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New preparation method of S-pantoprazole sodium

A technology of pantoprazole sodium and sodium bismuthate, which is applied in the field of medicine, can solve the problems of unfavorable industrial production, low chiral selectivity, and low utilization rate of raw materials, and achieve the advantages of convenient industrial production, high yield, and simple operation Effect

Inactive Publication Date: 2014-04-02
NANJING ZENKOM PHARMA
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Problems solved by technology

[0006] The Chinese patents whose application numbers are 200810110447.9 and 200810150111.5 adopt the method of chiral resolution to prepare S-pantoprazole sodium. The utilization rate of raw materials prepared by this method is low and the cost is high, which is not conducive to industrial production
The Chinese patents with application numbers 200380104409.8, 201110340811.2 and 200710010273.4 propose the use of asymmetric oxidation to prepare S-pantoprazole sodium, but the chiral selectivity is low, the yield is low, and it is not conducive to industrial production

Method used

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  • New preparation method of S-pantoprazole sodium

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Embodiment 1

[0021] 1) Add 2 kg of 5-difluoromethoxy-2-mercapto-1H-benzimidazole into 20L aqueous solution of 900 g NaOH in a 50L reactor. Control the temperature at 20-25°C, add dropwise 7 L of aqueous solution of 2 kg 2-chloromethyl-3,4-dimethoxypyridine hydrochloride, control the temperature at 30°C, and keep stirring for 4 hours. Add 10 L of dichloromethane to the reaction kettle for extraction, separate the layers, extract the aqueous layer once with 10 L of dichloromethane, combine the organic phases, and wash with 10 L×2 water. The dichloromethane layer was dried by adding anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain 3.21 kg of light yellow solid powder Compound II, with a yield of 94.41% and an HPLC purity of 99.24%.

[0022] 2) Add 20 L of toluene, 2.5 kg of compound II, 1.7 kg of N,N'-bis(3-pyridylmethyl)-D(-)-tartrate diamide, 1.0 kg of isopropyl titanate into a 50 L reactor , 850 mL of triethylamine, stirring the system to raise the temp...

Embodiment 2

[0025] 1) Add 1.89 kg 5-difluoromethoxy-2-mercapto-1H-benzimidazole to 20L aqueous solution of 875 g NaOH in a 50L reactor; control the temperature at 20-25 ℃, add dropwise 1.9 kg 2-chloroform Base-3,4-dimethoxypyridine hydrochloride 7 L aqueous solution, control the temperature at 40 ° C, keep stirring and react for 4 hours; add 10 L dichloromethane to the reaction kettle for extraction, separate the layers, and use 10 L Extract once with dichloromethane, combine the organic phases, and wash with 10 L × 2 water. The dichloromethane layer was dried by adding anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain 2.8 kg of light yellow solid powder Compound II, with a yield of 90.32% and a HPLC purity of 99.30%.

[0026] 2) Add 20 L of toluene, 2.5 kg of compound II, 1.7 kg of N,N'-bis(3-pyridylmethyl)-D(-)-tartrate diamide, 1.0 kg of isopropyl titanate into a 50 L reactor , 850 mL of triethylamine, and the system was stirred and heated to 60°C. ...

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Abstract

The invention discloses a new preparation method of S-pantoprazole sodium. The method comprises the following steps: 1) performing condensation of 5-difluoro methoxy-2-mercapto-1H-benzimidazole and 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride in the presence of sodium hydroxide to obtain II; 2) performing catalytic oxidation of II with sodium bismuthate as an oxidizing agent and chiral bipyridine methyl amide as a chiral ligand, and in the presence of alkoxy titanium to obtain S-pantoprazole III; 3) performing salification of III and sodium hydroxide to obtain S-pantoprazole sodium I. The method is simple in operation, mild in reaction, and high in yield; the obtained product is high in chemical purity and optical purity, and is convenient for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to a new preparation method of S-pantoprazole sodium. Background technique [0002] Current status of peptic ulcer treatment: Peptic ulcer is a common and frequently-occurring disease, and about 5% to 6% of people in the world have suffered from this disease. Although the drugs for the treatment of peptic ulcer have developed rapidly in recent years, the oldest antacids still have a corresponding status in the treatment of peptic ulcers. Antacids are mainly some inorganic weak bases. Commonly used drugs include sodium bicarbonate, hydrogen Magnesium oxide, magnesium trisilicate, etc., can directly neutralize gastric acid after oral administration, and can reduce or relieve the stimulation and corrosion effect of gastric acid on the ulcer surface; the appearance of H2 receptor antagonists such as cimetidine in the 1970s made peptic ulcer The incidence of complications decreased signif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 杨鑫祁艳徐卓业
Owner NANJING ZENKOM PHARMA
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