Preparation method of olmesartan medoxomil

A technology of olmesartan medoxomil and ethyl carboxylate, applied in the field of preparation of olmesartan medoxomil, can solve the problems of low yield, unsuitable for industrialized production, complicated processing steps, etc., and achieves high total yield, time saving, low effect of cost

Active Publication Date: 2012-02-15
山东安信制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing preparation method is to first separate the compound III, and then carry out the next step reaction on the pure product of the obtained compound I

Method used

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  • Preparation method of olmesartan medoxomil
  • Preparation method of olmesartan medoxomil
  • Preparation method of olmesartan medoxomil

Examples

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Embodiment 1

[0024] Add 12g 4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-carboxylic acid ethyl ester and 3.6g sodium hydroxide in the reaction flask, 120ml DMF, add 35g N-(trityl base)-5-(4'-bromomethylbiphenyl-2-)tetrazolium. After the addition, the temperature of the reaction system was raised to 75° C., and the reaction was carried out at this temperature for 10 h. The reaction was monitored by TLC, and the heating was stopped.

[0025] Add lithium hydroxide aqueous solution (2.3g lithium hydroxide monohydrate dissolved in 100ml water) to the above reaction system. After the addition is complete, the temperature rises to 65°C, and the reaction is maintained at this temperature for 3h. After the reaction is monitored by TLC, the reaction system is cooled. To 20°C, add 200 ethyl acetate and 230 ml of water to the reaction solution, separate the layers, extract the water layer twice with 100 ml of ethyl acetate, combine the ethyl acetate layers, and wash the ethyl acetate with 250 ml of...

Embodiment 2

[0028] Add 12g 4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-carboxylic acid ethyl ester and 4g sodium hydroxide in the reaction flask, 120ml DMF, add 31g N-(trityl )-5-(4'-bromomethylbiphenyl-2-)tetrazolium (II), after the addition, the reaction system was heated up to 70°C, and reacted at this temperature for 11h, TLC monitored the completion of the reaction, and stopped heating .

[0029] Add lithium hydroxide aqueous solution (2.5g lithium hydroxide monohydrate dissolved in 100ml water) to the above reaction system. After the addition is complete, the temperature rises to 68°C, and the reaction is maintained at this temperature for 3h. After the reaction is monitored by TLC, the reaction system is cooled. To 20°C, add 200 ethyl acetate and 230 ml of water to the reaction solution, separate the layers, extract the water layer twice with 100 ml of ethyl acetate, combine the ethyl acetate layers, and wash the ethyl acetate with 250 ml of water three times. Dry over anhydr...

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Abstract

The invention discloses a preparation method of olmesartan medoxomil,Which is characterized by reacting ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (I) and N-(triphenylmethyl)-5-(4'-bromoethylbiphenyl-2-)tetrazole (II) by a one-pot process to directly obtain lithium 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(triphenylmethyltetrazolyl-5-yl)phenyl]phenyl}methylimidazol-5-carboxylate (IV). The invention has the advantages of mild reaction conditions, fewer byproducts, high purity of the end product, high total yield, high safety and environmental protection, and is suitable for industrial production; and by using the one-pot process, the invention is simpler to operate, saves the time and lowers the cost.

Description

technical field [0001] The invention relates to a preparation method of olmesartan medoxomil, which belongs to the technical field of medicine. Background technique [0002] Olmesartan medoxomil, molecular formula: C 29 h 30 N 6 o 6 ;Molecular weight: 558.60 [0003] Structural formula: [0004] [0005] Olmesartan medoxomil (olmesartan medoxomil) is a new angiotensin ∏ (AT∏) receptor antagonist, developed by Sankyo Pharma in Japan and developed and produced by Forest Laboratories in the United States. It was first approved by the FDA in May 2002 for the treatment of high Blood pressure, the trade name is Banicar; it was launched in Germany under the trade name of Olmetec in October. As a new angiotensin II receptor antagonist (ARBs), olmesartan medoxomil can inhibit angiotensin ∏ (AT∏). Olmesartan medoxomil is an oral tablet with few adverse reactions and high cost-effectiveness. It is currently used to treat hypertensive patients who are intolerant to angiotensin...

Claims

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Application Information

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IPC IPC(8): C07D405/14
Inventor 李卓华秦春霞常宝磊吴柯张兆珍董廷华李保勇
Owner 山东安信制药有限公司
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