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A process for the preparation of olmesartan medoxomil

A technology of olmesartan medoxomil and trityl olmesartan medoxomil, which is applied in the field of organic synthesis and can solve problems such as lack of experimental support

Inactive Publication Date: 2010-07-14
LEK PHARMA D D
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no experimental support for this method

Method used

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  • A process for the preparation of olmesartan medoxomil
  • A process for the preparation of olmesartan medoxomil
  • A process for the preparation of olmesartan medoxomil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1:-One-pot synthesis of trityl olmesartan medoxomil (6)

[0074] 4g (16.7mmol) 4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-ethyl carboxylate (2), 9.28g (16.7mmol) 4-[2-(triphenyl Methyltetrazol-5-yl)phenyl]benzyl bromide (3) and 0.7 g (16.7 mmol) of lithium hydroxide hydrate were suspended in 70 mL of N,N-dimethylacetamide.

[0075] The reaction mixture was stirred at 50° C. for 3 hours, and then 1.05 g (25 mmol) of lithium hydroxide hydrate was added to the reaction mixture. The reaction mixture was stirred at 50 °C for a further 40 hours, then a third portion of lithium hydroxide hydrate (0.35 g, 8.33 mmol) was added and 3.84 g (24.6 mmol) of 4-chloromethyl-5-methyl was added in portions - 1,3-dioxol-2-one (7) (94%) in 10 mL of N,N-dimethylacetamide.

[0076] Completion of the reaction required further stirring of the reaction mixture at 50°C for 7 hours. To precipitate the product, the reaction mixture was poured into 400 mL of water and the resul...

Embodiment 2

[0077] Embodiment 2:-One-pot synthesis of trityl olmesartan medoxomil (6)

[0078] 4g (16.7mmol) 4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-ethyl carboxylate (2), 9.28g (16.7mmol) 4-[2-(triphenyl Methyltetrazol-5-yl)phenyl]benzyl bromide (3) and 1.75 g (41.6 mmol) of lithium hydroxide hydrate were suspended in 70 mL of N,N-dimethylacetamide.

[0079] The reaction mixture was stirred at 50 °C for 46 h, then 2.53 g (18.32 mmol) of K 2 CO 3And 4.0 g (23.0 mmol) 4-chloromethyl-5-methyl-1,3-dioxol-2-one ( 7) (85%). The reaction mixture was stirred at 50 °C for an additional 5 hours to complete the reaction.

[0080] The product was precipitated from the reaction mixture by pouring it into 400 mL of a mixture of water and acetone (V / V=95 / 5). The resulting suspension was stirred overnight and the precipitate was filtered and washed with 200 mL of water. The wet cake was recrystallized in acetone to yield 9.95 g (75%) of trityl olmesartan medoxomil (6) (HPLC purity 97.7 ...

Embodiment 3

[0081] Embodiment 3:-One-pot synthesis of trityl olmesartan medoxomil (6)

[0082] 4g (16.7mmol) 4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-ethyl carboxylate (2), 9.28g (16.7mmol) 4-[2-(triphenyl Methyltetrazol-5-yl)phenyl]benzyl bromide (3) and 0.7 g (16.7 mmol) of lithium hydroxide hydrate were suspended in 70 mL of N,N-dimethylacetamide. The reaction mixture was stirred for 45 minutes, then a further portion of lithium hydroxide hydrate (2.10 g, 50 mmol) was added to the reaction mixture. After stirring at 50°C for 48 hours, 4.9 g (31.0 mmol) of 4-chloromethyl-5-methyl-1,3-dioxa in 10 mL of N,N-dimethylacetamide was added in portions Cyclopenten-2-one (7) (94%). The reaction mixture was further stirred at 50 °C for 6 hours to complete the reaction. The product was precipitated from the reaction mixture by pouring it into 400 mL of a mixture of water and acetone (V / V=95 / 5). The resulting suspension was stirred overnight and the precipitate was filtered and washed...

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Abstract

The present invention relates to a process for the preparation and purification of trityl olmesartan medoxomil and olmesartan medoxomil.

Description

field of invention [0001] The present invention belongs to the field of organic synthesis and relates to methods for preparing and purifying trityl olmesartan medoxomil and olmesartan medoxomil. Background of the invention [0002] The generic name of Olmesartan medoxomil is 1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2 -Propyl-1H-imidazole-5-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester, as shown in (1) below. This chemical is known as an angiotensin-II receptor antagonist and is used as an antihypertensive drug. [0003] [0004] Diagram 1 [0005] According to the literature J.Med.Chem of Yanagisawa et al., 1996, 39, 323-338, titled Nonpeptide Angiotensin II Receptor Antagonists (non-peptide angiotensin II receptor antagonist), olmesartan medoxomil is shown in the following scheme 2 preparation. In this method, chemical intermediates are isolated in various steps. [0006] [0007] Diagram 2 [0008] Two improved meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14
CPCC07D405/14A61P9/00A61P9/12
Inventor R·托普拉克卡萨尔
Owner LEK PHARMA D D
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