5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives and application thereof

A technology of isopropylamino group and benzofuran, which is 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: 2018-04-20
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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  • 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives and application thereof
  • 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives and application thereof
  • 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation of 2-benzoyl-3-methyl-5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran (XLY-A39)

[0037] Step A: Preparation of 2'-Hydroxy-5'-Benzyloxyacetophenone

[0038] Put 2',5'-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 yellow crystals. 50 mL of ethanol was recrystallized to obtain 9.84 g of yellow crystals with a yield of 81.3%. m.p:60.5-63.2℃; EI-MS:243.0([M+H] +...

Embodiment 2

[0047] Example 2: Preparation of 2-(4-methylbenzoyl)-3-methyl-5-[2-hydroxyl-3-(isopropylamino)propoxy]benzofuran hydrochloride (XLY- 01)

[0048] 2-(4-methylbenzoyl)-3-methyl-5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran (XLY-A39) (0.50g, 1.31mmol ) was dissolved in 10mL of dichloromethane, and a sufficient amount of hydrogen chloride gas was passed into it. After all the salts were formed, the dichloromethane was distilled off under reduced pressure, and 3mL of ether was added to solidify and precipitate a yellow solid. Suction filtration, washing and filtration with a small amount of ethyl acetate The cake was dried to obtain 0.55 g of a yellow powdery solid, with a yield of 100%. m.p:152.5-154.0℃;IR:3342.9,3178.5,2977.0,2944.3,2784.1,2724.1,2459.3,2425.4,1628.7,1608.2,1548.2,1451.6,1431.2,1385.6,1364.2,1311.0,1287.7,1265.1,1235.8,1203.0,1184.9 , 1101.4.

Embodiment 3

[0049] Embodiment 3: Preparation of 2-(4-methylbenzoyl)-3-methyl-5-[2-hydroxyl-3-(isopropylamino)propoxy]benzofuran p-toluenesulfonate ( XLY-02)

[0050] Referring to the preparation method of Example 2, 0.60 g of white solid was obtained with a yield of 82.2%. m.p: 176.2.0-178.0℃; IR: 3334.9, 3026.9, 2921.1, 2856.4, 1642.3, 1607.4, 1566.2, 1467.1, 1452.8, 1377.1, 1328.6, 1294.5, 1236.0, 1214.5, 11103.1, 11027.6,

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Abstract

The invention belongs to the technical field of medicines, and relates to 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives and an application thereof. The 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives comprise stereoisomers and pharmaceutically acceptable salts of 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran, and the structural formula of the derivatives is shownin the description. The 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives and the pharmaceutically acceptable acid addition formed salts of 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran can be used together with existing medicines or individually, and are used for preparing medicines for treating blood vessel smooth muscle spasm diseases.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to 5-[2-hydroxy-3-(isopropylamino)propoxy]benzofuran derivatives 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. A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80A61K31/343A61P9/12A61P25/00A61P9/04A61P13/12
CPCC07D307/80Y02P20/55
Inventor 胡春王琳邢丽妍黄二芳郭万欣付守廷张宝成张超
Owner SHENYANG PHARMA UNIVERSITY
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