Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

[N-(3',4'methylenedioxy)phenylethyl] formamidobenzoic acid derivative, its preparation method and uses

A technology of methylenedioxy and phenylethyl, applied in the application field of liver protection drugs, can solve the problems of many side effects, high price and low efficiency

Active Publication Date: 2007-04-25
北京协和制药二厂有限公司
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Interferon has a certain effect on anti-virus, but its efficiency is not high, there are many side effects, and it is expensive, so very few patients can persist in using it for a long time; Need further verification

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • [N-(3',4'methylenedioxy)phenylethyl] formamidobenzoic acid derivative, its preparation method and uses
  • [N-(3',4'methylenedioxy)phenylethyl] formamidobenzoic acid derivative, its preparation method and uses
  • [N-(3',4'methylenedioxy)phenylethyl] formamidobenzoic acid derivative, its preparation method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Sodium 2-[N-(3',4'methylenedioxy)phenylethyl]formamidobenzoate

[0083]

[0084]Dissolve 20.02g of phthalic anhydride in 120mL of acetone, add 22.3g of (3', 4'methylenedioxy)phenethylamine dropwise under stirring at room temperature, drop it in 10 minutes, continue to stir for 2 hours, and the precipitate gradually precipitates out , filtered, and the resulting white solid was recrystallized in 95% ethanol (w / v: 2 g / mL). 38.0 g of 2-[N-(3',4'methylenedioxy)phenylethyl]formamidobenzoic acid was obtained as white needle crystals. m.p.142-143℃

[0085] 1 HNMR (300MHz, CD 3 OD, δppm): 2.76(t, 2H, J=6.9Hz, H-9), 3.45(t, 2H, J=6.9Hz, H-8), 5.83(s, 2H, H-7'), 6.7 -7.9 (m, 7H, Ar-H)

[0086] Elemental analysis: theoretical value: C65.17%, H4.79%, N4.47%; measured value: C65.23%, H4.69%, N4.60%

[0087] IR (KBr, cm -1 ): 3307, 3300-2500 (br.), 1730, 1628, 1600, 1577, 1500, 1489, 1300, 1248, 1039, 937, 924, 876, 766, 700

[0088] Dissolve 939 mg of 2-[N-(3',4'methylene...

Embodiment 2

[0090] 3-Nitro-2-[N-(3’,4’methylenedioxy)phenylethyl]formamidobenzoic acid

[0091]

[0092] Dissolve 0.989g of 3-nitrophthalic anhydride in acetone, add dropwise 0.99ml of (3',4'methylenedioxy)phenethylamine under stirring at room temperature, drop it in 10 minutes, and continue stirring for 2 hours. The precipitate gradually separated out and was filtered, and the obtained white solid was recrystallized in 95% ethanol. 1.35 g of the desired compound was obtained as a pale yellow solid. m.p.168-169℃

[0093] 1 HNMR (300MHz, CD 3 OD, δppm): 2.82(t, 2H, J=7.2Hz, H-9), 3.50(t, 2H, J=7.2Hz, H-8), 5.98(s, 2H, H-7'), 6.74 (m+s, 3H, H-5', H-6', H-2'), 7.73-8.29 (m, 3H, H-4, H-5, H-6). ESIMS: 359(M+1)

Embodiment 3

[0095] 6-Methyl-2-[N-(3',4'methylenedioxy)phenylethyl]formamidobenzoic acid

[0096]

[0097] Method is with embodiment 2. 0.908 g of 3-methylphthalic anhydride was used instead of 3-nitrophthalic anhydride. Diethyl ether was used instead of acetone, and the obtained white solid was recrystallized in 80% ethanol (w / v: 2 g / ml) after filtration. 1.3 g of the desired compound was obtained as white needle crystals. m.p.113-115℃

[0098] 1 HNMR (300MHz, CD 3 OD, ppm): 2..19(s, 3H, CH 3 -6), 2.82(t, 2H, J=7.5Hz, H-9), 3.48(t, 2H, J=7.5Hz, H-8), 5.83(s, 2H, H-7'), 6.70 (m+s, 3H, H-5', H-6', H-2'), 7.24-7.80(m, 3H, H-3, H-4, H-5)

[0099] ESIMS: 328(M+1)

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a compound (I) or stereomer or drug salt, wherein each group is defined in the introduction, which can be applied in the hepatitis drug.

Description

technical field [0001] The invention relates to 2-[N-(3',4'methylenedioxy)phenylethyl]formamidobenzoic acid derivatives, their stereoisomers and pharmaceutically acceptable salts thereof, their preparation methods and Their use as medicines, especially as hepatoprotective medicines. Background technique [0002] Liver disease, especially hepatitis, is one of the most common and important infectious diseases worldwide. There are about 350 million people in the world suffering from hepatitis B, and 2 million patients die from hepatitis B every year, ranking the 9th among the causes of death in the world. The incidence of viral hepatitis in my country ranks first in the world, about 80% of hepatitis patients are concentrated in China, and nearly 500,000 people die of hepatitis-related diseases every year. For a long time, the treatment of hepatitis has always been a major problem in the world's medical circles. [0003] There are more than 700 kinds of Chinese and Western me...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D317/28A61K31/36A61P1/16A61P31/14A61P31/20
Inventor 张猛尹大力赵立敏王珂
Owner 北京协和制药二厂有限公司
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com