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US 2024/0180948 A1Published application
4'-halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto
AssigneeEmory University
InventorsGeorge R. PAINTER, David PERRYMAN, Gregory R. BLUEMLING
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Abstract
Disclosed are halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections. Such viral infections can include tongaviridae, bunyaviridae, arenaviridae, coronaviridae, flaviviridae, picornaviridae, Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infections.
Claims23
1-428. (canceled)
A compound of Formula XXVIII,
- or a pharmaceutically acceptable salt thereof, wherein
- R1 is selected from,
- wherein R1 is optionally substituted with one or more, the same or different, R10;
- Y is O;
- R2 is selected from hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkenyl, alkoxy, hydroxy, thiol, amino, azido, formyl, acyl, cyano, halogen, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocarbocyclyl, sulfinyl, sulfamoyl, or sulfonyl, wherein R2 is optionally substituted with one or more, the same or different, R10;
- R3 is selected from hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkenyl, alkoxy, hydroxy, thiol, amino, azido, formyl, acyl, cyano, halogen, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocarbocyclyl, sulfinyl, sulfamoyl, or sulfonyl, wherein R3 is optionally substituted with one or more, the same or different, R10;
- R6, R6′, R6″, and R6′″ are each independently selected from hydrogen, deuterium, hydroxyl, amino, azido, thiol, acyl, formyl, halogen, nitro, alkyl, alkenyl, alkynyl, carbocyclyl, heterocarbocyclyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkoxy, carbocycloxy, heterocarbocycloxy, aryloxy, heteroaryloxy, heterocyclooxy, cycloalkoxy, cycloalkenoxy, alkylamino, (alkyl)2amino, carbocyclamino, heterocarbocyclamino, arylamino, heteroarylamino, heterocycloamino, cycloalkamino, cycloalkylamino, alkylthio, carbocyclylthio, heterocarbocyclylthio, arylthio, heteroarylthio, heterocyclylthio, cycloalkylthio, cycloalkenylthio, sulfinyl, sulfamoyl, sulfonyl alkenyl, cyano, or lipid, wherein R6, R6′, R6″, and R6′″ can each be optionally substituted with one or more, the same or different, R10;
- R10 is deuterium, hydroxy, azido, thiol, amino, cyano, halogen, alkyl, alkenyl, alkynyl, carbocyclyl, heterocarbocyclyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkoxy, carbocycloxy, heterocarbocycloxy, aryloxy, heteroaryloxy, heterocyclooxy, cycloalkoxy, cycloalkenoxy, alkylamino, (alkyl)2amino, carbocyclamino, heterocarbocyclamino, arylamino, heteroarylamino, heterocycloamino, cycloalkamino, cycloalkylamino, alkylthio, carbocyclylthio, heterocarbocyclylthio, arylthio, heteroarylthio, heterocyclylthio, cycloalkylthio, cycloalkenylthio, alkenyl, sulfinyl, sulfamoyl, sulfonyl, lipid, nitro, or carbonyl, wherein R10 is optionally substituted with one or more, the same or different, R11;
- R11 is deuterium, hydroxy, azido, thiol, amino, cyano, halogen, alkyl, alkenyl, alkynyl, carbocyclyl, heterocarbocyclyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkoxy, carbocycloxy, heterocarbocycloxy, aryloxy, heteroaryloxy, heterocyclooxy, cycloalkoxy, cycloalkenoxy, alkylamino, (alkyl)2amino, carbocyclamino, heterocarbocyclamino, arylamino, heteroarylamino, heterocycloamino, cycloalkamino, cycloalkylamino, alkylthio, carbocyclylthio, heterocarbocyclylthio, arylthio, heteroarylthio, heterocyclylthio, cycloalkylthio, cycloalkenylthio, alkenyl, sulfinyl, sulfamoyl, sulfonyl, lipid, nitro, or carbonyl;
- and
- Lipid is a C11-C22 higher alkyl, C11-C22 higher alkoxy, polyethylene glycol, or aryl substituted with an alkyl group.
8 more elements
A method of treating or preventing a viral infection in a subject in need thereof, comprising providing to the subject a compound of Formula XXVIII,
- or a pharmaceutically acceptable salt thereof, wherein
- R1 is selected from,
- wherein R1 is optionally substituted with one or more, the same or different, R10;
- Y is O;
- R2 is selected from hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkenyl, alkoxy, hydroxy, thiol, amino, azido, formyl, acyl, cyano, halogen, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocarbocyclyl, sulfinyl, sulfamoyl, or sulfonyl, wherein R2 is optionally substituted with one or more, the same or different, R10;
- R3 is selected from hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkenyl, alkoxy, hydroxy, thiol, amino, azido, formyl, acyl, cyano, halogen, aryl, heteroaryl, heterocyclyl, carbocyclyl, heterocarbocyclyl, sulfinyl, sulfamoyl, or sulfonyl, wherein R3 is optionally substituted with one or more, the same or different, R10;
- R6, R6′, R6″, and R6′″ are each independently selected from hydrogen, deuterium, hydroxyl, amino, azido, thiol, acyl, formyl, halogen, nitro, alkyl, alkenyl, alkynyl, carbocyclyl, heterocarbocyclyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkoxy, carbocycloxy, heterocarbocycloxy, aryloxy, heteroaryloxy, heterocyclooxy, cycloalkoxy, cycloalkenoxy, alkylamino, (alkyl)2amino, carbocyclamino, heterocarbocyclamino, arylamino, heteroarylamino, heterocycloamino, cycloalkamino, cycloalkylamino, alkylthio, carbocyclylthio, heterocarbocyclylthio, arylthio, heteroarylthio, heterocyclylthio, cycloalkylthio, cycloalkenylthio, sulfinyl, sulfamoyl, sulfonyl alkenyl, cyano, or lipid, wherein R6, R6′, R6″, and R6′″ can each be optionally substituted with one or more, the same or different, R10;
- R10 is deuterium, hydroxy, azido, thiol, amino, cyano, halogen, alkyl, alkenyl, alkynyl, carbocyclyl, heterocarbocyclyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkoxy, carbocycloxy, heterocarbocycloxy, aryloxy, heteroaryloxy, heterocyclooxy, cycloalkoxy, cycloalkenoxy, alkylamino, (alkyl)2amino, carbocyclamino, heterocarbocyclamino, arylamino, heteroarylamino, heterocycloamino, cycloalkamino, cycloalkylamino, alkylthio, carbocyclylthio, heterocarbocyclylthio, arylthio, heteroarylthio, heterocyclylthio, cycloalkylthio, cycloalkenylthio, alkenyl, sulfinyl, sulfamoyl, sulfonyl, lipid, nitro, or carbonyl, wherein R10 is optionally substituted with one or more, the same or different, R11;
- R11 is deuterium, hydroxy, azido, thiol, amino, cyano, halogen, alkyl, alkenyl, alkynyl, carbocyclyl, heterocarbocyclyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkoxy, carbocycloxy, heterocarbocycloxy, aryloxy, heteroaryloxy, heterocyclooxy, cycloalkoxy, cycloalkenoxy, alkylamino, (alkyl)2amino, carbocyclamino, heterocarbocyclamino, arylamino, heteroarylamino, heterocycloamino, cycloalkamino, cycloalkylamino, alkylthio, carbocyclylthio, heterocarbocyclylthio, arylthio, heteroarylthio, heterocyclylthio, cycloalkylthio, cycloalkenylthio, alkenyl, sulfinyl, sulfamoyl, sulfonyl, lipid, nitro, or carbonyl;
- and
- Lipid is a C11-C22 higher alkyl, C11-C22 higher alkoxy, polyethylene glycol, or aryl substituted with an alkyl group.
8 more elements
A method of treating or preventing a viral infection in a subject in need thereof, comprising providing to the subject a compound with the structure:
- or a pharmaceutically acceptable salt thereof,
- wherein the viral infection is caused by a Togaviridae, Coronaviridae, Orthomyxoviridae, Pneumoviridae, Arenaviridae, Bunyaviridae, or Picornaviridae family virus.
Dependencies are inferred from the claim text.