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US 2012/0329866 A1Published application
Therapeutic compounds
AssigneeUniversity of Louisville Research Foundation, Inc.
InventorsGerald B. Hammond, Bo Xu, Paula J. Bates
Life of this patent
Estimating the term…
Abstract
The invention provides compounds of Formula (I): R1≡R2 (I) wherein R1 and R2 have any of the values or specific values defined herein, as well as compositions comprising such compounds and therapeutic methods comprising the administration of such compounds.
Claims22
1-28. (canceled)
A method for treating cancer in an animal comprising administering to the animal a compound of Formula (I):
- R1≡R2 (I)
- wherein:
- R1 is carboxy, (C1-C20)alkoxycarbonyl, (C2-C20)alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, (C1-C20)alkoxycarbonyl, (C1-C20)alkyl, (C2-C20)alkenyl, or (C2-C20)alkynyl, which (C1-20)alkyl, (C2-C20)alkenyl, or (C2-C20)alkynyl, is substituted with one or more groups independently selected from halo, hydroxy, mercapto, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, aryloxy, heteroaryloxy, (C3-C20)cycloalkyloxy, heterocyclyloxy, (C1-C20)alkylthio, (C2-C20)alkenylthio, (C2-C20)alkynylthio, carboxy, (C1-C20)alkoxycarbonyl, (C2-C20)alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, NRaRb, (C2-C20)alkynoyloxy, and arylcarbonyloxy;
- R2 is CF2Br, CFHBr, CF2Cl, CFHCl, CFBr2, CFCl2, CBr3, C(Rc)(Rd)Br, C(Rc)(Rd)Cl, CF(Re)Br, CF2I, CFHI, C(Rc)(Rd)I, CF(Re)I or CCl3;
- each Ra and Rb is independently H, (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, or aryl-(C1-C20)alkoxycarbonyl;
- each Rc and Rd is independently H, (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, or (C1-C20)alkynyloxy;
- and
- Re is (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, or (C2-C20)alkynyloxy;
- wherein each aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy, arylcarbonyloxy or heteroarylcarbonyloxy of R1 is optionally substituted with one or more groups independently selected from halo, hydroxy, nitro, cyano, trifluoromethyl, trifluoromethoxy, mercapto, carboxy, (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, (C1-C20)alkylthio, (C2-C20)alkenylthio, (C2-C20)alkynylthio, (C1-C20)alkoxycarbonyl, (C2-C20)alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, aryl, hetero aryl, aryl(C1-C20)alkyl, heteroaryl(C1-C20)alkyl, aryl(C2-C20)alkenyl, aryl(C2-C20)alkynyl, heteroaryl(C2-C20)alkenyl, heteroaryl(C2-C20)alkynyl, (C1-C20)alkanoyloxy, (C2-C20)alkenoyloxy, (C2-C20)alkynoyloxy;
- or a pharmaceutically acceptable salt thereof.
7 more elements
(canceled)
A method for inhibiting methyltransferase activity,
- wherein the method comprises administering an effective amount of a compound of Formula (I):
- R1≡R2 (I)
- wherein:
- R1 is carboxy, (C1-C20)alkoxycarbonyl, (C2-C20)alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, (C1-C20)alkoxycarbonyl, (C1-C20)alkyl, (C2-C20)alkenyl, or (C2-C20)alkynyl, which (C1-20)alkyl, (C2-C20)alkenyl, or (C2-C20)alkynyl, is substituted with one or more groups independently selected from halo, hydroxy, mercapto, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, aryloxy, heteroaryloxy, (C3-C20)cycloalkyloxy, heterocyclyloxy, (C1-C20)alkylthio, (C2-C20)alkenylthio, (C2-C20)alkynylthio, carboxy, (C1-C20)alkoxycarbonyl, (C2-C20)alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, NRaRb, (C2-C20)alkynoyloxy, and arylcarbonyloxy;
- R2 is CF2Br, CFHBr, CF2Cl, CFHCl, CFBr2, CFCl2, CBr3, C(Rc)(Rd)Br, C(Rc)(Rd)Cl, CF(Re)Br, CF2I, CFHI, C(Rc)(Rd)I, CF(Re)I or CCl3;
- each Ra and Rb is independently H, (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, or aryl-(C1-C20)alkoxycarbonyl;
- each Rc and Rd is independently H, (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, or (C1-C20)alkynyloxy;
- and
- Re is (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, or (C2-C20)alkynyloxy;
- wherein each aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy, arylcarbonyloxy or heteroarylcarbonyloxy of R1 is optionally substituted with one or more groups independently selected from halo, hydroxy, nitro, cyano, trifluoromethyl, trifluoromethoxy, mercapto, carboxy, (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, (C2-C20)alkynyloxy, (C1-C20)alkylthio, (C2-C20)alkenylthio, (C2-C20)alkynylthio, (C1-C20)alkoxycarbonyl, (C2-C20)alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, aryl, hetero aryl, aryl(C1-C20)alkyl, heteroaryl(C1-C20)alkyl, aryl(C2-C20)alkenyl, aryl(C2-C20)alkynyl, heteroaryl(C2-C20)alkenyl, heteroaryl(C2-C20)alkynyl, (C1-C20)alkanoyloxy, (C2-C20)alkenoyloxy, (C2-C20)alkynoyloxy;
- or a pharmaceutically acceptable salt thereof.
8 more elements
35-36. (canceled)
The method of claim 35, wherein the compound of formula (I) is a compound of formula (II):
- wherein:
- R3 is hydroxy, mercapto, chloro, bromo, methylthio, ethylthio, methoxy, ethoxy, acetylamino, (C1-C20)alkanoyloxy, arylcarbonyloxy, aryloxy;
- and R4 is (C4-C10)alkyl, (C2-C10)alkenyl, or (C2-C10)alkynyl, which (C4-C10)alkyl, (C2-C10)alkenyl, or (C2-C10)alkynyl is optionally substituted with one or more groups independently selected from halo, hydroxy, mercapto, (C1-C10)alkoxy, (C1-C10)alkylthio, carboxy, (C1-C10)alkoxycarbonyl, aryl, heteroaryl, and NRaRb.
The method of claim 35, wherein the compound of Formula (I) is 1-bromo-1,1, difluoro-4-hydroxy-5,5-dimethyl-2-hexyne.
The method of claim 35, wherein the compound of Formula (I) is a compound having the formula:
Dependencies are inferred from the claim text.