3H-imidazo [4, 5-B] pyridine-6-carboxamides as anti-inflammatory agents

1. A compound of formula Ia, Ib, Ic or Id:

in which

R 1 represents C 1-3 alkyl (optionally substituted by one or more fluoro atoms), C 3-6 cycloalkyl, fluoro, chloro, bromo;

R 2 represents hydrogen, C 1-3 alkyl (optionally substituted by one or more fluoro atoms), C 3-6 cycloalkyl, fluoro, chloro, bromo;

R 3 , R 3a and R 4 independently represent hydrogen, fluoro, chloro, bromo, C 1-3 alkyl (optionally substituted by one or more fluoro atoms);

R 6 represents hydrogen; C 1-4 alkyl optionally substituted by one or more fluoro atoms;

R 8 independently represents hydrogen, —O—C 1-6 alkyl, —O-cycloalkyl, —O-heterocycloalkyl [which latter three groups are optionally substituted by one or more substituents selected from fluoro, C 1-3 alkyl, C 3-6 cycloalkyl, —O—C 1-3 alkyl, —N(C 1-3 alkyl) 2 , —NHCO—C 1-3 alkyl, —N(C 1-3 -alkyl)CO—C 1-3 alkyl, in all of which latter groups the alkyl-groups are optionally substituted by one or more fluoro-atoms];

A represents phenyl, pyridyl, 5- or 6-membered heterocycloalkyl, C 3-7 cycloalkyl, C 5-8 linear or branched alkyl (all of which groups are optionally substituted by one or more substituents selected from R 9 ); or

benzyl, pyridylmethylene [which latter two groups are optionally substituted by one or more groups selected from C 1-7 alkyl (optionally substituted by one or more substituents selected from fluoro and —OR x2 ), halo, —CN and/or

—O—C 1-7 alkyl (optionally substituted by one or more fluoro atoms)];

R 9 represents on each occasion when used herein: halo, —N(R y1 )R y2 , —N(R y3 )—C(O)—R y4 , —C(O)N(R y8 )R y9 , —OR y10 , and/or C 1-6 alkyl optionally substituted by one or more substituents selected from fluoro, —N(R y1 )R y2 , —N(R y3 )—C(O)—R y4 , —C(O)N(R y8 )R y9 , and/or —OR y10 ; or

any two R 9 substituents,

when attached to the adjacent atoms of the A group and,

in the case where the R 9 substituents are attached to a non-aromatic A group,

when attached to the same atoms,

may be linked together to form, together with the essential atoms of the A group to which the relevant R 9 substituents are necessarily attached, a further 3- to 8-membered ring, optionally containing a further one or two heteroatoms, and which further ring optionally contains one or two unsaturations and which is optionally substituted by one or more C 1-3 alkyl and/or ═O substituents;

each R y4 , R y6 , R y11 and R y15 :

independently represent C 1-7 alkyl, C 2-7 alkenyl, C 2-7 alkynyl, cycloalkyl, which latter four groups are optionally substituted by one or more fluoro atoms;

each R x2 , R y1 , R y2 , R y3 , R y5 , R y7 , R y8 , R y9 , R y10 , R y12 , R y13 and R y14 :

independently represent hydrogen or C 1-7 alkyl, C 2-7 alkenyl, C 2-7 alkynyl, cycloalkyl, heterocycloalkyl, which latter five groups are optionally substituted one or more substituents selected from fluoro and —OC 1-3 alkyl; or

any two groups, when attached to the same nitrogen atom (i.e. R y1 and R y2 , R y8 and R y9 , and R y13 and R y14 ), may, together with that nitrogen atom to which they are necessarily attached, be linked together to form a 3- to 8-membered ring, optionally containing one or two further heteroatoms and which ring optionally contains one or two unsaturations and is optionally substituted by one or more C 1-3 alkyl and/or ═O substituents;

or a pharmaceutically acceptable salt thereof.

2. A compound of formula Ie, If, Ig or Ih:

in which

R 1 represents chloro, bromo, fluoro, C 1-3 alkyl (which latter alkyl group is optionally substituted by one or more fluoro-atoms);

R 2 represents hydrogen, chloro, bromo, fluoro, C 1-3 alkyl (which latter alkyl group is optionally substituted by one or more fluoro atoms);

R 3 , R 3a and R 4 independently represent hydrogen, chloro, bromo, fluoro, C 1-3 alkyl (which latter alkyl group is optionally substituted by one or more fluoro atoms);

R 6 represents hydrogen; C 1-4 alkyl optionally substituted by one or more fluoro atoms;

R 8 independently represents hydrogen, —O—C 1-4 alkyl [optionally substituted by one or more substituents selected from fluoro, C 1-3 alkyl, —O—C 1-3 alkyl, —N(C 1-3 alkyl) 2 , —NHCO—C 1-3 alkyl, —N(C 1-3 -alkyl)CO—C 1-3 alkyl], —O—C 3-6 cycloalkyl, —O-oxetan-3-yl, —O-tetrahydrofuran-3-yl, —O-pyrrolidin-3-yl (which latter four groups are optionally substituted by one or more substituents selected from fluoro or C 1-3 alkyl);

A represents phenyl, 2-pyridyl, 5- or 6-membered heterocycloalkyl, C 3-7 cycloalkyl, C 5-8 linear or branched alkyl (all of which groups are optionally substituted by one or more substituents selected from R 9 ); or

benzyl, pyridin-2-yl-methylene [which latter two groups are optionally substituted by one or more groups selected from C 1-7 alkyl (optionally substituted by one or more substituents selected from fluoro and —OR x2 ), halo, —CN and/or —O—C 1-7 alkyl (optionally substituted by one or more fluoro atoms)];

R 9 represents halo, —O—C 1-4 alkyl, C 1-4 alkyl, C 3-5 cycloalkyl, (which latter three groups are optionally substituted by one or more fluoro atoms);

or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 1 , selected from the following compounds, or a pharmaceutically acceptable salt thereof:

Compound

Compound

Number

Name

154

2-(2,6-Dichloro-phenylamino)-3H-imidazo[4,5-b]-pyridine-6-carboxylic acid (4-

chloro-3-fluoro-phenyl)-amide;

174

2-(2,6-Dichloro-phenylamino)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic

acid (trans-4-trifluoromethyl-cyclohexyl)-amide;

377

N-(4-Bromophenyl)-2-(2,6-dichlorophenylamino)-5-methoxy-3-methyl-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

379

N-((1r,4r)-4-tert.-Butylcyclohexyl)-2-(2,6-dichlorophenylamino)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

386

2-(2,6-Dichloro-phenylamino)-5-methoxy-3-methyl-N-(4-trifluoromethyl-pyridin-2-

yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide formate;

393

N-(4-tert-Butylcyclohexyl)-2-(2,6-dichlorophenylamino)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

394

2-(2,6-Dichlorophenylamino)-N-((1r,4r)-4-isopropylcyclohexyl)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

400

2-(2,6-Dichlorophenylamino)-N-((1r,4r)-4-isopropylcyclohexyl)-3-methyl-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

401

N-(4-Bromophenyl)-2-(2,6-dichlorophenylamino)-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

403

2-(2,6-Dichlorophenylamino)-3-methyl-N-octyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

411

(R)-2-(2,6-Dichlorophenylamino)-3-methyl-N-(oct-2-yl)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

413

3-Benzyl-2-(2,6-dichlorophenylamino)-N-(4,4-dimethylcyclohexyl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

429

2-(2,6-Dichlorophenylamino)-N-(4,4-dimethylcyclohexyl)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

438

2-(2,6-Dichlorophenylamino)-N-(4-ethylcyclohexyl)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

439

2-(2,6-Dichlorophenylamino)-N-hexyl-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

448

2-(2,6-Dichlorophenylamino)-N-heptyl-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

449

(R)-2-(2,6-Dichlorophenylamino)-N-(hept-2-yl)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

453

2-(2,6-Dichlorophenylamino)-3-methyl-N-((1r,4r)-4-methylcyclohexyl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

454

2-(2,6-Dichlorophenylamino)-N-(3,3-dimethylcyclohexyl)-3-methyl-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

459

2-(2,6-Dichlorophenylamino)-N-((1r,4r)-4-trifluoromethyl-cyclohexyl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

463

N-(4-Bromophenyl)-2-(2,6-dichlorophenylamino)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

466

2-(2-Chloro-6-fluorophenylamino)-N-(4,4-dimethylcyclohexyl)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

468

2-(2,6-Dichlorophenylamino)-3-methyl-N-(2-trifluoromethyl-benzyl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

469

2-(2,6-Dichlorophenylamino)-N-(3,3-dimethylcyclohexyl)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

471

(S)-2-(2,6-Dichlorophenylamino)-3-methyl-N-(oct-2-yl)-3H-imidazo[4,5-b]pyridine-

6-carboxamide;

473

2-(2,6-Dichlorophenylamino)-N-(hept-4-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

480

N-(4-Bromophenyl)-2-(2-chloro-6-fluorophenylamino)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

485

2-(2,6-Dichlorophenylamino)-N-(spiro[2.5]octan-6-yl)-3H-imidazo[4,5-b]pyridine-

6-carboxamide;

486

2-(2-Chloro-6-fluorophenylamino)-3-methyl-N-((1r,4r)-4-methylcyclohexyl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

497

(S)-2-(2,6-Dichlorophenylamino)-N-(hept-2-yl)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

505

2-(2,6-Dichlorophenylamino)-N-(4,4-dimethylcyclohexyl)-3-isopropyl-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

506

2-(2,6-Dichlorophenylamino)-3-methyl-N-(spiro[2.4]heptan-5-yl)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

508

(R)-2-(2,6-Dichlorophenylamino)-N-(hexan-2-yl)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

511

2-(2-Chloro-6-fluorophenylamino)-N-(4,4-dimethylcyclohexyl)-3-isopropyl-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

517

(R)-2-(2,6-Dichlorophenylamino)-N-(hex-2-yl)-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

523

3-(But-2-ynyl)-N-cyclohexyl-2-(2,6-dichlorophenylamino)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

527

(S)-2-(2,6-Dichlorophenylamino)-N-(hex-2-yl)-3-methyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

535

2-(2,6-Dichlorophenylamino)-N-((1r,4r)-4-(difluoromethyl)cyclohexyl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

541

2-(2-Chlorophenylamino)-N-(4,4-dimethylcyclohexyl)-3-isopropyl-3H-imidazo[4,5-

b]pyridine-6-carboxamide hydrochloride;

560

(2-(2,6-Dichlorophenylamino)-N-((1r,4r)-4-(difluoromethyl)cyclohexyl)-3-methyl-

3H-imidazo[4,5-b]pyridine-6-carboxamide;

771

N-(4-Bromophenyl)-2-(2-fluoro-6-trifluoromethylphenylamino)-5-(2,2-difluoro-

ethoxy)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

772

N-(4-Bromo-phenyl)-2-(2-trifluoromethyl-phenylamino)-5-(2,2-difluoroethoxy)-3-

methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

773

N-(4-Bromo-phenyl)-2-(2-fluoro-6-chloro-phenylamino)-5-(2,2-difluoroethoxy)-3-

methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

774

N-(4-Bromo-phenyl)-2-(2-fluoro-6-trifluoromethyl-phenylamino)-5-(2,2-

difluoroethoxy)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

775

N-(4-Bromo-phenyl)-2-(2-trifluoromethyl-phenylamino)-5-(2,2-difluoroethoxy)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

776

N-(4-Bromo-phenyl)-2-(2-fluoro-6-chloro-phenylamino)-5-(2,2-difluoroethoxy)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

777

2-(2-Chloro-6-trifluoromethyl-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

778

2-(2-Chloro-6-trifluoromethyl-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

779

2-(2,3,5-Trichloro-pyridin-4-yl-amino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

780

2-(2-Fluoro-6-trifluoromethyl-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

781

2-(2-Fluoro-6-trifluoromethyl-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

782

2-(2-Trifluoromethyl-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

783

2-(2-Chloro-6-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

784

2-(2-Trifluoromethyl-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

785

2-(2-Chloro-6-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

786

2-(2-Bromo-4-methyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

787

2-(3,6-Dichloro-2-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

788

2-(2-Chloro-4-methyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

789

2-(4-Trifluoromethyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

790

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(tetrahydrofuran-3-yl-oxy)-N-((2-

trifluoromethyl-phenyl)-methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

791

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(tetrahydrofuran-3-yl-oxy)-N-(4-bromo-

phenyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

792

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(tetrahydrofuran-3-yl-oxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoro-pentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

793

2-(2-Chloro-4,6-dimethyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

794

2-(2,4-Dimethyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

795

2-(2-Bromo-4-methyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

796

2-(3,6-Dichloro-2-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

797

2-(2-Chloro-4-methyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

798

2-(2-Trifluoromethyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

799

2-(4-Trifluoromethyl-pyridin-3-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

800

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-methoxy-ethoxy)-N-((2-trifluoromethyl-

phenyl)-methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

801

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-methoxy-ethoxy)-N-(4-bromo-phenyl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

802

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-methoxy-ethoxy)-N-(2,2,3,3,4,4,5,5,5-

nonafluoro-pentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

803

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(4-trifluoromethyl-

pyridin-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

804

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(4-bromo-phenyl)-

3H-imidazo[4,5-b]pyridine-6-carboxamide;

805

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-((2-trifluoromethyl-

phenyl)-methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

806

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-((3-trifluoromethyl-

pyridin-2-yl)-methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

807

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(2,2,3,3,4,4,5,5,5-

nonafluoro-pentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

808

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-methoxy-ethoxy)-N-(4-trifluoromethyl-

pyridin-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

809

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-(acetyl-methyl-amino)-ethoxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoro-pentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

810

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-(acetyl-methyl-amino)-ethoxy)-N-(4-

bromo-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

811

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-(acetyl-methyl-amino)-ethoxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoro-pentyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

812

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-methoxy-ethoxy)-N-(4-bromo-phenyl)-3-

methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

813

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-((3-

trifluoromethyl-pyridin-2-yl)-methyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

814

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

815

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(4-

trifluoromethyl-pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

816

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(4-bromo-

phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

817

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(4-

trifluoromethyl-pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

818

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(4-bromo-

phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

819

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(4-

trifluoromethyl-pyridin-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

820

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(4-bromo-

phenyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

821

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(4-

trifluoromethyl-pyridin-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

822

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(4-bromo-

phenyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

823

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

824

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(2-

trifluoromethyl-benzyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

825

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

826

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-((3-

trifluoromethyl-pyridin-2-yl)-methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

827

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

828

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(2-

trifluoromethyl-benzyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

829

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

830

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-((3-

trifluoromethyl-pyridin-2-yl)-methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

831

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-fluoro-ethoxy)-N-(4-trifluoromethyl-

pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

832

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-fluoro-ethoxy)-N-(4-bromo-phenyl)-3-

methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

833

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-fluoro-ethoxy)-N-(trans-4-trifluoromethyl-

cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

834

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-fluoro-ethoxy)-N-(2,2,3,3,4,4,5,5,5-

nonafluoropentyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

835

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-fluoro-ethoxy)-N-((3-trifluoromethyl-

pyridin-2-yl)-methyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

836

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(4-trifluoromethyl-

pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

837

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(4-bromo-phenyl)-3-

methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

838

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

839

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(2-trifluoromethyl-

benzyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

840

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(2,2,3,3,4,4,5,5,5-

nonafluoropentyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

841

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-((3-trifluoromethyl-

pyridin-2-yl)-methyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

842

2-(3,5-Dichloro-pyridin-4-ylamino)-5-ethoxy-N-(trans-4-trifluoromethyl-

cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

843

2-(3,5-Dichloro-pyridin-4-ylamino)-5-ethoxy-N-((3-trifluoromethyl-pyridin-2-yl)-

methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

844

2-(3,5-Dichloro-pyridin-4-ylamino)-5-ethoxy-N-(2,2,3,3,4,4,5,5,5-nonafluoro-

pentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

845

2-(3,5-Dichloro-pyridin-4-ylamino)-5-ethoxy-N-(4-trifluoromethyl-pyridin-2-yl)-3H-

imidazo[4,5-b]pyridine-6-carboxamide;

846

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(tetrahydrofuran-3-yl-oxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

847

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(tetrahydrofuran-3-yl-oxy)-N-((3-

trifluoromethyl-pyridin-2-yl)-methyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

848

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(tetrahydrofuran-3-yl-oxy)-N-(4-bromo-

phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

849

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(tetrahydrofuran-3-yl-oxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoro-pentyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

850

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(2,2,3,3,4,4,5,5,5-

nonafluoro-pentyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

851

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-((3-trifluoromethyl-

pyridin-2-yl)-methyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

852

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(4-trifluoromethyl-

pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

853

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(2-trifluoromethyl-

benzyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

854

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(2,2,3,3,4,4,5,5,5-

nonafluoro-pentyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

855

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-((3-trifluoromethyl-

pyridin-2-yl)-methyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

856

2-(3,5-Dichloro-pyridin-4-ylamino)-5-ethoxy-N-(4-bromo-phenyl)-3H-imidazo[4,5-

b]pyridine-6-carboxamide;

857

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(4-trifluoromethyl-

pyridin-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

858

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(4-bromo-phenyl)-

3H-imidazo[4,5-b]pyridine-6-carboxamide;

859

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2,2-trifluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

860

2-(2,6-Dichloro-phenylamino)-5-methoxy-N-((3-trifluoromethyl-pyridin-2-yl)-

methyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

861

2-(2,6-Dichloro-phenylamino)-5-methoxy-N-(2-trifluoromethyl-benzyl)-3-methyl-

3H-imidazo[4,5-b]pyridine-6-carboxamide;

862

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

863

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

864

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2-dimethylamino-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

865

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2-dimethylamino-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

866

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-methoxy-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

867

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2-methoxy-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3H-imidazo[4,5-b]pyridine-6-carboxamide;

868

2-(3,5-Dichloro-pyridin-4-ylamino)-5-(2-methoxy-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

869

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2-methoxy-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

870

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2-fluoro-ethoxy)-N-(trans-4-

trifluoromethyl-cyclohexyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

871

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-(2-

trifluoromethyl-benzyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide;

872

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2-difluoro-ethoxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide;

873

2-(2,6-Dichloro-4-fluoro-phenylamino)-5-(2,2,2-trifluoro-ethoxy)-N-

(2,2,3,3,4,4,5,5,5-nonafluoropentyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-

carboxamide.

4. A pharmaceutical formulation comprising a compound according to claim 1 , or a pharmaceutically-acceptable salt thereof, and a pharmaceutically acceptable adjuvant, diluent or carrier.