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US 8,263,594 B2Granted
Aryloxy and arylalkyleneoxy substituted imidazoquinolines
Assignee3M Innovative Properties Company
InventorsKyle J. Lindstrom, Hugues M. H. Martin, Bryon A. Merrill, Michael J. Rice, Joshua R. Wurst, Chad A. Haraldson, Philip D. Heppner, Shri Niwas, Matthew R. Radmer
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Abstract
Imidazoquinoline compounds with an aryloxy or arylalkyleneoxy substituent at the 6, 7, 8, or 9-position, pharmaceutical compositions containing the compounds, intermediates, and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.
Claims27
A compound of the formula (II):
- wherein:
- R3 is —Z—Ar,
- Z is selected from the group consisting of a bond and alkylene;
- Ar is phenyl which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, nitro, cyano, halogen, amino, alkylamino, dialkylamino, trifluoromethyl, and trifluoromethoxy;
- R is selected from the group consisting of alkyl, alkoxy, hydroxy, halogen, and trifluoromethyl;
- n is 0 or 1;
- R1 is —R4,
- R2 is selected from the group consisting of hydrogen, alkyl, and alkoxyalkylenyl;
- R4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of acetyl, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkanoyloxy, alkoxycarbonyl, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, mercapto, cyano, formyl, aryl, aryloxy, arylthio, arylsulfonyl, arylalkyleneoxy, aroylamino, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, aminosulfonyl, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;
- or a pharmaceutically acceptable salt thereof.
7 more elements
Dependencies are inferred from the claim text.