IP Library Granted Patent US 9,428,469
Granted Patent B2
US 9,428,469 · App. 14/766,872 · Granted Aug 30, 2016

Antiviral compounds

Inventors: Qingjie Ding (Bridgewater, NJ); Nan Jiang (Pine Brook, NJ); Robert James Weikert (Clifton, NJ)
Assignee: HOFFMANN-LA ROCHE
C07D249/14C07D401/12C07D403/12C07D405/12
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Quick Facts
Patent No.
US 9,428,469
App. No.
14/766,872
Granted
Aug 30, 2016
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 (34)

1. A compound, selected from the group consisting of:

N3-(4-Bromo-3-chloro-5-trifluoromethyl-phenyl)-N5-(4-trifluoromethyl-benzyl)-1H-[1,2,4]triazole-3,5-diamine;

N3-(3,5-Dichloro-phenyl)-N5-furan-2-ylmethyl-1H-[1,2,4]triazole-3,5-diamine;

N3-(3,5-Dichloro-phenyl)-N5-(5-methyl-furan-2-ylmethyl)-1H-[1,2,4]triazole-3,5-diamine;

N5-(5-Chloro-2-trifluoromethyl-benzyl)-N3-(3,5-dichloro-phenyl)-1H-[1,2,4]triazole-3,5-diamine;

N5-(5-Chloro-pyridin-2-ylmethyl)-N3-(3,5-dichloro-phenyl)-1H-[1,2,4]triazole-3,5-diamine;

(5-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-pyridin-2-yl)-carbamic acid tert-butyl ester;

4-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzoic acid tert-butyl ester;

2-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzoic acid tert-butyl ester;

N5-Benzyl-N3-(3,5-dichloro-phenyl)-1H-[1,2,4]triazole-3,5-diamine;

N5-(6-Amino-pyridin-3-ylmethyl)-N3-(3,5-dichloro-phenyl)-1H-[1,2,4]triazole-3,5-diamine;

N3-(3,5-Dichloro-phenyl)-N5-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-[1,2,4]triazole-3,5-diamine;

4-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzoic;

3-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzoic acid;

2-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzoic acid;

N3-(3,5-Dichloro-phenyl)-N5-(4-methanesulfonyl-benzyl)-1H-[1,2,4]triazole-3,5-diamine;

4-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzonitrile;

4-{[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-N,N-dimethyl-benzenesulfonamide;

N-tert-Butyl-4-{[5-(3,5-dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzenesulfonamide;

N5-(3-Chloro-4-trifluoromethyl-benzyl)-N3-(3,5-dichloro-phenyl)-1H-[1,2,4]triazole-3,5-diamine;

N3-(3,5-Dichloro-phenyl)-N5-[4-(pyrrolidine-1-sulfonyl)-benzyl]-1H-[1,2,4]triazole-3,5-diamine;

N3-(3,5-Dichloro-phenyl)-N5-[4-(morpholine-4-sulfonyl)-benzyl]-1H-[1,2,4]triazole-3,5-diamine;

2,6-Dichloro-4-[5-(4-trifluoromethyl-benzylamino)-1H-[1,2,4]triazol-3-ylamino]-benzonitrile;

4-{[5-(3,5-Dichloro-4-cyano-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-methyl}-benzoic acid tert-butyl ester;

4-({5-[6-Chloro-4′-(propane-2-sulfonyl)-2-trifluoromethyl-biphenyl-4-ylamino]-2H-[1,2,4]triazol-3-ylamino}-methyl)-benzoic acid tert-butyl ester;

N3-(3,5-Dichloro-phenyl)-N5-(4-trifluoromethyl-benzyl)-1H-[1,2,4]triazole-3,5-diamine;

N3-(3,5-Dichloro-phenyl)-N5-(3-trifluoromethyl-benzyl)-1H-[1,2,4]triazole-3,5-diamine;

N3-(3,5-Dichloro-phenyl)-N5-(1-methanesulfonyl-piperidin-4-yl)-1H-[1,2,4]triazole-3,5-diamine;

4-[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-piperidine-1-carboxylic acid tert-butyl ester;

N3-(3,5-Dichloro-phenyl)-N5-piperidin-4-yl-1H-[1,2,4]triazole-3,5-diamine;

1-{4-[5-(3,5-Dichloro-phenylamino)-2H-[1,2,4]triazol-3-ylamino]-piperidin-1-yl}-ethanone; and

N3-(3,5-Dichloro-phenyl)-N5-pyrimidin-5-ylmethyl-1H-[1,2,4]triazole-3,5-diamine.

2. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 and a pharmaceutically acceptable excipient.

3. A method for the treatment of hepatitis C virus infection, comprising the step of administering a therapeutically effective amount of a compound according to claim 1 to a patient in need thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2015
From: WEIKERT, ROBERT J.; DING, QINGJIE; JIANG, NAN
To: HOFFMANN-LA ROCHE INC.
Reel/Frame 036643/0161 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2015
From: HOFFMANN-LA ROCHE INC.
To: F. HOFFMANN-LA ROCHE AG
Reel/Frame 036643/0265 →
Continuity (2)
Provisional Application 61772924 · Mar 5, 2013
Related Publication 20160009666A1 · Jan 14, 2016