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 |
|---|---|---|---|---|
| EP2038272B8 (en) | 2006-06-30 | 2013-10-23 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl pdk1 inhibitors |
| US7776857B2 (en) * | 2007-04-05 | 2010-08-17 | Amgen Inc. | Aurora kinase modulators and method of use |
| PL2183254T3 (pl) | 2007-08-29 | 2017-10-31 | Methylgene Inc | Inhibitory aktywności białkowej kinazy tyrozynowej |
| KR20100135780A (ko) * | 2008-03-06 | 2010-12-27 | 제넨테크, 인크. | Ｃ-ｍｅｔ 및 ｅｇｆｒ 길항제로의 조합 요법 |
| RU2010146474A (ru) * | 2008-04-16 | 2012-05-27 | Макс-Планк-Гезелльшафт Цур Фердерунг Дер Виссеншафтен Е.Ф. (De) | Производные хинолина в качестве ингибиторов axl киназ |
| 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 |
| CA2800998A1 (en) | 2010-04-29 | 2011-11-10 | Deciphera Pharmaceuticals, Llc | Pyridone amides and analogs exhibiting anti-cancer and anti-proliferative activities |
| JP5525612B2 (ja) * | 2010-07-23 | 2014-06-18 | 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 |
| RU2568258C2 (ru) | 2011-02-28 | 2015-11-20 | Саншайн Лейк Фарма Ко., Лтд | Замещенные соединения хинолина и способы их использования |
| SG11201402004YA (en) * | 2011-11-14 | 2014-05-29 | Cephalon 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 |
| HUE032306T2 (en) | 2012-06-26 | 2017-09-28 | Bayer Pharma AG | N- [4- (quinolin-4-yloxy) cyclohexyl (methyl)] (hetero) arylcarboxamides as androgen receptor antagonists, their production and use as pharmaceutical products |
| 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 |
| EP2956138B1 (en) | 2013-02-15 | 2022-06-22 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
| MX368903B (es) | 2013-02-20 | 2019-10-21 | Kala Pharmaceuticals Inc | Compuestos terapéuticos y sus usos en el tratamiento de enfermedades proliferativas. |
| 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 |
| EP3003315B1 (en) * | 2013-06-06 | 2018-01-17 | Lead Discovery Center GmbH | A quinoline inhibitor of the macrophage stimulating 1 receptor mst1r |
| 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 |
| US9458169B2 (en) | 2013-11-01 | 2016-10-04 | 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 |
| RU2016141385A (ru) | 2014-03-24 | 2018-04-28 | Дженентек, Инк. | Лечение рака антагонистами с-мет и их корреляция с экспрессией hgf |
| 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 |
| ES2749726T3 (es) * | 2014-12-25 | 2020-03-23 | Ono Pharmaceutical Co | Derivado de quinolina |
| 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 |
| 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 |
| US10336767B2 (en) | 2016-09-08 | 2019-07-02 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| EP3555050A1 (en) | 2016-12-16 | 2019-10-23 | Basf Se | Pesticidal compounds |
| TWI779007B (zh) | 2017-01-26 | 2022-10-01 | 日商小野藥品工業股份有限公司 | 喹啉衍生物的乙磺酸鹽 |
| WO2018177781A1 (en) | 2017-03-28 | 2018-10-04 | Basf Se | Pesticidal compounds |
| US11826363B2 (en) | 2017-10-13 | 2023-11-28 | Ono Pharmaceutical Co., Ltd. | Therapeutic agent for solid cancers, which comprises Axl inhibitor as active ingredient |
| ES3039587T3 (en) | 2017-12-21 | 2025-10-22 | Basf Se | Pesticidal compounds |
| JP7253498B2 (ja) | 2017-12-22 | 2023-04-06 | 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 |
| CA3114987A1 (en) * | 2018-08-27 | 2020-03-05 | Beijing Yuezhikangtai Biomedicines Co., Ltd. | Multi-substituted pyridone derivatives and medical use thereof |
| CN112955443A (zh) | 2018-09-19 | 2021-06-11 | 拜耳公司 | 具有除草活性的取代的苯基嘧啶酰肼 |
| 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 |
| CA3125559A1 (en) * | 2019-01-03 | 2020-07-09 | Array Biopharma Inc. | Quinoline compounds as inhibitors of tam and met kinases |
| BR112021014504A2 (pt) * | 2019-01-25 | 2021-09-28 | Exelixis, Inc. | Compostos para o tratamento de transtornos dependentes de cinase |
| EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
| US20220235064A1 (en) * | 2019-08-02 | 2022-07-28 | Wellmarker Bio Co., Ltd. | Oxo-pyridine fusion ring derivative and pharmaceutical composition comprising same |
| 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 |
| WO2023114809A1 (en) | 2021-12-16 | 2023-06-22 | Kinnate Biopharma Inc. | Inhibitors of met kinase |
| 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 |
| KR20260014483A (ko) * | 2024-07-22 | 2026-01-30 | 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 |
| US6599902B2 (en) * | 2001-05-30 | 2003-07-29 | Sugen, Inc. | 5-aralkysufonyl-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors |
| WO2003000194A2 (en) * | 2001-06-21 | 2003-01-03 | Pfizer Inc. | Thienopyridine and thienopyrimidine anticancer agents |
| AU2002313249B2 (en) * | 2001-06-22 | 2008-08-21 | Kirin Pharma Kabushiki Kaisha | Quinoline derivative and quinazoline derivate inhibiting self-phosphorylation of hepatocytus proliferator receptor, and medicinal composition containing 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 |
| AU2003206068A1 (en) * | 2002-03-01 | 2003-09-16 | Pfizer Inc. | Indolyl-urea derivatives of thienopyridines useful as anti-angiogenic agents |
| US6790852B2 (en) * | 2002-04-18 | 2004-09-14 | Hoffmann-La Roche Inc. | 2-(2,6-dichlorophenyl)-diarylimidazoles |
| WO2004018430A1 (ja) * | 2002-08-23 | 2004-03-04 | 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 |
| 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 |
| BRPI0407446A (pt) * | 2003-02-13 | 2006-01-31 | Pharmacia Corp | Anticorpos para c-met para o tratamento de cânceres |
| DK1603570T5 (da) * | 2003-02-26 | 2013-12-09 | Sugen Inc | Aminoheteroarylforbindelser som proteinkinaseinhibitorer |
| AU2004230841A1 (en) * | 2003-04-03 | 2004-10-28 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| WO2005001486A1 (en) * | 2003-06-06 | 2005-01-06 | Genentech, Inc. | Modulating the interaction between hgf beta chain and c-met |
| MXPA06000276A (es) * | 2003-07-02 | 2006-04-07 | Sugen Inc | Indolinona hidrazidas como inhibidores de c-met. |
| US7122548B2 (en) * | 2003-07-02 | 2006-10-17 | Sugen, Inc. | Triazolotriazine compounds and uses thereof |
| CA2536470A1 (en) * | 2003-08-15 | 2005-02-24 | Vertex Pharmaceuticals Incorporated | Pyrrole compositions useful as inhibitors of c-met |
| ES2314444T3 (es) * | 2003-08-29 | 2009-03-16 | Pfizer Inc. | Tienopiridina-fenilacetaminasy sus derivados utiles como nuevos agentes antiangiogenicos. |
| MXPA06002256A (es) * | 2003-08-29 | 2006-05-17 | Pfizer | Naftaleno carboxamidas y sus derivados utiles como agentes anti-angiogenicos. |
| 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 |
| EP2210607B1 (en) * | 2003-09-26 | 2011-08-17 | Exelixis Inc. | N-[3-fluoro-4-({6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy]quinolin-4-yl}oxy)phenyl]-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide for the treatment of cancer |
| JP2007518823A (ja) * | 2004-01-23 | 2007-07-12 | アムゲン インコーポレイテッド | キノリン、キナゾリン、ピリジン、及びピリミジン化合物と炎症、血管新生、及び癌に対する治療におけるそれら化合物の用途 |
| GEP20084439B (en) * | 2004-01-23 | 2008-07-25 | Amgen Inc | Nitrogen-containing heterocyclic derivatives and pharmaceutical use thereof |
| 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 |
| CA2564355C (en) * | 2004-05-07 | 2012-07-03 | Amgen Inc. | Protein kinase modulators and method of use |
| WO2005110410A2 (en) * | 2004-05-14 | 2005-11-24 | Abbott Laboratories | Kinase inhibitors as therapeutic agents |
| JP2008501696A (ja) * | 2004-06-04 | 2008-01-24 | アンフォラ ディスカバリー コーポレーション | Ａｔｐ利用酵素阻害活性を示すキノリンおよびイソキノリン系化合物、ならびにその組成物および使用 |
| 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 |
| US7977345B2 (en) * | 2004-07-02 | 2011-07-12 | Exelixis, Inc. | c-MET modulators and method of use |
| ES2438017T3 (es) * | 2004-07-30 | 2014-01-15 | Methylgene Inc. | Inhibidores de la señalización del receptor del VEGF y del receptor del HGF |
| 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 |
| 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 |
| EP1874759A4 (en) * | 2005-04-06 | 2009-07-15 | Exelixis Inc | C-MET MODULATORS 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 |
| AU2006313456B2 (en) * | 2005-05-20 | 2011-06-23 | Methylgene Inc. | Inhibitors of VEGF receptor and HGF receptor signaling |
| KR101378716B1 (ko) * | 2005-05-20 | 2014-04-10 | 메틸진 인코포레이티드 | Ｖｅｇｆ 수용체 및 ｈｇｆ 수용체 신호전달의 억제제 |
| WO2007033196A1 (en) * | 2005-09-14 | 2007-03-22 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| US7880004B2 (en) * | 2005-09-15 | 2011-02-01 | 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 |
| WO2007103308A2 (en) * | 2006-03-07 | 2007-09-13 | Array Biopharma Inc. | Heterobicyclic pyrazole compounds and methods of use |
| NZ579645A (en) * | 2007-03-14 | 2012-01-12 | Ranbaxy Lab Ltd | Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors |
| 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 |
| WO2009080534A1 (en) * | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
-
2007
- 2007-06-08 JP JP2009514553A patent/JP2009539878A/ja active Pending
- 2007-06-08 WO PCT/US2007/070787 patent/WO2007146824A2/en not_active Ceased
- 2007-06-08 CA CA002655128A patent/CA2655128A1/en not_active Abandoned
- 2007-06-08 CN CNA2007800294412A patent/CN101528702A/zh 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
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=) | ||
| TW201718597A (zh) | Ｈｐｋ１抑制劑及其使用方法 | |
| 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 |