IP Library Granted Patent US 8,367,706
Granted Patent B2
US 8,367,706 · App. 12/665,045 · Granted Feb 5, 2013

Inhibitors of janus kinases

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,367,706
App. No.
12/665,045
Granted
Feb 5, 2013
Kind
B2
Abstract

The instant invention provides for compounds that inhibit the four known mammalian JAK kinases (JAK1, JAK2, JAK3 and TYK2) and PDK1. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting the activity of JAK1, JAK2, JAK3 TYK2 and PDK1 by administering the compound to a patient in need of treatment for myeloproliferative disorders or cancer.

Claims (230)

1. A compound of formula I

wherein W is CR 4 ;

Y is CR 3 ;

Z is CR 2 ;

R 1 is hydrogen, halo, cyano or C 1-3 alkyl, wherein said alkyl group is optionally substituted with one to three halo;

R 2 is hydrogen, halo, cyano or C 1-3 alkyl, wherein said alkyl group is optionally substituted with one to three halo;

R 3 is hydrogen, halo, cyano, oxo, SO m R 8 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, R 11 , (C 1-6 alkyl)NR 7 R 8 , (C 1-6 alkyl)OR 12 , (C═O)NH 2 , NH(C═O)R 12 , NH(SO m R 8 ), N(SO m R 8 ) 2 , NHCH 2 (C 3-6 cycloalkyl), (C 1-6 alkyl)R 11 , O(C 1-6 alkyl)R 11 , CH 2 OR 11 , CH 2 NH(C═O)OR 12 , wherein said alkyl, alkenyl and alkynyl groups are optionally substituted with one to four substituents independently selected from the group consisting of halo and hydroxyl;

R 4 is hydrogen, halo, cyano, oxo, NR 6 R 7 , C 1-6 alkyl, (C 1-6 alkyl)OR 12 , OR 12 , (C═O)OR 12 , (C 1-6 alkyl)O(C 1-6 alkyl)OR 12 , (C 1-6 alkyl)O(C 1-6 alkyl)R 11 , CH 2 NR 10 CH 2 (C═O)NHR 11 , CH 2 NR 10 CH 2 (C═O)NHOR 12 , CH 2 NR 10 CH 2 CH 2 NH(C═O)OR 12 , CH 2 NR 10 (C═O)R 12 , CH 2 NR 10 CH 2 (C═O)R 11 , CH 2 NR 10 CH 2 (C═O)OR 12 , CH 2 NR 10 CH 2 (C═O)NHR 12 , CH 2 NR 10 CH 2 (C═O)NHR 11 , CH 2 NR 10 CH 2 (C═O)NHR 11 , CH 2 NR 10 CH 2 (C═O)NR 6 R 7 , CH 2 NR 10 CH 2 R 11 , CH 2 NR 10 R 11 , CH 2 NR 10 R 12 , CH═NOR 12 , CH 2 OCH 2 (C═O)NHCH 2 R 11 , CH 2 OCH 2 (C═O)R 11 , CH 2 OCH 2 (C═O)NHR 12 , CH 2 OCH 2 (C═O)NR 10 R 12 , CH 2 OR 11 , CH 2 O(C 2-7 alkynyl), CH 2 OR 12 , CH 2 O(C═O)NHR 12 , (C═O)NR 10 R 11 , (C═O)NR 10 CH 2 R 11 , (C═O)R 11 , (C═O)NR 10 CH 2 CH 2 R 11 , (C═O)NR 10 R 12 , (C═O)NH(C 1-6 alkenyl), CH(NH 2 )(C═O)NH 2 , CH(NH(C═O)CH 3 )((C═O)NH 2 , CH(NH(C═O)OCH 3 )((C═O)NH 2 ), CH 2 NH(C═O)OCH 3 , CH 2 NH(C═O)SO 2 CH 3 , CH 2 NH(C═O)R 10 , CH 2 NH(C═O)R 12 , CH 2 (C═O)NR 10 R 12 ), CH 2 (C═O)N(R 10 (C 2-6 alkynyl), C 1-6 alkyl(C═O)NR 10 R 11 , CHR 11 (C═O)NR 10 R 12 , (C═O)NR 10 R 12 , CHR 11 (C═O)OR 12 , CH 2 SO 2 R 12 , CH 2 SO 2 —(C 1-6 alkyl)-(C═O)NR 10 R 12 , CH 2 SO 2 R 11 , NHSO 2 NR 10 R 12 , SO 2 R 12 or R 11 , wherein said alkyl groups are optionally substituted with one to four substituents independently selected from the group consisting of halo, hydroxyl, cyano, NR 6 R 7 , CH 2 OR 12 , OP═O(CH 3 ) 2 , P═O(CH 3 )(OCH 3 ) and R 11 , and said alkenyl group is optionally substituted with one to three halo;

R 5 is aryl, wherein said aryl is optionally substituted with one to three substituents independently selected from the group consisting of halo, hydroxyl, cyano, R 12 , OR 12 , R 11 , NH 2 , (C 1-6 alkyl)R 11 , (C═O)R 11 , CH 2 NH(C═O)R 12 , CH 2 O(C═O)R 12 , SO m R 8 , CH 2 (trimethylsilyl), trimethylsilylethoxy and NH(C═O)OR 12 ;

R 6 is hydrogen or C 1-6 alkyl, wherein said alkyl group is optionally substituted with SO m , —NR 8 R 9 , hydroxyl or —OR 8 ;

R 7 is hydrogen or C 1-6 alkyl, wherein said alkyl group is optionally substituted with SO m , —NR 8 R 9 or —OR 8 ;

R 8 is hydrogen or C 1-6 alkyl;

R 9 is hydrogen or C 1-6 alkyl;

R 10 is hydrogen, carbobenzoxy, SO m R 8 , C 1-6 alkyl, (C 1-6 alkyl)OH or (C═O)H;

R 11 is hydrogen, C 3-6 cycloalkyl (which is optionally substituted with one to three substituents independently selected from the group consisting of fluoro, hydroxyl and (C 1-6 alkyl)OR 12 ), or aryl (which is optionally substituted with one to three substituents independently selected from the group consisting of halo and SO m R 8 );

R 12 is hydrogen or C 1-6 alkyl, wherein said alkyl group is optionally substituted with one to four substituents independently selected from the group consisting of halo, hydroxyl, cyano, SO m R 8 , P═O(CH 3 ) 2 , NR 8 R 9 and OR 8 ;

m is an integer from zero to two;

or a pharmaceutically acceptable salt or stereoisomer thereof.

2. The compound of claim 1 wherein R 5 is aryl, wherein said aryl group is substituted with one to three substituents independently selected from the group consisting of halo, R 12 , R 11 and SO m R 8 , or a pharmaceutically acceptable salt or stereoisomer thereof.

3. The compound of claim 2 wherein R 5 is aryl, wherein said aryl group is substituted with one to three substituents independently selected from the group consisting of halo and R 12 or a pharmaceutically acceptable salt or stereoisomer thereof.

4. The compound of claim 3 wherein R 5 is phenyl, wherein said phenyl group is substituted with one to three substituents independently selected from the group consisting of halo and R 12 ; R 12 is hydrogen or C 1-6 alkyl, wherein said alkyl group is optionally substituted with one to two hydroxyl; or a pharmaceutically acceptable salt or stereoisomer thereof.

5. The compound of claim 1 wherein R 4 is C 1-6 alkyl, CH 2 OR 12 , CH 2 O(C═O)NHR 12 or CH 2 SO 2 R 12 , wherein said alkyl group is optionally substituted with one to four substituents independently selected from the group consisting of hydroxyl and R 11 ; R 12 is C 1-6 alkyl, wherein said alkyl group is optionally substituted with one to two hydroxyl; or a pharmaceutically acceptable salt or stereoisomer thereof.

6. The compound of claim 5 wherein R 4 is CH 2 OR 12 ; R 12 is C 1-6 alkyl, wherein said alkyl group is optionally substituted with hydroxyl or a pharmaceutically acceptable salt or stereoisomer thereof.

7. The compound of claim 1 which is

5-(2,4-Difluorophenyl)-2-{[6-(hydroxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-(2-Fluorophenyl)-2-{[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-(2-Fluorophenyl)-2-{[6-(1-hydroxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-{[5-(1-Hydroxy-1-methylethyl)pyridin-2-yl]amino}-5-phenylthiophene-3-carboxamide;

5-phenyl-2-(pyridin-2-ylamino)thiophene-3-carboxamide;

2-[(6-methylpyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(4-methylpyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(5-methylpyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(3-methylpyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(5-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(3-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(4-fluoropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(4-cyanopyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(3-cyanopyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-[(5-cyanopyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

5-phenyl-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-phenyl-2-{[4-(trifluoromethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-[(5-chloropyridin-2-yl)amino]-5-phenylthiophene-3-carboxamide;

2-{[6-(hydroxymethyl)pyridin-2-yl]amino}-5-phenylthiophene-3-carboxamide;

5-phenyl-2-{[3-(trifluoromethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-phenyl-2-{[6-(trifluoromethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-{[5-(methylsulfonyl)pyridin-2-yl]amino}-5-phenylthiophene-3-carboxamide;

5-(2,5-dichlorophenyl)-2-{[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-methoxypyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-(pyridin-2-ylamino)thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-fluoropyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(4-fluoropyridin-2-yl)amino]thiophene-3-carboxamide;

2-[(6-cyanopyridin-2-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(5-fluoropyridin-2-yl)amino]thiophene-3-carboxamide;

2-[(5-cyanopyridin-2-yl)amino]-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(methylsulfonyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(methylsulfonyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-phenylpyridin-2-yl)amino]thiophene-3-carboxamide;

methyl6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridine-2-carboxylate;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridine-2-carboxylic acid;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(hydroxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2-hydroxy-1,2-dimethylpropyl)amino]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

2-({6-[(dimethylamino)methyl]pyridin-2-yl}amino)-5-(2-fluorophenyl)thiophene-3-carboxamide;

5-(2,5-dichlorophenyl)-2-({6-[(dimethylamino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-{[6-({[2-(cyclopentylamino)-2-oxoethyl]amino}methyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

ethyl N-{[6-({3-(aminocarbonyl)-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}glycinate;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[2-(dimethylamino)-2-oxoethyl]amino}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-[(6-{[[2-(dimethylamino)-2-oxoethyl](methyl)amino]methyl}pyridin-2-yl)amino]-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-(4-Fluorophenyl)-2-({6-[(methylamino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-((2-hydroxyethyl)amino)methyl)-2-pyridinyl)amino)-3-thiophenecarboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2-hydroxyethyl)(methyl)amino]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[2-(methylsulfonyl)ethyl]amino}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[(2S)-2-hydroxypropyl]amino}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[(1R)-2-hydroxy-1-methylethyl]amino}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2-hydroxy-2-methylpropyl)amino]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2-hydroxyethyl)amino]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[1-(hydroxymethyl)cyclopropyl]amino}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2,2,2-trifluoroethyl)amino]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(3,3,3-trifluoro-2-hydroxypropyl)amino]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

Tert-butyl [2-({[6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}amino)ethyl]carbamate;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(3-oxocyclopent-1-en-1-yl)amino]methyl}pyridine-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(3-oxocyclohex-1-en-1-yl)amino]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-hydroxypropyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-hydroxy-2-methylpropyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-{[6-(1,2-Dihydroxyethyl)pyridin-2-yl]amino}-5-(2-fluorophenyl)thiophene-3-carboxamide;

5-(4-Chlorophenyl)-2-{[6-(1,2-dihydroxy-1-methylethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-(4-Chlorophenyl)-2-({6-[(cis)-1,2-dihydroxy-1-methylpropyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-(2,5-dichlorophenyl)-2-{[6-(1,2-dihydroxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-{[6-(1,2-dihydroxyethyl)pyridin-2-yl]amino}-5-(4-fluorophenyl)thiophene-3-carboxamide;

2-({6-[(1S)-1,2-dihydroxy-1-methylethyl]pyridin-2-yl}amino)-5-[4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-({6-[(1R)-1,2-dihydroxy-1-methylethyl]pyridin-2-yl}amino)-5-[4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-(4-chlorophenyl)-2-({6-[(trans)-1,2-dihydroxy-1-methylpropyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[2-(isopropylamino)-2-oxoethyl]amino}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[({2-[(2-hydroxyethyl)amino]-2-oxoethyl}amino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

Benzyl{[6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}{2-[(2-hydroxyethyl)(methyl)amino]-2-oxoethyl}carbamate;

benzyl{[6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}(2-{[2-(methylsulfonyl)ethyl]amino}-2-oxoethyl)carbamate;

benzyl{[6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}{2-[(2-hydroxy-2-methylpropyl)amino]-2-oxoethyl}carbamate;

2-[(6-{[(2-{[2-(dimethylphosphoryl)ethyl]amino}-2-oxoethyl)amino]methyl}pyridin-2-yl)amino]-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-[(6-{[[2-(Cyclopentylamino)-2-oxoethyl](methylsulfonyl)amino]methyl}pyridin-2-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-[(6-{[[2-(Cyclopentylamino)-2-oxoethyl](methyl)amino]methyl}pyridin-2-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-{[6-({Acetyl[2-(cyclopentylamino)-2-oxoethyl]amino}methyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-(2,5-Dichlorophenyl)-2-{[6-(methoxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({2-[(2-hydroxyethyl)(methyl)amino]-2-oxoethoxy}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({2-[(2-hydroxyethyl)amino]-2-oxoethoxy}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-(2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-((2-((2-methoxyethyl)amino)-2-oxoethoxy)methyl)-2-pyridinyl)amino)-3-thiophenecarboxamide;

5-(2-fluoro-4-(1-hydroxy-1 methylethyl)phenyl)-2-((6-((2-oxo-2-(tetrahydro 2 furanylmethyl)amino)ethoxy)methyl)-2-pyridinyl)amino)-3-thiophenecarboxamide;

2-((6-((2-cyclohexylmethyl)amino)-2-oxoethoxy)methyl)-2-pyridinyl)amino)-5-(2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-3-thiophenecarboxamide;

2-((6-((2-((2-dimethylamino)ethyl)amino)-2-oxoethoxy)methyl)-2-pyridinyl)amino)-5-(2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-3-thiophenecarboxamide;

2-((6-((2-((2-dimethylamino)ethyl)amino)-2-oxoethoxy)methyl)-2-pyridinyl)amino)-5-(2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-3-thiophenecarboxamide;

[6-({3-(Aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl methylcarbamate;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-({6-[(2-Hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)-5-[4-(methylsulfonyl)phenyl]thiophene-3-carboxamide;

5-[4-(1-Hydroxy-1-methylethyl)phenyl]-2-({6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

5-[4-(1-cyano-1-methylethyl)phenyl]-2-({6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-{4-[(acetylamino)methyl]phenyl}-2-({6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-hydroxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-methoxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-ethoxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[2-(2-hydroxy-2-methylpropoxy)ethyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[(1R,2R)-2-hydroxycyclopentyl]oxy}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[(1R,2S)-2-hydroxycyclopentyl]oxy}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[(1R,2R)-2-hydroxycyclohexyl]oxy}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[(1R,2S)-2-hydroxycyclohexyl]oxy}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[(2S)-2-hydroxypropyl]oxy}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-isopropoxyethoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-({6-[(2,2-difluoroethoxy)methyl]pyridin-2-yl}amino)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-({6-[(cyclobutylmethoxy)methyl]pyridin-2-yl}amino)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(3,3,3-trifluoropropoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(3-methoxy-3-methylbutoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-[(6-{[2-(dimethylamino)ethoxy]methyl}pyridin-2-yl)amino]-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-({6-[(cyclopropylmethoxy)methyl]pyridin-2-yl}amino)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-[(6-{[(4-fluorobenzyl)oxy]methyl}pyridin-2-yl)amino]-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(hept-3-yn-1-yloxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(methoxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-{[6-(Ethoxymethyl)pyridin-2-yl]amino}-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-methoxyethoxy)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[2-(methylsulfonyl)ethoxy]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-hydroxyethoxy)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-{[6-(2-hydroxyethoxy)pyridin-2-yl]amino}-5-[4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-hydroxyethoxy)pyridin-2-yl]amino}thiophene-3-carboxamide;

6-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(trans-4-hydroxycyclohexyl)pyridine-2-carboxamide;

6-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(cyclopropylmethyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(trans-4-hydroxycyclohexyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(2-hydroxyethyl)-N-methylpyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(2-hydroxyethyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(2-hydroxyethyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(2-fluoroprop-2-en-1-yl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-methylpyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-ethyl-N-methylpyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(2-methoxyethyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(2-hydroxypropyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-(2-hydroxy-2-methylpropyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N,N-bis(2-hydroxyethyl)pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-[(1R)-2-hydroxy-1-methylethyl]pyridine-2-carboxamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

2-[(6-{[(Cyanoacetyl)amino]methyl}pyridin-2-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-{[6-(1-Cyano-3-hydroxypropyl)pyridin-2-yl]amino}-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-{[6-(cyanomethyl)pyridin-2-yl]amino}-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-{[6-(cyanomethyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[1-hydroxy-2-(methylamino)-2-oxoethyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-{[6-(2-amino-1-hydroxy-2-oxoethyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[2-(dimethylamino)-1-hydroxy-2-oxoethyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-{[6-(1-Cyano-1-methylethyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-{[6-(1-cyanoethyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methy lethyl)phenyl]thiophene-3-carboxamide;

2-{[6-(1-Cyanocyclopropyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-{[6-(2-Amino-1,1-dimethyl-2-oxoethyl)pyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2-hydroxy-2-methylpropyl)sulfonyl]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2-hydroxy-2-methylpropyl)sulfonyl]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(ethylsulfonyl)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-({6-[(tert-butylsulfonyl)methyl]pyridin-2-yl}amino)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(propylsulfonyl)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(isobutylsulfonyl)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(2-hydroxypropyl)sulfonyl]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(4-hydroxybutyl)sulfonyl]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-({[2-(methylamino)-2-oxoethyl]sulfonyl}methyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(isopropylsulfonyl)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({2-[(ethylsulfonyl)methyl]pyrimidin-4-yl}amino)thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(methylsulfonyl)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(methylsulfonyl)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(methylsulfonyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(methylsulfonyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-hydroxyethyl)(methyl)amino]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[3-(methylsulfonyl)phenyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

6-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N,N-dimethylnicotinamide;

6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-N-methylnicotinamide;

5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({5-[(dimethylamino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(5-{[(2-hydroxy-1,2-dimethylpropyl)amino]methyl}-6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({5-[(2-hydroxy-2-methylpropoxy)methyl]-6-methylpyridin-2-yl}amino)thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(2-fluoro-1-hydroxyethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(1-hydroxy-1-methylethyl)-6-methylpyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(1-hydroxyethyl)-6-methylpyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(1-hydroxyethyl)-6-methylpyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2-Fluoro-4-(1-methoxy-1-methylethyl)phenyl]-2-{[5-(1-methoxyethyl)-6-methylpyridin-2-yl]amino}thiophene-3-carboxamide;

2-{[6-Chloro-5-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-fluoro-5-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-fluoro-5-(methylsulfonyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

Methyl {[6-({3-(aminocarbonyl)-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)-2-methylpyridin-3-yl]methyl}carbamate;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(1-hydroxy-1-methylethyl)-6-methoxypyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(hydroxymethyl)-5-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}thiophene-3-carboxamide;

2-[(5-Cyano-6-methylpyridin-2-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-{[5-(Acetylamino)-6-methylpyridin-2-yl]amino}-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-methyl-5-[(methylsulfonyl)amino]pyridin-2-yl}amino)thiophene-3-carboxamide;

2-({5-[bis(Methylsulfonyl)amino]-6-methylpyridin-2-yl}amino)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

2-({5-[(Cyclopropylmethyl)amino]-6-methylpyridin-2-yl}amino)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[5-(3-hydroxy-3-methylbut-1-yn-1-yl)-6-methylpyridin-2-yl]amino}thiophene-3-carboxamide;

5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(3-hydroxy-3-methylbut-1-yn-1-yl)pyridin-2-yl]amino}thiophene-3-carboxamide;

[6-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl dimethylphosphinate;

Methyl {[6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}methylphosphinate;

5-(2,4-difluorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(4-fluorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(3-fluorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(2-fluorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(2,3-difluorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(2-chlorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(2,5-dichlorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-[2-chloro-5-(trifluoromethyl)phenyl]-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(3-chlorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

2-[(6-methylpyridin-2-yl)amino]-5-[3-(trifluoromethyl)phenyl]thiophene-3-carboxamide;

2-[(6-methylpyridin-2-yl)amino]-5-[4-(trifluoromethyl)phenyl]thiophene-3-carboxamide;

5-(5-chloro-2-fluorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(2-fluoro-5-methoxyphenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(3,4-dichlorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

5-(2,5-difluorophenyl)-2-[(6-methylpyridin-2-yl)amino]thiophene-3-carboxamide;

or a pharmaceutically acceptable salt or stereoisomer thereof.

8. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound according to claim 1 , and a pharmaceutically acceptable carrier.

Assignments (5)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
CHANGE OF NAME Recorded Nov 26, 2012
From: MERCK & CO., INC.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 029347/0338 →
MERGER Recorded Nov 26, 2012
From: MERCK SHARP & DOHME CORP.
To: SCHERING CORPORATION
Reel/Frame 029347/0897 →
CHANGE OF NAME Recorded Nov 26, 2012
From: SCHERING CORPORATION
To: MERCK SHARP & DOHME CORP.
Reel/Frame 029349/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 17, 2009
From: ALTMAN, MICHAEL; CHRISTOPHER, MATTHEW; GRIMM, JONATHAN B.; HAIDLE, ANDREW; KONRAD, KALEEN; LIM, JONGWON; MACCOSS, RACHEL N.; MACHACEK, MICHELLE; OSIMBONI, EKUNDAYO; OTTE, RYAN D.; SIU, TONY; SPENCER, KERRIE; TAOKA, BRANDON; TEMPEST, PAUL; WILSON, KEVIN; WOO, HYUN CHONG; YOUNG, JONATHAN; ZABIEREK, ANNA
To: MERCK & CO., INC.
Reel/Frame 023665/0693 →