6,7-Disubstituted -5,8-quinolinedione derivatives as an...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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Details

C514S313000, C546S171000, C546S153000

Reexamination Certificate

active

06818653

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to 6,7-disubstituted-5,8-quinolindion derivatives as an antifungal agent expressed in the following formula 1 which has excellent antifungal activity against funges infecting human and animals,
wherein
R
1
represents phenylamino group substituted 1 to 3 with a substituent selected from the group consisting of a halogen atone and an aceto group, or C
1
-C
20
alkylmercapto group; and
R
2
represents thiocyano group; or C
1
-C
20
alkylmercapto group.
2. Description of the Prior Art
The recent increase of fungal infections has generated a renewed interest in antifungal drugs, including development of new antifungal agents. We focused on developing 6,7-disubstituted-5,8-quinolinediones with noble mode of antifungal activities. As antimetabolites of coenzyme Q, the 6-(substituted)-7-chloro-5,8-quinolinediones inhibit mitochondrial Co-Q dependent succinoxidase and electron transport in
Saccaromyces cerevisiae
, that may be correlated with antifungal activity (
Arch. Biochem. Biophys
., 191, 306-315, 1978). The 5,8-quinolindiones, as antimetabolites of coenzyme Q, inhibit cytochrome bc complex due to blockade of mitochondrial electron transport in fungi (
J. Med. Chem
., 16, 206-209, 1973). 6/7-Substituted-5,8-quinolinedione derivatives have also been reported fungicide in German Patent Publication No. 4, 208, 874 (1993), but no antifungal activity against human pathogenic fungi was not tested or mentioned.
SUMMARY OF THE INVENTION
The present invention has been completed by synthesizing 6,7-disubstituted-5,8-quinolinedion derivatives and confirming the antifungal activity thereof.
Therefore, an object of the present invention is to provide 6,7-disubstituted-5,8-quinolinedion derivatives expressed in the formula 1, including its preparing method and use as an antifungal agent.


REFERENCES:
patent: 4208874 (1993-09-01), None
patent: 519290 (1992-09-01), None
Jalpana Roy et al. Caplius enlish Abstract 1981:30533 Caplus DN 94:30533 Reaction of 6-arylamino-7-bromoquinoline-5,8-dione with nucleophiles (1980), 19B(6), 512-13.*
Gopalachari et al. English Abstract Caplus 1962:456172 Caplus DN 57:56172 57:11160c-i,11161a-d Potential amebicides. XV. Synthesis of 7-(and 6,7-di)substituted quinoline-5,8-quinones and 7-substituted 5-pchlorobenzoyl-(and benzyl)-8-hydroxyquinoline.*
Ryu, Chang-Kyu et al The antifungal activities of some 6-[N-(halophenyl)amino]-7-chloro-5,8-quinolinediones against Candida species (1994), 17(6), 483-6. (English Abstract Caplus).*
Bowman et al., Antimetabolites of Coenzyme Q.14. Quinolinequinone Analogs Which Inhibit Mitochondrial DPNH-Oxidase and Succinoxidase,Journal of Medicinal Chemistry, vol. 16, No. 3, 206-209, 1973.
Roberts et al., The Site of Inhibition of Mitochondrial Electron Transfer by Coenzyme Q Analogues,Arch. Biochem. Biophys., vol. 191, No. 1, 306-315, 1978.

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