Preparation method of Bilastine

A raw material, aqueous solution technology, applied in organic chemistry and other directions, can solve the problems of ether bond cleavage, difficult removal of impurities, difficult product purification, etc., and achieves the effects of mild reaction conditions, no side reactions, and simple operation.

Active Publication Date: 2013-10-16
BEIJING VENTUREPHARM BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Those skilled in the art know that under strong acid conditions, the ether bond has a tendency to break, the impurities generated are difficult to remove, and the product is difficult to purify

Method used

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  • Preparation method of Bilastine
  • Preparation method of Bilastine
  • Preparation method of Bilastine

Examples

Experimental program
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Effect test

Embodiment 1

[0019] 5g 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-1-methyl-ethyl]-benzene Base}-ethyl)-piperidin-4-yl]-1-(2-ethoxy-ethyl)-1H-benzimidazole was added to a clean three-neck flask, 150ml of 4N formic acid solution was added, and heated to reflux for 36 hours , adjusted to pH=7 with 10% aqueous sodium hydroxide solution, extracted with dichloromethane, and the solvent was spinned out to obtain a white solid with a yield of 90.5%.

Embodiment 2

[0021] 5g 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-1-methyl-ethyl]-benzene Base}-ethyl)-piperidin-4-yl]-1-(2-ethoxy-ethyl)-1H-benzimidazole was added to a clean three-necked flask, 150ml of 4N trifluoroformic acid solution was added, and heated to reflux After 36 hours, adjust the pH to 7 with 10% aqueous sodium hydroxide solution, extract with dichloromethane, and spin out the solvent to obtain a white solid with a yield of 92.6%.

Embodiment 3

[0023] 5g 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-1-methyl-ethyl]-benzene Base}-ethyl)-piperidin-4-yl]-1-(2-ethoxy-ethyl)-1H-benzimidazole was added to a clean three-neck flask, 150ml of 4N acetic acid solution was added, and heated to reflux for 36 hours , adjusted to pH=7 with 10% aqueous sodium hydroxide solution, extracted with dichloromethane, and the solvent was spinned out to obtain a white solid with a yield of 89.7%.

[0024]

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Abstract

The invention belongs to the field of medical chemistry, and relates to a preparation method of Bilastine. The preparation method comprises following steps: adding compound 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazole-2-yl)-1-methyl-ethyl]-phenyl}-ethyl)-piperidine-4-yl]-1-(2-ethoxy-ethyl)-1H-benzimidazole into water containing organic acid, then subjecting the mixture to a thermal-reflux reaction for 1 to 36 hours, and finally obtaining Bilastine after post-processing. The preparation method has the advantages of mild reaction conditions, simple operation and easy industrialization.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to bilastine 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzimidazol-2-yl]-piperidine - Preparation of 1-yl}ethyl)-phenyl]-2-methyl-propionic acid. Background technique [0002] Bilastine is the second generation of histamine H developed by Spanish FAES pharmaceutical company 1 Receptor antagonist, approved by the European Union in 2010 for the treatment of allergic rhinitis and chronic idiopathic urticaria. This product is safe, without the sedative effect and cardiotoxicity of commonly used antihistamines. [0003] [0004] II [0005] The usual synthetic route of bilastine is as follows: [0006] In the patent CN 1176964A, 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-1-methyl- Ethyl]-phenyl}-ethyl)-piperidin-4-yl]-1-(2-ethoxy-ethyl)-1H-benzimidazole as raw material, in an aqueous mineral acid solution, such as hydrochloric acid, Under the condition of sulfuric acid, bilas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
Inventor 赵月楠闫起强马苏峰王进敏
Owner BEIJING VENTUREPHARM BIOTECH
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