JP2011517689A5 - - Google Patents
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- Publication number
- JP2011517689A5 JP2011517689A5 JP2011504377A JP2011504377A JP2011517689A5 JP 2011517689 A5 JP2011517689 A5 JP 2011517689A5 JP 2011504377 A JP2011504377 A JP 2011504377A JP 2011504377 A JP2011504377 A JP 2011504377A JP 2011517689 A5 JP2011517689 A5 JP 2011517689A5
- Authority
- JP
- Japan
- Prior art keywords
- quinolin
- yloxy
- phenyl
- fluoro
- dimethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 benzyloxy, 3-amino-propoxy, 2-morpholin-4-yl-ethoxy Chemical group 0.000 claims 97
- 150000001875 compounds Chemical class 0.000 claims 50
- 125000003545 alkoxy group Chemical group 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 229920006395 saturated elastomer Polymers 0.000 claims 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 18
- 125000002837 carbocyclic group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 102100037236 Tyrosine-protein kinase receptor UFO Human genes 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 8
- 108010023337 axl receptor tyrosine kinase Proteins 0.000 claims 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- WTDADORKTIJRBS-UHFFFAOYSA-N 2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyaniline Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC1=CC=C(N)C(F)=C1 WTDADORKTIJRBS-UHFFFAOYSA-N 0.000 claims 2
- YUKHYYXEIQDERD-UHFFFAOYSA-N 3-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyaniline Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC1=CC=C(N)C=C1F YUKHYYXEIQDERD-UHFFFAOYSA-N 0.000 claims 2
- YMRDVTUVQPOINJ-UHFFFAOYSA-N 3-fluoro-4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxyaniline Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC1=CC=C(N)C=C1F YMRDVTUVQPOINJ-UHFFFAOYSA-N 0.000 claims 2
- VMTGCLXWYWVYDP-UHFFFAOYSA-N 3-fluoro-4-[6-methoxy-7-[3-(3-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyaniline Chemical compound C1=CN=C2C=C(OCCCN3CC(C)CCC3)C(OC)=CC2=C1OC1=CC=C(N)C=C1F VMTGCLXWYWVYDP-UHFFFAOYSA-N 0.000 claims 2
- ALVSUJMWEGYAMO-UHFFFAOYSA-N 3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyaniline Chemical compound C1=CN=C2C=C(OCCCN3CCC(C)CC3)C(OC)=CC2=C1OC1=CC=C(N)C=C1F ALVSUJMWEGYAMO-UHFFFAOYSA-N 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- MSMJBOUNAYEPJI-UHFFFAOYSA-N 1-ethyl-n-[4-(6-fluoro-2-methylquinolin-4-yl)oxyphenyl]pyrazole-4-sulfonamide Chemical compound C1=NN(CC)C=C1S(=O)(=O)NC(C=C1)=CC=C1OC1=CC(C)=NC2=CC=C(F)C=C12 MSMJBOUNAYEPJI-UHFFFAOYSA-N 0.000 claims 1
- MXYDTADNYFNAIW-UHFFFAOYSA-N 2,4-difluoro-n-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCC(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1F MXYDTADNYFNAIW-UHFFFAOYSA-N 0.000 claims 1
- YRTICDVPIASUNT-UHFFFAOYSA-N 2,4-difluoro-n-[4-(6-fluoro-2-methylquinolin-4-yl)oxyphenyl]benzenesulfonamide Chemical compound C=12C=C(F)C=CC2=NC(C)=CC=1OC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1F YRTICDVPIASUNT-UHFFFAOYSA-N 0.000 claims 1
- ZZDSJMUFFQHCEX-UHFFFAOYSA-N 2,5-dichloro-n-[2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl ZZDSJMUFFQHCEX-UHFFFAOYSA-N 0.000 claims 1
- MOJCIWPLMWZVOV-UHFFFAOYSA-N 2,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl MOJCIWPLMWZVOV-UHFFFAOYSA-N 0.000 claims 1
- CJOFJPASTXFTLE-UHFFFAOYSA-N 2,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]thiophene-3-sulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C=1C=C(Cl)SC=1Cl CJOFJPASTXFTLE-UHFFFAOYSA-N 0.000 claims 1
- NZXVODBZGVHCAH-UHFFFAOYSA-N 2,5-difluoro-n-[2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(F)=CC=C1F NZXVODBZGVHCAH-UHFFFAOYSA-N 0.000 claims 1
- VQQZZEYBDRJYEI-UHFFFAOYSA-N 2,5-difluoro-n-[3-fluoro-4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC(F)=CC=C1F VQQZZEYBDRJYEI-UHFFFAOYSA-N 0.000 claims 1
- BVXYJKJBFXAJDL-UHFFFAOYSA-N 2,5-difluoro-n-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCC(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC(F)=CC=C1F BVXYJKJBFXAJDL-UHFFFAOYSA-N 0.000 claims 1
- WUCDQDOVCASWFO-UHFFFAOYSA-N 2,5-difluoro-n-[4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxy-2-methylphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C=C1C)=CC=C1NS(=O)(=O)C1=CC(F)=CC=C1F WUCDQDOVCASWFO-UHFFFAOYSA-N 0.000 claims 1
- XUELXGWVUNLLLM-UHFFFAOYSA-N 2,6-dichloro-n-[2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=C(Cl)C=CC=C1Cl XUELXGWVUNLLLM-UHFFFAOYSA-N 0.000 claims 1
- HYLPAUGDDLRNBK-UHFFFAOYSA-N 2,6-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=C(Cl)C=CC=C1Cl HYLPAUGDDLRNBK-UHFFFAOYSA-N 0.000 claims 1
- GWHIQZJLMHMXPW-UHFFFAOYSA-N 2,6-difluoro-n-[3-fluoro-4-[6-methoxy-7-[3-(3-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CC(C)CCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=C(F)C=CC=C1F GWHIQZJLMHMXPW-UHFFFAOYSA-N 0.000 claims 1
- FULDQQPIMXRKEN-UHFFFAOYSA-N 2-bromo-n-[3-fluoro-4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1Br FULDQQPIMXRKEN-UHFFFAOYSA-N 0.000 claims 1
- SNQFPJMSDNJXQK-UHFFFAOYSA-N 2-bromo-n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1Br SNQFPJMSDNJXQK-UHFFFAOYSA-N 0.000 claims 1
- PIVSGIXKFPHGRW-UHFFFAOYSA-N 2-bromo-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Br PIVSGIXKFPHGRW-UHFFFAOYSA-N 0.000 claims 1
- CQTPKIQGFCRYMU-UHFFFAOYSA-N 2-bromo-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-5-(trifluoromethyl)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1Br CQTPKIQGFCRYMU-UHFFFAOYSA-N 0.000 claims 1
- UGQAGPROPDCARW-UHFFFAOYSA-N 2-bromo-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC=C1Br UGQAGPROPDCARW-UHFFFAOYSA-N 0.000 claims 1
- WETJGGZJCVARJR-UHFFFAOYSA-N 2-chloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC=C1Cl WETJGGZJCVARJR-UHFFFAOYSA-N 0.000 claims 1
- ODGRLWPAAJWEDN-UHFFFAOYSA-N 2-cyano-n-[3-fluoro-4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1C#N ODGRLWPAAJWEDN-UHFFFAOYSA-N 0.000 claims 1
- JLJYBNBKBKTOPB-UHFFFAOYSA-N 2-fluoro-n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1F JLJYBNBKBKTOPB-UHFFFAOYSA-N 0.000 claims 1
- MQGAOJGIKJXEON-UHFFFAOYSA-N 3,4-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 MQGAOJGIKJXEON-UHFFFAOYSA-N 0.000 claims 1
- FXIUPWSIBZMRRX-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-2-hydroxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1O FXIUPWSIBZMRRX-UHFFFAOYSA-N 0.000 claims 1
- PUOYRMWWZJQWHC-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-2-methoxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1OC PUOYRMWWZJQWHC-UHFFFAOYSA-N 0.000 claims 1
- QBAUIKBQAAHYOY-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 QBAUIKBQAAHYOY-UHFFFAOYSA-N 0.000 claims 1
- YSUDQZJQQSRLAM-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-methylphenyl]-2-methoxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1C)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1OC YSUDQZJQQSRLAM-UHFFFAOYSA-N 0.000 claims 1
- NTZTYNGUMBNESK-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-methylphenyl]-4-hydroxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1C)=CC=C1NS(=O)(=O)C1=CC(Cl)=C(O)C(Cl)=C1 NTZTYNGUMBNESK-UHFFFAOYSA-N 0.000 claims 1
- OHVWTIHKXOFGPZ-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-methylphenyl]-2-methoxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)C)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1OC OHVWTIHKXOFGPZ-UHFFFAOYSA-N 0.000 claims 1
- ZYJATWGJGQNEMU-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-4-hydroxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=C(O)C(Cl)=C1 ZYJATWGJGQNEMU-UHFFFAOYSA-N 0.000 claims 1
- YRWKZPIPFHIXAU-UHFFFAOYSA-N 3,5-dichloro-n-[4-(6-fluoro-2-methylquinolin-4-yl)oxyphenyl]-2-hydroxybenzenesulfonamide Chemical compound C=12C=C(F)C=CC2=NC(C)=CC=1OC(C=C1)=CC=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1O YRWKZPIPFHIXAU-UHFFFAOYSA-N 0.000 claims 1
- HBLDAGVLHHGXQR-UHFFFAOYSA-N 3-bromo-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-5-(trifluoromethyl)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC(Br)=CC(C(F)(F)F)=C1 HBLDAGVLHHGXQR-UHFFFAOYSA-N 0.000 claims 1
- LJJGSNSTKZKIPJ-UHFFFAOYSA-N 3-bromo-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC(Br)=C1 LJJGSNSTKZKIPJ-UHFFFAOYSA-N 0.000 claims 1
- AGHWNEZVTDGOFR-UHFFFAOYSA-N 3-chloro-4-fluoro-N-[2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]benzenesulfonamide 2-methyl-1H-imidazole-5-sulfonic acid Chemical compound CC1=NC=C(N1)S(=O)(=O)O.ClC=1C=C(C=CC1F)S(=O)(=O)NC1=C(C=C(C=C1)OC1=CC(=NC2=C(C=CC=C12)C(F)(F)F)C)F AGHWNEZVTDGOFR-UHFFFAOYSA-N 0.000 claims 1
- GHJHSTBIQAHWBT-UHFFFAOYSA-N 3-chloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-4-fluorobenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=C(F)C(Cl)=C1 GHJHSTBIQAHWBT-UHFFFAOYSA-N 0.000 claims 1
- WNYHQHBQGYFCAR-UHFFFAOYSA-N 3-chloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC(Cl)=C1 WNYHQHBQGYFCAR-UHFFFAOYSA-N 0.000 claims 1
- LPZKDGXURIEYIP-UHFFFAOYSA-N 3-chloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-4-methoxybenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1OC1=CC=NC2=CC(OC)=C(OC)C=C12 LPZKDGXURIEYIP-UHFFFAOYSA-N 0.000 claims 1
- MVLNDUYPIKVWDO-UHFFFAOYSA-N 3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyaniline Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC1=CC=C(N)C=C1F MVLNDUYPIKVWDO-UHFFFAOYSA-N 0.000 claims 1
- BIOLYGUGLIHXQV-UHFFFAOYSA-N 3-fluoro-n-[3-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]-4-methoxybenzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1S(=O)(=O)NC(C=C1F)=CC=C1OC1=CC(C)=NC2=C(C(F)(F)F)C=CC=C12 BIOLYGUGLIHXQV-UHFFFAOYSA-N 0.000 claims 1
- HMSYGCKBJLNJHR-UHFFFAOYSA-N 3-tert-butyl-n-[4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-4-methoxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(OC)C(C(C)(C)C)=C1 HMSYGCKBJLNJHR-UHFFFAOYSA-N 0.000 claims 1
- RYOKBRAVFINWEI-UHFFFAOYSA-N 4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxy-2-methylaniline Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC1=CC=C(N)C(C)=C1 RYOKBRAVFINWEI-UHFFFAOYSA-N 0.000 claims 1
- UJJMUWMUKSTWJM-UHFFFAOYSA-N 4-bromo-3-chloro-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=C(Br)C(Cl)=C1 UJJMUWMUKSTWJM-UHFFFAOYSA-N 0.000 claims 1
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| EP2311809A1 (en) * | 2009-10-16 | 2011-04-20 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Quinolinyloxyphenylsulfonamides |
| EP2423208A1 (en) * | 2010-08-28 | 2012-02-29 | Lead Discovery Center GmbH | Pharmaceutically active compounds as Axl inhibitors |
| ITRM20100537A1 (it) | 2010-10-12 | 2012-04-12 | Consiglio Nazionale Ricerche | Aptamero inibitore del recettore tirosina chinasi axl per uso in terapia |
| EA023521B1 (ru) * | 2011-11-14 | 2016-06-30 | Сефалон, Инк. | ПРОИЗВОДНЫЕ УРАЦИЛА В КАЧЕСТВЕ ИНГИБИТОРОВ AXL И c-MET КИНАЗЫ |
| SG11201404505PA (en) | 2012-01-31 | 2014-10-30 | Daiichi Sankyo Co Ltd | Pyridone derivative |
| WO2014018535A1 (en) | 2012-07-25 | 2014-01-30 | Salk Institute For Biological Studies | Regulating the interaction between tam ligands and lipid membranes with exposed phosphatidylserine |
| 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 |
| AU2014353006B2 (en) | 2013-11-20 | 2019-04-04 | Signalchem Life Sciences Corp. | Quinazoline derivatives as TAM family kinase inhibitors |
| CA2922542A1 (en) | 2013-11-22 | 2015-05-28 | University Of Kentucky Research Foundation | Arylquinoline and analog compounds and use thereof to treat cancer |
| JP6496731B2 (ja) | 2013-11-27 | 2019-04-03 | シグナルケム・ライフサイエンシーズ・コーポレイションＳｉｇｎａｌｃｈｅｍ Ｌｉｆｅｓｃｉｅｎｃｅｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｔａｍファミリーキナーゼ阻害剤としてのアミノピリジン誘導体 |
| TWI723572B (zh) | 2014-07-07 | 2021-04-01 | 日商第一三共股份有限公司 | 具有四氫吡喃基甲基之吡啶酮衍生物及其用途 |
| 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 |
| US9840503B2 (en) | 2015-05-11 | 2017-12-12 | Incyte Corporation | Heterocyclic compounds and uses thereof |
| WO2017027717A1 (en) | 2015-08-12 | 2017-02-16 | Incyte Corporation | Bicyclic fused pyrimidine compounds as tam inhibitors |
| WO2017035366A1 (en) | 2015-08-26 | 2017-03-02 | Incyte Corporation | Pyrrolopyrimidine derivatives as tam inhibitors |
| ES2896079T3 (es) | 2016-02-26 | 2022-02-23 | Ono Pharmaceutical Co | Fármaco para la terapia del cáncer, caracterizado por la administración de la combinación entre un inhibidor de Axl y un inhibidor del punto de control inmunitario |
| TWI828027B (zh) | 2016-03-28 | 2024-01-01 | 美商英塞特公司 | 作為tam抑制劑之吡咯并三嗪化合物 |
| CN108250200A (zh) * | 2016-12-28 | 2018-07-06 | 中国科学院上海药物研究所 | 一种具有Axl抑制活性的化合物及其制备和应用 |
| KR102571911B1 (ko) | 2017-01-26 | 2023-08-28 | 오노 야꾸힝 고교 가부시키가이샤 | 퀴놀린 유도체의 에탄술폰산염 |
| EP3673907A4 (en) | 2017-08-23 | 2020-08-19 | ONO Pharmaceutical Co., Ltd. | CANCER TREATMENT PHARMACEUTICAL INCLUDING AX1 INHIBITOR AS AN EFFECTIVE INGREDIENT |
| AU2018325445A1 (en) * | 2017-08-31 | 2020-03-19 | Abbvie Inc. | Ectonucleotide pyrophosphatase-phosphodiesterase 1 (ENPP-1) inhibitors and uses thereof |
| US10633387B2 (en) | 2017-09-27 | 2020-04-28 | Incyte Corporation | Salts of TAM inhibitors |
| US11826363B2 (en) | 2017-10-13 | 2023-11-28 | Ono Pharmaceutical Co., Ltd. | Therapeutic agent for solid cancers, which comprises Axl inhibitor as active ingredient |
| ES3031110T3 (en) | 2018-06-29 | 2025-07-04 | Incyte Corp | Formulations of an axl/mer inhibitor |
| CA3129665A1 (en) | 2019-03-21 | 2020-09-24 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| PH12022552347A1 (en) | 2020-03-06 | 2024-01-29 | Incyte Corp | Combination therapy comprising axl/mer and pd-1/pd-l1 inhibitors |
| US20230295114A1 (en) * | 2020-05-08 | 2023-09-21 | Georgiamune Llc | Akt3 modulators |
| JP2022104746A (ja) * | 2020-12-29 | 2022-07-11 | 国立研究開発法人国立がん研究センター | 抗がん剤 |
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| GB9510757D0 (en) * | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| IL144461A0 (en) * | 1999-01-22 | 2002-05-23 | Kirin Brewery | Quinoline and quinazoline derivatives and pharmaceutical compositions containing them |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| WO2004039782A1 (ja) * | 2002-10-29 | 2004-05-13 | Kirin Beer Kabushiki Kaisha | Ｆｌｔ３自己リン酸化を阻害するキノリン誘導体およびキナゾリン誘導体並びにそれらを含有する医薬組成物 |
| 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 |
| GB0509227D0 (en) * | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Intracellular enzyme inhibitors |
| US20100234371A1 (en) * | 2005-08-22 | 2010-09-16 | Frank Himmelsbach | Bicyclic heterocycles, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof |
| US20110053931A1 (en) * | 2006-06-08 | 2011-03-03 | John Gaudino | Quinoline compounds and methods of use |
| WO2008076415A1 (en) * | 2006-12-14 | 2008-06-26 | Exelixis, Inc. | Methods of using mek inhibitors |
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