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Dexlansoprazole and its preparation method and use

A technology of dexlansoprazole and lansoprazole essence, which is applied in the field of drug synthesis, can solve the problems of low optical purity, low overall yield, and high content of L-isomers, and achieve good results and high purity

Inactive Publication Date: 2017-07-14
乐普药业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is a chiral center in the dexlansoprazole molecule, and a small amount of left-handed isomer cannot be avoided in the production process, which will directly affect the effect of dexlansoprazole as a medicinal ingredient
In the related art, the preparation method of dexlansoprazole has complicated process and low overall yield. The bigger defect is that the final product has a high content of L-isomer and low optical purity, which directly affects the medicinal value of the product.

Method used

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  • Dexlansoprazole and its preparation method and use
  • Dexlansoprazole and its preparation method and use
  • Dexlansoprazole and its preparation method and use

Examples

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preparation example Construction

[0086] The present invention provides a method for preparing dexlansoprazole. The lansoprazole sulfide prepared by lansochloride hydrochloride and 2-mercaptobenzimidazole is asymmetrically oxidized to obtain dexlansoprazole The crude product is refined by optical purity to obtain a refined product of dexlansoprazole, and further purified to obtain dexlansoprazole.

[0087] The preparation method of the dexlansoprazole of the present invention synthesizes crude dexlansoprazole through a simple process, and can obtain a high-purity dexlansoprazole product with an optical purity of nearly 100% through further optical purity refining and purification.

[0088] In a preferred embodiment of the present invention, the reaction route for the preparation of the lansoprazole sulfide is as follows:

[0089]

[0090] Including the addition of 2-mercaptobenzimidazole and lanso chloride hydrochloride in a solvent with alkali, and the reaction of 2-mercaptobenzimidazole and lanso chloride hydrochlo...

Embodiment 1

[0178] A preparation method of dexlansoprazole includes the following steps:

[0179] Step 1: Preparation of Lansoprazole Sulfide:

[0180]

[0181] Add 16675 mL of methanol to a 50L glass reactor, and turn on a stirring ice bath to cool down. Slowly add 1256 g of sodium hydroxide and stir to dissolve completely. The temperature is controlled below 35℃. Add 1256 g of 2-mercaptobenzimidazole and 2300 g of lanso chloride hydrochloride sequentially, and heat to reflux. At 60-70°C, start the heat preservation reaction for 2 hours. HPLC detects the completion of the reaction and starts to cool down. When the temperature is lower than 30°C, filtration starts. After the filtration is completed, the filtrate starts to be distilled under reduced pressure (50-60°C). When the vaporized methanol is 1 / 2 of the feed volume, the temperature is reduced to 25-30°C. 34500mL of water was added, a white solid precipitated, and the mixture was stirred for 30 minutes. Shake filtered water and ri...

Embodiment 2

[0190] A preparation method of dexlansoprazole adopts the same method as in Example 1, except that:

[0191] In the first step:

[0192] The mass ratio of the lanso chloride hydrochloride and 2-mercaptobenzimidazole is 1:0.5;

[0193] After the reaction, the temperature is lowered to 20°C and filtered;

[0194] After vacuum distillation, the temperature is reduced to 20°C, and then water is added to precipitate the product;

[0195] The temperature of the vacuum drying is 60°C;

[0196] The vacuum drying time is 6h.

[0197] In the first step, the yield is about 127%, the content is about 79.4%, and the loss on drying (%) is less than or equal to 0.5%.

[0198] In the second step:

[0199] The volume ratio of toluene and water is 1:1;

[0200] The dosage ratio of the lanso sulfide to the chiral ligand is preferably 1g:1mL;

[0201] The temperature of the heating and heat preservation is 50°C;

[0202] The heating and heat preservation time is 10 minutes;

[0203] The dosage ratio of the lanso s...

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Abstract

The invention provides a dexlansoprazole and its preparation method and use. The preparation method of dexlansoprazole comprises synthesizing a dexlansoprazole crude product through a simple process and carrying out further optical purity refinement and purification to obtain a dexlansoprazole product having optical purity close to 100%. The dexlansoprazole product has optical purity close to 100%, has high purity, can be used as a medicinal component and has a better effect.

Description

Technical field [0001] The present invention relates to the technical field of drug synthesis, in particular to a dexlansoprazole and a preparation method and application thereof. Background technique [0002] Dexlansoprazole is a proton pump inhibitor. Proton pump inhibitors are benzimidazole derivatives that act specifically and non-competitively on H + / K + -ATPase, treat peptic ulcer. Proton pump inhibitors are mostly fat-soluble and weakly alkaline. After being absorbed into the blood, they enter the acidic environment in the parietal cell secretory tubules and tubule cavities. The activation products are generally active sulfenic acid and sulfenamide, and H + -K + -ATPase sulfhydryl coupling forms an irreversible covalent disulfide bond, blocking H + -K + Transport mechanism, thereby inhibiting gastric acid secretion. [0003] There is a chiral center in the dexlansoprazole molecule, and a small amount of levorotatory isomer cannot be avoided during the production process. T...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07B53/00
CPCC07D401/12C07B53/00C07B2200/07
Inventor 于力强胡春振卢志宏胡媛媛孟祥安
Owner 乐普药业科技有限公司
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