IP Library › Granted Patent US 7,838,541

Granted Patent B2

US 7,838,541 · App. 10/361,858 · Granted Nov 23, 2010

Aryl ureas with angiogenesis inhibiting activity

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Quick Facts

Patent No.: US 7,838,541
App. No.: 10/361,858
Granted: Nov 23, 2010
Kind: B2

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USPTO Patent Center↗ Full Patent PDF↗

Abstract

This invention relates to methods of using aryl ureas to treat diseases mediated by the VEGF induced signal transduction pathway characterized by abnormal angiogenesis or hyperpermeability processes.

Claims (573)

1. A method for treating a disease in a human or other mammal wherein the disease that is treated is one or more of the following conditions: retinopathy and retinopathy of prematurity, comprising administering to a human or other mammal in need thereof the compound N-(4-chloro-3-(trifluoromethyl)phenyl)-N′-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea of the formula below or a pharmaceutically acceptable salt

thereof to regulate a VEGF-mediated signal transduction cascade,

2. A method for treating a disease in a human or other mammal wherein the disease that is treated is one or more of the following conditions: retinopathy and retinopathy of prematurity, comprising administering to a human or other mammal in need thereof the compound N-(4-chloro-3-(trifluoromethyl)phenyl)-N′-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea tosylate to regulate a VEGF-mediated signal transduction cascade.

3. A method of claim 1 wherein the compound of the formula VGFR, which is VEGF receptor-1 (fms-like tyrosine kinase-1(Flt-1)), VEGF receptor-2 (kinase insert domain containing receptor (KDR)); or VEGF receptor-3 (Flt-4).

4. A method of claim 3 wherein the inhibited VGFR is VEGF receptor-2 (KDR).

5. A method for treating a disease in a human or other mammal wherein the disease that is treated is one or more of the following conditions: retinopathy and retinopathy of prematurity, comprising administering to a human or other mammal in need thereof a compound which is

N-[5-(tert-butyl)-2-(3-thienyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

{[4-(4-methoxyphenoxy)phenyl]amino}-N-[2-methoxy-

5-(trifluoromethyl)phenyl]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[5-(tert-butyl)-2-methoxyphenyl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[5-(tert-butyl)-2-(3-thienyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(tert-butyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

{[3-(tert-butyl)phenyl]amino}-N-(4-(3-

pyridyl)phenyl)carboxamide

{[4-(4-methoxyphenoxy)phenyl]amino}-N-[2-methoxy-

5-(trifluoromethyl)phenyl]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]{[3-(2-

methyl(4-pyridyloxy))phenyl]amino}carboxamide

[(3-chloro-4-(6-quinolyloxy)phenyl)amino]-N-[2-

methoxy-5-(trifluoromethyl)phenyl]carboxamide

[(4-(4-pyridyloxy)phenyl)amino]-N-[3-

(trifluoromethyl)phenyl]carboxamide

N-[2-chloro-5-(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[2-fluoro-5-(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-(2-

methyl-4-(3-pyridyloxy)phenyl)carboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]{[4-(4-

methoxyphenoxy)phenyl]amino}carboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-[3-(4-

pyridylcarbonyl)phenyl]carboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-[3-(2-

methyl(4-pyridyloxy))phenyl]carboxamide

N-[4-fluoro-3-(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl][(4-

(4-pyridyloxy)phenyl)amino]carboxamide

N-[5-methoxy-3-(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

[(3-bromo-4-chlorophenyl)amino]-N-(4-(4-

pyridyloxy)phenyl)carboxamide

[(4-(4-pyridyloxy)phenyl)amino]-N-[3-

(trifluoromethoxy)phenyl]carboxamide

N-[3,5-bis(trifluoromethyl)phenyl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[5-(tert-butyl)isoxazol-3-yl][(4-(4-

pyridylthio)phenyl)amino]carboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[5-(tert-butyl)isoxazol-3-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[5-(tert-butyl)isoxazol-3-yl][(4-(3-

pyridyloxy)phenyl)amino]carboxamide

{3-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]phenyl}-N-

methylcarboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-[3-(2-methyl(4-

pyridyloxy))phenyl]carboxamide

N-[5-(tert-butyl)isoxazol-3-yl]{[4-(2-methyl(4-

pyridyloxy))phenyl]amino}carboxamide

4-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]pyridine-2-

carboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

4-[3-({N-[5-(tert-butyl)isoxazol-3-

yl]carbamoyl}amino)phenoxy]pyridine-2-carboxamide

3-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]benzamide

N-[3-(methylethyl)isoxazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-(3-cyclobutylisoxazol-5-yl)[(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-(3-cyclobutylisoxazol-5-yl)[(4-(6-

quinolyloxy)phenyl)amino]carboxamide

{[3-(tert-butyl)isoxazol-5-yl]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[3-(tert-butyl)isoxazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(tert-butyl)isoxazol-5-yl]{[4-(4-

methoxyphenoxy)phenyl]amino}carboxamide

N-[3-(1,1-dimethylpropyl)isoxazol-5-yl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[3-(1,1-dimethylpropyl)isoxazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

{[3-(tert-butyl)pyrazol-5-yl]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[3-(tert-butyl)pyrazol-5-yl][(4-(4-

pyridylthio)phenyl)amino]carboxamide

{3-[4-({[3-(tert-butyl)pyrazol-5-

yl]amino}carbonylamino)phenoxy]phenyl}-N-

methylcarboxamide, 2,2,2-trifluoroacetic acid

N-[3-(tert-butyl)-1-methylpyrazol-5-yl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-methylpyrazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-methylpyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-methylpyrazol-5-yl]{[4-(4-

pyridylmethoxy)phenyl]amino}carboxamide

tert-butyl 3-(tert-butyl)-5-[({4-[3-(N-

methylcarbamoyl)phenoxy]phenyl}amino)carbonylamino]

pyrazolecarboxylate

N-[5-(tert-butyl)(1,3,4-thiadiazol-2-yl)][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

{[5-(tert-butyl)(1,3,4-thiadiazol-2-yl)]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[5-(tert-butyl)(3-thienyl)][(4-(3-

pyridyloxy)phenyl)amino]carboxamide

N-[5-(tert-butyl)(3-thienyl)][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-(6-chloro(1H-indazol-3-yl))[(4-(4-

pyridyloxy)phenyl)amino]carboxamide

({4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-(1-methyl-3-

phenylpyrazol-5-yl)carboxamide

N-[5-(tert-butyl)isoxazol-3-yl][(4-(4-

pyridylthio)phenyl)amino]carboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[5-(tert-butyl)isoxazol-3-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[5-(tert-butyl)isoxazol-3-yl][(4-(3-

pyridyloxy)phenyl)amino]carboxamide

{3-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]phenyl}-N-

methylcarboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-[3-(2-methyl(4-

pyridyloxy))phenyl]carboxamide

N-[5-(tert-butyl)isoxazol-3-yl]{[4-(2-methyl(4-

pyridyloxy))phenyl]amino}carboxamide

{4-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy](2-pyridyl)}-N-

methylcarboxamide

4-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]pyridine-2-

carboxamide

4-[3-({N-[5-(tert-butyl)isoxazol-3-

yl]carbamoyl}amino)phenoxy]pyridine-2-carboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

3-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]benzamide

{4-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)-3-chlorophenoxy](2-

pyridyl)}-N-methylcarboxamide

{3-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]phenyl}-N-(2-

morpholin-4-ylethyl)carboxamide

{4-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy](2-pyridyl)}-N-

ethylcarboxamide

{4-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)-2-chlorophenoxy](2-

pyridyl)}-N-methylcarboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-{2-methyl-4-[2-

(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}carboxamide

{[5-(tert-butyl)isoxazol-3-yl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}carboxamide

{3-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenoxy]phenyl}-N-(3-

pyridyl)carboxamide

{4-[4-({[5-(tert-butyl)isoxazol-3-

yl]amino}carbonylamino)phenylthio](2-pyridyl)}-N-

methylcarboxamide

N-methyl{4-[4-({[3-(methylethyl)isoxazol-5-

yl]amino}carbonylamino)phenoxy](2-

pyridyl)}carboxamide

N-methyl{4-[3-({[3-(methylethyl)isoxazol-5-

yl]amino}carbonylamino)phenoxy](2-

pyridyl)}carboxamide

N-(3-cyclobutylisoxazol-5-yl)[(4-(6-

quinolyloxy)phenyl)amino]carboxamide

N-(3-cyclobutylisoxazol-5-yl)[(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(tert-butyl)isoxazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(tert-butyl)isoxazol-5-yl]{[4-(4-

methoxyphenoxy)phenyl]amino}carboxamide

{[3-(tert-butyl)isoxazol-5-yl]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[3-(tert-butyl)isoxazol-5-yl]{[4-(1,3-dioxoisoindolin-

5-yloxy)phenyl]amino}carboxamide

{[3-(tert-butyl)isoxazol-5-yl]amino}-N-[4-(1-

oxoisoindolin-5-yloxy)phenyl]carboxamide

{4-[4-({[3-(tert-butyl)isoxazol-5-

yl]amino}carbonylamino)phenoxy](2-pyridyl)}-N-

ethylcarboxamide

{4-[4-({[3-(tert-butyl)isoxazol-5-

yl]amino}carbonylamino)-2-chlorophenoxy](2-

pyridyl)}-N-methylcarboxamide

{[3-(tert-butyl)isoxazol-5-yl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}carboxamide

{4-[4-({[3-(tert-butyl)isoxazol-5-

yl]amino}carbonylamino)phenylthio](2-pyridyl)}-N-

methylcarboxamide

{4-[4-({[3-(tert-butyl)isoxazol-5-

yl]amino}carbonylamino)phenoxy](2-pyridyl)}-N-

methylcarboxamide

{[3-(tert-butyl)isoxazol-5-yl]amino}-N-[3-(6-methyl(3-

pyridyloxy))phenyl]carboxamide

N-[3-(tert-butyl)isoxazol-5-yl][(6-(4-pyridylthio)(3-

pyridyl))amino]carboxamide

{[3-(tert-butyl)isoxazol-5-yl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

N-[3-(1,1-dimethylpropyl)isoxazol-5-yl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[3-(1,1-dimethylpropyl)isoxazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(1,1-dimethylpropyl)isoxazol-5-yl]({4-[2-(N-

methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)carboxamide

N-[3-(1,1-dimethylpropyl)isoxazol-5-yl]{[4-(2-methyl(4-

pyridylthio))phenyl]amino}carboxamide

N-[3-(tert-butyl)pyrazol-5-yl]{[4-(6-methyl(3-

pyridyloxy))phenyl]amino}carboxamide

{[3-(tert-butyl)pyrazol-5-yl]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[3-(tert-butyl)pyrazol-5-yl][(4-(4-

pyridylthio)phenyl)amino]carboxamide

{3-[4-({[3-(tert-butyl)pyrazol-5-

yl]amino}carbonylamino)phenoxy]phenyl}-N-

methylcarboxamide, 2,2,2-trifluoroacetic acid

N-[3-(tert-butyl)-1-methylpyrazol-5-yl]{[4-(4-

pyridylmethoxy)phenyl]amino}carboxamide

{5-[4-({[3-(tert-butyl)-1-methylpyrazol-5-

yl]amino}carbonylamino)phenoxy]-2-methoxyphenyl}-

N-methylcarboxamide

N-[3-(tert-butyl)-1-methylpyrazol-5-yl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-methylpyrazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-methylpyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

tert-butyl 3-(tert-butyl)-5-[({4-[3-(N-

methylcarbamoyl)phenoxy]phenyl}amino)carbonylamino]

pyrazolecarboxylate

N-[5-(tert-butyl)(1,3,4-thiadiazol-2-yl)][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

{[5-(tert-butyl)(1,3,4-thiadiazol-2-yl)]amino}-N-(3-(4-

pyridylthio)phenyl)carboxamide

N-[5-(tert-butyl)(1,3,4-thiadiazol-2-yl)]{[6-(6-methyl(3-

pyridyloxy))(3-pyridyl)]amino}carboxamide

N-[5-(1,1-dimethylpropyl)(1,3,4-thiadiazol-2-yl)][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[5-(1,1-dimethylpropyl)(1,3,4-thiadiazol-2-yl)][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[5-(tert-butyl)(3-thienyl)][(4-(3-

pyridyloxy)phenyl)amino]carboxamide

{3-[4-({[5-(tert-butyl)(1,3,4-oxadiazol-2-

yl)]amino}carbonylamino)phenoxy]phenyl}-N-

ethylcarboxamide

{3-[4-({[5-(tert-butyl)(1,3,4-oxadiazol-2-

yl)]amino}carbonylamino)phenoxy]phenyl}-N-

(methylethyl)carboxamide

{3-[4-({[5-(tert-butyl)(1,3,4-oxadiazol-2-

yl)]amino}carbonylamino)phenoxy]phenyl}-N-

methylcarboxamide

N-[5-(tert-butyl)(1,3,4-oxadiazol-2-yl)][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-(3-cyclopropyl-1-methylpyrazol-5-yl)[(4-(6-

quinolyloxy)phenyl)amino]carboxamide

({4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-(1-methyl-3-

phenylpyrazol-5-yl)carboxamide

N-[2-(tert-butyl)(1,3-thiazol-5-yl)]{[4-(6-methyl(3-

pyridyloxy))phenyl]amino}carboxamide

[(2,3-dichlorophenyl)amino]-N-[3-(tert-butyl)-1-phenylpyrazol-

5-yl]carboxamide

N-[1-(4-aminophenyl)-3-(tert-butyl)pyrazol-5-yl][(2,3-

dichlorophenyl)amino]carboxamide

N-[1-(3-aminophenyl)-3-(tert-butyl)pyrazol-5-yl][(2,3-

dichlorophenyl)amino]carboxamide

N-[3-(3-(tert-butyl)-5-{[(4-phenoxyphenyl)

amino]carbonylamino}pyrazolyl)phenyl]acetamide

N-[1-(2,6-dichlorophenyl)-3-(tert-butyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(4-fluorophenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(2-methylphenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(3-fluorophenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-{3-(tert-butyl)-1-[4-(methylsulfonyl)phenyl]pyrazol-5-

yl}{[4-(4-pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(4-nitrophenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(3-methoxyphenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[1-(3-aminophenyl)-3-(tert-butyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[1-(3-aminophenyl)-3-(tert-butyl)pyrazol-5-yl][(4-(4-

pyridylthio)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-(3-fluorophenyl)pyrazol-5-yl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-(4-fluorophenyl)pyrazol-5-yl][(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-(3-fluorophenyl)pyrazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-[3-(tert-butyl)-1-(4-fluorophenyl)pyrazol-5-yl][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

[(2,3-dichlorophenyl)amino]-N-[3-(tert-butyl)-1-phenylpyrazol-

5-yl]carboxamide

N-[1-(4-aminophenyl)-3-(tert-butyl)pyrazol-5-yl][(2,3-

dichlorophenyl)amino]carboxamide

N-[1-(3-aminophenyl)-3-(tert-butyl)pyrazol-5-yl][(2,3-

dichlorophenyl)amino]carboxamide

N-[3-(3-(tert-butyl)-5-{[(4-phenoxyphenyl)

amino]carbonylamino}pyrazolyl)phenyl]acetamide

N-[1-(2,6-dichlorophenyl)-3-(tert-butyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(4-fluorophenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(2-methylphenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(3-fluorophenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-{3-(tert-butyl)-1-[4-(methylsulfonyl)phenyl]pyrazol-5-

yl}{[4-(4-pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(4-nitrophenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[3-(tert-butyl)-1-(3-methoxyphenyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[1-(3-aminophenyl)-3-(tert-butyl)pyrazol-5-yl]{[4-(4-

pyridylmethyl)phenyl]amino}carboxamide

N-[1-(3-aminophenyl)-3-(tert-butyl)pyrazol-5-yl][(4-(4-

pyridylthio)phenyl)amino]carboxamide

{3-[4-({[3-(tert-

butyl)phenyl]amino}carbonylamino)phenoxy]phenyl}-N-

methylcarboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

4-[3-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]pyridine-2-

carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

4-[4-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]pyridine-2-

carboxamide

{4-[4-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)-3-

methylphenoxy](2-pyridyl)}-N-methylcarboxamide

({2-chloro-4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-[2-methoxy-5-

(trifluoromethyl)phenyl]carboxamide

({4-[2-(N-ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)-N-[2-

methoxy-5-(trifluoromethyl)phenyl]carboxamide

({3-chloro-4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-[2-methoxy-5-

(trifluoromethyl)phenyl]carboxamide

3-[4-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]benzamide

({4-[2-(N,N-dimethylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-[2-methoxy-5-

(trifluoromethyl)phenyl]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}amino)carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}amino)carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(4-{5-[N-(2-

morpholin-4-ylethyl)carbamoyl](3-

pyridyloxy)}phenyl)amino]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[5-(N-

methylcarbamoyl)(3-pyridyloxy)]phenyl}amino)carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[3-(N-(3-

pyridyl)carbamoyl)phenoxy]phenyl}amino)carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-methylcarboxamide

4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]pyridine-

2-carboxamide

4-[3-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]pyridine-

2-carboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-{2-methyl-4-

[2-(N-methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{4-[3-chloro-4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-methylcarboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]({4-[2-(N-

ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

{3-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]phenyl}-

N-(2-morpholin-4-ylethyl)carboxamide

{3-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]phenyl}-

N-(2-piperidylethyl)carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenylthio](2-

pyridyl)}-N-methylcarboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-(2-morpholin-4-ylethyl)carboxamide

{5-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](3-

pyridyl)}-N-methylcarboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]({4-[3-(N-(3-

pyridyl)carbamoyl)phenoxy]phenyl}amino)carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-(2-hydroxyethyl)carboxamide

{4-[4-({[4-bromo-3-

(trifluoromethyl)phenyl]amino}carbonylamino)-2-

chlorophenoxy](2-pyridyl)}-N-methylcarboxamide

N-[4-bromo-3-(trifluoromethyl)phenyl]({4-[2-(N-

ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

{[4-bromo-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{[4-bromo-3-(trifluoromethyl)phenyl]amino}-N-{4-methyl-3-

[2-(N-methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{[4-bromo-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}carboxamide

{4-[4-({[4-bromo-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-(2-morpholin-4-ylethyl)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({2-chloro-

4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({3-chloro-

4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

{3-[4-({[3-(tert-

butyl)phenyl]amino}carbonylamino)phenoxy]phenyl}-N-

methylcarboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

4-[3-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]pyridine-2-

carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

4-[4-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]pyridine-2-

carboxamide

{4-[4-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)-3-

methylphenoxy](2-pyridyl)}-N-methylcarboxamide

({2-chloro-4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-[2-methoxy-5-

(trifluoromethyl)phenyl]carboxamide

({4-[2-(N-ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)-N-[2-

methoxy-5-(trifluoromethyl)phenyl]carboxamide

({3-chloro-4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-[2-methoxy-5-

(trifluoromethyl)phenyl]carboxamide

3-[4-({N-[2-methoxy-5-

(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]benzamide

({4-[2-(N,N-dimethylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)-N-[2-methoxy-5-

(trifluoromethyl)phenyl]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}amino)carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}amino)carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl][(4-{5-[N-(2-

morpholin-4-ylethyl)carbamoyl](3-

pyridyloxy)}phenyl)amino]carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[5-(N-

methylcarbamoyl)(3-pyridyloxy)]phenyl}amino)carboxamide

N-[2-methoxy-5-(trifluoromethyl)phenyl]({4-[3-(N-(3-

pyridyl)carbamoyl)phenoxy]phenyl}amino)carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-methylcarboxamide

4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]pyridine-

2-carboxamide

4-[3-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]pyridine-

2-carboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-{2-methyl-4-

[2-(N-methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{4-[3-chloro-4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-methylcarboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]({4-[2-(N-

ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

{3-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]phenyl}-

N-(2-morpholin-4-ylethyl)carboxamide

{3-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy]phenyl}-

N-(2-piperidylethyl)carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenylthio](2-

pyridyl)}-N-methylcarboxamide

{[4-chloro-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-(2-morpholin-4-ylethyl)carboxamide

{5-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](3-

pyridyl)}-N-methylcarboxamide

N-[4-chloro-3-(trifluoromethyl)phenyl]({4-[3-(N-(3-

pyridyl)carbamoyl)phenoxy]phenyl}amino)carboxamide

{4-[4-({[4-chloro-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-(2-hydroxyethyl)carboxamide

{4-[4-({[4-bromo-3-

(trifluoromethyl)phenyl]amino}carbonylamino)-2-

chlorophenoxy](2-pyridyl)}-N-methylcarboxamide

N-[4-bromo-3-(trifluoromethyl)phenyl]({4-[2-(N-

ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

{[4-bromo-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{[4-bromo-3-(trifluoromethyl)phenyl]amino}-N-{4-methyl-3-

[2-(N-methylcarbamoyl)(4-pyridyloxy)]phenyl}carboxamide

{[4-bromo-3-(trifluoromethyl)phenyl]amino}-N-{3-[2-(N-

methylcarbamoyl)(4-pyridylthio)]phenyl}carboxamide

{4-[4-({[4-bromo-3-

(trifluoromethyl)phenyl]amino}carbonylamino)phenoxy](2-

pyridyl)}-N-(2-morpholin-4-ylethyl)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({2-chloro-

4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({3-chloro-

4-[2-(N-methylcarbamoyl)(4-

pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({3-[2-(N-

methylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

N-[4-chloro-2-methoxy-5-(trifluoromethyl)phenyl]({4-[2-(N-

ethylcarbamoyl)(4-pyridyloxy)]phenyl}amino)carboxamide

[(4-fluorophenyl)amino]-N-(3-isoquinolyl)carboxamide

N-(2-methoxy(3-quinolyl))[(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-(2-methoxy(3-quinolyl))[(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[1-(4-methylpiperazinyl)(3-isoquinolyl)][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-(2-methoxy(3-quinolyl))[(4-(4-

pyridyloxy)phenyl)amino]carboxamide

N-(2-methoxy(3-quinolyl))[(3-(4-

pyridylthio)phenyl)amino]carboxamide

N-[1-(4-methylpiperazinyl)(3-isoquinolyl)][(4-(4-

pyridyloxy)phenyl)amino]carboxamide

or a pharmaceutically acceptable salt thereof to regulate a VEGF-mediated signal transduction cascade.

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 Jun 23, 2003

From: DUMAS, JACUES; SCOTT, WILLLIAM; ELTING, JAMES; HATOUM-MAKDAD, HOLIA

To: BAYER CORPORATION

Reel/Frame 014199/0169 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 9, 2003

From: BAYER CORPORATION

To: BAYER PHARMACEUTICALS CORPORATION

Reel/Frame 014125/0545 →