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US 8,207,381 B2Granted
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): 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.
Claims36
A compound of Formula (I):
- wherein:
- R1 is (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, (C2-C20) alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, NRaRb, (C2-C20)alkynoyloxy, and arylcarbonyloxy;
- R2 is CF2Br, CF2Cl, CFBr2, CFCl2, CBr3, CF(Re)Br, CF2I, 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;
- 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, heteroaryl, aryl(C1-C20)alkyl, heteroaryl(C1-C20)alkyl, aryl(C2-C2o)alkenyl, aryl(C2-C20)alkynyl, heteroaryl(C2-C20)alkenyl, heteroaryl(C2-C20)alkynyl, (C1-C20)alkanoyloxy, (C2-C20)alkenoyloxy, (C2-C20)alkynoyloxy;
- or a salt thereof;
- provided the compound is not 4-bromo-4,4-difluorobut-2-ynoic acid or 1-bromo-1,1-difluoro-non-2-yn-4-ol.
6 more elements
A compound of Formula (I):
- or a salt thereof, wherein R1 is a (C5-C10)alkyl, (C2-C10)alkenyl, or (C2-C10)alkynyl that is substituted with hydroxy;
- 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 Rc and Rd is independently H, (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2C20)alkynylcarbonyl, (C1-C20)alkoxy, (C2-C20)alkenyloxy, or (C2-C20)alkynyloxy;
- and
- Re is (C1-C20)alkyl, (C1-C20)alkanoyl, (C2-C20)alkenylcarbonyl, (C2-C20)alkynylcarbonyl, (C1-C20)alkoxy, (C,2-C20)alkenyloxy, or (C2-C20)alkynyloxy.
2 more elements
The compound 1-bromo-1,1,difluoro-4-hydroxy-5,5-dimethyl-2-hexyne, or a salt thereof.
The compound
- or a salt thereof.
A pharmaceutical composition comprising a compound of Formula (I):
- wherein:
- R1 is (C1-C20)alkyl, (C2-C20)alkenyl, or (C2-C20)alkynyl, which (C1-C20)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, (C2 C20)alkenyloxycarbonyl, (C2-C20)alkynyloxycarbonyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, NRaRb, (C2-C20)alkynoyloxy, and arylcarbonyloxy;
- R2 is CF2Br, CF2Cl, CFBR2, CFCl2, CBr3, CF(Re)Br, CF2I, 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)alkynloxy, or aryl-(C1-C20)alkoxycarbonyl;
- 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, or heteroaryloxy, arylcarbonyloxy or heteroarylcarbonyloxy or R1 is optionally substituted with one or more goups 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)alkynylcarbonyl, aryl, heteroaryl, 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)alkenoyloxy, (C2-C20)alkynyloxy;
- or a pharmaceutically acceptable salt thereof;
- and a pharmaceutically acceptable carrier;
- provided the compound is not 4-bromo-4,4-difluorobut-2-ynoic acid or 1-bromo-1,1-difluoro-non-2-yn-4-ol.
7 more elements
Dependencies are inferred from the claim text.