US2010173851A1PendingUtilityA1
Inhibitors of serine proteases, particularly hcv ns3-ns4a protease
Est. expiryApr 11, 2022(expired)· nominal 20-yr term from priority
Inventors:Janos PitlikKevin Michael CottrellLuc FarmerRobert B. PerniLawrence CourtneyJohn H. Van DrieMark A. Murcko
A61P 31/14A61P 37/02A61P 31/12A61P 43/00C07D 405/14C07D 209/12C07D 409/12C07D 401/14C07D 417/12A61P 1/16C07D 405/12C07K 5/1024C07D 471/04C07D 401/12C07D 403/12C07K 5/06008C07K 5/0812C07D 403/14C07K 5/1027C07D 209/42
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Claims
Abstract
The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention. The invention further relates to processes for preparing these compounds.
Claims
exact text as granted — not AI-modified1 .- 25 . (canceled)
26 . A compound of formula (II):
wherein:
X 1 is —N(R 20 )—, —O—, —S—, or —C(R′) 2 —;
X 2 is —C(O)—, —C(S)—, —S(O)—, or —S(O) 2 —;
W is:
m is 0 or 1;
each R 17 is independently:
hydrogen-,
(C1-C12)-aliphatic-,
(C3-C10)-cycloalkyl- or cycloalkenyl-,
[(C3-C10)-cycloalkyl- or cycloalkenyl]-(C1-C12)-aliphatic-,
(C6-C10)-aryl-,
(C6-C10)-aryl-(C1-C12)aliphatic-,
(C3-C10)-heterocyclyl-,
(C3-C10)-heterocyclyl-(C1-C12)-aliphatic-,
(C5-C10)heteroaryl-, or
(C5-C10)heteroaryl-(C1-C12)-aliphatic-, or
two R 17 groups, which are bound to the same nitrogen atom, form together with that nitrogen atom, a (C3-C10)-membered heterocyclic ring having in addition to the nitrogen up to 2 additional heteroatoms selected from N, NH, O, S, SO, and SO 2 ;
wherein R 17 is optionally substituted with up to 3 J substituents;
each R 18 is independently —OR′; or the OR′ groups together with the boron atom, is a (C5-C20)-membered heterocyclic ring having in addition to the boron up to 3 additional heteroatoms selected from N, NH, O, S, SO, and SO 2 ;
R 5 and R 5′ are independently hydrogen or (C1-C12)-aliphatic, wherein any hydrogen is optionally replaced with halogen, and wherein any terminal carbon atom is optionally substituted with sulfhydryl or hydroxy, and wherein up to two aliphatic carbon atoms may be replaced by a heteroatom selected from N, NH, O, S, SO, or SO 2 ; or
R 5 and R 5′ together with the atom to which they are bound is a 3- to 6-membered ring having up to 2 heteroatoms selected from N, NH, O, S, SO, or SO 2 ; wherein the ring has up to 2 substituents selected independently from J;
R 1 , R 1′ , R 11 , R 11′ , R 13 , and R 13′ are independently:
hydrogen-,
(C1-C12)-aliphatic-,
(C3-C10)-cycloalkyl or cycloalkenyl-,
[(C3-C10)-cycloalkyl or cycloalkenyl]-(C1-C12)-aliphatic-,
(C6-C10)-aryl-,
(C6-C10)-aryl-(C1-C12)aliphatic-,
(C3-C10)-heterocyclyl-,
(C6-C10)-heterocyclyl-(C1-C12)aliphatic,
(C5-C10)-heteroaryl-, or
(C5-C10)-heteroaryl-(C1-C12)-aliphatic-,
wherein each of R 1 , R 1′ , R 11 , R 11′ , R 13 , and R 13′ is independently and optionally substituted with up to 3 substituents independently selected from J;
wherein any ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cycloalkyl, or (C3-C10)heterocyclyl;
wherein up to 3 aliphatic carbon atoms in each of R 1 , R 1′ , R 11 , R 11′ , R 13 , and R 13′ may be replaced by a heteroatom selected from O, N, NH, S, SO, or SO 2 in a chemically stable arrangement; or
R 1 and R 1′ together with the atom to which they are bound is a 3- to 6-membered ring having up to 2 heteroatoms selected from N, NH, O, S, SO, or SO 2 ; wherein the ring has up to 2 substituents selected independently from J; or
R 11 and R 11′ together with the atom to which they are bound is a 3- to 6-membered ring having up to 2 heteroatoms selected from N, NH, O, S, SO, or SO 2 ; wherein the ring has up to 2 substituents selected independently from J; or
R 13 and R 13′ together with the atom to which they are bound is a 3- to 6-membered ring having up to 2 heteroatoms selected from N, NH, O, S, SO, or SO 2 ; wherein the ring has up to 2 substituents selected independently from J;
R 2 , R 4 , R 12 , and R 20 are independently
hydrogen-,
(C1-C12)-aliphatic-,
(C3-C10)-cycloalkyl or -cycloalkenyl-,
[(C3-C10)-cycloalkyl or -cycloalkenyl]-(C1-C12)-aliphatic-,
(C6-C10)-aryl-,
(C6-C10)-aryl-(C1-C12)aliphatic-,
(C3-C10)-heterocyclyl-,
(C6-C10)-heterocyclyl-(C1-C12)aliphatic,
(C5-C10)-heteroaryl-, or
(C5-C10)-heteroaryl-(C1-C12)-aliphatic-,
wherein each R 2 , R 4 , R 12 , and R 20 is independently and optionally substituted with up to 3 substituents independently selected from J;
wherein up to two aliphatic carbon atoms in R 2 , R 4 , R 12 , and R 20 may be replaced by a heteroatom selected from O, N, NH, S, SO, or SO 2 ; or
R 11 and R 12 together with the atoms to which they are bound form a 3- to a 20-membered mono-, a 4- to 20-membered bi-, or a 5- to 20-membered tri-cyclic carbocyclic or heterocyclic ring system;
wherein, in the bi- and tri-cyclic ring system, each ring is linearly fused, bridged, or spirocyclic;
wherein each ring is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cycloalkyl, or (C3-C10)heterocyclyl; and
wherein said ring has up to 3 substituents selected independently from J; or
R 12 and R 13 together with the atoms to which they are bound form a 4- to a 20-membered mono-, a 5- to 20-membered bi-, or a 6- to 20-membered tri-cyclic carbocyclic or heterocyclic ring system;
wherein, in the bi- and tri-cyclic ring system, each ring is linearly fused, bridged, or spirocyclic;
wherein each ring is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cycloalkyl, or (C3-C10)heterocyclyl; and
wherein said ring has up to 3 substituents selected independently from J; or
R 11 and R 13 together with the atoms to which they are bound form a 5- to a 20-membered mono-, a 6- to 20-membered bi-, or a 7- to 20-membered tri-cyclic carbocyclic or heterocyclic ring system;
wherein, in the bi- and tri-cyclic ring system, each ring is linearly fused, bridged, or spirocyclic;
wherein each ring is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cyclo alkyl, or (C3-C10)heterocyclyl; and
wherein said ring has up to 3 substituents selected independently from J; or
R 11 , R 12 , and R 13 together with the atoms to which they are bound form a 5- to a 20-membered bi-, or a 6- to 20-membered tri-cyclic carbocyclic or heterocyclic ring system;
wherein, in the bi- and tri-cyclic ring system, each ring is linearly fused, bridged, or spirocyclic;
wherein each ring is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cyclo alkyl, or (C3-C10)heterocyclyl; and
wherein said ring has up to 3 substituents selected independently from J; or
R 13′ and R 2 together with the atoms to which they are bound form a 3- to a 20-membered mono-, a 4- to 20-membered bi-, or a 5- to 20-membered tri-cyclic carbocyclic or heterocyclic ring system;
wherein, in the bi- and tri-cyclic ring system, each ring is linearly fused, bridged, or spirocyclic;
wherein each ring is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cyclo alkyl, or (C3-C10)heterocyclyl; and
wherein said ring has up to 3 substituents selected independently from J; or
R 5 and R 13 together with the atoms to which they are bound form a 18- to a 23-membered mono-, a 19- to 24-membered bi-, or a 20- to 25-membered tri-cyclic carbocyclic or heterocyclic ring system;
wherein, in the bi- and tri-cyclic ring system, each ring is linearly fused, bridged, or spirocyclic;
wherein each ring is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cycloalkyl, or (C3-C10)heterocyclyl; and
wherein said ring has up to 6 substituents selected independently from J; or
R 1 and R 12 together with the atoms to which they are bound form a 18- to a 23-membered mono-, a 19- to 24-membered bi-, or a 20- to 25-membered tri-cyclic carbocyclic or heterocyclic ring system;
wherein, in the bi- and tri-cyclic ring system, each ring is linearly fused, bridged, or spirocyclic;
wherein each ring is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cycloalkyl, or (C3-C10)heterocyclyl; and
wherein said ring has up to 6 substituents selected independently from J; or
R 14 is —H, —S(O)R′, —S(O) 2 R′, —C(O)R′, —C(O)OR′, —C(O)N(R′) 2 , —N(R′)C(O)R′, —N(COR′)COR′, —SO 2 N(R′) 2 , —SO 3 R′, —C(O)C(O)R′, —C(O)CH 2 C(O)R′, —C(S)R′, —C(S)N(R′) 2 , —(CH 2 ) 0-2 NHC(O)R′, —N(R′)N(R′)COR′, —N(R′)N(R′)C(O)OR′, —N(R′)N(R′)CON(R′) 2 , —N(R′)SO 2 R′, —N(R′)SO 2 N(R′) 2 , —N(R′)C(O)OR′, —N(R′)C(O)R′, —N(R′)C(S)R′, —N(R′)C(O)N(R′) 2 , —N(R′)C(S)N(R′) 2 , —N(COR′)COR′, —N(OR′)R′, —C(═NH)N(R′) 2 , —C(O)N(OR′)R′, —C(═NOR′)R′, —OP(O)(OR′) 2 , —P(O)(R′) 2 , —P(O)(OR′) 2 , or —P(O)(H)(OR′);
R 15 and R 16 are independently halogen, —OR′, —OC(O)N(R′) 2 , —NO 2 , —CN, —CF 3 , OCF 3 , —R′, oxo, 1,2-methylenedioxy, 1,2-ethylenedioxy, —N(R′) 2 , —SR′, —SOR′, —SO 2 R′, —SO 2 N(R′) 2 , —SO 3 R′, —C(O)R′, —C(O)C(O)R′, —C(O)CH 2 C(O)R′, —C(S)R′, —C(O)OR′, —OC(O)R′, —C(O)N(R′) 2 , —OC(O)N(R′) 2 , —C(S)N(R′) 2 , —(CH 2 ) 0-2 NHC(O)R′, —N(R′)N(R′)COR′, —N(R′)N(R′)C(O)OR′, —N(R′)N(R′)CON(R′) 2 , —N(R′)SO 2 R′, —N(R′)SO 2 N(R′) 2 , —N(R′)C(O)OR′, —N(R′)C(O)R′, —N(R′)C(S)R′, —N(R′)C(O)N(R′) 2 , —N(R′)C(S)N(R′) 2 , —N(COR′)COR′, —N(OR′)R′, —CN, —C(═NH)N(R′) 2 , —C(O)N(OR′)R′, —C(═NOR′)R′, —OP(O)(OR′) 2 , —P(O)(R′) 2 , —P(O)(OR′) 2 , or —P(O)(H)(OR′);
Z 2 is ═O, ═NR′, ═NOR′, or ═C(R′) 2 ;
R 19 is —OR′, —CF 3 , —OCF 3 , —R′, —N(R′) 2 , —SR′, —C(O)R′, —COOR′—CON(R′) 2 , —N(R′)COR′, or —N(COR′)COR′;
J is halogen, —OR′, —OC(O)N(R′) 2 , —NO 2 , —CN, —CF 3 , —OCF 3 , —R′, oxo, thioxo, 1,2-methylenedioxy, 1,2-ethylenedioxy, —N(R′) 2 , —SR′, —SOR′, —SO 2 R′, —SO 2 N(R′) 2 , —SO 3 R′, —C(O)R′, —C(O)C(O)R′, —C(O)CH 2 C(O)R′, —C(S)R′, —C(O)OR′, —OC(O)R′, —C(O)N(R′) 2 , —OC(O)N(R′) 2 , —C(S)N(R′) 2 , —(CH 2 ) 0-2 NHC(O)R′, —N(R′)N(R′)COR′, —N(R′)N(R′)C(O)OR′, —N(R′)N(R′)CON(R′) 2 , —N(R′)SO 2 R′, —N(R′)SO 2 N(R′) 2 , —N(R′)C(O)OR′, —N(R′)C(O)R′, —N(R′)C(S)R′, —N(R′)C(O)N(R′) 2 , —N(R′)C(S)N(R′) 2 , —N(COR′)COR′, —N(OR′)R′, —CN, —C(═NH)N(R′) 2 , —C(O)N(OR′)R′, —C(═NOR′)R′, —OP(O)(OR′) 2 , —P(O)(R′) 2 , —P(O)(OR′) 2 , or —P(O)(H)(OR′); wherein:
two R′ groups together with the atoms to which they are bound form a 3- to 10-membered aromatic or non-aromatic ring having up to 3 heteroatoms independently selected from N, NH, O, S, SO, or SO 2 , wherein the ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cycloalkyl, or a (C3-C10)heterocyclyl, and wherein any ring has up to 3 substituents selected independently from J 2 ; or
each R′ is independently selected from:
hydrogen-,
(C1-C12)-aliphatic-,
(C3-C10)-cycloalkyl or -cycloalkenyl-,
[(C3-C10)-cycloalkyl or -cycloalkenyl]-(C1-C12)-aliphatic-,
(C6-C10)-aryl-,
(C6-C10)-aryl-(C1-C12)aliphatic-,
(C3-C10)-heterocyclyl-,
(C6-C10)-heterocyclyl-(C1-C12)aliphatic-,
(C5-C10)-heteroaryl-, or
(C5-C10)-heteroaryl-(C1-C12)-aliphatic-, wherein R′ has up to 3 substituents selected independently from J 2 ; and
J 2 is halogen, —OR′, —OC(O)N(R′) 2 , —NO 2 , —CN, —CF 3 , —OCF 3 , —R′, oxo, thioxo, 1,2-methylenedioxy, —N(R′) 2 , —SR′, —SOR′, —SO 2 R′, —SO 2 N(R′) 2 , —SO 3 R′, —C(O)R′, —C(O)C(O)R′, —C(O)CH 2 C(O)R′, —C(S)R′, —C(O)OR′, —OC(O)R′, —C(O)N(R′) 2 , —OC(O)N(R′) 2 , —C(S)N(R′) 2 , —(CH 2 ) 0-2 NHC(O)R′, —N(R′)N(R′)COR′, —N(R′)N(R′)C(O)OR′, —N(R′)N(R′)CON(R′) 2 , —N(R′)SO 2 R′, —N(R′)SO 2 N(R′) 2 , —N(R′)C(O)OR′, —N(R′)C(O)R′, —N(R′)C(S)R′, —N(R′)C(O)N(R′) 2 , —N(R′)C(S)N(R′) 2 , —N(COR′)COR′, —N(OR′)R′, —CN, —C(═NH)N(R′) 2 , —C(O)N(OR′)R′, —C(═NOR′)R′, —OP(O)(OR′) 2 , —P(O)(R′) 2 , —P(O)(OR′) 2 , or —P(O)(H)(OR′).
27 . The compound according to claim 26 , wherein:
R 11 is H; and R 12 is
(C1-C6)-alkyl,
(C3-C10)-cycloalkyl,
[(C3-C10)-cycloalkyl]-(C1-C12)-alkyl,
(C6-C10)-aryl,
(C6-C10)-aryl-(C1-C6)alkyl,
(C3-C10)-heterocyclyl,
(C6-C10)-heterocyclyl-(C1-C6)alkyl,
(C5-C10)-heteroaryl, or
(C5-C10)-heteroaryl-(C1-C6)-alkyl.
28 . The compound according to claim 27 , wherein R 12 is isobutyl, cyclohexyl, cyclohexylmethyl, benzyl, or phenylethyl.
29 . The compound according to claim 26 , wherein:
R 11 is:
(C1-C6)-alkyl,
(C3-C10)-cycloalkyl,
[(C3-C10)-cycloalkyl]-(C1-C12)-alkyl,
(C6-C10)-aryl,
(C6-C10)-aryl-(C1-C6)alkyl;
(C3-C10)-heterocyclyl,
(C6-C10)-heterocyclyl-(C1-C6)alkyl,
(C5-C10)-heteroaryl, or
(C5-C10)-heteroaryl-(C1-C6)-alkyl; and
R 12 is H.
30 . The compound according to claim 26 , wherein the
radical is:
31 . The compound according to claim 30 , wherein the
radical is:
32 . The compound according to claim 26 , wherein the
radical is:
wherein each B independently forms a 3- to a 20-membered carbocyclic or heterocyclic ring system;
wherein each ring B is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is N, NH, O, S, SO, or SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cyclo alkyl, or (C3-C10)heterocyclyl; and
wherein each ring has up to 3 substituents selected independently from J.
33 . The compound according to claim 32 , wherein the
radical is:
34 . The compound according to claim 32 , wherein the
radical is:
35 . The compound according to claim 32 , wherein the
radical is:
36 . The compound according to claim 32 , wherein the
radical is:
37 . The compound according to claim 32 , wherein the
radical is:
38 . The compound according to claim 26 , wherein the
radical is:
wherein each B independently forms a 3- to a 20-membered carbocyclic or heterocyclic ring system;
wherein each ring B is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is N, NH, O, S, SO, or SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cyclo alkyl, or (C3-C10)heterocyclyl; and
wherein each ring has up to 3 substituents selected independently from J.
39 . The compound according to claim 38 , wherein the
radical
40 . The compound according to claim 38 , wherein the
radical is:
41 . The compound according to claim 26 , wherein the
radical is:
42 . The compound according to claim 26 , wherein the
radical is:
wherein B forms a 3- to a 20-membered carbocyclic or heterocyclic ring system;
wherein each ring B is either aromatic or nonaromatic;
wherein each heteroatom in the heterocyclic ring system is N, NH, O, S, SO, or SO 2 ;
wherein each ring is optionally fused to a (C6-C10)aryl, (C5-C10)heteroaryl, (C3-C10)cycloalkyl, or (C3-C10)heterocyclyl; and
wherein each ring has up to 3 substituents selected independently from J.
43 . The compound according to claim 42 , wherein the
radical is:
44 . The compound according to claim 26 , wherein R 11 and R 12 together with the atoms to which they are bound form a 6- to 10-membered mono- or bicyclic carbocyclic or heterocyclic ring system;
wherein each heteroatom in the heterocyclic ring system is selected from the group consisting of N, NH, O, S, SO, and SO 2 ; and wherein said ring has up to 3 substituents selected independently from J.
45 . The compound according to claim 26 , wherein R 5′ is H and R 5 is (C1-C6)-alkyl, wherein the alkyl is optionally substituted with fluoro or —SH.
46 . The compound according to claim 45 , wherein the (C1-C6)-alkyl is substituted with 1 to 3 fluoro groups.
47 . The compound according to claim 46 , wherein R 5 and R 5′ are independently:
48 . The compound according to claim 26 , wherein R 13 is:
(C1-C6)-alkyl, (C3-C10)-cycloalkyl, [(C3-C10)-cycloalkyl]-(C1-C12)-alkyl, (C6-C10)-aryl, (C6-C10)-aryl-(C1-C6)alkyl, (C3-C10)-heterocyclyl, (C6-C10)-heterocyclyl-(C1-C6)alkyl, (C5-C10)-heteroaryl, or (C5-C10)-heteroaryl-(C1-C6)-alkyl; wherein R 13 is optionally substituted with up to 3 substituents independently selected from J; and wherein up to 3 aliphatic carbon atoms in R 13 may be replaced by a heteroatom selected from O, NH, S, SO, or SO 2 in a chemically stable arrangement.
49 . The compound according to claim 48 , wherein R 13 is:
50 . The compound according to claim 26 , wherein R 1 is
(C1-C6)-alkyl, (C3-C10)-cycloalkyl, [(C3-C10)-cycloalkyl]-(C1-C12)-alkyl, (C6-C10)-aryl, (C6-C10)-aryl-(C1-C6)alkyl, (C3-C10)-heterocyclyl, (C6-C10)-heterocyclyl-(C1-C6)alkyl, (C5-C10)-heteroaryl, or (C5-C10)-heteroaryl-(C1-C6)-alkyl; wherein R 1 is optionally substituted with up to 3 substituents independently selected from J; and wherein up to 3 aliphatic carbon atoms in R 1 may be replaced by a heteroatom selected from O, NH, S, SO, or SO 2 in a chemically stable arrangement.
51 . The compound according to claim 36 , wherein R 1 is:
52 . The compound according to claim 26 , wherein W is:
53 . The compound according to claim 52 , wherein W is:
54 . The compound according to claim 26 , wherein R 2 , R 4 , and R 20 are each independently H or (C1-C3)-alkyl.
55 . The compound according to claim 54 , wherein R 2 , R 4 , and R 20 are each H.
56 . The compound according to claim 26 , wherein R 14 is hydrogen.
57 . The compound according to claim 26 , wherein each R 15 and R 16 is independently (C1-C6)-alkyl-.
58 . The compound according to claim 57 , wherein each R 15 and R 16 are each methyl.
59 . The compound according to claim 26 , wherein Z 2 is O and R 19 is:
(C1-C6)-alkyl- (C3-C10)-cycloalkyl-, [(C3-C10)-cycloalkyl]-(C1-C12)-aliphatic-, (C6-C10)-aryl-, (C6-C10)-aryl-(C1-C6)alkyl, (C3-C10)-heterocyclyl, (C6-C10)-heterocyclyl-(C1-C6)alkyl, (C5-C10)-heteroaryl, or (C5-C10)-heteroaryl-(C1-C6)-alkyl; wherein R 19 has up to 3 substituents selected independently from J 2 ; and wherein up to 3 aliphatic carbon atoms in R 19 may be replaced by a heteroatom selected from O, NH, S, SO, or SO 2 in a chemically stable arrangement.
60 . The compound according to claim 59 , wherein each R 19 is methyl.
61 . The compound according to claim 26 , wherein R 14 is H; Z 2 is CH 2 ; and R 19 is:
62 . The compound according to claim 26 , wherein each R 19 is methyl; Z 2 is O; R 14 is:
63 . The compound according to claim 26 , wherein each R 19 is methyl; R 14 is H; and Z 2 is:
64 . The compound according to claim 63 , wherein Z 2 is:
65 . The compound according to claim 26 , wherein the compound is 63-67 or 68.
66 . A composition comprising a compound according to claim 26 or a pharmaceutically acceptable salt, derivative or prodrug thereof in an amount effective to inhibit a serine protease; and a acceptable carrier, adjuvant or vehicle.
67 . (canceled)
68 . (canceled)
69 . (canceled)
70 . A method of inhibiting the activity of a serine protease comprising the step of contacting said serine protease with a compound according to claim 26 .
71 . The method according to claim 70 , wherein said protease is an HCV NS3 protease.
72 . A method of treating an HCV infection in a patient comprising the step of administering to said patient a composition according to claim 67 .
73 . (canceled)
74 . (canceled)
75 . A method of eliminating or reducing HCV contamination of a biological sample or medical or laboratory equipment, comprising the step of contacting said biological sample or medical or laboratory equipment with a composition according to claim 66 .
76 . (canceled)Join the waitlist — get patent alerts
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