Preparation method of high-purity testosterone undecanoate

A high-purity technology of testosterone undecanoate, applied in the field of steroid drug preparation, can solve the problems of large amount of waste water, high cost of raw materials and low purity of testosterone undecanoate, etc., and achieves the effects of low solvent cost and easy handling

Pending Publication Date: 2022-02-11
湖北竹溪人福药业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problems in the prior art that the purity of testosterone undecanoate is not high, the cost of raw and auxiliary materials is high, the amount of waste water is large, and the cost of waste water treatment is high, the present invention proposes a method for preparing high-purity testosterone undecanoate

Method used

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  • Preparation method of high-purity testosterone undecanoate
  • Preparation method of high-purity testosterone undecanoate
  • Preparation method of high-purity testosterone undecanoate

Examples

Experimental program
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Effect test

Embodiment 1

[0022] (1) Pump 500g of dichloromethane and 100g of triethylamine into the reaction bottle, then add 100g of testosterone, stir evenly, start to add 200g of undecanoyl chloride dropwise, after the dropwise addition, keep the reaction at 0°C for 2 hours, monitor by TLC until the raw materials react completely;

[0023] (2) After the reaction of the raw materials in step (1), add 100g of 6N hydrochloric acid solution and stir for 40min, let it stand for 15min, and remove the water layer; wash the dichloromethane layer with water 3 times until neutral, each time with 200ml of water; 35°C under negative pressure Concentrate dichloromethane until it is concentrated without solvent; pump in 100g of methanol, stir and cool down to 0°C, and crystallize for 4h; suction filter, drain and discharge to obtain 153g of crude testosterone undecanoate;

[0024] (3) Add 800g of methanol, 3g of activated carbon, and 153g of crude testosterone undecanoate prepared in step (1) into the reaction f...

Embodiment 2

[0026] (1) Pump 600g of dichloromethane and 150g of triethylamine into the reaction bottle, then add 100g of testosterone, stir evenly, start to add 300g of undecanoyl chloride dropwise, after the dropwise addition, keep the reaction at 5°C for 1 hour, monitor by TLC until the raw materials react completely;

[0027] (2) After the reaction of the raw materials in step (1), add 120g of 6N hydrochloric acid solution and stir for 30min, let it stand for 20min, and remove the water layer; wash the dichloromethane layer twice to neutral, each time with 300ml of water; 40℃ negative pressure Concentrate dichloromethane until it is concentrated without solvent; pump in 150g of methanol, stir and cool down to -5°C, and crystallize for 2h; suction filter, drain and discharge to obtain 155g of crude testosterone undecanoate;

[0028] (3) Add 1000g of methanol, 5g of activated carbon, and 155g of crude testosterone undecanoate obtained in step (2) into the reaction flask, heat up to reflu...

Embodiment 3

[0030] (1) Pump 550g of dichloromethane and 125g of triethylamine into the reaction bottle, then add 100g of testosterone, stir evenly, start to add 250g of undecanoyl chloride dropwise, after the dropwise addition, keep the reaction at 2.5°C for 1.5h, monitor by TLC until the raw material Complete response;

[0031] (2) After the reaction of the raw materials in step (1), add 110g of 6N hydrochloric acid solution and stir for 35 minutes, let it stand for 17 minutes, and remove the water layer; wash the dichloromethane layer with water twice to neutral, each time with 250ml of water; 37 ℃ negative pressure Concentrate dichloromethane until it is concentrated without solvent; pump in 125g of methanol, stir and cool down to -2.5°C, and crystallize for 3h; suction filter, drain and discharge to obtain 152g of crude testosterone undecanoate;

[0032] (3) Add 900g of methanol, 4g of activated carbon, and 152g of crude testosterone undecanoate prepared in step (2) into the reaction ...

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Abstract

The invention discloses a preparation method of high-purity testosterone undecanoate, belonging to the technical field of steroid medicine preparation. According to the method, testosterone is used as a raw material, and esterification and purification are carried out, so the high-purity testosterone undecanoate with a high purity of larger than or equal to 99.5% is obtained; and a technical route is high in preparation efficiency, and the obtained product is good in quality and high in yield. The preparation method disclosed by the invention solves the problems that related raw and auxiliary materials are seriously polluted, production wastewater is difficult to treat, large-scale batch production is not facilitated, and the obtained testosterone undecanoate is low in purity and relatively more in impurities in the prior art.

Description

technical field [0001] The invention belongs to the technical field of steroid medicine preparation, and in particular relates to a preparation method of high-purity testosterone undecanoate. Background technique [0002] Testosterone Undecanoate (Testosterone Undecanoate) chemical name: 17β-hydroxyandrost-4-en-3-one undecanoate, white crystal or crystalline powder; molecular formula is C 30 h 48 o 3 , for the treatment of primary or secondary testicular hypofunction; boy constitutional delay of puberty; palliative treatment of breast cancer metastasis; adjuvant treatment of aplastic anemia; middle-aged and elderly partial androgen deficiency syndrome. [0003] The existing production technology of testosterone undecanoate generally uses benzene, toluene, pyridine, and undecanoic acid as raw and auxiliary materials to synthesize testosterone undecanoate. The raw materials and auxiliary materials related to this technology are polluted, and the production wastewater is diff...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0025
Inventor 侯海波郑承刚朱保林郑建雄刘林付浩
Owner 湖北竹溪人福药业有限责任公司
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