JP2008507539A5 - - Google Patents
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- Publication number
- JP2008507539A5 JP2008507539A5 JP2007522715A JP2007522715A JP2008507539A5 JP 2008507539 A5 JP2008507539 A5 JP 2008507539A5 JP 2007522715 A JP2007522715 A JP 2007522715A JP 2007522715 A JP2007522715 A JP 2007522715A JP 2008507539 A5 JP2008507539 A5 JP 2008507539A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridinecarboxamide
- isoquinolinylamino
- phenyl
- dihydro
- 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.)
- Withdrawn
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- -1 7-isoquinolinyl Chemical group 0.000 claims 237
- 150000001875 compounds Chemical class 0.000 claims 33
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 9
- 229940079593 drug Drugs 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 239000002246 antineoplastic agent Substances 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229960003966 nicotinamide Drugs 0.000 claims 5
- 239000011570 nicotinamide Substances 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 4
- 229910019142 PO4 Inorganic materials 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 4
- 239000010452 phosphate Substances 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 3
- 229910002651 NO3 Inorganic materials 0.000 claims 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 3
- 229940077388 benzenesulfonate Drugs 0.000 claims 3
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 3
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 3
- 229940058213 medronate Drugs 0.000 claims 3
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical compound OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 3
- 229960001860 salicylate Drugs 0.000 claims 3
- 150000003839 salts Chemical group 0.000 claims 3
- NPWMLGSDABOHTK-HNNXBMFYSA-N (2s)-2-[4-[[2-(isoquinolin-7-ylamino)pyridine-3-carbonyl]amino]phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 NPWMLGSDABOHTK-HNNXBMFYSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 2
- DJMAGYPYQQKCTM-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-(2-methyl-1,3-benzothiazol-5-yl)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3C=C4N=C(SC4=CC=3)C)=CC=C21 DJMAGYPYQQKCTM-UHFFFAOYSA-N 0.000 claims 2
- LGUFRZSXVZRZQI-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-(3-methyl-4-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound C1=C(C)C(C(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 LGUFRZSXVZRZQI-UHFFFAOYSA-N 0.000 claims 2
- PESBGORKGLRGHQ-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-(3-oxo-4h-1,4-benzothiazin-6-yl)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(NC=3C=C4NC(=O)CSC4=CC=3)=O)=CC=C21 PESBGORKGLRGHQ-UHFFFAOYSA-N 0.000 claims 2
- AKSCHOXLLVBOFT-JOCHJYFZSA-N 2-(isoquinolin-7-ylamino)-n-[3-[[(2r)-oxolan-2-yl]methoxy]-5-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3C=NC=CC3=CC=2)=CC=1OC[C@H]1CCCO1 AKSCHOXLLVBOFT-JOCHJYFZSA-N 0.000 claims 2
- GDMJWPCFBRNRKH-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-[3-methoxy-5-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC(OC)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3C=NC=CC3=CC=2)=C1 GDMJWPCFBRNRKH-UHFFFAOYSA-N 0.000 claims 2
- WUPRNILYHOSCHC-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-[3-methyl-4-(1,1,2,2,2-pentafluoroethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(F)(F)C(F)(F)F)C(C)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3C=NC=CC3=CC=2)=C1 WUPRNILYHOSCHC-UHFFFAOYSA-N 0.000 claims 2
- OLPNNMJDBFQZQB-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-[4-(1,1,2,2,2-pentafluoroethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 OLPNNMJDBFQZQB-UHFFFAOYSA-N 0.000 claims 2
- ZCQJVITWBZAQDX-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-[4-(2-methylbutan-2-yl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(C)(C)CC)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 ZCQJVITWBZAQDX-UHFFFAOYSA-N 0.000 claims 2
- HTOPDFCQOYISPA-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 HTOPDFCQOYISPA-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- ZCWMAKVIEHLWLT-UHFFFAOYSA-N 5-fluoro-2-(isoquinolin-7-ylamino)-n-(3-methyl-4-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound C1=C(C)C(C(C)C)=CC=C1NC(=O)C1=CC(F)=CN=C1NC1=CC=C(C=CN=C2)C2=C1 ZCWMAKVIEHLWLT-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 108091008605 VEGF receptors Proteins 0.000 claims 2
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 230000000340 anti-metabolite Effects 0.000 claims 2
- 229940100197 antimetabolite Drugs 0.000 claims 2
- 239000002256 antimetabolite Substances 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 230000017531 blood circulation Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000012830 cancer therapeutic Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 2
- 229940088597 hormone Drugs 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 229940043355 kinase inhibitor Drugs 0.000 claims 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 2
- UFDGPOXUTKMJHQ-UHFFFAOYSA-N n-(1-acetyl-3,3-dimethyl-2h-indol-6-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC3=CC=C4C(C)(C)CN(C4=C3)C(=O)C)=CC=C21 UFDGPOXUTKMJHQ-UHFFFAOYSA-N 0.000 claims 2
- FVRUYZXEAVYBNU-UHFFFAOYSA-N n-(2-acetyl-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3C=C4CN(CC(C)(C)C4=CC=3)C(=O)C)=CC=C21 FVRUYZXEAVYBNU-UHFFFAOYSA-N 0.000 claims 2
- QXEDXOPALNBGJA-UHFFFAOYSA-N n-(3,3-dimethyl-1,2-dihydroindol-6-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3C=C4NCC(C4=CC=3)(C)C)=CC=C21 QXEDXOPALNBGJA-UHFFFAOYSA-N 0.000 claims 2
- CNSLKRCMYSGRPL-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3C=C4CNCC(C4=CC=3)(C)C)=CC=C21 CNSLKRCMYSGRPL-UHFFFAOYSA-N 0.000 claims 2
- NTGGEYBVJKZMAE-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-quinolin-7-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3C=C4NCCC(C4=CC=3)(C)C)=CC=C21 NTGGEYBVJKZMAE-UHFFFAOYSA-N 0.000 claims 2
- QDFHXWVTGSVHGY-UHFFFAOYSA-N n-(4,4-dimethyl-2-oxo-1,3-dihydroquinolin-7-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3C=C4NC(=O)CC(C4=CC=3)(C)C)=CC=C21 QDFHXWVTGSVHGY-UHFFFAOYSA-N 0.000 claims 2
- IUKOEGQRFWJYRS-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 IUKOEGQRFWJYRS-UHFFFAOYSA-N 0.000 claims 2
- BGUVJBTYKVDAKN-UHFFFAOYSA-N n-(5,5-dimethyl-7-oxo-6,8-dihydro-1,8-naphthyridin-2-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3N=C4NC(=O)CC(C4=CC=3)(C)C)=CC=C21 BGUVJBTYKVDAKN-UHFFFAOYSA-N 0.000 claims 2
- QBYGIMVDFAZWSF-UHFFFAOYSA-N n-(5-tert-butyl-1,2-oxazol-3-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3C=NC=CC3=CC=2)=N1 QBYGIMVDFAZWSF-UHFFFAOYSA-N 0.000 claims 2
- NMNURIBYRTZCEB-UHFFFAOYSA-N n-(6-tert-butylpyridin-3-yl)-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=NC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 NMNURIBYRTZCEB-UHFFFAOYSA-N 0.000 claims 2
- JQDMUABLBWELTJ-UHFFFAOYSA-N n-[2-(2-aminoacetyl)-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl]-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CN=CC2=CC(NC3=NC=CC=C3C(=O)NC=3C=C4CN(CC(C4=CC=3)(C)C)C(=O)CN)=CC=C21 JQDMUABLBWELTJ-UHFFFAOYSA-N 0.000 claims 2
- RHQHOQJDKYBTBE-SANMLTNESA-N n-[3,3-dimethyl-1-[(2s)-oxolane-2-carbonyl]-2h-indol-6-yl]-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C12=CC(NC(=O)C=3C(=NC=CC=3)NC=3C=C4C=NC=CC4=CC=3)=CC=C2C(C)(C)CN1C(=O)[C@@H]1CCCO1 RHQHOQJDKYBTBE-SANMLTNESA-N 0.000 claims 2
- WIMMDLMOPAFLOM-UHFFFAOYSA-N n-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 WIMMDLMOPAFLOM-UHFFFAOYSA-N 0.000 claims 2
- KZCPHXHBHXRAEB-UHFFFAOYSA-N n-[4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)phenyl]-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=CC(C(OC)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 KZCPHXHBHXRAEB-UHFFFAOYSA-N 0.000 claims 2
- OVEQFNZUXGSCFP-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3C=NC=CC3=CC=2)=C1 OVEQFNZUXGSCFP-UHFFFAOYSA-N 0.000 claims 2
- PTMIQGWFSGOMNB-UHFFFAOYSA-N n-[5-(azetidin-1-yl)pyridin-2-yl]-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3C=NC=CC3=CC=2)C=1C(=O)NC(N=C1)=CC=C1N1CCC1 PTMIQGWFSGOMNB-UHFFFAOYSA-N 0.000 claims 2
- CPTCWKFJRMRMPW-UHFFFAOYSA-N n-[6-(azetidin-1-yl)pyridin-3-yl]-2-(isoquinolin-7-ylamino)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NC=2C=C3C=NC=CC3=CC=2)C=1C(=O)NC(C=N1)=CC=C1N1CCC1 CPTCWKFJRMRMPW-UHFFFAOYSA-N 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 2
- 230000035755 proliferation Effects 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- NPWMLGSDABOHTK-OAHLLOKOSA-N (2r)-2-[4-[[2-(isoquinolin-7-ylamino)pyridine-3-carbonyl]amino]phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 NPWMLGSDABOHTK-OAHLLOKOSA-N 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- UNRGYOKKGXEYLG-UHFFFAOYSA-N 2-(1h-indazol-6-ylamino)-n-[6-(1-methylcyclopropyl)pyridin-3-yl]pyridine-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C(=NC=CC=2)NC=2C=C3NN=CC3=CC=2)C=NC=1C1(C)CC1 UNRGYOKKGXEYLG-UHFFFAOYSA-N 0.000 claims 1
- UCGSGXDEXQLMFO-UHFFFAOYSA-N 2-(2h-benzotriazol-5-ylamino)-n-(5-tert-butyl-1,2-oxazol-3-yl)pyridine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3N=NNC3=CC=2)=N1 UCGSGXDEXQLMFO-UHFFFAOYSA-N 0.000 claims 1
- BXPUHWFOLYYJRL-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-(1h-indazol-6-ylamino)-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NC=3C=C4NN=CC4=CC=3)N=CC=C2C1 BXPUHWFOLYYJRL-UHFFFAOYSA-N 0.000 claims 1
- WZQDTOPMGSZUBV-NRFANRHFSA-N 2-(isoquinolin-5-ylamino)-n-[3-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]-5-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CN1CCC[C@H]1COC1=CC(NC(=O)C=2C(=NC=CC=2)NC=2C3=CC=NC=C3C=CC=2)=CC(C(F)(F)F)=C1 WZQDTOPMGSZUBV-NRFANRHFSA-N 0.000 claims 1
- YIEVALXERPLBDY-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-(3-methyl-4-pyrrolidin-1-ylphenyl)pyridine-3-carboxamide Chemical compound CC1=CC(NC(=O)C=2C(=NC=CC=2)NC=2C=C3C=NC=CC3=CC=2)=CC=C1N1CCCC1 YIEVALXERPLBDY-UHFFFAOYSA-N 0.000 claims 1
- OYGNEUUTBZHCGO-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-(4-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 OYGNEUUTBZHCGO-UHFFFAOYSA-N 0.000 claims 1
- UOMTVJCDSUFYIM-UHFFFAOYSA-N 2-(isoquinolin-7-ylamino)-n-[4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=C(C=CN=C2)C2=C1 UOMTVJCDSUFYIM-UHFFFAOYSA-N 0.000 claims 1
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- JDXWJZCENICSSI-UHFFFAOYSA-N n-[4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)phenyl]-2-[(1-oxo-2,3-dihydroisoindol-4-yl)amino]pyridine-3-carboxamide Chemical compound C1=CC(C(OC)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CN=C1NC1=CC=CC2=C1CNC2=O JDXWJZCENICSSI-UHFFFAOYSA-N 0.000 claims 1
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| PCT/US2005/025800 WO2006012374A1 (en) | 2004-07-22 | 2005-07-20 | Substituted aryl-amine derivatives and methods of use |
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| US7507748B2 (en) * | 2004-07-22 | 2009-03-24 | Amgen Inc. | Substituted aryl-amine derivatives and methods of use |
| DE602005024148D1 (de) * | 2004-08-25 | 2010-11-25 | Univ Chicago | Verwendung der kombination aus temozolomid und tnf-alpha zur behandlung von glioblastoma |
| WO2009051244A1 (ja) | 2007-10-18 | 2009-04-23 | Takeda Pharmaceutical Company Limited | 複素環化合物 |
| WO2011161217A2 (en) | 2010-06-23 | 2011-12-29 | Palacký University in Olomouc | Targeting of vegfr2 |
| US9302991B2 (en) * | 2010-10-18 | 2016-04-05 | Raqualia Pharma Inc. | Arylamide derivatives as TTX-S blockers |
| WO2012111016A1 (en) * | 2011-02-14 | 2012-08-23 | Council Of Scientific & Industrial Research | 2-anilino nicotinyl linked 2-amino benzothiazole conjugates and process for the preparation thereof |
| WO2012162291A1 (en) * | 2011-05-24 | 2012-11-29 | The Wistar Institute | Compositions and methods for modulating the activity of epstein-barr nuclear antigen 1 |
| KR101412794B1 (ko) * | 2011-07-27 | 2014-07-01 | 보령제약 주식회사 | 혈관생성억제 작용을 갖는 신규한 화합물, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
| UA112897C2 (uk) | 2012-05-09 | 2016-11-10 | Байєр Фарма Акцієнгезелльшафт | Біциклічно заміщені урацили та їх застосування для лікування і/або профілактики захворювань |
| WO2014058744A2 (en) | 2012-10-09 | 2014-04-17 | California Institute Of Technology | In vivo and in vitro olefin cyclopropanation catalyzed by heme enzymes |
| WO2014058729A1 (en) * | 2012-10-09 | 2014-04-17 | California Institute Of Technology | In vivo and in vitro carbene insertion and nitrene transfer reactions catalyzed by heme enzymes |
| KR101663864B1 (ko) * | 2013-04-19 | 2016-10-07 | 영남대학교 산학협력단 | 아미도피리딘올 유도체 또는 이의 약제학적 허용가능한 염을 유효성분으로 함유하는 염증성 장질환의 예방 또는 치료용 약학조성물 |
| US9399762B2 (en) | 2014-02-18 | 2016-07-26 | California Institute Of Technology | Methods and systems for sulfimidation or sulfoximidation of organic molecules |
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-
2005
- 2005-07-19 US US11/185,556 patent/US7507748B2/en not_active Expired - Fee Related
- 2005-07-20 CA CA2571627A patent/CA2571627C/en not_active Expired - Fee Related
- 2005-07-20 WO PCT/US2005/025800 patent/WO2006012374A1/en not_active Ceased
- 2005-07-20 AU AU2005267161A patent/AU2005267161B2/en not_active Ceased
- 2005-07-20 MX MX2007000672A patent/MX2007000672A/es active IP Right Grant
- 2005-07-20 JP JP2007522715A patent/JP2008507539A/ja not_active Withdrawn
- 2005-07-20 AT AT05791799T patent/ATE440834T1/de not_active IP Right Cessation
- 2005-07-20 EP EP05791799A patent/EP1773817B1/en not_active Expired - Lifetime
- 2005-07-20 DE DE602005016261T patent/DE602005016261D1/de not_active Expired - Lifetime
- 2005-07-20 ES ES05791799T patent/ES2331318T3/es not_active Expired - Lifetime
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2009
- 2009-01-29 US US12/322,361 patent/US8247430B2/en not_active Expired - Fee Related
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