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Method for synthesizing lansoprazole and salt thereof

A synthetic method, the technology of lansoprazole, applied in the field of medicinal chemistry, can solve the problems of expensive vanadium catalyst, poor product purity, unsatisfactory effect, etc., and achieve the goals of reducing side reactions, increasing product yield, and shortening reaction time Effect

Inactive Publication Date: 2009-07-08
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The vanadium catalyst used in this method is expensive, and the effect is not ideal, and the yield is low. The urea adduct of hydrogen peroxide is used as an oxidant, and the selectivity in the oxidation step is low, and the product obtained has poor purity and contains a large amount of impurities. , it is difficult to purify

Method used

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  • Method for synthesizing lansoprazole and salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Synthesis of 2-[[[3-methyl-4-(2,2,2 trifluoroethoxy)-2-pyridine]-methyl]sulfanyl]-1H-benzimidazole

[0040] Dissolve 276g (1mol) of 2-chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride in 5L of acetone while adding 5g (0.033mol) of iodine Sodium chloride, then add 180g (1.2mol) 2-mercapto-5-methoxyl group-1H-benzimidazole and 80g (2mol) sodium hydroxide, this reaction mixture is heated to reflux 1.5 hours, is cooled to room temperature, separates out solid, Filter, wash with water, and dry under vacuum at 40 °C to give 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridine]-methyl]sulfanyl]-1H - Benzimidazole 335g, yield: 95%, mp: 150-152°C.

[0041] Elemental analysis C: 54.3%, H: 4%, O: 4.6%, F: 16.2%, N: 11.9%, S: 9.0% (theoretical value C: 54.4%, H: 4%, O: 4.5%, F : 16.1%, N: 11.9%, S: 9.1%)

Embodiment 2

[0042] The synthesis of embodiment 2 Lansoprazole

[0043] Dissolve 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridine]-methyl]sulfanyl]-1H-benzimidazole 212g (0.6mol) in In 4000ml of ethyl acetate, cool with an ice-salt bath to control the internal temperature of the system at 0°C, add dropwise a mixed solution of 120g (0.7mol) of m-chloroperoxybenzoic acid and 1500ml of ethyl acetate, and control the rate of addition to ensure that the reaction temperature is at Between 0-2°C, continue to react at 2°C for 2 hours after the dropwise addition, then wash with 1500ml of saturated sodium carbonate solution, and then wash twice with 2000ml of water, dry the organic phase with anhydrous sodium sulfate, filter, and depressurize Ethyl acetate was distilled, then recrystallized with ethanol 2500ml, activated carbon decolorized, filtered, and vacuum-dried at 40-50°C to obtain 177g of white solid lansoprazole, yield 80%, purity (HPLC) 99.9%, mp: 170- 171°C.

[0044] Elemental analysis...

Embodiment 3

[0045] The synthesis of embodiment 3 lansoprazole sodium

[0046] Add 128g of lansoprazole to 500ml of isopropanol, add 140ml of 10% aqueous sodium hydroxide solution, stir at room temperature for 30 minutes, it becomes a clear liquid, filter, remove insoluble matter, cool the reaction system to 10°C, and precipitate a solid , filtered, and vacuum-dried at 40° C. to obtain 126 g of lansoprazole sodium, with a yield of 93% and a purity of 99.9%.

[0047] Elemental analysis C: 49.1%, H: 3.3%, O: 8.2%, F: 14.5%, N: 10.8%, S: 8.3%, Na: 5.8% (theoretical value C: 49%, H: 3.4%, O : 8.2%, F: 14.6%, N: 10.7%, S: 8.2%, Na: 5.9%)

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Abstract

The invention relates to a method for synthesizing lansoprazole and salts of the lansoprazole, in particular to a method for synthesizing lansoprazole sodium. The method adds sodium iodide serving as a catalyst into a reaction system, uses acetone as a reaction solvent, reduces reaction time, greatly improves product yield to 95 percent. And due to the use of m-choroperoxybenzoic acid as an oxidizer during the production process of lansoprazole, the method reduces cost, improves oxidization conditions, reduces side reactions, achieves higher product yield and purity and obvious invention technical effects.

Description

technical field [0001] The present invention relates to a kind of synthetic method of lansoprazole or its salt, particularly relate to a kind of synthetic method of lansoprazole sodium. It belongs to the technical field of medicinal chemistry. Background technique [0002] Lansoprazole sodium, its chemical name is: 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]-sulfinyl] -1H-benzimidazole sodium salt, structural formula: [0003] [0004] It is a new type of drug that inhibits gastric acid secretion, it acts on the H of gastric parietal cells + -K + -ATPase, which makes parietal cell H + It cannot be transported to the stomach, so that the amount of gastric acid in the gastric juice is greatly reduced. It is clinically used for duodenal ulcer, gastric ulcer, reflux esophagitis, Zollinger-Ellison syndrome (gastrinoma) ) treatment, the curative effect is remarkable, and it has inhibitory effect on Helicobacter pylori. [0005] Two intermediates 2-halomethyl...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61P1/04
Inventor 邱民
Owner HAINAN LINGKANG PHARMA CO LTD
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