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

Preparation method and medical application of 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt

A tert-butyl, -6H-1 technology, applied in the direction of effective components of heterocyclic compounds, antiviral agents, organic chemistry, etc., can solve the problems of effectiveness impact, helplessness of influenza virus strains, lack of understanding, etc., and achieve low cost Effect

Inactive Publication Date: 2009-11-04
HUNAN UNIV
View PDF1 Cites 16 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On April 25, Margaret Chan, Director-General of the WHO, declared the outbreak a "public health emergency of international concern" due to a lack of understanding of the clinical, epidemiological and virological reports of the cases
[0010] Influenza vaccine is the most effective measure to prevent influenza, but due to the high variability of influenza virus antigens, the effectiveness of conventional influenza vaccines in preventing influenza outbreaks and epidemics is seriously affected, and they are helpless against new unforeseen influenza virus strains

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
  • Preparation method and medical application of 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt
  • Preparation method and medical application of 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt
  • Preparation method and medical application of 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 4-tert-butyl-6-(4-chlorophenyl)-2-amino-6H-1,3-thiazine hydrochloride (I a ) preparation

[0030]

[0031] 0.010mol 1-(4-chlorophenyl)-4,4-dimethylpenten-3-one and 0.012mol thiourea, 20mL ethanol, 0.011mol hydrochloric acid were stirred and refluxed, the reaction was detected by TLC, and the reaction was completed for 5 hours. Washed with water, dried to obtain 4-tert-butyl-6-(4-chlorophenyl)-2-amino-6H-1,3-thiazine hydrochloride (I a ). Yield 87.0%, mp 228-230°C. 1 H NMR (400MHz, CDCl 3 )δ: 1.23(s, 9H, 3×CH 3 ), 5.05 (d, J=6.0Hz, 1H, thiazine ring 5-H), 5.17 (d, J=6.0Hz, 1H, thiazine ring 6-H), 7.26 (d, J=6.0Hz, 2H , benzene ring 2, 6-H), 7.35 (d, J=6.8Hz, 2H, benzene ring 3, 5-H), 9.74, 9.99 (2×s, 2H, NH 2 ), 11.3(s, 1H, N + h).

Embodiment 2

[0032] Example 2 4-tert-butyl-6-(2-chlorophenyl)-2-amino-6H-1,3-thiazine hydrochloride (I b ) preparation

[0033]

[0034] 0.010mol 1-(2-chlorophenyl)-4,4-dimethylpenten-3-one and 0.012mol thiourea, 20mL ethanol, 0.011mol hydrochloric acid reacted at 30°C, TLC detected the reaction, reacted for 3h, and reacted Complete, wash with water, dry to get 4-tert-butyl-6-(2-chlorophenyl)-2-amino-6H-1,3-thiazine hydrochloride (I b ), yield 65.0%, mp 149~150°C. 1 H NMR (400MHz, CDCl 3 )δ: 1.33(s, 9H, 3×CH 3 ), 5.19 (d, J=5.6Hz, 1H, thiazine ring 5-H), 5.36 (d, J=6.0Hz, 1H, thiazine ring 6-H), 7.27~7.43 (m, 4H, benzene ring H), 9.03, 10.23 (2×s, 2H, NH 2 ), 11.59 (s, 1H, N + h).

Embodiment 3

[0035] Example 3 4-tert-butyl-6-(2,4-dichlorophenyl)-2-amino-6H-1,3-thiazine hydrochloride (I c ) preparation

[0036]

[0037] 0.010mol 1-(2,4-dichlorophenyl)-4,4-dimethylpenten-3-one and 0.012mol thiourea, 20mL methanol, 0.011mol hydrochloric acid reflux, TLC detection reaction, reaction 6h, reaction Finished, washed with water, dried to obtain 4-tert-butyl-6-(2,4-dichlorophenyl)-2-amino-6H-1,3-thiazine hydrochloride (I c ), yield 52.1%, mp 105°C. 1 H NMR (400MHz, CDCl 3 )δ: 1.32(s, 9H, 3×CH 3 ), 5.17 (d, J=5.2Hz, 1H, thiazine ring 5-H), 5.30 (d, J=4.4Hz, 1H, thiazine ring 6-H), 7.20~7.44 (m, 3H, benzene ring H), 9.28, 10.20 (2×s, 2H, NH 2 ), 11.54(s, 1H, N + h).

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 preparation method and medical application of 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt. The preparation method of the 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt comprises the steps of: stirring 0.010 mol of 1-phenyl-4,4-dimethyl pentene-3-ketone, 0.012 mol of thiourea and 0.011 mol of acid in an organic solvent at a temperature of between 30 and 80 DEG C, performing TLC detection on reaction process, completing reaction, filtering, washing and drying the obtained product and obtaining the 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt (I). The 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt (I) can be medically used for preparing influenza virus neuraminidase inhibitors. In a formula, HX is hydrochloric acid, phosphoric acid, hydrobromic acid, sulphuric acid, trifluoroacetic acid or methanesulfonic acid, and Y is Cl, Br, CH3, Et, CF3, OCH3 or OEt.

Description

technical field [0001] The present invention relates to the preparation method and medical use of a class of compounds, specifically the preparation method of 4-tert-butyl-6-phenyl-2-amino-6H-1,3-thiazine salt; 4-tert-butyl-6 -Phenyl-2-amino-6H-1,3-thiazine salt can be used in medicine to prepare influenza virus neuraminidase inhibitors. Background technique [0002] There are two glycoproteins on the surface of influenza virus: hemagglutinin (HA) and neuraminidase (NA). Because NA is relatively conservative in the mutation process of influenza virus, it becomes a very good target for designing and synthesizing anti-influenza drugs. NA is a mushroom cloud-shaped envelope glycoprotein, composed of 453-466 amino acids, its structure is divided into head and neck, the head contains enzymes, has antigenicity, and the neck has a hydrophobic region, making it easy to insert into the double layer in the lipid membrane. NA catalyzes the cleavage of N-acetylaminoneuraminidase at t...

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): C07D279/06A61K31/54A61P31/16
Inventor 胡艾希夏林
Owner HUNAN UNIV
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