NF-κB inhibitor comprising phenylmethyl benzoquinone as the active ingredient
View Patent ↗An NF-κB inhibitor having as an active ingredient a benzoquinone derivative represented by the general formula (1) wherein R 1 , R 2 , and R 3 are each independently H, alkyl having 1 to 5 carbons, or alkoxy having 1 to 5 carbons; R 4 is H, hydroxymethyl, alkyl, or carboxyl which is optionally esterified or amidated; Z is represented by the formula (A); and, n is an integer from 0 to 6, or its hydroquinone form or a pharmaceutically acceptable salt thereof.
1. A method for treatment of inflammatory diseases comprising administering to a patient in need of such treatment an effective amount of a benzoquinone derivative represented by the following general formula (I):
wherein
R 1 , R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbons, or an alkoxy group having 1 to 5 carbons;
R 4 is a hydrogen atom, a hydroxymethyl group, an alkyl group, or a carboxyl group which is optionally esterified or amidated; Z is
and, n is an integer from 0 to 6, or its hydroquinone form, or a pharmaceutically acceptable salt thereof.
2. The method according to claim 1 wherein R 1 and R 2 are a hydrogen atom, a methyl group, or a methoxy group.
3. The method according to claim 1 wherein R 3 is a hydrogen atom or a methyl group.
4. The method according to claim 1 wherein Z is
n is an integer 0.
5. The method according to claim 1 wherein Z is
and n is an integer 1, 2, or 3.
6. The method according to claim 1 wherein R 4 is a group —COOR 5 wherein R 5 is a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbons, an optionally substituted phenyl group, or an optionally substituted aralkyl group having 7 to 11 carbons.
7. The method according to claim 1 wherein R 4 is a group —CONR 6 R 7 wherein R 6 and R 7 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 8 carbons, an optionally substituted bicyclic unsaturated or partially saturated hydrocarbon ring group having 9 to 11 carbons, an optionally substituted heterocyclic group, an optionally substituted phenyl group, an optionally substituted aralkyl group having 7 to 11 carbons, or a heteroaryl-C 1 -C 3 -alkyl group, or R 6 and R 7 , together with the nitrogen atom to which they are attached, represent a heterocyclic group which may further contain a nitrogen, oxygen, and/or sulfur atom.
8. The method according to claim 1 wherein R 4 is a group —CONR 6 R 7 wherein R 6 and R 7 , together with the nitrogen atom to which they are attached, represent a 5- to 10-membered optionally substituted, nitrogen-containing heterocyclic group which may contain, in addition to the carbon and nitrogen atom, 1 to 3 heteroatoms selected from the group consisting of a nitrogen, oxygen and sulfur atom, the carbon atom on said cyclic group being optionally a ketone form or the sulfur atom on said cyclic group being optionally an oxide form.
9. The method according to claim 1 wherein R 1 and R 2 are a methyl group or a methoxy group; R 3 is a methyl group: R 4 is a carboxyl group which is optionally esterified or amidated; Z is
and n is an integer 1, 2, or 3.