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Preparation method of acipimox

A technology of methylpyrazine and dimethylpyrazine, applied in the field of medicine, can solve the problems of harsh reaction conditions, many decarboxylation by-products, unfavorable and the like, and achieve the effect of mild reaction conditions

Inactive Publication Date: 2014-01-15
WEIHAI WEITAI PHARMA TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Compared with route 1, the reaction conditions of route 2 are relatively harsh, especially the large-scale use of concentrated sulfuric acid, which is very unfavorable to both reaction equipment and post-treatment, and there are many decarboxylation by-products under acidic conditions, which is not conducive to the purification of intermediates

Method used

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  • Preparation method of acipimox
  • Preparation method of acipimox
  • Preparation method of acipimox

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of 2,5-dimethylpyrazine-1-oxide

[0024] Add 20g of 2,5-dimethylpyrazine and 20mL of 30% hydrogen peroxide to a 500mL three-strand bottle, heat to 80°C for 10h, cool down to room temperature naturally, extract with dichloromethane (100mL x3), dry over anhydrous sodium sulfate, and filter with suction , The solvent was removed from the filtrate under reduced pressure, and the residue was recrystallized from toluene to obtain 18 g of white solid with a yield of 78%.

Embodiment 2

[0025] Embodiment 2: Preparation of 2-acetoxymethyl-5-methylpyrazine

[0026] Add 20g of 2,5-dimethylpyrazine-1-oxide, 40mL of acetic anhydride, 10g of sodium acetate and 250mL of acetic acid into a 500mL Sanjin bottle, heat to reflux for 5h, and remove the solvent under reduced pressure to obtain a residue of 23g, which is used directly for Next reaction.

Embodiment 3

[0027] Embodiment 3: the preparation of 2-hydroxymethyl-5-methylpyrazine

[0028] The product from the previous step and 50 mL of 1N sodium hydroxide solution were heated to 50°C, stirred for 3 h, extracted with ethyl acetate (100 mL x 3), concentrated under reduced pressure to remove about 2 / 3 of the solvent, and the remaining liquid was directly used for the next reaction.

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Abstract

The invention relates to a preparation method of acipimox for treating hyperlipidemia, belonging to the field of medicines. The invention provides an acipimox synthesis process which is simple and easy to operate. The preparation method comprises steps of with 2, 5-dimethylpyrazine as a raw material, carrying out nitrogen oxidation, reaction with acetic anhydride and alkaline hydrolysis to obtain 2-hydroxymethyl-5-methylpyrazine; directly oxidizing a post-treatment fluid by using 2,2,6,6-tetramethyl-1-piperidinyloxy / sodium hypochlorite / potassium bromide to obtain 5-methylpyrazine-2-carboxylic acid, wherein the post-treatment fluid is not needed to be dried and concentrated; oxidizing 5-methylpyrazine-2-carboxylic acid by using hydrogen peroxide / sodium tungstate to obtain acipimox.

Description

Technical field: [0001] The invention relates to a preparation method of a lipid-lowering drug Acipimox, which belongs to the field of medicine. Background technique: [0002] Acilimus is a broad-spectrum long-acting lipid-lowering drug, used for various primary and secondary hyperlipidemia, can reduce plasma total cholesterol, triglycerides, low-density lipoprotein and very low-density lipoprotein Protein content, increase high-density lipoprotein content, lasting and stable effect. The product was first applied for listing in Italy by Pharmacia in 1985. Then, relying on its high safety and remarkable curative effect, it has been listed in Germany, Chile, Switzerland, Hong Kong, China and other countries and regions. As a niacin derivative, acipimox has the following structural formula: [0003] [0004] In the published literature, a variety of methods for preparing acipimox have been announced, which can be mainly divided into two categories: [0005] One is to use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/24
CPCC07D241/24
Inventor 蔡华军
Owner WEIHAI WEITAI PHARMA TECH DEV
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