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2-acylamino-3-alkoxyl substituted pyridine compounds and novel use thereof

A technology of alkoxy group and amide group, which is applied in the pharmaceutical field and achieves broad application prospects and good anti-atherosclerosis effect.

Active Publication Date: 2014-12-24
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2-amido-3-alkoxy substituted pyridine compounds have no literature reports on the anti-atherosclerosis effect, which is the first discovery of this patent application

Method used

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  • 2-acylamino-3-alkoxyl substituted pyridine compounds and novel use thereof
  • 2-acylamino-3-alkoxyl substituted pyridine compounds and novel use thereof
  • 2-acylamino-3-alkoxyl substituted pyridine compounds and novel use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] The preparation of embodiment 1N-(3-hydroxyl-2-pyridyl)-4-(1,3-dithio-2-cyclopentyl)benzamide (LX-1)

[0046] According to the operating method of Example 1, with 0.23g (0.001mol) 4-(1,3-dithio-2-cyclopentyl) benzoic acid and 0.11g (0.001mol) 2-amino-3-pyridinol Feed, to obtain LX-1 pure product 0.31g white solid, yield 97%. MS (ESI, m / z): 319[M]+, 1H NMR (500MHz, d6-DMSO) δ (ppm): 10.568 (s, 1H, NH-CO), 9.856 (s, 1H, -OH), 7.977(m, 2H, Ph-H), 7.655(m, 2H, Ph-H), 7.341(dd, 1H, J=8.0Hz, 1.5Hz, Py-6H), 7.224(dd, 1H, J=8.0 Hz, 5.0Hz, Py-4H), 5.843(s, 1H, SCHS), 5.337(t, 1H, J=5.0Hz, Py-5H), 3.57(m, 2H, CH2), 3.396(m, 2H, CH2)

Embodiment 2

[0047] The preparation of embodiment 2N-(3-hydroxyl-2-pyridyl)-4-trifluoromethoxybenzamide (LX-3)

[0048] According to the operating method of Example 1, 0.21g (0.001mol) 4-trifluoromethoxybenzoic acid and 0.11g (0.001mol) 2-amino-3-pyridinol were fed to obtain 0.25g of LX-3 pure product yellow Solid, 84% yield. MS (ESI, m / z): 299[M]+, 1H NMR (500MHz, d6-DMSO) δ (ppm): 8.151 (m, 1H, Ph-H), 7.960 (d, 1H, J=5.0Hz , Py-6H), 7.530(m, 1H, Ph-H), 7.326(d, 1H, J=7.5Hz, Py-4H), 7.203(m, 1H, NH-CO), 6.654(s, 1H, -OH), 5.337(t, 1H, J=5.0Hz, Py-5H),

Embodiment 3

[0049] The preparation of embodiment 3N-(3-hydroxyl-2-pyridyl)-4-iodobenzamide (LX-5)

[0050] According to the operation method of Example 1, feed intake with 0.25g (0.001mol) 4-iodobenzoic acid and 0.11g (0.001mol) 2-amino-3-pyridinol, obtain LX-5 pure product 0.36g white solid, the yield 90%. MS (ESI, m / z): 341[M]+, 1H NMR (500MHz, d6-DMSO) δ (ppm): 7.957 (s, 1H, NH), 7.924 (m, 2H, Ph-2H), 7.650 (s, 1H, Py-6), 7.323 (m, 2H, Ph-2H), 7.199 (s, 1H, OH), 5.337 (m, 2H, Py-4, 5H),

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Abstract

The invention discloses 2-acylamino-3-alkoxyl substituted pyridine compounds and an application of the compounds in treatment and / or prevention of atherosclerosis-induced cardiovascular diseases. Experiments verify that the compounds or pharmaceutical compositions have the function of up-regulating or stabilizing ABCA1 and SR-BI / CLA-1 and can be used for inhibiting bubblization of macrophage or enhancing cholesterol efflux of macrophage. Experiments show that the compounds have the effects of reducing blood fat and cholesterol and have an application prospect of becoming a medicine for reducing blood fat, treating atherosclerosis, cardiovascular diseases and the like.

Description

technical field [0001] The present invention relates to a class of 2-amido-3-alkoxypyridine compounds, which are used in the treatment and / or prevention of atherosclerotic cardiovascular diseases and belong to the field of pharmacy; , SR-BI / CLA-1, the application of lipid-lowering and cholesterol-lowering drugs; the present invention also relates to the preparation method of the compound; the present invention also relates to the pharmaceutical composition of the compound. Background technique [0002] Cardiovascular disease is the main killer of human health in developed countries and most developing countries. In recent years, with the improvement of people's material living standards, the incidence of cardiovascular and cerebrovascular diseases has shown an obvious upward trend, and the death rate of cardiovascular and cerebrovascular diseases accounts for the The composition of population death has reached 1 / 3. Atherosclerosis is the pathological basis of many serious c...

Claims

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Application Information

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IPC IPC(8): A61K31/4439A61K31/4412A61K31/443A61K31/496A61K31/4545C07D409/12C07D213/75C07D403/12C07D405/12C07D417/14A61P9/00A61P3/06A61P9/10
Inventor 司书毅洪斌许艳妮贾晓健李永臻刘畅王丽刘祺
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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