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Preparation method of exemestane

A technology for exemestane and methylene androstadienone ethylene glycol ketal, which is applied in the field of anticancer drugs, can solve the problems of complex system, large environmental pollution, low yield and the like, and achieves a simple process route and easy raw materials. The effect of obtaining, high yield

Inactive Publication Date: 2018-03-23
SHAANXI QIYUAN TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above two methods have their own advantages and disadvantages. The method ① yield is too low and the system is complicated; the method ② raw materials and Jones reagent are more expensive and pollute the environment, so they are not suitable for industrial production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] The preparation method of exemestane of the present invention comprises the following steps:

[0014] The first step, the preparation of 6-methylene androstienone ethylene glycol ketal, under the protection of nitrogen, successively add paraformaldehyde, dimethylamine hydrochloride and isoamyl alcohol into a four-necked reaction flask, and heat Reflux with water for 2 hours, then add androsadienone ethylene glycol ketal, heat and stir the reaction at 140 degrees, track and detect the reaction by high-performance liquid chromatography, after 15 hours of reaction, cool to room temperature, add distilled water to wash, separate layers and wash with anhydrous sulfuric acid Magnesium was dried, the solvent was recovered under reduced pressure, and a white solid was obtained by silica gel column chromatography;

[0015] In the second step, the preparation of exemestane, under the protection of nitrogen, sequentially add 6-methylene androstienone ethylene glycol ketal, p-tolue...

Embodiment 2

[0017] The preparation method of exemestane of the present invention comprises the following steps:

[0018] The first step, the preparation of 6-methylene androstienone ethylene glycol ketal, under the protection of nitrogen, successively add paraformaldehyde, dimethylamine hydrochloride and isoamyl alcohol into a four-necked reaction flask, and heat Reflux with water for 2 hours, then add androsadienone ethylene glycol ketal, heat and stir the reaction at 140 degrees, track and detect the reaction by high-performance liquid chromatography, after 15 hours of reaction, cool to room temperature, add distilled water to wash, separate layers and wash with anhydrous sulfuric acid Magnesium was dried, the solvent was recovered under reduced pressure, and a white solid was obtained by silica gel column chromatography;

[0019] In the second step, the preparation of exemestane, under the protection of nitrogen, sequentially add 6-methylene androstienone ethylene glycol ketal, p-tolue...

Embodiment 3

[0022] The preparation method of exemestane of the present invention comprises the following steps:

[0023] The first step, the preparation of 6-methylene androstienone ethylene glycol ketal, under the protection of nitrogen, successively add paraformaldehyde, dimethylamine hydrochloride and isoamyl alcohol into a four-necked reaction flask, and heat Reflux with water for 2 hours, then add androsadienone ethylene glycol ketal, heat and stir the reaction at 140 degrees, track and detect the reaction by high-performance liquid chromatography, after 15 hours of reaction, cool to room temperature, add distilled water to wash, separate layers and wash with anhydrous sulfuric acid Magnesium was dried, the solvent was recovered under reduced pressure, and a white solid was obtained by silica gel column chromatography;

[0024] In the second step, the preparation of exemestane, under the protection of nitrogen, sequentially add 6-methylene androstienone ethylene glycol ketal, p-tolue...

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PUM

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Abstract

The invention discloses a preparation method of exemestane, relates to the field of an anti-cancer drug, and particularly relates to exemestane. The preparation method of the exemestane includes stepsof preparing 6-methylene androstenone glycol acetone; under the nitrogen protection, orderly adding paraformaldehyde, dimethylamine hydrochloride and isoamyl alcohol in a four-opening reaction bottle; heating and backflowing water for 2 hours; adding androstenone glycol acetone, preserving temperature and stirring at 140 DEG C; performing high performance liquid chromatography tracking detectionreaction; finishing reaction for 15 hours, and cooling to room temperature; adding distilled water to wash; after layering, drying it by anhydrous magnesium sulfate, depressurizing and recycling solvent; performing column chromatography on silica gel to obtain white solid; secondly, preparing exemestane; orderly adding 6-methylene androstenone glycol acetone, p-toluenesulfonic acid and tetrahydrofuran in a four-opening bottle under the nitrogen protection. The preparation method is simple in technical route, easy to obtain raw materials, low in cost, high in yield, and overcomes the defects existed in the prior art; therefore, the preparation method is applicable to industrial production.

Description

technical field [0001] The invention relates to the field of anticancer drugs, in particular to a preparation method of exemestane. Background technique [0002] Exemestane, chemically known as 6-methyleneandrost-1,4-diene-3,17-dione, is a novel irreversible aromatase inhibitor with a mechanism of action different from that of antiestrogens It is clinically used in the treatment of metastatic breast cancer and advanced breast cancer in postmenopausal women, with definite curative effect, good tolerance and less side effects. [0003] The synthetic methods of exemestane mainly include: ①Using androst-4-ene-3,17-dione as raw material, Mannich reaction occurs with dimethylamine hydrochloride and paraformaldehyde to prepare 6-methylene oxidative dehydrogenation by oxidants such as DDQ or chlorobenzoquinone to obtain exemestane; ② using dehydrotestosterone as raw material, first react with dimethylamine hydrochloride and paraformaldehyde to produce 6-methylene dehydrotestostero...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0011
Inventor 张淑芬
Owner SHAANXI QIYUAN TECH DEV
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