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US 2014/0155382 A1Published application
Anti-viral compounds
AssigneeAbbVie Inc.
InventorsDavid A. DEGOEY, Allan C. KRUEGER, Charles W. HUTCHINS, Warren M. KATI, William A. CARROLL
Life of this patent
Estimating the term…
Abstract
Compounds effective in inhibiting replication of 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.
Claims13
A compound of Formula I, or a pharmaceutically acceptable salt thereof,
- wherein:
- A and B are each independently phenyl, and are each independently optionally substituted with one or more RA;
- D is C3-C10carbocycle or 3- to 10-membered heterocycle, and is optionally substituted with one or more RA;
- or D is selected from C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl, and is optionally substituted with one or more substituents selected from halogen, RT, —O—RS, —S—RS, —N(RSRS′), —OC(O)RS, —C(O)ORS, nitro, phosphonoxy, phosphono, oxo, thioxo, formyl or cyano;
- or D is hydrogen or RA;
- X is C(RC) and is optionally substituted with RA or RF;
- one of L1 and L2 is a bond and the other is —(CH2)—, wherein the —(CH2)— is optionally substituted with one or more substituents selected from halogen, RT, —O—RS, —S—RS, —N(RSRS′), —OC(O)RS, C(O)ORS, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl or cyano;
- L3 is bond;
- Y is selected from -T′-C(R1R2)N(R5)-T-RD, -T′-C(R3R4)C(R6R7)-T-RD, -LK-T-RD, or -LK-E;
- R1 and R2 are each independently RC, and R5 is RB;
- or R1 is RC, and R2 and R5, taken together with the atoms to which they are attached, form a 3- to 12-membered heterocyclic ring which is optionally substituted with one or more RA;
- R3, R4, R6, and R7 are each independently RC;
- or R3 and R6 are each independently RC, and R4 and R7, taken together with the atoms to which they are attached, form a 3- to 12-membered carbocyclic or heterocyclic ring which is optionally substituted with one or more RA;
- Z is selected from -T′-C(R8R9)N(R12)-T-RD, -T′-C(R10R11)C(R13R14)-T-RD, -LK-T-RD, or -LK-E;
- R8 and R9 are each independently RC, and R12 is RB;
- or R8 is RC, and R9 and R12, taken together with the atoms to which they are attached, form a 3- to 12-membered heterocyclic ring which is optionally substituted with one or more RA;
- R10, R11, R13, and R14 are each independently RC;
- or R10 and R13 are each independently RC, and R11 and R14, taken together with the atoms to which they are attached, form a 3- to 12-membered carbocyclic or heterocyclic ring which is optionally substituted with one or more RA;
- LK is independently selected at each occurrence from a bond, -LS-N(RB)C(O)-LS′- -LS-C(O)N(RB)-LS′-;
- or C1-C6alkylene, C2-C6alkenylene, or C2-C6alkynylene, each of which is independently optionally substituted at each occurrence with one or more RL;
- or C3-C12carbocycle or 3- to 12-membered heterocycle, each of which is independently optionally substituted at each occurrence with one or more RA;
- E is independently selected at each occurrence from C3-C12carbocycle or 3- to 12-membered heterocycle, and is independently optionally substituted at each occurrence with one or more RA;
- T and T′ are each independently selected at each occurrence from a bond, -LS-, -LS-M-LS′-, -LS-M-LS′-M′-LS″-, wherein M and M′ are each independently selected at each occurrence from a bond, —O—, —S—, —N(RB)—, —C(O)—, —S(O)2—, —S(O)—, —OS(O)—, —OS(O)2—, —S(O)2O—, —S(O)O—, —C(O)O—, —OC(O)—, —OC(O)O—, —C(O)N(RB)—, —N(RB)C(O)—, —N(RB)C(O)O—, —OC(O)N(RB)—, —N(RB)S(O)—, —N(RB)S(O)2—, S(O)N(RB)—, —S(O)2N(RB)—, —C(O)N(RB)C(O)—, —N(RB)C(O)N(RB′)—, N(RB)SO2N(RB′)—, —N(RB)S(O)N(RB′)—, C3-C12carbocycle, or 3- to 12-membered heterocycle, and wherein said C3-C12carbocycle and 3- to 12-membered heterocycle are each independently optionally substituted at each occurrence with one or more RA;
- RA is independently selected at each occurrence from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, -LA, or -LS-RE, wherein two adjacent RA, taken together with the atoms to which they are attached and any atoms between the atoms to which they are attached, can optionally form a carbocycle or a heterocycle;
- RB and RB′ are each independently selected at each occurrence from hydrogen or RE;
- RC is independently selected at each occurrence from hydrogen, halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, or RE;
- RD is each independently selected at each occurrence from hydrogen or RA;
- RE is independently selected at each occurrence from —O—RS, —S—RS, —C(O)RS, —OC(O)RS, —C(O)ORS, —N(RSRS′), —S(O)RS, —SO2RS, —C(O)N(RSRS′), —N(RS)C(O)RS′, —N(RS)C(O)N(RS′RS″), —N(RS)SO2RS′, —SO2N(RSRS′), —N(RS)SO2N(RS′RS″), —N(RS)S(O)N(RS′RS″), —OS(O)—RS, —OS(O)2—RS, —S(O)2ORS, —S(O)ORS, —OC(O)ORS, —N(RS)C(O)ORS′, —OC(O)N(RSRS′), —N(RS)S(O)—RS′, —S(O)N(RSRS′), —C(O)N(RS)C(O)—RS′;
- C1-C6alkyl, C2-C6alkenyl, or C2-C6alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl or cyano;
- or C3-C10-carbocyclyl, or 3- to 10-membered heterocyclyl, wherein said C3-C10carbocyclyl and 3- to 10-membered heterocyclyl are each independently optionally substituted at each occurrence with one or more substituents selected from halogen, RT, —O—RB, —S—RB, —N(RBRB′), —OC(O)RB, —C(O)ORB, nitro, phosphonoxy, phosphono, oxo, thioxo, formyl or cyano;
- RF is independently selected at each occurrence from C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6carbocyclyl, C3-C6carbocyclylC1-C6alkyl, 3- to 6-membered heterocyclyl or (3- or 6-membered heterocyclyl)C1-C6alkyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl or cyano;
- RL is independently selected at each occurrence from halogen, nitro, oxo, phosphonoxy, phosphono, thioxo, cyano, —O—RS, —S—RS, —C(O)RS, —OC(O)RS, —C(O)ORS, —N(RSRS′), —S(O)RS, —SO2RS, —C(O)N(RSRS′), or —N(RS)C(O)RS′;
- or C3-C6carbocycle 3- to 6-membered heterocycle, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, or C2-C6haloalkynyl;
- wherein two adjacent RL, taken together with the atoms to which they are attached and any atoms between the atoms to which they are attached, can optionally form carbocycle or heterocycle;
- LA is independently selected at each occurrence from C1-C6alkyl, C2-C6alkenyl, or C2-C6alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, RT, —O—RS, —S—RS, —N(RSRS′), —OC(O)RS, C(O)ORS, nitro, phosphonoxy, phosphono, oxo, thioxo, formyl or cyano;
- LS, LS′ and LS″ are each independently selected at each occurrence from a bond;
- or C1-C6alkylene, C2-C6alkenylene, or C2-C6alkynylene, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, RT, —O—RS, —S—RS, —N(RSRS′), —OC(O)RS, —C(O)ORS, nitro, phosphonoxy, phosphono, oxo, thioxo, formyl or cyano;
- RS, RS′ and RS″ are each independently selected at each occurrence from hydrogen or RT;
- RT is independently selected at each occurrence from C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6carbocyclyl, C3-C6carbocyclylC1-C6alkyl, 3- to 6-membered heterocyclyl, or (3- or 6-membered heterocyclyl)C1-C6alkyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, RF, —O—RB, —S—RB, —N(RBRB′), —OC(O)RB, —C(O)ORB, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl or cyano.
36 more elements
Dependencies are inferred from the claim text.