Anti-viral compounds

A compound of Formula (XIII) or pharmaceutically acceptable salts thereof:

• wherein
• m and n are independently 0, 1, or 2;
• q and s are independently 0, 1, 2, 3, or 4;
• u and v are independently 0, 1, 2, or 3;
• A and B are selected from phenyl and a six-membered heteroaromatic ring containing one, two, or three nitrogen atoms;
• provided that at least one of A and B is other than phenyl;
• wherein at least one of A or B is substituted with -L-E or -L3-D as defined below;
• X is selected from O, S, S(O), SO2, CH2, CHR5, and C(R5)2;
• provided that when n is 0, X is selected from CH2, CHR5, and C(R5)2;
• Y is selected from O, S, S(O), SO2, CH2, CHR6, and C(R6)2;
• provided that when m is 0, Y is selected from CH2, CHR6, and C(R6)2;
• each R1 and R2 is independently selected from alkoxy, alkoxyalkyl, alkoxycarbonyl, alkyl, arylalkoxycarbonyl, carboxy, formyl, halo, haloalkyl, hydroxy, hydroxyalkyl, —NRaRb, (NRaRb)alkyl, and (NRaRb)carbonyl;
• wherein at least one of R1 and R2 can be optionally substituted with -L-E or -L3-D as defined below;
• R3 and R4 are each independently selected from hydrogen, R9—C(O)—, and R9—C(S)—;
• each R5 and R6 is independently selected from alkoxy, alkyl, aryl, halo, haloalkyl, hydroxy, and —NRaRb, wherein the alkyl can optionally form a fused three- to six-membered ring with an adjacent carbon atom, wherein the three- to six-membered ring is optionally substituted with one or two alkyl groups;
• R7 and R8 are each independently selected from hydrogen;
• alkoxycarbonyl, alkyl, arylalkoxycarbonyl, carboxy, haloalkyl, (NRaRb)carbonyl, and trialkylsilylalkoxyalkyl;
• and
• each R9 is independently selected from alkoxy, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylcarbonylalkyl, aryl, arylalkenyl, arylalkoxy, arylalkyl, aryloxyalkyl, cycloalkyl, (cycloalkyl)alkenyl, (cycloalkyl)alkyl, cycloalkyloxyalkyl, haloalkyl, heterocyclyl, heterocyclylalkenyl, heterocyclylalkoxy, heterocyclylalkyl, heterocyclyloxyalkyl, hydroxyalkyl, —NRcRd, (NRcRd)alkenyl, (NRcRd)alkyl, and (NRcRd)carbonyl,
• -L-E or -L3-D are as follows:
• E is (i) C3-C14-carbocycle or 3- to 14-membered heterocycle, and is optionally substituted with one or more RA;
• or (ii) E is -LS-RE;
• L is -LS-, -LS-O-LS′-, -LS-S(O)2-LS′-, -LS-OS(O)2-LS′-, -LS-S(O)2O-LS′-, -LS-OS(O)-LS′-, -LS-S(O)O-LS′-, -LS-C(O)O-LS′-, -LS-OC(O)-LS′-, -LS-OC(O)O-LS′-, -LS-C(O)N(RB)-LS′-, -LS-N(RB)C(O)-LS′-, -LS-C(O)N(RB)O-LS′-, -LS-N(RB′)C(O)O-LS′-, -LS-OC(O)N(RB)-LS′-, -LS-C(O)N(RB)N(RB′)-LS′-, -LS-S-LS′-, -LS-C(S)-LS′-, -LS-C(S)O-LS′-, -LS-OC(S)-LS′-, -LS-C(S)N(RB)-LS′-, -LS-N(RB)-LS′-, -LS-N(RB)C(S)-LS′-, -LS-N(RB)S(O)-LS′-, -LS-N(RB)S(O)2-LS′-, -LS-S(O)2N(RB)-LS′-, -LS-S(O)N(RB′)-LS′-, -LS-LS-C(S)N(RB)O-LS′-, -LS-C(O)N(RB)C(O)-LS′-, -LS-N(RB)C(O)N(RB′)-LS′-, -LS-N(RB)SO2N(RB′)-LS′-, -LS-N(RB)S(O)N(RB′)-LS′-, or -LS-C(S)N(RB)N(RB′)-LS′-;
• LS and LS′ are each independently selected at each occurrence from bond;
• or C1-C6alkylene, C2-C6 alkenylene or C2-C6 alkynylene, each of which is independently optionally substituted at each occurrence with one or more RL;
• RA is independently selected at each occurrence from halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphonoxy, or phosphono;
• or -LS-RE;
• RB and RB′ are each independently selected at each occurrence from hydrogen;
• or C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, 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, C3-C6 carbocycle or 3- to 6-membered heterocycle;
• or C3-C6-carbocycle or 3- to 6-membered heterocycle;
• wherein each C3-C6-carbocycle or 3- to 6-membered heterocycle in RB or RB′ 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-C6 haloalkyl, C2-C6haloalkenyl or C2-C6haloalkynyl;
• 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′) or —C(O)N(RS)C(O)—RS′;
• or C1-C6 alkyl, C2-C6 alkenyl 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-C6-carbocycle or 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-C6 alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6 haloalkyl, C2-C6haloalkenyl or C2-C6haloalkynyl;
• 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-C6-carbocycle 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-C6 alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6haloalkenyl or C2-C6 haloalkynyl;
• RS, RS′ and RS″ are each independently selected at each occurrence from hydrogen;
• C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, 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 or 3- to 6-membered carbocycle or heterocycle;
• or 3- to 6-membered carbocycle or heterocycle;
• wherein each 3- to 6-membered carbocycle or heterocycle in RS, RS′ or RS′ 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-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6haloalkenyl or C2-C6haloalkynyl;
• L3 is bond or -LS-K-LS′-, wherein K is selected from 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′)—, or —N(RB)S(O)N(RB′)—;
• D is C3-C12 carbocycle or 3- to 12-membered heterocycle, and is optionally substituted with one or more RA;
• or D is C3-C12-carbocycle or 3- to 12-membered heterocycle which is substituted with J and optionally substituted with one or more RA, where J is C3-C12 carbocycle or 3- to 12-membered heterocycle and is optionally substituted with one or more RA, or J is SF5;
• or D is hydrogen or RA;
• RA is independently selected at each occurrence from halogen, nitro, oxo, phosphonoxy, phosphono, thioxo, cyano, 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 carbocycle or heterocycle;
• RB and RB′ are each independently selected at each occurrence from hydrogen;
• or C1-C6alkyl, C2-C6 alkenyl or C2-C6 alkynyl, 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 or 3- to 6-membered carbocycle or heterocycle;
• or 3- to 6-membered carbocycle or heterocycle;
• wherein each 3- to 6-membered carbocycle or heterocycle in RB or RB′ 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, Cr C6haloalkyl, C2-C6haloalkenyl or C2-C6haloalkynyl;
• 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′), —P(O)(ORS)2, or —C(O)N(RS)C(O)—RS′;
• or 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-C6 carbocycle or 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-C6 alkyl, C2-C6 alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C(O)ORS, or —N(RSRS′);
• 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-C6-carbocycle 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-C6 alkyl, C2-C6 alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6 haloalkenyl or C2-C6 haloalkynyl;
• 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;
• LS and LS′ are each independently selected at each occurrence from bond;
• or C1-C6alkylene, C2-C6alkenylene or C2-C6alkynylene, each of which is independently optionally substituted at each occurrence with one or more RL;
• and
• RS, RS′ and RS″ are each independently selected at each occurrence from hydrogen;
• C1-C6 alkyl, C2-C6 alkenyl 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, cyano, —O—C1-C6 alkyl, —O—C1-C6 alkylene-O—C1-C6 alkyl, or 3- to 6-membered carbocycle or heterocycle;
• or 3- to 6-membered carbocycle or heterocycle;
• wherein each 3- to 6-membered carbocycle or heterocycle in RS, RS′ or RS′ 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-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl or C2-C6 haloalkynyl.