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US 11,926,641 B2Granted
Phosphonamidate butyrophilin ligands
AssigneeUniversity of Iowa Research Foundation
InventorsDavid F. Wiemer, Andrew J. Wiemer
Life of this patent
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Abstract
The invention provides a compound of formula I: or a salt thereof, wherein R1-R4 have any of the values described in the specification, as well as compositions comprising a compound of formula I. The compounds are useful in immunotherapy as a potential treatment, or co-treatment, for cancer or infectious diseases.
Claims18
A compound of formula I:
- or a salt thereof, wherein:
- R1 is aryl, 5-6 membered heteroaryl, aryl(C1-C6)alkyl, or (5-6 membered heteroaryl)(C1-C6)alkyl, wherein any aryl, 5-6 membered heteroaryl, aryl(C1-C6)alkyl, or (5-6 membered heteroaryl)(C1-C6)alkyl is optionally substituted with one or more groups Rx independently selected from the group consisting of hydroxyl, halo, nitro, cyano, carboxy, NRaRb, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio, and (C2-C6)alkanoyloxy, wherein any (C1-C6)alkyl and (C1-C6)alkoxy of Rx is optionally substituted with one or more groups independently selected from halo;
- R2 is (C1-C6)alkyl that is optionally substituted with one or more groups independently selected from the group consisting of hydroxy, halo, nitro, cyano, carboxy, NRcRd, (C1-C6)alkoxy, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio, and (C2-C6)alkanoyloxy;
- R3 is oxo (═O) or hydroxy;
- R4 is the side-chain of a natural amino acid;
- each Ra and Rb is independently selected from the group consisting of H, (C1-C6)alkyl, (C3-C6)cycloalkyl, and (C3-C6)cycloalkyl(C1-C6)alkyl;
- or Ra and Rb together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino, which aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino is optionally substituted with one or more groups independently selected from the group consisting of halo and (C1-C6)alkyl;
- and
- each Rc and Rd is independently selected from the group consisting of H, (C1-C6)alkyl, (C3-C6)cycloalkyl, and (C3-C6)cycloalkyl(C1-C6)alkyl;
- or Rc and Rd together with the nitrogen to which they are attached form a aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino, which aziridino, azetidino, morpholino, piperazino, pyrrolidino or piperidino is optionally substituted with one or more groups independently selected from the group consisting of halo and (C1-C6)alkyl.
7 more elements
A compound selected from:
- or a salt thereof.
Dependencies are inferred from the claim text.