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US 7,064,124 B2Granted
NF-κB inhibitor containing substituted benzoic acid derivative as active ingredient
AssigneesDaiichi Suntory Pharma Co., Ltd., Daiichi Suntory Biomedical Research, Ltd.
InventorsKenji Suzuki, Yoichi Nunokawa, Naohisa Ogou
Life of this patent
Estimating the term…
Abstract
A NF-κB inhibitor represented by the following formula (I) is provided:
Claims12
A substituted benzoic acid derivative represented by the following formula (I):
- wherein
- R1 is the following formula (II):
- or the following formula (III):
- wherein
- R3, R4 and R5 each independently represents an alkyl group having from 1 to 6 carbon atoms, or an alkoxy group having from 1 to 6 carbon atoms;
- R9 and R10 each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, or an acyl group having from 2 to 11 carbon atoms;
- R2 represents a hydrogen atom, a optionally substituted lower alkyl group having from 1 to 6 carbon atoms, an optionally substituted aryl group having from 6 to 12 carbon atoms, an optionally substituted heteroaryl group having from 4 to 11 carbon atoms, an optionally substituted aralkyl group having from 7 to 14 carbon atoms, an optionally substituted heteroarylalkyl group having from 5 to 13 carbon atoms, or an optionally substituted acyl group having from 2 to 11 carbon atoms;
- and
- X represents a carboxyl group which may be esterified or amidated.
6 more elements
A pharmaceutical composition of matter comprising a substituted benzoic acid derivative represented by the following formula (I):
- wherein R1 is the following formula (II):
- or the following formula (III):
- wherein R3, R4 and R5 each independently represents an alkyl group having from 1 to 6 carbon atoms or an alkoxy group having from 1 to 6 carbons, and R9 and R10 each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an acyl group having from 2 to 11 carbon atoms;
- R2 represents a substituent selected from the group consisting of hydrogen atom, an optionally substituted lower alkyl group having from 1 to 6 carbon atoms, an optionally substituted aryl group having from 6 to 12 carbon atoms, an optionally substituted heteroaryl group having from 4 to 11 carbon atoms, an optionally substituted aralkyl group having from 7 to 14 carbon atoms, an optionally substituted heteroarylalkyl group having from 5 to 13 carbon atoms, end an acyl group having from 2 to 11 carbon atoms;
- and
- X represents a carboxyl group which is optionally esterified or amidated,
- or a hydroquinone form, or a pharmaceutically acceptable salt thereof, and
- a pharmaceutically acceptable carrier therefor.
5 more elements
A substituted benzoic acid derivative selected from the group consisting of:
- 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid,
- 6-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid,
- 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid,
- N-[4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoyl]morpholine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoyl]-4-methoxyaniline,
- 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoic acid,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoic acid,
- 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoic acid,
- 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-acetoxybenzoic acid,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-acetoxybenzoic acid,
- 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-acetoxybenzoic acid,
- methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoate,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-methoxybenzoic acid,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-isopropoxybenzoic acid,
- methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-phenoxybenzoate,
- methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-methoxyphenoxy)benzoate,
- methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridylmethyloxy)benzoate,
- methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridylmethyloxy)benzoate,
- methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(tert-butoxycarbonylmethyloxy)benzoate,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-phenoxybenzoic acid,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-methoxyphenoxy)benzoic acid,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridylmethyloxy)benzoic acid,
- 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridylmethyloxy)benzoic acid,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]morpholine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridylmethyloxy)benzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridylmethyloxy)benzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridyloxy)benzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyloxy)benzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(methoxycarbonylmethyloxy)benzoyl]piperidine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-tert-butoxycarbonylmethyloxy)benzoyl]piperidine.
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridylmethyloxy)benzoyl]morpholine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-(pyridylmethyloxy)benzoyl]morpholine.
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridyloxy)benzoyl]morpholine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyloxy)benzoyl]morpholine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(methoxycarbonylmethyloxy)benzoyl]morpholine,
- N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(tert-butoxycarbonylmethyloxy)benzoyl]morpholine,
- 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoic acid,
- 6-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoic acid,
- 3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoic acid,
- 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid,
- 3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid,
- 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoic acid,
- 3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-methoxybenzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-isopropoxybenzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-methoxyphenoxy)benzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoic acid,
- 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridylmethyloxy)benzoic acid,
- N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]piperidine,
- N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]morpholine,
- N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]-4-methoxyaniline,
- N-[6-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]-4-methoxyaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]piperidine,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]morpholine,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-benzyloxybenzoyl]-4-methoxyaniline,
- N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]piperidine,
- N-[3-(5,6-dimethoxy-3-methyl-1 4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]morpholine,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-methoxyaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]piperidine,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]morpholine,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-methoxybenzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-methoxybenzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-methoxybenzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-isopropoxybenzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-isopropoxybenzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-isopropoxybenzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-methoxyphenoxy)benzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-methoxyphenoxy)benzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-methoxyphenoxy)benzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridylmethyloxy)benzoyl]piperidine
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridylmethyloxy)benzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridylmethyloxy)benzoyl]-4-methoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyloxy)benzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyloxy)benzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridyloxy)benzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridyloxy)benzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(methoxycarbonylmethyloxy)benzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(methoxycarbonylmethyloxy)benzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(tert-butoxycarbonylmethyloxy)benzoyl]piperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(tert-butoxycarbonylmethyloxy)benzoyl]morpholine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3,4-dimethoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3,4,5-trimethoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-acetylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-chloroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-morpholinoaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-cyanoaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-trifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3,5-bistrifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-3,4-dimethoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-3,4,5-trimethoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-acetylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-chloroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-morpholinoaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-cyanoaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-trifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-3,5-bistrifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-(S)-1-phenylethylamine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-(R)-1-phenylethylamine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoyl]-1,2,3,4-tetrahydroquinoline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenoxybenzoyl]-2-methylpiperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-1,2,3,4-tetrahydroquinoline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-4-methylpiperidine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-3,4,5-trimethoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-4-acetylaniline,
- methyl 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(tert-butoxycarbonylmethyloxy)benzoate,
- N-(6-chloropyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(2-chloropyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-chloropyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(6-methoxypyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(6-methoxypyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(trifluoromethylsulfonyl)aniline,
- N-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-(trifluoromethylsulfonyl)aniline,
- N-(pyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(pyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(pyridin-4-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-fluoroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-fluoroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3-nitroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2hydroxybenzoyl]-3-nitroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-2-trifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-2-trifluoromethylaniline,
- ethyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoate,
- ethyl N-[5-(5 6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-aminobenzoate,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-cyanomethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-cyanomethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3-trifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-3-trifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-2-nitroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-2-nitroaniline,
- N-(pyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(pyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(pyridin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-cyclopropyl-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-cyclopropyl-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-cyclohexyl-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide
- N-cyclohexyl-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide
- N-methyl-N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-methoxyaniline,
- N-methyl-N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-methoxyaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-trifluoromethylaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-trifluoromethylaniline,
- ethyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyimethyloxy)benzoyl]-4-aminobenzoate,
- N-(pyridin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzamide,
- N-(pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzamide,
- N-cyclopropyl-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzamide,
- N-cyclohexyl-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyimethyloxy)benzamide,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyimethyloxy)benzoyl]-4-trifluoromethylaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(trifluoromethylsulfonyl)aniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-(trifluoromethylsulfonyl)aniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(trifluoromethylsulfonyl)aniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-2,4-dichloroaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-2,4-dichloroaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-morpholinoaniline,
- N-[3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-morpholinoaniline,
- N-(6-methoxypyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(6-methoxypyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(2,6-dimethoxypyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2,6-dimethoxypyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(6-chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(6-chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(2-chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- tert-butyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoate,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoic acid,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-aminobenzoic acid,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-nitroaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-2,6-dichloro-4-trifluoromethoxyaniline,
- N-(3-tert-butoxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(3-hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(3-hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(5-tert-butoxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(5-hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(5-hydroxycarbonylpyridin-2-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-tert-butoxycarbonylaminoaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-tert-butoxycarbonylaminoaniline,
- N-(pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide (methanesulfonate),
- N-(pyridin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide (methanesulfonate),
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-p-phenylenediamine,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-p-phenylenediamine (hydrochloride),
- N-(pyridin-3-yl)-3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(pyridin-3-yl)-3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(imidazol-1-yl)aniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-(imidazol-1-yl)aniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-(1H-pyrazol-3-yl)aniline,
- N-(5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-(1H-pyrazol-3-yl)aniline,
- N-methyl-N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-trifluoromethylaniline,
- N-methyl-N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-trifluoromethylaniline,
- t-butyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-aminobenzoate,
- N-(2-methoxypyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-methoxypyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybezamide,
- N-(2-dimethylaminopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-dimethylaminopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybezamide,
- N-(5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-2,5-dimethoxyaniline,
- N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-2,5-dimethoxyaniline,
- N-(2-chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-methoxybenzamide,
- N-(2-morpholinopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-morpholinopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(6-morpholinopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(6-morpholinopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(2-chloropyridin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-chloropyridin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(6-methoxypyrimidin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(6-methoxypyrimidin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(2-methoxypyridin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-methoxypyridin-4-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- 5-(2,5-dimethoxy-3,4,6-trimethylbenzyl)-2-acetoxybenzoic acid,
- 5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid,
- N-[5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-trifluoromethylaniline,
- N-[5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-4-trifluoromethylaniline,
- N-(2-chloropyridin-3-yl)-5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide,
- N-(2-chloropyridin-3-yl)-5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide,
- N-(pyridin-4-yl)-5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide.
235 more elements
Dependencies are inferred from the claim text.