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Ergometrine preparation method

A technology of ergonovine and lysergic acid, which is applied in the direction of organic chemistry, can solve the problems of low yield, and achieve the effects of high yield, mild reaction conditions, and increased yield

Inactive Publication Date: 2017-06-20
CHENGDU BRILLIANT PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Ergometrine is the main raw material of ergonovine maleate. Its preparation method mainly includes CN201610791636, and two paths are recorded in this patent application; path 1: under the condition of the presence of condensing agent HBTU, lysergic acid and L- Aminopropanol directly carries out condensation reaction to prepare ergonovine, but the productive rate is relatively low, only 23.1%; Path 2: by another synthetic method, lysergic acid halide is first produced by amidation reaction with L-aminopropanol. For ergonovine, this path can increase the yield to 41.9%. Although the yield of path two has increased by about 0.8 times, the overall yield is still at a relatively low level

Method used

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  • Ergometrine preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]Accurately weigh lysergic acid (10g, 37.3mmol), L-aminopropanol (2.8~7g, 37.3~93.25mmol), add 150mLTHF and stir, then slowly add triethylamine (7.5~18.75g, 74.6~186.5mmol), T3P (50%wt ethyl acetate solution, 23.7~71.1g, 37.3~111.9mmol). The above reaction mixture was stirred at room temperature for 6 hours, diluted with water (300mL), the organic phase was separated, the aqueous phase was extracted with dichloromethane (150mL x 2), and the combined organic phases were washed twice with saturated sodium chloride solution, 50mL each time . Fully dried with anhydrous sodium sulfate, concentrated to dryness to obtain an off-white solid, this solid was beaten with dichloromethane (50mL) to obtain 9.8g ergonovine, which was a white solid with a yield of 81%, and the optical purity was analyzed by HPLC. 98.6%.

Embodiment 2

[0035] Accurately weigh lysergic acid (10g, 37.3mmol), L-aminopropanol (2.8g, 37.3mmol), add 150mL THF and stir, then slowly add N,N-diisopropylethylamine ( 9.6 g, 74.6 mmol), T3P (50% wt in ethyl acetate, 23.7 g, 37.3 mmol). The above reaction mixture was stirred at room temperature for 6 hours, diluted with water (300mL), the organic phase was separated, the aqueous phase was extracted with ethyl acetate (150mL x 2), and the combined organic phases were washed twice with saturated sodium chloride solution, 50mL each time . Fully dried with anhydrous sodium sulfate, concentrated to dryness to obtain an off-white solid, and this solid was beaten with dichloromethane (50mL) to obtain 10.8g ergonovine, which was a white solid with a yield of 89.3%, and the optical purity was analyzed by HPLC. 99.4%.

Embodiment 3

[0037] Accurately weigh lysergic acid (10g, 37.3mmol), L-aminopropanol (2.8g, 37.3mmol), add 150mL THF and stir, then slowly add pyridine (5.9g, 74.6mmol), T3P ( 50% wt ethyl acetate solution, 23.7 g, 37.3 mmol). The above reaction mixture was stirred at room temperature for 6 hours, diluted with water (300 mL), the organic phase was separated, the aqueous phase was extracted with methyl tetrahydrofuran (150 mL x 2), and the combined organic phases were washed twice with saturated sodium chloride solution, 50 mL each time. Fully dried with anhydrous sodium sulfate, concentrated to dryness to obtain an off-white solid, this solid was beaten with dichloromethane (50mL) to obtain 10g of ergonovine, which was a white solid with a yield of 82.6%, and an optical purity of 98.9% by HPLC analysis. %.

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Abstract

The invention provides an ergometrine preparation method. Under an alkaline condition, sphacelic acid and L-amino propanol react to prepare ergometrine by using T3P as a condensing agent. By means of the method disclosed by the invention, the ergometrine yield is greatly improved, the problem of relatively lower yield in the prior art is solved, and economical benefit of the industry is improved.

Description

technical field [0001] The invention relates to a preparation method of a chemical intermediate or a medicinal compound, in particular to a preparation method of ergonovine. Background technique [0002] The chemical structure of ergonovine is as follows: [0003] [0004] As the most commonly used clinically important drug in obstetrics and gynecology, ergometrine can directly act on uterine smooth muscle with a strong and long-lasting effect. It is often used in the effective treatment of the third stage of labor in childbirth and the prevention or treatment of postpartum hemorrhage and bleeding caused by uterine contraction retardation . In 1918, Stoll isolated the first pure ergot alkaloid (ergotamine) from ergot extracts. In 1935, Dudley et al. discovered the second biologically active ergot alkaloid, namely ergonovine. Sandoz Corporation of Japan successfully developed and launched the product in 1938. Since 1998, ergonovine has been included in the National Esse...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D457/06
CPCC07D457/06
Inventor 刘冠锋黄浩喜吴鲜财陈垌晖任俊锋李英富苏忠海
Owner CHENGDU BRILLIANT PHARMA CO LTD
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