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US 2013/0210918 A1Published application
Treatment of friedreich's ataxia using histone deacetylase inhibitors
AssigneeThe Scripps Research Institute
InventorsJoel M. Gottesfeld, Kai Jenssen, David M. Herman, Ryan Burnett, C. James Chou
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Abstract
The invention provides methods of treating Friedreich's ataxia using histone deacetylase inhibitors.
Claims21
A method of treating or delaying the onset of Friedreich's ataxia in a mammal comprising administering to the mammal a histone deacetylase inhibitor in an amount effective to inhibit a histone deacetylase in the mammal.
A method for preparing a compound of formula I:
- wherein:
- n is 2 to about 10;
- R1 is aryl or heteroaryl;
- R2 is aryl or heteroaryl;
- Ra and Rb are each independently H, alkyl, aryl, heteroaryl, or a nitrogen protecting group;
- wherein any alkyl, aryl or heteroaryl is optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, amino, nitro, cyano, halo, alkyl, trifluoromethyl, alkoxy, aryl, and NRcRd;
- wherein Rc and Rd are each independently hydrogen, alkyl, or C(═O)ORe wherein Re is H or alkyl;
- or a salt thereof;
- comprising contacting a compound of formula V:
- with one or more coupling agents and a compound of formula VI:
- R2—NH(Rb) (VI)
- to provide the compound of formula I.
9 more elements
A method for preparing a compound of formula I:
- wherein:
- n is 3 to about 10;
- R1 is aryl or heteroaryl;
- R2 is aryl or heteroaryl;
- Ra and Rb are H, alkyl, aryl, heteroaryl, or a nitrogen protecting group;
- wherein any alkyl, aryl or heteroaryl is optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, amino, nitro, cyano, halo, alkyl, trifluoromethyl, alkoxy, aryl, and NRcRd;
- wherein Rc and Rd are each independently hydrogen, alkyl, or C(═O)ORe wherein Re is H or alkyl;
- the method comprising:
- (a) contacting a compound of formula II:
- with a dehydrating agent to provide a compound of formula III:
- (b) contacting the compound of formula III with a compound of formula IV:
- R1—NH(Ra) (IV)
- to provide a compound of formula V:
- (c) contacting the compound of formula V with one or more coupling agents and a compound of formula VI:
- R2—NH(Rb) (VI)
- to provide the compound of formula I.
13 more elements
A pharmaceutical composition comprising a compound of formula I:
- wherein:
- n is 2 to about 10;
- R1 is aryl or heteroaryl;
- R2 is aryl or heteroaryl;
- Ra and Rb are each independently H, alkyl, aryl, heteroaryl, or a nitrogen protecting group;
- wherein any alkyl, aryl or heteroaryl is optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, amino, nitro, cyano, halo, alkyl, trifluoromethyl, alkoxy, aryl, and NRcRd;
- wherein Rc and Rd are each independently hydrogen, alkyl, or C(═O)ORe wherein Re is H or alkyl;
- or a salt thereof;
- in combination with a pharmaceutically acceptable carrier.
6 more elements
Dependencies are inferred from the claim text.