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A group of benzene sulfonamido benzamide derivatives, and preparation and application thereof

A kind of technology of benzenesulfonamidobenzamide and derivatives, applied in the field of pharmacy

Inactive Publication Date: 2013-07-03
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

[0005] So far, there have been no relevant literature reports on the inhibition of ASBT activity by benzenesulfonylaminobenzamide derivatives. This research will have a good clinical application prospect

Method used

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  • A group of benzene sulfonamido benzamide derivatives, and preparation and application thereof
  • A group of benzene sulfonamido benzamide derivatives, and preparation and application thereof
  • A group of benzene sulfonamido benzamide derivatives, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (a) Preparation of 2-(3-nitrobenzenesulfonamido)methyl benzoate

[0024] Add methyl anthranilate (10g, 42.8mmol) and pyridine (3.4mL, 42.8mmol) into tetrahydrofuran (120mL), stir and react at 25°C for 0.5 hours, then add dropwise 3-nitrobenzenesulfonyl chloride (5.4mL , 42.8mmol), and the reaction solution was reacted at 25°C for 9 hours. The reaction liquid was evaporated under reduced pressure to remove tetrahydrofuran, and the residual liquid was poured into 100 mL of water, and a large amount of red solid was precipitated, and 5% hydrochloric acid was added dropwise until the pH value of the solution was 5, and after stirring for 0.5 hours, suction filtered, and the filter cake was washed with water to the filtrate It is neutral, and the filter cake is vacuum-dried to obtain 10.6 g of red powder solid, with a yield of 74%.

[0025] 1 H-NMR(400MHz,DMSO):3.75(3H,s),7.25(1H,t,J=6.0Hz),7.39(1H,d,J=6.0Hz),7.57(1H,t,J=6.0Hz ),7.79(1H,dd,J 1 =6.0Hz,J 2 =1.2Hz),7.85(1H...

Embodiment 2

[0033] (a) Preparation of N-(3-hydroxy-4-methoxyphenyl)-2-(3-nitrobenzenesulfonamido)benzamide

[0034] Prepared according to the method of Example 1 step (c), using the product of Example 1 step (b) and 3-hydroxyl-4-methoxyaniline to prepare N-(3-hydroxyl-4-methoxyphenyl )-2-(3-nitrobenzenesulfonamido)benzamide compound, in the form of off-white powder, with a yield of 65.1%.

[0035] 1 H-NMR(400MHz,DMSO):3.30(3H,s),7.01(1H,d,J=6.0Hz),7.23(1H,t,J=6.0Hz),7.35-7.40(3H,m),7.44 -7.47(1H,m),7.49-7.52(2H,m),8.03(1H,t,J=6.4Hz),8.45(1H,d,J=6.4Hz),8.67(1H,d,J=6.4Hz ),8.73(1H,s),10.24(1H,s).MS m / z:442.08[M-H] - .

Embodiment 3

[0037] (a) Preparation of N-(3,5-dichlorophenyl)-2-(3-nitrobenzenesulfonamido)benzamide

[0038] Prepared according to the method of step (c) of Example 1, using the product of step (b) of Example 1 and 3,5-dichloroaniline to prepare N-(3,5-dichlorophenyl)-2-(3 -Nitrobenzenesulfonamido) benzamide compound, in the form of off-white powder, with a yield of 72.3%.

[0039] 1H-NMR(400MHz,DMSO):7.30-7.36(3H,m),7.51(1H,t,J=8.0Hz),7.60(1H,d,J=7.2Hz),7.64(2H,d,J= 2.0Hz), 7.73(1H,t,J=8.0Hz),8.06(1H,d,J=8.4Hz),8.31-8.33(1H,m),8.40-8.41(1H,m),10.31(1H, s),10.45(1H,s).MS m / z:464.07[M-H] - .

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Abstract

The invention relates to a group of benzene sulfonamido benzamide derivatives, and a preparation method and an application thereof. The research results indicate that the compounds obviously inhibit the apical sodium-dependent bile acid transporter (ASBT) at the cellular level, thereby being expected to be researched and developed to become a clinically effective medicament for treating hyperlipemia and cholestatic diseases.

Description

Technical field: [0001] The invention belongs to the field of pharmacy, and specifically relates to a group of benzenesulfonamidobenzamide derivatives and their preparation and application in anti-hyperlipidemia and cholestasis. Background technique: [0002] Cardiovascular disease is listed as the first of the three major diseases (cardiovascular disease, tumor, infectious disease) that threaten human health today. Atherosclerosis is the pathological basis of cardiovascular diseases, and it is related to the occurrence and development of many diseases. The occurrence of atherosclerosis is closely related to the abnormality of serum cholesterol and low-density lipoprotein. The liver and gastrointestinal system are the main organs for cholesterol and lipoprotein metabolism, and the enterohepatic circulation of bile acids plays an extremely important role in the absorption and metabolism of cholesterol and lipids. [0003] At present, the clinically used lipid-lowering drugs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/21C07C303/40C07C311/29C07C311/46A61K31/18A61K31/63A61P3/06A61P1/16A61P9/00
Inventor 邵荣光王玉成刘洪涛何红伟蔡仕英白晓光王菊仙许乐幸徐长亮杨志衡
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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