Spiro[2.4]heptanes for treatment of flaviviridae infections
AssigneeUniversity of Georgia Research Foundation, Inc.
InventorChung K. Chu
Life of this patent
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Abstract
Compounds, methods, and compositions for the treatment of infections in or exposure to humans and other host animals of Flaviviridae viruses, including HCV, that includes the administration of an effective amount of a spiro[2.4]heptane as described herein or a pharmaceutically acceptable salt or prodrug thereof, optionally in a pharmaceutically acceptable carrier, are provided. The spiro[2.4]heptane compounds either possess antiviral activity, or are metabolized to a compound that exhibits such activity.
Claims52
A spiro[2.4]heptane of the structure:
- wherein:
- R1 is a natural or non-natural heteroaryl or heterocyclic moiety;
- R2 is methyl;
- R3 is methyl, F, Cl, N3, or OR7;
- R4 is OR7, methyl, F, Cl, or N3;
- R5 is H, phosphate, a stabilized phosphate prodrug, phosphoramidate, acyl, alkyl, sulfonate ester, a lipid, a phospholipid, an amino acid, a carbohydrate, a peptide, a cholesterol, or other pharmaceutically acceptable leaving group which when administered in vivo is capable of providing a compound wherein R5 is H or mono, di, or tri-phosphate;
- and,
- R7 is H, acyl, phosphate, sulfate, amino acid, peptide, or an oxygen-protecting group;
- or its pharmaceutically acceptable salt.
A spiro[2.4]heptane of the structure:
- wherein:
- R5 is H, phosphate, a stabilized phosphate prodrug, phosphoramidate, acyl, alkyl, sulfonate ester, a lipid, a phospholipid, an amino acid, a carbohydrate, a peptide, a cholesterol, or other pharmaceutically acceptable leaving group which when administered in vivo is capable of providing a compound wherein R5 is H or mono, di, or tri-phosphate;
- B is a natural or non-natural heteroaryl or heterocyclic moiety;
- R6 is methyl;
- R7 is H, acyl, phosphate, sulfate, amino acid, peptide, or an oxygen-protecting group;
- or its pharmaceutically acceptable salt.
A spiro[2.4]heptane of the formula:
- wherein R5 is H, phosphate, a stabilized phosphate prodrug, phosphoramidate, acyl, alkyl, sulfonate ester, a lipid, a phospholipid, an amino acid, a carbohydrate, a peptide, a cholesterol, or other pharmaceutically acceptable leaving group which when administered in vivo is capable of providing a compound wherein R5 is H or mono, di, or tri-phosphate;
- R6 is H;
- R7 is H, acyl, phosphate, sulfate, amino acid, peptide, or an oxygen-protecting group;
- B is a pyrimidine, guanine, xanthine, or hypoxanthine;
- or its pharmaceutically acceptable salt.
A spiro[2.4]heptane of the formula:
- wherein
- R1 is a natural or non-natural heteroaryl or heterocyclic moiety;
- R2 is H and R3 is F;
- R4 is OR7,
- R5 is H, phosphate, a stabilized phosphate prodrug, phosphoramidate, acyl, alkyl, sulfonate ester, a lipid, a phospholipid, an amino acid, a carbohydrate, a peptide, a cholesterol, or other pharmaceutically acceptable leaving group which when administered in vivo is capable of providing a compound wherein R5 is H or mono, di, or tri-phosphate;
- and,
- R7 is H, acyl, phosphate, sulfate, amino acid, peptide, or an oxygen-protecting group;
- or its pharmaceutically acceptable salt.
Dependencies are inferred from the claim text.