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Optically active ilaprazole and synthesis method thereof

A technology of ilaprazole and optical activity, applied in the field of optically active ilaprazole and its new process route, can solve the problems of ilaprazole not easy to split, many by-products in the oxidation step, and difficult to control metal residues, etc. Achieve the effect of novel process, mild reaction conditions and few steps

Inactive Publication Date: 2018-10-23
SHENZHEN HUAXIAN PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The present invention aims to solve the technical problems that the existing preparation of ilaprazole is not easy to split, it is difficult to control metal residues, and there are many by-products in the oxidation step, which are difficult to separate and purify; and an optically active ilaprazole and its resolve resolution

Method used

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  • Optically active ilaprazole and synthesis method thereof
  • Optically active ilaprazole and synthesis method thereof
  • Optically active ilaprazole and synthesis method thereof

Examples

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Embodiment 1

[0030] 1. Synthesis of Thioether Compounds

[0031] Take a 100mL three-necked flask, add 5-(1H-pyrrol-1-yl)-1H-benzimidazole-2-thiol (2.15g, 0.01mol), ethanol (10mL) and Triethylamine (0.1 g) was then carefully added ethyl acrylate (1.10 g, 0.011 mol). After the reaction is completed, the solvent is removed, and the product is directly used in the next step.

[0032] 2. Synthesis of racemic sulfoxide compounds

[0033] Take a 100mL three-necked flask, and add the product from the previous step, acetonitrile (20mL) and 10% aqueous sodium hydroxide solution (5mL) to it under nitrogen protection, and then carefully add 10% aqueous sodium hypochlorite (8.2mL, 1.1eq. ). After the reaction was completed, it was acidified to pH=3 with dilute hydrochloric acid, and filtered. The filter cake is beaten with ethanol, filtered, and put into the next step after vacuum drying.

[0034] 3. Synthesis of Chiral Ilaprazole

[0035] Get a 100mL three-necked flask, add the product of the pr...

Embodiment 2

[0041] 1. Synthesis of Thioether Compounds

[0042] Take a 100mL three-necked flask, add 5-(1H-pyrrol-1-yl)-1H-benzimidazole-2-thiol (2.15g, 0.01mol), ethanol (10mL) and Triethylamine (1.1 g) was then carefully added ethyl bromopropionate (1.80 g, 0.011 mol). After the reaction is completed, filter and remove the solvent, and the product is directly used in the next step.

[0043] 2. Synthesis of racemic sulfoxide compounds

[0044] Take a 100mL three-necked flask, under the protection of nitrogen, add the product from the previous step, acetonitrile (20mL), and then carefully add m-chloroperoxybenzoic acid (1.9g, 1.1eq.). After the reaction is complete, filter. The filtrate was concentrated, 10 ml of methanol was added, filtered, and the filter cake was vacuum-dried and used in the next step.

[0045] 3. Synthesis of Chiral Ilaprazole

[0046] Get a 100mL three-necked flask, add the product of the previous step, methylcyclohexane (20mL) and 67% cesium hydroxide solution ...

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Abstract

The invention relates to optically active ilaprazole and a synthesis method thereof, belongs to the field of pharmaceutical technology, and discloses a method for synthesizing optically active ilaprazole. According to the method, corresponding thiol is used as a starting raw material, and reacts with acrylate or halopropionate to obtain a thioether compound, the thioether compound is oxidized to obtain racemic sulfoxide, and the racemic sulfoxide reacts with another fragment under the action of a chiral phase transfer catalyst to obtain the chiral ilaprazole. According to the present invention, the preparation of the chiral ilaprazole is firstly reported, the synthesis method of the chiral ilaprazole does not require the use of heavy metals and the use of dangerous peroxides, and the excessive oxidation by-product is generated at the penultimate chemical step so as to easily control; and the method has characteristics of novel process, few steps, mild reaction conditions and the like.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, and in particular relates to an optically active ilaprazole and a new process route thereof. Background technique [0002] Ilaprazole is a proton pump inhibitor developed and marketed by Livzon Group. Its trade name is "Yili'an". It belongs to Class 1 new drug and is used for the treatment of duodenal ulcer. [0003] Other proton pump inhibitor drugs, such as omeprazole, lansoprazole, pantoprazole and rabeprazole, have corresponding monochiral compounds on the market, named esomeprazole, dexlan Soprazole, left pantoprazole, and dexrabeprazole. However, ilaprazole is currently used in medicine in the form of a racemate, and its single chiral compound form has not been reported. [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 another isomer may be ineffecti...

Claims

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Application Information

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IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 叶伟平周章涛费安杰徐俊烨颜燕南莫爱丽
Owner SHENZHEN HUAXIAN PHARMA TECH CO LTD
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