US 9,540,345 B2Granted

Antiviral compounds

AssigneeHoffmann-La Roche Inc.

InventorsSteven Joseph Berthel, Zhi Chen, Feng Chi, Elbert Chin, David Shawn Erickson, Stephen Deems Gabriel, Buelent Kocer, Eric Mertz, Jean-Marc Plancher, Robert J. Weikert

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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.

Claims2

Dependent claims

A compound selected from the group consisting of:

N3-[3,5-Dichloro-4-(6-methoxy-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(5-methanesulfonyl-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1H-pyridin-2-one;
N3-[4-(6-Amino-pyridin-3-yl)-3,5-dichloro-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[4-(2-Amino-pyrimidin-5-yl)-3,5-dichloro-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(2-methoxy-pyridin-4-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
4-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1H-pyridin-2-one;
N-{5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-pyridin-2-yl}-methanesulfonamide;
N5-[3-Fluoro-4-(6-fluoro-pyridin-3-yl)-5-trifluoromethyl-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N5-(3-Fluoro-4-pyridin-3-yl-5-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(6-methanesulfonyl-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
6-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester;
N3-(3-Chloro-4-pyridazin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3-Chloro-4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3-Chloro-4-(2-methyl-2H-[1,2,4]triazol-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3,5-Dichloro-4-pyrazol-1-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
4-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;
N3-[3,5-Dichloro-4-(1,2,3,6-tetrahydro-pyridin-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-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;
N3-[3-Chloro-4-(1,2,3,6-tetrahydro-pyridin-4-yl)-5-trifluoromethyl-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N5-(3,5-Dichloro-4-[1,2,4]triazolo[4,3-a]pyridin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N-{3-Chloro-4-[6-(propane-2-sulfonyl)-pyridin-3-yl]-5-trifluoromethyl-phenyl}-4H-[1,2,4]triazole-3,5-diamine;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-sulfonic acid tert-butylamide;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-sulfonic acid (2,2,2-trifluoro-1,1-dimethyl-ethyl)-amide;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-sulfonic acid adamantan-1-ylamide;
N3-[2-Chloro-4′-(4-methyl-piperazin-1-yl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3-Chloro-4-pyridazin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
1-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-phenyl]-1H-pyridin-2-one;
1-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-phenyl]-1H-pyridin-2-one;
1-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1H-pyridin-2-one;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-carboxylic acid methylamide;
N3-(3,5-Dichloro-4-pyridazin-4-yl-phenyl)-1H-[1,2,4]-triazole-3,5-diamine;
1-{3-[4-(5-Amino-1H-[1,2,4]triazol-3-yl amino)-2,6-dichloro-phenyl]-thiophen-2-yl}-ethanone;
N3-(3,5-Dichloro-4-pyridin-4-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(5-chloro-thiophen-2-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3,5-Dichloro-4-pyridin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(1H-pyrazol-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3,5-Dichloro-4-pyrimidin-5-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(2-methoxy-pyrimidin-5-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(6-trifluoromethyl-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(5-chloro-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
and
N3-[3,5-Dichloro-4-(6-methoxy-pyridin-2-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine,
or a pharmaceutically acceptable salt thereof.

42 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/766,905Filed 3 Mar 2014 · us provisional application
Priority: 5 Mar 2013
Published: US 2015/0368228 A124 Dec 2015
Granted: 10 Jan 2017
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/4196
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,2,4-Triazoles
A61K 31/437
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring…
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole

Family

Application61/772,943Us provisional application · filed 5 Mar 2013
US 2015/0368228 A1Pre-grant publication · published 24 Dec 2015
US 9,540,345 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound selected from the group consisting of:

N3-[3,5-Dichloro-4-(6-methoxy-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(5-methanesulfonyl-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1H-pyridin-2-one;
N3-[4-(6-Amino-pyridin-3-yl)-3,5-dichloro-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[4-(2-Amino-pyrimidin-5-yl)-3,5-dichloro-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(2-methoxy-pyridin-4-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
4-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1H-pyridin-2-one;
N-{5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-pyridin-2-yl}-methanesulfonamide;
N5-[3-Fluoro-4-(6-fluoro-pyridin-3-yl)-5-trifluoromethyl-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N5-(3-Fluoro-4-pyridin-3-yl-5-trifluoromethyl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(6-methanesulfonyl-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
6-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester;
N3-(3-Chloro-4-pyridazin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3-Chloro-4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3-Chloro-4-(2-methyl-2H-[1,2,4]triazol-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3,5-Dichloro-4-pyrazol-1-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
4-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;
N3-[3,5-Dichloro-4-(1,2,3,6-tetrahydro-pyridin-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-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;
N3-[3-Chloro-4-(1,2,3,6-tetrahydro-pyridin-4-yl)-5-trifluoromethyl-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N5-(3,5-Dichloro-4-[1,2,4]triazolo[4,3-a]pyridin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N-{3-Chloro-4-[6-(propane-2-sulfonyl)-pyridin-3-yl]-5-trifluoromethyl-phenyl}-4H-[1,2,4]triazole-3,5-diamine;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-sulfonic acid tert-butylamide;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-sulfonic acid (2,2,2-trifluoro-1,1-dimethyl-ethyl)-amide;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-sulfonic acid adamantan-1-ylamide;
N3-[2-Chloro-4′-(4-methyl-piperazin-1-yl)-6-trifluoromethyl-biphenyl-4-yl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3-Chloro-4-pyridazin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
1-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-phenyl]-1H-pyridin-2-one;
1-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-phenyl]-1H-pyridin-2-one;
1-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-phenyl]-1H-pyridin-2-one;
5-[4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethyl-phenyl]-pyridine-2-carboxylic acid methylamide;
N3-(3,5-Dichloro-4-pyridazin-4-yl-phenyl)-1H-[1,2,4]-triazole-3,5-diamine;
1-{3-[4-(5-Amino-1H-[1,2,4]triazol-3-yl amino)-2,6-dichloro-phenyl]-thiophen-2-yl}-ethanone;
N3-(3,5-Dichloro-4-pyridin-4-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(5-chloro-thiophen-2-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3,5-Dichloro-4-pyridin-3-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(1H-pyrazol-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-(3,5-Dichloro-4-pyrimidin-5-yl-phenyl)-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(2-methoxy-pyrimidin-5-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(6-trifluoromethyl-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
N3-[3,5-Dichloro-4-(5-chloro-pyridin-3-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine;
and
N3-[3,5-Dichloro-4-(6-methoxy-pyridin-2-yl)-phenyl]-1H-[1,2,4]triazole-3,5-diamine,
or a pharmaceutically acceptable salt thereof.

42 more elements

Facts

Application

14/766,905Filed 3 Mar 2014 · us provisional application

Priority

5 Mar 2013

Published

US 2015/0368228 A124 Dec 2015

Granted

10 Jan 2017

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/4196
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,2,4-Triazoles
A61K 31/437
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring…
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole