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US 2026/0184738 A1Published application
Extended purine tricyclic and bicyclic nucleosides and nucleotides for use as antiviral therapeutics
AssigneeUniversity of Maryland, Baltimore County
InventorKatherine L. RADTKE
Life of this patent
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Abstract
Compounds, methods, and compositions for treating or preventing viral infections using nucleoside compounds. The nucleoside compounds have increased antiviral activity potential with the result of inhibiting at least one of flaviviruses, herpesviruses, polyomaviruses, alphaviruses, enteroviruses, filoviruses matonaviruses, phenuiviruses, Hepatitis B virus, and/or coronaviruses.
Claims18
A nucleoside compound selected from at least one of formula (I) or formula (II):
- wherein
- X1 and X2 are each independently selected from C, O, N, or S;
- X3 is C or N;
- X4 is O, NH, S, or CH2;
- X5 is O, NH, S, or CH2;
- Y1 and Y2 are each independently selected from H, OH, SH, ═O, F, NH2, NH-alkyl, O-alkyl, NH—OH, alkyl, CF3, Cl, CN, or N3;
- Z1 and Z2 are each independently selected from C or a heteroatom;
- R1 is H or cyano;
- R2 and R3 are each independently selected from H, OH, F, Cl, alkyl, ethynyl, or various prodrugs (e.g., amino acid prodrugs);
- R4 is H, OH, N3, or various prodrugs (e.g., amino acid prodrugs);
- R5 is H, F, ethynyl or cyano;
- and
- R6 is H, monophosphate, diphosphate, triphosphate, or various prodrugs (e.g., esters, McGuigan ProTides, lipid phosphates, lipid esters, HepDirect, amino acid prodrugs), or a pharmaceutically acceptable salt, isomer, hydrate, prodrug or solvate thereof;
- and/or formula (III)
- wherein
- X1 and X2 are each independently selected from C, O, N, or S;
- X3 is C or N;
- X4 is O, NH, S, or CH2;
- X5 is O, NH, S, or CH2;
- Y1 is OH, NH2, NH-alkyl, O-alkyl or NH—Ar
- Y2 is NH2, NH-alkyl, O-alkyl or NH—Ar
- R1 is H or cyano;
- R2 and R3 are each independently selected from H, OH, F, Cl, alkyl, ethynyl, or various prodrugs (e.g., amino acid prodrugs);
- R4 is H, OH, N3, or various prodrugs (e.g., amino acid prodrugs);
- R5 is H, F, ethynyl or cyano;
- and
- R6 is H, monophosphate, diphosphate, triphosphate, or various prodrugs (e.g., esters, McGuigan ProTides, lipid phosphates, lipid esters, HepDirect, amino acid prodrugs), or a pharmaceutically acceptable salt, isomer, hydrate, prodrug or solvate thereof,
- or a pharmaceutically acceptable salt, isomer, hydrate, prodrug or solvate thereof.
25 more elements
A nucleoside compound selected from the group consisting of:
- CEM-001:
- 1-[5-(Pyrimidin-6-yl-4-one)imidazol-1-yl]-1-β-D-ribofuranose 2,3,5-Triol (compound 11)
- CEM-002:
- 1-[(5-Hydroxylimidazo[4′,5′:4,5]thieno[3,2-d]pyrimidin-3-yl-7-one)]-β-D-ribofuranose 2,3,5-Triol (compound 16)
- CEM-004:
- 1-[(5-carboxamide)-thieno[2,3-d]imidazol-3-yl]-β-D-ribofuranose 2,3,5-Triol (compound 6)
- CEM-007:
- 1-[(5,7-diaminoimidazo-[4′,5′:4,5]thieno[3,2-d]pyrimidin-3-yl)]-β-D-ribofuranose-2,3,5-Triol (compound 21)
- CEM-009:
- Nucleoside prodrug (compound 19)
- CEM-010:
- Nucleoside prodrug (compound 14)
- CEM-011:
- Nucleoside prodrug (compound 24a)
- CEM-012:
- Nucleoside prodrug (compound 29)
- CEM-015:
- Nucleoside prodrug (compound 9)
- CEM-021:
- 1-[(5-Aminoimidazo[4′,5′:4,5]thieno[3,2-d]pyrimidin-3-yl-7-one)]-β-D-ribofuranose 2,3,5-Triol
- CEM-024:
- 2′-deoxy-2′-fluoro-2′-C-methyl-1′-[(5,7-diaminoimidazo-[4′,5′:4,5]thieno[3,2-d]pyrimidin-3-yl)]-β-D-ribofuranose (compound 34)
- CEM-028:
- 1-[(5,7-dimethoxyimidazo-[4′,5′:4,5]thieno[3,2-d]pyrimidin-3-yl)]-β-D-ribofuranose-2,3,5-Triol
- CEM-033:
- Nucleoside prodrug
- CEM-036:
- Nucleoside prodrug
- CEM-038:
- Trisphosphate compound (compound 38)
- CEM-041:
- Nucleoside prodrug (compound 35a)
- CEM-042:
- Nucleoside prodrug (compound 36a)
- CEM-051:
- Trisphosphate compound (compound 39)
- CEM-052:
- Nucleoside prodrug (compound 35b)
- CEM-053:
- Nucleoside prodrug (compound 36b)
- CEM-054:
- Nucleoside prodrug (compound 37a)
- CEM-055:
- Nucleoside prodrug (compound 37b)
- CEM-056:
- Nucleoside prodrug (compound 24b)
- or a pharmaceutically acceptable salt, isomer, hydrate, prodrug or solvate thereof.
44 more elements
Dependencies are inferred from the claim text.