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

Acyl neuraminidase inhibitor and medical application thereof

An acetamido, pharmaceutical technology, applied in the preparation of carboxylic acid amides, antiviral agents, preparation of organic compounds, etc., can solve the problems of central nervous system toxic and side reactions, easy to produce drug resistance and other problems

Pending Publication Date: 2017-05-31
SHENYANG PHARMA UNIVERSITY
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are mainly two types of anti-influenza virus drugs, matrix protein M2 inhibitors and neuraminidase inhibitors. Matrix protein M2 inhibitors are mainly amantadine drugs, which can penetrate the blood-brain barrier. Has central nervous system toxicity and is prone to drug resistance

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
  • Acyl neuraminidase inhibitor and medical application thereof
  • Acyl neuraminidase inhibitor and medical application thereof
  • Acyl neuraminidase inhibitor and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (3R,4R,5S)-4-Acetamido-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester (Ⅱ-1)

[0033] Add 130mg (0.417mmol) oseltamivir, 238mg HATU (0.625mmol), 182μL DIPEA (1.04mmol), 30mg glacial acetic acid (0.50mmol) to the 50mL round bottom flask, stir the reaction at room temperature, after the reaction, organic phase It was washed with 1N HCl solution, saturated sodium carbonate solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to obtain 110 mg of solid with a yield of 74.5%.

Embodiment 2

[0035] (3R,4R,5S)-4-Acetamido-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid (Ⅰ-1)

[0036] Get the previous step product (3R, 4R, 5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester (Ⅱ-1 )

[0037] 110mg (0.31mmol), add methanol 10mL and 0.78mL 1N sodium hydroxide aqueous solution, add 1.22mL deionized water, make V (methanol): V (water) = 5: 1, stir the reaction at room temperature, after the end of the reaction, reduce Methanol was removed by pressure steaming, and the pH was adjusted to 1-2. The precipitate was precipitated, filtered, and dried to obtain 80 mg of white solid with a yield of 82.6%. 1 H NMR (400MHz, DMSO) δ12.56(s, 1H), 7.77(d, J=9.2Hz, 1H), 7.66(d, J=8.9Hz, 1H), 6.60(s, 0H), 4.07(d ,J=8.3Hz,1H),3.88(m,1H),3.78–3.66(m,1H),3.42–3.35(m,1H),2.49–2.41(m,1H),2.19-2.11(m,0H ),1.77(s,3H),1.76(s,3H),1.47-1.33(m,4H),0.83(t,J=7.4Hz,3H),0.76(t,J=7.4Hz,3H); MS (ESI):349.2[M+Na] + ,325.0[M-H] - .

Embodiment 3

[0039] (3R,4R,5S)-4-Acetamido-5-trifluoroacetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester (Ⅱ-2)

[0040] The operation is the same as in Example 1, with oseltamivir and trifluoroacetic acid as the reaction raw materials. 43mg of white solid was obtained, the yield was 18%.

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 the field of medicinal chemistry, in particular to an oseltamivir primary amine acylated derivative, as well as a preparation method and medical application of the oseltamivir primary amine acylated derivative. The oseltamivir primary amine acylated derivative is mainly medically applied to a series of infectious diseases caused by influenza viruses. Particularly, the invention provides a derivative as shown in the general formula (I), as well as pharmaceutically acceptable salt and an isomer of the derivative. R1 and R2 are as described in claims and the specification.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of acylated derivatives of oseltaz-weberamide, its preparation method and its medical application. The medical application is mainly used for treating a series of infectious diseases caused by influenza virus. Background technique [0002] Influenza (abbreviated as influenza) is an acute respiratory infection caused by influenza virus, and can also cause influenza virus pneumonia and secondary bacterial pneumonia. The elderly and those with various chronic diseases or weak constitutions are prone to severe complications and higher mortality rates after suffering from influenza, which is likely to cause a pandemic. There have been three influenza outbreaks in history, which have dealt heavy blows to mankind again and again, namely the Spanish flu in 1918, the Asian flu in 1957 and the Hong Kong flu in 1968. Today, influenza is still a disease that threatens human health...

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): C07C233/52C07C231/02A61K31/196A61P31/16
CPCC07C233/52C07B2200/07
Inventor 田永寿王矿磊
Owner SHENYANG PHARMA UNIVERSITY
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