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Synthesis method of R-lansoprazole

A technology of dexlansoprazole and dexlansoprazole sodium is applied in the field of drug synthesis, which can solve the problems of many types of raw materials, cumbersome operations, and low prices, and achieve convenient post-processing, high conversion rate of raw materials, The effect of easy operation

Inactive Publication Date: 2016-12-07
成都尚药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And the solubility of lansoprazole sulfide in above-mentioned several solvents is less
[0017] More than the method for synthesizing R-lansoprazole, oxidation step is all very simple, but because m-chloroperoxybenzoic acid price is expensive, and content is indeterminate, should not adopt; Synthetic racemic lansoprazole needs to use special and high price The resolving agent is used for resolution, so it is not used; tetraisopropyl titanate is used as a catalyst, L-diethyl tartrate or N,N'-dipropyl-L-tartrate diamide is used as a chiral auxiliary agent, peroxidized Hydroxycumene is an oxidizing agent, the price is low, and the raw materials are easy to get, but there are many types of raw materials and cumbersome operations

Method used

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  • Synthesis method of R-lansoprazole
  • Synthesis method of R-lansoprazole
  • Synthesis method of R-lansoprazole

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Step 1: Preparation of lansoprazole sulfide.

[0054] Material ratio

[0055] Step 1 material ratio table

[0056]

[0057] Operation process:

[0058] ①.In a 100L enamel reaction kettle, add 30kg of anhydrous methanol, then add 5kg of 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride, 2 -Mercaptobenzimidazole 3kg, stirred for 30min.

[0059] ②. Slowly add 2.54kg of sodium hydroxide in 5 times, wash the kettle wall with the remaining 2kg of methanol, and react at 70±5°C for 3 hours.

[0060] Reaction monitoring: TLC monitoring [TLC material: G 254 , thickness: 0.2-0.25mm; developing agent, ethyl acetate: petroleum ether (4:3), 254 / 345nm ultraviolet color development] until the conversion of raw materials is complete.

[0061] ③. After the reaction is completed, lower the temperature to about 40°C, and recover methanol (about 35L) under reduced pressure at 40-45°C. The residue was a light yellow oily substance, 50 kg of purified water (the ...

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Abstract

The invention discloses a synthesis method of R-lansoprazole. The method comprises the following steps: by using 1S-(+)-10-camphorsulfonyl oxaziridine as an oxidizer, lansoprazole thioether as a raw material and DBU (1,8-diazabicyclo(5.4.0)undec-7-ene) as an alkali, carrying out asymmetric oxidization in isopropanol, and carrying out separation and purification to obtain R-lansoprazole. The synthesis method is simple to operate, and has the advantages of fewer types of reaction raw materials, higher product e.e. value, convenient after-treatment process and high raw material conversion rate.

Description

technical field [0001] The invention relates to the technical field of medicine synthesis methods, in particular to a synthesis method of D-lansoprazole. Background technique [0002] D-lansoprazole is a chiral monomer (R-configuration) of lansoprazole, and D-lansoprazole is a proton pump inhibitor, which is a benzimidazole derivative, specific and non-competitive acting on H + / K + -ATPase, treatment of peptic ulcer. Most proton pump inhibitors are fat-soluble and weakly alkaline. After being absorbed into the blood, they enter the acidic environment of the parietal cell secretory tubules and tubule cavities, and the activated products are generally active sulfenic acid and sulfenamide. + / K + -ATPase sulfhydryl coupling forms an irreversible covalent disulfide bond, blocking the H + -K + transport mechanism, thereby inhibiting gastric acid secretion. [0003] U.S. FDA approved on January 30, 2009 the listing of the esophagitis treatment new drug dexlansoprazole (com...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12C07B2200/07
Inventor 张会潘小峰
Owner 成都尚药科技有限公司
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