IP Library Granted Patent US 8,779,141
Granted Patent B2
US 8,779,141 · App. 12/468,667 · Granted Jul 15, 2014

Viral inhibitors

Inventors: Johan Neyts (Kessel-Lo, BE); Gerhard Pürstinger (Innsbruck, AT); Erik De Clercq (Lovenjoel, BE)
Assignees: Gilead Sciences, Inc.; K.U. Leuven Research & Development; Gerhard Puerstinger
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Quick Facts
Patent No.
US 8,779,141
App. No.
12/468,667
Granted
Jul 15, 2014
Kind
B2
Abstract

The present invention relates to imidazo[4,5-c]pyridine compounds and pharmaceutical compositions for the treatment or prevention of viral infections, wherein the imidazo[4,5-c]pyridine compounds have the formula:

Claims (56)

1. A compound selected from the group consisting of

2-(2,6-Difluorophenyl)-5-[(2,6-difluorophenyl)methyl]-5H-imidazo[4,5-c]pyridine;

5-Benzyl-2-(2,6-difluorophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(2,6-Difluorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-Benzyl-2-phenyl-5H-imidazo[4,5-c]pyridine;

2-Phenyl-5-(3-phenylpropyl)-5H-imidazo[4,5-c]pyridine;

5-[(2-Chlorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(3-Chlorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(4-Chlorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(2-Methoxyphenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(3-Methoxyphenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(4-Methoxyphenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(4-Methylphenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(2-Fluorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(3-Fluorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(4-Fluorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(2-Methylphenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(3-Methylphenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

4-[(2-Phenyl-5H-imidazo[4,5-c]pyridin-5-yl)methyl ]-benzonitrile;

2-Phenyl-5-[[4-(trifluoromethyl)phenyl]methyl]-5H-imidazo[4,5-c]pyridine;

5-[(4-Chlorophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine hydrochloride;

5-[(5-Chloro-2-thienyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-(2-Naphthalenylmethyl)-2-phenyl-5H-imidazo[4,5-c]pyridine;

2-Phenyl-5-(4-phenylbutyl)-5H-imidazo[4,5-c]pyridine;

5-([1,1′-Biphenyl]-4-ylmethyl)-2-phenyl-5H-imidazo[4,5-c]pyridine;

2-Phenyl-5-(1-phenylethyl)-5H-imidazo[4,5-c]pyridine;

5-(1-Naphthalenylmethyl)-2-phenyl-5H-imidazo[4,5-c]pyridine;

2-(2,6-Difluorophenyl)-5-[(2,4-difluorophenyl)methyl]-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(2-fluorophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(2-chlorophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(3-chlorophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(4-chlorophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(2-pyridinyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(2-thienyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(1-naphthalenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(2-naphthalenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Iodophenyl)methyl]-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(3-fluorophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(3-methylphenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(3-methoxyphenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-(3-bromophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Chlorophenyl)methyl]-2-(3-bromophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Chlorophenyl)methyl]-2-(3-chlorophenyl)-5H-imidazo[4,5-c]pyridine;

5-(2-Phenoxy-ethyl)-2-phenyl-5H-imidazo[4,5-c]pyridine;

5-(3-Phenyl-prop-2-en-1-yl)-2-phenyl-5H-imidazo[4,5-c]pyridine;

2-(3-Bromophenyl)-5-[(4-iodophenyl)methyl]-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-[(phenylthio)methyl]-5H-imidazo[4,5-c]pyridine;

5-[(4-Bromophenyl)methyl]-2-[3-(trifluoromethyl)phenyl]-5H-imidazo[4,5-c]pyridine;

5-([1,1′-Biphenyl]-4-ylmethyl)-2-(2-fluorophenyl)-5H-imidazo[4,5-c]pyridine;

5-[(4-Chlorophenyl)methyl]-2-(2-fluorophenyl)-5H-imidazo[4,5-c]pyridine;

2-(2-Fluorophenyl)-5-[(4-iodophenyl)methyl]-5H-imidazo[4,5-c]pyridine;

2-phenyl-5-(pyridine-4-ylmethyl)-5H-imidazo[4,5-c]pyridine;

2-phenyl-5-(pyridine-3-ylmethyl)-5H-imidazo[4,5-c]pyridine;

2-phenyl-5-(pyridine-2-ylmethyl)-5H-imidazo[4,5-c]pyridine; and

5[[4-(1,1-Dimethylethyl)phenyl]methyl]-2-(2-fluorophenyl)-5H-imidazo[4,5-c]pyridine; or a stereoisomer thereof or a pharmaceutically acceptable salt thereof.

Assignments (7)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNMENT PREVIOUSLY RECORDED AT REEL: 036495 FRAME: 0004. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME AND ADDRESS.. Recorded Jan 4, 2018
From: GILEAD SCIENCES, INC.
To: KATHOLIEKE UNIVERSITEIT LEUVEN
Reel/Frame 045002/0531 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNMENT PREVIOUSLY RECORDED AT REEL: 023354 FRAME: 0033. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR AND ASSIGNEE NAME AND ADDRESS.. Recorded Jan 4, 2018
From: KATHOLIEKE UNIVERSITEIT LEUVEN
To: GILEAD SCIENCES, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; PUERSTINGER, GERHARD
Reel/Frame 045000/0429 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 3, 2018
From: NEYTS, JOHAN; DE CLERCQ, ERIK
To: KATHOLIEKE UNIVERSITEIT LEUVEN
Reel/Frame 044523/0603 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME AND ADDRESS PREVIOUSLY RECORDED ON REEL 023354 FRAME 0001. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE NAME --KATHOLIEKE UNIVERSITEIT LEUVEN-- AND ADDRESS --KU LEUVEN R&D, WAAISTRAAT 6-BUS 5105, 3000 LEUVEN, BELGIUM--. Recorded Jan 3, 2018
From: PUERSTINGER, GERHARD
To: GILEAD SCIENCES, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; PUERSTINGER, GERHARD
Reel/Frame 044994/0040 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 4, 2015
From: GILEAD SCIENCES, INC.
To: K.U. LEUVEN RESEARCH & DEVELOPMENT
Reel/Frame 036495/0004 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 9, 2009
From: K.U. LEUVEN RESEARCH & DEVELOPMENT
To: GILEAD SCIENCES, INC.; K.U. LEUVEN RESEARCH & DEVELOPMENT; PUERSTINGER, GERHARD
Reel/Frame 023354/0033 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 9, 2009
From: PUERSTINGER, GERHARD
To: GILEAD SCIENCES, INC.; K.U. LEUVEN RESEARCH & DEVELOPMENT; PUERSTINGER, GERHARD
Reel/Frame 023354/0001 →
Priority Claims (2)
GB 0215293.2 · Jul 3, 2002 · national
GB 0313251.1 · Jun 10, 2003 · national
Continuity (2)
Division 10519756
Related Publication 20100004281A1 · Jan 7, 2010