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US 2012/0071434 A1Published application
Substituted nucleotide analogs
AssigneeAlios BioPharma, Inc.
InventorsDavid Bernard Smith, Jerome Deval, Natalia Dyatkina, Leonid Beigelman, Guangyi Wang
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Abstract
Disclosed herein are phosphorothioate nucleotide analogs, methods of synthesizing phosphorothioate nucleotide analogs and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the phosphorothioate nucleotide analogs.
Claims51
A compound of Formula (I) or a pharmaceutically acceptable salt thereof:
- wherein:
- B1 is an optionally substituted heterocyclic base or an optionally substituted heterocyclic base with a protected amino group;
- R1 is selected from the group consisting of O−, OH, an optionally substituted N-linked amino acid and an optionally substituted N-linked amino acid ester derivative;
- R2 is selected from the group consisting of an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl and
- wherein R19, R20 and R21 are independently absent or hydrogen, and n is 0 or 1;
- provided that when R1 is O− or OH, then R2 is
- R3a and R3b are independently selected from the group consisting of hydrogen, deuterium, an optionally substituted C1-6 alkyl, an optionally substituted C2-6 alkenyl, an optionally substituted C2-6 alkynyl, an optionally substituted C1-6 haloalkyl and aryl(C1-6 alkyl);
- or R3a and R3b are taken together to form an optionally substituted C3-6 cycloalkyl;
- R4 is selected from the group consisting of hydrogen, azido, an optionally substituted C1-6 alkyl, an optionally substituted C2-6 alkenyl and an optionally substituted C2-6 alkynyl;
- R5 is selected from the group consisting of hydrogen, halogen, azido, cyano, an optionally substituted C1-6 alkyl, —OR10 and —OC(═O)R11;
- R6 is selected from the group consisting of hydrogen, halogen, azido, cyano, an optionally substituted C1-6 alkyl, —OR12 and —OC(═O)R13;
- R7 is selected from the group consisting of hydrogen, halogen, azido, cyano, an optionally substituted C1-6 alkyl, —OR14 and —OC(═O)R15;
- or R6 and R7 are both oxygen atoms and linked together by a carbonyl group;
- R8 is selected from the group consisting of hydrogen, halogen, azido, cyano, an optionally substituted C1-6 alkyl, —OR16 and —OC(═O)R17;
- R9 is selected from the group consisting of hydrogen, azido, cyano, an optionally substituted C1-6 alkyl and —OR18;
- R10, R12, R14, R16 and R18 are independently selected from the group consisting of hydrogen and an optionally substituted C1-6 alkyl;
- and
- R11, R13, R15 and R17 are independently selected from the group consisting of an optionally substituted C1-6 alkyl and an optionally substituted C3-6 cycloalkyl;
- with the proviso that when R3a, R3b, R4, R5, R7, R8 and R9 are all hydrogen, then R6 is not azido.
16 more elements
Dependencies are inferred from the claim text.