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Preparation method of esomeprazole sodium

A technology of esomeprazole sodium and esomeprazole, which is applied in the field of chemistry and can solve the problems of inapplicability to large-scale production, many reagents, and cumbersome operations

Active Publication Date: 2015-09-23
SHANDONG JINHE DRUG RES DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many evaporation steps in the preparation process of this method, the reagents are too much, and the operation is too cumbersome, so it is not suitable for large-scale production

Method used

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  • Preparation method of esomeprazole sodium
  • Preparation method of esomeprazole sodium

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0036] Experimental example 1, the impact of different solvents on the yield of intermediate I

[0037] 1. Purpose: To investigate the influence of selecting different solvents on the yield of intermediate I omeprazole sodium.

[0038] 2. Method: 4 experiments in parallel, each experiment is as follows

[0039] Put 17.3g of sodium hydroxide into 400ml of solvent A, and stir at room temperature for 2h until all the sodium hydroxide particles are dissolved. Add 100g of omeprazole to the reaction solution, stir at room temperature for 2 to 3 hours, a large amount of white precipitate appears, filter, wash the filter cake with 100ml of ethyl acetate, weigh and calculate the yield after drying, which is intermediate I omeprazole azole sodium.

[0040] Wherein the solvent A is ethanol (adding disodium hydrogen phosphate, test 1-1), methanol (test 1-2), isopropanol (test 1-3), n-butanol (test 1-4).

[0041] 3. Results and conclusions

[0042] The differences between the specific ex...

experiment example 2

[0046] Experimental example 2, the influence of sodium hydroxide consumption on intermediate I yield

[0047] One, purpose: investigate the influence of the consumption of sodium hydroxide on intermediate I omeprazole sodium yield.

[0048] 2. Method: 5 experiments in parallel, each experiment is as follows

[0049] Put different amounts of sodium hydroxide into 400ml of isopropanol, and stir at room temperature for 2 hours until all the sodium hydroxide particles are dissolved. Add 100g of omeprazole to the reaction solution, stir at room temperature for 2 to 3 hours, a large amount of white precipitate appears, filter, wash the filter cake with 100ml of ethyl acetate, weigh and calculate the yield after drying, which is intermediate I omeprazole azole sodium.

[0050] Wherein the feeding amount of sodium hydroxide is respectively 11.6g (1.0eq, experiment 2-1), 14.5g (1.25eq, experiment 2-2), 17.3g (1.5eq, experiment 2-3), 20.2g (1.75eq , Runs 2-4), 11.6 g (23.2 eq, Runs 2...

experiment example 3

[0057] Experimental example 3, the influence of different solvents on product isomers in the preparation process of intermediate II

[0058] 1. Purpose: To investigate the influence of different solvents on the product isomers during the preparation of intermediate II.

[0059] 2. Method: 4 experiments were performed in parallel, and the operation of each experiment was as follows:

[0060] Put 400ml of different solvents (cyclohexane, n-hexanol, n-propanol, ethyl acetate) and 10.5g of purified water into the reaction flask, add 106g of omeprazole sodium under stirring at room temperature, and continue stirring at room temperature for 1 to 2 hours. Filter, and filter the solvent as dry as possible to obtain omeprazole sodium hydrate, and ensure that its water content is within the range of 1.5-2.0%. The omeprazole sodium hydrate that obtains is added in the reaction bottle that fills 1000ml acetone. Control the reaction temperature at 35-40°C, add D-diethyl tartrate, tetrais...

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Abstract

The invention provides a preparation method of esomeprazole sodium. The method provided by the invention is simple to operate, is high in yield and purity of the esomeprazole sodium and is suitable for industrial production. A specific reactive solvent is screened, the addition amount of water is regulated, and the specific reaction temperature, time and pH value are controlled, so that the esomeprazole sodium of which the purity exceeds 99% and the yield exceeds 32% is obtained.

Description

technical field [0001] The invention relates to a preparation method of esomeprazole sodium, which belongs to the technical field of chemistry. Background technique [0002] Esomeprazole is a single isomer of omeprazole, the (S)-isomer. Due to higher bioavailability and more consistent pharmacokinetics, esomeprazole is more effective than other PPIs in suppressing acid. [0003] Esomeprazole sodium, trade name: Nexium, its English name is Esomeprazole Sodium, chemical name: 5-methoxy-2-((S)-((4-methoxy-3, 5-Dimethyl)-2-pyridyl)methyl)sulfinyl-1H-benzimidazole sodium. Molecular formula is C 17 h 18 N 3 o 3 SNa. The structural formula of esomeprazole sodium: [0004] [0005] In the prior art, there are mainly two types of methods for preparing esomeprazole sodium, one is to use a chiral catalyst to asymmetrically oxidize omeprazole sulfide to obtain esomeprazole sodium, such as Chinese patent 20120590638.6, with 2-Chloromethyl-3,5-dimethyl-4-methoxypyridine and 2-...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 常建辉彭坤刘玉芹张栋李晗
Owner SHANDONG JINHE DRUG RES DEV
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