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 |
| AU2016297395B2 (en) * | 2015-07-20 | 2019-01-17 | 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 |
| IL287136B2 (en) | 2016-02-05 | 2023-09-01 | Denali Therapeutics Inc | Receptor inhibitors - interacting with protein kinase 1 |
| HUE058802T2 (hu) | 2016-12-09 | 2022-09-28 | Denali Therapeutics Inc | RIPK1 inhibitorokként alkalmas vegyületek |
| AU2018272986A1 (en) * | 2017-05-26 | 2019-12-12 | Ichnos Sciences SA | Novel inhibitors of MAP4K1 |
| 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 |
| SG11202105872RA (en) * | 2018-12-14 | 2021-07-29 | Beta Pharma Inc | Organophosphorus-substituted compounds as c-met inhibitors and therapeutic uses thereof |
| BR112021018168B1 (pt) | 2019-03-21 | 2023-11-28 | Onxeo | Composição farmacêutica, combinação e kit compreendendo uma molécula dbait e um inibidor de quinase para o tratamento de câncer |
| CA3159348A1 (en) | 2019-11-08 | 2021-05-14 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
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| TWI812301B (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 |
| US11999750B2 (en) | 2022-01-12 | 2024-06-04 | Denali Therapeutics Inc. | Crystalline forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydropyrido [3,2-B][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide |
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| JP5368701B2 (ja) * | 2004-07-02 | 2013-12-18 | エクセリクシス、インコーポレイテッド | ｃ−Ｍｅｔモジュレーター及び使用方法 |
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| JP2008521900A (ja) * | 2004-11-30 | 2008-06-26 | アムジエン・インコーポレーテツド | キノリン及びキナゾリン類似体並びにがん治療のための医薬としてのその使用 |
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| US7960567B2 (en) * | 2007-05-02 | 2011-06-14 | Amgen Inc. | Compounds and methods useful for treating asthma and allergic inflammation |
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| AU2009303602B2 (en) | 2008-10-14 | 2012-06-14 | Sunshine Lake Pharma Co., Ltd. | Compounds 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 |
| CA2805148C (en) * | 2010-07-14 | 2016-01-19 | Zhejiang Beta Pharma Inc. | Novel fused heterocyclic derivatives useful as c-met tyrosine kinase inhibitors |
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- 2013-07-01 WO PCT/CN2013/078592 patent/WO2014000713A1/en not_active Ceased
- 2013-07-01 RU RU2015102057A patent/RU2619130C2/ru active
- 2013-07-01 KR KR1020177003335A patent/KR101726555B1/ko not_active Expired - Fee Related
- 2013-07-01 EP EP13809182.2A patent/EP2867223B1/en not_active Not-in-force
- 2013-07-01 IN IN372DEN2015 patent/IN2015DN00372A/en unknown
- 2013-07-01 ES ES13809182T patent/ES2698511T3/es active Active
-
2015
- 2015-01-16 ZA ZA2015/00344A patent/ZA201500344B/en unknown
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