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Cyclic formyl and cyclic ketone compounds as well as preparation method and pharmaceutical application thereof

A compound and pharmaceutical technology, applied in the field of cycloformyl and cyclic ketone compounds and their preparation, can solve the problems of no Zika virus vaccine, no Zika virus or anti-dengue virus drugs and the like

Active Publication Date: 2020-08-11
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Under the influence of many factors such as the deterioration of the global environment and warming, the epidemics of dengue fever and Zika have been expanding in recent years. However, there is currently only one dengue vaccine in a limited area. There is no Zika virus vaccine or other vaccines, and there is no effective anti-virus vaccine. Zika virus or anti-dengue virus drugs can be used in the clinical treatment of dengue fever disease, and now clinical treatment is mainly progressive supportive therapy (intensive supportive therapy), in which maintaining fluid balance is the main means

Method used

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  • Cyclic formyl and cyclic ketone compounds as well as preparation method and pharmaceutical application thereof
  • Cyclic formyl and cyclic ketone compounds as well as preparation method and pharmaceutical application thereof
  • Cyclic formyl and cyclic ketone compounds as well as preparation method and pharmaceutical application thereof

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Embodiment 1

[0035] Embodiment 1: the preparation method of compound of the present invention, comprises:

[0036]

[0037] Dissolve 2.74ml of phenylhydrazine and 7.0g of ZDL-5 in 500ml of DCM, add 5.3ml of 2,6-lutidine, and finally add 12.3g of TBTU, and stir overnight at room temperature. Purification yielded approximately 7 g of ZDL-17.

[0038]

[0039] Dissolve 600mg of benzohydrazide and 1.39g of ZDL-5 in 100ml of DCM, add 0.77ml of 2,6-lutidine, and finally add 2.12g of TBTU, and stir overnight at room temperature. Purification yielded approximately 1.6 g of ZDL-27.

[0040]

[0041] Dissolve ZDL-5 (500mg) in 50ml DCM, add CDI (323mg) under ice-cooling, stir for 20min, add dropwise hydrazine hydrate (0.55ml), and stir for 2h under ice-cooling.

[0042]

[0043] Dissolve 850mg of ZDL-26 in 100ml of DCM, add 0.74ml of pyridine under ice-cooling, and finally add 815mg of p-nitrobenzenesulfonyl chloride, and stir at room temperature for 6h. About 1.2 g of ZDL-29 was obtai...

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Abstract

The invention discloses cyclic formyl and cyclic ketone compounds as well as a preparation method and a pharmaceutical application thereof. The compound shown in (I) has a good function of inhibitinginfection and replication of Zika viruses and dengue viruses; the compounds can be used as medicines for treating and preventing diseases caused by Zika virus and dengue virus. The compound can be used as a medicine for treating and preventing diseases caused by other flaviviruses, such as yellow fever, west nile virus infection, encephalitis B caused by encephalitis B virus infection, chikungunyavirus infection, hepatitis C, forest encephalitis, AIDS caused by HIV, diseases caused by hand-foot-and-mouth virus infection and the like. The compound can be used for treating diseases caused by bacterial infection, including ulcerative colitis and Crohn's disease of inflammatory bowel disease, diseases caused by escherichia coli, diseases caused by staphylococcus aureus and the like, and diseases caused by acinetobacter baumannii.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to cycloformyl and cycloyl ketone compounds, their preparation method and pharmaceutical application. Background technique [0002] Zika virus (ZIKV), dengue virus (DENV), flavivirus (YFV), West Nile virus (WNV), Japanese encephalitis virus (JEV) of the family Flaviviridae and chikungunya of the alphavirus genus The viruses (CHIKV) are all arboviruses, and they are similar in many aspects of their life cycles. The main vector of these arboviruses, Aedesmosquito (including Aedes aegypti, Aedes albopictus and Aedes polynesiensis) is one of the largest mosquitoes in the world, living in All continents of the world except Antarctica. Symptoms of dengue fever-like illness generally appear 3-14 days after being bitten by an infectious Aedes mosquito (average 4-7 days). [0003] What is more special is that DENV has 4 serotypes. Although there is 65–70% similarit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D471/04C07D207/16C07D207/34C07D233/90C07D209/42C07D209/08C07D215/48C07D401/12A61K31/407A61K31/437A61K31/4188A61K31/40A61K31/404A61K31/4164A61K31/4402A61K31/47A61P31/04A61P31/14A61P31/18A61P9/00
CPCC07D487/04C07D471/04C07D207/16C07D207/34C07D233/90C07D209/42C07D209/08C07D215/48C07D401/12A61P31/04A61P31/14A61P31/18A61P9/00Y02A50/30C07D217/26C07D209/52C07D211/34C07D233/60C07F7/1804C07F5/025C07F5/022
Inventor 周国春徐斌李峰孙霞姜滨利代坤
Owner NANJING TECH UNIV
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