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US 2010/0168384 A1Published application
Anti-viral compounds
AssigneeAbbott Laboratories
InventorsKeith F. McDaniel, Dale J. Kempf
Life of this patent
Estimating the term…
Abstract
Compounds capable of inhibiting replication of the hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.
Claims21
A compound of Formula I:
- or a pharmaceutically acceptable salt thereof, wherein:
- D is a five, six or seven membered ring system containing one or two nitrogen and is optionally substituted with one or more R;
- Ra, Rb, Rc, and Rd are each independently selected from hydrogen, halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl-S—, C1-C6alkyl-S(O)—, C1-C6alkyl-S(O)2—, C1-C6alkylamino, C1-C6alkylamide, C1-C6alkylaminoC1-C6alkyl, C1-C6alkylcarbonyl, C1-C6alkylcarbonyloxy, C1-C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkyl-S—C1-C6alkyl, C3-C10carbocycle, C3-C10carbocycle-O—, C7-C14alkylcarbocycle, or 5- to 12-membered heterocycle;
- J is absent, —C(O)—, —O—C(O)—, or —N(A)-C(O)—;
- A is independently selected at each occurrence from (1) hydrogen;
- or (2) C1-C9alkyl, C2-C9alkenyl, C2-C9alkynyl, C1-C9alkoxy, C3-C10carbocycle, C7-C14alkylcarbocycle, or 5-12 membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from cyano, halogen, hydroxy, amino, carboxyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylamino or C1-C6alkylamide;
- with the proviso that A-J- is not —COOH;
- R1 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, or C3-C7carbocycle;
- G is —O—R2, —NH—SO2—R2, or —NH—C(O)—R2, wherein R2 is independently selected at each occurrence from hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8haloalkyl, C3-C14carbocycle optionally substituted with one or more R, C4-C16alkylcarbocycle optionally substituted with one or more R, or 5- to 7-membered heterocycle optionally substituted with one or more R;
- L is C3-C9alkylene, C3-C9alkenylene or C3-C9alkynylene, each of which optionally contains 1 to 3 heteroatoms selected from O, S, S(O) or S(O)2, and L is optionally substituted with one or more substituents independently selected from halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl;
- R4 and R4′ are each independently hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl;
- and
- each R is independently selected at each occurrence from halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl-S—, C1-C6alkylamino, C1-C6alkylaminoC1-C6alkyl, C1-C6alkylcarbonyloxy, C1-C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkyl-S—C1-C6alkyl, C3-C8carbocycle, C6-C16alkylcarbocycle, or 5- to 7-membered heterocycle.
10 more elements
A compound of Formula I:
- or a pharmaceutically acceptable salt thereof, wherein:
- D is a 6- or 7-membered, non-aromatic carbocycle, and is optionally substituted with one or more R;
- Ra, Rb, Rc, and Rd are each independently selected from hydrogen, halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl-S—, C1-C6alkyl-S(O)—, C1-C6alkyl-S(O)2—, C1-C6alkylamino, C1-C6alkylamide, C1-C6alkylaminoC1-C6alkyl, C1-C6alkylcarbonyl, C1-C6alkylcarbonyloxy, C1-C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkyl-S—C1-C6alkyl, C3-C10carbocycle, C3-C10carbocycle-O—, C7-C14alkylcarbocycle, or 5- to to 12-membered heterocycle;
- J is absent, —C(O)—, —O—C(O)—, or —N(A)-C(O)—;
- A is independently selected at each occurrence from (1) hydrogen;
- or (2) C1-C9alkyl, C2-C9alkenyl, C2-C9alkynyl, C1-C9alkoxy, C3-C10carbocycle, C7-C14alkylcarbocycle, or 5-12 membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from cyano, halogen, hydroxy, amino, carboxyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylamino or C1-C6alkylamide;
- with the proviso that A-J- is not —COOH;
- R1 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, or C3-C7carbocycle;
- G is —O—R2, —NH—SO2—R2, or —NH—C(O)—R2, wherein R2 is independently selected at each occurrence from hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8haloalkyl, C3-C14carbocycle optionally substituted with one or more R, C4-C16alkylcarbocycle optionally substituted with one or more R, or 5- to 7-membered heterocycle optionally substituted with one or more R;
- L is C3-C9alkylene, C3-C9alkenylene or C3-C9alkynylene, each of which optionally contains 1 to 3 heteroatoms selected from O, S, S(O) or S(O)2, and L is optionally substituted with one or more substituents independently selected from halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl;
- R4 and R4′ are each independently hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl;
- and
- each R is independently selected at each occurrence from halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl-S—, C1-C6alkylamino, C1-C6alkylaminoC1-C6alkyl, C1-C6alkylcarbonyloxy, C1-C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkoxyC1-C6alkyl, C1-CC6alkyl-S—C1-C6alkyl, C3-C8carbocycle, C6-C16alkylcarbocycle, or 5- to 7-membered heterocycle.
10 more elements
A compound of Formula III:
- or a pharmaceutically acceptable salt thereof, wherein:
- E is a 5-, 6- or 7-membered, non-aromatic ring system containing 0, 1 or 2 heteroatoms selected from nitrogen or oxygen, wherein E is optionally substituted with one or more R;
- Ra, Rb, Rc, and Rd are each independently selected from hydrogen, halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl-S—, C1-C6alkyl-S(O)—, C1-C6alkyl-S(O)2—, C1-C6alkylamino, C1-C6alkylamide, C1-C6alkylaminoC1-C6alkyl, C1-C6alkylcarbonyl, C1-C6alkylcarbonyloxy, C1-C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkyl-S—C1-C6alkyl, C3-C10carbocycle, C3-C10carbocycle-O—, C7-C14alkylcarbocycle, or 5- to to 12-membered heterocycle;
- J is absent, —C(O)—, —O—C(O)—, or —N(A)-C(O)—;
- A is independently selected at each occurrence from (1) hydrogen;
- or (2) C1-C9alkyl, C2-C9alkenyl, C2-C9alkynyl, C1-C9alkoxy, C3-C10carbocycle, C7-C14alkylcarbocycle, or 5-12 membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from cyano, halogen, hydroxy, amino, carboxyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylamino or C1-C6alkylamide;
- with the proviso that A-J- is not —COOH;
- R1 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, or C3-C7carbocycle;
- G is —O—R2, —NH—SO2—R2, or —NH—C(O)—R2, wherein R2 is independently selected at each occurrence from hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8haloalkyl, C3-C14carbocycle optionally substituted with one or more R, C4-C16alkylcarbocycle optionally substituted with one or more R, or 5- to 7-membered heterocycle optionally substituted with one or more R;
- L is C3-C9alkylene, C3-C9alkenylene or C3-C9alkynylene, each of which optionally has from 1 to 3 carbon atoms independently replaced with O, S, S(O) or S(O)2, and L is optionally substituted with one or more substituents independently selected from halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl;
- R4 and R4′ are each independently hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl;
- and
- each R is independently selected at each occurrence from halogen, hydroxy, mercapto, cyano, nitro, amino, carboxyl, formyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl-S—, C1-C6alkylamino, C1-C6alkylaminoC1-C6alkyl, C1-C6alkylcarbonyloxy, C1-C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkyl-S—C1-C6alkyl, C3-C8carbocycle, C6-C16alkylcarbocycle, or 5- to 7-membered heterocycle.
10 more elements
Dependencies are inferred from the claim text.