Compounds, methods and compositions useful for the treatment of bovine viral diarrhea virus (BVDV) infection and hepatitis C virus (HCV) infection
OwnerChristine C. Dykstra, Maurice Daniel Givens +7inventors
InventorsChristine C. Dykstra, Maurice Daniel Givens, David A. Stringfellow, Kenny Brock, David Boykin, Arvind Kumar, W. David Wilson, Richard R. Tidwell, Chad E. Stephens
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Abstract
The present invention relates to novel compounds and methods that are useful in treating members of the Flaviviridae family of viruses. Compounds of the present invention will have a structure according to Formulas (I)-(VI) as recited throughout the application.
Claims106
A compound according to Formula I:
- 10
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 11
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl.
A compound according to Formula II:
- 18
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 19
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl.
A compound according to Formula III:
- 20
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 21
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halo, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl.
A compound according to Formula IV:
- 22
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 23
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl.
A compound according to Formula V:
- 24
- wherein:
- X1 is independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2is CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 25
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl.
A compound according to Formula VI:
- 28
- wherein:
- X1 is selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 is CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 29
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl.
A method of treating bovine viral diarrhea virus (BVDV) infection in a subject in need of such treatment, comprising administering to the subject a compound selected from the group consisting of Formula I and Formula II:
- 41
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 42
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof, in an amount sufficient to treat the bovine viral diarrhea virus (BVDV) infection.
A method of treating bovine viral diarrhea virus (BVDV) infection in a subject in need of such treatment, comprising administering to the subject a compound selected from the group consisting of Formula III and Formula IV:
- 44
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 45
- R1, R2, R3, R4, and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof, in an amount sufficient to treat the bovine viral diarrhea virus (BVDV) infection.
A method of treating bovine viral diarrhea virus (BVDV) infection in a subject in need of such treatment, comprising administering to the subject a compound selected from the group consisting of Formula V and Formula VI:
- 46
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 47
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof, in an amount sufficient to treat the bovine viral diarrhea virus (BVDV) infection.
A method of treating hepatitis C infection in a subject in need of such treatment, comprising administering to the subject a compound selected from the group consisting of Formula I and Formula II:
- 60
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 61
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof, in an amount sufficient to treat the hepatitis C infection.
A method of treating hepatitis C infection in a subject in need of such treatment, comprising administering to the subject a compound selected from the group consisting of Formula III and Formula IV:
- 63
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 64
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof, in an amount sufficient to treat the hepatitis C infection.
A method of treating hepatitis C infection in a subject in need of such treatment, comprising administering to the subject a compound selected from the group consisting of Formula V and Formula VI:
- 65
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 66
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof, in an amount sufficient to treat the hepatitis C infection.
A method of treating a member of the Flaviviridae family of viruses in a subject in need of such treatment, comprising administering to the subject a compound selected from the group consisting of Formula I and Formula II:
- 79
- wherein:
- X1 and X3 are each independently selected from the group consisting of O, S and NR9, wherein R9 is H or alkyl;
- X2 and X4 are each independently CH or N;
- A is selected from the group consisting of H, alkyl, aryl,
- 80
- R1, R2, R3, R4 and R5 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, alkylhalide, amidine, nitro and amino groups;
- R6 is H, alkyl or aryl;
- and
- R7 and R8 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof, in an amount sufficient to treat the bovine viral diarrhea virus (BVDV) infection.
Dependencies are inferred from the claim text.