Quinone compound, its production and use as antioxidant

Details Quinone compound, its production and use as antioxidant Quinone compound, its production and use as antioxidant

1996-10-23

2000-01-04

Chang, Ceila

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514319, 514320, 546192, 546196, 546236, 546239, C07D21134, A61K 31445

Patent

active

060110465

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to a novel quinone compound, a process for producing it, and a pharmaceutical composition containing it as an active ingredient. The novel quinone compound is useful as an agent for preventing or treating various diseases such as arteriosclerosis, hepatic diseases, cerebrovascular disorders and central nervous damages.


BACKGROUND OF THE INVENTION

As it has become evident that lipoperoxide (peroxylipid) formation in the body and concomitant radical reactions have various harmful effects on the living body through membrane disorders, enzymatic disorders, etc., various attempts to use antioxidants and lipoperoxide formation inhibitors as medicines have been made. At present, the main lipoperoxide formation inhibitors used in the field of medicine are derivatives of natural antioxidants such as vitamin C, vitamin E, etc., and phenol derivatives (Kenji Fukuzawa, The Japanese Journal of Clinical Medicine, 46, 2269-2276, 1988). However, these compounds are not necessarily satisfactory for practical use.
It is believed that the entry of sodium ions through sodium channels into cells results in cell death or tissue damage. It is reported that tetrodotoxin, a sodium channel blocker, relieves such damage. However tetrodotoxin cannot be used for therapy because it is highly toxic (Neurosci. Lett., Vol. 121, pp. 251-254 (1991)).
U.S. Pat. No. 5,059,627 discloses a quinone or hydroquinone compound having nerve growth factor secretion inducing activity. However, this literature fails to specifically disclose a quinone or hydroquinone compound containing 2- or 3-(optionally substituted hydroxy)alkyl or (optionally substituted amino)alkyl on the quinone nucleus, or its lipoperoxide formation inhibitory effect.
Free Radical Biology & Medicine, Vol. 19, No. 2, pp. 197-207 (1995) discloses 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethyl-1,4-benzoquinone or its hydroquinone derivative. However, this literature fails to specifically discloses a quinone or hydroquinone compound containing (optionally substituted amino)alkyl on the quinone nucleus, or its lipoperoxide formation inhibitory effect.
In view of the above, the main object of the present invention is to provide a novel quinone or hydroquinone compound having excellent lipoperoxide formation inhibitory effect and sodium channel blocking effect, an industrially advantageous process for producing it, and a pharmaceutical composition containing it as an active ingredient.


SUMMARY OF THE INVENTION

The present inventors have synthesized many novel compounds and tested their lipoperoxide formation inhibitory effect, binding affinity for sodium channels, etc. As a result, it has been found that a certain kind of novel quinone compound has advantageous pharmaceutical properties such as potent lipoperoxide formation inhibitory effect, high affinity for sodium channels, etc. After further studies based on these findings, the present invention has been accomplished.
The present invention provides (1) a compound of the formula (I): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen, an optionally acylated hydroxyl group, an optionally substituted amino group, an optionally substituted alkoxy group or an optionally substituted hydrocarbon group, or form an optionally substituted hydrocarbon ring; hydrocarbon group or an optionally substituted ring; compound (I)) or its hydroquinone derivative or a salt thereof.
Preferably, the compound of above item (1) is: independently an optionally substituted alkoxy group when R.sup.6 and R.sup.7 are independently an optionally substituted hydrocarbon group; together with the adjacent nitrogen atom, form an optionally substituted ring; independently i) hydrogen, C.sub.6-10 aryl-carbonyl, C.sub.6-10 aryl-C.sub.1-6 alkyl-carbonyl, C.sub.1-6 alkylsulfonyl, C.sub.6-10 arylsulfonyl or C.sub.6-10 aryl-C.sub.1-6 alkylsulfonyl, selected from the group consisting of (a) a C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.6-14 aryl or C.sub

REFERENCES:
patent: 5059627 (1991-10-01), Goto et al.
patent: 5283546 (1994-02-01), Regnier et al.
Diplock et al. "Vitamine E. Biochemistry and healthe implications"N. Y. Aca. Sci. v. 570, pp. 4-5, 1989.
Verne-Mismer et al. "Evaluation of deactivated reversed phases for the analysis of an . . . "CA 119:176879, 1993.
International dicationary of medicine and biology, Wiley & Sons, vo. 1, pp. 561-562, 1992.

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