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Method for preparing bilastine

A raw material and aqueous solution technology, applied in the direction of organic chemistry, can solve the problems of difficult removal of impurities, degradation of drug quality, easy breakage of ether bonds, etc., and achieve the effects of no side reactions, simple operation, and mild reaction conditions

Active Publication Date: 2013-07-24
BEIJING VENTUREPHARM BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In the usual reaction, inorganic acid is used as the reaction solvent, the ether bond is easy to break, and the generated impurities are not easy to remove, and the yield is medium
The appearance of by-products will lead to a decrease in the quality of the drug and a decrease in the yield

Method used

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  • Method for preparing bilastine
  • Method for preparing bilastine
  • Method for preparing bilastine

Examples

Experimental program
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Effect test

Embodiment 1

[0022] 10g 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 dissolved in 200ml ethyl acetate, add 0.6g 4-butylammonium hydrogensulfate, sodium hypochlorite 130ml aqueous solution, stirred at room temperature for 12 hours, acidified with hydrochloric acid to pH1 H NMR (400MHz, CD 3 OD), δ(ppm): 1.08(t, 3H), 1.51(s, 6H), 2.17-2.28(m, 4H), 2.82-2.97(m, 4H), 3.07-3.12(m, 2H), 3.43 (q, 3H), 3.58(d, 2H), 3.77(t, 2H), 4.5(t, 2H), 7.18 (d, 2H), 7.21-7.30(m, 2H), 7.39(d, 2H), 7.49-7.63(m, 2H).

Embodiment 2

[0024] 10g 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 was dissolved in 200ml of ethyl acetate, and 0.6g of 4-butylammonium hydrogensulfate was added, once Potassium chlorate aqueous solution 130ml, stirred at room temperature for 12 hours, acidified with hydrochloric acid to pH1 H NMR (400MHz, CD 3 OD), δ(ppm): 1.08(t, 3H), 1.51(s, 6H), 2.17-2.28(m, 4H), 2.82-2.97(m, 4H), 3.07-3.12(m, 2H), 3.43 (q, 3H), 3.58(d, 2H), 3.77(t, 2H), 4.5(t, 2H), 7.18 (d, 2H), 7.21-7.30(m, 2H), 7.39(d, 2H), 7.49-7.63(m, 2H).

Embodiment 3

[0026] 10g 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 was dissolved in 200ml of ethyl acetate, and 0.6g of 4-butylammonium hydrogensulfate was added, hydrogen Add 130ml of sodium oxide aqueous solution, add chlorine gas, stir at room temperature for 18 hours, acidify with hydrochloric acid to pH1 H NMR (400MHz, CD 3 OD), δ(ppm): 1.08(t, 3H), 1.51(s, 6H), 2.17-2.28(m, 4H), 2.82-2.97(m, 4H), 3.07-3.12(m, 2H), 3.43 (q, 3H), 3.58(d, 2H), 3.77(t, 2H), 4.5(t, 2H), 7.18 (d, 2H), 7.21-7.30(m, 2H), 7.39(d, 2H), 7.49-7.63(m, 2H).

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Abstract

The invention belongs to the field of medicine chemicals, and particularly relates to a method for preparing bilastine. The method comprises the following steps of dissolving 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazole-2-based)-1-methyl-ethyl]-phenyl}-ethyl)-piperidine-4-based]-1-(2-ethoxyl-ethyl)-1H-benzimidazole in an organic solvent, adding a certain amount of 4-butyl ammonium hydrogen sulfate and a hypochlorite water solution, reacting for 1-24 hours based on heating at a certain temperature, and treating the reaction liquid to obtain bilastine. The method is mild in conditions and simple in operation; and the method has the advantages of easily available raw materials, simplicity in operation, high yield and convenience for industrial production.

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 (see formula below), chemical name 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzimidazol-2-yl]-piper Pyridin-1-yl}ethyl)-phenyl]-2-methyl-propionic acid, CAS No. 202189-78-4, the second generation of histamine H developed by Spanish FAES pharmaceutical company 1 Receptor antagonist, compared with the original drug, its drug has good safety, no sedative effect and cardiotoxicity of commonly used antihistamine drugs, etc. It was first launched in Ireland in 2011 for the treatment of allergic rhinitis and chronic idiopathic urticaria. [0003] [0004] There are currently two synthetic routes for bilastine: [0005] (1) In the patent CN 1176964A, 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-1- Methyl-e...

Claims

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Application Information

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IPC IPC(8): C07D401/04
Inventor 李铁马苏峰闫起强
Owner BEIJING VENTUREPHARM BIOTECH
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