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Method for preparing dexlansoprazole

A technology for dexlansoprazole and a compound, which is applied in the field of preparing dexlansoprazole, can solve the problems of high cost, toxicity of active components, prolonging the technological process, etc., and achieves improved yield, good stability, and simplified technological process. Effect

Inactive Publication Date: 2011-06-29
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (1) In the process of asymmetric oxidation, impurities such as N-oxides and sulfone-type analogs will be produced. These impurities are difficult to remove by conventional purification methods such as recrystallization. Therefore, this method needs to be removed by chromatography. However, the removal of impurities Method cost is too high
[0011] (2) In order to precisely control the oxidation in the asymmetric oxidation process, it is necessary to use transition metals such as vanadium as a catalyst to suppress the generation of impurities, but this can only hinder the generation of N-oxides, and cannot reduce the sulfone type in the product. The content of impurities such as analogues, and these transition metals can bring toxicity to active components
However, this method increases operational steps such as crystallization, prolongs the process flow, and reduces the yield, which is not conducive to industrial production.

Method used

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  • Method for preparing dexlansoprazole
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  • Method for preparing dexlansoprazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Synthesis of R-2-[[(4-chloro-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole

[0026]

[0027] Raw material 2-[[(4-chloro-3-methyl-2-pyridyl)methyl]sulfanyl]benzimidazole (645.1g), toluene (3600ml) and L-(+) diethyl tartrate ( 168ml) were mixed, heated to 50-60°C for 0.5h, added titanium tetraisopropoxide (131ml), and continued to react at this temperature for 1h. The reaction solution was cooled to 20°C, diisopropylethylamine (135ml) was added, the temperature was lowered to -10°C, the temperature was controlled from -10°C to 0°C, and 80% cumene hydroperoxide (1203ml) was added to control the temperature at -5°C. ℃ to 0 ℃ reaction 4h. Thin-layer chromatography analysis basically completed the reaction, added 30% sodium thiosulfate solution (1600ml), stirred for 10min, and added dropwise n-hexane (1550ml), tert-butyl methyl ether (1550ml), n-hexane (13000ml) in sequence from 0°C to 10°C ), a white solid precipitated, filtered, and washed once with tert-b...

Embodiment 2

[0030] The synthesis of embodiment two dexlansoprazole

[0031]

[0032] Add the intermediate R-2-[[(4-chloro-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole (322.2g) and dimethyl Sulfoxide (2100ml), trifluoroethanol (727.8g) and sodium hydroxide (235.6g) were heated up to 60-70°C and reacted for about 4 hours, and the reaction was basically completed by TLC analysis. Cool the reaction solution to room temperature, add water (20 L) dropwise, adjust the pH to about 7 with 330 ml of glacial acetic acid, precipitate a solid, stir for 5 min, and filter to obtain an off-white solid. This solid was dissolved in ethyl acetate (5 L), dried over anhydrous magnesium sulfate (1000.0 g). After filtration, the filtrate was concentrated under reduced pressure to obtain a brown oil. The oil was chromatographed on a short column of silica gel, the eluent was ethyl acetate-n-hexane-methanol (10:10:1), the qualified components were collected, concentrated, and dried with n-hexane (2 L) to...

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Abstract

The invention relates to a method for preparing dexlansoprazole. The method is as follows: the compound in the formula (I) is substituted by trifluoroethanol under an alkaline condition to prepare dexlansoprazole.

Description

technical field [0001] The invention relates to a method for preparing dexlansoprazole, in particular to a method for preparing dexlansoprazole by substituting trifluoroethanol. Background technique [0002] Dexlansoprazole is a new gastroesophageal reflux disease drug superior to lansoprazole, and its structural formula is shown in the figure below. [0003] [0004] FDA approves Takeda Pharmaceutical North America's dexlansoprazole controlled-release capsules (dexlansoprazole, Kapidex) for the treatment of heartburn caused by non-erosive gastroesophageal reflux (GERD), erosive esophagitis (EE) and EE maintenance treatment was administered once a day. This product is the first dual-release controlled-release (DDR) proton pump inhibitor on the market. The preparation specification is 30 or 60mg per capsule. [0005] Proton pump inhibitors reduce gastric acid production by inhibiting H' / K'-ATP. This product contains 2 types of enteric-coated granules, and there are 2 u...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61P1/04
Inventor 杨宝海潘必高徐世伟
Owner JIANGSU HANSOH PHARMA CO LTD
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