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Process for preparing olmesartan medoxomil at ph higher than 2.5

A technology for olmesartan medoxomil and trityl olmesartan medoxomil is applied in the field of impurity olmesartan medoxomil and can solve problems such as product decomposition

Inactive Publication Date: 2007-12-26
TEVA PHARMA IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Continued exposure to acidic conditions may cause product to decompose

Method used

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  • Process for preparing olmesartan medoxomil at ph higher than 2.5
  • Process for preparing olmesartan medoxomil at ph higher than 2.5
  • Process for preparing olmesartan medoxomil at ph higher than 2.5

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Comparative example using acetic acid

[0031] A solution of MTT dissolved in 10 volumes of acetic acid (75%) was heated at 60°C for 1.5 hours to obtain pH 2.21-2.23, and the reaction was stirred until the amount of MTT was less than 2%. The mixture was evaporated to dryness. Ethyl acetate (EtOAc, 1 volume) was added to the residue followed by evaporation (twice). The resulting solid was dissolved in EtOAc (12 volumes) and heated to reflux. The solution was cooled (2°C) and stirred for 2 hours. The product was filtered, washed (EtOAc, 1 volume) and dried under vacuum (45°C).

Embodiment 2

[0033] A solution of MTT in organic solvent and water (20%) is heated to reflux for 4-8 hours. When the solvent is acetonitrile (ACN), isopropanol (IPA) or tert-butanol (tert-BuOH), add 1 volume of water and stir the reactants until the amount of MTT is less than 2%. The mixture was evaporated to dryness. Ethyl acetate (EtOAc, 1 volume) was added to the residue followed by evaporation (twice). The resulting solid was dissolved in EtOAc (12 volumes) and heated to reflux. The solution was cooled (2°C) and stirred for 2 hours. The product was filtered, washed (EtOAc, 1 volume), and dried under vacuum (45°C).

[0034] Table 1 shows the details of the method using different organic solvents:

[0035] Table 1

[0036] Total solvent

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Abstract

The present invention provides a process for preparing olmesartan medoxomil at pH higher than 2.5.

Description

[0001] This application claims to enjoy the rights of U.S. Provisional Patent Application Serial No. 60 / 640,183 filed on December 30, 2004. Invention field [0002] The present invention relates to a method for preparing olmesartan medoxomil containing reduced levels of impurities. Background technique [0003] The chemical name of Olmesartan medoxomil is 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2′-(1H-tetrazol-5-yl)[1,1′ -Biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ( Merck Index 13th Edition). [0004] The chemical structure of Olmesartan medoxomil is: [0005] [0006] The chemical formula is C 29 H 30 N 6 O 6 . [0007] The molecular weight is 558.58. [0008] Olmesartan medoxomil is a prodrug that is hydrolyzed during absorption, and it is a selective AT 1 Subtype angiotensin II receptor antagonist. Olmesartan medoxomil was disclosed by Yanagisawa et al. in US Patent No. 5,616,599. It is sold as BENICAR(R) and 5mg, 20mg and 40...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10
CPCC07D405/14A61P9/12
Inventor L·赫瓦蒂G·皮拉斯基N·申卡-佳西亚
Owner TEVA PHARMA IND LTD