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

4H-pyridino-[3,2-e][1,3]thiazine-4-ketone derivate and application thereof

A 2-e, derivative technology, applied in the field of medicine, can solve the problems of limited clinical application, obvious toxic and side effects, and poor curative effect of deep fungal infection

Active Publication Date: 2015-06-03
SHENYANG PHARMA UNIVERSITY
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Azole antifungal drugs are still the first choice. Although these antifungal drugs have certain curative effects, their clinical application is limited due to their obvious toxic and side effects and poor curative effect on deep fungal infections.

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
  • 4H-pyridino-[3,2-e][1,3]thiazine-4-ketone derivate and application thereof
  • 4H-pyridino-[3,2-e][1,3]thiazine-4-ketone derivate and application thereof
  • 4H-pyridino-[3,2-e][1,3]thiazine-4-ketone derivate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation of 2-benzylamino-4H-pyrido[3,2-e][1,3]thiazin-4-one

[0029] In a 100mL reaction flask, add 0.785g (5mmol) of 2-chloronicotinic acid and 10mL (0.141mol) of thionyl chloride, stir for 30min under ice-cooling, heat and reflux for 3h, and evaporate the remaining oxychloride under reduced pressure. Sulfone, the obtained light yellow solid is 2-chloronicotinyl chloride. Dissolve the solid in 10 mL of dry acetone, and slowly add an acetone solution of potassium thiocyanate (0.49 g of potassium thiocyanate in 10 mL of acetone) dropwise under cooling in an ice bath. The white potassium chloride solid produced by the reaction was filtered off to obtain an acetone solution of 2-chloronicotinoyl isothiocyanate, which was set aside. Take another 0.54g (5mmol) of benzylamine, dissolve it in 5mL of dry acetone, and add this solution dropwise to the acetone solution of 2-chloronicotinoyl isothiocyanate prepared above under stirring. React for 4 hours, concentr...

Embodiment 2

[0030] Example 2: Preparation of 2-phenylamino-4H-pyrido[3,2-e][1,3]thiazin-4-one

[0031] In a 100mL reaction flask, add 0.785g (5mmol) of 2-chloronicotinic acid and 10mL (0.141mol) of thionyl chloride, stir for 30min under ice-cooling, heat and reflux for 3h, and evaporate the remaining oxychloride under reduced pressure. Sulfone, the obtained light yellow solid is 2-chloronicotinyl chloride. Dissolve the solid in 10 mL of dry acetone, and slowly add an acetone solution of potassium thiocyanate (0.49 g of potassium thiocyanate in 10 mL of acetone) dropwise under cooling in an ice bath. The white potassium chloride solid produced by the reaction was filtered off to obtain an acetone solution of 2-chloronicotinoyl isothiocyanate, which was set aside. Take another 0.465g (5mmol) of benzylamine, dissolve it in 5mL of dry acetone, and add this solution dropwise to the acetone solution of 2-chloronicotinoyl isothiocyanate prepared above under stirring, after the addition is compl...

Embodiment 3

[0032] Example 3: Preparation of 2-(2-methylphenyl)amino-4H-pyrido[3,2-e][1,3]thiazin-4-one

[0033] In a 100mL reaction flask, add 0.785g (5mmol) of 2-chloronicotinic acid and 10mL (0.141mol) of thionyl chloride, stir for 30min under ice-cooling, heat and reflux for 3h, and evaporate the remaining oxychloride under reduced pressure. Sulfone, the obtained light yellow solid is 2-chloronicotinyl chloride. Dissolve the solid in 10 mL of dry acetone, and slowly add an acetone solution of potassium thiocyanate (0.49 g of potassium thiocyanate in 10 mL of acetone) dropwise under cooling in an ice bath. The white potassium chloride solid produced by the reaction was filtered off to obtain an acetone solution of 2-chloronicotinoyl isothiocyanate, which was set aside. Another 0.54g (5mmol) of 2-methylaniline was dissolved in 5mL of dry acetone, and the solution was added dropwise to the acetone solution of 2-chloronicotinoyl isothiocyanate prepared above while stirring, and After co...

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 technical field of medicines, discloses a novel 4H-pyridino-[3,2-e][1,3]thiazine-4-ketone derivate and an application thereof, and designs and synthesizes a series of novel-structure 4H-pyridino-[3,2-e][1,3]thiazine-4-ketone compounds and a medicine by taking the compounds or pharmaceutically acceptable solvates, optical isomers or polymorphic substances thereof as active ingredients. According to the novel 4H-pyridino-[3,2-e][1,3]thiazine-4-ketone derivate and the application thereof, the external antifungal activity of the derivate is tested by utilizing a double concentration dilution method, so that an initial structure-activity relationship is construction, and novel high-activity low-toxicity antifungal compounds capable of being applied to preclinical research are found; the compounds have a strong killing effect to clinically common disease-causing fungi, and are hopeful of overcoming defects of large toxic and side effects and easiness in generation of drug resistance of the existing clinically widely applied azole antifungal agent.

Description

technical field [0001] The invention relates to the technical field of medicine, specifically, it is a 4H-pyrido[3,2-e][1,3]thiazin-4-one derivative, salt or pharmaceutically acceptable antifungal activity Accepted solvates, optical isomers or polymorphs and their uses. Background technique [0002] Mycosis is a multiple, refractory disease. In recent years, due to the extensive use of drugs such as antibiotics, hormones, and immunosuppressants; the widespread use of large-scale operations such as catheters, intubations, and organ transplants, fungal infections, especially deep fungal infections, have become increasingly serious. Drugs for the treatment of fungal diseases are scarce. Azole antifungal drugs are still the first choice. Although these antifungal drugs have certain curative effects, their clinical application is limited due to their obvious toxic and side effects and poor curative effect on deep fungal infections. Therefore, it is still a challenging and inno...

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): C07D513/04A61K31/542A61P31/10A61P17/00
Inventor 郭春苏昕丛琳梁振田野李硕潘岩孙寰宇李婵韩雪崔巧平吕正敏
Owner SHENYANG PHARMA 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