JP2010504322A5 - - Google Patents
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- Publication number
- JP2010504322A5 JP2010504322A5 JP2009528851A JP2009528851A JP2010504322A5 JP 2010504322 A5 JP2010504322 A5 JP 2010504322A5 JP 2009528851 A JP2009528851 A JP 2009528851A JP 2009528851 A JP2009528851 A JP 2009528851A JP 2010504322 A5 JP2010504322 A5 JP 2010504322A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- yloxy
- pyridin
- quinolin
- isoquinolin
- 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
Links
- -1 3,5-dimethylphenyl Chemical group 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 44
- 150000003839 salts Chemical class 0.000 claims 25
- 239000012453 solvate Substances 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 229910052801 chlorine Inorganic materials 0.000 claims 13
- 239000000460 chlorine Substances 0.000 claims 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 9
- 150000003248 quinolines Chemical class 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 206010022489 Insulin Resistance Diseases 0.000 claims 7
- 201000001421 hyperglycemia Diseases 0.000 claims 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 7
- 208000030159 metabolic disease Diseases 0.000 claims 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 229910052740 iodine Inorganic materials 0.000 claims 5
- 239000011630 iodine Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- VZDJWWHLGCWIIA-UHFFFAOYSA-N 2,4-dichloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 VZDJWWHLGCWIIA-UHFFFAOYSA-N 0.000 claims 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 4
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 4
- OTZUJWVQVDBYIR-UHFFFAOYSA-N 2-chloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-fluorobenzenesulfonamide Chemical compound ClC1=CC(F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 OTZUJWVQVDBYIR-UHFFFAOYSA-N 0.000 claims 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- XJFSPAKUIBPXBM-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 XJFSPAKUIBPXBM-UHFFFAOYSA-N 0.000 claims 4
- BCMWMAIMINSPJP-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 BCMWMAIMINSPJP-UHFFFAOYSA-N 0.000 claims 4
- 150000002828 nitro derivatives Chemical class 0.000 claims 4
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- ZQDAOFZWMRGACM-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-2,4-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 ZQDAOFZWMRGACM-UHFFFAOYSA-N 0.000 claims 3
- NTMPTZVLGPNHAL-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 NTMPTZVLGPNHAL-UHFFFAOYSA-N 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- MWPGLYUVXSTKSC-UHFFFAOYSA-N 2,4-dichloro-n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-n-(2,4-dichlorophenyl)sulfonylbenzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)N(S(=O)(=O)C=1C(=CC(Cl)=CC=1)Cl)C(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 MWPGLYUVXSTKSC-UHFFFAOYSA-N 0.000 claims 2
- AYIWOLSTBMMCLV-UHFFFAOYSA-N 2,4-dichloro-n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 AYIWOLSTBMMCLV-UHFFFAOYSA-N 0.000 claims 2
- VEIZLLKUMTZAMG-UHFFFAOYSA-N 2,4-dichloro-n-(5-chloro-6-quinolin-6-yloxypyridin-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=C(N=CC=C2)C2=C1 VEIZLLKUMTZAMG-UHFFFAOYSA-N 0.000 claims 2
- GGLOWKLJQFGKOL-UHFFFAOYSA-N 2-chloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-(trifluoromethyl)benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 GGLOWKLJQFGKOL-UHFFFAOYSA-N 0.000 claims 2
- ZPGFCNQSTHXLPQ-UHFFFAOYSA-N 2-chloro-n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-4-(trifluoromethyl)benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 ZPGFCNQSTHXLPQ-UHFFFAOYSA-N 0.000 claims 2
- RRULZHKUVUYAEG-UHFFFAOYSA-N 3,4-dichloro-n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 RRULZHKUVUYAEG-UHFFFAOYSA-N 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- ZHAUHZOLQWLUJT-UHFFFAOYSA-N 3,5-dichloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3N=CC4=CC=CC=C4C=3)=NC=2)=C1 ZHAUHZOLQWLUJT-UHFFFAOYSA-N 0.000 claims 2
- HKUPFCKQZZWEBL-UHFFFAOYSA-N 3,5-dichloro-n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3C=C4C=CC=CC4=NC=3)=NC=2)=C1 HKUPFCKQZZWEBL-UHFFFAOYSA-N 0.000 claims 2
- ZXWFQDWSPOMACE-UHFFFAOYSA-N 3-[(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3N=CC4=CC=CC=C4C=3)=NC=2)=C1 ZXWFQDWSPOMACE-UHFFFAOYSA-N 0.000 claims 2
- SAGNTHHJMFQCPG-UHFFFAOYSA-N 3-chloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-methylbenzenesulfonamide Chemical compound C1=C(Cl)C(C)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 SAGNTHHJMFQCPG-UHFFFAOYSA-N 0.000 claims 2
- VKKUDNYFCLTYGI-UHFFFAOYSA-N 4-[(5-chloro-6-quinolin-3-yloxypyridin-3-yl)amino]-4-oxobutanoic acid Chemical compound ClC1=CC(NC(=O)CCC(=O)O)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 VKKUDNYFCLTYGI-UHFFFAOYSA-N 0.000 claims 2
- GASULYATUXNMLB-UHFFFAOYSA-N 4-chloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-2-fluorobenzenesulfonamide Chemical compound FC1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 GASULYATUXNMLB-UHFFFAOYSA-N 0.000 claims 2
- SOFSFQBXIBUYAG-UHFFFAOYSA-N 4-chloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 SOFSFQBXIBUYAG-UHFFFAOYSA-N 0.000 claims 2
- RJWQBOJEEVCLFW-UHFFFAOYSA-N 4-chloro-n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-2-fluorobenzenesulfonamide Chemical compound FC1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 RJWQBOJEEVCLFW-UHFFFAOYSA-N 0.000 claims 2
- FDEQPAMALQUOJQ-UHFFFAOYSA-N 4-chloro-n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 FDEQPAMALQUOJQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 2
- 201000008980 hyperinsulinism Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ILOLNGWDSKSMIW-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 ILOLNGWDSKSMIW-UHFFFAOYSA-N 0.000 claims 2
- CCKWNRFUKKIUKZ-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-2,4-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 CCKWNRFUKKIUKZ-UHFFFAOYSA-N 0.000 claims 2
- ZLMHPUOCKWQOLR-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-2,4-dimethoxybenzenesulfonamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 ZLMHPUOCKWQOLR-UHFFFAOYSA-N 0.000 claims 2
- ACNJIGDENNMIRR-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C=C(Cl)C(OC=3N=CC4=CC=CC=C4C=3)=NC=2)=C1 ACNJIGDENNMIRR-UHFFFAOYSA-N 0.000 claims 2
- UONSDGCPHQGLCW-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 UONSDGCPHQGLCW-UHFFFAOYSA-N 0.000 claims 2
- SRAUQIHFKZWWLM-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 SRAUQIHFKZWWLM-UHFFFAOYSA-N 0.000 claims 2
- SIAKSPQCVSJZKR-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-3,5-dimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3N=CC4=CC=CC=C4C=3)=NC=2)=C1 SIAKSPQCVSJZKR-UHFFFAOYSA-N 0.000 claims 2
- JWJYWVGWLLHCRA-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-3-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3N=CC4=CC=CC=C4C=3)=NC=2)=C1 JWJYWVGWLLHCRA-UHFFFAOYSA-N 0.000 claims 2
- RFBXZEABAFUCEC-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-3-methylbenzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3N=CC4=CC=CC=C4C=3)=NC=2)=C1 RFBXZEABAFUCEC-UHFFFAOYSA-N 0.000 claims 2
- RQPMOZXMHUMIQH-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 RQPMOZXMHUMIQH-UHFFFAOYSA-N 0.000 claims 2
- YQCUAEZAIKDFGV-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 YQCUAEZAIKDFGV-UHFFFAOYSA-N 0.000 claims 2
- LUEZRZJLNQHEJE-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-cyanobenzenesulfonamide Chemical compound C=1N=C(OC=2N=CC3=CC=CC=C3C=2)C(Cl)=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 LUEZRZJLNQHEJE-UHFFFAOYSA-N 0.000 claims 2
- BQLZNDWIVXNZPE-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 BQLZNDWIVXNZPE-UHFFFAOYSA-N 0.000 claims 2
- HSGNEZLCABGBIV-UHFFFAOYSA-N n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 HSGNEZLCABGBIV-UHFFFAOYSA-N 0.000 claims 2
- HOAFUMGCISXINX-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 HOAFUMGCISXINX-UHFFFAOYSA-N 0.000 claims 2
- TUOFVNQTMUJPTI-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-2,4-dimethoxybenzenesulfonamide Chemical compound COC1=CC(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 TUOFVNQTMUJPTI-UHFFFAOYSA-N 0.000 claims 2
- AIMRNFGTBBQLBK-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-2,6-difluorobenzenesulfonamide Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 AIMRNFGTBBQLBK-UHFFFAOYSA-N 0.000 claims 2
- XAXFAGJYAZYRDM-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-3,4-difluorobenzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 XAXFAGJYAZYRDM-UHFFFAOYSA-N 0.000 claims 2
- UOMJPYKCSPHWLM-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-3,5-dimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3C=C4C=CC=CC4=NC=3)=NC=2)=C1 UOMJPYKCSPHWLM-UHFFFAOYSA-N 0.000 claims 2
- ZOHQVCMGEKBEQZ-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 ZOHQVCMGEKBEQZ-UHFFFAOYSA-N 0.000 claims 2
- ZWKVWTXANSHLFR-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 ZWKVWTXANSHLFR-UHFFFAOYSA-N 0.000 claims 2
- RWEFGDWMJMRXLB-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 RWEFGDWMJMRXLB-UHFFFAOYSA-N 0.000 claims 2
- NYYBXKYKGYDSBX-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound C=1N=C(OC=2C=C3C=CC=CC3=NC=2)C(Cl)=CC=1NS(=O)(=O)C1=CC=CC=C1 NYYBXKYKGYDSBX-UHFFFAOYSA-N 0.000 claims 2
- LSZBUURANWKKIQ-UHFFFAOYSA-N n-(5-chloro-6-quinolin-6-yloxypyridin-3-yl)-2,4-difluorobenzenesulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=C(N=CC=C2)C2=C1 LSZBUURANWKKIQ-UHFFFAOYSA-N 0.000 claims 2
- KKVWTUIKVYMZPQ-UHFFFAOYSA-N n-(5-chloro-6-quinolin-6-yloxypyridin-3-yl)-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC=C(N=CC=C2)C2=C1 KKVWTUIKVYMZPQ-UHFFFAOYSA-N 0.000 claims 2
- BFQZJTJNERTMAV-UHFFFAOYSA-N n-[4-[(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 BFQZJTJNERTMAV-UHFFFAOYSA-N 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- UBPOEWANSHVLDR-UHFFFAOYSA-N n-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-3-fluoro-4-methylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CN=C(C=CC=C2)C2=C1 UBPOEWANSHVLDR-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
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| US84619406P | 2006-09-21 | 2006-09-21 | |
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| US60/875,672 | 2006-12-18 | ||
| PCT/IB2007/053812 WO2008035306A1 (en) | 2006-09-21 | 2007-09-20 | 3 -amino- pyridine derivatives for the treatment of metabolic disorders |
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| JP2009528850A Ceased JP2010504321A (ja) | 2006-09-21 | 2007-09-20 | インスリン抵抗性または高血糖に関連する代謝性障害の治療のためのピリジン誘導体 |
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| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013117963A1 (en) | 2012-02-09 | 2013-08-15 | Piramal Enterprises Limited | Stable oral tablet dosage form of an antidiabetic compound |
| WO2014207508A1 (en) * | 2013-06-27 | 2014-12-31 | Piramal Enterprises Limited | Pyridyl compound suitable for the treatment of metabolic disorders |
| AU2014300673B2 (en) | 2013-06-27 | 2017-12-14 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine D1 ligands |
| EA028614B1 (ru) * | 2014-05-22 | 2017-12-29 | Общество С Ограниченной Ответственностью "Русские Фармацевтические Технологии" | Селективные ингибиторы, нарушающие взаимодействие рецептора фактора роста фибробластов и frs2, для профилактики и лечения рака |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5084085A (en) * | 1986-08-20 | 1992-01-28 | Fmc Corporation | Herbicidal aryloxyphenyltriazolinones and related compounds |
| UA58494C2 (uk) * | 1995-06-07 | 2003-08-15 | Зенека Лімітед | Похідні n-гетероарилпіридинсульфонаміду, фармацевтична композиція, спосіб одержання та спосіб протидії впливам ендотеліну |
| US6583157B2 (en) * | 1998-01-29 | 2003-06-24 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| NZ515087A (en) * | 1999-04-28 | 2003-11-28 | Aventis Pharma Gmbh | Tri-aryl acid derivatives as PPAR receptor ligands |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| SG148834A1 (en) * | 1999-06-30 | 2009-01-29 | Japan Tobacco Inc | Compounds for the modulation of ppary activity |
| PL214670B1 (pl) * | 2000-06-28 | 2013-08-30 | Amgen Inc | Chinolinylowe modulatory PPAR-gamma, kompozycja je zawierajaca, zwiazek do zastosowania w leczeniu lub zapobieganiu chorobom oraz zastosowanie zwiazku do wytwarzania leku |
| RU2337908C2 (ru) * | 2003-06-12 | 2008-11-10 | Ново Нордиск А/С | Пиридинилкарбаматы в качестве ингибиторов гормон-чувствительной липазы |
| US7223761B2 (en) * | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| RU2416608C2 (ru) * | 2004-08-06 | 2011-04-20 | Оцука Фармасьютикал Ко., Лтд. | Ароматическое соединение |
| BRPI0516454A (pt) * | 2004-10-04 | 2008-09-02 | Hoffmann La Roche | compostos, processo para a preparação de um composto, composição farmacêutica que o compreende, sua utilização, método para o tratamento e profilaxia de enfermidades, e de diabetes do tipo ii |
-
2007
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- 2007-09-20 US US12/441,802 patent/US8030324B2/en not_active Expired - Fee Related
- 2007-09-20 WO PCT/IB2007/053811 patent/WO2008035305A2/en not_active Ceased
- 2007-09-20 TW TW096135229A patent/TW200820970A/zh unknown
- 2007-09-20 EP EP07826467A patent/EP2094663B1/en not_active Not-in-force
- 2007-09-20 US US12/441,891 patent/US8269010B2/en not_active Expired - Fee Related
- 2007-09-20 EP EP07826468A patent/EP2094687A1/en not_active Withdrawn
- 2007-09-20 PT PT07826467T patent/PT2094663E/pt unknown
- 2007-09-20 BR BRPI0718510-3A patent/BRPI0718510A2/pt not_active IP Right Cessation
- 2007-09-20 NZ NZ576196A patent/NZ576196A/en not_active IP Right Cessation
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- 2007-09-20 MX MX2009002906A patent/MX2009002906A/es active IP Right Grant
- 2007-09-20 KR KR1020097008116A patent/KR20090074775A/ko not_active Ceased
- 2007-09-20 AU AU2007298539A patent/AU2007298539B2/en not_active Ceased
- 2007-09-20 RU RU2009114545/04A patent/RU2460729C2/ru not_active IP Right Cessation
- 2007-09-20 TW TW096135227A patent/TW200817364A/zh unknown
- 2007-09-20 CA CA002663901A patent/CA2663901A1/en not_active Abandoned
- 2007-09-20 JP JP2009528851A patent/JP5331953B2/ja not_active Expired - Fee Related
- 2007-09-20 WO PCT/IB2007/053812 patent/WO2008035306A1/en not_active Ceased
- 2007-09-20 AT AT07826467T patent/ATE496890T1/de active
- 2007-09-20 NZ NZ576197A patent/NZ576197A/en not_active IP Right Cessation
- 2007-09-20 AU AU2007298540A patent/AU2007298540B2/en not_active Ceased
- 2007-09-20 KR KR1020097008115A patent/KR20090075827A/ko not_active Ceased
- 2007-09-20 BR BRPI0717106-4A patent/BRPI0717106A2/pt not_active IP Right Cessation
- 2007-09-20 JP JP2009528850A patent/JP2010504321A/ja not_active Ceased
- 2007-09-20 PL PL07826467T patent/PL2094663T3/pl unknown
- 2007-09-20 RU RU2009114544/04A patent/RU2448093C2/ru not_active IP Right Cessation
- 2007-09-20 CA CA002663943A patent/CA2663943A1/en not_active Abandoned
- 2007-09-20 MX MX2009002905A patent/MX2009002905A/es active IP Right Grant
- 2007-09-21 AR ARP070104184A patent/AR062941A1/es not_active Application Discontinuation
- 2007-09-21 AR ARP070104183A patent/AR062940A1/es unknown
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2009
- 2009-03-19 IL IL197694A patent/IL197694A0/en unknown
- 2009-03-19 IL IL197695A patent/IL197695A0/en unknown
-
2011
- 2011-08-31 US US13/222,662 patent/US8349862B2/en not_active Expired - Fee Related
-
2012
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- 2012-08-13 US US13/584,134 patent/US20120309786A1/en not_active Abandoned
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