RU2010146474A - Производные хинолина в качестве ингибиторов axl киназ - Google Patents
Производные хинолина в качестве ингибиторов axl киназ Download PDFInfo
- Publication number
- RU2010146474A RU2010146474A RU2010146474/04A RU2010146474A RU2010146474A RU 2010146474 A RU2010146474 A RU 2010146474A RU 2010146474/04 A RU2010146474/04 A RU 2010146474/04A RU 2010146474 A RU2010146474 A RU 2010146474A RU 2010146474 A RU2010146474 A RU 2010146474A
- Authority
- RU
- Russia
- Prior art keywords
- yloxy
- dimethoxyquinolin
- fluoro
- phenyl
- fluorophenyl
- Prior art date
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 32
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 31
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 28
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract 14
- 150000002367 halogens Chemical class 0.000 claims abstract 14
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- -1 4 - {[6,7-bis (methyloxy) quinolin-4-yl] oxy} -3-fluorophenyl Chemical group 0.000 claims 86
- 125000003545 alkoxy group Chemical group 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 8
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 claims 6
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- CLHYZIJPOCRHLT-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-phenylmethanesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 CLHYZIJPOCRHLT-UHFFFAOYSA-N 0.000 claims 2
- BPBNPYIAQQQYEC-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-phenylethanesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NS(=O)(=O)CCC1=CC=CC=C1 BPBNPYIAQQQYEC-UHFFFAOYSA-N 0.000 claims 2
- FYPKKMXVPZRAMM-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-phenylpropane-1-sulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NS(=O)(=O)CCCC1=CC=CC=C1 FYPKKMXVPZRAMM-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- CEMRXHMUMZOIMA-NRFANRHFSA-N (2s)-2-amino-4-[4-[4-(benzenesulfonamido)phenoxy]-6-methoxyquinolin-7-yl]oxybutanoic acid Chemical compound C1=CN=C2C=C(OCC[C@H](N)C(O)=O)C(OC)=CC2=C1OC(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=C1 CEMRXHMUMZOIMA-NRFANRHFSA-N 0.000 claims 1
- UZMQSZBTFGHLAH-UHFFFAOYSA-N 1-benzothiophene-2-sulfonamide Chemical compound C1=CC=C2SC(S(=O)(=O)N)=CC2=C1 UZMQSZBTFGHLAH-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
- PJPREWNCIPMGIS-UHFFFAOYSA-N 2-(sulfamoylamino)ethylbenzene Chemical compound NS(=O)(=O)NCCC1=CC=CC=C1 PJPREWNCIPMGIS-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
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 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
- 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
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- 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
- MCAXOOCHYNKTRY-UHFFFAOYSA-N 3-phenylpropane-1-sulfonamide Chemical compound NS(=O)(=O)CCCC1=CC=CC=C1 MCAXOOCHYNKTRY-UHFFFAOYSA-N 0.000 claims 1
- XNDXOXZLMPILOY-UHFFFAOYSA-N 4-(6-fluoro-2-methylquinolin-4-yl)oxyaniline Chemical compound C=12C=C(F)C=CC2=NC(C)=CC=1OC1=CC=C(N)C=C1 XNDXOXZLMPILOY-UHFFFAOYSA-N 0.000 claims 1
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- IBXYLWORFFCGIO-UHFFFAOYSA-N n-[2-[[4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]sulfamoyl]-4-methylphenyl]acetamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NS(=O)(=O)C1=CC(C)=CC=C1NC(C)=O IBXYLWORFFCGIO-UHFFFAOYSA-N 0.000 claims 1
- DQZMVEZUSRVLLL-UHFFFAOYSA-N n-[2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F DQZMVEZUSRVLLL-UHFFFAOYSA-N 0.000 claims 1
- XMVAJGBZEWGNER-UHFFFAOYSA-N n-[2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]-3-phenoxybenzenesulfonamide Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 XMVAJGBZEWGNER-UHFFFAOYSA-N 0.000 claims 1
- AUJGZICLKYBIPV-UHFFFAOYSA-N n-[2-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]-3-pyrimidin-2-ylbenzenesulfonamide Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C)=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C(C=1)=CC=CC=1C1=NC=CC=N1 AUJGZICLKYBIPV-UHFFFAOYSA-N 0.000 claims 1
- HGILZURCHOOWFL-UHFFFAOYSA-N n-[3-fluoro-4-[2-methyl-8-(trifluoromethyl)quinolin-4-yl]oxyphenyl]-2-methoxy-4,5-dimethylbenzenesulfonamide Chemical compound COC1=CC(C)=C(C)C=C1S(=O)(=O)NC(C=C1F)=CC=C1OC1=CC(C)=NC2=C(C(F)(F)F)C=CC=C12 HGILZURCHOOWFL-UHFFFAOYSA-N 0.000 claims 1
- DNAYUZSKXSXMCG-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxyphenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F DNAYUZSKXSXMCG-UHFFFAOYSA-N 0.000 claims 1
- NQZSUAGKUTXWTM-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxyphenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F NQZSUAGKUTXWTM-UHFFFAOYSA-N 0.000 claims 1
- QUGKRUKKYKDDPE-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F QUGKRUKKYKDDPE-UHFFFAOYSA-N 0.000 claims 1
- DXASYTJLINRTNC-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F DXASYTJLINRTNC-UHFFFAOYSA-N 0.000 claims 1
- ANEMTBCHFNGNKN-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-nitrobenzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O ANEMTBCHFNGNKN-UHFFFAOYSA-N 0.000 claims 1
- DKUMVEBCACFXHR-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-[3-(3-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CC(C)CCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F DKUMVEBCACFXHR-UHFFFAOYSA-N 0.000 claims 1
- IYVDLYGGYGAZDG-UHFFFAOYSA-N 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=CC=CC=C1 IYVDLYGGYGAZDG-UHFFFAOYSA-N 0.000 claims 1
- LCVQVBQTRQBYFW-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCC(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F LCVQVBQTRQBYFW-UHFFFAOYSA-N 0.000 claims 1
- DGKPSIOJHHBXOP-UHFFFAOYSA-N n-[3-fluoro-4-[6-methoxy-7-[3-(4-methylpiperidin-1-yl)propoxy]quinolin-4-yl]oxyphenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN3CCC(C)CC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F DGKPSIOJHHBXOP-UHFFFAOYSA-N 0.000 claims 1
- LVAIWZSPTRRMJF-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F LVAIWZSPTRRMJF-UHFFFAOYSA-N 0.000 claims 1
- OYXJFOYFFCYFSB-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-2-fluorobenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC=C1F OYXJFOYFFCYFSB-UHFFFAOYSA-N 0.000 claims 1
- MJORPIAXGHONNI-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 MJORPIAXGHONNI-UHFFFAOYSA-N 0.000 claims 1
- SGDIGARZUXTLJY-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-3-fluoro-4-methylbenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NS(=O)(=O)C1=CC=C(C)C(F)=C1 SGDIGARZUXTLJY-UHFFFAOYSA-N 0.000 claims 1
- DCDMRCXPJNHLEC-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-methylphenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1C)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F DCDMRCXPJNHLEC-UHFFFAOYSA-N 0.000 claims 1
- FRFDJSWHXNODPN-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F FRFDJSWHXNODPN-UHFFFAOYSA-N 0.000 claims 1
- IWUPZOAWKBJWOW-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-phenoxybenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NS(=O)(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 IWUPZOAWKBJWOW-UHFFFAOYSA-N 0.000 claims 1
- MNVAHBAHBJDUKV-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-4-fluoro-3-methoxybenzenesulfonamide Chemical compound C1=C(F)C(OC)=CC(S(=O)(=O)NC=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)=C1 MNVAHBAHBJDUKV-UHFFFAOYSA-N 0.000 claims 1
- ARVUKFJJGWDCIY-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-methoxyphenyl]-4-fluoro-3-methoxybenzenesulfonamide Chemical compound C1=C(F)C(OC)=CC(S(=O)(=O)NC=2C=C(OC)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)=C1 ARVUKFJJGWDCIY-UHFFFAOYSA-N 0.000 claims 1
- VVKSINSBIIMVIJ-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-methylphenyl]-2,5-difluorobenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)C)=CC=C1NS(=O)(=O)C1=CC(F)=CC=C1F VVKSINSBIIMVIJ-UHFFFAOYSA-N 0.000 claims 1
- QPLFPODRTCFSKN-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-methylphenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)C)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F QPLFPODRTCFSKN-UHFFFAOYSA-N 0.000 claims 1
- JGUOSEPJHWHOPV-UHFFFAOYSA-N n-[4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxy-2-methylphenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C=C1C)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F JGUOSEPJHWHOPV-UHFFFAOYSA-N 0.000 claims 1
- HEKLJAHZKJCFKF-UHFFFAOYSA-N n-[4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yl]oxy-2-methylphenyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1OC(C=C1C)=CC=C1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F HEKLJAHZKJCFKF-UHFFFAOYSA-N 0.000 claims 1
- XYWRXVFEHVSGFS-UHFFFAOYSA-N n-[4-[7-(3-aminopropoxy)-6-methoxyquinolin-4-yl]oxy-3-fluorophenyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CN=C2C=C(OCCCN)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F XYWRXVFEHVSGFS-UHFFFAOYSA-N 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- OBEXCUIHNVASQT-UHFFFAOYSA-N tert-butyl n-[3-[4-[2-fluoro-4-[[2-(trifluoromethoxy)phenyl]sulfonylamino]phenoxy]-6-methoxyquinolin-7-yl]oxypropyl]carbamate Chemical compound C1=CN=C2C=C(OCCCNC(=O)OC(C)(C)C)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F OBEXCUIHNVASQT-UHFFFAOYSA-N 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 0 *c(c(*)c1*)c(*)c2c1nc(*)c(*)c2Oc(c(*)c1*)c(*)c(*)c1N(*)S(*)(=O)=O Chemical compound *c(c(*)c1*)c(*)c2c1nc(*)c(*)c2Oc(c(*)c1*)c(*)c(*)c1N(*)S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4539808P | 2008-04-16 | 2008-04-16 | |
| US61/045,398 | 2008-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2010146474A true RU2010146474A (ru) | 2012-05-27 |
Family
ID=40999731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010146474/04A RU2010146474A (ru) | 2008-04-16 | 2009-04-16 | Производные хинолина в качестве ингибиторов axl киназ |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9206130B2 (enExample) |
| EP (1) | EP2262772B8 (enExample) |
| JP (1) | JP5746015B2 (enExample) |
| KR (1) | KR101325237B1 (enExample) |
| CN (1) | CN102131783A (enExample) |
| AU (1) | AU2009237938A1 (enExample) |
| CA (1) | CA2718538A1 (enExample) |
| ES (1) | ES2391373T3 (enExample) |
| IL (1) | IL208103A (enExample) |
| MX (1) | MX2010011224A (enExample) |
| RU (1) | RU2010146474A (enExample) |
| WO (1) | WO2009127417A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP3045453A1 (en) * | 2011-11-14 | 2016-07-20 | Cephalon, Inc. | Uracil derivatives as axl and c-met kinase inhibitors |
| DK2810937T3 (en) | 2012-01-31 | 2017-03-13 | Daiichi Sankyo Co Ltd | PYRIDONE DERIVATIVES |
| US20150164800A1 (en) | 2012-07-25 | 2015-06-18 | Xetrios Therapeutics, Inc. | Regulating the interaction between tam ligands and lipid membranes with exposed phosphatidyl serine |
| 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 |
| US9771333B2 (en) | 2013-11-20 | 2017-09-26 | Signalchem Lifesciences Corp. | Quinazoline derivatives as TAM family kinase inhibitors |
| US9873670B2 (en) | 2013-11-22 | 2018-01-23 | University Of Kentucky Research Foundation | Arylquinoline and analog compounds and use thereof to treat cancer |
| EP3074390B1 (en) | 2013-11-27 | 2020-07-08 | SignalChem Lifesciences Corporation | Aminopyridine derivatives as tam family kinase inhibitors |
| 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 |
| ES2749726T3 (es) * | 2014-12-25 | 2020-03-23 | Ono Pharmaceutical Co | Derivado de quinolina |
| WO2016183071A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Hetero-tricyclic compounds and their use for the treatment of cancer |
| 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 |
| JP7034084B2 (ja) | 2016-03-28 | 2022-03-11 | インサイト・コーポレイション | Ｔａｍ阻害剤としてのピロロトリアジン化合物 |
| 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 |
| HUE054883T2 (hu) | 2017-01-26 | 2021-10-28 | Ono Pharmaceutical Co | N-{5-[(6,7-dimetoxi-4-kinolinil)oxi]-2-piridinil}-2,5-dioxo-1-fenil-1,2,5,6,7,8-hexahidro-3-kinolinkarboxamid etánszulfonát sója |
| US20200197385A1 (en) | 2017-08-23 | 2020-06-25 | Ono Pharmaceutical Co., Ltd. | Therapeutic agent for cancer containing axl inhibitor as active ingredient |
| CA3074013A1 (en) * | 2017-08-31 | 2019-03-07 | Abbvie Inc. | Ectonucleotide pyrophosphatase-phosphodiesterase 1 (enpp-1) inhibitors and uses thereof |
| CA3077308A1 (en) | 2017-09-27 | 2019-04-04 | Incyte Corporation | Salts of pyrrolotriazine derivatives useful as tam inhibitors |
| WO2019074116A1 (ja) | 2017-10-13 | 2019-04-18 | 小野薬品工業株式会社 | Ａｘｌ阻害剤を有効成分として含む固形がん治療剤 |
| EA202190153A1 (ru) | 2018-06-29 | 2021-04-09 | Инсайт Корпорейшн | Составы ингибитора axl/mer |
| KR20210142154A (ko) | 2019-03-21 | 2021-11-24 | 옹쎄오 | 암 치료를 위한 키나제 억제제와 조합된 dbait 분자 |
| JP2023500906A (ja) | 2019-11-08 | 2023-01-11 | インサーム（インスティテュ ナシオナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシェ メディカル） | キナーゼ阻害剤に対する獲得抵抗性を有するがんの処置方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| AU2021230385A1 (en) | 2020-03-06 | 2022-09-22 | Incyte Corporation | Combination therapy comprising AXL/MER and PD-1/PD-L1 inhibitors |
| CA3182673A1 (en) * | 2020-05-08 | 2021-11-11 | 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 |
| HU230789B1 (en) * | 1999-01-22 | 2018-05-02 | Kyowa Hakko Kirin Co | Quinoline derivatives and quinazoline derivatives, pharmaceutical compositions containing them and their use |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| EP1566379A4 (en) * | 2002-10-29 | 2005-11-09 | Kirin Brewery | CHINOLINE DERIVATIVES AND CHINAZOLINE DERIVATIVES AS INHIBITORS OF FLT3 AUTOPHOSPHORYLATION AND THE MEDICAL COMPOSITIONS CONTAINING THEREOF |
| CA2744997A1 (en) * | 2003-09-26 | 2005-04-07 | Exelixis, Inc. | C-met modulators and method of use |
| GB0509227D0 (en) | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Intracellular enzyme inhibitors |
| EP1919900A2 (de) * | 2005-08-22 | 2008-05-14 | Boehringer Ingelheim International Gmbh | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| CN101528702A (zh) * | 2006-06-08 | 2009-09-09 | 阿雷生物药品公司 | 喹啉化合物和使用方法 |
| CN105106199A (zh) * | 2006-12-14 | 2015-12-02 | 埃克塞利希斯股份有限公司 | 使用mek抑制剂的方法 |
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- 2009-04-16 AU AU2009237938A patent/AU2009237938A1/en not_active Abandoned
- 2009-04-16 KR KR1020107023097A patent/KR101325237B1/ko active Active
- 2009-04-16 MX MX2010011224A patent/MX2010011224A/es not_active Application Discontinuation
- 2009-04-16 US US12/933,070 patent/US9206130B2/en active Active
- 2009-04-16 EP EP09731679A patent/EP2262772B8/en active Active
- 2009-04-16 CA CA2718538A patent/CA2718538A1/en not_active Abandoned
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| KR20100132038A (ko) | 2010-12-16 |
| WO2009127417A1 (en) | 2009-10-22 |
| ES2391373T3 (es) | 2012-11-23 |
| US20110092503A1 (en) | 2011-04-21 |
| JP5746015B2 (ja) | 2015-07-08 |
| EP2262772A1 (en) | 2010-12-22 |
| EP2262772B1 (en) | 2012-07-18 |
| EP2262772B8 (en) | 2013-03-13 |
| IL208103A0 (en) | 2010-12-30 |
| AU2009237938A1 (en) | 2009-10-22 |
| JP2011517689A (ja) | 2011-06-16 |
| CA2718538A1 (en) | 2009-10-22 |
| MX2010011224A (es) | 2011-02-25 |
| IL208103A (en) | 2015-08-31 |
| US9206130B2 (en) | 2015-12-08 |
| CN102131783A (zh) | 2011-07-20 |
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