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Benzofuran acetamide compound containing propanolamine structure and application thereof

A technology of benzofuran and compounds, which is applied to benzofuran acetamide compounds. Its application field as a β-receptor blocker can solve the problems of different side effects of antihypertensive drugs, and achieve good hypertension, The effect of good application value and good development and application prospects

Active Publication Date: 2021-11-12
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there are many kinds of antihypertensive drugs, and different antihypertensive drugs are suitable for different symptoms, but all antihypertensive drugs have different side effects, and some even cause other complications

Method used

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  • Benzofuran acetamide compound containing propanolamine structure and application thereof
  • Benzofuran acetamide compound containing propanolamine structure and application thereof
  • Benzofuran acetamide compound containing propanolamine structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Preparation of 1-(4-morpholinyl)-2-{6-[2-hydroxyl-3-(isopropylamino)propoxy]benzofuran-3-yl}ethanone (TX01)

[0048] Step A: Preparation of 1-(4-morpholinyl)-2-(6-hydroxybenzofuran-3-yl)ethanone

[0049] 2-(6-Hydroxy-1-benzofuran-3-yl)acetic acid (5.7g, 30mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodi Imine hydrochloride (EDCI, 8.0g, 42mmol), 1-hydroxybenzotriazole (HOBt, 5.7g, 42mmol), morpholine (90mmol) and 90mL of dry dichloromethane, refluxed for 24h, and the reaction solution was washed with 20mL Wash three times with 6% hydrochloric acid, wash three times with 20mL 5% sodium hydroxide solution, wash twice with 20mL saturated sodium chloride solution, dry the organic layer with anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and perform column chromatography [petroleum ether: ethyl acetate (V:V)=3:1], 3.3 g of white solid was obtained, and the yield was 42.1%. m.p.: 176-179°C. ESI-MS(m / z):262.1([M+H] + ); 1 H-NMR (400MHz, CD...

Embodiment 2

[0054] Example 2: Preparation of 1-(4-morpholinyl)-2-{6-[2-hydroxyl-3-(tert-butylamino)propoxy]benzofuran-3-yl}ethanone (TX02)

[0055] Referring to the preparation method of Example 1, 0.82 g of yellow solid was obtained, yield: 52.8%. m.p.: 146-148°C. ESI-MS(m / z):391.2([M+H] + ); 1 H-NMR (600MHz, CDCl 3 )δ7.46(s,1H),7.45(d,J=8.5Hz,1H),7.01(d,J=2.1Hz,1H),6.90(dd,J 1 =8.6Hz,J 2 =2.2Hz,1H),4.07-4.10(m,1H),4.04(dd,J 1 =9.3Hz,J 2 =5.3Hz,1H),4.00(dd,J 1 =9.3Hz,J 2 =5.0Hz,1H),3.72(s,2H),3.65(s,4H),3.56–3.53(m,2H),3.50–3.47(m,2H),2.95(dd,J 1 =12.0Hz,J 2 =3.6Hz,1H),2.77(dd,J 1 =11.9Hz,J 2 =8.1Hz, 1H), 1.19(s, 9H).

Embodiment 3

[0056] Example 3: Preparation of N,N-diethyl-2-{6-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran-3-yl}acetamide (TX03)

[0057] Referring to the preparation method of Example 1, 0.84 g of light yellow solid was obtained, yield: 58.3%. m.p.: 167-169°C. ESI-MS(m / z):363.2([M+H] + ); 1 H-NMR (600MHz, CDCl 3 )δ7.45(s,1H),7.41(d,J=8.6Hz,1H),6.96(d,J=2.0Hz,1H),6.85(dd,J 1 =8.6Hz,J 2 =2.1Hz, 1H), 4.47(d, J=4.9Hz, 1H), 4.05(dd, J 1 =9.6Hz,J 2 =4.7Hz,1H),3.97(dd,J 1 =9.5Hz,J 2 =5.7Hz,1H),3.65(s,2H),3.38(q,J=7.1Hz,2H),3.34(q,J=7.1Hz,2H),3.31-3.26(m,1H),3.18(dd ,J 1 =12.3Hz,J 2 =2.4Hz,1H),3.04(dd,J 1 =11.8Hz,J 2=9.1Hz, 1H), 1.39–1.32(m, 6H), 1.15(t, J=7.1Hz, 3H), 1.11(t, J=7.1Hz, 3H).

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Abstract

The invention belongs to the technical field of medicine, and relates to benzofuran acetamide compounds containing a propanolamine structure and their application, and also relates to their application as a beta receptor blocker. The compound, its stereoisomer, its prodrug and pharmaceutically active metabolite, and the pharmaceutically acceptable salt of the above compound are shown in formula I, wherein R is independently selected from C1-C6 alkyl ; 1 , R 2 independently selected from C1‑C4 alkyl, or R 1 , R 2 Together with the nitrogen atoms connected to them, a 5-6 membered heterocyclic group is formed, and the heterocyclic group contains 1-3 N, O or S heteroatoms. The invention also provides the use of the compound as a beta receptor blocker in the preparation of medicines for treating vascular smooth muscle spasm.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to benzofuran acetamide compounds containing propanolamine structure and their application, and also relates to their application as beta receptor blockers. Background technique: [0002] Hypertension is one of the cardiovascular diseases that threaten human health, and it is a frequently-occurring and chronic disease. It is an important cause of damage to important target organs such as the heart, brain, and kidneys. At present, there are about 200 million hypertensive patients in my country, and about 10 million hypertensive patients are newly added every year. Hypertension has become a major disease that threatens the health of Chinese residents, bringing heavy economic pressure and psychological burden to patients and their families. Hypertension can be divided into primary hypertension and secondary hypertension. The cause of the former is still unclear, while the latter is c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/83A61K31/5377A61K31/343A61K31/443A61K31/496A61K31/4025A61P9/12A61P9/04A61P9/06A61P9/10
CPCA61P9/04A61P9/06A61P9/10A61P9/12C07D307/83
Inventor 胡春李欣刘晓平关筱微王琳徐梅芹郝雅超张琴李慧玲陈程
Owner SHENYANG PHARMA UNIVERSITY