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US 2014/0212442 A1Published application
Immunomodulators and immunomodulator conjugates
AssigneeRegents of the University of Minnesota
InventorsDavid M. Ferguson, John Ohlfest, Courtney Aldrich
Life of this patent
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Abstract
The invention provides compounds of formula I: wherein R1-R3, Ra, and Rb have any of the values defined herein, and salts thereof. The compounds have immunomodulatory properties.
Claims28
A compound of formula I:
- wherein:
- R1 is Rk—O—C(═O)—;
- R2 is H, NRgRh, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkanoyloxy, RmRnNC(═O)—, or (C1-C6)alkyl optionally substituted with one or more hydroxy, —SH, halo, oxiranyl, (C3-C8)cycloalkyl, aryl, (C1-C6)alkoxy, (C1-C6)alkylthio, or NRgRh;
- R3 is (C1-C6)alkyl, optionally substituted with one or more hydroxy, (C1-C6)alkoxy, aryl, aryl(C1-C6)alkoxy or oxiranyl;
- Ra is H or (C1-C6)alkyl;
- Rb is H or X-Y;
- Rg and Rh are each independently H or or (C1-C6)alkyl;
- or taken together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino ring, which ring may optionally be substituted with one or more (C1-C6)alkyl;
- Rk is H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, trifluoromethyl, aryl, or aryl(C1-C6)alkyl, wherein each (C1-C6)alkyl can optionally be substituted with one or more halo, (C1-C6)alkanoyloxy, (C1-C6)alkoxy, (C3-C8)cycloalkyl;
- Rm and Rn are each independently H or or (C1-C6)alkyl;
- or taken together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino ring, which ring may optionally be substituted with one or more (C1-C6)alkyl;
- X is a linking group;
- and
- Y is an antigen or maleimide;
- wherein the tricyclic ring structure in formula I can optionally be further substituted on one or more carbons with one or more groups independently selected from halo, hydroxy, nitro, (C1-C6)alkyl, (C1-C6)alkenyl, (C1-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)alkanoyl, (C1-C6)alkanoyloxy, (C1-C6)alkoxycarbonyl, trifluoromethyl, trifluoromethoxy, cyano, and NRpRq;
- and
- Rp and Rq are each independently H or or (C1-C6)alkyl;
- or taken together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino ring, which ring may optionally be substituted with one or more (C1-C6)alkyl;
- or a salt thereof.
16 more elements
18-21. (canceled)
A compound selected from:
- and salts thereof.
29-31. (canceled)
33-34. (canceled)
Dependencies are inferred from the claim text.