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

Quinolinone alkaloid compound and application thereof as antiviral drug

A technology of alkaloids and compounds, which can be used in antiviral agents, drug combinations, medical preparations containing active ingredients, etc., and can solve problems such as lack of vaccines

Active Publication Date: 2015-09-30
YANGZHOU BLUE BIOMEDICAL TECH CO LTD
View PDF3 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is currently no clinically applicable vaccine, and ribavirin (ribavirin) is the only chemotherapeutic drug used clinically (J.Med.Chem.2008,51,875–896)

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
  • Quinolinone alkaloid compound and application thereof as antiviral drug
  • Quinolinone alkaloid compound and application thereof as antiviral drug
  • Quinolinone alkaloid compound and application thereof as antiviral drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]

[0048] Weigh 500mg of compound 4, dissolve in 20mL acetone, add 150mg Na 2 CO 3 , after stirring at room temperature for half an hour, add 1.0mL MeI, react at 30°C for 4h, TLC detects that the reaction raw materials almost completely disappear, extract twice with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, concentrate, and pass through the silica gel column layer Analysis (eluent is EtOAc / petroleum ether=12:1~8:1) to obtain 472 mg of light yellow solid, which is compound 37, yield 92%, ESI-MS m / z: 565.3 [M+H] + , 587.3[M+Na] + .

Embodiment 2

[0050]

[0051] Weigh 10 mg of compound 4, dissolve in 2 mL of dichloromethane, add 3 μL of Ac 2 0, 50 μ L of pyridine, after stirring at room temperature for 2 h, TLC detected that the reaction raw materials almost completely disappeared, added 20 mL of dichloromethane to dilute, washed with water, and the organic phase was dried over anhydrous sodium sulfate, concentrated, and subjected to silica gel column chromatography (eluent: EtOAc / petroleum ether=12:1~10:1), to obtain 9.5 mg of a light yellow solid, which is compound 38, with a yield of 88.2%, ESI-MS m / z: 593.3 [M+H] + , 615.3[M+Na] + .

Embodiment 3

[0053]

[0054] Step (1): Weigh 400 mg of compound 37 and dissolve it in 15 mL of methanol, add a catalytic amount of CH 3 Adjust the pH to 9.0 to 10.0 with ONa, stir and react at room temperature for 2 hours, then add a cation exchange resin to adjust the pH to 7.0, remove the cation exchange resin by filtration, and concentrate to obtain 319 mg of a light yellow solid, which is compound 11, with a yield of 99.7%, ESI-MS m / z:474.2[M+Na] + .

[0055]

[0056] Step (2): Weigh Boc-L-valine (300mg, 1.38mmol) and dissolve it in dry toluene (10mL), add DCC (285mg, 1.38mmol), DMAP (7mg, 0.06mmol), and stir at room temperature After 5 minutes, compound 11 (27mg, 0.06mmol) was added, heated to 65°C and reacted for 48 hours, filtered, concentrated under reduced pressure, and subjected to silica gel column chromatography (petroleum ether / EtOAc=12 / 1) to obtain 35 mg of a light yellow solid , which is compound 30, the yield is 90%, ESI-MS (m / z): 651.3[M+H] + , 673.4[M+Na] + . ...

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 relates to a quinolinone alkaloid compound and an application thereof as an antiviral drug, and particularly relates to a compound of formula I-2 and the stereisomer, geometric isomer, solvate, pharmaceutically acceptable slat thereof or the solvate of the salt thereof and an application thereof as an antiviral agent. The quinolinone alkaloid compound provided by the invention has the characteristics of high efficiency and low toxicity as well as the potential that the quinolinone alkaloid compound is developed into an antiviral drug, and particularly can be used for preventing and / or treating the diseases caused by RSV infection.

Description

technical field [0001] The invention relates to a quinolinone alkaloid compound and a preparation method thereof, and also relates to the application of the quinolinone alkaloid compound in the preparation of antiviral drugs. In particular, it relates to a quinolinone alkaloid compound with strong inhibitory activity on respiratory syncytial virus (RSV) of Paramyxoviridae, its preparation method and application. Background technique [0002] Respiratory syncytial virus (respiratory syncytial virus pneumonia, referred to as syncytial virus, RSV, also belongs to Paramyxoviridae), is an RNA virus, which belongs to Paramyxoviridae. RSV infection can cause pneumonia and a variety of lower respiratory diseases. Every year, at least 3 million infants and young children worldwide are hospitalized due to RSV virus infection, and at least 160,000 of them die. Therefore, RSV is also known as a child killer (Science, 2013, 342, 546 -547). Currently there is no clinically applicable va...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/22C07D401/12A61K31/4704A61K31/4709A61P31/12A61P31/14A61P11/00
CPCC07D215/22C07D401/12
Inventor 陈敏于跃
Owner YANGZHOU BLUE BIOMEDICAL TECH CO LTD
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