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Preparation method of lansoprazole

A technology for lansoprazole and lansoprazole crude products, which is applied in the field of medicine, can solve the problems of high production cost and low yield of lansoprazole, and achieves improved total yield, low solvent toxicity and mild reaction conditions. Effect

Pending Publication Date: 2022-03-11
CISEN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Therefore, the technical problem to be solved in the present invention is to overcome the high production cost and low yield defect of lansoprazole in the prior art, thereby providing a kind of preparation method of lansoprazole, by simple, safe preparation method, preparation Lansoprazole with high yield and high purity is obtained

Method used

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  • Preparation method of lansoprazole

Examples

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Embodiment 1

[0033] The synthetic method of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridine]methylthio-1H-benzimidazole with structural formula (III): to 1000mL Add 400mL of ethanol to the reaction flask, then add 22.4g (100mmol) of 3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanthiol and sodium hydroxide 0.6 g (15mmol), stirred at 40°C, added dropwise a mixed solution of 16.7g 2-chlorobenzimidazole (110mmol) and ethanol (100ml) through a constant-pressure low-liquid funnel, added Bikong and reacted at 40°C for 6h, monitored by HPLC, and the reaction After completion, 0.1 mol / L hydrochloric acid was added dropwise to the reaction bottle, the temperature was controlled at 20°C during the process, the pH was adjusted to 7, and the crystallization was stirred at 20°C for 6h. Suction filter the above system through a Buchner funnel to obtain a filter cake, rinse the solid with 44.8 g of purified water to obtain a wet product. Drying: Blast drying at 55°C for 8 hours to obtain 30.7 g (8...

Embodiment 2

[0038]The synthetic method of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridine]methylthio-1H-benzimidazole with structural formula (III): to 1000mL Add 400mL of ethanol to the reaction flask, then add 22.4g (100mmol) of 3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanthiol and potassium hydroxide 0.8 g (14mmol), stirred at 30°C, added dropwise a mixed solution of 19.8g 2-chlorobenzimidazole (130mmol) and ethanol (100ml) through a constant-pressure low-liquid funnel, added to complete the reaction at 30°C for 3h, monitored by HPLC, and the reaction After completion, 0.1 mol / L hydrochloric acid was added dropwise to the reaction bottle, the temperature was controlled at 10°C during the process, the pH was adjusted to 6, and the temperature was controlled at 10°C to stir and crystallize for 3h after the addition. Suction filter the above system through a Buchner funnel to obtain a filter cake, rinse the solid with 67.2 g of purified water to obtain a wet product. Drying: co...

Embodiment 3

[0043] The synthetic method of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridine]methylthio-1H-benzimidazole with structural formula (III): to 1000mL Add 400mL of ethanol to the reaction flask, then add 22.4g (100mmol) of 3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanthiol and 0.8 g (20mmol), stirred at 35°C, added dropwise a mixed solution of 22.8g 2-chlorobenzimidazole (150mmol) and ethanol (100ml) through a constant pressure low liquid funnel, reacted at 35°C for 5h, monitored by HPLC, and the reaction was complete Add 0.1mol / L hydrochloric acid dropwise to the reaction flask, control the temperature at 15°C during the process, adjust the pH to 6, and stir and crystallize at 15°C for 5h. Suction filter the above system through a Buchner funnel to obtain a filter cake, rinse the solid with 67.2 g of purified water to obtain a wet product. Drying: controlled temperature at 50°C and blown air for 8 hours to obtain 30.4 g (86 mmol) of the product formula III with a yield...

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Abstract

The invention discloses a preparation method of lansoprazole, and belongs to the technical field of medicines, and the preparation method comprises the following steps: reacting 2-chlorobenzimidazole with 3-methyl-4-(2, 2, 2-trifluoroethoxy) to obtain 2-[3-methyl-4-(2, 2, 2-trifluoroethoxy)-2-pyridine] methylthio-1H-benzimidazole, and carrying out a reaction on the 2-[3-methyl-4-(2, 2, 2-trifluoroethoxy)-2-pyridine] methylthio-1H-benzimidazole to obtain 2-[3-methyl-4-(2, 2, 2-trifluoroethoxy)-2-pyridine] methylthio-1H-benzimidazole; then, under the alkaline condition and in the presence of an oxidizing agent and a phase transfer catalyst, oxidizing to generate a lansoprazole crude product; and decolorizing and refining to obtain the lansoprazole. The lansoprazole with high yield and high purity is prepared through the simple and safe preparation method, and the lansoprazole preparation method can be suitable for industrial mass production.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a preparation method of lansoprazole. Background technique [0002] Lansoprazole (Lansoprazole), is a new generation of proton pump inhibitors after omeprazole, the chemical name is 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy )-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole, CAS number: 103577-45-3, molecular formula: C16H14F3N3O2S, molecular weight: 369.36, structural formula as follows: [0003] [0004] Chinese patent CN102617555A discloses a preparation method of lansoprazole, using 2-chloromethyl-3-methyl-4-trifluoroethoxypyridine hydrochloride and 2-mercapto-benzimidazole as starting materials , react in sodium carbonate methanol solution to obtain intermediate 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridine]methylthio-1H-benzimidazole, The combination of cumyl hydroperoxide-tetraisopropyl titanate is used to oxidize to obtain lansoprazole. This preparation method is the sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 李续宋玉琴
Owner CISEN PHARMA
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