IP Library › Granted Patent US 8,236,950

Granted Patent B2

US 8,236,950 · App. 11/960,298 · Granted Aug 7, 2012

Anti-viral compounds

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Patent No.: US 8,236,950
App. No.: 11/960,298
Granted: Aug 7, 2012
Kind: B2

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Abstract

Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, co-formulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

Claims (101)

1. A compound, a tautomer of the compound, or a pharmaceutically acceptable salt of the compound or tautomer, wherein said compound has Formula I,

wherein:

A is carbocyclyl and B is heterocyclyl, and wherein A and B are each independently optionally substituted with one or more R 18 , wherein R 18 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S ,-L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), and -L S -N(R S )SO 2 N(R S′ R S″ );

Z is a bond, —CR 41 R 41′ — or —NR 41 —, wherein R 41 and R 41′ are each independently selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl;

R 10 and R 35 are each independently selected at each occurrence from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), and -L S -N(R S )SO 2 N(R S′ R S″ );

X is selected from the group consisting of a bond, alkylene, alkenylene, alkynylene, -L S -O—, -L S -S—, -L S -C(O)—, -L S -N(R S )—, -L S -N(R S )C(O)—, -L S -C(O)N(R S )—, -L S -N(R S )C(O)O—, -L S -OC(O)N(R S )—, -L S -N(R S )C(O)N(R S′ )—, -L S -C(═NR S )N(R S′ )—, -L S -N(R S′ )C(═NR S )—, -L S -S(O)—, -L S -SO 2 —, -L S -C(O)O— and -L S -OC(O)—;

R 22 is carbocyclyl or heterocyclyl, and is optionally substituted with one or more R 26 , wherein R 26 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, alkyl, alkenyl, alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N═C(NR S R S′ )(NR S R S′ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl); or R 22 is alkyl, alkenyl or alkynyl, and is optionally substituted with one or more R 26 ; or R 22 is hydrogen;

G is selected from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, alkyl, alkenyl, alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), and —Y—R 50 , wherein G is optionally substituted with one or more R 18 ;

Y is selected from the group consisting of a bond, —O—, —C(O)—, —S(O)—, —S(O) 2 —, —N(R 15 )—, —C(O)O—, —OC(O)—, —C(O)N(R 15 )—, —N(R 15 )C(O)—, —C(O)N(R 15 )O—, —N(R 15 )C(O)O—, —OC(O)N(R 15 )—, —N(R 15 )C(O)N(R 15′ )—, —C(O)N(R 15 )N(R 15′ )—, —S—, —C(S)—, —C(S)O—, —OC(S)—, —C(S)N(R 15 )—, —N(R 15 )C(S)—, —OS(O) 2 —, —OS(O)—, —OC(O)O—, —N(R 15 )—, —N(R 15 )S(O)—, —N(R 15 )S(O) 2 —, —S(O)N(R 15 )—, —S(O) 2 N(R 15 )—, —C(S)N(R 15 )O—, —N(R 15 )C(S)O—, —OC(S)N(R 15 )—, —N(R 15 )C(S)N(R 15′ )—, and —C(S)N(R 15 )N(R 15′ )—, wherein R 15 and R 15′ are each independently selected at each occurrence from the group consisting of hydrogen, alkyl, alkenyl and alkynyl;

R 50 is -L 1 -A 1 , wherein A 1 is selected from the group consisting of carbocyclyl, heterocyclyl, alkyl, alkenyl and alkynyl, and L 1 is selected from the group consisting of a bond, alkylene, alkenylene and alkynylene, wherein A 1 is optionally substituted with one or more R 30 , and R 30 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, alkyl, alkenyl, alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl), and wherein L 1 is optionally substituted with one or more R 38 , and R 38 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, alkoxy, thioalkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylamino, alkoxycarbonylamino, -L S -O—R S , -L S --S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl, -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl);

L S is independently selected at each occurrence from the group consisting of a bond, alkylene, alkenylene and alkynylene;

R S , R S′ and R S″ are each independently selected at each occurrence from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkoxy, thioalkoxy, alkoxyalkyl, alkoxyalkoxyalkyl, thioalkoxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkylamino, alkylaminoalkyl, alkoxycarbonylamino, and alkoxycarbonylaminoalkyl;

L E and L E′ are each independently selected at each occurrence from the group consisting of a bond, alkylene, alkenylene and alkynylene;

Q is independently selected at each occurrence from the group consisting of a bond, alkylene, alkenylene, alkynylene, —S—, —O—, —C(O)—, —N(R S )—, —N(R S )C(O)—, —C(O)N(R S )—, —N(R S )C(O)O—, —OC(O)N(R S )—, —N(R S )C(O)N(R S′ )—, —C(═NR S )N(R S′ )—, —N(R S′ )C(═NR S )—, —S(O)—, —SO 2 —, —O—SO 2 —, —SO 2 —O—, —O—S(O)—, —S(O)—O—, —C(O)O— and —OC(O)—;

R 10 , R 15 , R 15′ , R 18 , R 26 , R 30 , R 35 , R 38 , R 41 , and R 41′ are each independently optionally substituted at each occurrence with at least one substituent selected from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate and azido; and

each C 3 -C 18 carbocyclyl and M 3 -M 18 heterocyclyl moiety in -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl) is independently optionally substituted at each occurrence with at least one substituent selected from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, alkyl, alkenyl, alkynyl, alkoxy, thioalkoxy, alkoxyalkyl, thioalkoxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylcarbonyloxy, alkylcarbonyloxyalkyl, alkylamino, alkylaminoalkyl, alkoxycarbonylamino, and alkoxycarbonylaminoalkyl.

2. The compound, tautomer or salt of claim 1 , wherein:

A is C 3 -C 18 carbocyclyl and B is M 3 -M 18 heterocyclyl, and are each independently optionally substituted with one or more R 18 , wherein R 18 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 carbocyclyl, M 3 -M 6 heterocyclyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), and -L S -N(R S )SO 2 N(R S′ R S″ );

Z is a bond, —CR 41 R 41′ — or —NR 41 —, wherein R 41 and R 41′ are each independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl;

R 10 and R 35 are each independently selected at each occurrence from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 carbocyclyl, M 3 -M 6 heterocyclyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), and -L S -N(R S )SO 2 N(R S′ R S ″);

X is selected from the group consisting of a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene, -L S -O—, -L S -S—, -L S -C(O)—, -L S -N(R S )—, -L S -N(R S )C(O)—, -L S -C(O)N(R S )—, -L S -N(R S )C(O)O—, -L S -OC(O)N(R S )—, -L S -N(R S )C(O)N(R S′ )—, -L S -C(═NR S )N(R S′ )—, -L S -N(R S′ )C(═NR S )—, -L S -S(O)—, -L S -SO 2 —, -L S -C(O)O— and -L S -OC(O)—;

R 22 is C 3 -C 18 carbocyclyl or M 3 -M 18 heterocyclyl, and is optionally substituted with one or more R 26 , wherein R 26 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N═C(NR S R S′ )(NR S R S′ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl); or R 22 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, and is optionally substituted with one or more R 26 ; or R 22 is hydrogen;

G is selected from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S --O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), and —Y—R 50 , wherein G is optionally substituted with one or more R 18 ;

R 50 is -L 1 -A 1 , wherein A 1 is selected from the group consisting of C 3 -C 18 carbocyclyl, M 3 -M 18 heterocyclyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, and L 1 is selected from the group consisting of a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene and C 2 -C 6 alkynylene, wherein A 1 is optionally substituted with one or more R 30 , and R 30 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl), and wherein L 1 is optionally substituted with one or more R 38 , and R 38 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkoxy, C 1 -C 6 thioalkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylamino, C 1 -C 6 alkoxycarbonylamino, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), C 3 -C 18 carbocyclyl, M 3 -M 18 heterocyclyl, C 3 -C 18 carbocyclylC 1 -C 6 alkyl, M 3 -M 18 heterocyclylC 1 -C 6 alkyl, -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl);

L S is independently selected at each occurrence from the group consisting of a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene and C 2 -C 6 alkynylene;

R S , R S′ and R S″ are each independently selected at each occurrence from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkoxyC 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 thioalkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonylC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonyloxyC 1 -C 6 alkyl, C 1 -C 6 alkylamino, C 1 -C 6 alkylaminoC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonylamino, and C 1 -C 6 alkoxycarbonylaminoC 1 -C 6 alkyl;

L E and L E′ are each independently selected at each occurrence from the group consisting of a bond, C 1 -C 6 alkyl, C 1 -C 6 alkenyl and C 1 -C 6 alkynyl;

Q is independently selected at each occurrence from the group consisting of a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene, —S—, —O—, —C(O)—, —N(R S )—, —N(R S )C(O)—, —C(O)N(R S )—, —N(R S )C(O)O—, —OC(O)N(R S )—, —N(R S )C(O)N(R S′ )—, —C(═NR S )N(R S′ )—, —N(R S′ )C(═NR S )—, —S(O)—, —SO 2 —, —O—SO 2 —, —SO 2 —O—, —O—S(O)—, —S(O)—O—, —C(O)O— and —OC(O)—;

each C 3 -C 18 carbocyclyl and M 3 -M 18 heterocyclyl moiety in -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl) is independently optionally substituted at each occurrence with at least one substituent selected from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 thioalkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonylC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonyloxyC 1 -C 6 alkyl, C 1 -C 6 alkylamino, C 1 -C 6 alkylaminoC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonylamino, and C 1 -C 6 alkoxycarbonylaminoC 1 -C 6 alkyl.

3. The compound, tautomer or salt of claim 2 , wherein A is C 5 -C 6 carbocyclyl and is optionally substituted with one or more R 18 , and B is M 5 -M 6 heterocyclyl optionally substituted with one or more R 18 .

4. The compound, tautomer or salt of claim 2 , wherein G is —Y—R 50 , R 50 is -L 1 -A 1 - and A 1 is C 5 -C 12 carbocyclyl or M 5 -M 10 heterocyclyl and is optionally substituted with one or more R 30 .

5. The compound, tautomer or salt of claim 4 , wherein Y is —O—, —S—, —C(O)N(R 15 )— or —N(R 15 )C(O)—, R 15 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, L 1 is C 1 -C 6 alkylene optionally substituted with one or more R 38 , and A 1 is a C 4 -C 7 carbocyclyl or M 4 -M 7 heterocyclyl and is optionally substituted with one or more R 30 .

6. The compound, tautomer or salt of claim 4 , wherein Y is —O—, —S—, —C(O)N(R 15 )— or —N(R 15 C(O)—, R 15 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, L 1 is a bond or C 1 -C 6 alkylene optionally substituted with one or more R 38 , and A 1 is a bicyclic ring which has from 6 to 11 ring atoms and is optionally substituted with one or more R 30 .

7. The compound, tautomer or salt of claim 4 , wherein X is —O— or —S—, and R 22 is C 5 -C 6 carbocyclyl or M 5 -M 6 heterocyclyl and is optionally substituted with one or more R 26 .

8. The compound, tautomer or salt of claim 4 , wherein R 10 , R 35 , R 41 and R 41′ are each independently selected at each occurrence from hydrogen, halogen or C 1 -C 6 alkyl.

9. The compound, tautomer or salt of claim 2 , wherein:

Z is —NR 41 —;

R 35 is selected from hydrogen, halogen or C 1 -C 5 alkyl;

R 41 is selected from hydrogen or C 1 -C 6 alkyl;

R 10 is hydrogen;

A is a C 5 -C 6 carbocyclyl and is optionally substituted with one or more R 18 ;

B is M 5 -M 6 heterocyclyl optionally substituted with one or more R 18

X is —S— or —O—;

R 22 is

wherein R 48 is hydroxy, amino, C 1 -C 6 alkylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkoxycarbonylamino or C 1 -C 6 alkylcarbonyloxy, and R 22 is optionally substituted with one or more R 26 ;

G is —Y—R 50 ;

Y is —O—, —C(O)—, —S(O)—, —S(O) 2 —, —N(R 15 )—, —C(O)O—, —OC(O)—, —C(O)N(R 15 )—, —N(R 15 )C(O)—, —C(O)N(R 15 )O—, —N(R 15 )C(O)O—, —OC(O)N(R 15 )—, —N(R 15 )C(O)N(R 15′ )—, —C(O)N(R 15 )N(R 15′ )—, —S—, —C(S)—, —C(S)O—, —OC(S)—, —C(S)N(R 15 )—, —N(R 15 )C(S)—, —OS(O) 2 —, —OS(O)—, —OC(O)O—, —N(R 15 )—, —N(R 15 )S(O)—, —N(R 15 )S(O) 2 —, —S(O)N(R 15 )—, —S(O) 2 N(R 15 )—, —C(S)N(R 15 )O—, —N(R 15 )C(S)O—, —OC(S)N(R 15 )—, —N(R 15 )C(S)N(R 15′ )—, and —C(S)N(R 15 )N(R 15′ )—, wherein R 15 and R 15′ are each independently selected at each occurrence from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl;

R 50 is -L 1 -A 1 , wherein:

L 1 is C 1 -C 6 alkylene and is optionally substituted with one or more R 38 , and A 1 is a C 4 -C 12 carbocyclyl or M 4 -M 12 heterocyclyl and is optionally substituted with one or more R 30 ; or

L 1 is a bond, and A 1 is a C 4 -C 6 carbocyclyl or M 4 -M 12 heterocyclyl and is optionally substituted with one or more R 30 ; or

L 1 is a bond, and A 1 is a bicyclic ring having from 6 to 12 ring atoms and is optionally substituted with one or more R 30 .

10. The compound, tautomer or salt of claim 1 , wherein said compound has Formula I(a),

wherein:

A is a carbocyclyl or heterocyclyl, and is optionally substituted with one or more R 18 , wherein R 18 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S --O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), and -L S -N(R S )SO 2 N(R S′ R S″ );

R 10 , R 17 , R 35 and R 44 are each independently selected at each occurrence from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 carbocyclyl, M 3 -M 6 heterocyclyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), and -L S -N(R S )SO 2 N(R S′ R S″ );

R 22 is C 3 -C 18 carbocyclyl or M 3 -M 18 heterocyclyl, and is optionally substituted with one or more R 26 , wherein R 26 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S --S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N═C(NR S R S′ )(NR S R S′ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl); or R 22 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, and is optionally substituted with one or more R 26 ; or R 22 is hydrogen;

G is selected from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), and —Y—R 50 , wherein G is optionally substituted with one or more R 18 ;

R 50 is -L 1 -A 1 , wherein A 1 is selected from the group consisting of C 3 -C 18 carbocyclyl, M 3 -M 18 heterocyclyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, and L 1 is selected from the group consisting of a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene and C 2 -C 6 alkynylene, wherein A 1 is optionally substituted with one or more R 30 , and R 30 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , —, -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E -(M 3 -M 18 heterocyclyl), and wherein L 1 is optionally substituted with one or more R 38 , and R 38 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkoxy, C 1 -C 6 thioalkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylamino, C 1 -C 6 alkoxycarbonylamino, -L S -O—R S , -L S --S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), C 3 -C 18 carbocyclyl, M 3 -M 18 heterocyclyl, C 3 -C 18 carbocyclylC 1 -C 6 alkyl, M 3 -M 18 heterocyclylC 1 -C 6 alkyl, -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl);

L S is independently selected at each occurrence from the group consisting of a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene and C 2 -C 6 alkynylene;

L E and L E′ are each independently selected at each occurrence from the group consisting of a bond, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl;

R 10 , R 15 , R 15′ , R 17 , R 18 , R 26 , R 30 , R 33 , R 35 , R 38 , R 41 , R 41′ and R 44 are each independently optionally substituted at each occurrence with at least one substituent selected from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate and azido; and

each C 3 -C 18 carbocyclyl and M 3 -M 18 heterocyclyl moiety in -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl) is independently optionally substituted at each occurrence with at least one substituent selected from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 thioalkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonyloxyC 1 -C 6 alkyl, C 1 -C 6 alkylamino, C 1 -C 6 alkylaminoC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonylamino, and C 1 -C 6 alkoxycarbonylaminoC 1 -C 6 alkyl.

11. The compound, tautomer or salt of claim 10 , wherein Z is —NR 41 —.

12. The compound, tautomer or salt of claim 11 , wherein A is C 5 -C 6 carbocyclyl and is optionally substituted with one or more R 18 , G is —Y—R 50 , and A 1 is C 5 -C 6 carbocyclyl or M 5 -M 6 heterocyclyl and is optionally substituted with one or more R 30 .

13. The compound, tautomer or salt of claim 12 , wherein X is —O— or —S—, R 22 is C 5 -C 6 carbocyclyl or M 5 -M 6 heterocyclyl and is optionally substituted with one or more R 26 .

14. The compound, tautomer or salt of claim 13 , wherein Y is —O—, —S—, —C(O)N(R 15 )— or —N(R 15 )C(O)—.

15. The compound, tautomer or salt of claim 1 , wherein said compound has Formula I(b),

wherein:

R 10 , R 17 , R 35 , R 41 and R 44 are each independently selected from hydrogen, halogen, C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl;

X is —S— or —O—;

R 22 is

wherein R 48 is hydroxy, amino, C 1 -C 6 alkylamino or C 1 -C 6 alkoxy, and R 22 is optionally substituted with one or more R 26 ;

Y is selected from the group consisting of —O—, —C(O)—, —S(O)—, —S(O) 2 —, —N(R 15 )—, —C(O)O—, —OC(O)—, —C(O)N(R 15 )—, —N(R 15 )C(O)—, —C(O)N(R 15 )O—, —N(R 15 )C(O)O—, —OC(O)N(R 15 )—, —N(R 15 )C(O)N(R 15′ )—, —C(O)N(R 15 )N(R 15′ )—, —S—, —C(S)—, —C(S)O—, —OC(S)—, —C(S)N(R 15 )—, —N(R 15 )C(S)—, —OS(O) 2 —, —OS(O)—, —OC(O)O—, —N(R 15 )—, —N(R 15 )S(O)—, —N(R 15 )S(O) 2 —, —S(O)N(R 15 )—, —S(O) 2 N(R 15 )—, —C(S)N(R 15 )O—, —N(R 15 )C(S)O—, —OC(S)N(R 15 )—, —N(R 15 )C(S)N(R 15′ )—, and —C(S)N(R 15 )N(R 15′ )—, wherein R 15 and R 15′ are each independently selected at each occurrence from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl;

R 50 is -L 1 -A 1 , wherein L 1 a bond or C 1 -C 6 alkylene optionally substituted with one or more R 38 , and A 1 is C 5 -C 10 carbocyclyl or M 5 -M 10 heterocyclyl and is optionally substituted with one or more R 30 ;

R 18 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), and -L S -N(R S )SO 2 N(R S′ R S″ );

R 26 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N═C(NR S R S′ )(NR S R S′ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl);

R 30 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl);

R 38 is independently selected at each occurrence from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkoxy, C 1 -C 6 thioalkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylamino, C 1 -C 6 alkoxycarbonylamino, -L S -O—R S , -L S -S—R S , -L S -C(O)R S , -L S -OC(O)R S , -L S -C(O)OR S , -L S -N(R S R S′ ), -L S -C(═NR S )R S′ , -L S -S(O)R S , -L S -SO 2 R S , -L S -C(O)N(R S R S′ ), -L S -N(R S )C(O)R S′ , -L S -C(═NR S )N(R S′ R S″ ), -L S -N(R S′ )C(═NR S )R S″ , -L S -N(R S )C(O)N(R S′ R S″ ), -L S -N(R S )SO 2 R S′ , -L S -SO 2 N(R S R S′ ), -L S -N(R S )SO 2 N(R S′ R S″ ), C 3 -C 18 carbocyclyl, M 3 -M 18 heterocyclyl, C 3 -C 18 carbocyclylC 1 -C 6 alkyl, M 3 -M 18 heterocyclylC 1 -C 6 alkyl, -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl);

L S is independently selected at each occurrence from the group consisting of a bond, C 1 -C 6 alkylene, C 2 -C 6 alkenylene and C 2 -C 6 alkynylene;

L E and L E′ are each independently selected at each occurrence from the group consisting of a bond, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl;

R 10 , R 15 , R 15′ , R 17 , R 18 , R 26 , R 30 , R 35 , R 38 , R 41 , and R 44 are each independently optionally substituted at each occurrence with at least one substituent selected from the group consisting of halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate and azido;

each C 3 -C 18 carbocyclyl and M 3 -M 18 heterocyclyl moiety in -L E -Q-L E′ -(C 3 -C 18 carbocyclyl) and -L E -Q-L E′ -(M 3 -M 18 heterocyclyl) is independently optionally substituted at each occurrence with at least one substituent selected from the group consisting of hydrogen, halogen, oxo, thioxo, hydroxy, mercapto, nitro, cyano, amino, carboxy, formyl, phosphate, azido, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 thioalkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonylC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonyloxyC 1 -C 6 alkyl, C 1 -C 6 alkylamino, C 1 -C 6 alkylaminoC 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonylamino, and C 1 -C 6 alkoxycarbonylaminoC 1 -C 6 alkyl; and

n is 0, 1, 2, or 3.

16. A pharmaceutical composition comprising a compound, tautomer or salt according to claim 1 .

17. A method of inhibiting HCV virus replication, comprising contacting HCV virus with an effective amount of a compound, tautomer or salt of claim 1 , thereby inhibiting replication of said virus.

18. A method of treating HCV infection, comprising administering an effective amount of a compound, tautomer or salt of claim 1 to an HCV patient in need thereof, thereby reducing HCV viral level in the blood or liver of the patient.

19. The compound, tautomer or salt of claim 15 , wherein the compound is selected from the group consisting of

4-[4-Methyl-2-(1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-6-ylamino) -phenylsulfanyl]-phenol;

4-[4-(3-Bromo-benzyloxy)-2-(1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-6-ylamino)-phenylsulfanyl]-phenol;

4-[4-Methyl-2-(2-methyl-1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-6-ylamino)-phenylsulfanyl]-phenol;

4-[4-(3-Fluoro-benzyloxy)-2-(2-methyl-1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-6-ylamino)-phenylsulfanyl]-phenol; and

4-[2-(2-Methyl-1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-6-ylamino)-4-(3-trifluoromethyl-benzyloxy)-phenylsulfanyl]-phenol.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013

From: ABBOTT LABORATORIES

To: ABBVIE INC.

Reel/Frame 030231/0808 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2008

From: BETEBENNER, DAVID A.; MARING, CLARENCE J.; ROCKWAY, TODD W.; COOPER, CURT S.; ANDERSON, DAVID D.; WAGNER, ROLF; ZHANG, RONG; MOLLA, AKHTERUZZAMAN; MO, HONGMEI; PILOT-MATIAS, TAMI J.; MASSE, SHERIE VL.; CARRICK, ROBERT J.; HE, WENPING; LU, LIANGJUN

To: ABBOTT LABORATORIES

Reel/Frame 020792/0292 →