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

Polycyclic benzodifuran compound and application thereof as anti-RSV drug

A polycyclic benzobisfuran compound technology, applied in the field of polycyclic benzobisfuran compounds, can solve the problems of teratogenicity, unsatisfactory application effect of anti-RSV drugs, general curative effect, etc.

Active Publication Date: 2020-12-25
JINAN UNIVERSITY
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, ribavirin can be used for the treatment of severe RSV infection, but there are side effects such as teratogenicity, and the curative effect is average.
Palivizumab is a monoclonal antibody that can be used to prevent RSV infection in high-risk children with chronic lung disease and congenital heart disease, as well as premature infants, but it cannot be used for the treatment of patients who have been infected with RSV and is expensive
Due to the unsatisfactory application effect of anti-RSV drugs currently used clinically, it is urgent to develop new anti-RSV drugs to prevent or treat RSV infection.

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
  • Polycyclic benzodifuran compound and application thereof as anti-RSV drug
  • Polycyclic benzodifuran compound and application thereof as anti-RSV drug
  • Polycyclic benzodifuran compound and application thereof as anti-RSV drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of compound 7~12

[0042]

[0043] first step:

[0044] Dissolve phloroglucinol 5 in nitromethane solution at room temperature, add anhydrous aluminum trichloride and isovaleryl chloride successively, and raise the temperature to 40 ºC. After reacting for 5 hours, the reaction solution was slowly poured into ice water, and saturated potassium sodium tartrate solution was added, followed by vigorous stirring. The reaction solution was extracted 3 times with ethyl acetate. The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The resulting crude product was separated and purified by silica gel column chromatography to obtain compound 7 (90% yield)

[0045] Step two:

[0046] Compound 7 was dissolved in MeOH solution at room temperature, and NaOMe in MeOH solution was added. After reacting a...

Embodiment 2

[0055] Embodiment 2: the preparation of compound 15 and 16

[0056]

[0057] first step:

[0058] Dissolve phloroglucinol 5 in nitromethane solution at room temperature, add anhydrous aluminum trichloride and p-fluorophenylacetyl chloride 13 successively, and raise the temperature to 40 ºC. After reacting for 5 hours, the reaction solution was slowly poured into ice water, and saturated potassium sodium tartrate solution was added, followed by vigorous stirring. The reaction solution was extracted 3 times with ethyl acetate. The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 14 (yield 80%).

[0059] Step two:

[0060] At room temperature, compounds 10 and 14 were dissolved in toluene, then trifluoroacetic acid and m...

Embodiment 3

[0063] Embodiment 3: the preparation of compound 19 and 20

[0064]

[0065] first step:

[0066] Dissolve phloroglucinol 5 in nitromethane solution at room temperature, add anhydrous aluminum trichloride and cyclohexanecarbonyl chloride 17 successively, and raise the temperature to 40 ºC. After reacting for 5 hours, the reaction solution was slowly poured into ice water, and saturated potassium sodium tartrate solution was added, followed by vigorous stirring. The reaction solution was extracted 3 times with ethyl acetate. The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The resulting crude product was separated and purified by silica gel column chromatography to obtain compound 18 (yield 75%).

[0067] Step two:

[0068] At room temperature, compounds 10 and 18 were dissolved in toluene, then trifluoroacetic acid and m...

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 polycyclic benzodifuran compound with a formula (I), a preparation method thereof and an application of the polycyclic benzodifuran compound as an anti-respiratory syncytialvirus (RSV) drug. The polycyclic benzodifuran compound disclosed by the invention has a relatively strong inhibiting effect on respiratory syncytial virus, and the activity of the polycyclic benzodifuran compound is superior to that of the existing commercially available drug ribavirin. Therefore, the compound has a good application prospect in treating related diseases caused by respiratory syncytial virus infection.

Description

technical field [0001] The invention relates to a class of polycyclic benzobisfuran compound, its preparation method and its application in antiviral medicine. More specifically, the present invention relates to the application of a class of polycyclic benzobisfuran compounds as anti-respiratory syncytial virus (respiratory syncytial virus, RSV) drugs. Background technique [0002] Respiratory syncytial virus (RSV) is a single-stranded negative-sense RNA enveloped virus belonging to the family Paramyxoviridae and the genus Pneumovirus. It can be divided into two subtypes, A and B, according to the antigenic characteristics of the virus surface. RSV can be transmitted through the respiratory tract and is one of the most common viral pathogens causing lower respiratory tract disease in infants, the elderly, and immunocompromised adults. Especially in infants and young children, it can cause severe lower respiratory tract diseases such as bronchitis and pneumonia. [0003] So...

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): C07D493/22A61K31/343A61P11/00A61P31/14
CPCC07D493/22A61P11/00A61P31/14C07B2200/07
Inventor 叶文才王英胡利军邓路铭唐维李药兰
Owner JINAN UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com