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- Withdrawn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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| US7507748B2 (en) * | 2004-07-22 | 2009-03-24 | Amgen Inc. | Substituted aryl-amine derivatives and methods of use |
| EP1781284B1 (en) * | 2004-08-25 | 2010-10-13 | The University of Chicago | Use of the combination comprising temozolomide and tnf-alpha for treating glioblastoma |
| EP2202223B1 (en) | 2007-10-18 | 2017-01-25 | Takeda Pharmaceutical Company Limited | Heterocyclic compound as blood rbp4 lowering agent |
| WO2011161217A2 (en) | 2010-06-23 | 2011-12-29 | Palacký University in Olomouc | Targeting of vegfr2 |
| EP2630122B1 (en) * | 2010-10-18 | 2016-11-30 | RaQualia Pharma Inc | Arylamide derivatives as ttx-s blockers |
| US9029553B2 (en) * | 2011-02-14 | 2015-05-12 | Council Of Scientific & Industrial Research | 2-anilino nicotinyl linked 2-amino benzothiazole conjugates and process for the preparation thereof |
| CN103717757A (zh) * | 2011-05-24 | 2014-04-09 | 威斯特研究所 | 用于调节爱泼斯坦-巴尔核抗原1的活性的组合物和方法 |
| 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 |
| JP2015534464A (ja) | 2012-10-09 | 2015-12-03 | カリフォルニア インスティチュート オブ テクノロジー | ヘム酵素によって触媒されるインビボおよびインビトロオレフィンシクロプロパン化 |
| 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 |
| KR101612179B1 (ko) * | 2013-04-19 | 2016-04-12 | 영남대학교 산학협력단 | 아미도피리딘올 유도체 또는 이의 약제학적 허용가능한 염을 유효성분으로 함유하는 암질환 예방 또는 치료용 약학조성물 |
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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 EP EP05791799A patent/EP1773817B1/en not_active Expired - Lifetime
- 2005-07-20 ES ES05791799T patent/ES2331318T3/es not_active Expired - Lifetime
- 2005-07-20 DE DE602005016261T patent/DE602005016261D1/de not_active Expired - Lifetime
- 2005-07-20 WO PCT/US2005/025800 patent/WO2006012374A1/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 AU AU2005267161A patent/AU2005267161B2/en not_active Ceased
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2009
- 2009-01-29 US US12/322,361 patent/US8247430B2/en not_active Expired - Fee Related
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