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

4-Hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents

A compound and alkyl technology, which can be applied to antiviral agents, compounds of group 4/14 elements of the periodic table, phosphorus organic compounds, etc., can solve the problems of no references, etc.

Inactive Publication Date: 2001-01-24
PHARMACIA & UPJOHN CO
View PDF36 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Formula 32 is listed in the CAS registration file, but there is no corresponding reference

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
  • 4-Hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents
  • 4-Hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents
  • 4-Hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0180] Figures A-V The preparation of compounds of the invention is described. All starting materials were prepared by methods described in these figures or by methods analogous thereto, which are well known to those of ordinary skill in the art of organic chemistry. All final compounds of the invention are prepared by methods described in these figures or by methods analogous thereto, which are well known to those of ordinary skill in the art of organic chemistry. All variables used in the figures are as defined below or in the claims.

[0181] exist Figure A Among them, the compounds of the invention can be prepared by one of several methods starting from the appropriate 4-hydroxyquinoline-3-carboxylate a-1. In the first method A-1, ester a-1 is suspended in 5-10 parts of amine and the mixture is heated to 190-200° C. for 30 minutes to 4 hours. Product a-2 was isolated by diluting the cooled reaction mixture with hexane or toluene and collecting the solid precipitate b...

Embodiment 2

[0632] Elemental analysis found values: C, 56.74; H, 3.44; N, 7.35; Cl, ​​9.04. Example 2 7-amino-N-[(4-chlorophenyl)methyl]-4-hydroxyl-3-quinoline carboxamide

[0633] A suspension of 0.60 mL of 4-chlorobenzylamine and 0.200 g of ethyl 4-hydroxy-7-nitro-3-quinolinecarboxylate was heated at 180° C. for 1 hour. The reaction solution was cooled to room temperature. Ethyl acetate was added and the solid formed was collected and washed with ethyl acetate to give 0.071 g of the title compound as a tan solid.

[0634] The physical properties are as follows:

[0635] Mp 244-245°C (decomposition).

[0636] 1 H NMR (DMSO) δ 12.10, 10.63, 8.44, 7.85, 7.37, 7.31, 6.67, 6.53, 6.13, 4.49.

[0637] 13 C NMR (DMSO) δ 175.9, 165.6, 153.4, 142.8, 141.9, 139.3, 131.8, 129.6, 128.8, 127.1, 116.9, 114.8, 109.8, 97.9, 41.7.

[0638] IR (grinding) 3480, 3357, 2748, 2726, 1650, 1586, 1553, 1528, 1506, 1494, 1480, 1281, 789, 737, 621cm -1 .

[0639] MS(EI) m / z 327(M + ), 329, 327, 188, 18...

Embodiment 3

[0640] HRMS (EI) found 327.0778. Example 3 N-[(4-chlorophenyl)methyl]-8-fluoro-4,6-dihydroxy-3-quinoline carboxamide

[0641] To a mixture of 10% Pd / C and 2.0 g 3-fluoro-4-nitrophenol in 10 mL tetrahydrofuran and 10 mL methanol was added 4.817 g ammonium formate. After the reaction solution was stirred at room temperature for 1 hour, it was filtered through celite and then concentrated. Then 2.57 mL of diethyl ethoxymethylene malonate and 10 mL of xylene were added to the residue. The mixture was heated to 135°C for 1 hour and the ethanol formed was removed using a Dean-Stark trap. The reaction solution was cooled. The solid formed was collected, washed with hexanes and dried. The solid was then dissolved in 50 mL of diphenyl ether and heated to 250°C for 3 hours, collecting the ethanol with a Dean-Stark trap. The solution was cooled and diluted with hexanes. The solid formed was collected and dried to yield 0.527g. A solution of 0.415 g of this solid in 4 mL of 4-chl...

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 present invention provide 4-hydroxyquinoline-3-carboxamide and hydrazide compounds of formula (I). These compounds are useful to treat or prevent the herpesviral infections, particularly, human cytomegaloviral infection.

Description

field of invention [0001] The present invention provides 4-hydroxyquinoline-3-carboxamide derivatives, more specifically, the present invention provides N-[(4-chlorophenyl)methyl]-4-hydroxyl-3-quinolinemethanol of formula I Amide compounds. These compounds are useful as antiviral agents, especially of the herpesvirus family. Background of the invention [0002] Herpesviruses comprise a large family of double-stranded DNA viruses. They are the cause of the most common viral diseases in humans. Eight herpesviruses have been confirmed to infect humans, including herpes simplex virus types 1 and 2 (HSV-1 and HSV-2), varicella zoster virus (VZV), human cytomegalovirus (HCMV), Epstein-Barr virus ( EBV) and human herpesviruses 6, 7 and 8 (HHV-6, HHV-7 and HHV-8). [0003] HSV-1 and HSV-2 can cause herpes lesions on the lips and genitals, respectively. They also occasionally cause eye infections and encephalitis. HCMV causes birth defects in infants and v...

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): A61K31/47A61K31/4709A61K31/473A61K31/4738A61K31/4745A61P31/12A61P31/22C07D215/56C07D221/16C07D401/04C07D401/06C07D401/12C07D405/12C07D409/04C07D409/12C07D413/04C07D417/04C07D417/12C07D471/04C07D487/04C07D491/056C07D513/04C07F7/10C07F9/60
CPCC07D417/04C07D401/06C07D405/12C07D513/04C07D409/12C07D215/56C07D401/12C07D413/04C07D409/04C07D417/12C07F9/60C07D487/04C07D221/16C07D401/04A61P31/12A61P31/22C07D215/18C07D215/20C07D215/36C07D215/38C07D215/12C07D207/325C07D231/38
Inventor J·A·图克V·A·维兰库尔特J·W·斯特罗巴克K·R·罗麦尼斯M·E·施努特M·M·库达希S·萨斯里冯格斯S·R·特纳
Owner PHARMACIA & UPJOHN CO
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