU PHARMA
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