JP2015521634A5 - - Google Patents
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- JP2015521634A5 JP2015521634A5 JP2015518816A JP2015518816A JP2015521634A5 JP 2015521634 A5 JP2015521634 A5 JP 2015521634A5 JP 2015518816 A JP2015518816 A JP 2015518816A JP 2015518816 A JP2015518816 A JP 2015518816A JP 2015521634 A5 JP2015521634 A5 JP 2015521634A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- fluoro
- dihydro
- yloxy
- oxo
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims 36
- -1 hydroxy, amino, carboxy Chemical group 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 102000007399 Nuclear hormone receptor Human genes 0.000 claims 6
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 102000001253 Protein Kinase Human genes 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 108060006633 protein kinase Proteins 0.000 claims 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- WLIZYVKCXBYABW-UHFFFAOYSA-N n-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C1=O)=CNC=C1C(=O)NC(C=C1)=CC=C1OC1=CC=NC2=C1OCCN2 WLIZYVKCXBYABW-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- FRKYTXQYFMZKNZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-oxo-n-[4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=CC(OC=3C=4OCCCNC=4N=CC=3)=CC=2)=CC=C1 FRKYTXQYFMZKNZ-UHFFFAOYSA-N 0.000 claims 1
- OFYUXXBJSFCKRK-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-oxo-n-[4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]thiazepin-9-yloxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=CC(OC=3C=4SCCCNC=4N=CC=3)=CC=2)=CC=C1 OFYUXXBJSFCKRK-UHFFFAOYSA-N 0.000 claims 1
- WPJGHIVGAOVUAT-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-oxopyridine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CC=CN1C1=CC=C(F)C=C1 WPJGHIVGAOVUAT-UHFFFAOYSA-N 0.000 claims 1
- MJGODWYRMWCVJP-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-[3-fluoro-4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4OCCCNC=4N=CC=3)=CC=2)=CC=C1 MJGODWYRMWCVJP-UHFFFAOYSA-N 0.000 claims 1
- BLWZAWOOQCNSGK-UHFFFAOYSA-N 1-n'-(4-fluorophenyl)-1-n-[4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]cyclopropane-1,1-dicarboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(OC=3C=4OCCCNC=4N=CC=3)=CC=2)CC1 BLWZAWOOQCNSGK-UHFFFAOYSA-N 0.000 claims 1
- IRCMORRLEYDMBU-UHFFFAOYSA-N 1-n'-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazin-8-yloxy)-3-fluorophenyl]-1-n-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1(C(=O)NC=2C=C(F)C(OC=3C=4SCCNC=4N=CC=3)=CC=2)CC1 IRCMORRLEYDMBU-UHFFFAOYSA-N 0.000 claims 1
- FDXFNRSUPWPXBJ-UHFFFAOYSA-N 1-n'-[4-[(3,3-dimethyl-2,4-dihydropyrido[3,2-b][1,4]oxazin-8-yl)oxy]-3-fluorophenyl]-1-n-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound N1C(C)(C)COC2=C1N=CC=C2OC(C(=C1)F)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 FDXFNRSUPWPXBJ-UHFFFAOYSA-N 0.000 claims 1
- FWEHYBDHTGWBGW-UHFFFAOYSA-N 1-n'-[4-[(3,3-dimethyl-2,4-dihydropyrido[3,2-b][1,4]thiazin-8-yl)oxy]-3-fluorophenyl]-1-n-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound N1C(C)(C)CSC2=C1N=CC=C2OC(C(=C1)F)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 FWEHYBDHTGWBGW-UHFFFAOYSA-N 0.000 claims 1
- NUWCZFOUMFSSON-UHFFFAOYSA-N 1-n-(4-fluorophenyl)-1-n'-[3-fluoro-4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]cyclopropane-1,1-dicarboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1(C(=O)NC=2C=C(F)C(OC=3C=4OCCCNC=4N=CC=3)=CC=2)CC1 NUWCZFOUMFSSON-UHFFFAOYSA-N 0.000 claims 1
- ZMDHKMBAJZASIH-UHFFFAOYSA-N 1-n-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]thiazin-8-yloxy)phenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(OC=3C=4SCCNC=4N=CC=3)=CC=2)CC1 ZMDHKMBAJZASIH-UHFFFAOYSA-N 0.000 claims 1
- SNFMFGKVRUTWHA-UHFFFAOYSA-N 1-n-[4-[(3,3-dimethyl-2,4-dihydropyrido[3,2-b][1,4]oxazin-8-yl)oxy]phenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound N1C(C)(C)COC2=C1N=CC=C2OC(C=C1)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 SNFMFGKVRUTWHA-UHFFFAOYSA-N 0.000 claims 1
- HDKXDBOMKZRAIA-UHFFFAOYSA-N 1-n-[4-[(3,3-dimethyl-2,4-dihydropyrido[3,2-b][1,4]thiazin-8-yl)oxy]phenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound N1C(C)(C)CSC2=C1N=CC=C2OC(C=C1)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 HDKXDBOMKZRAIA-UHFFFAOYSA-N 0.000 claims 1
- BXAOWYGNLKPHSL-UHFFFAOYSA-N 2-(4-fluoroanilino)-3-methyl-5-[5-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)pyridin-2-yl]pyrimidin-4-one Chemical compound N=1C=C(C=2N=CC(OC=3C=4OCCCNC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=C(F)C=C1 BXAOWYGNLKPHSL-UHFFFAOYSA-N 0.000 claims 1
- JBZTXEHTQXPUHW-UHFFFAOYSA-N 2-(4-fluoroanilino)-3-methyl-5-[5-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]thiazepin-9-yloxy)pyridin-2-yl]pyrimidin-4-one Chemical compound N=1C=C(C=2N=CC(OC=3C=4SCCCNC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=C(F)C=C1 JBZTXEHTQXPUHW-UHFFFAOYSA-N 0.000 claims 1
- WIKUBKNCIIIRKR-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[3-fluoro-4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]-2-oxoimidazolidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)N(C(=O)NC=2C=C(F)C(OC=3C=4OCCCNC=4N=CC=3)=CC=2)CC1 WIKUBKNCIIIRKR-UHFFFAOYSA-N 0.000 claims 1
- IXEGFTIVNVYKIP-UHFFFAOYSA-N 3-fluoro-4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]thiazepin-9-yloxy)aniline Chemical compound FC1=CC(N)=CC=C1OC1=CC=NC2=C1SCCCN2 IXEGFTIVNVYKIP-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- HMLAPEFIMHQHAK-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-oxo-n-[4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C1=O)=CNC=C1C(=O)NC(C=C1)=CC=C1OC1=CC=NC2=C1OCCCN2 HMLAPEFIMHQHAK-UHFFFAOYSA-N 0.000 claims 1
- UKYXBGZGMZUGHG-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-oxo-n-[4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]thiazepin-9-yloxy)phenyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C1=O)=CNC=C1C(=O)NC(C=C1)=CC=C1OC1=CC=NC2=C1SCCCN2 UKYXBGZGMZUGHG-UHFFFAOYSA-N 0.000 claims 1
- IXHHCSPUESIWRD-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-(3-fluoro-4-spiro[3,4-dihydropyrido[3,2-b][1,4]oxazine-2,1'-cyclopropane]-8-yloxyphenyl)-4-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C1=O)=CNC=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1OC1(CC1)CN2 IXHHCSPUESIWRD-UHFFFAOYSA-N 0.000 claims 1
- DZRJUGZZXNPYHY-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[3-fluoro-4-(2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yloxy)phenyl]-4-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C1=O)=CNC=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1OCCCN2 DZRJUGZZXNPYHY-UHFFFAOYSA-N 0.000 claims 1
- DAMCSNDKULLWBA-UHFFFAOYSA-N 5-[5-(2,3-dihydro-1h-pyrrolo[2,3-b]pyridin-4-yloxy)pyridin-2-yl]-2-(4-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2N=CC(OC=3C=4CCNC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=C(F)C=C1 DAMCSNDKULLWBA-UHFFFAOYSA-N 0.000 claims 1
- SIULNZPSBTZEPG-UHFFFAOYSA-N 5-[5-[(3,3-dimethyl-2,4-dihydropyrido[3,2-b][1,4]oxazin-8-yl)oxy]pyridin-2-yl]-2-(4-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2N=CC(OC=3C=4OCC(C)(C)NC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=C(F)C=C1 SIULNZPSBTZEPG-UHFFFAOYSA-N 0.000 claims 1
- RMIXTFLTXNXKKL-UHFFFAOYSA-N 5-[5-[(3,3-dimethyl-2,4-dihydropyrido[3,2-b][1,4]thiazin-8-yl)oxy]pyridin-2-yl]-2-(4-fluoroanilino)-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2N=CC(OC=3C=4SCC(C)(C)NC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=C(F)C=C1 RMIXTFLTXNXKKL-UHFFFAOYSA-N 0.000 claims 1
- VPJGESSPJGADBC-UHFFFAOYSA-N 8-[6-[2-(4-fluoroanilino)-1-methyl-6-oxopyrimidin-5-yl]pyridin-3-yl]oxy-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N=1C=C(C=2N=CC(OC=3C=4OCC(=O)NC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=C(F)C=C1 VPJGESSPJGADBC-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- FEJCAYGIXQVMAV-UHFFFAOYSA-N C1CCSC2=C(N1)N=CC=C2OC1=CC=C(NC(=O)C2(CC2)C(=O)NC2=CC=C(C=C2)F)C=C1 Chemical compound C1CCSC2=C(N1)N=CC=C2OC1=CC=C(NC(=O)C2(CC2)C(=O)NC2=CC=C(C=C2)F)C=C1 FEJCAYGIXQVMAV-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims 1
- XVVIKMMXGANNJO-UHFFFAOYSA-N FC1=CC=C(C=C1)NC(=O)C1(CC1)C(=O)NC1=C(C(=C(C=C1)OC1=C2C(=NC=C1)NC(C2)=O)F)F Chemical compound FC1=CC=C(C=C1)NC(=O)C1(CC1)C(=O)NC1=C(C(=C(C=C1)OC1=C2C(=NC=C1)NC(C2)=O)F)F XVVIKMMXGANNJO-UHFFFAOYSA-N 0.000 claims 1
- UFVBUAQQYIKRRI-UHFFFAOYSA-N Fc1ccc(NC(=O)C2(CC2)C(=O)Nc2ccc(Oc3ccnc4NCCCSc34)c(F)c2)cc1 Chemical compound Fc1ccc(NC(=O)C2(CC2)C(=O)Nc2ccc(Oc3ccnc4NCCCSc34)c(F)c2)cc1 UFVBUAQQYIKRRI-UHFFFAOYSA-N 0.000 claims 1
- VPZMLTLMYLZSOR-UHFFFAOYSA-N Fc1ccc(cc1)-n1cccc(C(=O)Nc2ccc(Oc3ccnc4NCCCSc34)c(F)c2)c1=O Chemical compound Fc1ccc(cc1)-n1cccc(C(=O)Nc2ccc(Oc3ccnc4NCCCSc34)c(F)c2)c1=O VPZMLTLMYLZSOR-UHFFFAOYSA-N 0.000 claims 1
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 claims 1
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 claims 1
- 201000008808 Fibrosarcoma Diseases 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 208000027927 Hereditary papillary renal cell carcinoma Diseases 0.000 claims 1
- 101001106413 Homo sapiens Macrophage-stimulating protein receptor Proteins 0.000 claims 1
- 101000987310 Homo sapiens Serine/threonine-protein kinase PAK 2 Proteins 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 102100021435 Macrophage-stimulating protein receptor Human genes 0.000 claims 1
- 206010025538 Malignant ascites Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims 1
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 102100028448 Nuclear receptor subfamily 2 group C member 2 Human genes 0.000 claims 1
- 208000022873 Ocular disease Diseases 0.000 claims 1
- 101700056750 PAK1 Proteins 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000000582 Retinoblastoma Diseases 0.000 claims 1
- 102000001332 SRC Human genes 0.000 claims 1
- 108060006706 SRC Proteins 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 102100027910 Serine/threonine-protein kinase PAK 1 Human genes 0.000 claims 1
- 102100027939 Serine/threonine-protein kinase PAK 2 Human genes 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- MVXVYAKCVDQRLW-UHFFFAOYSA-N azain Natural products C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 230000009033 hematopoietic malignancy Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000026037 malignant tumor of neck Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- ILSBMPQZYHPAIP-UHFFFAOYSA-N n-[3-fluoro-4-[(2-oxo-1,3-dihydropyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4CC(=O)NC=4N=CC=3)=CC=2)=CC=C1 ILSBMPQZYHPAIP-UHFFFAOYSA-N 0.000 claims 1
- NAQXSTWFIQVVRY-UHFFFAOYSA-N n-[3-fluoro-4-[(2-oxo-1,3-dihydropyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl]-5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C1=O)=CNC=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1CC(=O)N2 NAQXSTWFIQVVRY-UHFFFAOYSA-N 0.000 claims 1
- NAYGCUUHQOSZBR-UHFFFAOYSA-N n-[3-fluoro-4-[(3-oxo-1,2-dihydropyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(=O)CNC=4N=CC=3)=CC=2)=CC=C1 NAYGCUUHQOSZBR-UHFFFAOYSA-N 0.000 claims 1
- RDZFFKZMENKECY-UHFFFAOYSA-N n-[3-fluoro-4-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-8-yl)oxy]phenyl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C=4OCC(=O)NC=4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 RDZFFKZMENKECY-UHFFFAOYSA-N 0.000 claims 1
- KOOWZDQYWTWBHU-UHFFFAOYSA-N n-[3-fluoro-4-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-8-yl)oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4OCC(=O)NC=4N=CC=3)=CC=2)=CC=C1 KOOWZDQYWTWBHU-UHFFFAOYSA-N 0.000 claims 1
- LEHXYZCOHFNEIQ-UHFFFAOYSA-N n-[3-fluoro-4-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-8-yl)oxy]phenyl]-5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C1=O)=CNC=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1OCC(=O)N2 LEHXYZCOHFNEIQ-UHFFFAOYSA-N 0.000 claims 1
- MMYWEXNODBDKCL-UHFFFAOYSA-N n-[3-fluoro-4-[[2-(hydroxymethyl)-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-8-yl]oxy]phenyl]-5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carboxamide Chemical compound C=12OC(CO)CNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CNC=C1C1=CC=C(F)C=C1 MMYWEXNODBDKCL-UHFFFAOYSA-N 0.000 claims 1
- JQEXXZKPEDSLNT-UHFFFAOYSA-N n-[4-(2,3-dihydro-1h-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C=4CCNC=4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 JQEXXZKPEDSLNT-UHFFFAOYSA-N 0.000 claims 1
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| CN106279147A (zh) | 2015-05-21 | 2017-01-04 | 中国科学院上海药物研究所 | 一种吡啶并氮杂环化合物及其制备方法和用途 |
| CA2990752C (en) * | 2015-07-20 | 2020-03-10 | Betta Pharmaceuticals Co., Ltd | Crystalline form of fused pyridine derivative's maleate and uses thereof |
| CN106924260B (zh) * | 2015-12-31 | 2018-05-25 | 北京浦润奥生物科技有限责任公司 | 化合物在制备用于治疗脑胶质瘤的药物中的用途 |
| TWI781920B (zh) | 2016-02-05 | 2022-11-01 | 美商戴納立製藥公司 | 化合物、組合物及方法 |
| PL3552017T3 (pl) | 2016-12-09 | 2022-08-08 | Denali Therapeutics Inc. | Związki użyteczne jako inhibitory RIPK1 |
| KR20200011965A (ko) * | 2017-05-26 | 2020-02-04 | 아이크노스 사이언스 에스. 아. | Map4k1의 신규한 억제제 |
| WO2018233527A1 (zh) * | 2017-06-19 | 2018-12-27 | 上海和誉生物医药科技有限公司 | 一种具有csf1r抑制活性的氮杂芳基衍生物、其制备方法和应用 |
| CN109988108B (zh) * | 2017-12-29 | 2022-04-29 | 江苏豪森药业集团有限公司 | 一种卡博替尼的制备方法 |
| CA3122575A1 (en) * | 2018-12-14 | 2020-06-18 | Beta Pharma, Inc. | Organophosphorus-substituted compounds as c-met inhibitors and therapeutic uses thereof |
| JP2022526713A (ja) | 2019-03-21 | 2022-05-26 | オンクセオ | がんの処置のための、キナーゼ阻害剤と組み合わせたＤｂａｉｔ分子 |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| TWI812302B (zh) * | 2021-06-24 | 2023-08-11 | 南韓商Ｌｇ化學股份有限公司 | 作為ｒｏｎ抑制劑之新穎尿素衍生物化合物 |
| IL314082A (en) | 2022-01-12 | 2024-09-01 | Denali Therapeutics Inc | Crystal forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazapin-3-yl)- H4- 1,2,4-triazole-3-carboxamide |
| EP4289427A1 (en) * | 2022-06-10 | 2023-12-13 | Anagenesis Biotechnologies | Dihydro[1,8]naphthyridin-7-one and pyrido[3,2-b][1,4]oxazin-3-one for use in treating cancer, and metastases in particular. |
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| US20050288290A1 (en) * | 2004-06-28 | 2005-12-29 | Borzilleri Robert M | Fused heterocyclic kinase inhibitors |
| EP1773826A4 (en) * | 2004-07-02 | 2009-06-03 | Exelixis Inc | MODULATORS OF C-MET AND THEIR METHOD OF USE |
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| MX2007006230A (es) | 2004-11-30 | 2007-07-25 | Amgen Inc | Quinolinas y analogos de quinazolinas y su uso como medicamentos para tratar cancer. |
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| WO2008049855A2 (en) * | 2006-10-27 | 2008-05-02 | Glaxo Group Limited | 7-azaindole derivatives as c-met kinase inhibitors |
| US7960567B2 (en) * | 2007-05-02 | 2011-06-14 | Amgen Inc. | Compounds and methods useful for treating asthma and allergic inflammation |
| KR100961410B1 (ko) * | 2008-10-14 | 2010-06-09 | (주)네오팜 | 단백질 키나제 억제제로서 헤테로사이클릭 화합물 |
| US8293897B2 (en) | 2008-10-14 | 2012-10-23 | Ning Xi | Compounds comprising a spiro-ring and methods of use |
| CN102086211B (zh) * | 2009-12-08 | 2013-09-11 | 广东东阳光药业有限公司 | 作为蛋白激酶抑制剂的芳杂环化合物 |
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- 2013-07-01 WO PCT/CN2013/078592 patent/WO2014000713A1/en not_active Ceased
- 2013-07-01 KR KR1020157002238A patent/KR101726522B1/ko not_active Expired - Fee Related
- 2013-07-01 US US14/411,515 patent/US9617257B2/en not_active Expired - Fee Related
- 2013-07-01 ES ES13809182T patent/ES2698511T3/es active Active
- 2013-07-01 KR KR1020177003331A patent/KR101770545B1/ko not_active Expired - Fee Related
-
2015
- 2015-01-16 ZA ZA2015/00344A patent/ZA201500344B/en unknown
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