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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- DGXHQCRALGIMKL-UHFFFAOYSA-N n-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-8-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=4OCCNC=4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 DGXHQCRALGIMKL-UHFFFAOYSA-N 0.000 claims 1
- SDJRRBSJTIGZJT-UHFFFAOYSA-N n-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-8-yloxy)-3-fluorophenyl]-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=4OCCNC=4N=CC=3)=CC=2)=CC=C1 SDJRRBSJTIGZJT-UHFFFAOYSA-N 0.000 claims 1
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- NSPMDZVQNZHIRQ-UHFFFAOYSA-N n-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-8-yloxy)phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=CC(OC=3C=4OCCNC=4N=CC=3)=CC=2)=CC=C1 NSPMDZVQNZHIRQ-UHFFFAOYSA-N 0.000 claims 1
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- PIEFDJQLUMWISX-UHFFFAOYSA-N n-[4-[(3,3-dimethyl-2,4-dihydropyrido[3,2-b][1,4]thiazin-8-yl)oxy]-3-fluorophenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CN=C2NC(C)(C)CSC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1=CC=C(F)C=C1 PIEFDJQLUMWISX-UHFFFAOYSA-N 0.000 claims 1
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- XGDZIDIBULRTBN-UHFFFAOYSA-N n-[4-[(3,4-dimethyl-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-9-yl)oxy]phenyl]-5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CN=C2NC(C)C(C)COC2=C1OC(C=C1)=CC=C1NC(=O)C(C1=O)=CNC=C1C1=CC=C(F)C=C1 XGDZIDIBULRTBN-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 |
| EP3292115B1 (en) * | 2015-07-20 | 2019-12-25 | 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 |
| JP7208137B2 (ja) | 2016-12-09 | 2023-01-18 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| AU2018272986A1 (en) * | 2017-05-26 | 2019-12-12 | Ichnos Sciences SA | Novel inhibitors of MAP4K1 |
| JP7131837B2 (ja) * | 2017-06-19 | 2022-09-06 | アビスコ セラピューティクス カンパニー リミテッド | Ｃｓｆ－１ｒ阻害活性を有するアザアリール誘導体、その製造方法および応用 |
| 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 |
| EA202191541A1 (ru) | 2018-12-14 | 2022-01-21 | Бета Фарма, Инк. | ЗАМЕЩЕННЫЕ ФОСФОРОРГАНИЧЕСКИМИ ГРУППАМИ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ c-MET И ИХ ТЕРАПЕВТИЧЕСКИЕ ПРИМЕНЕНИЯ |
| EA202192575A1 (ru) | 2019-03-21 | 2022-01-14 | Онксео | Соединения dbait в сочетании с ингибиторами киназ для лечения рака |
| CN114761006A (zh) | 2019-11-08 | 2022-07-15 | Inserm(法国国家健康医学研究院) | 对激酶抑制剂产生耐药性的癌症的治疗方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| 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 |
| TW202334164A (zh) | 2022-01-12 | 2023-09-01 | 美商戴納立製藥公司 | （Ｓ）－５－苄基－Ｎ－（５－甲基－４－側氧基－２，３，４，５－四氫吡啶並［３，２－ｂ］［１，４］氧氮呯－３－基）－４Ｈ－１，２，４－三唑－３－甲醯胺的晶型 |
| WO2023205463A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| 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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| DE10357510A1 (de) | 2003-12-09 | 2005-07-07 | Bayer Healthcare Ag | Heteroarylsubstituierte Benzole |
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| 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 |
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| 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 |
| ES2598530T3 (es) * | 2010-07-14 | 2017-01-27 | Betta Pharmaceuticals Co., Ltd. | Nuevos derivados heterocíclicos condensados útiles como inhibidores de la tirosina quinasa c-Met |
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- 2013-07-01 BR BR112014032745-9A patent/BR112014032745B1/pt not_active IP Right Cessation
- 2013-07-01 KR KR1020177003335A patent/KR101726555B1/ko not_active Expired - Fee Related
- 2013-07-01 US US14/411,515 patent/US9617257B2/en not_active Expired - Fee Related
- 2013-07-01 SG SG11201408750VA patent/SG11201408750VA/en unknown
- 2013-07-01 JP JP2015518816A patent/JP6059342B2/ja not_active Expired - Fee Related
- 2013-07-01 KR KR1020177003331A patent/KR101770545B1/ko not_active Expired - Fee Related
- 2013-07-01 AU AU2013283993A patent/AU2013283993B2/en not_active Ceased
- 2013-07-01 EP EP13809182.2A patent/EP2867223B1/en not_active Not-in-force
- 2013-07-01 CA CA2878049A patent/CA2878049C/en not_active Expired - Fee Related
- 2013-07-01 KR KR1020157002238A patent/KR101726522B1/ko not_active Expired - Fee Related
- 2013-07-01 IN IN372DEN2015 patent/IN2015DN00372A/en unknown
- 2013-07-01 ES ES13809182T patent/ES2698511T3/es active Active
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2015
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