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Preparation method of olmesartan medoxomil

A technology of olmesartan medoxomil and methyl ester, which is applied in the field of preparation of olmesartan medoxomil, can solve the problems of complex processing steps and unfavorable industrial production, and achieve the effects of reducing costs, saving time, and few by-products

Inactive Publication Date: 2013-12-11
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the preparation methods disclosed in existing patent documents (CN102351849A, etc.) are to isolate compound III first, and then carry out the next step reaction with the pure product of compound III, and the processing steps are more complicated; although the patent document with the publication number (CN102050816A) There is no need to separate compound III in the disclosed preparation method, but this technology uses thionyl chloride for reaction, which requires strict anhydrous conditions, which is not conducive to industrial production

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Add 12g4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-carboxylic acid ethyl ester and 3.6g sodium hydroxide, 120ml DMF and 35gN-(triphenylmethyl) in the reaction flask -5-(4'-bromomethylbiphenyl-2-yl)tetrazolium. After the addition, the reaction system was heated up to 75° C., and reacted at this temperature for 10 h. TLC monitored the completion of the reaction, and stopped heating. Add 2.2 g of sodium hydroxide 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 3 hours. After the reaction is completed as monitored by TLC, the reaction system is cooled to 10° C.

[0037] Then, 2 g of cesium carbonate and 9 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one were added to the above system, and the reaction was carried out at room temperature for 2 h. After the reaction was completed, extract with ethyl acetate, wash with saturated aqueous sodium chloride solution twice, dry th...

Embodiment 2

[0040]Add 12g4-(1-hydroxyl-1-methylethyl]-2-propylimidazole-5-ethyl carboxylate and 4g sodium hydroxide in the reaction flask, 120ml DMF, add 31gN-(triphenylmethyl) -5-(4'-bromomethylbiphenyl-2-yl)tetrazolium (II), after the feeding is completed, the reaction system is heated to 70°C, and reacted at this temperature for 11h, TLC monitors that the reaction is complete, stop heating .

[0041] Add 2.2 g of potassium hydroxide 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 3 hours. After the reaction is monitored by TLC, the reaction system is cooled to 5° C.

[0042] Add 2 g of cesium carbonate and 9 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one to the above system, and react at room temperature for 3 h. After the reaction was completed, extract with ethyl acetate, wash with saturated aqueous sodium chloride twice, dry the ethyl acetate layer with anhydrous sodium sulfate, eva...

Embodiment 3

[0045] Add 12g4-(1-hydroxyl-1-methylethyl]-2-propylimidazole-5-carboxylic acid ethyl ester and 3.9g sodium hydroxide, 125ml DMF, add 31g N-(trityl )-5-(4'-bromomethylbiphenyl-2-)tetrazolium (II), after the addition, the temperature of the reaction system was raised to 70°C, and the reaction was carried out at this temperature for 10 hours. The reaction was monitored by TLC, and the heating was stopped. .

[0046] Add 2.1 g of potassium hydroxide to the above reaction system. After the addition is complete, the temperature rises to 67° C., and the reaction is maintained at this temperature for 3 hours. After the reaction is monitored by TLC, the reaction system is cooled to 5° C.

[0047] Add 2 g of cesium carbonate and 9 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one to the above system, and react at room temperature for 2.5 h. After the reaction was complete, extract with ethyl acetate, wash with saturated aqueous sodium chloride twice, dry the ethyl acetate layer with anhydr...

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Abstract

The invention discloses a preparation method of olmesartan medoxomil and relates to the technical field of medicine. The method comprises the following steps: using 4-(1-hydroxy-1-methylethyl)-2-propylimidazol-5-ethylcarboxylate and N-(triphenylmethyl)-5-(4'-bromomethyl diphenyl-2-yl)tetrazole as raw materials, adopting a one-pot method to directly obtain 1-[[[27-(triphenylmethyl)-2H-tetrazole-5-yl]dipheny-4-yl]methyl]-2-propyl-4-(1-hydroxy-1-methylethyl)imidazol-5-carboxylic acid (5-methyl-2-oxo-1,3-dioxycyclopentene-4-yl)methyl ester. Compared with the prior art, the preparation method has the characteristics of simple preparation technology, high yield, low cost and the like, and the method is more beneficial to implementation of large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a preparation method of olmesartan medoxomil. Background technique [0002] Olmesartan medoxomil, molecular formula: C 29 h 30 o 6 N 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 孙敬勇孙捷汪海洋窦春水赵朕雄王延风赵爱慧姚庆强
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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