IP Library › Granted Patent US 8,076,488

Granted Patent B2

US 8,076,488 · App. 10/788,426 · Granted Dec 13, 2011

Bicyclic urea derivatives useful in the treatment of cancer and other disorders

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Quick Facts

Patent No.: US 8,076,488
App. No.: 10/788,426
Granted: Dec 13, 2011
Kind: B2

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Abstract

This invention relates to novel diaryl ureas, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for treating hyper-proliferative and angiogenesis disorders, as a sole agent or in combination with cytotoxic therapies.

Claims (567)

1. A compound of formula (I):

wherein

A is a bicyclic heterocycle which is:

(1) benzimidazolyl

(2) 1,3-benzothiazolyl

(3) 1,2,3-benzotriazolyl

(4) 1,3-benzoxazolyl

(5) 2,3-dihydro-1H-indolyl

(6) 2,3-dihydro-1H-indenyl

(7) 1,1-dioxido-2,3-dihydro-1-benzothienyl

(8) 1H-indazolyl

(9) 2H-indazolyl

(10) 1H-indolyl

(11) 2H-chromenyl

(12) quinoxalinyl or

(13) one of the formulae

optionally substituted with 1-4 substituents which are independently R 1 , OR 1 , S(O) p R 1 , C(O)R 1 , C(O)OR 1 , C(O)NR 1 R 2 , halogen, oxo, cyano, or nitro;

B is phenyl, naphthyl, or pyridyl, optionally substituted with 1-4 substituents which are independently C 1 -C 5 linear or branched alkyl, C 1 -C 5 linear or branched haloalkyl, C 1 -C 3 alkoxy, hydroxy, amino, C 1 -C 3 alkylamino, C 1 -C 6 dialkylamino, carboxyamide, halogen, cyano, nitro or S(O) p R 7 ;

L is:

(a) —(CH 2 ) m —O—(CH 2 ) l —,

(b) —(CH 2 ) m —(CH 2 ) l —,

(d) —(CH 2 ) m —NR 3 —(CH 2 ) l —,

(e) —(CH 2 ) m —NR 3 C(O)—(CH 2 ) l —,

(f) —(CH 2 ) m —S—(CH 2 ) l —,

(g) —(CH 2 ) m —C(O)NR 3 —(CH 2 ) l —, or

(h) a single bond;

m and l are integers independently selected from 0-4;

M is a pyridine ring, optionally substituted with 1-3 substituents which are independently C 1 -C 5 linear or branched alkyl, C 1 -C 5 linear or branched haloalkyl, C 1 -C 3 alkoxy, hydroxy, amino, C 1 -C 3 alkylamino, C 1 -C 6 dialkylamino, halogen, or nitro;

Q is C(O)R 4 , C(O)OR 4 or C(O)NR 4 R 5 ;

each of R 1 , R 2 , R 3 , R 4 and R 5 is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl,

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl,

(f) —(CH 2 ) q —X, wherein X is a 5 or 6 membered heterocyclic ring, containing at least one atom selected from oxygen, nitrogen and sulfur, which is saturated, partially saturated, or aromatic, or a 8-10 membered bicyclic heteroaryl having 1-4 heteroatoms which are O, N or S, or

(g) —(CH 2 ) q —Y, where Y is C(O)R 6 , C(O)OR 6 and C(O)NR 6 R 7 ;

each of R 6 -R 7 is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl, or

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl;

each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 , other than per-halo substituted C 1 -C 5 linear or branched alkyl, is optionally substituted with 1-3 substituents which are independently C 1 -C 5 linear or branched alkyl, up to perhalo substituted C 1 -C 5 linear or branched alkyl, C 1 -C 3 alkoxy, hydroxy, carboxy, amino, C 1 -C 3 alkylamino, C 1 -C 6 dialkylamino, halogen, cyano, or nitro;

p is an integer selected from 0, 1, or 2; and

q is an integer selected from 1, 2, 3, or 4,

or a pharmaceutically acceptable salt of formula I or an oxidized derivative of formula I wherein one or more urea nitrogens are substituted with a hydroxyl group, or an oxidized derivative of formula I wherein the nitrogen atom of pyridine ring M is in the oxide form, or a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl ester or phenyl C 1 -C 5 alkyl ester of formula I at a carboxylic acid group or amide group.

2. A compound of claim 1 wherein A and B follow one of the following combinations:

A=1H-benzimidazol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=1H-benzimidazol-6-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzodioxin-6-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzodioxin-7-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzodioxin-8-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzodioxol-4-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzodioxol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzothiazol-2-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzothiazol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzothiazol-6-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,2,3-benzotriazol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,3-benzoxazol-2-yl; and B=phenyl, pyridinyl or naphthyl, or

A=1,3-benzoxazol-6-yl; and B=phenyl, pyridinyl or naphthyl.

3. A compound of claim 1 wherein A and B follow one of the following combinations:

A=1H-benzimidazolyl; and B=phenyl or pyridinyl,

A=1,3-benzodioxinyl; and B=phenyl or pyridinyl,

A=1,3-benzodioxolyl; and B=phenyl or pyridinyl,

A=1,3-benzothiazolyl; and B=phenyl or pyridinyl,

A=1,2,3-benzotriazolyl; and B=phenyl or pyridinyl, or

A=1,3-benzoxazolyl; and B=phenyl or pyridinyl.

4. A compound of claim 1 wherein A and B follow one of the following combinations:

A=1H-benzimidazol-5-yl; and B=phenyl or pyridinyl,

A=1H-benzimidazol-6-yl; and B=phenyl or pyridinyl,

A=1,3-benzodioxin-6-yl; and B=phenyl or pyridinyl,

A=1,3-benzodioxin-7-yl; and B=phenyl or pyridinyl,

A=1,3-benzodioxin-8-yl; and B=phenyl or pyridinyl,

A=1,3-benzodioxol-4-yl; and B=phenyl or pyridinyl,

A=1,3-benzodioxol-5-yl; and B=phenyl or pyridinyl,

A=1,3-benzothiazol-2-yl; and B=phenyl or pyridinyl,

A=1,3-benzothiazol-5-yl; and B=phenyl or pyridinyl,

A=1,3-benzothiazol-6-yl; and B=phenyl or pyridinyl,

A=1,2,3-benzotriazol-5-yl; and B=phenyl or pyridinyl,

A=1,3-benzoxazol-2-yl; and B=phenyl or pyridinyl, or

A=1,3-benzoxazol-6-yl; and B=phenyl or pyridinyl.

5. A compound of claim 1 wherein A and B follow one of the following combinations:

A=2,3-dihydro-1,4-benzodioxin-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=2,3-dihydro-1,4-benzodioxin-6-yl; and B=phenyl, pyridinyl or naphthyl,

A=2,3-dihydro-1-benzofuran-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=2,3-dihydro-1H-indol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=2,3-dihydro-1H-indol-6-yl; and B=phenyl, pyridinyl or naphthyl,

A=2,3-dihydro-1H-inden-4-yl; and B=phenyl, pyridinyl or naphthyl,

A=2,3-dihydro-1H-inden-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=1,1-dioxido-2,3-dihydro-1-benzothien-6-yl; and B=phenyl, pyridinyl or naphthyl.

6. A compound of claim 1 wherein A and B follow one of the following combinations:

A=2,3-dihydro-1,4-benzodioxin-5-yl; and B=phenyl or pyridinyl,

A=2,3-dihydro-1,4-benzodioxin-6-yl; and B=phenyl or pyridinyl,

A=2,3-dihydro-1-benzofuran-5-yl; and B=phenyl or pyridinyl,

A=2,3-dihydro-1H-indol-5-yl; and B=phenyl or pyridinyl,

A=2,3-dihydro-1H-indol-6-yl; and B=phenyl or pyridinyl,

A=2,3-dihydro-1H-inden-4-yl; and B=phenyl or pyridinyl,

A=2,3-dihydro-1H-inden-5-yl; and B=phenyl or pyridinyl, or

A=1,1-dioxido-2,3-dihydro-1-benzothien-6-yl; and B=phenyl or pyridinyl.

7. A compound of claim 1 wherein A and B follow one of the following combinations:

A=1H-indazol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=2H-indazol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=1H-indazol-6-yl; and B=phenyl, pyridinyl or naphthyl,

A=1H-indol-5-yl; and B=phenyl, pyridinyl or naphthyl,

A=2-oxo-2H-chromen-7-yl; and B=phenyl, pyridinyl or naphthyl or

A=1oxo-2,3-dihydro-1H-inden-5-yl; and B=phenyl, pyridinyl or naphthyl.

8. A compound of claim 1 wherein A and B follow one of the following combinations:

A=1H-indazol-5-yl; and B=phenyl or pyridinyl,

A=2H-indazol-5-yl; and B=phenyl or pyridinyl,

A=1H-indazol-6-yl; and B=phenyl or pyridinyl,

A=1H-indol-5-yl; and B=phenyl or pyridinyl,

A=2-oxo-2H-chromen-7-yl; and B=phenyl or pyridinyl, or

A=1-oxo-2,3-dihydro-1H-inden-5-yl; and B=phenyl or pyridinyl.

9. A compound of claim 1 wherein A and B follow one of the following combinations:

A=quinoxalin-2-yl; and B=phenyl, pyridinyl or naphthyl or

A=quinoxalin-6-yl; and B=phenyl , pyridinyl or naphthyl.

10. A compound of claim 1 wherein A and B follow one of the following combinations:

A=quinoxalin-2-yl; and B=phenyl or pyridinyl, or

A=quinoxalin-6-yl; and B=phenyl or pyridinyl.

11. A compound as in claim 1 wherein L is —O— or —S—.

12. A compound which is:

N-methyl-4-[3-({[(2-methyl-1,3-benzoxazol-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-[4-({[(1-acetyl-2,3-dihydro-1H-indol-6-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[4-({[(6-chloro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-{4-[({[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino}carbonyl)amino]phen-oxy}pyridine-2-carboxamide

4-[4-({[(6-fluoro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[3-fluoro-4-({[(6-fluoro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-{3-fluoro-4-[({[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino}carbonyl)amino]phen-oxy}-N-methylpyridine-2-carboxamide;

4-[4-({[(6-methoxy-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[4-({[(5-chloro-1,3-benzoxazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[4-({[(6-chloro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide

4-(2-chloro-4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-[(5-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}quinolin-8-yl)oxy]-N-methylpyridine-2-carboxamide

4-[4-({[(4,6-difluoro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide

4-[3-fluoro-4-({[(6-methoxy-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-(4-{[({1-[2-(diethylamino)ethyl]-1H-indol -5-yl}amino)carbonyl]amino}-3-fluorophenoxy)-N-methylpyridine-2-carboxamide;

4-(4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}-3-fluorophenoxy)-N-methylpyridine-2-carboxamide

4-[3-fluoro-4-({[(1-oxo-2,3-dihydro-1H-inden-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[4-({[(1,1-dioxido-2,3-dihydro-1-benzothien-6-yl)amino]carbonyl}amino) -3-fluorophenoxy]-N-methylpyridine-2-carboxamide

4-[3-fluoro-4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[2-fluoro-4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[2,4-difluoro-5-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)-3-(trifluoromethyl)-phenoxy]pyridine-2-carboxamide

4-[4-fluoro-3-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[2-fluoro-5-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[2-chloro-6-fluoro-4-({[(1methyl-1H-indazol-5-yl) amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[3-fluoro-4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-(2-methoxyethyl)pyridine-2-carboxamide

4-[3-fluoro-4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[4-({[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]carbonyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-(4-{[(quinoxalin-6-ylamino)carbonyl]amino}phenoxy)pyridine-2carboxamide

4-(3-fluoro-4-{[(quinoxalin-6-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-[4-{[(quinoxalin-6-ylamino)carbonyl]amino}-3-(trifluoromethyl)phenoxy]-pyridine-2-carboxamide

4-(3-chloro-4-{[(quinoxalin-6-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)-3-(trifluoromethyl)phenoxy]pyridine-2-carboxamide

4-[4-({[(2-methyl-1,3-benzothiazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[4-({[(2-methyl-1,3-benzothiazol-5-yl)amino]carbonyl}amino)-3-(trifluoro-methyl)phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-methyl-4-({[(4-methyl-2-oxo-2H-chromen-7-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-methyl-4-({[(2-methyl-1,3-benzothiazol-5-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[3-fluoro-4-({[(2-methyl-1,3-benzothiazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-{[3-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]methyl}-pyridine-2-carboxamide

4-{[3-fluoro-4-({[(1-methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]methyl}-N-methylpyridine-2-carboxamide

4-[2-chloro-4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]N-methylpyridine-2-carboxamide

N-methyl-4-[3-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

N-methyl -4-[4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

4-[3-({[(2,2-difluoro-1,3-benzodioxol -5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[4-({[(2,2-difluoro-1,3-benzodioxol -5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[2-chloro-4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[2-chloro-4-({[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[3-chloro-4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[3-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-({[(1methyl-1H-indazol-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-(3-{[(2,3-dihydro-1-benzofuran-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-{3-[({[2-(trifluoromethyl)-1H-benzimidazol-5-yl]amino}carbonyl)amino]-phenoxy}pyridine-2-carboxamide

4-[4-chloro-3-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methyl-pyridine-2-carboxamide

4-[4-chloro-3-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[4-chloro-3-({[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[3-chloro-4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-[2-chloro-4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-[4-({[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]carbonyl}amino)-3-fluorophenoxy]-pyridine-2-carboxamide

4-[3-fluoro-4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

4-(4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(1oxo-2,3-dihydro-1H-inden-5-yl)amino]carbonyl}amino)phenoxy]-pyridine-2-carboxamide

5-[3-fluoro-4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]-N-methylnicotinamide

4-[4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}-3-(trifluoromethyl)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(1oxo-2,3-dihydro-1H-inden-5-yl)amino]carbonyl}amino) -3-(trifluoromethyl)phenoxy]pyridine-2-carboxamide

4-(3-chloro-4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}phenoxy)pyridine-2-carboxamide

4-[3-chloro-4-({[(1oxo-2,3-dihydro-1H-inden-5-yl)amino]carbonyl}amino)phenoxy]-pyridine-2-carboxamide

N-methyl-4-[4-{[(1methyl-1H-indazol-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-(4-{[(1,3-benzothiazol-6-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-(4-{[(2,3-dihydro-1-benzofuran-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-[2,4-dichloro-5-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[2,4-dichloro-5-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[3-chloro-4-({[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[3-chloro-4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]-N-methylpyridine-2-carboxamide;

4-(3-chloro-4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-(3-chloro-4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide;

4-[3-chloro-4-({[(1oxo-2,3-dihydro-1H-inden-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide;

4-[2-chloro-4-({[(1oxo-2,3-dihydro-1H-inden-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-(3-chloro-4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-[2,4-dichloro-5-({[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-{4-[({[1(methylsulfonyl)-2,3-dihydro-1H-indo1-5-yl]amino}carbonyl)amino]-phenoxy}pyridine-2-carboxamide

N-methyl-4-[3-nitro-4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[2-methyl-4-({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin -6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-[2,3-difluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

4-[3,5-difluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

4-[2,5-difluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[4({[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-5-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide trifluoroacetate

4-[3-fluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]-pyridine-2-carboxamide

4-[3-fluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

N-methyl-4-{[5-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-quinolin-8-yl]oxy}pyridine-2-carboxamide

4-(3-{[(1H-indazol-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide dihydrochloride

N-[2-(methylamino)-2-oxoethyl]-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-(3-fluoro-4-{[(quinoxalin-2-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-[2-(dimethylamino)-2-oxoethyl]-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-methyl-4-{[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

Methyl 4-[3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-7-yl)amino]carbonyl}-amino)phenoxy]-pyridine-2-carboxylate

4-[3-chloro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin -6yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

4-[3-chloro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-(3-{[(1,3-benzodioxol-5-ylamino)carbonyl]amino}phenoxy)-N -methylpyridine-2-carboxamide

N-methyl-4-[3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-(3-{[(2,3-dihydro-1,4-benzodioxin-6-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-[4-chloro-3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

5-[2-fluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]-N-methylnicotinamide

4-[2-chloro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[3-chloro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[3-fluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[3-fluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-(3-{[(1,3-benzodioxol-5-ylamino)carbonyl]amino}-4-chlorophenoxy)-N-methylpyridine-2-carboxamide

4-[4-chloro-3-({[(6-fluoro-4H-1,3-benzodioxin-8-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-(4-{[(1,3-benzodioxol -5-ylamino)carbonyl]amino}-3-fluorophenoxy)pyridine-2-carboxamide

4-[3-fluoro-4-({[(6-fluoro-4H-1,3-benzodioxin-8-yl)amino]carbonyl}amino)phenoxy]-pyridine-2-carboxamide

4-(4-chloro-3-{[(2,3-dihydro-1,4-benzodioxin-6-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-[3-({[(7-fluoro-2,3-dihydro-1,4-benzodioxin-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

4-[3-fluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

4-(4-{[(1,3-benzodioxol -5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

Methyl 4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxylate

Methyl 5-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]nicotinate

4-[2,4-dichloro-5-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-5-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]nicotinamide

4-(4-{[(1,3-benzodioxol-5-ylamino)carbonyl]amino}-3-chlorophenoxy)-N-methylpyridine-2-carboxamide

4-[3-chloro-4-({[(6-fluoro-4H-1,3-benzodioxin-8-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[2-methyl-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-nitro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide 1-oxide

4-[3-({[(1-methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-(2-pipendin-1-ylethyl)pyridine-2-carboxamide

4-[3-({[(1-methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-(2-pyrrolidin-1-ylethyl)pyridine-2-carboxamide

4-[3-({[(1-methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-pyridin-3-ylpyridine-2-carboxamide

N-[3-(1H-imidazol-1-yl)propyl]-4-[3-({[(1-methyl-1H-indazol-5-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

N-(2-pipendin-1-ylethyl)-4-[3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-(2-pyrrolidin-1-ylethyl)-4-[3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-pyridin-3-yl-4-[3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

N-[3-(1H-imidazol-1yl)propyl]-4-[3-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-[3-(1H-imidazol-1-yl)propyl]-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-(2-pyrrolidin-1-ylethyl)-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-(2-piperidin-1-ylethyl)-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-(2-piperazin-1-ylethyl)-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-pyridin-2-yl-4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-(2-pyrrolidin-1-ylethyl)pyridine-2-carboxamide

4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-(2-piperazin-1ylethyl)pyridine-2-carboxamide

4-[2-methoxy-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-(4-{[(2,3-dihydro-1H-inden-5-ylamino)carbonyl]amino}-2-methoxyphenoxy)pyridine-2-carboxamide

4-[2,5-difluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[3,5-difluoro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[3-(aminocarbonyl)-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}-amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-(methylsulfonyl)-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-[3-(methylthio)-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-[3-fluoro-4-({[(6-nitro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(6-nitro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-[4-({[(4,6-difluoro-1,3-benzothiazol-2-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(2-methyl-1,3-benzoxazol-6-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-(4-{[(2,3-dihydro-1H-inden-4-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-[4-({[(2,2-difluoro-1,3-benzodioxol-4-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(2-methyl-2H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

4-(4-{[({1-[2-(diethylamino)ethyl]-1H-indazol-5-yl}amino)carbonyl]amino}-3-fluorophenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-[4-({[(2-methyl-1H-indol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-{4-[(2-acetylpyridin-4-yl)oxy]phenyl}-N′-(1-methyl-1H-indazol-5- yl)urea

N-[2-(dimethylamino)-2-oxoethyl]-4 -[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}-aminophenoxy]pyridine-2-carboxamide

N-methyl-4-[4-({[(2-methyl-1,3-benzothiazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-methyl-4-{[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]methyl}-pyridine-2-carboxamide

4-(3-{[(1H-1,2,3-benzotriazol-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

Methyl 4-[3-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxylate

4-(4-{[(1H-1,2,3-benzotriazol-5-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

4-(4-{[(1H-indazol-6-ylamino)carbonyl]amino}phenoxy)-N-methylpyridine-2-carboxamide

N-methyl-4-{4-[({[2-(trifluoromethyl)-1H-benzimidazol-5-yl]amino}carbonyl)amino]-phenoxy}pyridine-2-carboxamide

4-[4-({[(1-ethyl-2-methyl-1H-benzimidazol-5-yl)amino]carbonyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

Methyl 4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxylate

4-[2-chloro-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-7-yl)amino]carbonyl}amino)-phenoxy]-N-methylpyridine-2-carboxamide

4-(4-{[(2,3-dihydro-1,4-benzodioxin-6-ylamino)carbonyl]amino}phenoxy)-N-[3-(1H-imidazol-1-yl)propyl]pyridine-2-carboxamide

4-(4-{[(2,3-dihydro-1,4-benzodioxin-6-ylamino)carbonyl]amino}phenoxy)-N-(2-pyrrolidin-1-ylethyl)pyridine-2-carboxamide

N-[3-(1H-imidazol-1yl)propyl]-4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)-phenoxy]pyridine-2-carboxamide

4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-N-(2-piperidin-1-ylethyl)pyridine-2-carboxamide

N-cyclopropyl-4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide

N-(cyclopropylmethyl)-4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-pyridine-2-carboxamide

N-cyclobutyl-4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide or

Methyl-N-({4-[4-({[(1methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}carbonyl)glycinate.

13. A pharmaceutical composition which comprises an effective amount of at least one compound of claim 1 and a physiologically acceptable carrier.

14. A compound of formula (I):

wherein

Q is C(O)R 4 , C(O)OR 4 or C(O)NR 4 R 5 ;

wherein A is a bicyclic heterocycle which is:

(1) benzimidazol-5-yl

(2) benzimidazol-6-yl

(3) 1,3-benzothiazol-2-yl

(4) 1,3-benzothiazol-5-yl

(5) 1,3-benzothiazol-6-yl

(6) 1,2,3-benzotriazol-5-yl

(7) 1,3-benzoxazol-2-yl

(8) 1,3-benzoxazol-6-yl

(9) 2,3-dihydro-1H-indol-5-yl

(10) 2,3-dihydro-1H-indol-6-yl

(11) 2,3-dihydro-1H-inden-4-yl

(12) 2,3-dihydro-1H-inden-5-yl

(13) 1,1-dioxido-2,3-dihydro-1-benzothien-6-yl

(14) 1H-indazol-5-yl

(15) 2H-indazol-5-yl

(16) 1H-indazol-6-yl

(17) 1H-indol-5-yl

(18) 2-oxo-2H-chromen-7-yl

(19) 1-oxo-2,3-dihydro-1 H-inden-5-yl

(20) quinoxalin-2-yl

(21) quinoxalin-6-yl, or

(22) one of the formulae

optionally substituted with 1-4 substituents which are independently R 1 , OR 1 ,

S(O) p R 1 , C(O)R 1 , C(O)OR 1 , C(O)NR 1 R 2 , halogen, oxo, cyano, or nitro,

B is phenyl, optionally substituted with 1-4 substituents which are independently C 1 -C 5 linear or branched alkyl, C 1 -C 5 linear or branched haloalkyl, C 1 -C 3 alkoxy, hydroxy, amino, C 1 -C 3 alkylamino, C 1 -C 6 dialkylamino, carboxyamide, halogen, cyano, nitro or S(O) p R 7 ;

L is:

(a) —(CH 2 ) m —O—(CH 2 ) l —,

(b) —(CH 2 ) m —(CH 2 ) l —,

(d) —(CH 2 ) m —NR 3 —(CH 2 ) l —,

(e) —(CH 2 ) m —NR 3 C(O)—(CH 2 ) l —,

(f) —(CH 2 ) m —S—(CH 2 ) l —,

(g) —(CH 2 ) m —C(O)NR 3 —(CH 2 ) l —, or

(h) a single bond;

m and l are integers independently selected from 0-4;

Q is C(O)R 4 , C(O)OR 4 or C(O)NR 4 R 5 ;

each of R 1 , R 2 , R 3 , R 4 and R 5 , is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl,

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl,

(g) —(CH 2 ) q —Y, where Y is C(O)R 6 , C(O)OR 6 and C(O)NR 6 R 7 ;

each of R 6 -R 7 is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl, or

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl;

p is an integer selected from 0, 1, or 2; and

q is an integer selected from 1, 2, 3, or 4,

15. A compound of claim 14 wherein A is

(1) benzimidazol-5-yl

(2) benzimidazol-6-yl

(8) 1,3-benzoxazol-6-yl

(9) 2,3-dihydro-1H-indol-5-yl

(10) 2,3-dihydro-1H-indol-6-yl

(11) 2,3-dihydro-1H-inden-4-yl

(12) 2,3-dihydro-1H-inden-5-yl

(13) 1,1-dioxido-2,3-dihydro-1-benzothien-6-yl

(14) 1H-indazol-5-yl

(15) 2H-indazol-5-yl

(16) 1H-indazol-6-yl

(17) 1H-indol-5-yl

(18) quinoxalin-2-yl

(19) quinoxalin-6-yl, or

(20) one of the formulae

16. A compound of claim 14 wherein the optional substituents on bicyclic heterocycle A are independently R 1 , OR 1 , and halogen.

17. A compound as in claim 16 wherein B is phenyl optionally substituted with 1-4 substituents which are halogen.

18. A compound of claim 17 wherein L is —O—.

19. A compound of claim 18 wherein Q is C(O)NR 4 R 5 and each of R 4 and R 5 is independently hydrogen or C 1 -C 5 alkyl.

20. A compound of formula (I):

wherein

A is a bicyclic heterocycle which is:

(1) benzimidazol-5-yl

(2) benzimidazol-6-yl

(8) 1,3-benzoxazol-6-y1

(9) 2,3-dihydro-1H-indol-5-yl

(10) 2,3-dihydro-1H-indol-6-yl

(11) 2,3-dihydro-1H-inden-4-yl

(12) 2,3-dihydro-1H-inden-5-yl

(13) 1,1-dioxido-2,3-dihydro-1-benzothien-6-yl

(14) 1H-indazol-5-yl

(15) 2H-indazol-5-yl

(16) 1H-indazol-6-yl

(17) 1H-indol-5-yl

(18) quinoxalin-2-yl

(19) quinoxalin-6-yl, or

(20) one of the formulae

optionally substituted with 1-4 substituents which are independently R 1 , OR 1 , S(O) p R 1 , C(O)R 1 , C(O)OR 1 , C(O)NR 1 R 2 , halogen, oxo, cyano, or nitro,

B is phenyl, optionally substituted with halogen,

L is —O—,

M is a pyridine ring substituted only with Q,

Q is C(O)NHR 5 and R 5 is independently hydrogen or C 1 -C 5 alkyl,

and p is an integer selected from 0, 1, or 2

21. A compound of formula (I):

wherein

A is a bicyclic heterocycle which is:

(1) benzimidazolyl

(2) 1,3-benzothiazolyl

(3) 1,2,3-benzotriazolyl

(4) 1,3-benzoxazolyl

(5) 2,3-dihydro-1H-indolyl

(6) 2,3-dihydro-1H-indenyl

(7) 1,1-dioxido-2,3-dihydro-1-benzothienyl

(8) 1H-indazolyl

(9) 2H-indazolyl

(10) 1H-indolyl

(11) 2H-chromenyl

(12) quinoxalinyl or

(13) one of the formulae

optionally substituted with 1-4 substituents which are independently R 1 , OR 1 , S(O) p R 1 , C(O)R 1 , C(O)OR 1 , C(O)NR 1 R 2 , halogen, oxo, cyano, or nitro;

B is quinolinyl, optionally substituted with 1-4 substituents which are independently C 1 -C 5 linear or branched alkyl, C 1 -C 5 linear or branched haloalkyl, C 1 -C 3 alkoxy, hydroxy, amino, C 1 -C 3 alkylamino, C 1 -C 6 dialkylamino, carboxyamide, halogen, cyano, nitro or S(O) p R 7 ;

L is:

(a) —(CH 2 ) m —O—(CH 2 ) 1 —,

(b) —(CH 2 ) m —(CH 2 ) 1 —,

(d) —(CH 2 ) m —NR 3 —(CH 2 ) 1 —,

(e) —(CH 2 ) m —NR 3 C(O)—(CH 2 ) 1 —,

(f) —(CH 2 ) m —S—(CH 2 ) 1 —,

(g) —(CH 2 ) m —C(O)NR 3 —(CH 2 ) 1 —, or

(h) a single bond;

m and 1 are integers independently selected from 0-4;

Q is C(O)R 4 , C(O)OR 4 or C(O)NR 4 R 5 ;

each of R 1 , R 2 , R 3 , R 4 and R 5 is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl,

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl,

(f) —(CH 2 ) q -X, wherein X is a 5 or 6 membered heterocyclic ring, containing at least one atom selected from oxygen, nitrogen and sulfur, which is saturated, partially saturated, or aromatic, or a 8-10 membered bicyclic heteroaryl having 1-4 heteroatoms which are O, N or S, or

(g) —(CH 2 ) q -Y, where Y is C(O)R 6 , C(O)OR 6 and C(O)NR 6 R 7 ;

each of R 6 -R 7 is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl, or

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl;

p is an integer selected from 0, 1, or 2; and

q is an integer selected from 1, 2, 3, or 4,

22. A compound of claim 1 wherein A and B follow one of the following combinations:

A=1H-benzimidazol-5-yl; and B=quinolinyl,

A=1H-benzimidazol-6-yl; and B=quinolinyl,

A=1,3-benzodioxin-6-yl; and B=quinolinyl,

A=1,3-benzodioxin-7-yl; and B=quinolinyl,

A=1,3-benzodioxin-8-yl; and B=quinolinyl,

A=1,3-benzodioxol-4-yl; and B=quinolinyl,

A=1,3-benzodioxol-5-yl; and B=quinolinyl,

A=1,3-benzothiazol-2-yl; and B=quinolinyl,

A=1,3-benzothiazol-5-yl; and B=quinolinyl,

A=1,3-benzothiazol-6-yl; and B=quinolinyl,

A=1,2,3-benzotriazol-5-yl; and B=quinolinyl,

A=1,3-benzoxazol-2-yl; and B=quinolinyl or

A=1,3-benzoxazol-6-yl; and B=quinolinyl.

23. A compound of claim 1 wherein A and B follow one of the following combinations:

A=2,3-dihydro-1,4-benzodioxin-5-yl; and B=quinolinyl,

A=2,3-dihydro-1,4-benzodioxin-6-yl; and B=quinolinyl,

A=2,3-dihydro-1-benzofuran-5-yl; and B=quinolinyl,

A=2,3-dihydro-1H-indo1-5-yl; and B=quinolinyl,

A=2,3-dihydro-1H-indo1-6-yl; and B=quinolinyl,

A=2,3-dihydro-1H-inden-4-yl; and B=quinolinyl,

A=2,3-dihydro-1H-inden-5-yl; and B=quinolinyl, or

A=1,1-dioxido-2,3-dihydro-1-benzothien-6-yl; and B=quinolinyl.

24. A compound of claim 1 wherein A and B follow one of the following combinations:

A=1H-indazol-5-yl; and B=quinolinyl,

A=2H-indazol-5-yl; and B=quinolinyl,

A=1H-indazol-6-yl; and B=quinolinyl,

A=1H-indol-5-yl; and B=quinolinyl,

A=2-oxo-2H-chromen-7-yl; and B=quinolinyl or

A=1-oxo-2,3-dihydro-1H-inden-5-yl and B=quinolinyl.

25. A compound of claim 1 wherein A and B follow one of the following combinations:

A=quinoxalin-2-yl; and B=quinolinyl or

A=quinoxalin-6-yl; and B=quinolinyl.

26. A compound as in claim 21 wherein L is —O— —S—.

27. A pharmaceutical composition which comprises an effective amount of at least one compound of claim 21 and a physiologically acceptable carrier.

28. A compound of formula (I):

wherein

Q is C(O)R 4 , C(O)OR 4 or C(O)NR 4 R 5 ;

wherein A is a bicyclic heterocycle which is:

(1) benzimidazol-5-yl

(2) benzimidazol-6-yl

(3) 1,3-benzothiazol-2-yl

(4) 1,3-benzothiazol-5-yl

(5) 1,3-benzothiazol-6-yl

(6) 1,2,3-benzotriazol-5-yl

(7) 1,3-benzoxazol-2-yl

(8) 1,3-benzoxazol-6-yl

(9) 2,3-dihydro-1H-indo1-5-yl

(10) 2,3-dihydro-1H-indo1-6-yl

(11) 2,3-dihydro-1H-inden-4-yl

(12) 2,3-dihydro-1H-inden-5-yl

(13) 1,1-dioxido-2,3-dihydro-1-benzothien-6-yl

(14) 1H-indazol-5-yl

(15) 2H-indazol-5-yl

(16) 1H-indazol-6-yl

(17) 1H-indo1-5-yl

(18) 2-oxo-2H-chromen-7-yl

(19) 1-oxo-2,3-dihydro-1H-inden-5-yl

(20) quinoxalin-2-yl

(21) quinoxalin-6-yl, or

(22) one of the formulae

optionally substituted with 1-4 substituents which are independently R 1 , OR 1 , S(O) p R 1 , C(O)R 1 , C(O)OR 1 , C(O)NR 1 R 2 , halogen, oxo, cyano, or nitro

L is:

(a) —(CH 2 ) m —O—(CH 2 ) 1 —,

(b) —(CH 2 ) m —(CH 2 ) 1 —,

(d) —(CH 2 ) m —NR 3 —(CH 2 ) 1 —,

(e) —(CH 2 ) m —NR 3 C(O)—(CH 2 ) 1 —,

(f) —(CH 2 ) m —S—(CH 2 ) 1 —,

(g) —(CH 2 ) m —C(O)NR 3 —(CH 2 ) 1 —, or

(h) a single bond;

m and 1 are integers independently selected from 0-4;

each of R 1 , R 2 , R 3 , R 4 and R 5 , is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl,

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl,

(g) —(CH 2 ) q —Y, where Y is C(O)R 6 , C(O)OR 6 and C(O)NR 6 R 7 ;

each of R 6 -R 7 is independently:

(a) hydrogen,

(b) C 1 -C 5 linear, branched, or cyclic alkyl,

(d) C 1 -C 3 alkyl-phenyl, or

(e) up to per-halo substituted C 1 -C 5 linear or branched alkyl;

p is an integer selected from 0, 1, or 2; and

q is an integer selected from 1, 2, 3, or 4,

29. A compound of claim 28 wherein A is

(1) benzimidazol-5-yl

(2) benzimidazol-6-yl

(8) 1,3-benzoxazol-6-yl

(9) 2,3-dihydro-1H-indo1-5-yl

(10) 2,3-dihydro-1H-indo1-6-yl

(11) 2,3-dihydro-1H-inden-4-yl

(12) 2,3-dihydro-1H-inden-5-yl

(13) 1,1-dioxido-2,3-dihydro-l-benzothien-6-yl

(14) 1H-indazol-5-yl

(15) 2H-indazol-5-yl

(16) 1H-indazol-6-yl

(17) 1H-indo1-5-yl

(18) quinoxalin-2-yl

(19) quinoxalin-6-yl, or

(20) one of the formulae

30. A compound of claim 28 wherein the optional substituents on bicyclic heterocycle A are independently R 1 , OR 1 , and halogen.

31. A compound of claim 30 wherein L is —O—.

32. A compound of claim 31 wherein Q is C(O)NR 4 R 5 and each of R 4 and R 5 is independently hydrogen or C 1 -C 5 alkyl.

Assignments (3)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2009

From: BAYER PHARMACEUTICALS CORPORATION

To: BAYER HEALTHCARE LLC

Reel/Frame 023031/0963 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2008

From: BAYER PHARMACEUTICALS CORPORATION

To: BAYER HEALTHCARE LLC

Reel/Frame 021893/0640 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2004

From: DUMAS, JACQUES; BOYER, STEPHEN; VERMA, SHARAD; ADNANE, LILA; CHEN, YUANWEI; LEE, WENDY; PHILLIPS, BARTON; SMITH, ROGER; SCOTT, WILLIAM; BURKE, JENNIFER; CHEN, JIANQING; CHEN, ZHI; FAN, JIANMEI; MIRANDA, KARL; RAUDENBUSH, BRIAN; REDMAN, ANIKO; SHAO, JIANXING; SU, NING; WANG, GAN; YI, LIN; ZHU, QINGMING

To: BAYER PHARMACEUTICAL CORPORATION

Reel/Frame 015925/0710 →