Preparation method of muscarinic receptor antagonist glycopyrronium bromide

A technology of muscarinic receptors and glycopyrronium bromide, applied in the field of medicine

Inactive Publication Date: 2013-06-19
SHENYANG PHARMA UNIVERSITY +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The preparation method of existing glycopyrrolate bromide all ex

Method used

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  • Preparation method of muscarinic receptor antagonist glycopyrronium bromide
  • Preparation method of muscarinic receptor antagonist glycopyrronium bromide

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Embodiment Construction

[0013] Alpha-cyclopentylmandelic acid (5)

[0014] Magnesium chips (1.5g, 62mmol), anhydrous ether (20mL) and a small amount of iodine were added to a 250mL three-necked flask. Heated to 30°C, and a small amount of bromocyclopentane ( 3 ) diethyl ether solution, heating to initiate the reaction, when the iodine color disappears, add dropwise under stirring 3 (8.94g, 60mmol) in diethyl ether (15mL), heated to 37°C and refluxed for 20min after dropping, then cooled to 0~5°C. Join in batches 2 (3g, 20mmol), after the addition, add 40mL of anhydrous diethyl ether, raise the temperature to 30°C, stir for 10h, add hydrochloric acid (30mL, 4 mol / L) and stir until the solid is completely dissolved, separate the diethyl ether layer, and wash the water layer with diethyl ether (20mL , 20mL, 10mL) extracted three times. Combine the ether layers, extract twice with 10% sodium carbonate aqueous solution (60mL, 40mL), combine the water layers, adjust the pH to 1~2 with concentrated hy...

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Abstract

The invention belongs to the technical field of medicine and discloses a preparation method of muscarinic receptor antagonist glycopyrronium bromide. The preparation method of the muscarinic receptor antagonist glycopyrronium bromide is characterized in that Alpha-cyclopentyl mandelic acid methyl ester is obtained by aceptophenone ketonic acid Grignard reaction and esterification reaction, and then glycopyrronium bromide is obtained by N-methyl pyrrolidine-3-alcohol ester exchange and quaterisation.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to a preparation method of glycopyrronium bromide. Background technique: [0002] Glycopyrrolate (1), the chemical name is 3-(α-cyclopentylhydroxyphenylacetoxy)-1,1-dimethylpyrrolidinium bromide salt, developed by Shionogi Company of Japan, in 1982 Approved for marketing in the United States, the preparation currently on the market in China is a tablet, and the trade name is Weichangning. This product is a muscarinic receptor (M receptor) antagonist, clinically used for gastric and duodenal ulcers, chronic gastritis, gastric hypersecretion and other diseases. [0003] U.S. Patent US2956062 reports that glycopyrronium bromide can be raw material with α-cyclopentyl mandelic acid methyl ester, and can be combined with N -Methylpyrrolidin-3-ol can be obtained through transesterification reaction and quaternization reaction with methyl bromide. There are three main methods for the pre...

Claims

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Application Information

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IPC IPC(8): C07D207/12
Inventor 王钝于航魏小飞
Owner SHENYANG PHARMA UNIVERSITY
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