Specific inhibitors of cytochrome P450 26 retinoic acid hydroxylase

US9963439B2 · kind B2 · utility

Assignees

• University of Washington through its Center for Commercialization · US
• University of Montana · US

Inventors

• Philippe Diaz · Nice, FR
• Nina Isoherranen · Seattle, US
• Brian Buttrick · Seattle, US
• Nicolas Guilloteau · Missoula, US

Key dates

• Filing date: Aug 20, 2014
• Grant date: May 8, 2018
• Expiry date: Aug 20, 2034

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/74
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present disclosure is generally directed to compositions and methods for treating diseases that are ameliorated by the inhibition of CYP26 mediated retinoic acid metabolism. The compositions comprise compounds of formula (I). A repreid50000060307390 IB/345 nullsents aryl optionally substituted with one, two, three, or four groups that are each independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, and C1-C6 haloalkoxy; X is a bond, —CH2—, —CHR5—, —C═CHR4—, —NR4—, —N═O—R4—, —O—, —S—, —SO—, —SO2—, —C(O)—, or —C(NR4)—, or X is of formula (a), (b) or (c), wherein each n is independently 1, 2, or 3; each R4 is independently hydrogen or C1-6 alkyl; R5 is independently hydrogen, C1-6 alkyl, or —OR6, where R6 is selected from the group consisting of hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyL C3-12 cycloalkyl, heterocyclyl, aryl, arylC1-6 alkyl, heteroaryl, or heteroarylC1-6 alkyl; Y is C1-6 alkylene, C2-6 alkenylene, or C2-6 alkylylene moiety.