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

Cyclic carbonate nucleoside compound and application thereof

A technology of compounds and nucleosides, applied in the field of medicine, can solve the problems of sows with greatly fluctuating morbidity, no treatment, and easy development of infectious peritonitis

Active Publication Date: 2022-05-06
广东晨康生物科技有限公司
View PDF6 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is estimated that 40~80% cats carry feline coronavirus (FCoV) in the whole world, and FcoV can be divided into two kinds of feline enteric coronavirus (FECV) and feline infectious peritonitis virus (FIPV), especially after FIPV infection, it is easy to develop into Infectious peritonitis (FIP), there is still no approved treatment for FIP, and the fatality rate is as high as 95%
Another example is the porcine epidemic diarrhea virus (PEDV) that causes acute intestinal infectious diseases in pigs, which also belongs to coronaviruses. The incidence rate of sows varies greatly, about 15-90%, and the mortality rate reaches more than 50%. treatment method

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
  • Cyclic carbonate nucleoside compound and application thereof
  • Cyclic carbonate nucleoside compound and application thereof
  • Cyclic carbonate nucleoside compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: the preparation of compound 1

[0058]

[0059] Take a dry 500.0 mL flask, dissolve GS-441524 (10.00 g, 34.33 mmol, 1.0 eq), imidazole (7.01 g, 103.00 mmol, 3.0 eq) in 50.0 mL of anhydrous DMF. Slowly add TBSCl (6.21g, 41.20 mmol, 1.2 eq) at 0°C, stir for 1 h, TLC (DCM : MeOH = 4:1) detects that the reaction of raw materials is complete, dilute with ethyl acetate (200 mL), wash with water (200 mL×2), washed with saturated brine (200 mL×1), collected the organic phase, added anhydrous sodium sulfate to dry, and distilled off the organic phase under reduced pressure to obtain a crude product, which was separated and purified by silica gel column chromatography (methanol:dichloro Methane=1:20) to obtain white solid compound C1 (methanol:dichloromethane=1:20, 12.53 g, 90%). 1 H NMR (400 MHz, CD 3 OD) δ 7.88 (s, 1H), 7.00 – 6.80 (m, 2H), 4.79 (d, J = 4.8 Hz, 1H), 4.30 –4.12 (m, 2H), 3.94 (dd, J = 11.6, 2.6 Hz, 1H), 3.82 (dd, J = 11.7, 3.3 Hz,1H), 3.3...

Embodiment 2

[0062] Embodiment 2: the preparation of compound 2

[0063]

[0064] Take a dry 100.0 mL flask, add compound 1 (1.20 g, 3.79 mmol, 1.0 eq), L-Boc-alanine (0.72 g, 3.79 mmol, 1.0 eq), DCC (0.78 g, 3.79 mmol, 1.0 eq ) and a catalytic amount of DMAP were dissolved in 20.0 mL of anhydrous DMF and reacted for 12 h. TLC (DCM:MeOH=10:1) detected that the reaction of raw materials was complete, diluted with ethyl acetate (60 mL), washed with water (20 mL×2), washed with saturated brine (20 mL×1), collected the organic phase, Add anhydrous sodium sulfate to dry, and then spin-dry under reduced pressure at 40°C. Silica gel column chromatography shows white solid C4 (DCM:MeOH = 100:3, 0.91 g, 49%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.96 (s, 1H), 7.07 (d, J = 4.6 Hz, 1H), 6.71 (d, J = 4.1 Hz, 1H), 5.37 – 5.29 (m, 1H), 5.05 (d, J = 6.9 Hz, 2H), 4.63 (q, J =4.8 Hz, 2H), 4.59 – 4.43 (m, 2H), 4.37 – 4.27 (m, 1H), 1.43 (s, 7H), 13 C NMR (101 MHz, CDCl 3 ) δ 176.46, 171.83, 155.38, 15...

Embodiment 3

[0066] Embodiment 3: the preparation of compound 3

[0067]

[0068] Take a dry 100.0 mL flask, add compound 1 (1.20 g, 3.79 mmol, 1.0 eq), Boc-valine (0.82 g, 3.79 mmol, 1.0 eq), DCC (0.78 g, 3.79 mmol, 1.0 eq) and A catalytic amount of DMAP was dissolved in 20.0 mL of anhydrous DMF and reacted for 12 h. TLC (DCM:MeOH=10:1) detected that the reaction of raw materials was complete, diluted with ethyl acetate (60 mL), washed with water (20 mL×2), washed with saturated brine (20 mL×1), collected the organic phase, Add anhydrous sodium sulfate for drying, and then spin-dry under reduced pressure at 40°C. Silica gel column chromatography shows white solid C5 (DCM:MeOH=100:3, 0.80 g, 42%). 1 H NMR (400 MHz, CDCl 3 ) δ = 8.02 (s, 1H), 7.07 (d, J =4.7, 1H), 6.78 (d, J =4.6, 1H), 6.34 (s, 2H), 5.98 (d, J =8.0, 1H), 5.33 (dd, J =5.2, 8.0, 1H), 5.05(d, J =9.1, 1H), 4.63 (q, J =5.1, 1H), 4.50 (qd, J =5.2, 12.0, 2H), 4.24 (dd, J =4.7, 8.9, 1H), 2.15 (m, 1H), 1.43 (d, J =2.6,...

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 cyclic carbonate nucleoside compound as shown in a formula (I), pharmaceutically acceptable salts, crystalline hydrates, solvates or tautomers of the cyclic carbonate nucleoside compound, and also discloses a pharmaceutical composition containing the cyclic carbonate nucleoside compound and application of the cyclic carbonate nucleoside compound. The compound and the pharmaceutical composition can be used for treating or preventing virus infection, such as infection of related viruses such as coronavirus, influenza virus, respiratory syncytial virus, flaviviridae virus, filoviridae virus, novel coronavirus and / or feline coronavirus. (I).

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a cyclic carbonate nucleoside compound and its application. Background technique [0002] At present, a variety of pathogenic viruses that are extremely harmful to humans have been found, such as influenza virus, respiratory syncytial virus (RSV), parainfluenza virus, atypical pneumonia (SARS) virus, Middle East respiratory syndrome (MERS) Virus, Ebola virus, new coronavirus (SARS-CoV-2), etc., especially new coronavirus, including Alpha, Beta, Gamma, Delta, Omicron and other mutant strains, only remdesivir and Molnupiravir (Mo Nupivir) and a few drugs such as Paxlovid are available, among which the curative effect of Monuprevir is relatively poor, and the effective rate for patients with mild to moderate new coronavirus pneumonia is only 30%, while the clinical efficacy of Remdesivir There are certain objections to the effectiveness. For example, in the comparative...

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): C07H19/067C07H9/02C07H11/04C07H13/04C07H13/12C07H1/00A61P31/12A61P31/14A61P31/16A61P31/18A61P31/22A61K31/706A61K31/7068
CPCC07H19/067C07H9/02C07H11/04C07H13/04C07H13/12C07H1/00A61P31/12A61P31/14A61P31/16A61P31/18A61P31/22
Inventor 李伟章郝玲花李朋辉周佩钰
Owner 广东晨康生物科技有限公司
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