Fused Tricyclic imidazole derivatives as modulators of TNF activity

1. A compound represented by formula (I), or a pharmaceutically acceptable salt thereof,

wherein

n represents an integer equal to 1 or 2;

Y represents C 3-7 cycloalkyl, aryl, C 3-7 heterocycloalkyl or heteroaryl, any of which groups may be optionally substituted by one, two or three substituents independently selected from halogen, cyano, nitro, C 1-6 alkyl, trifluoromethyl, hydroxy, C 1-6 alkoxy, difluoromethoxy, trifluoromethoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, (C 1-6 )alkylsulfonyloxy, amino, C 1-6 alkyl-amino, di(C 1-6 )alkylamino, arylamino, C 2-6 alkylcarbonylamino, C 1-6 alkylsulfonylamino, formyl, C 2-6 alkylcarbonyl, C 3-6 cycloalkylcarbonyl, C 3-6 heterocycloalkylcarbonyl, carboxy, C 2-6 alkoxycarbonyl, aminocarbonyl, C 1-6 alkylaminocarbonyl, di(C 1-6 )alkyl-aminocarbonyl, aminosulfonyl, C 1-6 alkylaminosulfonyl and di(C 1-6 )alkylaminosulfonyl;

X and Z independently represent a heteroatom; carbonyl, —S(O)—, —S(O) 2 —, —S(O)(N—R d ), —NC(O)R d , —N(CO)—OR d , —NS(O) 2 R d or —N(R d ); or X and Z independently represent a straight or branched C 1-4 alkylene chain optionally substituted by one or more substituents selected from halogen, hydroxy, oxo, C 1-6 alkoxy, aryl, —C(O)R d , —CO 2 R d , —CONR b R c —S(O)(N—R d )R a , or —SO 2 NR b R c ;

R 1 represents cyano or R 1 represents C 1-6 alkyl, C 2-6 alkynyl, aryl, C 3-7 heterocycloalkyl, C 3-7 heterocycloalkenyl, heteroaryl, (C 3-7 )heterocycloalkyl(C 1-6 )alkyl-aryl-, heteroaryl(C 3-7 )heterocycloalkyl-, (C 3-7 )cycloalkyl-heteroaryl-, (C 3-7 )cycloalkyl-(C 1-6 )alkyl-heteroaryl-, (C 4-7 )cycloalkenyl-heteroaryl-, (C 4-9 )bicycloalkyl-heteroaryl-, (C 3-7 )heterocycloalkyl-heteroaryl-, (C 3-7 )heterocycloalkyl(C 1-6 )alkyl-heteroaryl-, (C 3-7 )heterocycloalkenyl-heteroaryl-, (C 4-9 )heterobicycloalkyl-heteroaryl-, heteroaryl-aryl, or (C 4-9 )spiroheterocycloalkyl-heteroaryl-, any of which groups may be optionally substituted by one, two or three substituents independently selected from halogen, halo(C 1-6 )alkyl, cyano, cyano(C 1-6 )alkyl, nitro(C 1-6 )alkyl, C 1-6 alkyl, trifluoromethyl, trifluoroethyl, C 2-6 alkenyl, hydroxy, hydroxy(C 1-6 )alkyl, C 1-6 alkoxy, trifluoroethoxy, carboxy(C 3-7 )cycloalkyloxy, C 1-6 alkylthio, C 1-6 alkylsulphonyl, aryl-sulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, oxo, amino, amino-(C 1-6 )alkyl, C 1-6 alkylamino, di(C 1-6 )alkylamino, (C 1-6 )alkoxy(C 1-6 )alkylamino, N—[(C 1-6 )alkyl]-N-[hydroxy(C 1-6 )alkyl]amino, (C 2-6 )alkylcarbonylamino(C 1-6 )alkyl, C 1-6 alkylsulphonylamino, N—[(C 1-6 )alkyl]-N—[(C 1-6 )alkylsulphonyl]amino, bis[(C 1-6 )alkyl-sulphonyl]amino, N—[(C 1-6 )alkyl]-N-[carboxy(C 1-6 )alkyl]amino, carboxy(C 3-7 )cycloalkyl-amino, carboxy(C 3-7 )cycloalkyl(C 1-6 )alkylamino, formyl, C 2-6 alkylcarbonyl, (C 2-6 )alkyl-carbonyloxy(C 1-6 )alkyl, carboxy, carboxy(C 1-6 )alkyl, C 2-6 alkoxycarbonyl, C 2-6 alkoxycarbonyl(C 1-6 )alkyl, morpholinyl(C 1-6 )alkoxycarbonyl, C 2-6 alkoxycarbonyl-methylidenyl, aminocarbonyl, di(C 1-6 )alkylaminocarbonyl, aminosulphonyl, (C 1-6 )alkylsulphoximinyl and [(C 1-6 )alkyl][N—(C 1-6 )alkyl]sulphoximinyl;

R 2 represents hydrogen, halogen, cyano, nitro, hydroxy, trifluoromethyl, trifluoromethoxy or —OR a ; or R 2 represents C 1-6 alkyl optionally substituted by C 2-6 alkoxycarbonyl;

R 3 and R 4 independently represents hydrogen, halogen, cyano, nitro, hydroxy, trifluoromethyl, trifluoromethoxy or —OR a ; or C 1-6 alkyl;

R 5a and R 5b independently represent hydrogen, hydroxy, halogen, trifluoromethyl, cyano; —NR b R c , —S(O) 2 R a , —OR a , or —O(CO)—R d —; or R 5a and R 5b independently represent C 1-6 alkyl which group may be optionally substituted by one, two or three substituents independently selected from halogen, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkylcarbonyl, C 2-6 alkyloxycarbonyl, (hydroxy)C 1-6 alkyl, (C 3-7 )cycloalkyl, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, di(C 1-6 )alkylaminocarbonyl, oxo, and carboxy; or R 5a and R 5b when taken together with the carbon to which they are attached represent a carbonyl, thiocarbonyl or —C═N—OH; and

R 6 represents hydrogen, hydroxy, halogen, or trifluoromethyl; or

R 6 and Y together with the carbon to which they are attached form a C 3-7 cycloalkyl or C 3-7 heterocycloalkyl, optionally substituted by halogen; and

R a represents C 1-6 alkylaryl(C 1-6 )alkyl, or heteroaryl(C 1-6 )alkyl, any of which groups may be optionally substituted by C 1-6 alkoxy or oxo;

R b represents hydrogen or R b represents C 1-6 alkyl, aryl(C 1-6 )alkyl, C 3-7 heterocycloalkyl, and C 3-7 heterocycloalkyl(C 1-6 )alkyl, any of which groups may be optionally substituted by one or more substituents selected from C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulphinyl, C 1-6 alkylsulphonyl, hydroxy, cyano, C 2-6 alkoxycarbonyl, di-(C 1-6 )alkylamino and C 2-6 alkoxycarbonylamino;

R c represents hydrogen or R c represents C 1-6 alkyl, C 3-7 cycloalkyl, or C 3-7 heterocycloalkyl, any of which groups may be optionally substituted by C 2-6 alkylcarbonyl or C 2-6 alkoxycarbonyl; and

R d represents hydrogen or R d represents C 1-6 alkyl, aryl, or heteroaryl, either of which groups may be optionally substituted by one or more substituents selected from halogen, C 1-6 alkyl, C 1-6 alkoxy, oxo, C 2-6 alkylcarbonyloxy and di(C 1-6 )alkylamino.

2. The compound as claimed in claim 1 , represented by formula (IIA), or a pharmaceutically acceptable salt thereof,

wherein

R 2 represents hydrogen, halogen, trifluoromethyl, or cyano; or R 2 represents an optionally substituted C 1-6 alkyl optionally substituted by C 2-6 alkoxycarbonyl;

X is oxygen or —NR d ;

Z represents a straight or branched C 1-4 alkylene chain optionally substituted by one or more substituents selected from halogen, hydroxy, oxo, C 1-6 alkoxy, aryl, —C(O)R d , —CO 2 R d , —CONR b R c —S(O)(N—R d )R a , or —SO 2 NR b R c ;

R 5a represents hydrogen, hydroxy, halogen, trifluoromethyl, cyano; —NR b R c , —S(O) 2 R a , —OR a , or —O(CO)—R d —; or R 5a represents C 1-6 alkyl, which group may be optionally substituted by one, two or three substituents independently selected from halogen, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkylcarbonyl, C 2-6 alkyloxycarbonyl, (hydroxy)C 1-6 alkyl, (C 3-7 )cycloalkyl, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, di(C 1-6 )alkylaminocarbonyl, oxo, and carboxy; and

R 5b represents hydrogen, hydroxy, halogen, cyano, or trifluoromethyl; or R 5b represents C 1-6 alkyl, any of which groups may be optionally substituted by one, two or three substituents independently selected from halogen, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkylcarbonyl, C 2-6 alkyloxycarbonyl, (hydroxy)C 1-6 alkyl, (C 3-7 )cycloalkyl, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, di(C 1-6 )alkylaminocarbonyl, oxo, and carboxy; or R 5a and R 5b when taken together with the carbon to which they are attached represent a carbonyl, thiocarbonyl, or —C═N—OH.

3. The compound as claimed in claim 2 , represented by formula (IIB) or formula (IIN), or a pharmaceutically acceptable salt thereof,

wherein

V represents C—R 12 or N;

R 9 represents hydrogen, halogen, halo(C 1-6 )alkyl, cyano, cyano(C 1-6 )alkyl, nitro(C 1-6 )alkyl, C 1-6 alkyl, trifluoromethyl, trifluoroethyl, C 2-6 alkenyl, hydroxy, hydroxy(C 1-6 )alkyl, C 1-6 alkoxy, trifluoroethoxy, carboxy(C 3-7 )cycloalkyloxy, C 1-6 alkylthio, C 1-6 alkylsulphonyl, aryl-sulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, oxo, amino, amino-(C 1-6 )alkyl, C 1-6 alkylamino, di(C 1-6 )alkylamino, (C 1-6 )alkoxy(C 1-6 )alkylamino, N—[(C 1-6 )alkyl]-N-[hydroxy(C 1-6 )alkyl]amino, (C 2-6 )alkylcarbonylamino(C 1-6 )alkyl, C 1-6 alkylsulphonylamino, N—[(C 1-6 )alkyl]-N—[(C 1-6 )alkylsulphonyl]amino, bis[(C 1-6 )alkyl-sulphonyl]amino, N—[(C 1-6 )alkyl]-N-[carboxy(C 1-6 )alkyl]amino, carboxy(C 3-7 )cycloalkyl-amino, carboxy(C 3-7 )cycloalkyl(C 1-6 )alkylamino, formyl, C 2-6 alkylcarbonyl, (C 2-6 )alkyl-carbonyloxy(C 1-6 )alkyl, carboxy, carboxy(C 1-6 )alkyl, C 2-6 alkoxycarbonyl, C 2-6 alkoxycarbonyl(C 1-6 )alkyl, morpholinyl(C 1-6 )alkoxycarbonyl, C 2-6 alkoxycarbonyl-methylidenyl, aminocarbonyl, di(C 1-6 )alkylaminocarbonyl, aminosulphonyl, (C 1-6 )alkylsulphoximinyl or [(C 1-6 )alkyl][N—(C 1-6 )alkyl]sulphoximinyl; or R 9 represents (C 3-7 )cycloalkyl, (C 3-7 )heterocycloalkyl, or heteroaryl, any of which groups may be optionally substituted by one or more substituents selected from cyano, trifluoromethyl, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphoximinyl, C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, oxo and carboxy;

R 10 and R 11 independently represents hydrogen, halogen, cyano, trifluoromethyl, hydroxy; —NR b R c , —OR a , C 1-6 alkyl, or C 1-6 alkylsulphonyl; and

R 12 represents hydrogen, halogen or C 1-6 alkyl.

4. The compound as claimed in claim 1 represented by formula (IIP), (IIQ), (IIS), or (IIT), or a pharmaceutically acceptable salt thereof,

wherein

R 17 independently represents hydrogen, C 1-6 alkyl, C 1-6 alkylsulphonyl, C 1-6 alkylsulphonylalkyl, trifluoromethyl or C 2-6 alkoxycarbonyl;

X is oxygen or —NR d ;

Z represents a straight or branched C 1-4 alkylene chain optionally substituted by one or more substituents selected from halogen, hydroxy, oxo, C 1-6 alkoxy, aryl, —C(O)R d , —CO 2 R d , —CONR b R c —S(O)(N—R d )R a , or —SO 2 NR b R c ;

R 5a represents hydrogen, hydroxy, halogen, trifluoromethyl, cyano; —NR b R c , —S(O) 2 R a , —OR a , or —O(CO)—R d —; or R 5a represents C 1-6 alkyl, which group may be optionally substituted by one, two or three substituents independently selected from halogen, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkylcarbonyl, C 2-6 alkyloxycarbonyl, (hydroxy)C 1-6 alkyl, (C 3-7 )cycloalkyl, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, di(C 1-6 )alkylaminocarbonyl, oxo, and carboxy;

R 5b represents hydrogen, hydroxy, halogen, cyano, or trifluoromethyl; or R 5b represents C 1-6 alkyl, any of which groups may be optionally substituted by one, two or three substituents independently selected from halogen, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkoxy, C 2-6 alkylcarbonyl, C 2-6 alkyloxycarbonyl, (hydroxy)C 1-6 alkyl, (C 3-7 )cycloalkyl, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, di(C 1-6 )alkylaminocarbonyl, oxo, and carboxy; or R 5a and R 5b when taken together with the carbon to which they are attached represent a carbonyl, thiocarbonyl, or —C═N—OH;

R 2 represents hydrogen, halogen, trifluoromethyl, or cyano; or R 2 represents an optionally substituted C 1-6 alkyl optionally substituted by C 2-6 alkoxycarbonyl;

T represents —CH 2 — or —CH 2 CH 2 ;

U represents C(O) or S(O) 2 ;

W represents O, N(R 14 ), or C(R 15 )(R 16 );

R 14 represents hydrogen, C 1-6 alkyl, or C 2-6 alkylcarbonyl;

R 15 represents hydrogen, halogen, cyano, hydroxy, hydroxy(C 1-6 )alkyl, C 1-6 alkylsulphonyl, formyl, carboxy, carboxy(C 1-6 )alkyl, C 2-6 alkoxycarbonyl, C 2-6 alkoxycarbonyl(C 1-6 )alkyl, aminosulphonyl, (C 1-6 )alkylsulphoximinyl, [(C 1-6 )alkyl][N—(C 1-6 )alkyl]sulphoximinyl, (C 1-6 )alkylsulphonylaminocarbonyl, (C 2-6 )alkylcarbonylamino-sulphonyl, (C 1-6 )alkoxyaminocarbonyl, tetrazolyl or hydroxyoxadiazolyl;

R 16 represents hydrogen, halogen or C 1-6 alkyl.

5. The compound as claimed in claim 3 wherein, R 9 represents (C 1-6 )alkyl, halo(C 1-6 )alkyl, (hydroxy)C 1-6 alkyl, C 1-6 alkoxy, arylsulphonyl, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, C 2-6 alkylcarbonylamino(C 1-6 )alkyl, (C 1-6 )alkylsulphoximinyl, carboxy, oxo, or C 2-6 alkyloxycarbonyl; or R 9 represents (C 3-7 )cycloalkyl, (C 3-7 )heterocycloalkyl, or heteroaryl, any of which groups may be optionally substituted by one or more substituents selected from cyano, trifluoromethyl, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphoximinyl, C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, oxo and carboxy.

6. The compound as claimed in claim 1 represented by formula (IIW), or a pharmaceutically acceptable salt thereof,

7. The compound as claimed in claim 1 wherein X represents an oxygen atom.

8. The compound as claimed in claim 1 wherein Z represents a methylene group.

9. The compound as claimed in claim 1 wherein Y represents an optionally substituted aryl.

10. The compound as claimed in claim 1 wherein Y represents 2-difluoromethoxy-phenyl.

11. The compound as claimed in claim 1 wherein R 2 represents hydrogen or halogen.

12. The compound according to claim 1 wherein R 5a represents hydroxyl or hydrogen.

13. The compound as claimed in claim 1 , wherein R 5b represents hydrogen or methyl.

14. A compound that is

1-[2-(difluoromethoxy)phenyl]-8-(6-methoxypyridin-3-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[2-(difluoromethoxy)phenyl]-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[2-(difluoromethoxy)phenyl]-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-1,2,3,4-tetrahydroimidazo[1,2-a:5,4-c′]dipyridine;

1-[2-(difluoromethoxy)phenyl]-8-(6-methoxypyridin-3-yl)-1,2,3,4-tetrahydroimidazo[1,2-a:5,4-c′]dipyridine;

8-(6-methoxypyridin-3-yl)-1-phenyl-1,2,3,4-tetrahydroimidazo[1,2-a:5,4-c′]dipyridine;

(1S)-1-[2-(difluoromethoxy)phenyl]-8-[4-(methylsulfonyl)phenyl]-1,2,3,4-tetrahydroimidazo[1,2-a:5,4-c′]dipyridine;

(1R)-1-[2-(difluoromethoxy)phenyl]-8-[4-(methylsulfonyl)phenyl]-1,2,3,4-tetrahydroimidazo[1,2-a:5,4-c′]dipyridine;

4-{5-[(R)-4-(2-difluoromethoxy-phenyl)-7-fluoro-1,4-dihydro-2H-3-oxa-4b,9-diaza-fluoren-6-yl]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester;

(1R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[6-(piperazin-1-yl)pyridin-3-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

4-{5-[(S)-4-(2-difluoromethoxy-phenyl)-7-fluoro-1,4-dihydro-2H-3-oxa-4b,9-diaza-fluoren-6-yl]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester;

(1S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[6-(piperazin-1-yl)pyridin-3-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[4-(methylsulfonyl)phenyl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-8-(6-cyclopropylpyridin-3-yl)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[6-(methylsulfonyl)pyridin-3-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-8-(1-cyclopropyl-1H-pyrazol-4-yl)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[1-(phenylsulfonyl)-1H-pyrazol-4-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

N-(4-{(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}benzyl)acetamide;

tert-butyl 5-{(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}-1,3-dihydro-2H-isoindole-2-carboxylate;

4-{(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}benzonitrile;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-(1H-pyrazol-4-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-{4-[(methylsulfonyl)methyl]phenyl}-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(5-{(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyridin-2-yl)methanol;

difluoromethyl 2-{8-[1-(phenylsulfonyl)-1H-pyrazol-4-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-1-yl}phenyl ether;

methyl 1-(5-{1-[2-(difluoromethoxy)phenyl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyrimidin-2-yl)piperidine-4-carboxylate;

1-(5-{(4R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acid ethyl ester;

1-(5-{(4S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acid ethyl ester;

8-(6-methoxypyridin-3-yl)-1-phenyl-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(4S or R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[3-(methylsulfonyl)phenyl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(4S or R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[2-(methylsulfonyl)pyridin-4-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(4S)-8-fluoro-7-[4-(methylsulfonyl)phenyl]-4-phenyl-3,4-dihydro-1H-pyrano[3′,4′:4,5]imidazo[1,2-a]pyridine;

(4R)-8-fluoro-7-[4-(methylsulfonyl)phenyl]-4-phenyl-3,4-dihydro-1H-pyrano[3′,4′:4,5]imidazo[1,2-a]pyridine;

(1S,4S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[6-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-4-ol;

(1S,4R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[6-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-4-ol;

N-(4-{(1S or R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}benzyl)-N-methylacetamide;

(1S or R)-8-(2-cyclopropylpyrimidin-5-yl)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[4-(5-methyl-1H-1,2,4-triazol-3-yl)phenyl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[1-(methylsulfonyl)-1H-pyrazol-4-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-8-(2,3-dihydro-1H-isoindol-5-yl)-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[2-(methylsulfonyl)-2,3-dihydro-1H-isoindol-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-8-[1-(1, 1-dioxidotetrahydrothiophen-3-yl)-1H-pyrazol-4-yl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

(1R or S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-{6-[(methylsulfonyl)methyl]pyridin-3-yl}-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[2-(difluoromethoxy)phenyl]-8-(4-methoxypiperidin-1-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[2-(difluoromethoxy)phenyl]-8-[4-(methylsulfonyl)piperazin-1-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[2-(difluoromethoxy)phenyl]-8-(3-methoxyazetidin-1-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[2-(difluoromethoxy)phenyl]-8-[3-methoxypyrrolidin-1-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[2-(difluoromethoxy)phenyl]-8-(1H-pyrazol-4-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(5-{(1-[2-(difluoromethoxy)phenyl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyrimidin-2-yl)piperidine-4-carboxylic acid;

1-(5-{(1R)-1-[2-(difluoromethoxy)phenyl]7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acid;

1-(5-{(1S)-1-[2-(difluoromethoxy)phenyl]7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acid;

1-(5-chloro-2-methylthiazol-4-yl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(5-chloro-2-(difluoromethoxy)phenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(5-chloro-2-(trifluoromethoxy)phenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2-chlorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(3-chlorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(3-(difluoromethoxy)phenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2, 5-dimethylphenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2, 5-dichlorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2-chloro-6-(difluoromethoxy)phenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

7-fluoro-8-(2-morpholinopyrimidin-5-yl)-1-(2-(trifluoromethoxy)phenyl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2-chloro-6-(trifluoromethoxy)phenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

7-fluoro-8-(2-morpholinopyrimidin-5-yl)-1-(2-(trifluoromethyl)phenyl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2, 5-bis(difluoromethoxy)phenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2-(difluoromethoxy)-5-fluorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2-(difluoromethoxy)-3,5-difluorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2-(difluoromethoxy)-3-fluorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2-chloro-5-fluorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(5-chloro-2-fluorophenyl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(4,6-dimethoxypyrimidin-5-yl)-7-fluoro-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

7-fluoro-1-(2-methyl-4-(trifluoromethyl)thiazol-5-yl)-8-(2-morpholinopyrimidin-5-yl)-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-[4-(difluoromethoxy)phenyl]-7-fluoro-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(4-chlorophenyl)-7-fluoro-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

3-{7-fluoro-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-1-yl}benzonitrile;

7-fluoro-1-(4-methyl-1,3-thiazol-5-yl)-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(2,4-dimethyl-1,3-thiazol-5-yl)-7-fluoro-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

4-{7-fluoro-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-1-yl}benzonitrile;

2-{7-fluoro-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-1-yl}benzonitrile;

7-fluoro-1-(5-methoxypyrazin-2-yl)-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

7-fluoro-1-[4-(methyl sulfonyl)phenyl]-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

6-chloro-7′-fluoro-8′-[2-(morpholin-4-yl)pyrimidin-5-yl]-2,3,3′,4′-tetrahydrospiro[indene-1,1′-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

1-(4-chloro-1,3-thiazol-5-yl)-7-fluoro-8-[2-(morpholin-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine;

2-(6-methoxypyridin-3-yl)-10-phenyl-7,8,9,10-tetrahydro-6H-cyclohepta[4,5]imidazo[1,2-a]pyridin-10-ol;

(1R or S,4S or R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[4-(methylsulfonyl)phenyl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-4-ol;

2-(4-{(1R,4S)-1-[5-chloro-2-(difluoromethoxy)phenyl]-7-fluoro-4-hydroxy-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}phenyl)-2-methylpropanenitrile;

2-(4-{(1S,4S)-1-[5-chloro-2-(difluoromethoxy)phenyl]-7-fluoro-4-hydroxy-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}phenyl)-2-methylpropanenitrile;

(1R,4S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[2-(tetrahydro-2H-pyran-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-4-ol;

(1S,4S)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[2-(tetrahydro-2H-pyran-4-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-4-ol;

2-(5-{(1R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridin-8-yl}pyrimidin-2-yl)propan-2-ol;

(1R)-1-[2-(difluoromethoxy)phenyl]-7-fluoro-8-[2-(2-fluoropropan-2-yl)pyrimidin-5-yl]-3,4-dihydro-1H-pyrano[4′,3′:4,5]imidazo[1,2-a]pyridine; or

(4R or S)-4-[2-(difluoromethoxy)phenyl]-7-[6-(methylsulfonyl)pyridin-3-yl]-3,4-dihydroimidazo[1,2-a:4,5-c′]dipyridin-1(2H)-one and (4S or R)-4-[2-(difluoromethoxy)phenyl]-7-[6-(methylsulfonyl)pyridin-3-yl]-3,4-dihydroimidazo[1,2-a:4,5-c′]dipyridin-1(2H)-one.

15. A pharmaceutical composition comprising a compound of formula (I) as defined in claim 1 or an N-oxide thereof, or a pharmaceutically acceptable salt thereof, in association with a pharmaceutically acceptable carrier.

16. A method of treating rheumatoid arthritis, psoriasis, or inflammatory bowel disease, which method comprises administering to a patient in need of such treatment an effective amount of a compound of formula (I), as defined in claim 1 or a pharmaceutically acceptable salt thereof.