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Choleretic drug alibendol preparation method

A technology of alibendol and choleretic drugs, which is applied in the field of drug synthesis, can solve the problems of harsh reaction conditions, low yield, and difficulty in realizing industrial production in the synthesis route, and achieve the effects of less pollution, simple synthesis steps, and alleviation of environmental problems

Inactive Publication Date: 2019-06-04
辽宁博美医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The reaction conditions of the above synthetic route are harsh, and the yield is low, so it is difficult to realize industrial production

Method used

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  • Choleretic drug alibendol preparation method
  • Choleretic drug alibendol preparation method

Examples

Experimental program
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Effect test

Embodiment example 1

[0022] Preparation of methyl 2-hydroxy-3-methoxybenzoate (3): 7.6g of 2-hydroxy-3-methoxybenzaldehyde (2) and 1g of vanadium pentoxide were placed in a dry container with a reflux device In a three-neck round bottom flask, add 100ml of methanol, then add 30ml of 50% hydrogen peroxide, and stir at room temperature for 3 hours. After the reaction, filter and distill the filtrate to recover methanol, add 50ml of dichloromethane to wash twice, combine the dichloromethane phase, concentrate the solvent to dryness, and obtain 7.8g of a dark paste solid. The crude product was heated and recrystallized by adding 36ml of acetone and 0.5g of activated carbon to obtain 5.4g of methyl 2-hydroxy-3-methoxybenzoate as a white powder with a content of 93.5%.

[0023] Preparation of 2-hydroxy-3-methoxy-5-allylbenzoic acid methyl ester (5): under nitrogen protection, add 2-hydroxy-3-methoxybenzoic acid methyl ester ( 3) 10.0g, 7.2g of anhydrous potassium carbonate, add 100ml of acetone as a so...

Embodiment example 2

[0026] Preparation of methyl 2-hydroxy-3-methoxybenzoate (3): 7.6g of 2-hydroxy-3-methoxybenzaldehyde (2) and 1g of vanadium pentoxide were placed in a dry container with a reflux device In a three-neck round bottom flask, add 100ml of methanol, then add 50ml of 30% hydrogen peroxide, and stir at room temperature for 8 hours. After the reaction, filter and distill the filtrate to recover methanol, add 50ml of dichloromethane to wash twice, combine the dichloromethane phase, concentrate the solvent to dryness, and obtain 8.2g of dark paste solid. The crude product was heated and recrystallized by adding 36ml of acetone and 0.5g of activated carbon to obtain 5.8g of white powder methyl 2-hydroxy-3-methoxybenzoate with a content of 94.7%.

[0027] Preparation of 2-hydroxy-3-methoxy-5-allylbenzoic acid methyl ester (5): under nitrogen protection, add 2-hydroxy-3-methoxybenzoic acid methyl ester ( 3) 10.0g, 4.2g of sodium hydroxide, add 100ml of acetone as a solvent, raise the tem...

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Abstract

The invention belongs to the field of drug synthesis, and provides an alibendol preparation method, which comprises: selecting 2-hydroxy-3-methoxybenzaldehyde as a raw material, selecting an efficientoxidative esterification catalyst, carrying out one-step oxidative esterification to obtain methyl 2-hydroxy-3-methoxybenzoate, carrying out a reaction on the methyl 2-hydroxy-3-methoxybenzoate and allyl bromide under the action of an alkali to generate methyl 2-allyloxy-3-methoxybenzoate, carrying out a para Claisen rearrangement reaction on the methyl 2-allyloxy-3-methoxybenzoate at a high temperature to obtain methyl 2-hydroxy-3-methoxy-5-allylbenzoate, and carrying out an aminolysis reaction in ethanolamine to generate alibendol. Compared with the traditional synthetic process, the new process of the present invention has characteristics of simple synthesis steps, convenient post-treatment and good product quality, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, and in particular relates to a preparation method of choleretic drug alibendol. Background technique [0002] Alibendol, whose chemical name is 2-hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-(2-propenyl)benzamide, is an excellent antispasmodic choleretic drug. Pharmacological studies have proved that it has low toxicity, obvious choleretic effect, and can promote the normal production and secretion of bile. It is clinically suitable for gallbladder and biliary dysfunction, and has obvious curative effects on chronic cholecystitis, gallstones, weak stomach, rubella, pruritus, migraine, indigestion, constipation and other diseases. [0003] [0004] There are few reports on the synthesis of alibendol. FrancoiClemence's patent mentions a method for preparing alibendol: using ethyl 2-hydroxy-3-methoxybenzoate as a raw material, first reacting with ethanolamine to obtain 2-hydroxy-3-methoxy-N-( 2-hyd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/48C07C231/02C07C67/44C07C67/31C07C67/343C07C69/92
Inventor 鲁执伟王艳姜雨李伟赵鸿伟姜琳
Owner 辽宁博美医药科技有限公司
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