Method for synthesizing chiral ilaprazole

A synthetic method and chiral technology, which is applied in the field of new process route of optically active ilaprazole, can solve the problem that ilaprazole has no chiral compound, and achieve the effect of novel process, fewer steps and mild reaction conditions

Inactive Publication Date: 2018-11-13
SHENZHEN HUAXIAN PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In summary, there is currently no chiral compound report for ilaprazole, and the resolution schemes of other proton pump inhibitor types of compounds have certain defects. The new method for developing chiral ilaprazole requires existing technology Significance in development, especially in new drug research

Method used

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  • Method for synthesizing chiral ilaprazole
  • Method for synthesizing chiral ilaprazole
  • Method for synthesizing chiral ilaprazole

Examples

Experimental program
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Effect test

Embodiment 1

[0022] 1. Synthesis of chiral ilaprazole

[0023] Take a 100 mL three-necked flask and add sulfide (10 mmol), biguanide salt phase transfer catalyst A (0.1 mmol) and isopropyl ether (40 mL) to it in sequence under the protection of nitrogen. Then sodium tungstate (0.2 mmol) was added, followed by aqueous peroxyacetic acid (12 mmol). After reacting at 0°C for 8 hours, it was quenched with sodium sulfite aqueous solution and separated. The organic phase is desolventized, and then recrystallized with ethanol to obtain white crystals with a total yield of 90%, an ee value of 99%, and levorotatory.

[0024] The structure and product structure of catalyst A are as follows:

[0025]

Embodiment 2

[0027] 1. Synthesis of chiral ilaprazole

[0028] Take a 100 mL three-necked flask and add sulfide (10 mmol), biguanide salt phase transfer catalyst B (0.1 mmol) and isopropyl ether (40 mL) to it in sequence under the protection of nitrogen. Then sodium molybdate (0.2 mmol) was added, followed by aqueous hydrogen peroxide solution (12 mmol). After reacting at 0°C for 8 hours, it was quenched with sodium sulfite aqueous solution and separated. The organic phase was desolventized, and then recrystallized with ethanol to obtain white crystals with a total yield of 90%, an ee value of 99%, and dextrorotation.

[0029] The structure of catalyst A is as follows:

[0030]

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Abstract

Disclosed is a method for synthesizing chiral ilaprazole. The invention belongs to the technical field of pharmacy. At present, reports about ilaprazole chiral compounds are few. The method includes the following steps: under the protection of nitrogen, adding a phase transfer catalyst and isopropyl ether into thioether in order, adding central metal, adding an oxidant, carrying out quenching withan aqueous sodium sulfite solution after reacting at 0 DEG C for 8 hours, carrying out liquid separation, carrying out organic phase desolvation, and then recrystallizing with ethanol to obtain whitecrystals which are the chiral ilaprazole. The method can be used for pharmaceutical research and industrial production of the chiral eprazole. The method has the characteristics of a novel process, few steps, mild reaction conditions and the like.

Description

Technical field [0001] The invention belongs to the technical field of pharmacy, and specifically relates to a new process route of optically active ilaprazole. Background technique [0002] Ilaprazole is a proton pump inhibitor developed and marketed by Livzon Group, with the trade name "Yilian". It belongs to a class 1 new drug and is used to treat duodenal ulcers. [0003] Other proton pump inhibitor drugs, such as omeprazole, lansoprazole, pantoprazole, and rabeprazole, have corresponding single chiral compounds on the market, namely esomeprazole and dextran Soprazole, levopantoprazole, and dexrabeprazole. However, ilaprazole is currently used in medicine as a racemate, and its single chiral compound has not been reported yet. [0004] [0005] When a chiral compound enters a living body, its two enantiomers usually exhibit different biological activities. For chiral drugs, one isomer may be effective, while the other isomer may be ineffective or even harmful. For example, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14
CPCC07B2200/07C07D401/14
Inventor 周章涛费安杰孙家强徐俊烨颜燕南
Owner SHENZHEN HUAXIAN PHARMA TECH CO LTD
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