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Amide compound and preparation method, medicinal composition and application thereof

A technology of amide compounds and drugs, which is applied in the field of amide compounds and can solve the problems of poor effect and large side effects of blood lipid-lowering drugs

Active Publication Date: 2015-01-21
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is to provide an amide compound, its preparation method, pharmaceutical composition and application in order to overcome the defects of poor effect of existing blood lipid-lowering drugs and large side effects after long-term use.

Method used

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  • Amide compound and preparation method, medicinal composition and application thereof
  • Amide compound and preparation method, medicinal composition and application thereof
  • Amide compound and preparation method, medicinal composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0177] Example 1: Preparation of amide compound 1-1

[0178] 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionyl chloride 1g, 2-aminoacetophenone 0.4g, triethylamine 0.3g, dichloromethane 60mL placed in 100mL In a single-neck flask, react for 4 hours at room temperature, evaporate the solvent, and obtain the target amide compound 1-11.09g by column chromatography with a yield of 84%. MS (ESI): 436[M+H + ].

[0179] The amide compound 1-2 and the amide compound 1-3 can be prepared by a method similar to that described in Example 1 using corresponding raw materials. Amide compound 1-2: MS (ESI): 368[M+H + ]. Amide compounds 1-3: MS (ESI): 479[M+H + ].

Embodiment 2

[0180] Example 2: Preparation of amide compound 1-1

[0181] 2-methyl-2-(4-(4-chlorobenzoyl)phenoxy)propionic acid 1g, dicyclohexylcarbodiimide 0.57g, 2-aminoacetophenone 0.33g, dichloromethane 60mL Placed in a 100mL single-necked flask, reacted at room temperature for 4 hours, evaporated the solvent, and column chromatography gave the target amide compound 1-11.12g with a yield of 82%.

Embodiment 3

[0182] Example 3: Preparation of amide compounds 1-4

[0183] 5-(2,5-dimethylphenoxy)-2,2-dimethylvaleryl chloride 1g, 2-amino-(4-bromophenyl)-ethanone 0.79g, triethylamine 0.38g, Put 60 mL of dichloromethane in a 100 mL single-necked flask, react for 4 hours at room temperature, evaporate the solvent, and obtain 1-41.35 g of the target amide compound by column chromatography with a yield of 81%. MS (ESI): 446[M+H + ].

[0184] Amide compounds 1-5 to amide compounds 1-16 can be prepared by using the similar method described in Example 3 with corresponding raw materials.

[0185] Amide compounds 1-5: Yield 83%, MS (ESI): 386[M+H + ].

[0186] Amide compound 1-6: yield 87%, MS (ESI): 514[M+H + ].

[0187] Amide compounds 1-7: Yield 79%, MS (ESI): 402[M+H + ].

[0188] Amide compounds 1-8: Yield 76%, MS (ESI): 470[M+H + ].

[0189] Amide compounds 1-9: Yield 82%, MS (ESI): 454[M+H + ].

[0190] Amide compounds 1-10: 85% yield, MS (ESI): 557[M+H + ].

[0191] Amide compounds 1-11: Yield 77%, ...

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Abstract

The invention discloses an amide compound and a preparation method, a medicinal composition and an application thereof. The invention provides an amide compound which is shown as a formula I, and a pharmaceutically-acceptable salt, a metabolite, a metabolism precursor or a prodrug thereof. The amide compound has the effects of reducing cholesterol and low density lipoprotein in blood, and also has the effects of promoting biliary excretion, lowering the content of cholesterol in bile, increasing the content of bile acid, and preventing and treating cholelithiasis.

Description

Technical field [0001] The invention relates to amide compounds, preparation methods, pharmaceutical compositions and applications thereof. Background technique [0002] Cardiovascular and cerebrovascular diseases are currently the most serious diseases endangering human life and health, and are common and frequently-occurring diseases of middle-aged and elderly people. It ranks first in morbidity and mortality in many countries. Atherosclerosis is the basis of many cardiovascular and cerebrovascular diseases. A large number of experiments and clinical data have proved that atherosclerosis is closely related to abnormal lipid metabolism. Therefore, blood lipid regulating drugs have become an important area of ​​current new drug research. [0003] Through prospective, random and controlled clinical studies, it has been proven that some statins can reduce the incidence of atherosclerosis and coronary heart disease, reduce the mortality rate caused by coronary heart disease, and red...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C235/06A61K31/192A61K31/165A61K31/166A61K31/235A61P3/06A61P1/16
Inventor 于振鹏张瑱王国平肖璘刘珉宇潘绵立刘全海
Owner SHANGHAI INST OF PHARMA IND CO LTD
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