JP2014513120A5 - - Google Patents
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- Publication number
- JP2014513120A5 JP2014513120A5 JP2014509330A JP2014509330A JP2014513120A5 JP 2014513120 A5 JP2014513120 A5 JP 2014513120A5 JP 2014509330 A JP2014509330 A JP 2014509330A JP 2014509330 A JP2014509330 A JP 2014509330A JP 2014513120 A5 JP2014513120 A5 JP 2014513120A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- amino
- thiazol
- hydroxy
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 5- {6-[(4-Cyclobutylpyridin-2-yl) amino] -4-methylpyridin-2-yl} -1,3-thiazol-2-yl Chemical group 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 150000003536 tetrazoles Chemical class 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 102000000551 Syk Kinase Human genes 0.000 claims 3
- 108010016672 Syk Kinase Proteins 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- CFRUPZABOQMKCQ-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(2h-triazol-4-yl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1C1=CNN=N1 CFRUPZABOQMKCQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- PLPFVQVPQSDKPP-UHFFFAOYSA-N 1-bromo-5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C(Br)=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 PLPFVQVPQSDKPP-UHFFFAOYSA-N 0.000 claims 1
- QKZPKSVDOCPZRM-UHFFFAOYSA-N 1-cyano-5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=C(C(=C(C(O)=O)C=C3)C#N)CCC2)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 QKZPKSVDOCPZRM-UHFFFAOYSA-N 0.000 claims 1
- VSZHJEDCDJLONV-UHFFFAOYSA-N 1-hydroxy-1-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-2,3-dihydroindene-4-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=C(C(=CC=C3)C(O)=O)CC2)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 VSZHJEDCDJLONV-UHFFFAOYSA-N 0.000 claims 1
- AYTXEKRLUZLIRO-UHFFFAOYSA-N 1-hydroxy-1-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-2,3-dihydroindene-5-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 AYTXEKRLUZLIRO-UHFFFAOYSA-N 0.000 claims 1
- PNKAWGMVXIAEAY-UHFFFAOYSA-N 3-fluoro-5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC(F)=C(C(O)=O)C=C3CCC2)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 PNKAWGMVXIAEAY-UHFFFAOYSA-N 0.000 claims 1
- VVDRPILAKHDJRT-UHFFFAOYSA-N 5-[5-[3,5-dibromo-4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C(Br)C(C)=C(Br)C=1NC1=CC(C(F)(F)F)=CC=N1 VVDRPILAKHDJRT-UHFFFAOYSA-N 0.000 claims 1
- NKZVAYATLJGLCB-UHFFFAOYSA-N 5-[5-[3-bromo-4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C(Br)C(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 NKZVAYATLJGLCB-UHFFFAOYSA-N 0.000 claims 1
- OEUADIBRAMZTMO-UHFFFAOYSA-N 5-[5-[4-acetamido-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(NC(=O)C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 OEUADIBRAMZTMO-UHFFFAOYSA-N 0.000 claims 1
- NFMSEOQFJLOMGS-UHFFFAOYSA-N 5-[5-[4-amino-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(N)=CC=1NC1=CC(C(F)(F)F)=CC=N1 NFMSEOQFJLOMGS-UHFFFAOYSA-N 0.000 claims 1
- RBRMYXQMGIWMSR-UHFFFAOYSA-N 5-[5-[5-bromo-4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound BrC=1C(C)=CC(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=NC=1NC1=CC(C(F)(F)F)=CC=N1 RBRMYXQMGIWMSR-UHFFFAOYSA-N 0.000 claims 1
- VWQKKAHJWNLXDK-UHFFFAOYSA-N 5-[5-[6-[(4-cyclobutyloxypyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1OC1CCC1 VWQKKAHJWNLXDK-UHFFFAOYSA-N 0.000 claims 1
- CADRNPXCAIYOFZ-UHFFFAOYSA-N 5-[5-[6-[(4-cyclohexyloxypyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1OC1CCCCC1 CADRNPXCAIYOFZ-UHFFFAOYSA-N 0.000 claims 1
- HCBQWBAQKUCWRP-UHFFFAOYSA-N 5-[5-[6-[(4-cyclohexylpyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1C1CCCCC1 HCBQWBAQKUCWRP-UHFFFAOYSA-N 0.000 claims 1
- KSASAGNLUPHYJX-UHFFFAOYSA-N 5-[5-[6-[(4-cyclopentyloxypyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1OC1CCCC1 KSASAGNLUPHYJX-UHFFFAOYSA-N 0.000 claims 1
- PXCUNDGCYQWEEF-UHFFFAOYSA-N 5-[5-[6-[(4-ethoxypyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound CCOC1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 PXCUNDGCYQWEEF-UHFFFAOYSA-N 0.000 claims 1
- PPOBWQXDXKYCNC-UHFFFAOYSA-N 5-[5-[6-[(4-ethylpyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound CCC1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 PPOBWQXDXKYCNC-UHFFFAOYSA-N 0.000 claims 1
- WMPRXXJICGIFFH-UHFFFAOYSA-N 5-[5-[6-[(4-tert-butylpyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(C)(C)C)=CC=N1 WMPRXXJICGIFFH-UHFFFAOYSA-N 0.000 claims 1
- IPCWPMKGLFZOGM-UHFFFAOYSA-N 5-[5-[6-[[4-(difluoromethyl)pyridin-2-yl]amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(F)F)=CC=N1 IPCWPMKGLFZOGM-UHFFFAOYSA-N 0.000 claims 1
- BMVADLQFFGSIDJ-UHFFFAOYSA-N 5-[5-[6-[[4-[4-(2-aminoethyl)piperazin-1-yl]pyridin-2-yl]amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1N1CCN(CCN)CC1 BMVADLQFFGSIDJ-UHFFFAOYSA-N 0.000 claims 1
- QFYBIVGGJCSWBY-UHFFFAOYSA-N 5-[5-[6-[[5-chloro-4-(trifluoromethyl)pyridin-2-yl]amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-5-hydroxy-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=C(Cl)C=N1 QFYBIVGGJCSWBY-UHFFFAOYSA-N 0.000 claims 1
- BZDPNAIFKATDSS-UHFFFAOYSA-N 5-acetamido-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound C1CCC2=CC(C(O)=O)=CC=C2C1(NC(=O)C)C(S1)=NC=C1C(N=1)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 BZDPNAIFKATDSS-UHFFFAOYSA-N 0.000 claims 1
- REBVQEZFKMRYTN-UHFFFAOYSA-N 5-amino-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(N)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 REBVQEZFKMRYTN-UHFFFAOYSA-N 0.000 claims 1
- FKOBAHHZUSXBIA-UHFFFAOYSA-N 5-hydroxy-1-methoxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C(OC)=C2CCCC1(O)C(S1)=NC=C1C(N=1)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 FKOBAHHZUSXBIA-UHFFFAOYSA-N 0.000 claims 1
- NOGBEJAUAKIDHX-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[(4-methylpyridin-2-yl)amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound CC1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 NOGBEJAUAKIDHX-UHFFFAOYSA-N 0.000 claims 1
- PANGETTYTUWTFZ-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[(4-piperazin-1-ylpyridin-2-yl)amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1N1CCNCC1 PANGETTYTUWTFZ-UHFFFAOYSA-N 0.000 claims 1
- KKTVBURDGTYPDU-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[(4-propan-2-ylpyridin-2-yl)amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound CC(C)C1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 KKTVBURDGTYPDU-UHFFFAOYSA-N 0.000 claims 1
- QBCYRLIFPWZAFG-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[(4-propylpyridin-2-yl)amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound CCCC1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 QBCYRLIFPWZAFG-UHFFFAOYSA-N 0.000 claims 1
- LXIZGPMVTRFUJA-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[(4-pyrazol-1-ylpyridin-2-yl)amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1N1C=CC=N1 LXIZGPMVTRFUJA-UHFFFAOYSA-N 0.000 claims 1
- IQMBHECVSOAQBU-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[(4-thiophen-3-ylpyridin-2-yl)amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1C=1C=CSC=1 IQMBHECVSOAQBU-UHFFFAOYSA-N 0.000 claims 1
- MZAZAGFIWASBSN-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(3-methylpyrazol-1-yl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N1=C(C)C=CN1C1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 MZAZAGFIWASBSN-UHFFFAOYSA-N 0.000 claims 1
- KTNJISCIFYFARB-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(4-methylpyrazol-1-yl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound C1=C(C)C=NN1C1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 KTNJISCIFYFARB-UHFFFAOYSA-N 0.000 claims 1
- MBQJUGGJAMEUOI-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound O1C(C)=NN=C1C1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 MBQJUGGJAMEUOI-UHFFFAOYSA-N 0.000 claims 1
- CGPASJOJARANMP-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(oxolan-3-yloxy)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC(N=CC=1)=CC=1OC1CCOC1 CGPASJOJARANMP-UHFFFAOYSA-N 0.000 claims 1
- OCQAZEACLVLCPN-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-1-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=CC(=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 OCQAZEACLVLCPN-UHFFFAOYSA-N 0.000 claims 1
- OKUYRLXBCYKBOD-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carbonitrile Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C#N)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 OKUYRLXBCYKBOD-UHFFFAOYSA-N 0.000 claims 1
- ARFNQZFUVYOZQV-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(N)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 ARFNQZFUVYOZQV-UHFFFAOYSA-N 0.000 claims 1
- CMHITQFLTSXUCO-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 CMHITQFLTSXUCO-UHFFFAOYSA-N 0.000 claims 1
- RKOFKUJSIQNSMM-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-n-(2h-tetrazol-5-yl)-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(=O)NC=2NN=NN=2)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 RKOFKUJSIQNSMM-UHFFFAOYSA-N 0.000 claims 1
- AMNZXNBWQGXTKX-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-n-(trifluoromethylsulfonyl)-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(=O)NS(=O)(=O)C(F)(F)F)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 AMNZXNBWQGXTKX-UHFFFAOYSA-N 0.000 claims 1
- FQIHMDJKBUZCET-UHFFFAOYSA-N 5-hydroxy-5-[5-[4-methyl-6-[[4-[(2-methylpropan-2-yl)oxy]pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=CC(C)=CC=1NC1=CC(OC(C)(C)C)=CC=N1 FQIHMDJKBUZCET-UHFFFAOYSA-N 0.000 claims 1
- PLNKGQHICRZXGJ-UHFFFAOYSA-N 5-hydroxy-5-[5-[6-[(4-methoxypyridin-2-yl)amino]-4-methylpyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxylic acid Chemical compound COC1=CC=NC(NC=2N=C(C=C(C)C=2)C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(O)=O)=C1 PLNKGQHICRZXGJ-UHFFFAOYSA-N 0.000 claims 1
- GDGOCEQHFUUBSU-UHFFFAOYSA-N 5-hydroxy-n-(4-methylphenyl)sulfonyl-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)C1=CC=C2C(C=3SC(=CN=3)C=3N=C(NC=4N=CC=C(C=4)C(F)(F)F)C=C(C)C=3)(O)CCCC2=C1 GDGOCEQHFUUBSU-UHFFFAOYSA-N 0.000 claims 1
- MLBVUHDKFGVEEM-UHFFFAOYSA-N 5-hydroxy-n-methoxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound C=1C(C(=O)NOC)=CC=C2C=1CCCC2(O)C(S1)=NC=C1C(N=1)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 MLBVUHDKFGVEEM-UHFFFAOYSA-N 0.000 claims 1
- HAABRXWJXIFASG-UHFFFAOYSA-N 5-hydroxy-n-methylsulfonyl-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(=O)NS(C)(=O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 HAABRXWJXIFASG-UHFFFAOYSA-N 0.000 claims 1
- SDNPEMVDTHPYTM-UHFFFAOYSA-N 6-bromo-1-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-3,4-dihydro-2h-naphthalen-1-ol Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(Br)C=C3CCC2)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 SDNPEMVDTHPYTM-UHFFFAOYSA-N 0.000 claims 1
- JWIKEEYVOMFXFM-UHFFFAOYSA-N 7-fluoro-6-(hydroxymethyl)-1-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-3,4-dihydro-2h-naphthalen-1-ol Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC(F)=C(CO)C=C3CCC2)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 JWIKEEYVOMFXFM-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- KRANMPGLKHWRMC-UHFFFAOYSA-N [5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalen-2-yl]boronic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)B(O)O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 KRANMPGLKHWRMC-UHFFFAOYSA-N 0.000 claims 1
- PZKZIBJVXYPHOW-UHFFFAOYSA-N [5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalen-2-yl]phosphonic acid Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)P(O)(O)=O)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 PZKZIBJVXYPHOW-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ZPUOIHGTFVTKPO-UHFFFAOYSA-N methyl 5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-1-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1CCCC2(O)C(S1)=NC=C1C(N=1)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 ZPUOIHGTFVTKPO-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- UBEWDBOMJPZACU-UHFFFAOYSA-N n-cyano-5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(=O)NC#N)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 UBEWDBOMJPZACU-UHFFFAOYSA-N 0.000 claims 1
- ALRGXDCFURSIAF-UHFFFAOYSA-N n-cyclopropylsulfonyl-5-hydroxy-5-[5-[4-methyl-6-[[4-(trifluoromethyl)pyridin-2-yl]amino]pyridin-2-yl]-1,3-thiazol-2-yl]-7,8-dihydro-6h-naphthalene-2-carboxamide Chemical compound N=1C(C=2SC(=NC=2)C2(O)C3=CC=C(C=C3CCC2)C(=O)NS(=O)(=O)C2CC2)=CC(C)=CC=1NC1=CC(C(F)(F)F)=CC=N1 ALRGXDCFURSIAF-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| EP2863916B1 (en) | 2012-06-22 | 2018-07-18 | Merck Sharp & Dohme Corp. | Substituted pyridine spleen tyrosine kinase (syk) inhibitors |
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-
2012
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- 2012-04-30 RU RU2013153540A patent/RU2612217C2/ru not_active IP Right Cessation
- 2012-04-30 EP EP12780029.0A patent/EP2704571B1/en active Active
- 2012-04-30 CA CA2834043A patent/CA2834043A1/en not_active Abandoned
- 2012-04-30 KR KR1020137031760A patent/KR20140025500A/ko not_active Abandoned
- 2012-04-30 CN CN201280032005.1A patent/CN103619170B/zh not_active Expired - Fee Related
- 2012-04-30 AU AU2012250958A patent/AU2012250958B8/en not_active Ceased
- 2012-04-30 MX MX2013012776A patent/MX2013012776A/es unknown
- 2012-04-30 BR BR112013028430A patent/BR112013028430A2/pt not_active Application Discontinuation
- 2012-04-30 WO PCT/US2012/035725 patent/WO2012151137A1/en not_active Ceased
- 2012-04-30 US US13/704,484 patent/US8796310B2/en active Active
- 2012-05-02 AR ARP120101538A patent/AR086236A1/es unknown
- 2012-05-04 TW TW101116052A patent/TW201247663A/zh unknown
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2014
- 2014-07-10 US US14/328,329 patent/US20140323440A1/en not_active Abandoned
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