US 6,720,333 B2 · Amide substituted imidazopyridines

Abstract

Imidazopyridine compounds that contain amide functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.

Claims45

Dependent claims

A compound of the formula (I):

wherein
X is ethylene, propylene, or butylene;
Y is —CO—;
Z is a bond;
R1 is aryl, heteroaryl, C1-10 alkyl, or C2-10 alkenyl, each of which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of:
-alkyl;
-aryl;
-substituted aryl;
-heteroaryl;
—O-alkyl;
—O-(alkyl)0-1 aryl;
—CO—O-alkyl;
-halogen;
-haloalkyl;
-haloalkoxy;
and
—CN;
R2 is selected from the group consisting of:
-hydrogen;
—C1-10 alkyl;
and
—C1-10 alkyl-O—C1-10 alkyl;
R3 and R4 are independently selected from the group consisting of hydrogen, and methyl;
R5 is H or C1-10 alkyl, or R5 can join with X to form a ring;
or a pharmaceutically acceptable salt thereof.

22 more elements

A compound selected from:

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}pentanamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclohexanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-fluorobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-thien-2-ylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-phenylpropanamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-6-chloronicotinamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}nicotinamide;
(1R*,2R*)-N-{3-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl)-2-phenylcyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-(benzyloxy)acetamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-naphthamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-(trifluoromethyl)benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzamide;
and
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethoxy)benzamide;
or a pharmaceutically acceptable salt thereof.

17 more elements

A compound selected from:

1-{2-[1-(cyclopropylcarbonyl)piperidin-4-yl]ethyl}-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-pentanoylpiperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine;
1-[2-(1-benzoylpiperidin-4-yl)ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
1-{2-[1-(cyclohexylcarbonyl)piperidin-4-yl]ethyl}-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(phenylacetyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-1-{2-[1-(4-fluorobenzoyl)piperidin-4-yl)ethyl}-6,7-dimethyl-1H-imidazo[4,5-c)pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(thien-2-ylacetyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-1-{2-[1-(3-cyanobenzoyl)piperidin-4-yl]ethyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(3-phenylpropanoyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
1-(2-{1-[(6-chloropyridin-3-yl)carbonyl]piperidin-4-yl}ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-{[(1R*,2R*)-2-phenylcyclopropyl]carbonyl}piperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine;
1-(2-{1-[(benzyloxy)acety]piperidin-4-yl}ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(2-naphthoyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-(2-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}ethyl)-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-(2-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}ethyl)-1H-imidazo[4,5-c]pyridin-4-amine;
and
2-(ethoxymethyl)-6,7-dimethyl-1-(2-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}ethyl)-1H-imidazo[4,5-c]pyridin-4-amine;
or a pharmaceutically acceptable salt thereof.

15 more elements

A compound selected from:

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]cyclopropanecarboxamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]pentanamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]cyclohexanecarboxamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-phenylacetamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-fluorobenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-thien-2-ylacetamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-cyanobenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-cyanobenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-phenylpropanamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-methoxybenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-methoxybenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-6-chloronicotinamide;
(1R*,2R*)-N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-phenylcyclopropanecarboxamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-naphthamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(trifluoromethyl)benzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-(trifluoromethyl)benzamide;
and
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-(trifluoromethoxy)benzamide;
or a pharmaceutically acceptable salt thereof.

16 more elements

A compound selected from:

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}cyclopropanecarboxamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}pentanamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}benzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}cyclohexanecarboxamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-phenylacetamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-fluorobenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-thien-2-ylacetamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-cyanobenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-cyanobenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-phenylpropanamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-methoxybenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-methoxybenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-6-chloronicotinamide;
(1R*,2R*)-N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-phenylcyclopropanecarboxamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-(benzyloxy)acetamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-naphthamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-(trifluoromethyl)benzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(trifluoromethyl)benzamide;
and
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(trifluoromethoxy)benzamide;
or a pharmaceutically acceptable salt thereof.

18 more elements

A compound selected from:

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]cyclopropanecarboxamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]pentanamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]benzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]cyclohexanecarboxamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylacetamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-fluorobenzamide,
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-thien-2-ylacetamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-cyanobenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyanobenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-phenylpropanamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-methoxybenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-methoxybenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-6-chloronicotinamide;
(1R*,2R*)-N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylcyclopropanecarboxamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-(benzyloxy)acetamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-naphthamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(trifluoromethyl)benzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethyl)benzamide
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethoxy)benzamide;
2-{[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}-2-oxoethyl acetate;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1,3-benzodioxole-5-carboxamide;
methyl 4-({[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}carbonyl)benzoate;
and
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]adamantane-1-carboxamide;
or a pharmaceutically acceptable salt thereof.

22 more elements

A compound selected from:

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclohexanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-fluorobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-thien-2-ylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-cyanobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-cyanobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-phenylpropanamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-6-chloronicotinamide;
(1R*,2R*)-N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylcyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-(benzyloxy)acetamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-naphthamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-(trifluoromethyl)benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethoxy)benzamide;
methyl 6-({4-[4-amino-2-(ethoxymethyl)-7methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)-6-oxohexanoate;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1,3-benzodioxole-5-carboxamide;
methyl 6-({4-[4-amino-2-(ethoxymethyl)-7methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)carbonyl]benzoate;
and
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}adamantane-1-carboxamide;
or a pharmaceutically acceptable salt thereof.

21 more elements

Dependencies are inferred from the claim text.

Facts

Application

10/357,995Filed 4 Feb 2003 · continuation

Priority

8 Dec 2000

Published

US 2003/0162806 A128 Aug 2003

Granted

13 Apr 2004

Term ends

Not estimatedThe source records don’t support an estimate.

Classification2 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D
Heterocyclic compounds

Family

Application60/254,228Us provisional application · filed 8 Dec 2000

Application10/016,073Parent of this continuation-in-part · filed 6 Dec 2001

Application10/165,229Parent of this continuation · filed 7 Jun 2002

US 2003/0162806 A1Pre-grant publication · published 28 Aug 2003

US 6,545,016 B1Parent of this continuation

Application10/165,229Parent of this continuation-in-part

US 2002/0107262 A1Published application

US 6,720,333 B2This patent

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

Abstract

Claims45

Dependent claims

A compound of the formula (I):

wherein
X is ethylene, propylene, or butylene;
Y is —CO—;
Z is a bond;
R1 is aryl, heteroaryl, C1-10 alkyl, or C2-10 alkenyl, each of which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of:
-alkyl;
-aryl;
-substituted aryl;
-heteroaryl;
—O-alkyl;
—O-(alkyl)0-1 aryl;
—CO—O-alkyl;
-halogen;
-haloalkyl;
-haloalkoxy;
and
—CN;
R2 is selected from the group consisting of:
-hydrogen;
—C1-10 alkyl;
and
—C1-10 alkyl-O—C1-10 alkyl;
R3 and R4 are independently selected from the group consisting of hydrogen, and methyl;
R5 is H or C1-10 alkyl, or R5 can join with X to form a ring;
or a pharmaceutically acceptable salt thereof.

22 more elements

A compound selected from:

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}pentanamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclohexanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-fluorobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-thien-2-ylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-phenylpropanamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-6-chloronicotinamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}nicotinamide;
(1R*,2R*)-N-{3-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl)-2-phenylcyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-(benzyloxy)acetamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-naphthamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-(trifluoromethyl)benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzamide;
and
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethoxy)benzamide;
or a pharmaceutically acceptable salt thereof.

17 more elements

A compound selected from:

1-{2-[1-(cyclopropylcarbonyl)piperidin-4-yl]ethyl}-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-pentanoylpiperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine;
1-[2-(1-benzoylpiperidin-4-yl)ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
1-{2-[1-(cyclohexylcarbonyl)piperidin-4-yl]ethyl}-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(phenylacetyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-1-{2-[1-(4-fluorobenzoyl)piperidin-4-yl)ethyl}-6,7-dimethyl-1H-imidazo[4,5-c)pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(thien-2-ylacetyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-1-{2-[1-(3-cyanobenzoyl)piperidin-4-yl]ethyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(3-phenylpropanoyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
1-(2-{1-[(6-chloropyridin-3-yl)carbonyl]piperidin-4-yl}ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-{[(1R*,2R*)-2-phenylcyclopropyl]carbonyl}piperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine;
1-(2-{1-[(benzyloxy)acety]piperidin-4-yl}ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(2-naphthoyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-(2-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}ethyl)-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-(2-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}ethyl)-1H-imidazo[4,5-c]pyridin-4-amine;
and
2-(ethoxymethyl)-6,7-dimethyl-1-(2-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}ethyl)-1H-imidazo[4,5-c]pyridin-4-amine;
or a pharmaceutically acceptable salt thereof.

15 more elements

A compound selected from:

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]cyclopropanecarboxamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]pentanamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]cyclohexanecarboxamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-phenylacetamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-fluorobenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-thien-2-ylacetamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-cyanobenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-cyanobenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-phenylpropanamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-methoxybenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-methoxybenzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-6-chloronicotinamide;
(1R*,2R*)-N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-phenylcyclopropanecarboxamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-naphthamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-(trifluoromethyl)benzamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-(trifluoromethyl)benzamide;
and
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-(trifluoromethoxy)benzamide;
or a pharmaceutically acceptable salt thereof.

16 more elements

A compound selected from:

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}cyclopropanecarboxamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}pentanamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}benzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}cyclohexanecarboxamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-phenylacetamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-fluorobenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-thien-2-ylacetamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-cyanobenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-cyanobenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-phenylpropanamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-methoxybenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-methoxybenzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-6-chloronicotinamide;
(1R*,2R*)-N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-phenylcyclopropanecarboxamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-(benzyloxy)acetamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-naphthamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-(trifluoromethyl)benzamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(trifluoromethyl)benzamide;
and
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(trifluoromethoxy)benzamide;
or a pharmaceutically acceptable salt thereof.

18 more elements

A compound selected from:

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]cyclopropanecarboxamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]pentanamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]benzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]cyclohexanecarboxamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylacetamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-fluorobenzamide,
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-thien-2-ylacetamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-cyanobenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyanobenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-phenylpropanamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-methoxybenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-methoxybenzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-6-chloronicotinamide;
(1R*,2R*)-N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylcyclopropanecarboxamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-(benzyloxy)acetamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-naphthamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-(trifluoromethyl)benzamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethyl)benzamide
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethoxy)benzamide;
2-{[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}-2-oxoethyl acetate;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1,3-benzodioxole-5-carboxamide;
methyl 4-({[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}carbonyl)benzoate;
and
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]adamantane-1-carboxamide;
or a pharmaceutically acceptable salt thereof.

22 more elements

A compound selected from:

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}cyclohexanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-fluorobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-thien-2-ylacetamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-cyanobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-cyanobenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-phenylpropanamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-6-chloronicotinamide;
(1R*,2R*)-N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylcyclopropanecarboxamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-(benzyloxy)acetamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-naphthamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-(trifluoromethyl)benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethoxy)benzamide;
methyl 6-({4-[4-amino-2-(ethoxymethyl)-7methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)-6-oxohexanoate;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1,3-benzodioxole-5-carboxamide;
methyl 6-({4-[4-amino-2-(ethoxymethyl)-7methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)carbonyl]benzoate;
and
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}adamantane-1-carboxamide;
or a pharmaceutically acceptable salt thereof.

21 more elements

Dependencies are inferred from the claim text.

Amide substituted imidazopyridines

Life of this patent

Abstract

Claims45

Amide substituted imidazopyridines

Life of this patent

Abstract

Claims45