IP Library › Granted Patent US 9,693,997
Granted Patent B2
US 9,693,997 · App. 14/768,915 · Granted Jul 4, 2017

Antiviral compounds

Inventors: Joseph Anthony Bilotta (Nutley, NJ); Zhi Chen (Livingston, NJ); Feng Chi (Basking Ridge, NJ); Elbert Chin (San Mateo, CA); Qingjie Ding (Bridgewater, NJ); Shawn David Erickson (Leonia, NJ); Stephen Deems Gabriel (Morristown, NJ); Nan Jiang (Pine Brook, NJ); Buelent Kocer (Maulburg, DE); Eric Mertz (Fair lawn, NJ); Jean-Marc Plancher (Hagenthal-le-Bas, FR); Robert J. Weikert (Basel, CH); Jing Zhang (Parsippany, NJ); Qiang Zhang (East Brunswick, NJ)
Assignee: HOFFMANN-LA ROCHE INC.
A61K31/4196A61K31/428A61K31/454A61K31/496A61K31/538A61K31/5377A61K31/541A61K31/5415A61K45/06C07D249/14C07D401/12C07D403/12C07D405/12C07D411/12C07D413/12C07D417/12C07D491/107C07D495/04
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Quick Facts
Patent No.
US 9,693,997
App. No.
14/768,915
Granted
Jul 4, 2017
Kind
B2
Abstract

The present invention discloses compounds of Formula I: wherein the variables in Formula I are defined as described herein. Also disclosed are pharmaceutical compositions containing such compounds and methods for using the compounds of Formula I in the prevention or treatment of HCV infection.

Claims (327)

1. A compound of formula I:

wherein:

A is phenyl, naphthyl, or bicyclic unsaturated or partially saturated heteroaryl, substituted with one or more A;

each A is independently lower alkyl, halo, lower alkoxy, S(═O) 2 (CH 2 ) m A″, C(═O)NHA″, NHC(O)A″, —O(CH 2 ) m A″, (CHA 1 ) m NHS(═O) 2 A 1 ; or S(═O) 2 NHA″;

each A″ is independently, heterocycloalkyl or heteroaryl, optionally substituted with one or more A′″;

each A′″ is independently hydroxy, lower alkyl, oxo, C(═O)OA 1 , halo loweralkyl,

each A 1 is independently H, lower alkyl, halo loweralkyl, amino, lower alkoxy,

each m is independently 0, 1, 2, or 3;

R 1 is H, halo, lower alkyl, halo loweralkyl, SF 5 , and

R 2 is H, halo, lower alkyl, halo loweralkyl,

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein A is phenyl.

3. The compound of claim 2 , wherein R 1 is halo loweralkyl.

4. The compound of claim 3 , wherein R 2 is halo.

5. The compound of claim 2 , wherein R 1 is halo.

6. The compound of claim 5 , wherein R 2 is halo.

7. The compound of claim 1 , wherein A′ is S(═O) 2 (CH 2 ) m A″ or (CH 2 ) m S(═O) 2 A″.

8. The compound of claim 1 , wherein A′ is lower alkyl, halo, or lower alkoxy.

9. The compound of claim 1 , wherein A′ is C(═O)NHA″ or NHC(═O)A″.

10. The compound of claim 1 , wherein A′ is (CHA 1 ) m NHS(═O) 2 A 1 or S(═O) 2 NHA″.

11. The compound of claim 1 , wherein A′ is O(CH 2 ) m A″.

12. A compound selected from the group consisting of:

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonyl]-piperidine-1-carboxylic acid tert-butyl ester;

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonylmethyl]-piperidine-1-carboxylic acid tert-butyl ester;

(S)-1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluormethyl-biphenyl-4-sulfonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester;

N 3 -{6-Chloro-2-trifluoromethyl-4′-[1-(3,3,3-trifluoro-propyl)-piperidine-4-sulfonyl]-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[1-(3,3-dimethyl-butyl)-piperidine-4-sulfonyl]-2-trifluoromethyl-biphenyl-4-yl}-H-[1,2,4]triazole-3,5-diamine;

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonyl]-piperidine-1-carboxylic acid tert-butyl ester;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonylmethyl]-piperidine-1-carboxylic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-carboxylic acid tert-butylamide;

Pentanoic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-amide;

N 3 -[4-(2-tert-Butyl-1,1-dioxo-2,3-dihydro-1H-1λ 6 -benzo[d]isothiazol-6-yl)-3-chloro-5-trifluoromethyl-phenyl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-2-trifluoromethyl-4′-[1-(3,3,3-trifluoro-propyl)-piperidine-3-sulfonyl]-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-ylmethyl]-methanesulfonamide;

N—{(S)-1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-yl]-ethyl}-methanesulfonamide;

N 3 -(2,6-Dichloro-4′-methanesulfonyl-3′-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[3,5-Dichloro-4-(1-methanesulfonyl-1H-indol-4-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonyl]-piperazine-1-carboxylic acid tert-butyl ester;

N 3 -{6-Chloro-4′-[1-(3,3-dimethyl-butyl)-piperidine-3-sulfonyl]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-4-methyl-6′-trifluoromethyl-biphenyl-3-sulfonic acid tert-butylamide;

N 3 -[2-Chloro-4′-methoxy-3′-(propane-2-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2-Chloro-4′-(piperidine-4-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-3-yloxy]-piperidine-1-carboxylic acid tert-butyl ester;

N 3 -[2-Chloro-4′-(4-methyl-piperazine-1-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2-Chloro-6-fluoro-4′-(propane-2-sulfonyl)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N—{(R)-1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-yl]-ethyl}-methanesulfonamide;

N 3 -[2-Chloro-4′-(piperidin-3-ylmethanesulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-butyronitrile;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonic acid ((S)-1-pyrolidin-2-ylmethyl)-amide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-2-fluoro-biphenyl-4-yl]-methanesulfonamide;

N 3 -[2-Chloro-4′-(piperidine-3-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-6-fluoro-4′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-4′-methanesufonylmethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[4′-(Azetidin-3-ylmethoxy)-2,6-dichloro-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2-Chloro-4′-(piperazine-1-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-fluoro-biphenyl-4-sulfonic acid dimethylamide;

N 3 -[2-Chloro-4′-((S)-1-pyrrolidin-2-ylmethanesulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2-Chloro-4′-(morpholine-4-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[4′-(Azetidin-3-ylmethoxy)-2-chloro-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N-{2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-yl]-ethyl}-methanesulfonamide;

5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-amide;

N 3 -[2-Chloro-4′-(piperidin-4-ylmethanesulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2-Chloro-3′-(piperidin-4-yloxy)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[3,5-Dichloro-4-(1-methanesulfonyl-1H-indol-5-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;

1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-pyrrolidin-2-one;

N 3 -[3-Chloro-4-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-5-trifluoromethyl-phenyl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2-Chloro-4′-(1,1-dioxo-1λ 6 -thiomorpholine-4-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-3-fluoro-biphenyl-4-yl]-methanesulfonamide;

6-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-4H-benzo[1,4]oxazin-3-one;

N 3 -(2,6-Dichloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[4′-(4-Amino-butoxy)-2,6-dichloro-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

compound with trifluoro-acetic acid;

N 3 -(4′-Amino-2,6-dichloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

(S)-1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonyl]-pyrrolidine-2-carboxylic acid;

N 3 -[3,5-Dichloro-4-(2,2-dimethyl-4,4-dioxo-3,4-dihydro-2H-4λ 6 -benzo[1,4]oxathiin-6-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;

Pentanoic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-biphenyl-4-yl]-amide;

5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-biphenyl-4-yl]-amide;

N 3 -Biphenyl-4-yl-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[1-(3,3-dimethyl-butyl)-piperidin-3-ylmethanesulfonyl]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[1-(3,3-dimethyl-butyl)-piperidin-4-ylmethanesulfonyl]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[4′-(tert-Butylamino-methyl)-2-chloro-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-cloro-2′-trifluoromethyl-biphenyl-4-sulfonyl]-azetidine-1-carboxylic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (3-methyl-oxetan-3-yl)-amide;

N 3 -[6-Chloro-4′-(3-methyl-butane-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-(3,3-difluoro-pyrrolidine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonyl]-3-methyl-azetidin-3-ol;

N 3 -(6-Chloro-4′-cyclopropylmethanesulfonyl-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-(2-methyl-propane-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonyl]-4-methyl-piperidin-4-ol;

N 3 -[4′-(Azetidine-3-sulfonyl)-6-chloro-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonyl]-3-methyl-pyrrolidin-3-ol;

N 3 -[6-Chloro-4′-(2-oxa-6-aza-spiro[3.3]heptane-6-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 5 -(2-Fluoro-4′-methanesulfonyl-6-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 5 -[2-Fluoro-4′-(propane-2-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′-fluoro-6′-trifluoromethyl-biphenyl-4-sulfonic acid methylamide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-2-methoxy-acetamide;

N 5 -(2-Fluoro-3′-methanesulfonyl-6-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′-fluoro-6′-trifluoromethyl-biphenyl-4-sulfonic acid dimethylamide;

N 5 -(2,6-Difluoro-4′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 5 -[2,6-Difluoro-4′-(morpholine-4-sulfonyl)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 5 -[2-Fluoro-4′-(morpholine-4-sulfonyl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′-fluoro-6′-trifluoromethyl-biphenyl-4-carbonitrile;

N 5 -(2,6-Difluoro-3′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′-fluoro-6′-trifluoromethyl-biphenyl-3-sulfonic acid methylamide;

Tetrahydro-pyran-4-carboxylic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-amide;

N 3 -(2,6-Dichloro-4′-nitro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diaminetrifluoro-acetic acid;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′-fluoro-6′-trifluoromethyl-biphenyl-3-sulfonic acid dimethylamide;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′-fluoro-6′-trifluoromethyl-biphenyl-4-carboxylic acid dimethylamide;

N 5 -(2-Fluoro-4′-methoxy-6-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′,6′-difluoro-biphenyl-4-carbonitrile;

N 5 -(2-Fluoro-4′-trifluoromethanesulfonyl-6-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2′-fluoro-6′-trifluoromethyl-biphenyl-3-carbonitrile;

N 3 -(4-Methanesulfonyl-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-4′-trifluoromethoxy-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6,3′-Trichloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-carbonitrile;

N 3 -(2,6-Dichloro-4′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(3,5-Dichloro-4-naphthalen-1-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6,4′-Trichloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-4′-methyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-4′-methoxy-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-4′-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-3′-methoxy-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6,2′-Trichloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6,3′,4′-Tetrachloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-carbonitrile;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-2-carbonitrile;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-4,2′,6′-trichloro-biphenyl-3-carbonitrile;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-carboxylic acid;

1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-ethanone;

N 3 -(2,6-Dichloro-3′-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6,2′,3′-Tetrachloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-carboxylic acid methyl ester;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-methanesulfonamide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-yl]-methanesulfonamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-carboxylic acid dimethylamide;

N 3 -(2,6-Dichloro-3′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-carboxylic acid dimethylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-carboxylic acid methylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-carboxylic acid methylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-sulfonic acid methylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-sulfonic acid methylamide;

N 3 -(2,6-Dichloro-2′-methoxy-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-3′-fluoro-4′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2,6-Dichloro-4′-(propane-2-sulfonyl)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-sulfonic acid dimethylamide;

N 3 -(2,6,2′,4′-Tetrachloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

{2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester;

N 3 -[6-Chloro-4′-(2-methylamino-ethoxy)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-(1,2,2,6,6-pentamethyl-piperidin-4-ylsulfanyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

{2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-cloro-2′-trifluoromethyl-biphenyl-4-yloxy]-1,1-dimethyl-ethyl}-methyl-carbamic acid tert-butyl ester;

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester;

N 3 -[6-Chloro-4′-(piperidin-3-yloxy)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[1-(3,3-dimethyl-butyl)-piperidin-3-yloxy]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-(1-methyl-piperidin-3-yloxy)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-2-trifluoromethyl-4′-[1-(3,3,3-trifluoro-propyl)-piperidin-3-yloxy]-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

{2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yloxy]-ethyl}-carbamic acid tert-butyl ester;

N 3 -[4′-(2-Amino-ethoxy)-6-chloro-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[2-(3,3-dimethyl-butylamino)-ethoxy]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(4′-{2-[Bis-(3,3-dimethyl-butyl)-amino]-ethoxy}-6-chloro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester;

N 3 -[6-Chloro-4′-(piperidin-4-yloxy)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-2-trifluoromethyl-4′-[1-(3,3,3-trifluoro-propyl)-piperidin-4-yloxy]-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[1-(2-methanesulfonyl-ethyl)-piperidin-4-yloxy]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[1-(3-methanesulfonyl-propyl)-piperidin-4-yloxy]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -{6-Chloro-4′-[1-(2-methoxy-ethyl)-piperidin-4-yloxy]-2-trifluoromethyl-biphenyl-4-yl}-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-4′-fluoro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-2′-fluoro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-3′,4′-difluoro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-3′-fluoro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2′-Fluoro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(4′-Fluoro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(3′,4′-Difluoro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2′-Chloro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-4′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,2′-Dichloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-2′-fluoro-4′-methylsulfanyl-biphenyl-4-yl)-H-[1,2,4]triazole-3,5-diamine;

N 3 -(2-Chloro-2′-fluoro-4′-methanesulfonyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-carboxylic acid amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-carboxylic acid amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-sulfonic acid (2-hydroxy-ethyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonic acid (2-hydroxy-ethyl)-amide;

2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonyl]-ethanol;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-3-methoxy-2′-trifluoromethyl-biphenyl-4-sulfonyl amino]-piperidine-1-carboxylic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-sulfonic acid tert-butylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (2,2,2-trifluoro-1,1-dimethyl-ethyl)-amide;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonyl]-piperazine-1-carboxylic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-3-methoxy-2′-trifluoromethyl-biphenyl-4-sulfonic acid (4-hydroxy-cyclohexyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid (tetrahydro-pyran-4-yl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid cyclopropylamide;

N 3 -[6-Chloro-4′-(pyrrolidine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (3-hydroxy-cyclobutyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (3-hydroxy-cyclobutyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (3-hydroxy-cyclobutyl)-amide;

4′-(5-amino-1H-1,2,4-triazol-3-ylamino)-2′-chloro-N-(2-hydroxyethyl)-4-methoxy-6′-(trifluoromethyl)biphenyl-3-sulfonamide

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid (2-hydroxy-ethyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-3-sulfonic acid tert-butylamide;

N 3 -[6-Chloro-4′-methoxy-3′-(morpholine-4-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-3-methoxy-2′-trifluoromethyl-biphenyl-4-sulfonic acid piperidin-4-ylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid amide;

N 3 -[6-Chloro-4′-(propane-2-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-methoxy-3′-(piperazine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-(4,4-difluoro-piperidine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (4-hydroxy-cyclohexyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid dimethylamide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-ylmethyl]-methanesulfonamide;

N 3 -(6-Chloro-4′-methanesulfonyl-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(6-Chloro-4′-cyclopropanesulfonyl-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-carboxylic acid methylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid (4-hydroxy-cyclohexyl)-amide;

1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonyl]-azetidin-3-ol;

N 3 -[6-Chloro-3′-(pyrrolidine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-trifluoromethoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid tert-butylamide;

1-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonyl]-piperidin-4-ol;

N 3 -(6-Chloro-3′-methanesulfonyl-2-trifluoromethyl-biphenyl-4-yl)-H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-3-sulfonic acid tert-butyl-methyl-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-3-sulfonic acid amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-3-sulfonic acid dimethylamide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-3-ylmethyl]-methanesulfonamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-carboxylic acid tert-butyl ester;

N 3 -(6-Chloro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-carboxylic acid;

N 3 -[6-Chloro-4′-methoxy-3′-(pyrrolidine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid piperidin-4-ylamide

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonylamino]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (1-methyl-cyclopropyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (3-methyl-azetidin-3-yl)-amide;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonyl]-4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester;

{2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonylamino]-ethyl}-methyl-carbamic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (1-isopropyl-3-methyl-azetidin-3-yl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (1-isopropyl-3-methyl-azetidin-3-yl)-amide;

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonylamino]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (2-methylamino-ethyl)-amide;

N 3 -[6-Chloro-4′-(4,7-diaza-spiro[2.5]octane-4-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid (3-methyl-azetidin-3-yl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid tert-butylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-3-trifluoromethoxy-2′-trifluoromethyl-biphenyl-4-sulfonic acid tert-butylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonic acid tert-butylamide;

N 3 -[2,6-Dichloro-4′-(pyrrolidine-1-sulfonyl)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonylamino]-piperidine-1-carboxylic acid tert-butyl ester;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-4-methoxy-6′-trifluoromethyl-biphenyl-3-sulfonic acid piperidin-4-ylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid tert-butyl-(2,2,2-trifluoro-ethyl)-amide;

N 3 -[6-Chloro-4′-(3,3-difluoro-azetidine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid (1-cyano-cyclopropyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-4-methoxy-6′-trifluoromethyl-biphenyl-3-sulfonic acid (1-acetyl-piperidin-4-yl)-amide;

N*3*-[6-Chloro-4′-(propane-2-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine

N 3 -(6-Chloro-3′-isopropoxy-4′-methoxy-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(4′-tert-Butoxy-6-chloro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(6-Chloro-4′-methoxy-2,3′-bis-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6′-Chloro-4,4″-bis-(pyrrolidine-1-sulfonyl)-[1,1′;2′,1″]terphenyl-4′-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-(3-fluoro-azetidine-1-sulfonyl)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid piperidin-4-yl-(2,2,2-trifluoro-ethyl)-amide;

4,4-Difluoro-cyclohexanecarboxylic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yl]-amide;

[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yl]-carbamic acid 1-tert-butyl-azetidin-3-yl ester;

[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yl]-carbamic acid propyl ester;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yl]-3-(tetrahydro-pyran-4-yl)-propionamide;

1,1-Dioxo-hexahydro-1λ 6 -thiopyran-4-carboxylic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yl]-amide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yl]-2-(1,1-dioxo-1λ 6 -thiomorpholin-4-yl)-acetamide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-4-yl]-2-morpholin-4-yl-acetamide;

N-[4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-6′-fluoro-2′-trifluoromethyl-biphenyl-4-yl]-methanesulfonamide;

N-[4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-6′-fluoro-2′-trifluoromethyl-biphenyl-3-yl]-methanesulfonamide;

N 5 -(6,3′-Difluoro-2-trifluoromethyl-biphenyl-4-yl)-H-[1,2,4]triazole-3,5-diamine;

N 5 -(6,4′-Difluoro-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 5 -(6-Fluoro-2,4′-bis-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 5 -(6-Fluoro-4′-methyl-2-trifluoromethyl-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4′-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-6′-fluoro-2′-trifluoromethyl-biphenyl-3-carboxylic acid methylamide;

N 5 -(3-Fluoro-4-naphthalen-2-yl-5-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;

4,4-Difluoro-cyclohexanecarboxylic acid [4′-(5-amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-amide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yl]-isobutyramide;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-3-yl]-isobutyramide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-sulfonic acid amide;

5-[4-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1,3-dihydro-indol-2-one;

5-[4-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1,3-dihydro-benzoimidazol-2-one;

6-[4-(5-Amino-2H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1,3-dihydro-indol-2-one;

N 5 -[3,5-Dichloro-4-(1H-indazol-5-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2′,6′-Dichloro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 5 -[2,6-Dichloro-4′-(piperidin-3-yloxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxymethyl]-azetidine-1-carboxylic acid tert-butyl ester;

{2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester;

N 3 -[2,6-Dichloro-4′-(piperidin-4-yloxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2,6-Dichloro-4′-(2-methylamino-ethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2,6-Dichloro-4′-(2-pyrrolidin-2-yl-ethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2,6-Dichloro-4′-((S)-1-pyrrolidin-2-ylmethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

2-{2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-ethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester;

(R)-2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester;

4-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-piperidine-1-carboxylic acid tert-butyl ester;

N 3 -[2,6-Dichloro-4′-(2-dimethylamino-ethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[6-Chloro-4′-((S)-1-pyrrolidin-2-ylmethoxy)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2,6-Dichloro-4′-((S)-pyrrolidin-3-yloxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2,6-Dichloro-4′-((R)-1-pyrrolidin-2-ylmethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-di amine;

(S)-3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester;

N 3 -[2,6-Dichloro-4′-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

(R)-2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxymethy]-pyrrolidine-1-carboxylic acid tert-butyl ester;

[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-acetic acid tert-butyl ester;

(S)-2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester;

N 3 -[2,6-Dichloro-4′-(2-methoxy-ethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine

N 3 -[6-Chloro-4′-((R)-1-pyrrolidin-2-ylmethoxy)-2-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

(S)-2-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester;

N 3 -[2,6-Dichloro-4′-(2-morpholin-4-yl-ethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

3-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-propane-1,2-diol;

N 3 -[2,6-Dichloro-4′-(3-morpholin-4-yl-propoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

N 3 -[2,6-Dichloro-4′-(pyridin-2-ylmethoxy)-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;

[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′,6′-dichloro-biphenyl-4-yloxy]-acetic acid;

N 3 -(2,6-Dichloro-4′-fluoro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N 3 -(2,6-Dichloro-2′-fluoro-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

N*3*-(4′-Methanesulfonyl-2-pentafluorosulfur-biphenyl-4-yl)-1H-[1,2,4]triazole-3,5-diamine

N 3 -[2,6-Dichloro-4′-(1,1-dioxo-λ 6 -isothiazolidin-2-yl)-biphenyl-4-yl]-H-[1,2,4]triazole-3,5-diamine;

N-[4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-2′-trifluoromethyl-biphenyl-3-yl]-methanesulfonamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-3-fluoro-2′-trifluoromethyl-biphenyl-4-carboxylic acid methylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-fluoro-2′-trifluoromethyl-biphenyl-3-carboxylic acid methylamide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-3-fluoro-2′-trifluoromethyl-biphenyl-4-carboxylic acid (2-hydroxy-ethyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-fluoro-2′-trifluoromethyl-biphenyl-3-carboxylic acid (2-hydroxy-ethyl)-amide;

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2′-chloro-6′-trifluoromethyl-biphenyl-4-sulfonic acid oxetan-3-ylamide; and

4′-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-6′-chloro-4-methoxy-2′-trifluoromethyl-biphenyl-3-sulfonic acid (1-isopropyl-piperidin-4-yl)-amide,

or a pharmaceutically acceptable salt thereof.

13. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

14. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 12 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

15. A method for treating a Hepatitis C Virus (HCV) infection, comprising the step of administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.

16. The method of claim 15 , further comprising the step administering a combination of antiviral agents that inhibits replication of HCV.

17. The method of claim 15 , further comprising the step of administering an immune system modulator or an antiviral agent that inhibits replication of HCV, or a combination thereof.

18. The method of claim 17 , wherein the immune system modulator is an interferon or a chemically derivatized interferon.

19. The method of claim 17 , wherein the antiviral agent is selected from the group consisting of a HCV protease inhibitor, a HCV polymerase inhibitor, a HCV helicase inhibitor and a HCV NS5A inhibitor, or any combination thereof.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 15, 2017
From: HOFFMANN-LA ROCHE INC.
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 042379/0322 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 15, 2017
From: KOCER, BUELENT; PLANCHER, JEAN-MARC
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 042379/0540 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 15, 2017
From: F. HOFFMANN-LA ROCHE AG
To: HOFFMANN-LA ROCHE INC.
Reel/Frame 042379/0625 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 15, 2017
From: WEIKERT, ROBERT J.; ZHANG, QIANG; CHIN, ELBERT; MERTZ, ERIC; CHI, FENG; ZHANG, JING; BILOTTA, JOSEPH ANTHONY; JIANG, NAN; DING, QINGJIE; ERICKSON, SHAWN DAVID; CHEN, ZHI; GABRIEL, STEPHEN DEEMS
To: HOFFMANN-LA ROCHE, INC.
Reel/Frame 042464/0176 →
Continuity (2)
Provisional Application 61773221 · Mar 6, 2013
Related Publication 20160000760A1 · Jan 7, 2016