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 (https=) |
| EP (1) | EP2262772B8 (https=) |
| JP (1) | JP5746015B2 (https=) |
| KR (1) | KR101325237B1 (https=) |
| CN (1) | CN102131783A (https=) |
| AU (1) | AU2009237938A1 (https=) |
| CA (1) | CA2718538A1 (https=) |
| ES (1) | ES2391373T3 (https=) |
| IL (1) | IL208103A (https=) |
| MX (1) | MX2010011224A (https=) |
| RU (1) | RU2010146474A (https=) |
| WO (1) | WO2009127417A1 (https=) |
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 |
| EP2780338B1 (en) * | 2011-11-14 | 2016-11-09 | Ignyta, Inc. | Uracil derivatives as axl and c-met kinase inhibitors |
| RS55728B1 (sr) | 2012-01-31 | 2017-07-31 | Daiichi Sankyo Co Ltd | Derivat piridona |
| CA2879542A1 (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 |
| JP6527513B2 (ja) | 2013-11-20 | 2019-06-05 | 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キナゾリン誘導体 |
| 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 |
| TWI690525B (zh) | 2014-07-07 | 2020-04-11 | 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 |
| US10053465B2 (en) | 2015-08-26 | 2018-08-21 | Incyte Corporation | Pyrrolopyrimidine derivatives as TAM inhibitors |
| WO2017146236A1 (ja) | 2016-02-26 | 2017-08-31 | 小野薬品工業株式会社 | Ａｘｌ阻害剤と免疫チェックポイント阻害剤とを組み合わせて投与することを特徴とする癌治療のための医薬 |
| MD3436461T2 (ro) | 2016-03-28 | 2024-05-31 | Incyte Corp | Compuși pirolotriazină ca inhibitori TAM |
| 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 |
| EP3575293B1 (en) | 2017-01-26 | 2021-03-10 | ONO Pharmaceutical Co., Ltd. | Ethanesulfonate salt of n-{5-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-pyridinyl}-2,5-dioxo-1-phenyl-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide |
| JP7156287B2 (ja) | 2017-08-23 | 2022-10-19 | 小野薬品工業株式会社 | Ａｘｌ阻害剤を有効成分として含むがん治療剤 |
| MX2020002183A (es) * | 2017-08-31 | 2020-10-05 | Abbvie Inc | Inhibidores de la ectonucleótido pirofosfatasa-fosfodiesterasa 1 (enpp-1) y usos de los mismos. |
| SI3687996T1 (sl) | 2017-09-27 | 2022-04-29 | Incyte Corporation | Soli pirolotriazinskih derivatov, ki so uporabne kot zaviralci TAM |
| EP3695839A4 (en) | 2017-10-13 | 2021-07-14 | ONO Pharmaceutical Co., Ltd. | THERAPEUTIC AGENT WITH AXL INHIBITOR AS AN ACTIVE INGREDIENT FOR SOLID TUMORS |
| MD3813800T2 (ro) | 2018-06-29 | 2025-10-31 | Incyte Corp | Formulări de inhibitor al AXL/MER |
| US20220143049A1 (en) | 2019-03-21 | 2022-05-12 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| EP4054579A1 (en) | 2019-11-08 | 2022-09-14 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
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| 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 |
| AU2003280599A1 (en) * | 2002-10-29 | 2004-05-25 | Kirin Beer Kabushiki Kaisha | QUINOLINE DERIVATIVES AND QUINAZOLINE DERIVATIVES INHIBITING AUTOPHOSPHORYLATION OF Flt3 AND MEDICINAL COMPOSITIONS CONTAINING THE SAME |
| PT2213661E (pt) * | 2003-09-26 | 2011-12-15 | Exelixis Inc | Moduladores de c-met e métodos de uso |
| GB0509227D0 (en) * | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Intracellular enzyme inhibitors |
| CA2619037A1 (en) * | 2005-08-22 | 2007-03-01 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles medicaments comprising said compounds use and method for production thereof |
| JP2009539878A (ja) * | 2006-06-08 | 2009-11-19 | アレイ バイオファーマ、インコーポレイテッド | キノリン化合物および使用方法 |
| WO2008076415A1 (en) | 2006-12-14 | 2008-06-26 | Exelixis, Inc. | Methods of using mek inhibitors |
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| MX2010011224A (es) | 2011-02-25 |
| US20110092503A1 (en) | 2011-04-21 |
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| AU2009237938A1 (en) | 2009-10-22 |
| EP2262772B1 (en) | 2012-07-18 |
| ES2391373T3 (es) | 2012-11-23 |
| CN102131783A (zh) | 2011-07-20 |
| US9206130B2 (en) | 2015-12-08 |
| EP2262772A1 (en) | 2010-12-22 |
| KR20100132038A (ko) | 2010-12-16 |
| JP2011517689A (ja) | 2011-06-16 |
| EP2262772B8 (en) | 2013-03-13 |
| JP5746015B2 (ja) | 2015-07-08 |
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