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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: 2002-06-19
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

[0044] Example 1: 5-nitroso-8-hydroxyquinoline hydrochloride

[0045] Add NaNO to a mixture 2 Aqueous solution, of which water is 100ml, NaNO 2 It is 30g, the adding time is 1 hour, the temperature is 0-4℃, the mixture is composed of the following materials: 8-hydroxyquinoline (58g, 0.4 mol) in distilled water, concentrated hydrochloric acid (75ml) and ice ( 200g). During the whole night, the reactant was kept at 0°C, and then filtered by washing with cold water to obtain 5-nitroso-8-hydroxyquinoline hydrochloride (95%).

example 2

[0046] Example 2: 5-amino-8-hydroxyquinoline dihydrochloride

[0047] To a mixture consisting of water (160ml) and 5N-NaOH (260ml), 5-amino-8-hydroxyquinoline chloride (40g) was added and heated to 40°C. Add Na to the reaction mixture 2 S 2 O 4 (95g), the reaction temperature was increased 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 obtain 5-amino-8-hydroxyquinoline dihydrochloride (34 g, 69%).

example 3

[0048] Example 3: 6,7-dihalo-5,8-quinolinedione of structural formula 2

[0049] After adding 5-amino-8-hydroxyquinoline dihydrochloride (9g) to hydrochloric acid (81g), the reaction mixture was heated to 60°C and NaClO was added 3 (4.5g). At a temperature of 50-60°C, the reaction mixture was stirred for 30 minutes, filtered, and recrystallized twice with butanol to obtain 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 6,7-second-generation-5,8-quinolindione derivative used as an antifungal agent. The derivative is represented by the following structural formula 1. This antifungal agent is effective for humans and animals. The fungus that causes the infection has excellent antifungal activity. [0002] among them: [0003] R 1 Represents an aniline group, substituted by 1 to 3 substituents, the substituents are selected from a group, this group includes a halogen atom, and an acetyl group, or C 1 -C 20 的alkylthiol group; [0004] R 2 Represents thiocyanate; or C 1 -C 20 的alkylthiol group. Background technique [0005] The recent increase in fungal infections has prompted new interest in antifungal drugs. 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-chloro-...

Claims

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Application Information

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IPC IPC(8): C07D215/00A61K31/47A61P31/10C07D215/36C07D215/38
CPCC07D215/38C07D215/36A61P31/10C07D215/00
Inventor 柳忠珪
Owner ILJIN COPPER FOIL
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