6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and application thereof

A compound and alkoxy technology, applied in the field of medicine, can solve the problems of different side effects of antihypertensive drugs, and achieve the effects of novel structure type, good development and application prospects, and good application value

Active Publication Date: 2018-03-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many kinds of these antihypertensive drugs, and different antihypertensive drugs are adapted to different symptoms, but all antihypertensive drugs have different side effects, and some even cause other complications

Method used

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  • 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and application thereof
  • 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and application thereof
  • 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and application thereof

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Experimental program
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Effect test

specific Embodiment approach

[0041] The preparation method of the compound of the invention is simple, the yield is stable, and the prepared compound can better prevent and treat hypertension.

[0042] The present invention is described in detail with the following examples. However, it should be understood that the present invention is not limited to the specific recited examples below.

Embodiment 1

[0043] Example 1: Preparation of 2-benzoyl-3-methyl-6-[2-hydroxyl-3-(isopropylamino)propoxy]benzofuran (T-01)

[0044] Step A: Preparation of 2'-Hydroxy-4'-Benzyloxyacetophenone

[0045] Put 2',4'-dihydroxyacetophenone (7.60g, 0.05mol), anhydrous potassium carbonate (8.00g, 0.06mol), potassium iodide (1.00g, 0.006mol), and 100mL acetone in a 250mL eggplant-shaped flask , stir well at room temperature. After diluting benzyl chloride (7.87g, 0.06mol) with 10mL of acetone, it was dropped into the reaction solution at a constant speed, and the dropwise addition was completed in about 10 minutes. The reaction was heated to reflux for 6 h, and the reaction was complete as monitored by TLC. After the reaction was completed, it was cooled to room temperature, and the organic solvent was distilled off under reduced pressure to obtain a light yellow solid. 50 mL of ethanol was recrystallized to obtain 10.45 g of white crystals with a yield of 86.4%. m.p: 101.6-103.4℃; EI-MS: 243.0 ([M...

Embodiment 2

[0054] Example 2: Preparation of 2-(4-methylbenzoyl)-3-methyl-6-[2-hydroxyl-3-(isopropylamino)propoxy]benzofuran (T-02)

[0055] Referring to the preparation method of Example 1, 1.01 g of light yellow solid was obtained with a yield of 65.6%. m.p: 100.0-101.5℃; EI-MS: 382.8 ([M+H] + ),404.2([M+Na] + ); IR: 3407.4, 3272.5, 2961.6, 2922.9, 2854.2, 1622.3, 1553.8, 1498.0, 1464.1, 1382.5, 1360.5, 1318.6, 1304.6, 1237.8, 1176.5, 1162.9, 1120.0; 1 H NMR (400MHz, CDCl 3 )δ7.98 (2H, d, J = 8.2Hz), 7.54 (1H, d, J = 8.6Hz), 7.31 (2H, d, J = 8.0Hz), 7.02 (1H, d, J = 2.0Hz) ,6.98(1H,dd,J 1 =8.7,J 2 =2.2Hz), 4.06(3H,dd,J 1 =11.2,J 2 =7.6Hz), 2.91(1H,dd,J 1 =12.1,J 2 =3.5Hz), 2.84 (1H,dt,J 1 =12.5,J 2 =6.3Hz), 2.77-2.70(1H,m), 2.59(3H,s), 2.45(3H,s), 1.10(6H,d,J=6.3Hz).

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Abstract

The invention belongs to the technical field of medicines and relates to a 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and an application thereof. The 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound comprises a stereoisomer and pharmacologically applicable salt of the compound and has the general structural formula shown in the description, wherein R is shown in the claims andspecification. The 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and the pharmacologically applicable salt-additive salt of the compound can be mixed with an existing medicine for use or used alone to be applied to a medicine for treating spastic diseases of vascular smooth muscle.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to 6-[2-hydroxy-3-(alkylamino)propoxy]benzofuran compounds and applications thereof. The compounds can be used as drugs for treating vascular smooth muscle spasm diseases. Background technique: [0002] Hypertension is one of the most important public health problems in the world today, but the awareness rate, treatment rate and control rate of hypertension diagnosis and treatment are all low. In the adult population of western developed countries, the incidence of hypertension is 30% to 40%, and it increases with age. In developing countries, the incidence of high blood pressure is higher. my country's epidemiological survey data recorded the prevalence of hypertension in the past 50 years, from 5% in 1959, 7% in 1979, 18.8% in 2008 to about 21% reported in recent years, the prevalence increased The number of patients has increased by about 4 times, reaching 200 million. At pres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80A61K31/343A61P9/04A61P9/08A61P9/10A61P9/12A61P13/12
CPCC07D307/80Y02P20/55
Inventor 胡春郭万欣王琳金丽萍周国军杨俊渠冰雪王海明
Owner SHENYANG PHARMA UNIVERSITY
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