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Details for Patent: 9,090,661

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Details for Patent: 9,090,661

Title:Inhibitors of hepatitis C virus replication
Abstract: The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system. ##STR00001##
Inventor(s): Coburn; Craig A. (San Rafael, CA), McCauley; John A. (Maple Glen, PA), Ludmerer; Steven W. (North Wales, PA), Liu; Kun (Boston, MA), Vacca; Joseph P. (Telford, PA), Wu; Hao (Shanghai, CN), Hu; Bin (Shanghai, CN), Soll; Richard (San Diego, CA), Sun; Fei (Shanghai, CN), Wang; Xinghai (Shanghai, CN), Yan; Man (Shanghai, CN), Zhang; Chengren (Shanghai, CN), Zheng; Mingwei (Shanghai, CN), Zhong; Bin (Shanghai, CN), Zhu; Jian (Shanghai, CN)
Assignee: Merck Sharp & Dohme Corp. (Rahway, NJ)
Filing Date:Aug 29, 2014
Application Number:14/473,117
Claims:1. A compound having structural formula (I): ##STR00569## and/or a pharmaceutically acceptable salt thereof, wherein: ##STR00570## is ##STR00571## which is substituted by u substituents R.sup.1, each R.sup.1 is independently chosen from the group consisting of hydrogen, halogen, --OR.sup.3a, --CN, --(CH.sub.2).sub.0-6C(O)R.sup.3, --CO.sub.2R.sup.3a, --C(O)N(R.sup.3a).sub.2, --SR.sup.3a, --S(O)R.sup.3a, --S(O)R.sup.3a, --(CH.sub.2).sub.0-6N(R.sup.3a).sub.2, --N(R.sup.3a)SO.sub.2R.sup.3a, --N(R.sup.3a)CO.sub.2R.sup.3a, --N(R.sup.3a)C(O)R.sup.3, --N(R.sup.3a)COR.sup.3a, --N(R.sup.3a)C(O)N(R.sup.3a), C.sub.1-6alkyl, C.sub.3-8carbocycle containing from 0 to 3 heteroatoms chosen from N, O and S, and phenyl, and the C.sub.1-6alkyl, C.sub.3-8carbocycle and phenyl are substituted by from 0 to 3 substitutents independently chosen from the group consisting of hydrogen, halogen, --OR.sup.3a, --CN, --CO.sub.2R.sup.3a, --C(O)N(R.sup.3a).sub.2, --N(R.sup.3a).sub.2, --N(R.sup.3a)CO.sub.2R.sup.3a, --SR.sup.3a, --S(O)R.sup.3a, --S(O.sub.2)R.sup.3a, --N(R.sup.3a)SO.sub.2R.sup.3a, --N(R.sup.3a)CO.sub.2R.sup.3a, --N(R.sup.3a)C(O)N(R.sup.3a), C.sub.1-6alkyl, --O--C.sub.1-6alkyl, --S--C.sub.1-6alkyl, and C.sub.3-8cycloalkyl, u is from 0 to 4, each R.sup.3 is independently chosen from the group consisting of hydrogen, C.sub.1-6alkyl, --OH, --O--C.sub.1-6alkyl and C.sub.3-8cycloalkyl, and each R.sup.3a is independently chosen from the group consisting of hydrogen, C.sub.1-6alkyl and C.sub.3-8cycloalkyl; ##STR00572## is phenyl, which is substituted by v substituents R.sup.2, each R.sup.2 is independently chosen from the group consisting of hydrogen, halogen, --OR.sup.4a, --CN, --CO.sub.2R.sup.4a, --C(O)R.sup.4a, --C(O)N(R.sup.4a).sub.2 --N(R.sup.4a).sub.2, --N(R.sup.4a)COR.sup.4, --N(R.sup.4a)CO.sub.2R.sup.4a, --N(R.sup.4a)C(O)N(R.sup.4a), --N(R.sup.4a)SO.sub.2R.sup.4a, --SR.sup.4a, --S(O)R.sup.4a, --S(O.sub.2)R.sup.4a, C.sub.1-6alkyl substituted by from 0 to 4 R.sup.4 and C.sub.3-8cycloalkyl substituted by from 0 to 4 R.sup.4, v is from 0 to 4, each R.sup.4 is independently chosen from the group consisting of hydrogen, --OH, C.sub.1-6alkyl and C.sub.3-8cycloalkyl; each R.sup.4a is independently chosen from the group consisting of hydrogen, C.sub.1-6alkyl and C.sub.3-8cycloalkyl; each D is independently a 5- or 6-membered aryl ring system D' containing from 0 to 4 heteroatoms independently chosen from the group consisting of N, O and S, and substituted on C or N atoms by from 0 to 2 substituents R.sup.5, each R.sup.5 is independently chosen from the group consisting of hydrogen, halogen, --OR.sup.6, --CN, --CO.sub.2R.sup.6, --C(O)N(R.sup.6).sub.2, --N(R.sup.6).sub.2, --N(R.sup.6)COR.sup.6, --SR.sup.6, --S(O)R.sup.6, --S(O.sub.2)R.sup.6, --N(R.sup.6)SO.sub.2R.sup.6, --NCO.sub.2R.sup.6, --NC(O)N(R.sup.6).sub.2, C.sub.1-6alkyl substituted by from 0 to 3 R.sup.6 and C.sub.3-8cycloalkyl substituted by from 0 to 3 R.sup.6, and each R.sup.6 is independently chosen from the group consisting of hydrogen, C.sub.1-6alkyl and C.sub.3-8cycloalkyl; each E is a pyrrolidinyl derivative chosen from the group consisting of: ##STR00573## I is a bivalent group chosen from --C(O)--, --CO.sub.2-- and --C(O)N(R.sup.7)--, J is a fused ring system chosen from the group consisting of 3- to 7-membered carbocycles and 5- or 6-membered aryl rings containing from 0 to 4 heteroatoms independently chosen from the group consisting of N, O and S, and substituted on C or N atoms by substituents R.sup.9, each R.sup.8a is independently chosen from the group consisting of hydrogen, halogen, --OH, --OC.sub.1-6alkyl and C.sub.1-6alkyl, or two R.sup.8a may be taken together to form oxo, each R.sup.8b is independently chosen from the group consisting of hydrogen, halogen, --OH, --OC.sub.1-6alkyl and C.sub.1-6alkyl, or two R.sup.8b may be taken together to form oxo, each R.sup.8c is independently chosen from the group consisting of hydrogen and C.sub.1-6alkyl, or any two groups selected from R.sup.8a, R.sup.8b and R.sup.8c may be taken together to form a spiro-bicyclic or bridged bicyclic ring; each R.sup.9 is independently chosen from the group consisting of hydrogen, halogen, C.sub.1-6alkyl, --O--C.sub.1-6alkyl, --S--C.sub.1-6alkyl, --NH--C.sub.1-6alkyl and --NHC(O)--C.sub.1-6alkyl; and each G is independently chosen from the group consisting of: (a) hydrogen, (b) --OR.sup.10a, (c) --CN, (d) --CO.sub.2R.sup.10a, (e) --C(O)N(R.sup.10).sub.2, (f) --SR.sup.10a, (g) --S(O)R.sup.10a, (h) --S(O.sub.2)R.sup.10a, (i) --N(R.sup.10).sub.2, (j) --N(R.sup.10)SO.sub.2R.sup.10a, (k) --NCO.sub.2R.sup.10a, (l) --NC(O)N(R.sup.10).sub.2, (m) C.sub.1-6alkyl having 0 to 4 substituents R.sup.11, each R.sup.11 is independently chosen from the group consisting of: (i) --OH, (ii) --N(R.sup.10).sub.2, (iii) .dbd.NR.sup.10, (iv) --O --C.sub.1-6alkyl, (v) --C(O)R.sup.10, (vi) --S--C.sub.1-6alkyl, (vii) --SO.sub.2--C.sub.1-6alkyl, (viii) 3- to 8-membered carbocycles containing from 0 to 3 heteroatoms independently chosen from the group consisting of N, O and S, and having from 0 to 3 substitutents R.sup.12 on N or C atoms, and each R.sup.12 is independently selected from the group consisting of hydrogen, halogen, C.sub.1-6alkyl having from 0 to 3 substituents chosen from R.sup.10, --O--C.sub.1-6alkyl, --S--C.sub.1-6alkyl, --OR.sup.10a, --CN, --C(O)R.sup.10, --CO.sub.2R.sup.10a, --C(O)N(R.sup.10).sub.2, --SR.sup.10a, --S(O)R.sup.10a, --S(O.sub.2)R.sup.10a, --N(R.sup.10)SO.sub.2R.sup.10a, --NCO.sub.2R.sup.10a, --NC(O)N(R.sup.10).sub.2 and --N(R.sup.10).sub.2, or two R.sup.12 are taken together to form oxo, and (ix) 5- or 6-membered aryl containing from 0 to 3 heteroatoms independently chosen from the group consisting of N, O and S, and having from 0 to 3 substitutents R.sup.13 on N or C atoms, and each R.sup.13 is independently selected from the group consisting of hydrogen, halogen, C.sub.1-6alkyl, --O--C.sub.1-6alkyl and 3- to 8-membered carbocycles containing from 0 to 3 heteroatoms independently chosen from the group consisting of N, O and S, (n) 3- to 8-membered carbocycles containing from 0 to 3 heteroatoms independently chosen from the group consisting of N, O and S, and having from 0 to 3 substitutents R.sup.10 on N or C atoms; and (o) aryl ring systems G' chosen from the group consisting of: (i) 5- to 7-membered monocyclic ring systems and (ii) 8- to 10-membered bicyclic ring systems, and the aryl ring systems G' containing from 0 to 4 heteroatoms independently chosen from the group consisting of N, O and S, and substituted on C or N atoms by 0 to 3 substitutents R.sup.10; each R.sup.10 is independently chosen from the group consisting of (i) hydrogen, (ii) --CN, (iii) C.sub.1-6alkyl, (iv) --O--C.sub.0-6alkyl, (v) --S--C.sub.0-6alkyl, (vi) C.sub.1-6alkyl-O--R.sup.14, (vii) --C(O)R.sup.14, (viii) --CO.sub.2R.sup.14, (ix) --SO.sub.2R.sup.14, (x) --N(R.sup.14).sub.2, (xi) --N(R.sup.14)SO.sub.2R.sup.14, (xii) --NCO.sub.2R.sup.14, (xiii) --NC(O)N(R.sup.14).sub.2, and (xiv) 3- to 8-membered carbocycles containing from 0 to 3 heteroatoms independently chosen from the group consisting of N, O and S, or two R.sup.10 may be taken together to form oxo; each R.sup.10a is independently chosen from the group consisting of (i) hydrogen, (ii) --CN, (iii) C.sub.1-6alkyl, (iv) C.sub.1-6alkyl-O--R.sup.14, (v) --C(O)R.sup.14, (vi) --CO.sub.2R.sup.14, (vii) --SO.sub.2R.sup.14, (x) --N(R.sup.14).sub.2, (xi) --N(R.sup.14)SO.sub.2R.sup.14, (xii) --NCO.sub.2R.sup.14, (xiii) --NC(O)N(R.sup.14).sub.2, and (xiv) 3- to 8-membered carbocycles containing from 0 to 3 heteroatoms independently chosen from the group consisting of N, O and S, and two R.sup.10 or R.sup.10a groups can be taken together with the N to which they are attached to form a ring, which may be substituted by from 0 to 3 substituents R.sup.14, and each R.sup.14 is independently chosen from the group consisting of hydrogen, C.sub.1-6alkyl, C.sub.3-8cycloalkyl, --(CH.sub.2).sub.0-3C.sub.3-8cycloalkyl and phenyl.

2. The compound according to claim 1, wherein each R.sup.1 is chosen from the group consisting of hydrogen, fluorine and --CN.

3. The compound according to claim 1, wherein v is from 0 to 4, each R.sup.2 is independently chosen from the group consisting of hydrogen, halogen, --OR.sup.4a, --CN, --CO.sub.2R.sup.4a, --C(O)N(R.sup.4a).sub.2, --N(R.sup.4a).sub.2, --N(R.sup.4a)CO.sub.2R.sup.4a, --SR.sup.4a, --S(O)R.sup.4a, --S(O.sub.2)R.sup.4a, --N(R.sup.4a)SO.sub.2R.sup.4a, --N(R.sup.4a)CO.sub.2R.sup.4a, --N(R.sup.4a)C(O)N(R.sup.4a), C.sub.1-6alkyl substituted by from 0 to 4 R.sup.4 and C.sub.3-8cycloalkyl substituted by from 0 to 4 R.sup.4, each R.sup.4 is independently chosen from the group consisting of hydrogen, --OH, C.sub.1-6alkyl and C.sub.3-8cycloalkyl, and each R.sup.4a is independently chosen from the group consisting of hydrogen, C.sub.1-6alkyl and C.sub.3-8cycloalkyl.

4. The compound according to claim 1, wherein each D is independently chosen from the group consisting of ##STR00574##

5. The compound according to claim 1, wherein each E is independently chosen from the group consisting of ##STR00575## where one of R.sup.8a and R.sup.8b is --OH or fluorine.

6. The compound according to claim 1, wherein each G is independently chosen from the group consisting of (a) hydrogen, (b) --CN, (c) C.sub.1-5alkyl having 1 to 3 substituents R.sup.11, each R.sup.11 is independently chosen from the group consisting of --OH, --NH.sub.2, --NCH.sub.3H, --N(CH.sub.3).sub.2, --N(CH.sub.2CH.sub.3).sub.2, .dbd.NH, .dbd.NCH.sub.3, --C(O)H, --C(O)OH, --C(O)CH.sub.3, --C(O)OCH.sub.3, --NHC(O)H, --NHC(O)OH, --NHC(O)CH.sub.3, --NHC(O)OCH.sub.3, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyranyl, pyrrolidinyl, piperidinyl, oxacyclopentyl, and oxacyclohexyl, phenyl, pyridinyl, pyrimidinyl and pyrrolyl, where the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyranyl, pyrrolidinyl, piperidinyl, oxacyclopentyl and oxacyclohexyl are substituted by from 0 to 2 substitutents R.sup.12 on N or C atoms, and each R.sup.12 is independently selected from the group consisting of hydrogen, halogen, carboxy, C.sub.1-6alkyl, --O--C.sub.1-6alkyl and --S--C.sub.1-6alkyl; and the phenyl, pyridinyl, pyrimidinyl and pyrrolyl are substituted by from 0 to 3 substitutents R.sup.13 on N or C atoms, and each R.sup.13 is independently selected from the group consisting of hydrogen, halogen, C.sub.1-6alkyl and 3- to 8-membered cycloalkyl containing from 0 to 3 heteroatoms independently chosen from the group consisting of N, O and S, (d) cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyranyl, pyrrolidinyl, piperidinyl, oxacyclopentyl and oxacyclohexyl having from 0 to 3 substitutents R.sup.10 on N or C atoms, said R.sup.10 independently selected from the group consisting of hydrogen, halogen, carboxy, C.sub.1-6alkyl, --O--C.sub.1-6alkyl, --S--C.sub.1-6alkyl, phenyl and benzyl, and (e) aryl ring systems G' chosen from the group consisting of: phenyl, pyridinyl and 9-membered bicyclic ring systems containing from 0 to 2 heteroatoms independently chosen from the group consisting of N and O.

7. The compound according to claim 1, wherein said ##STR00576## is ##STR00577## where said ##STR00578## is substituted by from 0 to 3 additional R.sup.1; v is from 0 to 2; each R.sup.2 is independently chosen from the group consisting of fluorine, chlorine, --OH, --CH.sub.3, --OCH.sub.3 and --CN; each D is independently chosen from the group consisting of ##STR00579## each E is independently chosen from the group consisting of ##STR00580## where one of R.sup.8a and R.sup.8b is --OH or fluorine; and each G is independently chosen from the group consisting of C.sub.1-4alkyl having 1 to 2 substituents R.sup.11, wherein each R.sup.11 is independently chosen from the group consisting of --OH, --NH.sub.2, --NCH.sub.3H, --N(CH.sub.3).sub.2, --N(CH.sub.2CH.sub.3).sub.2, --C(O)OCH.sub.3, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyranyl, pyrrolidinyl, piperidinyl, oxacyclopentyl, oxacyclohexyl, phenyl, pyridinyl, pyrimidinyl and pyrrolyl.

8. The compound according to according to claim 1, wherein the compound having structural formula (I) is a compound having structural formula (Ib): ##STR00581## or a pharmaceutically acceptable salt thereof, wherein said ##STR00582## is substituted by u substituents R.sup.1, and Y is O.

9. The compound according to according to claim 8, wherein said ##STR00583## is substituted by u substituents R.sup.1, Y is O, and both instances of G are ##STR00584##

10. The compound according to according to claim 1, wherein the compound having structural formula (I) is a compound having structural formula (Ib): ##STR00585## or a pharmaceutically acceptable salt thereof, wherein said ##STR00586## is substituted by u substituents R.sup.1, Y is O, and both instances of G are ##STR00587##

11. A compound according to claim 1, chosen from the group consisting of: propan-2-yl[(1R)-2-{(2S)-2-[(4-{3-bromo-5-[({(2S)-1-[(2R)-2-phenyl-2-{[(p- ropan-2-yloxy)carbamonyl]amino}acetyl]pyrrolidin-2-yl}carbonyl)amino]-1-be- nzofuran-2-yl}phenyl)carbamoyl]pyrrolidin-1-yl}-2-oxo-1-phenylethyl]carbam- ate; (2S)-N-(4-{3-bromo-5-[({(2S)-1-[(2R)-2-(dimethylamino)-2-phenylacetyl- ]pyrrolidin-2-yl}carbonyl)amino]-1-benzofuran-2-yl}phenyl)-1-[(2R)-2-(dime- thylamino)-2-phenylacetyl]pyrrolidine-2-carboxamide; methyl{(1R)-2-[(2S)-2-({4-[3-bromo-5-({[(2S)-1-{(2R)-2-[(methoxycarbonyl)- amino]-2-phenylacetyl}pyrrolidin-2-yl]carbonyl}amino)-1-benzofuran-2-yl]ph- enyl}carbamoyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate; methyl{(2S)-1-[(2S)-2-({4-[3-fluoro-5-({[(2S)-1-{(2S)-2-[(methoxycarbonyl- )amino]-3-methylbutanoyl}pyrrolidin-2-yl]carbonyl}amino)-1H-indol-2-yl]phe- nyl}carbamoyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate; N-{2-[4-(acetylamino)phenyl]-3-bromo-1-benzofuran-5-yl}-1-[(2R)-2-(dimeth- ylamino)-2-phenylacetyl]-L-prolinamide; tert-butyl {(1S)-2-[(2S)-2-({4-[3-bromo-5-({[(2S)-1-{(2S)-2-[(tert-butoxycarbonyl)am- ino]-2-phenylacetyl}pyrrolidin-2-yl]carbonyl}amino)-1-benzofuran-2-yl]phen- yl}carbamoyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate); (2S)-N-{4-[3-bromo-5-({[(2S)-1-phenylacetyl)pyrrolidin-2-yl]carbonyl}amin- o)-1-benzofuran-2-yl]phenyl}-1-(phenylacetyl)pyrrolidine-2-carboxamide; tert-butyl{(1R)-2-[(2S)-2-({4-[3-bromo-5-({[(2S)-1-{(2R)-2-[(tert-butoxyc- arbonyl)amino]-2-phenylacetyl}pyrrolidin-2-yl]carbonyl}amino)-1-benzofuran- -2-yl]phenyl}carbamoyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate; methyl{(2S)-1-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S)-2-[(methoxy-carbonyl)amin- o]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-2-yl)p- henyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamat- e; (2R)-2-(diethylamino)-1-[(2S)-2-(5-{4-[5-(2-{(2S)-1-[(2R)-2-(diethylami- no)-2-phenylacetyl]pyrrolidin-2-yl}-1H-imidazol-5-yl)-1-benzofuran-2-yl]ph- enyl}-1H-imidazol-2-yl)pyrrolidin-1-yl]-2-phenylethanone; methyl{(1S)-1-cyclopropyl-2-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S)-2-cycloprop- yl-2-[(methoxycarbonyl)amino]acetyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-b- enzofuran-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-2-oxoethyl}carbam- ate; methyl{(1R)-1-cyclopropyl-2-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2R)-2-cyclo- propyl-2-[(methoxycarbonyl)amino]acetyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}- -1-benzofuran-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-2-oxoethyl}ca- rbamate; methyl{(2R)-1[(2S)-2-{5-[2-(4-{2-[(2S)-1-{(2R)-2-[(methoxycarbony- l)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl }phenyl)-1-benzofuran-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-- oxobutan-2-yl}carbamate; methyl{(2S)-1-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino- ]-3,3-dimethylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-2-y- l)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3 ,3-dimethyl-1-oxobutan-2-yl}carbamate; methyl{(1R)-2-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2R)-2-[(methoxycarbonyl)amino- ]-2-phenylacetyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}-1-benzofuran-2-yl)phen- yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate; methyl{(2S,3R)-1-[(2S)-2-(5-{2-[4-(2-{(2S)-1-[N-(methoxycarbonyl)-L-alloi- soleucyl]pyrrolidin-2-yl}-1H-imidazol-5-yl)phenyl]-1-benzofuran-5-yl}-1H-i- midazol-2-yl)pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl}carbamate; methyl{(2S)-3-hydroxy-1-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S)-3-hydroxy-2-[(m- ethoxycarbonyl)amino]propanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzof- uran-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-1-oxopropan-2-yl}carba- mate; methyl{(2S,3R)-3-hydroxy-1-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S,3R)-3-hy- droxy-2-[(methoxycarbonyl)amino]butanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl- }-1-benzofuran-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-1-oxobutan-2- -yl}carbamate; methyl{(2S)-1-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino- ]-4-methylpentanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-2-yl)p- henyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl}carbama- te; methyl{(2S)-1-[(2S)-2-{5-[3-fluoro-4-(5-{2-[(2S)-1-{(2S)-2-[(methoxyca- rbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzof- uran-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-- yl}carbamate; methyl{(1R)-2-[(2S)-2-{5-[3-fluoro-4-(5-{2-[(2S)-1-{(2R)-2-[(methoxycarbo- nyl)amino]-2-phenylacetyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-- 2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbama- te; methyl{(2S)-1-[(2S)-2-{5-[3-fluoro-4-(5-{2-[(2S)-1-{(2S)-2-[(methoxyca- rbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzof- uran-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-- yl}carbamate; methyl{(2S)-1-[(2S)-2-{5-[2-(2,6-difluoro-4-{2-[(2S)-1-{(2S)-2-[(methoxyc- arbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)-- 1-benzofuran-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2- -yl}carbamate; methyl{(1R)-2-[(2S)-2-{5-[3-methoxy-4-(5-{2-[(2S)-1-{(2R)-2-[(methoxycarb- onyl)amino]-2-phenylacetyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran- -2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbam- ate; methyl{(2S)-1-[(2S)-2-{5-[2-(2-chloro-4-{2-[(2S)-1-{(2S)-2-[(methoxyc- arbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}phenyl)-- 1-benzofuran-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2- -yl}carbamate; methyl{(1R)-2-[(2S)-2-{4-[3-cyano-4-(5-{2-[(2S)-1-{(2R)-2-[(methoxycarbon- yl)amino]-2-phenylacetyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-2- -yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamat- e; methyl{(2S)-1-[(2S)-2-{5-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)ami- no]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}-2-methylphenyl)-1-- benzofuran-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-y- l}carbamate; methyl[(1S)-2-[(2S)-2-(5-{3-fluoro-4-[5-(2-{(2S)-1-[(2S)-2-[(methoxycarbo- nyl)amino]-2-(tetrahydro-2H-pyran-4-yl)acetyl]pyrrolidin-2-yl}-1H-imidazol- -5-yl) -1-benzofuran-2-yl]phenyl}-1H-imidazol-2-yl)pyrrolidin-1-yl]-2-oxo -1-(tetrahydro-2H-pyran-4-yl)ethyl]carbamate; and methyl{(2S)-1-[(2S)-2-{4-[3-fluoro-4-(5-{2-[(2S)-1-{(2R)-2-[(methoxycarbo- nyl)amino]-2-phenylacetyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-- 2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}ca- rbamate.

12. A compound according to claim 1, chosen from the group consisting of: methyl{(2S)-1-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S)-2-[(methoxy-carbonyl)amin- o]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-2-yl)p- henyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamat- e; methyl{(2R)-1-[(2S)-2-{5-[2-(4-{2-[(2S)-1-{(2R)-2-[(methoxycarbonyl)ami- no]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)-1-benzofura- n-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbama- te; methyl{(2S)-1-[(2S)-2-{5-[4-(5-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)am- ino]-4-methylpentanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-2-y- l)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl}carb- amate; methyl{(2S)-1-[(2S)-2-{5-[3-fluoro-4-(5-{2-[(2S)-1-{(2S)-2-[(methox- ycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-ben- zofuran-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan- -2-yl}carbamate; methyl{(2S)-1-[(2S)-2-{5-[3-fluoro-4-(5-{2-[(2S)-1-{(2S)-2-[(methoxycarbo- nyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofura- n-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}- carbamate; methyl{(2S)-1-[(2S)-2-{5-[2-(2,6-difluoro-4-{2-[(2S)-1-{(2S)-2-- [(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-5-y- l}phenyl)-1-benzofuran-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-- oxobutan-2-yl}carbamate; methyl{(2S )-1-[(2S)-2-{5-[2-(2-chloro-4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]- -3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}phenyl)-1-benzofuran-5- -yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate; methyl{(1R)-2-[(2S)-2-{4-[3-cyano-4-(5-{2[(2S)-1-{(2R)-2-[(methoxycarbony- l)amino]-2-phenylacetyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}-1-benzofuran-2-- yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate- ; and methyl{(2S)-1-[(2S)-2-{5-[2-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)- amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}-2-methylphenyl)- -1-benzofuran-5-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-- 2-yl}carbamate; and pharmaceutically acceptable salts thereof.

13. A pharmaceutical composition comprising an effective amount of the compound according to claim 1, and a pharmaceutically acceptable carrier.

14. The pharmaceutical composition according to claim 13, further comprising a second therapeutic agent selected from the group consisting of HCV antiviral agents, immunomodulators, and anti-infective agents.

15. The pharmaceutical composition according to claim 13, further comprising a second therapeutic agent selected from the group consisting of HCV protease inhibitors and HCV NSSB polymerase inhibitors.

16. A method of treating a patient infected with HCV comprising the step of administering an amount of the compound according to claim 1 effective to treat infection by HCV in a subject in need thereof.
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