Loading patent…

Back to results

US 6,696,465 B2Granted

Sulfonamido substituted imidazopyridines

Assignee3M Innovative Properties Company

InventorsJoseph F. Dellaria, Chad A. Haraldson, Philip D. Heppner, Kyle J. Lindstrom, Byron A. Merrill

Life of this patent

Estimating the term…

Download PDF Find prior artPrior art Similar

Abstract Drawings Claims Description

Abstract

Imidazopyridine compounds that contain sulfonamide 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.

Claims40

Dependent claims

Claim 1A compound of the formula (I) · 147 words4 dependent Claim 2A compound selected from the group · 32 words4 dependent Claim 3A compound selected from the group · 32 words4 dependent Claim 4A compound selected from the group · 26 words4 dependent Claim 5A compound selected from the group · 27 words4 dependent Claim 6A compound selected from the group · 33 words4 dependent Claim 7A compound selected from the group · 41 words4 dependent Claim 8A compound selected from the group · 38 words4 dependent

A compound of the formula (I):

wherein
X is ethylene, propylene, or butylene;
Y is —SO2—;
Z is a bond or —NR6—;
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;
—O-alkyl;
—COOH;
—S(O)0-2-alkyl;
-(alkyl)0-1—NR6—CO-aryl;
-halogen;
-haloalkyl;
-haloalkoxy;
—NO2;
—CN;
and in the case of alkyl and alkenyl, oxo;
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 when R1 is C1-10 alkyl, R5 and R1 can join to form a ring;
each R6 is independently H or C1-10 alkyl;
or a pharmaceutically acceptable salt thereof.

25 more elements

A compound selected from the group consisting of:

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]ethanesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]propane-2-sulfonamide;
N′-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N,N-dimethylsulfamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]butane-1-sulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzenesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]thiophene-2-sulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-1-phenylmethanesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-fluorobenzenesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-cyanobenzenesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-methoxybenzenesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]naphthalene-1-sulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]quinoline-8-sulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-(trifluoromethyl)benzenesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-1,1′-biphenyl-4-sulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-(methylsulfonyl)benzenesulfonamide;
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-(trifluoromethoxy)benzenesulfonamide;
and
N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzenesulfonamide;
or a pharmaceutically acceptable salt thereof.

16 more elements

A compound selected from the group consisting of:

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}ethanesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}propane-2-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}butane-1-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}thiophene-2-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1-phenylmethanesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-fluorobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-cyanobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-cyanobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2,4-difluorobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}naphthalene-1-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}quinoline-8-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1-[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(methylsulfonyl)benzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]buty1}-4-(trifluoromethoxy)benzenesulfonamide;
and
N-[4-(4-amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzenesulfonamide;
or a pharmaceutically acceptable salt thereof.

16 more elements

A compound selected from the group consisting of:

2-(ethoxymethyl)-1-{2-[1-(ethylsulfonyl)piperidin-4-yl]ethyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-1-{2-[1-(isopropylsulfonyl)piperidin-4-yl]ethyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
4-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N,N-dimethylpiperidine-1-sulfonamide;
1-{2-[1-(butylsulfonyl)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-naphthylsulfonyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(quinolin-8-ylsulfonyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine;
1-[4-(1,1-dioxidoisothiazolidin-2-yl)butyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine;
1-{2-[1-(1,1′-biphenyl-4-ylsulfonyl)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-{[4-(methylsulfonyl)phenyl]sulfonyl}piperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine;
and
1-(2-{1-[4-(4-dimethylaminophenylazo)benzenesulfonyl]piperidin-4-yl}ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;
or a pharmaceutically acceptable salt thereof.

10 more elements

A compound selected from the group consisting of:

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]ethanesulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]propane-2-sulfonamide;
N′-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-N,N-dimethylsulfamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]butane-1-sulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]thiophene-2-sulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-fluorobenzenesulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-cyanobenzenesulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]naphthalene-1-sulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]naphthalene-2-sulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-C-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamide;
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-1,1′-biphenyl-4-sulfonamide;
and
N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-(trifluoromethoxy)benzenesulfonamide;
or a pharmaceutically acceptable salt thereof.

11 more elements

A compound selected from the group consisting of:

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}ethanesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}propane-2-sulfonamide;
N′-[4-(4-amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-N,N-dimethylsulfamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}butane-1-sulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}benzenesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}thiophene-2-sulfonamide;
(E)-N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-phenylethenesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-fluorobenzenesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-cyanobenzenesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-cyanobenzenesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-methoxybenzenesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2,4-difluorobenzenesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}naphthalene-1-sulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}naphthalene-2-sulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(trifluoromethyl)benzenesulfonamide;
N-[3-(4-amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-C-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamide;
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-1,1′-biphenyl-4-sulfonamide;
and
N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(methylsulfonyl)benzenesulfonamide;
or a pharmaceutically acceptable salt thereof.

17 more elements

A compound selected from the group consisting of:

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]ethanesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]propane-2-sulfonamide;
N′-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-N,N-dimethylsulfamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]butane-1-sulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]benzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]thiophene-2-sulfonamide;
(E)-N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylethenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-fluorobenzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-cyanobenzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyanobenzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-methoxybenzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2,4-difluorobenzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]naphthalene-1-sulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]naphthalene-2-sulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethyl)benzenesulfonamide;
N-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-C-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1,1′-biphenyl-4-sulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(methylsulfonyl)benzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethoxy)benzenesulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1-methyl-1H-imidazole-4-sulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3,5-dimethylisoxazole-4-sulfonamide;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-5-chlorothiophene-2-sulfonamide;
4-({[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}sulfonyl)benzoic acid;
N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1-(2-nitrophenyl)methanesulfonamide;
and
N-{[5-({[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}sulfonyl)thien-2-yl]methyl}benzamide;
or a pharmaceutically acceptable salt thereof.

24 more elements

A compound selected from the group consisting of:

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}ethanesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}propane-2-sulfonamide;
N′-[4-(4-amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N,N-dimethylsulfamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}butane-1-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}benzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}thiophene-2-sulfonamide;
(E)-N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylethenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-fluorobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-cyanobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-cyanobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2,4-difluorobenzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}naphthalene-1-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}naphthalene-2-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzenesulfonamide;
N-[4-(4-amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-C-(7,7-dimethyl-2-oxobicyclo[2.21]hept-1-yl)methanesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-biphenyl-4-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(methylsulfonyl)benzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-(trifluoromethoxy)benzenesulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1-methyl-1H-imidazole-4-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3,5-dimethylisoxazole-4-sulfonamide;
N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-5-chlorothiophene-2-sulfonamide;
and
N-({5-[({4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)sulfonyl]thien-2-yl}methyl)benzamide;
or a pharmaceutically acceptable salt thereof.

22 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/322,262Filed 17 Dec 2002 · continuation
Priority: 8 Dec 2000
Published: US 2004/0019076 A129 Jan 2004
Granted: 24 Feb 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
Application10/165,002Parent of this continuation · filed 7 Jun 2002
US 2004/0019076 A1Pre-grant publication · published 29 Jan 2004
US 6,525,064 B1Parent of this continuation
Application10/165,002Parent of this continuation-in-part
US 2002/0107262 A1Published application
US 6,696,465 B2This patent

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

Timeline

Citations

Open elsewhere

USPTO full text and PDF
Patent Center file history
USPTO assignment records
Espacenet
Google Patents