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Method for preparing omeprazole

A drug and anti-ulcer technology, applied in the field of preparation of anti-ulcer drugs, can solve the problems of low purity and low yield of the final product, and achieve the effects of good directional oxidation, simple post-processing and high energy consumption

Active Publication Date: 2010-09-29
ZHEJIANG MENOVO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These disadvantages will lead to low purity and low yield of the final product

Method used

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  • Method for preparing omeprazole
  • Method for preparing omeprazole
  • Method for preparing omeprazole

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0016] 187g potassium monopersulfate mixture (2KHSO 5 -KHSO 4 -K 2 SO 4 , 0.3mol) was dissolved in 650mL of deionized water, and then 0.2mol of 50g of o-iodobenzoic acid was added in one go. The mixture was heated to 70-75°C and then stirred at this temperature for 3h. After the reaction, the suspension was cooled with ice water, stirred slowly at this temperature for 1 h, the mixture was filtered, the solid was washed with water and acetone and dried to obtain 44.2 g of IBX crystals, with a yield of 78.9%. The measured melting point is 232°C (note: it explodes at 232°C).

example 2

[0018] Dissolve 80.0g (0.48mol) of KBrO3 in 750mL of sulfuric acid solution with a concentration of 1mol / L, heat to 60°C, and add 80g (0.32mol) of finely ground o-iodobenzoic acid powder in batches at this temperature, adding each time 10g, added within 40min. At this time, the solution turned orange red, and bromine vapor was produced. After the addition, the temperature was maintained at 65°C for 2.5 hours. Then cooled with ice water, filtered, the filter cake was washed twice with water and acetone respectively, and dried to obtain 82.8 g of IBX product with a yield of 91.6%.

example 3

[0020] 33 g of pyrmetazole (0.1 mol) was dissolved in 250 mL of acetone, and 42 g of IBX (0.15 mol) was added. The mixture was stirred at 30-50°C, and the progress of the reaction was monitored by TLC. After 18 hours of reaction, filter and wash the obtained solid with acetone, combine the washing liquid with the filtrate, remove part of the acetone, and then pour it into water. At this time, a solid precipitates, filter the solid, wash twice with water, dry, and recrystallize with ethanol. Obtain product omeprazole 32.0g, yield 92.6%.

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Abstract

This invention relates to preparation method of a antiulcer drug. The invention takes pyrmetazole that chemical name is 5 - methoxyl group - 2 - { [ ( 4 - methoxyl group - 3, 5 - dimethyl - 2 - pyridyl) methyl] sulfinyl} - 1 hydrogen - benzimidazole as raw material, takes IBX that chemical name is 1 - hydroxy - 1, 2 - benzene iodine acyl - 3 ( 1 hydrogen) - ketone - 1 - oxide as oxidizer, and takes quaternary ammonium salt compound tetraethyl ammonium bromide or tetrabutyl ammonium bromide as catalyzer, to synthesize antiulcer drug omeprazole. The invention also relates to the according reclaim measure of oxidizer.

Description

technical field [0001] The invention relates to a preparation method of an anti-ulcer drug, in particular to a method for synthesizing the anti-ulcer drug omeprazole by using pyrmetazole as a starting material, IBX as an oxidant, and quaternary ammonium compounds as a catalyst. Background technique [0002] Omeprazole, Omeprazole, chemical name 5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}-1 hydrogen - Benzimidazole (structural formula as shown in II), which is the first gastric proton pump inhibitor on the market. It has good chemical stability and has a strong and long-lasting inhibitory effect on gastric acid secretion caused by histamine, pentagastrin, acetylcholine, food and stimulation of the vagus nerve. In the treatment of peptic ulcer, it has the advantages of rapid pain relief, short course of treatment, and high lesion healing rate. It is one of the most effective gastric acid inhibitors discovered so far. Omeprazole is prepared industrially t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
Inventor 宋国强杨毅恒
Owner ZHEJIANG MENOVO PHARMA
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