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Propranolol enantiomer resolution method

A technology of propranolol and enantiomers, which is applied in the field of pharmaceutical preparation, can solve problems such as unsatisfactory chiral extraction of enantiomers, and achieve the effects of low toxicity, low price and easy availability of raw materials in the production process

Active Publication Date: 2014-02-26
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, except for a few extraction systems that have satisfactory enantiomeric resolution, the chiral extraction of most enantiomers is not ideal

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0022] Take by weighing 100g (R, S)- propanol hydrochloride bulk drug and add 2500ml water to dissolve, add 2 times of equivalent 20% sodium hydroxide solution and carry out neutralization reaction, static, filter, wash, dry to obtain (R, S) - Propranol; the resolving agent dehydroabietic acid and the above-mentioned propranolol prepared according to the molar ratio of 1:1 feed intake, with methanol as a solvent, reacted for 1h at 30 ° C, after the reaction was completed - Cool down and crystallize at 5°C for 5 hours, filter, wash, and dry to obtain propranolol dehydroabietate; add 1500ml of methanol to the above-prepared propranolol dehydroabietate to fully dissolve, then add 3 Double the equivalent of 20% sodium hydroxide solution to react for 30 minutes, dry to obtain the crude product of S(-)-propranolol, add it to the crude product of S(-)-propranolol, fully dissolve in 2500ml of water, filter, wash and dry 41.3 g of S(-)-propranolol was obtained, and the product purity w...

Embodiment 2

[0024] Take by weighing 100g (R, S)- propanol hydrochloride crude drug and add 2500ml water to dissolve, add 3 times of equivalent 35% sodium hydroxide solution and carry out neutralization reaction, static, filter, wash, dry to obtain (R, S) -propranol; the resolving agent dehydroabietic acid and the above-mentioned propranolol prepared according to the molar ratio are 1.3:1 feeding intake, with methanol as a solvent, reacted for 3h at 25°C, after the reaction finished at 5 Cool down and crystallize at ℃ for 6 hours, filter, wash, and dry to obtain propranolol dehydroabietate; add 1500ml methanol to the above-prepared propranolol dehydroabietate to fully dissolve, add 3 times Equivalent 35% sodium hydroxide solution was reacted for 20min, dried to obtain the crude product of S(-)-propranolol, added to the crude product of S(-)-propranolol, fully dissolved in 2500ml water, filtered, washed and dried to prepare Obtain the S(-)-propranolol of 37.1g, product purity is 90.0%.

Embodiment 3

[0026] Take by weighing 100g (R, S)- propranolol hydrochloride crude drug and add 2500ml water to dissolve, add 1 times of equivalent 10% sodium hydroxide solution and carry out neutralization reaction, stand still, filter, wash, dry to obtain (R, S) -propranol; the resolving agent dehydroabietic acid and the above-mentioned propranolol prepared are fed according to the molar ratio of 1.3:1, and methanol is used as a solvent to react for 2h at 35°C. Cool down and crystallize at ℃ for 6 hours, filter, wash, and dry to obtain propranolol dehydroabietate; add 2000ml methanol to the above-prepared propranolol dehydroabietate to fully dissolve, add 3 times Equivalent 10% sodium hydroxide solution was reacted for 45min, dried to obtain the crude product of S(-)-propranolol, added to the crude product of S(-)-propranolol, fully dissolved in 2500ml water, filtered, washed and dried to prepare Obtain the S(-)-propranolol of 23.2g, product purity is 96.8%.

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Abstract

The present invention discloses a propranolol enantiomer resolution method, which comprises: (1) carrying out neutralization alkalization on a (R,S)-propranolol hydrochloride bulk drug by using an alkali solution to prepare (R,S)-propranolol; (2) adopting dehydroabietic acid as a resolution agent, and carrying out a reaction of the (R,S)-propranolol prepared in the step (1) and the dehydroabietic acid in an organic solvent to prepare a propranolol dehydroabietate; and (3) adding the propranolol dehydroabietate in the step (2) to an organic solvent to completely dissolve, and adding a certain amount of an alkali solution to carry out alkalization to prepare the high purity S(-)-propranolol. The propranolol enantiomer resolution method has characteristics of easily available raw materials, low price, high yield, high product purity, less pollution and simple process, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, in particular to a method for splitting propranolol enantiomers by using dehydroabietic acid. Background technique [0002] Propranolol (propranolol) was first developed by the British ICI company. It is an important β-receptor blocker and is mainly used to treat cardiovascular and cerebrovascular diseases such as hypertension, arrhythmia and angina pectoris. It is used clinically Racemate, the pharmacological activity of the two enantiomers is very different. Experiments have shown that S(-)-propranolol can block β-receptors about 100 times more than R(+)-propranolol, and has a longer half-life in the blood; R-enantio The body can treat hyperthyroidism and the S-enantiomer has a significant effect of releasing adrenaline; in addition, R(+)-propranolol also has a contraceptive effect and can be used as an effective contraceptive. Therefore, administration in the form of racemate n...

Claims

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Application Information

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IPC IPC(8): C07C217/30C07C213/10
Inventor 葛利杨克迪赵琼琼郭亮池蓝柳凤夏璠霍姣苏何盟刘师师鲍安先黄好
Owner GUANGXI UNIV
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