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Propanol amine kind ether compound synthesized using paeonol as mother body and its derivative

A technology of propanolamine ethers and ether compounds, which is applied in the field of compounds, can solve problems that have not been reported, and achieve the effects of enhanced prevention and control, less toxic and side effects, and strong pharmacological activity

Inactive Publication Date: 2004-07-21
李如法
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] Paeonol (ie 2--hydroxy-4-methoxy-acetophenone Synthesizing the ether compound drugs of propanolamines as the parent has not yet been reported, and the antipyretic, analgesic, antispasmodic, and hypotensive effects of paeonol are combined with propanolamines with ether bonds to play a role Enhance the effect of prevention and treatment of cardiovascular and cerebrovascular diseases, and as the preparation of β-adrenoceptor blocker drugs, have not been reported

Method used

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  • Propanol amine kind ether compound synthesized using paeonol as mother body and its derivative
  • Propanol amine kind ether compound synthesized using paeonol as mother body and its derivative
  • Propanol amine kind ether compound synthesized using paeonol as mother body and its derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of paeonolol (namely the preparation of the etherified compound of propanolamines with paeonol as parent)

[0040] The chemical name of Dampirol is: 1-isopropylamino-3-(2-acetyl-5-methoxy-phenoxy)-2-propanol, and its structural formula is as follows:

[0041]

[0042] Take 25 grams of paeonol and 40 milliliters of epichlorohydrin, add 7 grams of sodium hydroxide, react at 90 ° C for 3 hours, add 50 milliliters of water, separate the water layer, evaporate the water, add 60 milliliters of isopropylamine to react After 10 hours, excess isopropylamine was evaporated, 40 ml of xylene was added, and the mixture was left overnight. The precipitate was recrystallized with ethanol to obtain 21.5 g of product.

[0043] m.p.129~131℃.

[0044] IR:

[0045] 1253 (Ar-O-), 1602 (C=C), 1425(-CH 3 ),

[0046]

[0047] 2.82(1H, Sept, J=6.0Hz, 2.67-2.77 (1H, m, N-CH), 2.87-2.96 (1H, m, N-CH), 3.84 (3H, s, CH) 3 O), 4.05 (3H, br, s + m, OCH, O...

Embodiment 2

[0054] Example 2: Preparation of 1-isopropylamino-3-(2-propionyl-5-methoxy-phenoxy)-2-propanol

[0055] Take 25 g of 2-hydroxy-4-methoxy-propiophenone and 40 ml of epichlorohydrin, add 7 g of sodium hydroxide, react at a temperature of 100 ° C for 3 hours, add 50 ml of water, separate the water layer, evaporate Remove water, add 60 ml of isopropylamine to react for 10 hours, evaporate excess isopropylamine, then add 40 ml of xylene, leave overnight, and recrystallize the precipitate with ethanol to obtain 20.1 g of product.

[0056] m.p.132~140℃.

Embodiment 3

[0057] Example 3: Preparation of 1-isopropylamino-3-(2-acetyl-5-ethoxy-phenoxy)-2-propanol

[0058]Take 25 g of 2-hydroxy-4-ethoxy-acetophenone and 40 ml of epichlorohydrin, add 7 g of sodium hydroxide, react at a temperature of 110 ° C for 5 hours, add 50 ml of water, and remove the water layer, The water was evaporated, 60 ml of isopropylamine was added to react for 11 hours, the excess isopropylamine was evaporated, 40 ml of xylene was added, and the mixture was left overnight. The precipitate was recrystallized with ethanol to obtain 19.6 g of product.

[0059] m.p.143~148℃.

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Abstract

A propanol amine type ether compound prepared from paeonol and its application in preparing the beta-adrenoreceptor paralyser kind of medicines for preventing and treating cardiovascular and cerebrovascular diseases are disclosed. Said ether compound is 1-isopropylamino-3-(2-acetyl-5-methoxy-phenoxy)-2-propanol. Its advantages are high pharmacological activity and low toxic by-effect.

Description

Technical field: [0001] The present invention relates to a class of compounds, in particular to a kind of ether compound which takes paeonol as parent to synthesize propanolamines and its application in the preparation of beta-adrenoceptor blocker medicinal compounds. Background technique: [0002] The general structural formula of propanolamine ether compounds is: [0003] [0004] At present, the application of ether compounds belonging to propanolamines in the preparation of β-adrenoceptor blockers has been confirmed in various literature reports. include: [0005] (1) See "Chinese Pharmacopoeia" two pages 683-684 in 2000 for propranolol hydrochloride, and its structural formula is: [0006] [0007] (2) See pages 341-342 of the second part of "Chinese Pharmacopoeia" in 2000 for atenolol, and its structural formula is: [0008] [0009] (3) Oxenolol is shown on pages 713-714 of the second part of "Chinese Pharmacopoeia" in 2000, and its structural formula is: ...

Claims

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Application Information

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IPC IPC(8): A61K31/138A61K31/195A61P9/00C07C213/02C07C217/64C07C229/34
Inventor 李如法温旭辉窦后松
Owner 李如法
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