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A kind of refining method and synthetic method of esomeprazole sodium

A technology of esomeprazole sodium and a refining method, which is applied in the field of preparation of esomeprazole salt, can solve problems such as multiple impurities and easy adverse reactions, achieve high purity, avoid adverse reaction events, and have a stable and reliable process control effect

Active Publication Date: 2016-08-24
HEILONGJIANG ZBD PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] There are many kinds of synthetic methods of esomeprazole sodium, but most of them will produce more impurities in the preparation process. The control of process parameters, material proportioning, endpoint monitoring, and selection of refining methods are all key factors affecting product quality. If the purity of the product is low, it is easy to cause adverse reactions

Method used

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  • A kind of refining method and synthetic method of esomeprazole sodium
  • A kind of refining method and synthetic method of esomeprazole sodium
  • A kind of refining method and synthetic method of esomeprazole sodium

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Embodiment 1

[0063] Embodiment 1: the synthesis of omeprazole sulfide

[0064] First add 20L of ethanol (the amount is 8.70 times the volume of the weight of 2-mercapto-5-methoxy-1H-benzimidazole) to the reaction equipment, add 2.12kg (25.2mol) of sodium bicarbonate, after dissolving, add 2- Mercapto-5-methoxy-1H-benzimidazole 2.3kg (12.72mol), add 3,5-dimethyl-2-chloromethyl-4-methoxypyridine hydrochloride 2.8kg (12.56 mol), heat up to reflux reaction (TLC monitoring terminal GF254 plate, developer: ethyl acetate) until the raw material point disappears, adjust the pH value to neutral with acetic acid, filter, and desolventize the filtrate under reduced pressure; add 10L dichloromethane to the residue After dissolving, wash with 2L×2 water (that is, wash twice with 2L of water), dry with anhydrous sodium sulfate, filter, desolvate the filtrate under reduced pressure, add 8L xylene to stir and dissolve the material, add 100g of activated carbon, and stir for about 15min. Filtrate while ho...

Embodiment 2

[0065] Embodiment 2: the synthesis of omeprazole sulfide

[0066] First add 20L of methanol (the amount is 8.70 times the volume of the weight of 2-mercapto-5-methoxy-1H-benzimidazole) to the reaction equipment, add 1kg (25mol) of sodium hydroxide, after dissolving, add 2-mercapto- 2.3kg (12.72mol) of 5-methoxy-1H-benzimidazole, after dissolving, add 2.8kg (12.56mol) of 3,5-dimethyl-2-chloromethyl-4-methoxypyridine hydrochloride , heat up to reflux reaction (TLC monitoring endpoint GF254 plate, developer: ethyl acetate) until the raw material point disappears, adjust the pH value to neutral with acetic acid, filter, and the filtrate is precipitated under reduced pressure; the residue is dissolved in 10L dichloromethane , washed with 2L×2 water, dried with anhydrous sodium sulfate; filtered, the filtrate was desolvated under reduced pressure, added 8L xylene to stir and dissolve the material, then added 100g activated carbon, stirred for about 15min, filtered while hot, and the...

Embodiment 3

[0067] Embodiment 3: the synthesis of omeprazole sulfide

[0068] First add 20L of methanol (the amount is 8.70 times the volume of the weight of 2-mercapto-5-methoxy-1H-benzimidazole) to the reaction equipment, add 2.6kg (30.9mol) of sodium bicarbonate, after dissolving, add 2- Mercapto-5-methoxy-1H-benzimidazole 2.3kg (12.72mol), add 3,5-dimethyl-2-chloromethyl-4-methoxypyridine hydrochloride 2.8kg (12.56 mol), heated to reflux reaction (TLC monitoring GF254 plate, developer: petroleum ether and ethyl acetate, the volume ratio of the two is 1:6) reacted until the raw material point disappeared, adjusted the pH value to neutral with acetic acid, filtered, and the filtrate Desolvation under reduced pressure; add 10L of dichloromethane to dissolve the residue, wash with 2L×2 water, and dry with anhydrous sodium sulfate; filter, desolvate the filtrate under reduced pressure, add 8L of xylene to stir and dissolve the material, add 100g of activated carbon, and stir After about 1...

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Abstract

The invention relates to a refining method and a synthesis method of esomeprazole. The refining method comprises the following steps: firstly, suspending a crude esomeprazole product in 2-5 times of good organic solvents, stirring at low temperature, filtering to remove the impurities, slowly adding 10-20 times of adverse organic solvents, stirring to crystallize over night, and centrifuging to dry, thereby obtaining a refined esomeprazole product. The refining method of the esomeprazole is stable and controllable in process, simple and convenient to operate and easy to industrialize; the prepared esomeprazole is hihg in purity, high in yield, high in optical purity and stable in component, and happening of adverse reaction accidents is greatly avoided.

Description

technical field [0001] The invention relates to a preparation method of esomeprazole salt, in particular to a refining method of esomeprazole sodium and a synthesis method thereof. Background technique [0002] Omeprazole, as the first proton pump inhibitor, has a history of more than ten years in the treatment of acid-related diseases. The drug has two optical isomers, a racemic mixture composed of S-omeprazole and R-omeprazole, of which S-omeprazole is also known as esomeprazole, which has an effect on gastric acid secretion. The inhibitory effect of omeprazole was significantly higher than that of single-dose administration of omeprazole. [0003] Esomeprazole sodium (Esomeprazole sodium), S-omeprazole sodium, is a common esomeprazole salt, molecular formula: C 17 h 18 N 3 NaO 3 S, the appearance is white to light yellow powder, its chemical name is: 5-methoxy-2-((S)-((4-methoxy-3,5-dimethyl-2-pyridyl)methanol base) sulfinyl) -1H-benzimidazole sodium, its chemical s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 方同华周广红董雪婷陈玉玲
Owner HEILONGJIANG ZBD PHARMA
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