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Omeprazole sodium compound and method for synthesizing the same

A technology of omeprazole sodium and a synthetic method, which is applied in the field of medicine, can solve problems such as low yield, poor purity, and long reaction time, and achieve the effects of good product purity, cost reduction, and shortened reaction time

Inactive Publication Date: 2009-07-22
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, many patents have reported the preparation method of omeprazole sodium, most of which adopt omeprazole and sodium hydroxide, sodium alkoxide or sodium acetoacetate to react, and the preparation of omeprazole is through multi-step Reaction preparation, finally the prepared intermediate 2-mercapto-5-methoxy-1H-benzimidazole and 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride in hydrogen The docking is carried out in the organic solvent of sodium oxide, the yield has been between 70-80%, the reaction time is longer, and the sulfide intermediate 5-methoxy-2-[(4-methoxy-3,5- Dimethylpyridin-2-yl)methylthio]-1-benzimidazole is oxidized to product omeprazole with poor purity and low yield

Method used

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  • Omeprazole sodium compound and method for synthesizing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-1H-benzimidazole

[0038] 180 grams (1mol) of 2-mercapto-5-methoxy-1H-benzimidazole and 222 grams (1mol) of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride Add 5 liters of ethanol and acetone mixed solvent (V:V=3:1), comprise the sodium hydroxide of 80 grams (2mol), add 5 grams (0.033mol) sodium iodide simultaneously, this reaction mixture is heated and refluxed 1.5 hours , cooled to room temperature, filtered to remove insoluble matter, the filtrate was distilled off under reduced pressure to remove most of the solvent, the residue was dissolved in 3 liters of ethyl acetate, washed twice with 1 liter of water, the organic phase was dried with anhydrous sodium sulfate, filtered, concentrated , add 400ml of acetone to the residue, freeze the organic phase to 0°C, precipitate a solid overnight, filter to obtain 315.8 grams of off-white solid 5-methoxy-2-[(4-methoxy-3,5-lutidine -2-yl)methy...

Embodiment 2

[0039] The synthesis of embodiment 2 omeprazole

[0040]5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-1H-benzimidazole prepared in Example 1 was added to 1500ml of Ethyl acetate, the reaction system is cooled to -25 ° C, maintain this reaction temperature, slowly add 40ml of peracetic acid, continue to react for 0.5 hours after adding, adjust the pH value of the reaction system with 10% sodium hydroxide at the same time, maintain at When pH=8, a precipitate precipitated out, filtered, washed the filter cake with water, dried, and then recrystallized with methanol to obtain 314.4 g of white solid omeprazole, yield: 94.8%.

Embodiment 3

[0041] The synthesis of embodiment 3 omeprazole sodium

[0042] The omeprazole that embodiment 2 is made joins in the isopropanol of 1000ml, adds dropwise aqueous sodium hydroxide solution (the sodium hydroxide of 37.1 grams is dissolved in the distilled water of 60ml) simultaneously, this mixture is stirred at room temperature 1 hour , then filtered, washed the filter cake with 40ml of isopropanol, and vacuum-dried at 40°C to obtain 344 grams of product, yield: 98.1%. HPLC: 99.8%.

[0043] Elemental analysis theoretical value C: 52.9%, H: 5.2%, N: 10.9%, 0: 16.6%, S: 8.3%; experimental value C: 53.1%, H: 5.3%, N: 11.0%, 0: 16.6% , S: 8.2%.

[0044] 1 H-NMR (DM SO): δ(10 -6 ): 2.09-2.20 (s, 6H, CH 3 ), 3.68-3.81 (s, 6H, OCH 3 ), 4.67-4.78 (m, 2H, CH 2 ), 7.05-7.56 (m, 3H, benzene H), 8.19 (s, 1H, pyridine H), 13.44 (s, 1H, NH).

[0045] MS (m / e): 330 (M + , 100%), 196 (M + ,-C 9 h 12 NO, 15%).

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Abstract

The invention relates to an omeprazole sodium compound and a synthetic method thereof; the synthetic method comprises the steps: in a reaction system, sodium iodide is added as a catalyst and ethanol and acetone are adopted as reactive solvents so that the reaction time is shortened and the product yield is significantly improved simultaneously and exceeds 90 percent; and in the generation step of omeprazole, peracetic acid is taken as a oxidizing agent. The synthetic method reduces costs, improves the oxidizing conditions, reduces side reaction, has relatively high product yield and product purity and obtains significant technical effect.

Description

technical field [0001] The invention relates to a synthesis method of omeprazole sodium compound, which belongs to the technical field of medicine. Background technique [0002] Omeprazole sodium, its chemical name is: 5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)-methyl]-sulfinyl} -1H-Benzimidazole Sodium Monohydrate, Molecular Formula C 17 h 18 N 3 NaO 3 S·H 2 O, molecular weight 385.41, structural formula: [0003] [0004] Omeprazole sodium is a proton pump inhibitor of gastric parietal cells, which can specifically inhibit the H++K+-ATPase on the secretory microtubules formed by the apical membrane of the parietal cells and the tubular vesicles in the cytoplasm, thereby effectively Inhibits gastric acid secretion. [0005] At present, many patents have reported the preparation method of omeprazole sodium, most of which adopt omeprazole and sodium hydroxide, sodium alkoxide or sodium acetoacetate to react, and the preparation of omeprazole is through multi-s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61P1/04
Inventor 邓菊娟
Owner HAINAN LINGKANG PHARMA CO LTD
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