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Preparation method of optically pure Lansoprazole

A technology for lansoprazole and enantiomer, which is applied in the field of preparation of optically pure lansoprazole, can solve the problems of long reaction time and the like, and achieves the effects of mild conditions, simple method and high optical purity

Active Publication Date: 2014-06-25
SICHUAN HAISCO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] WO2009114981A1 and CN101538264A describe the use of complexes formed by chiral tartaric acid amide compounds and tetraisopropyl titanium oxide to oxidize lanzo sulfide to obtain lansoprazole with medium enantioselectivity and medium yield, which The reaction time of this method is also longer

Method used

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  • Preparation method of optically pure Lansoprazole
  • Preparation method of optically pure Lansoprazole
  • Preparation method of optically pure Lansoprazole

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Embodiment

[0061] The present invention will be further described in detail below through specific examples. However, it should not be understood that the scope of the above subject matter of the present invention is limited to the following embodiments, and all technologies realized based on the above contents of the present invention belong to the scope of the present invention.

Embodiment 1

[0067] With 0.353 grams of 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfanyl]-1H-benzimidazole and 0.197 grams N,N'-dibenzyl-(R,R)-tartaric acid diamide was heated to 70°C in 2 ml of toluene, and stirred for 15 minutes. Then it was lowered to 60°C, and 0.09 ml of tetraisopropoxytitanium was added under heat preservation, and after heat preservation and stirring for 1 hour, 1.8 mg of water was added, and heat preservation and stirring for 1 hour. The temperature was lowered to 30°C, and 0.18 ml of phenylisopropyl hydroperoxide was added dropwise. After reacting at 30°C for 2 hours, the enantiomeric excess value of (R)-lansoprazole determined by HPLC was 91.7%, and the content was 73.8%.

Embodiment 2

[0069] With 0.353 grams of 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfanyl]-1H-benzimidazole and 0.197 grams N,N'-dibenzyl-(R,R)-tartaric acid diamide was heated to 70°C in 2 ml of 1,4-dioxane, and stirred for 15 minutes. Then it was lowered to 60°C, and 0.09 ml of tetraisopropoxytitanium was added under heat preservation, and after heat preservation and stirring for 1 hour, 1.8 mg of water was added, and heat preservation and stirring for 1 hour. The temperature was lowered to 30°C, and 0.18 ml of phenylisopropyl hydroperoxide was added dropwise. After reacting at 30°C for 2 hours, the enantiomeric excess value of (R)-lansoprazole determined by HPLC was 43.7%, and the content was 23.5%.

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Abstract

The invention provides a preparation method of optically pure 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (Lansoprazole). The method required to be protected in the invention comprises the following steps: directly asymmetrically oxidizing 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfeny]-1H-benzimidazole in the presence of a complex catalyst under the action of an organic alkali or inorganic alkali additive or without the organic alkali or inorganic alkali additive to form corresponding Lansoprazole rich in single enantiomers, wherein the complex catalyst is formed through a reaction of (R,R) or (S,S)-N,N'-tartric acid dibenzyl amide ligand, alkoxytitanium and water at a certain temperature; and sequentially carrying out alcohol-water and ketone-water recrystallization to obtain the optically pure Lansoprazole.

Description

technical field [0001] The invention relates to a preparation method of optically pure lansoprazole with anti-peptic ulcer activity. Background technique [0002] Lansoprazole racemate has excellent anti-ulcer activity, and the toxic and side effects of optically active lansoprazole are far less than racemate, wherein with dexlansoprazole (formula IV) curative effect is better, therefore, dextro-lansoprazole The application research of lansoprazole is of great significance. [0003] [0004] WO9602535 discloses a method for obtaining lansoprazole with medium enantioselectivity and medium yield by oxidizing lanzosulfide under the action of chiral titanium complex and base. [0005] CN1426406A discloses a method for preparing lansoprazole with high enantioselectivity. In this method, optically pure diethyl tartrate, lanzo sulfide, water and toluene are mixed and heated to 50-55 ° C. After stirring for 30 minutes, Add tetraisopropyltitanium oxide under the protection of in...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 邓金根车国勇黄晴菲朱槿唐磊万华王启卫袁辛娅汪东海
Owner SICHUAN HAISCO PHARMA CO LTD
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