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(S)-pantoprazole preparation method

A technology for pantoprazole and pantoprazole sulfide, which is applied in the field of drug synthesis, can solve the problems of low enantioselectivity, complicated post-processing, expensive titanium reagents and the like, and achieves good selectivity, simple post-processing, The effect of shortened reaction time

Inactive Publication Date: 2017-05-10
QINGDAO YUNTIAN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] Although selective chemical synthesis has shown advantages over chiral resolution, the above-mentioned synthesis method has problems such as low enantioselectivity, low yield, expensive titanium reagent, and complicated post-treatment; in addition, the above-mentioned method also has There is a situation where pantothioether is over-oxidized to produce a by-product sulfone, and purification is extremely difficult

Method used

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  • (S)-pantoprazole preparation method

Examples

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Effect test

Embodiment 1

[0029] Preparation of (S)-pantoprazole

[0030] Under nitrogen protection, at room temperature, pantoprazole sulfide 36.74g (100mmol) and chiral quaternary ammonium salt 19.78g (quinine benzyl quaternary ammonium salt-bromine, 40mmol) were added in 150ml acetonitrile and stirred for premixing for 30min, then added N-Methyl-N-morpholine oxide 23.43g (200mmol), then heated to 50 ° C, continued to stir the contact reaction for 1.5 hours, the reaction solution was filtered, the filtrate was concentrated, washed with water, then recrystallized from petroleum ether, and dried to obtain (S)- Pantoprazole is 37.7g, the yield is 98.3%, the ee value is 99.63%, and no over-oxidized sulfone by-product is detected.

Embodiment 2

[0032] Preparation of (S)-pantoprazole

[0033] Under nitrogen protection, at room temperature, pantoprazole sulfide 36.74g (100mmol) and chiral quaternary ammonium salt 9.89g (quinine benzyl quaternary ammonium salt-bromine, 20mmol) were added in 180ml acetonitrile and stirred and premixed for 30min, then added N-methyl-N-morpholine oxide 17.57g (150mmol), then heated up to 45°C, continued stirring and contact reaction for 1 hour, filtered the reaction solution, concentrated the filtrate, washed with water, then recrystallized petroleum ether, and dried to obtain (S)- Pantoprazole is 37.8g, the yield is 98.7%, the ee value is 99.51%, and no over-oxidized sulfone by-product is detected.

Embodiment 3

[0035] Preparation of (S)-pantoprazole

[0036] Under nitrogen protection, at room temperature, pantoprazole sulfide 36.74g (100mmol) and chiral quaternary ammonium salt 24.72g (quinine benzyl quaternary ammonium salt-bromine, 50mmol) were added in 180ml acetonitrile and stirred for pre-mixing for 30min, then added N-methyl-N-morpholine oxide 17.57g (150mmol), then heated up to 40°C, continued stirring and contact reaction for 1.5 hours, filtered the reaction solution, concentrated the filtrate, washed with water, then recrystallized petroleum ether, and dried to obtain (S)- Pantoprazole 37.5g, the yield is 97.7%, the ee value is 99.39%, no excessive oxidation of sulfone by-products is detected.

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Abstract

The invention discloses a (S)-pantoprazole preparation method. The preparation method includes: in an organic solvent, subjecting pantoprazole thioether as shown in a formula I to contact reaction with N-methyl-N-morpholine oxide in existence of chiral quaternary ammonium salt to obtain (S)-pantoprazole. By adoption of the (S)-pantoprazole preparation method, wild conditions, high product yield and high selectivity are realized, generation of excessive oxidation products is avoided, and accordingly aftertreatment is simpler. In addition, the (S)-pantoprazole preparation method is high in conditional response efficiency, and reaction time is greatly shortened.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of (S)-pantoprazole. Background technique [0002] Pantoprazole, the chemical name is 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl-1H-benzimidazole, which is in Austria Meprazole is based on the principle of Me too drug design, and the drug with better efficacy is found after modifying the parent structure. It is mainly used to treat duodenal and gastric ulcers and relieve moderate to severe reflux esophagitis. . Compared with other proton pump inhibitors, it is stable under weak acid conditions, and it is quickly activated under strong acid conditions and has little interaction with other drugs. Compared with omeprazole, it is 7 times higher, and its safety and effectiveness are higher than that of omeprazole and lansoprazole when it is used with other drugs. Stablize. [0003] Pantoprazole was developed by German company Byk Gu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12C07B2200/07
Inventor 许士娜
Owner QINGDAO YUNTIAN BIOTECH
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