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Novel preparation of losartan potassium

A technology of losartan potassium and n-butyl, applied in the field of drug synthesis, can solve the problems such as difficulty in obtaining raw materials, and achieve the effect of high reaction efficiency

Inactive Publication Date: 2009-07-08
江苏德峰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is mainly that raw materials are difficult to obtain, especially 2'-(

Method used

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  • Novel preparation of losartan potassium
  • Novel preparation of losartan potassium
  • Novel preparation of losartan potassium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] step a

[0019] Preparation of 2-n-butyl-4-chloro-1-[4-bromo-benzyl]-1H-imido-5-formyl:

[0020] In a 1000ml four-neck flask equipped with a drying tube, a thermometer, a dropping funnel and mechanical stirring, add 2g of 2-n-butyl-4-chloro-1H-imido-5-formyl, dichloromethane, stir to dissolve, and cool down . At -10-0°C (eg -10°C, -5°C, -3°C, 0°C), add 2.5g of p-bromobenzyl bromide in dichloromethane dropwise; after addition, continue the reaction at 0-10°C After 4 to 5 hours, TLC showed that the raw material basically disappeared; adding 5% aqueous sodium bicarbonate solution for washing, washing with saturated brine, and removing dichloromethane from the organic phase under reduced pressure to obtain 2-n-butyl-4-chloro-1-[4 -Bromo-benzyl]-1H-imido-5-formyl 4.2 g. The crude product was directly carried on to the next step without further purification.

[0021] step b

[0022] Preparation of 2-n-butyl-4-chloro-1-[4-bromo-benzyl]-1H-midine-5-methanol:

[0023] The ...

Embodiment 2

[0034] step a

[0035] Preparation of 2-n-butyl-4-chloro-1-[4-bromo-benzyl]-1H-imido-5-formyl:

[0036] In a 1000ml four-necked flask equipped with a drying tube, a thermometer, a dropping funnel and mechanical stirring, add 2-n-butyl-4-chloro-1H-imido-5-formyl 2g, toluene, diisopropylethylamine 3ml, stir to dissolve, and cool down. At -10-0°C, add 2.5g of toluene solution of p-bromobenzyl bromide dropwise; after the addition, continue to react for 6 hours at 0-5°C, TLC shows that the raw materials basically disappear; add 5% aqueous sodium bicarbonate to wash, Wash with saturated brine, and remove toluene from the organic phase under reduced pressure to obtain 4.2 g of 2-n-butyl-4-chloro-1-[4-bromo-benzyl]-1H-imido-5-formyl. The crude product was directly carried on to the next step without further purification.

[0037] step b

[0038] Preparation of 2-n-butyl-4-chloro-1-[4-bromo-benzyl]-1H-midine-5-methanol:

[0039] The product of step a was dissolved in 150 ml of dic...

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PUM

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Abstract

The invention discloses a novel method for preparing losartan potassium, which obtains losartan through the suzuki reaction of a raw material of 2-butyl-4-chloro-1H-imidazole-5-carbaldehyde and 2-[N(triphenylmethyl )- tetrazole ] phenylboronic acid and deprotection. The method saves a step of generating tetrazole and ensures high-efficiency and safe reaction.

Description

technical field [0001] The invention belongs to the synthesis of medicines, in particular to a new preparation method of losartan potassium, wherein the intermediate 2-n-butyl-4-chloro-1-[[2'-(N'-trityl-tetrazolium- 5-yl)-[1,1'-biphenyl]-4-yl]methyl]-1H-imido-5-methanol (2); the structural formula of losartan potassium is shown in 1, the middle The structure of the body is shown in Figure 2. [0002] [0003] 2-n-Butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl]-1H-imidium Block-5-methanol monopotassium salt is usually named losartan potassium, which has great application in the treatment of hypertension. Is a popular non-peptide angiotensin II (AT II) receptor antagonist. Background technique [0004] Most of the existing syntheses of losartan potassium start from biphenyl derivatives, and some biphenyl derivatives directly start from tetrazole biphenyl derivatives. The starting point is relatively high, and the raw materials are not easy to obtain...

Claims

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Application Information

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IPC IPC(8): C07D403/10A61P9/12
Inventor 王德峰
Owner 江苏德峰药业有限公司
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