Synthetic method for irbesartan

A synthesis method and intermediate technology, applied in the field of synthesis of antihypertensive drugs, can solve problems such as complex operation steps, high production cost, and complicated operation, and achieve the effects of simplified operation process, increased yield, and simple process operation

Active Publication Date: 2012-06-13
浙江弘盛药业有限公司
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Problems solved by technology

[0012] The present invention aims to provide a kind of irbesartan with fewer technical steps, simple operation and high yield, aiming at the defects of the existing irbesartan synthesis method, such as complex operation steps, harsh conditions, complicated operation, various raw materials and high production cost. synthesis method

Method used

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  • Synthetic method for irbesartan
  • Synthetic method for irbesartan
  • Synthetic method for irbesartan

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Embodiment Construction

[0030] The invention will be further described below in conjunction with the examples, and the non-limiting examples are as follows.

[0031] Preparation of intermediate (I) 2-butyl-1,3-diazaspiro[4,4]nonan-1-en-4-one:

[0032] Put 16.5g (0.15mol) of aminocyclopentanitrile in a 250mL flask, add 100mL THF and mechanically stir until the raw material is dissolved, add dropwise a THF solution of 18.0g (0.15mol) of valeryl chloride under stirring, continue stirring for 0.5h, add water 20mL, 50mL of methanol and 20g of potassium hydroxide, reflux for 5h, concentrate under reduced pressure, add water and ethyl acetate to the concentrate for extraction, dry the organic phase with anhydrous magnesium sulfate, filter, and concentrate the filtrate to obtain 27.0g of an oily substance. The rate is 92.7%.

[0033] Intermediate (II) 2-butyl-3-[(2′-cyanobiphenyl-4-yl)methyl]-1,3-diazaspiro[4,4]non-1-ene- Preparation of 4-keto:

[0034] Intermediate (I) 19.4g (0.1mol), 4'-(bromomethyl)-2-...

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Abstract

The invention discloses a synthetic method method for irbesartan. The method comprises the following steps of: hydrolyzing amino cyclopentyl cyanogen serving as a raw material in an alkaline solution to obtain amino cyclopentyl formamide; undergoing a cyclization reaction on the obtained amino cyclopentyl formamide and valeryl chloride to obtain 2-butyl-1,3-diazaspiro[4,4]nonane-1-alkene-4-ketone serving as an intermediate (I); undergoing a C-N coupling reaction on the intermediate (I) and 4-bromomethyl-2'-cyanobiphenyl to obtain 2-butyl-3-[(2'-cyanobiphenyl-4-radical)methyl]-1, 3-diazaspiro[4,4]nona-1-alkene-4-ketone serving as an intermediate (II); undergoing a sodium nitride cyclization reaction to obtain irbesartan serving as a target product. Due to the adoption of the synthetic method, the total yield of the irbesartan product is increased from below 45 percent to over 75 percent, the tonnage consumption the product is greatly lowered, and cost is greatly lowered. An operation process is simplified, so that the yield is increased, three-waste pollution is lowered, treatment is easy, and a novel process with high competitiveness is realized.

Description

1. Technical field [0001] The invention relates to a synthesis method of antihypertensive drugs, in particular to a synthesis method of irbesartan. 2. Background technology [0002] Hypertension is one of the common diseases that seriously endanger people's health and requires long-term and effective treatment. At present, there are more than 120 types of drugs for the treatment of hypertension, including calcium antagonists, angiotensin-converting enzyme inhibitors, α-receptor blockers, diuretics, β-receptor blockers and other five major antihypertensive drugs . [0003] Irbesartan (irbesartan), CAS number: 138402-11-6, chemical name 2-butyl-3-[[2′-(1H-tetrazol-5-yl)-[1,1′-linked Benzene]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one, its structural formula is as follows: [0004] [0005] Irbesartan is a long-acting angiotensin II receptor antagonist with a half-life of 11-15 hours. It was first launched in the UK in 1997 for the treatment of high blood pressure und...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10
Inventor 冯乙巳耿烨叶加久齐洪霞章丰丰
Owner 浙江弘盛药业有限公司
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