Preparation method of prostaglandin A1

A technology of prostaglandin and alprostadil, applied in the field of preparation of prostaglandin A1, can solve the problems of complicated post-processing, poor separation effect, long reaction time and the like, and achieve the effects of improving product production efficiency, easy operation and mild conditions

Active Publication Date: 2015-05-06
SHAANXI DASHENG PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this is that the reaction time is too long, there are many side reactions, the post-treatment is complicated, and the separation effect is poor.

Method used

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  • Preparation method of prostaglandin A1
  • Preparation method of prostaglandin A1
  • Preparation method of prostaglandin A1

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 500 mg of alprostadil and 5 ml of tetrahydrofuran into the reaction flask, stir for 10 minutes, pass in hydrogen chloride gas for 20 minutes, raise the temperature to 55-65° C., and react for 5 hours. Add 0.025 g of activated carbon and keep it warm for 30 minutes, heat filter, evaporate the solvent from the filtrate under reduced pressure, add 2.5ml of isopropanol to the residual species and raise the temperature to 40°C, slowly add 15ml of petroleum ether dropwise, slowly cool down to below 10°C, and stand for crystallization for 5 hours, pump 313 mg of light yellow solid was obtained by filtration, the yield was 66%, and the purity was greater than 98.5%. Example 2

Embodiment 2

[0016] Add 1 g of alprostadil and 10 ml of tetrahydrofuran into the reaction flask, stir for 10 minutes, pass in hydrogen chloride gas for 30 minutes, raise the temperature to 55-65° C., and react for 6.5 hours. Add 0.05 g of activated carbon and keep it warm for 30 minutes, heat filter, evaporate the solvent from the filtrate under reduced pressure, add 5 ml of isopropanol to the residual species and raise the temperature to 40 ° C, slowly add 30 ml of petroleum ether dropwise, slowly cool down to below 10 ° C, and stand overnight for crystallization, and suction filter to obtain Light yellow solid 664mg, yield 70%, purity greater than 98.5.

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Abstract

The invention provides a preparation method of prostaglandin A1. The preparation method comprises the steps of adding alprostadil and tetrahydrofuran at room temperature and stirring, filling hydrogen chloride gas, heating to 55-65 DEG C, reacting for 5-7 hours, adding active carbon and decolorizing for 30min, filtering to remove the active carbon, pressurizing mother liquor to remove a solvent, adding isopropyl alcohol to residual materials, dropping petroleum ether at 40-45 DEG C, slowly reducing temperature to be less than 10 DEG C, standing and crystallizing for 5-6 hours, and carrying out suction filtering to obtain a white solid prostaglandin A1. The preparation method implements an elimination reaction under an acid condition, and is moderate in reaction condition; the preparation method implements purification by recrystallization instead of chromatographic column separation, and is simple and quick to operate, high in product purity and is favorable for research on alprostadil.

Description

technical field [0001] The invention provides a preparation method of prostaglandin A1. Background technique [0002] Prostaglandin is an active substance composed of unsaturated fatty acids that exists in animals and humans and has various physiological functions. It was discovered by Uler in 1930. According to their structure, prostaglandins are divided into A, B, C, D, E, F, G, H, I and other types. Different types of prostaglandins have different functions, such as prostaglandin E can relax bronchial smooth muscle and reduce ventilation resistance; while prostaglandin F has the opposite effect. [0003] Alprostadil, also known as prostaglandin E1, English name prostaglandin E1. Molecular formula is C 20 h 34 o 5 , the chemical name is 11(a), 15(s)-dihydroxy-9-keto-13-reprostenic acid, which is recorded in usp and bp, and is a drug recorded in the Pharmacopoeia of the People's Republic of China 2010 edition. The structural formula is: [0004] [0005] The drug is...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07C405/00
Inventor薛朝允杨刚利
OwnerSHAANXI DASHENG PHARMA TECH