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6.7-disubstituted-5,8-quinolinedione derivatives as antifungal agent

A kind of quinoline dione, antifungal technology, applied in 6 fields, can solve the problem of human pathology fungi antifungal activity experiment or mention and so on

Inactive Publication Date: 2004-05-05
ILJIN COPPER FOIL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In German Patent Publication 4,208,874 (1993), 6 / 7 generation-5,8-quinolinedione derivatives have also been reported as fungicides, but the antifungal activity of human pathological fungi has not been tested or proposed. and

Method used

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  • 6.7-disubstituted-5,8-quinolinedione derivatives as antifungal agent
  • 6.7-disubstituted-5,8-quinolinedione derivatives as antifungal agent
  • 6.7-disubstituted-5,8-quinolinedione derivatives as antifungal agent

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0056] Example 1: 5-nitroso-8-hydroxyquinoline hydrochloride

[0057] Add NaNO to a mixture 2 Aqueous solution, in which water is 100ml, NaNO 2 is 30g, the time of addition is 1 hour, and the temperature is 0-4 ℃. The mixture is made up of the following substances: 8-hydroxyquinoline (58g, 0.4 mol) in distilled water, concentrated hydrochloric acid (75ml) and ice ( 200g). The reaction was kept at 0°C throughout overnight and then filtered by washing with cold water to yield 5-nitroso-8-hydroxyquinoline hydrochloride (95%).

example 2

[0058] Example 2: 5-amino-8-hydroxyquinoline dihydrochloride

[0059] To a mixture consisting of water (160ml) and 5N-NaOH (260ml) was added 5-amino-8-hydroxyquinoline chloride (40g) and heated to 40°C. Na was added to the reaction mixture 2 S 2 o 4 (95g), the reaction temperature was raised to 75-80°C. The reaction mixture was cooled to 50°C, and 12N-HCL (250 ml) was added to the reaction mixture. The reaction mixture was then cooled to 0°C and filtered to give 5-amino-8-hydroxyquinoline dihydrochloride (34 g, 69%).

example 3

[0060] Example 3: 6,7-dihalo-5,8-quinolinedione of structural formula 2

[0061] After adding 5-amino-8-hydroxyquinoline dihydrochloride (9 g) to hydrochloric acid (81 g), the reaction mixture was heated to 60° C., and NaClO 3 (4.5g). The reaction mixture was stirred for 30 minutes at a temperature of 50-60° C., filtered, and recrystallized twice from butanol to give 6,7-dihalo-5,8-quinolinedione (90%) yellow Precipitate. Melting point: 221-222°C.

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Abstract

An antifungal agent 6,7-disubstituted-5,8-quinolinedione derivatives, general formula represents 6,7-disubstituted-5,8-quinolinedione, wherein R1 represents phenylamino group substituted 1 to 3 with a substituent selected from the group consisting of a halogen atom and aceto group or a Cl-C20 alkylmercapto group, R2 represents thiocyano group or Cl-C20 alkylmercapto group. 6,7-disubstituted-5,8-quinolinedione derivatives and pharmaceutical acceptable salts theirof have a excellent antifungal activity. The invention disclosed a pharmaceutical composition which contains the compound as a active component, which has excellent antifungal activity against funges infecting human and animals.

Description

technical field [0001] The present invention relates to a kind of 6,7-second-generation-5,8-quinolinedione derivatives used as antifungal agents, the derivatives are represented by the following structural formula 1, and this antifungal agent is harmful to humans and animals The fungus causing the infection has excellent antifungal activity. [0002] [0003] in: [0004] R 1 Represents an anilino group, substituted by 1 to 3 substituents selected from a group consisting of a halogen atom, and an acetyl group, or C 1 -C 20 The alkylthiol group; [0005] R 2 represents thiocyanate; or C 1 -C 20 of alkylthiol groups. Background technique [0006] The recent increase in fungal infections has prompted renewed interest in antifungal agents. These include the development of new antibacterial drugs. We focused our attention on developing a 6,7-second-generation-5,8-quinolinedione with excellent antifungal activity. As an antimetabolite of coenzyme Q, 6-(generation)-7-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/00A61K31/47A61P31/10C07D215/36C07D215/38
CPCC07D215/38C07D215/36A61P31/10C07D215/00
Inventor 柳忠珪
Owner ILJIN COPPER FOIL