JP2009539878A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009539878A5 JP2009539878A5 JP2009514553A JP2009514553A JP2009539878A5 JP 2009539878 A5 JP2009539878 A5 JP 2009539878A5 JP 2009514553 A JP2009514553 A JP 2009514553A JP 2009514553 A JP2009514553 A JP 2009514553A JP 2009539878 A5 JP2009539878 A5 JP 2009539878A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorophenyl
- yloxy
- compound
- methoxyquinolin
- morpholinopropoxy
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 160
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 32
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 25
- 201000011510 cancer Diseases 0.000 claims description 24
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 22
- -1 CF 3 Inorganic materials 0.000 claims description 22
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 102000027426 receptor tyrosine kinases Human genes 0.000 claims description 8
- 108091008598 receptor tyrosine kinases Proteins 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 210000004027 cell Anatomy 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000003325 follicular Effects 0.000 claims description 4
- 208000019423 liver disease Diseases 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 206010038038 rectal cancer Diseases 0.000 claims description 4
- 201000001275 rectum cancer Diseases 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
- 108091000080 Phosphotransferase Proteins 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 102000020233 phosphotransferase Human genes 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- CZASFNOAAISAFF-UHFFFAOYSA-N (3-benzylpiperidin-1-yl)-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]methanone Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(=O)N(C1)CCCC1CC1=CC=CC=C1 CZASFNOAAISAFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- HCRKLKXMWARSLU-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-oxopyrrolidine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)CCN1C1=CC=C(Cl)C=C1 HCRKLKXMWARSLU-UHFFFAOYSA-N 0.000 claims description 2
- CYGULOBIQBPIGA-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=CN1CC1=CC=C(Cl)C=C1 CYGULOBIQBPIGA-UHFFFAOYSA-N 0.000 claims description 2
- XTFQSZBXKIHRDT-UHFFFAOYSA-N 1-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-n-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(F)C=C1 XTFQSZBXKIHRDT-UHFFFAOYSA-N 0.000 claims description 2
- KJEFGVAWXWIQGJ-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-methylpyridin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N1C=CC=C(C)C1=O KJEFGVAWXWIQGJ-UHFFFAOYSA-N 0.000 claims description 2
- JMAYKJICPAKRCH-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-[hydroxy(phenyl)methyl]pyridin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C=1)=O)C=CC=1C(O)C1=CC=CC=C1 JMAYKJICPAKRCH-UHFFFAOYSA-N 0.000 claims description 2
- ADIWWIQZOINKMR-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-methylpyridin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N1C=CC(C)=CC1=O ADIWWIQZOINKMR-UHFFFAOYSA-N 0.000 claims description 2
- MHBZLDBZYDWYCR-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C1=O)CCC1C(=O)NC1=CC=C(F)C=C1 MHBZLDBZYDWYCR-UHFFFAOYSA-N 0.000 claims description 2
- RQPYZXRJMUCYPX-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyridin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N1C=CC=CC1=O RQPYZXRJMUCYPX-UHFFFAOYSA-N 0.000 claims description 2
- FPYJSJDOHRDAMT-KQWNVCNZSA-N 1h-indole-5-sulfonamide, n-(3-chlorophenyl)-3-[[3,5-dimethyl-4-[(4-methyl-1-piperazinyl)carbonyl]-1h-pyrrol-2-yl]methylene]-2,3-dihydro-n-methyl-2-oxo-, (3z)- Chemical compound C=1C=C2NC(=O)\C(=C/C3=C(C(C(=O)N4CCN(C)CC4)=C(C)N3)C)C2=CC=1S(=O)(=O)N(C)C1=CC=CC(Cl)=C1 FPYJSJDOHRDAMT-KQWNVCNZSA-N 0.000 claims description 2
- ONSZEUCTVQJHOZ-UHFFFAOYSA-N 2-(4-fluoroanilino)-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=C(F)C=C1 ONSZEUCTVQJHOZ-UHFFFAOYSA-N 0.000 claims description 2
- UHGFZGZPWQKINB-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[6-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxypyridin-3-yl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(N=C1)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 UHGFZGZPWQKINB-UHFFFAOYSA-N 0.000 claims description 2
- JSVZOHYGPLLJPX-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NCC1CC1 JSVZOHYGPLLJPX-UHFFFAOYSA-N 0.000 claims description 2
- SWEWZOSVNQXGKK-UHFFFAOYSA-N 2-anilino-3-ethyl-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound N=1C=C(C=2C=C(F)C(OC=3C4=CC(OC)=C(OCCCN5CCOCC5)C=C4N=CC=3)=CC=2)C(=O)N(CC)C=1NC1=CC=CC=C1 SWEWZOSVNQXGKK-UHFFFAOYSA-N 0.000 claims description 2
- PZNFSAHEDPJDOW-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC=C1 PZNFSAHEDPJDOW-UHFFFAOYSA-N 0.000 claims description 2
- HBVGKCFCLCCZDQ-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1h-pyrimidin-6-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CN=C1CC1=CC=CC=C1 HBVGKCFCLCCZDQ-UHFFFAOYSA-N 0.000 claims description 2
- PEGWVOKOYYAQEV-UHFFFAOYSA-N 2-benzyl-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1CC1=CC=CC=C1 PEGWVOKOYYAQEV-UHFFFAOYSA-N 0.000 claims description 2
- VFNQFMVWZBQRKK-UHFFFAOYSA-N 2-benzyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1h-pyrimidin-6-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CN=C1CC1=CC=CC=C1 VFNQFMVWZBQRKK-UHFFFAOYSA-N 0.000 claims description 2
- DSMDOGYKOPDKOX-UHFFFAOYSA-N 2-benzyl-5-[4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1h-pyrimidin-6-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C=C1)=CC=C1C(C(N1)=O)=CN=C1CC1=CC=CC=C1 DSMDOGYKOPDKOX-UHFFFAOYSA-N 0.000 claims description 2
- WIAJXGOOHAMRNL-UHFFFAOYSA-N 3-[(2-chloro-4-fluorophenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(F)C=C1Cl WIAJXGOOHAMRNL-UHFFFAOYSA-N 0.000 claims description 2
- SSUDTNPNRVALDO-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1Cl SSUDTNPNRVALDO-UHFFFAOYSA-N 0.000 claims description 2
- OHFBRQZLZHLFOT-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(Cl)C(Cl)=C1 OHFBRQZLZHLFOT-UHFFFAOYSA-N 0.000 claims description 2
- NIYRASPRJQHADV-UHFFFAOYSA-N 3-[(3-chlorophenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC(Cl)=C1 NIYRASPRJQHADV-UHFFFAOYSA-N 0.000 claims description 2
- OMEHVQACOVBTKY-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=C(F)C=C(Cl)C=C1F OMEHVQACOVBTKY-UHFFFAOYSA-N 0.000 claims description 2
- XHTPDKSQIVWVJV-UHFFFAOYSA-N 3-[(4-chloro-2-fluorophenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(Cl)C=C1F XHTPDKSQIVWVJV-UHFFFAOYSA-N 0.000 claims description 2
- AHFGGVDVZLDQFO-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(Cl)C=C1 AHFGGVDVZLDQFO-UHFFFAOYSA-N 0.000 claims description 2
- XEEXWDAEUSWRDH-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(Cl)C=C1 XEEXWDAEUSWRDH-UHFFFAOYSA-N 0.000 claims description 2
- OIYYEFSPBRIBAB-UHFFFAOYSA-N 3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1,4-dihydroquinazolin-2-one Chemical compound COC1=CC2=C(OC=3C(=CC(=CC=3)N3C(NC4=CC=CC=C4C3)=O)F)C=CN=C2C=C1OCCCN1CCOCC1 OIYYEFSPBRIBAB-UHFFFAOYSA-N 0.000 claims description 2
- SUOYTGLWULKFLG-UHFFFAOYSA-N 3-benzyl-5-[3-fluoro-4-(6-methoxy-7-phenylmethoxyquinolin-4-yl)oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1 SUOYTGLWULKFLG-UHFFFAOYSA-N 0.000 claims description 2
- OAKJLQCLZAHWDW-UHFFFAOYSA-N 3-benzyl-5-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1 OAKJLQCLZAHWDW-UHFFFAOYSA-N 0.000 claims description 2
- WYVPHOWSUCMAJZ-UHFFFAOYSA-N 3-benzyl-5-[3-fluoro-4-[6-methoxy-7-(3-piperidin-1-ylpropoxy)quinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCCCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1 WYVPHOWSUCMAJZ-UHFFFAOYSA-N 0.000 claims description 2
- HMRDKMRYUZQYFL-UHFFFAOYSA-N 3-benzyl-5-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCN(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1 HMRDKMRYUZQYFL-UHFFFAOYSA-N 0.000 claims description 2
- JQTSPNODCQKRBY-UHFFFAOYSA-N 3-benzyl-5-[3-fluoro-4-[7-(2-imidazol-1-ylethoxy)-6-methoxyquinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCN3C=NC=C3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1 JQTSPNODCQKRBY-UHFFFAOYSA-N 0.000 claims description 2
- LOFSBYQEEBKELK-UHFFFAOYSA-N 3-benzyl-5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1 LOFSBYQEEBKELK-UHFFFAOYSA-N 0.000 claims description 2
- WTKWFWVTYYNDDZ-UHFFFAOYSA-N 4-[2-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(oxan-2-yl)phenol Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=C(F)C=CC=C1C(C=1)=CC=C(O)C=1C1CCCCO1 WTKWFWVTYYNDDZ-UHFFFAOYSA-N 0.000 claims description 2
- KFUWSASFLWYOSO-UHFFFAOYSA-N 4-[2-fluoro-4-(6-methoxypyridin-3-yl)phenoxy]-6,7-dimethoxyquinoline Chemical compound C1=NC(OC)=CC=C1C(C=C1F)=CC=C1OC1=CC=NC2=CC(OC)=C(OC)C=C12 KFUWSASFLWYOSO-UHFFFAOYSA-N 0.000 claims description 2
- HVWUFVPCTVVPBW-UHFFFAOYSA-N 4-[2-fluoro-6-(4-phenoxyphenyl)phenoxy]-6,7-dimethoxyquinoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=C(F)C=CC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 HVWUFVPCTVVPBW-UHFFFAOYSA-N 0.000 claims description 2
- XDRKJNTVIONAQS-UHFFFAOYSA-N 4-[2-fluoro-6-(4-phenylcyclohexyl)phenoxy]-6,7-dimethoxyquinoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=C(F)C=CC=C1C(CC1)CCC1C1=CC=CC=C1 XDRKJNTVIONAQS-UHFFFAOYSA-N 0.000 claims description 2
- KHXYJPIGHWZRJK-UHFFFAOYSA-N 4-[2-fluoro-6-[4-(pyrazol-1-ylmethyl)phenyl]phenoxy]-6,7-dimethoxyquinoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=C(F)C=CC=C1C(C=C1)=CC=C1CN1C=CC=N1 KHXYJPIGHWZRJK-UHFFFAOYSA-N 0.000 claims description 2
- XZGSOEUIBWAOHG-UHFFFAOYSA-N 4-benzyl-1-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyridin-2-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C(C=1)=O)C=CC=1CC1=CC=CC=C1 XZGSOEUIBWAOHG-UHFFFAOYSA-N 0.000 claims description 2
- QYFRXIOGHJCRDC-UHFFFAOYSA-N 4-benzyl-1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyridin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C(C=1)=O)C=CC=1CC1=CC=CC=C1 QYFRXIOGHJCRDC-UHFFFAOYSA-N 0.000 claims description 2
- GAIFLZOYTCJOKX-UHFFFAOYSA-N 4-benzyl-n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-3-oxopyrazine-2-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=NC=CN1CC1=CC=CC=C1 GAIFLZOYTCJOKX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- FNKYSCPBPBAQKC-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1h-pyrimidin-6-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C1=CN=CNC1=O FNKYSCPBPBAQKC-UHFFFAOYSA-N 0.000 claims description 2
- KGCXXXJFCUOBCJ-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-(4-methylphenyl)pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1C1=CC=C(C)C=C1 KGCXXXJFCUOBCJ-UHFFFAOYSA-N 0.000 claims description 2
- FABFOMANLISXOH-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-[(2-fluorophenyl)methyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1F FABFOMANLISXOH-UHFFFAOYSA-N 0.000 claims description 2
- GQGZLMWFSWQUSB-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-[(2-methylphenyl)methyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=CC=C1C GQGZLMWFSWQUSB-UHFFFAOYSA-N 0.000 claims description 2
- RXVILNBWCFSJHM-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-[(3,4-dimethylphenyl)methyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(C)C(C)=C1 RXVILNBWCFSJHM-UHFFFAOYSA-N 0.000 claims description 2
- HGNAGFAYDXZUKZ-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-[(4-fluoro-3-methylphenyl)methyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(F)C(C)=C1 HGNAGFAYDXZUKZ-UHFFFAOYSA-N 0.000 claims description 2
- OPICNXDVTAGULD-UHFFFAOYSA-N 5-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-[(4-fluorophenyl)methyl]pyrimidin-4-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(F)C=C1 OPICNXDVTAGULD-UHFFFAOYSA-N 0.000 claims description 2
- FKZHXXSGIVQLFH-UHFFFAOYSA-N 5-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C1=O)C=NC=C1CC1=CC=CC=C1 FKZHXXSGIVQLFH-UHFFFAOYSA-N 0.000 claims description 2
- OXLDQWRSQJFLLB-UHFFFAOYSA-N 6-anilino-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-5-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C(C=1C)=O)C=NC=1NC1=CC=CC=C1 OXLDQWRSQJFLLB-UHFFFAOYSA-N 0.000 claims description 2
- TXFJFEGBPNYKCD-UHFFFAOYSA-N 6-anilino-3-[4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-5-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C=C1)=CC=C1N(C(C=1C)=O)C=NC=1NC1=CC=CC=C1 TXFJFEGBPNYKCD-UHFFFAOYSA-N 0.000 claims description 2
- HWYMJQTVCQPGCU-UHFFFAOYSA-N 6-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-methylpyridin-2-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CC=C1CC1=CC=CC=C1 HWYMJQTVCQPGCU-UHFFFAOYSA-N 0.000 claims description 2
- WRPWIMUEGZEMOX-UHFFFAOYSA-N 6-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1h-pyridin-2-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CC=C1CC1=CC=CC=C1 WRPWIMUEGZEMOX-UHFFFAOYSA-N 0.000 claims description 2
- GHYGFSSYSKEQMS-UHFFFAOYSA-N 6-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-5-methylpyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C(C=1C)=O)C=NC=1CC1=CC=CC=C1 GHYGFSSYSKEQMS-UHFFFAOYSA-N 0.000 claims description 2
- VSPIZALLIAPEJL-UHFFFAOYSA-N 6-benzyl-3-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyrimidin-4-one Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1N(C(C=1)=O)C=NC=1CC1=CC=CC=C1 VSPIZALLIAPEJL-UHFFFAOYSA-N 0.000 claims description 2
- VSBAUAFNMWVXNV-UHFFFAOYSA-N 6-benzyl-3-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1h-pyridin-2-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1)=O)=CC=C1CC1=CC=CC=C1 VSBAUAFNMWVXNV-UHFFFAOYSA-N 0.000 claims description 2
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 2
- 208000003200 Adenoma Diseases 0.000 claims description 2
- 206010001233 Adenoma benign Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 206010004593 Bile duct cancer Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- SNPGEEISPQMFEA-UHFFFAOYSA-N C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=C(F)C=CC=C1C1=CC=C(CNS(=O)=O)C=C1 Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=C(F)C=CC=C1C1=CC=C(CNS(=O)=O)C=C1 SNPGEEISPQMFEA-UHFFFAOYSA-N 0.000 claims description 2
- XNZWJXOIOUABIV-UHFFFAOYSA-N CN(C1=CC=CC=C1)C2=NC=CC(=N2)C3=CC(=C(C=C3)OC4=C5C=C(C(=CC5=NC=C4)OC)OC)F Chemical compound CN(C1=CC=CC=C1)C2=NC=CC(=N2)C3=CC(=C(C=C3)OC4=C5C=C(C(=CC5=NC=C4)OC)OC)F XNZWJXOIOUABIV-UHFFFAOYSA-N 0.000 claims description 2
- ZWBFHBHNGUGSRE-UHFFFAOYSA-N COC1=CC2=C(C=CN=C2C=C1OC)OC3=C(C=C(C=C3)C4=NC(=NC=C4)NC5=CC=CC=C5)F Chemical compound COC1=CC2=C(C=CN=C2C=C1OC)OC3=C(C=C(C=C3)C4=NC(=NC=C4)NC5=CC=CC=C5)F ZWBFHBHNGUGSRE-UHFFFAOYSA-N 0.000 claims description 2
- XGFVAUCTSYTFSJ-UHFFFAOYSA-N COC1=CC2=C(C=CN=C2C=C1OC)OC3=C(C=C(C=C3)C4=NC=CC(=O)N4)F Chemical compound COC1=CC2=C(C=CN=C2C=C1OC)OC3=C(C=C(C=C3)C4=NC=CC(=O)N4)F XGFVAUCTSYTFSJ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010023825 Laryngeal cancer Diseases 0.000 claims description 2
- 206010062038 Lip neoplasm Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 208000018501 Lymphatic disease Diseases 0.000 claims description 2
- 208000003445 Mouth Neoplasms Diseases 0.000 claims description 2
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims description 2
- 206010034811 Pharyngeal cancer Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 201000010208 Seminoma Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 206010042674 Swelling Diseases 0.000 claims description 2
- 230000006044 T cell activation Effects 0.000 claims description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
- 206010057644 Testis cancer Diseases 0.000 claims description 2
- 108090000190 Thrombin Proteins 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 206010062129 Tongue neoplasm Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 208000009956 adenocarcinoma Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000000172 allergic effect Effects 0.000 claims description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 2
- 230000001028 anti-proliverative effect Effects 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 208000026900 bile duct neoplasm Diseases 0.000 claims description 2
- 208000015322 bone marrow disease Diseases 0.000 claims description 2
- 201000000220 brain stem cancer Diseases 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 230000030833 cell death Effects 0.000 claims description 2
- 201000007455 central nervous system cancer Diseases 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 230000001066 destructive effect Effects 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 230000004761 fibrosis Effects 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 210000004907 gland Anatomy 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 230000036039 immunity Effects 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 208000033065 inborn errors of immunity Diseases 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 206010023841 laryngeal neoplasm Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims description 2
- 201000006721 lip cancer Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000018555 lymphatic system disease Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 239000002207 metabolite Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 210000000214 mouth Anatomy 0.000 claims description 2
- DQYAMJDQWMHIMX-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopiperidine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)CCCN1C1=CC=C(F)C=C1 DQYAMJDQWMHIMX-UHFFFAOYSA-N 0.000 claims description 2
- HNWWSQPXMVKXCT-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1=CC=C(F)C=C1 HNWWSQPXMVKXCT-UHFFFAOYSA-N 0.000 claims description 2
- AGWBKSBACINZRU-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)CCN1C1=CC=C(F)C=C1 AGWBKSBACINZRU-UHFFFAOYSA-N 0.000 claims description 2
- LLVYBPBLTZCFIS-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-[(4-fluorophenyl)methyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=CN1CC1=CC=C(F)C=C1 LLVYBPBLTZCFIS-UHFFFAOYSA-N 0.000 claims description 2
- IAZHLFVCLYVTPC-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C1=CC=CN(C)C1=O IAZHLFVCLYVTPC-UHFFFAOYSA-N 0.000 claims description 2
- YNEKPXJXBUFCSK-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-1-methyl-2-oxopyrrolidine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C1CCN(C)C1=O YNEKPXJXBUFCSK-UHFFFAOYSA-N 0.000 claims description 2
- OSIQBRLXIPYVLY-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 OSIQBRLXIPYVLY-UHFFFAOYSA-N 0.000 claims description 2
- IHWKZYKDKFYPKM-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-oxo-1-phenylpyrrolidine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)CCN1C1=CC=CC=C1 IHWKZYKDKFYPKM-UHFFFAOYSA-N 0.000 claims description 2
- GOSSBQJGVSSIHU-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-oxopyrrolidine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C1CCNC1=O GOSSBQJGVSSIHU-UHFFFAOYSA-N 0.000 claims description 2
- PFOIOOANQJSCFA-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-pyridin-2-ylacetamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)CC1=CC=CC=N1 PFOIOOANQJSCFA-UHFFFAOYSA-N 0.000 claims description 2
- SLJPPDQJRFXTKR-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-7,7-dimethyl-3-oxobicyclo[2.2.1]heptane-4-carboxamide Chemical compound COC1=CC2=C(OC=3C(=CC(NC(=O)C45C(CC(CC4)C5(C)C)=O)=CC=3)F)C=CN=C2C=C1OCCCN1CCOCC1 SLJPPDQJRFXTKR-UHFFFAOYSA-N 0.000 claims description 2
- FXPSMAZXOKEQJV-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC1=CC=CC=N1 FXPSMAZXOKEQJV-UHFFFAOYSA-N 0.000 claims description 2
- BEFIXWRSQXVAQL-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]quinoline-8-carboxamide Chemical compound COC1=CC2=C(OC=3C(=CC(NC(=O)C=4C5=NC=CC=C5C=CC=4)=CC=3)F)C=CN=C2C=C1OCCCN1CCOCC1 BEFIXWRSQXVAQL-UHFFFAOYSA-N 0.000 claims description 2
- WCOUURYBEARRLP-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-piperidin-1-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCCCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 WCOUURYBEARRLP-UHFFFAOYSA-N 0.000 claims description 2
- VPPQNYLVSPEKIT-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCN(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 VPPQNYLVSPEKIT-UHFFFAOYSA-N 0.000 claims description 2
- LFDZBJYNOLKRGH-UHFFFAOYSA-N n-[6-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxynaphthalen-2-yl]thiophene-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C=C1C=C2)=CC=C1C=C2NC(=O)C=1C=CSC=1 LFDZBJYNOLKRGH-UHFFFAOYSA-N 0.000 claims description 2
- XFDFEDVYZMEERX-UHFFFAOYSA-N n-cyclopropyl-4-[2-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]benzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC1=C(F)C=CC=C1C(C=C1)=CC=C1C(=O)NC1CC1 XFDFEDVYZMEERX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims description 2
- 235000005152 nicotinamide Nutrition 0.000 claims description 2
- 239000011570 nicotinamide Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 210000003800 pharynx Anatomy 0.000 claims description 2
- 208000028529 primary immunodeficiency disease Diseases 0.000 claims description 2
- 230000002062 proliferating effect Effects 0.000 claims description 2
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 208000000649 small cell carcinoma Diseases 0.000 claims description 2
- 201000002314 small intestine cancer Diseases 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 230000008961 swelling Effects 0.000 claims description 2
- YLUNTOOQILQUMA-UHFFFAOYSA-N tert-butyl 2-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]pyrrole-1-carboxylate Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C1=CC=CN1C(=O)OC(C)(C)C YLUNTOOQILQUMA-UHFFFAOYSA-N 0.000 claims description 2
- 201000003120 testicular cancer Diseases 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 229960004072 thrombin Drugs 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 201000006134 tongue cancer Diseases 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- XTRGSQYPIIPHIN-UHFFFAOYSA-N (4-benzylpiperidin-1-yl)-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]methanone Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(=O)N(CC1)CCC1CC1=CC=CC=C1 XTRGSQYPIIPHIN-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 CC1COC(*)CC1 Chemical compound CC1COC(*)CC1 0.000 description 54
- 230000003463 hyperproliferative effect Effects 0.000 description 2
- JPCFJIYAQBNBJK-UHFFFAOYSA-N (3-benzylpiperidin-1-yl)-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]methanone Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(=O)N(C1)CCCC1CC1=CC=CC=C1 JPCFJIYAQBNBJK-UHFFFAOYSA-N 0.000 description 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- CUPJLJCFEAVNLP-UHFFFAOYSA-N 4-benzylpiperidine-1-carbaldehyde Chemical compound C1CN(C=O)CCC1CC1=CC=CC=C1 CUPJLJCFEAVNLP-UHFFFAOYSA-N 0.000 description 1
- XFGCKLRUCQKWSV-UHFFFAOYSA-N CC#CCN(CC1)CCC1(C(F)(F)F)O Chemical compound CC#CCN(CC1)CCC1(C(F)(F)F)O XFGCKLRUCQKWSV-UHFFFAOYSA-N 0.000 description 1
- GKWBNHDYBUJCAB-UHFFFAOYSA-N CC(C)COC(N1CCC(CC(NC)=O)CC1)=O Chemical compound CC(C)COC(N1CCC(CC(NC)=O)CC1)=O GKWBNHDYBUJCAB-UHFFFAOYSA-N 0.000 description 1
- NOOVOUXRFFKSQQ-UHFFFAOYSA-N CC(C)N(c1cc(F)ccc1CN1)C1=O Chemical compound CC(C)N(c1cc(F)ccc1CN1)C1=O NOOVOUXRFFKSQQ-UHFFFAOYSA-N 0.000 description 1
- YRKRGYRYEQYTOH-UHFFFAOYSA-N CC(C1)CNC1=O Chemical compound CC(C1)CNC1=O YRKRGYRYEQYTOH-UHFFFAOYSA-N 0.000 description 1
- LPQKWTYFSZDQDD-UHFFFAOYSA-M CC(C1=O)=CC=C(Cc2cc(CC3CC3)ccc2)N1[Re] Chemical compound CC(C1=O)=CC=C(Cc2cc(CC3CC3)ccc2)N1[Re] LPQKWTYFSZDQDD-UHFFFAOYSA-M 0.000 description 1
- NSRPFJGOCZUUHE-UHFFFAOYSA-N CC(CC1)CNC1=O Chemical compound CC(CC1)CNC1=O NSRPFJGOCZUUHE-UHFFFAOYSA-N 0.000 description 1
- APOJIILNJVLCQE-UHFFFAOYSA-N CC1OC(C)CN(C)C1 Chemical compound CC1OC(C)CN(C)C1 APOJIILNJVLCQE-UHFFFAOYSA-N 0.000 description 1
- ZXPAWABQQHKFNJ-UHFFFAOYSA-N CCN(CC)CCC#CC Chemical compound CCN(CC)CCC#CC ZXPAWABQQHKFNJ-UHFFFAOYSA-N 0.000 description 1
- QRYWRVHZEBEZDQ-UHFFFAOYSA-N CN(CC1)CCN1C(c1ccccc1)=O Chemical compound CN(CC1)CCN1C(c1ccccc1)=O QRYWRVHZEBEZDQ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N CN(CCC1)C1=O Chemical compound CN(CCC1)C1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- COYPZADTXISTSJ-UHFFFAOYSA-N CN(CCCN1)C1=O Chemical compound CN(CCCN1)C1=O COYPZADTXISTSJ-UHFFFAOYSA-N 0.000 description 1
- GSXMSFLLOUQAKR-UHFFFAOYSA-N CN(Cc(cccc1)c1N1C)C1=O Chemical compound CN(Cc(cccc1)c1N1C)C1=O GSXMSFLLOUQAKR-UHFFFAOYSA-N 0.000 description 1
- GINUUQLRYXHAPB-UHFFFAOYSA-N CN(Cc1ccccc1N1)C1=O Chemical compound CN(Cc1ccccc1N1)C1=O GINUUQLRYXHAPB-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N CN1CCN(C)CC1 Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- MLJOKPBESJWYGL-UHFFFAOYSA-N CN1CCN(Cc2ccccc2)CC1 Chemical compound CN1CCN(Cc2ccccc2)CC1 MLJOKPBESJWYGL-UHFFFAOYSA-N 0.000 description 1
- AXKMXHRZYFOELW-UHFFFAOYSA-N CNC(C1=CC=CN(c2ccccc2)C1=O)=O Chemical compound CNC(C1=CC=CN(c2ccccc2)C1=O)=O AXKMXHRZYFOELW-UHFFFAOYSA-N 0.000 description 1
- SIXSDXBPHBHLPS-UHFFFAOYSA-N CNC(CCOC)=O Chemical compound CNC(CCOC)=O SIXSDXBPHBHLPS-UHFFFAOYSA-N 0.000 description 1
- DMACFPYXNNQAOG-UHFFFAOYSA-N CNC(CN(C)C(c1ccccc1)=O)=O Chemical compound CNC(CN(C)C(c1ccccc1)=O)=O DMACFPYXNNQAOG-UHFFFAOYSA-N 0.000 description 1
- UKXDZOZWBDCBGL-UHFFFAOYSA-N CNC(c1cccc2cccnc12)=O Chemical compound CNC(c1cccc2cccnc12)=O UKXDZOZWBDCBGL-UHFFFAOYSA-N 0.000 description 1
- FFNMISPCRNMWFK-UHFFFAOYSA-N O=C(C1=CC=NN(c2ccccc2)C1=O)N[IH]I Chemical compound O=C(C1=CC=NN(c2ccccc2)C1=O)N[IH]I FFNMISPCRNMWFK-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81190906P | 2006-06-08 | 2006-06-08 | |
| PCT/US2007/070787 WO2007146824A2 (en) | 2006-06-08 | 2007-06-08 | Quinoline compounds and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009539878A JP2009539878A (ja) | 2009-11-19 |
| JP2009539878A5 true JP2009539878A5 (https=) | 2011-07-21 |
Family
ID=38658188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009514553A Pending JP2009539878A (ja) | 2006-06-08 | 2007-06-08 | キノリン化合物および使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110053931A1 (https=) |
| EP (1) | EP2032538A2 (https=) |
| JP (1) | JP2009539878A (https=) |
| CN (1) | CN101528702A (https=) |
| CA (1) | CA2655128A1 (https=) |
| WO (1) | WO2007146824A2 (https=) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8778977B2 (en) | 2006-06-30 | 2014-07-15 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl PDK1 inhibitors |
| US7776857B2 (en) * | 2007-04-05 | 2010-08-17 | Amgen Inc. | Aurora kinase modulators and method of use |
| BRPI0816064B8 (pt) | 2007-08-29 | 2021-05-25 | Methylgene Inc | composto inibidor da atividade de proteína tirosina quinase, seu uso, e composição farmacêutica |
| RU2601892C2 (ru) * | 2008-03-06 | 2016-11-10 | Дженентек, Инк. | Комбинированная терапия антагонистами с-мет и egfr |
| EP2262772B8 (en) * | 2008-04-16 | 2013-03-13 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Quinoline derivatives as axl kinase inhibitors |
| US8389500B2 (en) | 2008-10-30 | 2013-03-05 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| FR2940289B1 (fr) * | 2008-12-23 | 2014-09-12 | Biopharmed | Derives de la classe des hydroxyquinoleines aminees pour le traitement du cancer du pancreas |
| EP2563773A1 (en) | 2010-04-29 | 2013-03-06 | Deciphera Pharmaceuticals, LLC | Pyridone amides and analogs exhibiting anti-cancer and anti-proliferative activites |
| WO2012011548A1 (ja) * | 2010-07-23 | 2012-01-26 | 国立大学法人 東京大学 | 含窒素複素環誘導体 |
| EP2423208A1 (en) * | 2010-08-28 | 2012-02-29 | Lead Discovery Center GmbH | Pharmaceutically active compounds as Axl inhibitors |
| US20140080810A1 (en) | 2010-11-15 | 2014-03-20 | Exelixis, Inc. | Benzoxazepines as Inhibitors of PI3K/mTOR and Methods of Their Use and Manufacture |
| CN102558147B (zh) * | 2010-12-23 | 2014-09-17 | 江苏先声药物研究有限公司 | 化合物、制备方法及应用 |
| WO2012118632A1 (en) | 2011-02-28 | 2012-09-07 | Ning Xi | Substituted quinoline compounds and methods of use |
| EP2780338B1 (en) * | 2011-11-14 | 2016-11-09 | Ignyta, Inc. | Uracil derivatives as axl and c-met kinase inhibitors |
| CN102643268B (zh) * | 2011-12-30 | 2014-05-21 | 沈阳药科大学 | 喹啉类及噌啉类化合物及其应用 |
| WO2013177367A2 (en) | 2012-05-23 | 2013-11-28 | The Johns Hopkins University | Compounds and methods of use thereof for treating neurodegenerative disorders |
| SI2864291T1 (sl) | 2012-06-26 | 2017-01-31 | Bayer Pharma Aktiengesellschaft | N-(4-(kinolin-4-iloksi)cikloheksil(metil))(hetero)arilkarboksamidi kot antagonisti receptorja androgena, njihova izdelava in uporaba kot medicinski izdelki |
| CN103965107B (zh) * | 2013-02-06 | 2016-08-17 | 沈阳药科大学 | 2-芳基取代喹啉类化合物及其用途 |
| JP6669499B2 (ja) | 2013-02-15 | 2020-03-18 | カラ ファーマシューティカルズ インコーポレイテッド | 治療用化合物 |
| JP2016510000A (ja) | 2013-02-20 | 2016-04-04 | カラ ファーマシューティカルズ インコーポレイテッド | 治療用化合物およびその使用 |
| US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
| CN104072480B (zh) * | 2013-03-27 | 2016-12-28 | 沈阳药科大学 | 喹啉类化合物及其制备方法和应用 |
| SMT201700513T1 (it) * | 2013-05-01 | 2018-01-11 | Celgene Corp | Sintesi di 3-(5-ammino-2-metil-4-ossochinazolin-3(4h)-il) piperidin-2,6-dione |
| JP6464395B2 (ja) * | 2013-06-06 | 2019-02-06 | リード ディスカヴァリー センター ゲーエムベーハーＬｅａｄ Ｄｉｓｃｏｖｅｒｙ Ｃｅｎｔｅｒ ＧｍｂＨ | マクロファージを刺激する１受容体ｍｓｔｒ１のキノリン阻害剤 |
| TWI649308B (zh) | 2013-07-24 | 2019-02-01 | 小野藥品工業股份有限公司 | 喹啉衍生物 |
| US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| NZ719185A (en) | 2013-11-01 | 2017-11-24 | Kala Pharmaceuticals Inc | Crystalline forms of therapeutic compounds and uses thereof |
| CN103739596A (zh) * | 2013-12-10 | 2014-04-23 | 刘磊 | 用于心脑血管疾病的喹唑啉衍生物 |
| EP3122900A1 (en) | 2014-03-24 | 2017-02-01 | F. Hoffmann-La Roche AG | Cancer treatment with c-met antagonists and correlation of the latter with hgf expression |
| CN104086529B (zh) * | 2014-05-18 | 2015-12-30 | 马宝花 | 一种喹唑啉类衍生物、其制备方法及其用途 |
| WO2016104617A1 (ja) * | 2014-12-25 | 2016-06-30 | 小野薬品工業株式会社 | キノリン誘導体 |
| CN104817497B (zh) * | 2015-03-20 | 2017-03-08 | 南京众睿缘生物科技有限公司 | 一种炔代喹啉衍生物及其制备方法和用途 |
| CN104926789A (zh) * | 2015-05-20 | 2015-09-23 | 沈阳药科大学 | 含咪唑酮的4-苯氧基取代喹啉类化合物及其应用 |
| US10550135B2 (en) | 2016-03-30 | 2020-02-04 | Council Of Scientific & Industrial Research | Silicon incorporated quinolines with anti-malarial and anti-toxoplasmosis activity |
| CN107474039B (zh) * | 2016-06-08 | 2020-05-01 | 沈阳药科大学 | 含三氮唑酮和咪唑的4-苯氧基取代喹啉类化合物及其应用 |
| KR20190051010A (ko) | 2016-09-08 | 2019-05-14 | 칼라 파마슈티컬스, 인크. | 치료 화합물의 결정형 및 그의 용도 |
| EP3509423A4 (en) | 2016-09-08 | 2020-05-13 | Kala Pharmaceuticals, Inc. | CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF |
| AU2017324713B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| CA3045224A1 (en) | 2016-12-16 | 2018-06-21 | Basf Se | Pesticidal compounds |
| EP3575293B1 (en) | 2017-01-26 | 2021-03-10 | ONO Pharmaceutical Co., Ltd. | Ethanesulfonate salt of n-{5-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-pyridinyl}-2,5-dioxo-1-phenyl-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide |
| CN110506038B (zh) | 2017-03-28 | 2023-11-24 | 巴斯夫欧洲公司 | 杀害虫化合物 |
| EP3695839A4 (en) | 2017-10-13 | 2021-07-14 | ONO Pharmaceutical Co., Ltd. | THERAPEUTIC AGENT WITH AXL INHIBITOR AS AN ACTIVE INGREDIENT FOR SOLID TUMORS |
| CA3086083A1 (en) | 2017-12-21 | 2019-06-27 | Basf Se | Pesticidal compounds |
| WO2019124548A1 (ja) | 2017-12-22 | 2019-06-27 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除剤 |
| CN108299292B (zh) * | 2018-02-13 | 2021-03-26 | 安徽工业大学 | 5,7-二溴-8-(甲氧甲氧基)-2-甲基喹啉或其药用盐在治疗乳腺癌中的应用 |
| CN110483482A (zh) | 2018-05-15 | 2019-11-22 | 北京诺诚健华医药科技有限公司 | 吲哚啉-1-甲酰胺类化合物、其制备方法及其在医药学上的应用 |
| CA3101983A1 (en) * | 2018-06-01 | 2019-12-05 | Rigel Pharmaceuticals, Inc. | Quinoline derivatives useful as tyrosine kinase inhibitors |
| CN108707145B (zh) * | 2018-07-05 | 2021-02-26 | 沈阳药科大学 | 含五元杂环结构的喹啉类化合物及其制备和应用 |
| WO2020027723A1 (en) * | 2018-08-01 | 2020-02-06 | Agency For Science, Technology And Research | Bicyclic compounds as kinase modulators, methods and uses thereof |
| KR20210066820A (ko) * | 2018-08-27 | 2021-06-07 | 베이징 위에즈캉타이 바이오메디슨스 컴퍼니, 리미티드 | 다중-치환된 피리돈 유도체 및 이의 의학적 용도 |
| US20220033363A1 (en) | 2018-09-19 | 2022-02-03 | Bayer Aktiengesellschaft | Herbicidally active substituted phenylpyrimidine hydrazides |
| EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
| CN111303024B (zh) * | 2018-12-12 | 2023-03-28 | 安徽中科拓苒药物科学研究有限公司 | 一种喹啉结构的pan-KIT激酶抑制剂及其用途 |
| CR20210364A (es) * | 2019-01-03 | 2021-08-18 | Array Biopharma Inc | Compuestos de quinolina como inhibidores de quinasas tam y met |
| AU2020210863B2 (en) * | 2019-01-25 | 2025-10-23 | Exelixis, Inc. | Compounds for the treatment of kinase-dependent disorders |
| EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
| EP4011885A4 (en) * | 2019-08-02 | 2023-01-18 | Wellmarker Bio Co., Ltd. | CONDENSED CYCLE OXO-PYRIDINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING THEM |
| JP2022551422A (ja) | 2019-09-26 | 2022-12-09 | エグゼリクシス， インコーポレイテッド | ピリドン化合物およびタンパク質キナーゼの調節における使用の方法 |
| IL313548A (en) | 2021-12-16 | 2024-08-01 | Kinnate Biopharma Inc | MET kinase inhibitors |
| CN117362275A (zh) * | 2022-06-29 | 2024-01-09 | 广州百霆医药科技有限公司 | 一种酪氨酸蛋白激酶抑制剂及其用途 |
| CN117343046A (zh) * | 2023-09-25 | 2024-01-05 | 辽宁大学 | 一种新型3-氧代-4-取代芳基-3,4-二氢吡嗪-2-甲酰胺类化合物及其应用 |
| WO2026024165A1 (ko) * | 2024-07-22 | 2026-01-29 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
| CN120289432B (zh) * | 2025-06-12 | 2025-09-05 | 上海健康医学院 | 一种具有极光激酶b和表皮生长因子受体双重抑制作用的喹啉类化合物及用途 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US20030162795A1 (en) * | 1998-10-22 | 2003-08-28 | Pfizer Inc. | Thienopyrimidine and thienopyridine derivatives useful as anticancer agents |
| GB9906566D0 (en) * | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
| US6297238B1 (en) * | 1999-04-06 | 2001-10-02 | Basf Aktiengesellschaft | Therapeutic agents |
| US20020004511A1 (en) * | 2000-06-28 | 2002-01-10 | Luzzio Michael Joseph | Thiophene derivatives useful as anticancer agents |
| AU2002303892A1 (en) * | 2001-05-30 | 2002-12-09 | Jingrong Cui | 5-aralkylsulfonyl-3- (pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors |
| AU2002345792A1 (en) * | 2001-06-21 | 2003-01-08 | Pfizer Inc. | Thienopyridine and thienopyrimidine anticancer agents |
| EP2258366B1 (en) * | 2001-06-22 | 2013-04-03 | Kirin Pharma Kabushiki Kaisha | Quinoline derivatives capable of inhibiting autophosphorylation of hepatocyte growth factor receptors, and pharmaceutical composition comprising the same |
| EP1447405A4 (en) * | 2001-10-17 | 2005-01-12 | Kirin Brewery | CHINOLIN OR CHINAZOLINE DERIVATIVES THAT PREVENT THE AUTOPHOSPHORYLATION OF RECEPTORS FOR THE FIBROBLAST GROWTH FACTOR |
| BR0308162A (pt) * | 2002-03-01 | 2004-12-07 | Pfizer | Derivados de indolil-uréia de tienopiridinas úteis como agentes antiangiogênicos e métodos para o seu uso |
| US6790852B2 (en) * | 2002-04-18 | 2004-09-14 | Hoffmann-La Roche Inc. | 2-(2,6-dichlorophenyl)-diarylimidazoles |
| EP1548008A4 (en) * | 2002-08-23 | 2008-08-06 | Kirin Pharma Kk | COMPOUND WITH TGF-BETA-HEMMENDER EFFECT AND THIS MEDICAL COMPOSITION CONTAINING |
| AU2003272740A1 (en) * | 2002-10-01 | 2004-04-23 | Johnson & Johnson Pharmaceutical Research & Development, L.L.C. | 4,6-diaminosubstituted-2-[oxy or aminoxy]-[1,3,5]triazines as protein tyrosine kinase inhibitors |
| US7276519B2 (en) * | 2002-11-25 | 2007-10-02 | Wyeth | Thieno[3,2-b]pyridine-6-carbonitriles and thieno[2,3-b]pyridine-5-carbonitriles as protein kinase inhibitors |
| CL2003002287A1 (es) * | 2002-11-25 | 2005-01-14 | Wyeth Corp | COMPUESTOS DERIVADOS DE TIENO[3,2-b]-PIRIDINA-6-CARBONITRILOS Y TIENEO[2,3-b]-PIRIDINA-5-CARBONITRILOS, COMPOSICION FARMACEUTICA, PROCEDIMIENTO DE PREPARACION Y COMPUESTOS INTERMEDIARIOS, Y SU USO EN EL TRATAMIENTO DEL CANCER, APOPLEJIA, OSTEOPOROSIS |
| WO2004072117A2 (en) * | 2003-02-13 | 2004-08-26 | Pharmacia Corporation | Antibodies to c-met for the treatment of cancers |
| CA2517256C (en) * | 2003-02-26 | 2013-04-30 | Sugen, Inc. | Aminoheteroaryl compounds as protein kinase inhibitors |
| WO2004092154A1 (en) * | 2003-04-03 | 2004-10-28 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| MXPA05013181A (es) * | 2003-06-06 | 2006-06-23 | Genentech Inc | Metodos y composiciones para modular hgf/met. |
| US7122548B2 (en) * | 2003-07-02 | 2006-10-17 | Sugen, Inc. | Triazolotriazine compounds and uses thereof |
| EP1644362A2 (en) * | 2003-07-02 | 2006-04-12 | Sugen, Inc. | Indolinone hydrazides as c-met inhibitors |
| CA2536470A1 (en) * | 2003-08-15 | 2005-02-24 | Vertex Pharmaceuticals Incorporated | Pyrrole compositions useful as inhibitors of c-met |
| EP1660504B1 (en) * | 2003-08-29 | 2008-10-29 | Pfizer Inc. | Thienopyridine-phenylacet amides and their derivatives useful as new anti-angiogenic agents |
| EP1660503A1 (en) * | 2003-08-29 | 2006-05-31 | Pfizer Inc. | Naphthalene carboxamides and their derivatives useful as new anti-angiogenic agents |
| AU2004284420A1 (en) * | 2003-09-24 | 2005-05-06 | Vertex Pharmaceuticals Incorporated | 4-azole substituted imidazole compositions useful as inhibitors or c-Met receptor tyrosine kinase |
| PT2213661E (pt) * | 2003-09-26 | 2011-12-15 | Exelixis Inc | Moduladores de c-met e métodos de uso |
| JP4932495B2 (ja) * | 2004-01-23 | 2012-05-16 | アムゲン インコーポレイテッド | 化合物及び使用方法 |
| WO2005073224A2 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc | Quinoline quinazoline pyridine and pyrimidine counds and their use in the treatment of inflammation angiogenesis and cancer |
| WO2005080377A1 (ja) * | 2004-02-20 | 2005-09-01 | Kirin Beer Kabushiki Kaisha | TGFβ阻害活性を有する化合物およびそれを含んでなる医薬組成物 |
| US7459562B2 (en) * | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| TW200538453A (en) * | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| EP1751136B1 (en) * | 2004-05-07 | 2014-07-02 | Amgen Inc. | Nitrogenated heterocyclic derivatives as protein kinase modulators and use for the treatment of angiogenesis and cancer |
| EP1753428A4 (en) * | 2004-05-14 | 2010-09-15 | Abbott Lab | INHIBITORS OF KINASES AS THERAPEUTIC AGENTS |
| EP1781293A1 (en) * | 2004-06-04 | 2007-05-09 | Amphora Discovery Corporation | Quinoline- and isoquinoline-based compounds exhibiting atp-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| US7173031B2 (en) * | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7439246B2 (en) * | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| CA2572331A1 (en) * | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | C-met modulators and method of use |
| KR101257343B1 (ko) * | 2004-07-30 | 2013-04-23 | 메틸진 인코포레이티드 | Ｖｅｇｆ 수용체 및 ｈｇｆ 수용체 신호전달 억제제 |
| MX2007006230A (es) * | 2004-11-30 | 2007-07-25 | Amgen Inc | Quinolinas y analogos de quinazolinas y su uso como medicamentos para tratar cancer. |
| AU2006229343A1 (en) * | 2005-03-28 | 2006-10-05 | Kirin Pharma Kabushiki Kaisha | Thienopyridine derivative, or quinoline derivative, or quinazoline derivative, having c-Met autophosphorylation inhibiting potency |
| US20080161305A1 (en) * | 2005-04-06 | 2008-07-03 | Exelixis, Inc. | C-Met Modulators and Methods of Use |
| US7470693B2 (en) * | 2005-04-21 | 2008-12-30 | Bristol-Myers Squibb Company | Oxalamide derivatives as kinase inhibitors |
| JO2787B1 (en) * | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| GB0509227D0 (en) * | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Intracellular enzyme inhibitors |
| CN101796055B (zh) * | 2005-05-20 | 2013-09-04 | 梅特希尔基因公司 | Vegf受体和hgf受体信号的抑制剂 |
| AU2006313456B2 (en) * | 2005-05-20 | 2011-06-23 | Methylgene Inc. | Inhibitors of VEGF receptor and HGF receptor signaling |
| US7732613B2 (en) * | 2005-09-14 | 2010-06-08 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| WO2007035428A1 (en) * | 2005-09-15 | 2007-03-29 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| US7547782B2 (en) * | 2005-09-30 | 2009-06-16 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| JP2009526761A (ja) * | 2006-01-30 | 2009-07-23 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環式チオフェン化合物および使用の方法 |
| BRPI0708615A2 (pt) * | 2006-03-07 | 2011-06-07 | Array Biopharma Inc | compostos de pirazol heterobicìclicos e métodos de uso |
| DK2124944T3 (da) * | 2007-03-14 | 2012-04-23 | Ranbaxy Lab Ltd | Pyrazolo[3,4-b]pyridinderivater som phosphodiesteraseinhibitorer |
| CN101918403A (zh) * | 2007-09-06 | 2010-12-15 | 阵列生物制药公司 | 作为酪氨酸激酶抑制剂的吡唑并吡啶类化合物 |
| RU2495878C2 (ru) * | 2007-12-21 | 2013-10-20 | Ф.Хоффманн-Ля Рош Аг | Гетероциклические антивирусные соединения |
-
2007
- 2007-06-08 JP JP2009514553A patent/JP2009539878A/ja active Pending
- 2007-06-08 EP EP07798333A patent/EP2032538A2/en not_active Withdrawn
- 2007-06-08 US US12/303,930 patent/US20110053931A1/en not_active Abandoned
- 2007-06-08 CA CA002655128A patent/CA2655128A1/en not_active Abandoned
- 2007-06-08 WO PCT/US2007/070787 patent/WO2007146824A2/en not_active Ceased
- 2007-06-08 CN CNA2007800294412A patent/CN101528702A/zh active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009539878A5 (https=) | ||
| JP6507157B2 (ja) | Ｒｈｏキナーゼ阻害剤 | |
| JP6993985B2 (ja) | イソキノリン－３イル－カルボキサミドならびにその調製および使用の方法 | |
| JP6873145B2 (ja) | ５−置換２−（モルホリン−４−イル）−１，７−ナフチリジン | |
| JP5550352B2 (ja) | 有機化合物およびその使用 | |
| US8003662B2 (en) | Heterobicyclic thiophene compounds and methods of use | |
| JP6342393B2 (ja) | 置換型ピラゾロン化合物及び使用方法 | |
| JP5726515B2 (ja) | Ｐｉ３ｋ−アルファのキナゾリン阻害剤を用いた阻害による治療方法 | |
| CN112204027A (zh) | Erk 抑制剂及其应用 | |
| JP6200520B2 (ja) | 置換２−アミノピリジンプロテインキナーゼ阻害剤 | |
| JP5606434B2 (ja) | ピリジノピリジノン誘導体、この調製およびこの治療用途 | |
| US20110053931A1 (en) | Quinoline compounds and methods of use | |
| CN101356159A (zh) | 经取代异喹啉-1,3(2h,4h)-二酮类、1-硫代-1,4-二氢-2h-异喹啉-3-酮类和1,4-二氢-3(2h)-异喹啉酮类以及其作为激酶抑制剂的用途 | |
| CN100404528C (zh) | 新的嘧啶胺衍生物及其用途 | |
| JP2013525476A (ja) | Ａｌｋ阻害剤としての複素環式誘導体 | |
| JP2019206577A (ja) | 一過性受容体電位ａ１イオンチャネルの阻害 | |
| KR20130129244A (ko) | 치환된 6,6-융합된 질소 헤테로환형 화합물 및 이의 용도 | |
| JP2017508763A5 (https=) | ||
| CA2774099A1 (en) | 6-amino quinazoline or 3-cyano quinoline derivatives, preparation methods and pharmaceutical uses thereof | |
| US20110130406A1 (en) | Pyrazolo-pyridines as tyrosine kinase inhibitors | |
| JP2001508800A (ja) | 血管形成阻害活性を有するフタラジン | |
| JP2019503385A5 (https=) | ||
| CN113773308A (zh) | Rho激酶抑制剂 | |
| CN103420986A (zh) | 取代的喹啉化合物及其使用方法和用途 | |
| KR20060037404A (ko) | 급성 및/또는 만성 신경학적 장애의 치료를 위한ｍＧｌｕＲ2 길항제 및 ＡＣｈＥ 억제제의 조합물 |