NZ576197A - 3 -amino- pyridine derivatives for the treatment of metabolic disorders - Google Patents
3 -amino- pyridine derivatives for the treatment of metabolic disordersInfo
- Publication number
- NZ576197A NZ576197A NZ576197A NZ57619707A NZ576197A NZ 576197 A NZ576197 A NZ 576197A NZ 576197 A NZ576197 A NZ 576197A NZ 57619707 A NZ57619707 A NZ 57619707A NZ 576197 A NZ576197 A NZ 576197A
- Authority
- NZ
- New Zealand
- Prior art keywords
- chloro
- yloxy
- pyridin
- quinolin
- isoquinolin
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 25
- 208000030159 metabolic disease Diseases 0.000 title claims description 19
- 150000003929 3-aminopyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- -1 nitro pyridine compound Chemical class 0.000 claims abstract description 94
- 238000000034 method Methods 0.000 claims abstract description 76
- 238000002360 preparation method Methods 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 239000012453 solvate Substances 0.000 claims abstract description 35
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 201000001421 hyperglycemia Diseases 0.000 claims abstract description 21
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 15
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 14
- 206010020772 Hypertension Diseases 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 13
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 11
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims abstract description 8
- 208000008589 Obesity Diseases 0.000 claims abstract description 8
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims abstract description 8
- 201000008980 hyperinsulinism Diseases 0.000 claims abstract description 8
- 235000020824 obesity Nutrition 0.000 claims abstract description 8
- 229940086542 triethylamine Drugs 0.000 claims abstract description 8
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000009467 reduction Effects 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 208000006011 Stroke Diseases 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 5
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims abstract description 5
- 230000003143 atherosclerotic effect Effects 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 208000029078 coronary artery disease Diseases 0.000 claims abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims abstract description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims abstract description 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims abstract description 4
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims abstract description 4
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 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 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 8
- 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 description 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 7
- 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 description 7
- GSDCNZFXWHBELO-UHFFFAOYSA-N 3,4-dichloro-n-(5-chloro-6-isoquinolin-3-yloxypyridin-3-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC(C=C1Cl)=CN=C1OC1=CC2=CC=CC=C2C=N1 GSDCNZFXWHBELO-UHFFFAOYSA-N 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
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Classifications
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Landscapes
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- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84619406P | 2006-09-21 | 2006-09-21 | |
| US87567206P | 2006-12-18 | 2006-12-18 | |
| PCT/IB2007/053812 WO2008035306A1 (en) | 2006-09-21 | 2007-09-20 | 3 -amino- pyridine derivatives for the treatment of metabolic disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ576197A true NZ576197A (en) | 2011-12-22 |
Family
ID=39048032
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ576197A NZ576197A (en) | 2006-09-21 | 2007-09-20 | 3 -amino- pyridine derivatives for the treatment of metabolic disorders |
| NZ576196A NZ576196A (en) | 2006-09-21 | 2007-09-20 | Pyridine derivatives for the treatment of metabolic disorders related to insulin resistance or hyperglycemia |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ576196A NZ576196A (en) | 2006-09-21 | 2007-09-20 | Pyridine derivatives for the treatment of metabolic disorders related to insulin resistance or hyperglycemia |
Country Status (19)
| Country | Link |
|---|---|
| US (5) | US8030324B2 (enExample) |
| EP (2) | EP2094663B1 (enExample) |
| JP (2) | JP5331953B2 (enExample) |
| KR (2) | KR20090075827A (enExample) |
| AR (2) | AR062941A1 (enExample) |
| AT (1) | ATE496890T1 (enExample) |
| AU (2) | AU2007298539B2 (enExample) |
| BR (2) | BRPI0718510A2 (enExample) |
| CA (2) | CA2663901A1 (enExample) |
| DE (1) | DE602007012299D1 (enExample) |
| DK (1) | DK2094663T3 (enExample) |
| IL (2) | IL197695A0 (enExample) |
| MX (2) | MX2009002905A (enExample) |
| NZ (2) | NZ576197A (enExample) |
| PL (1) | PL2094663T3 (enExample) |
| PT (1) | PT2094663E (enExample) |
| RU (2) | RU2448093C2 (enExample) |
| TW (2) | TW200820970A (enExample) |
| WO (2) | WO2008035305A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| PE20160664A1 (es) | 2013-06-27 | 2016-07-09 | Pfizer | Compuestos heteroaromaticos y su uso como ligandos d1 de dopamina |
| WO2014207508A1 (en) * | 2013-06-27 | 2014-12-31 | Piramal Enterprises Limited | Pyridyl compound suitable for the treatment of metabolic disorders |
| 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 |
| MX2023005371A (es) | 2020-11-09 | 2023-05-22 | Eisai R&D Man Co Ltd | Moduladores de receptor gamma activado por proliferador de peroxisoma (ppar gamma) y metodos de uso. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2001000579A1 (en) * | 1999-06-30 | 2001-01-04 | Tularik Inc. | COMPOUNDS FOR THE MODULATION OF PPARη ACTIVITY |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| HK1052351B (en) * | 2000-06-28 | 2006-11-03 | Japan Tobacco Inc. | Benzothiazolyl ppar-gamma modulators |
| CA2526204A1 (en) * | 2003-06-12 | 2004-12-23 | Novo Nordisk A/S | Pyridinyl carbamates as hormone-sensitive lipase inhibitors |
| US7223761B2 (en) * | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| US8188277B2 (en) * | 2004-08-06 | 2012-05-29 | Otsuka Pharmaceutical Co., Ltd. | Aromatic compounds for suppressing the generation of collagen |
| RU2383533C2 (ru) * | 2004-10-04 | 2010-03-10 | Ф.Хоффманн-Ля Рош Аг | Алкилированные производные пиридина в качестве ингибиторов 11-бета при диабете |
-
2007
- 2007-09-20 US US12/441,802 patent/US8030324B2/en not_active Expired - Fee Related
- 2007-09-20 CA CA002663901A patent/CA2663901A1/en not_active Abandoned
- 2007-09-20 NZ NZ576197A patent/NZ576197A/en not_active IP Right Cessation
- 2007-09-20 US US12/441,891 patent/US8269010B2/en not_active Expired - Fee Related
- 2007-09-20 KR KR1020097008115A patent/KR20090075827A/ko not_active Ceased
- 2007-09-20 TW TW096135229A patent/TW200820970A/zh unknown
- 2007-09-20 KR KR1020097008116A patent/KR20090074775A/ko not_active Ceased
- 2007-09-20 DK DK07826467.8T patent/DK2094663T3/da active
- 2007-09-20 AU AU2007298539A patent/AU2007298539B2/en not_active Ceased
- 2007-09-20 WO PCT/IB2007/053811 patent/WO2008035305A2/en not_active Ceased
- 2007-09-20 PL PL07826467T patent/PL2094663T3/pl unknown
- 2007-09-20 DE DE602007012299T patent/DE602007012299D1/de active Active
- 2007-09-20 PT PT07826467T patent/PT2094663E/pt unknown
- 2007-09-20 RU RU2009114544/04A patent/RU2448093C2/ru not_active IP Right Cessation
- 2007-09-20 EP EP07826467A patent/EP2094663B1/en not_active Not-in-force
- 2007-09-20 NZ NZ576196A patent/NZ576196A/en not_active IP Right Cessation
- 2007-09-20 AT AT07826467T patent/ATE496890T1/de active
- 2007-09-20 EP EP07826468A patent/EP2094687A1/en not_active Withdrawn
- 2007-09-20 MX MX2009002905A patent/MX2009002905A/es active IP Right Grant
- 2007-09-20 RU RU2009114545/04A patent/RU2460729C2/ru not_active IP Right Cessation
- 2007-09-20 BR BRPI0718510-3A patent/BRPI0718510A2/pt not_active IP Right Cessation
- 2007-09-20 WO PCT/IB2007/053812 patent/WO2008035306A1/en not_active Ceased
- 2007-09-20 TW TW096135227A patent/TW200817364A/zh unknown
- 2007-09-20 JP JP2009528851A patent/JP5331953B2/ja not_active Expired - Fee Related
- 2007-09-20 AU AU2007298540A patent/AU2007298540B2/en not_active Ceased
- 2007-09-20 MX MX2009002906A patent/MX2009002906A/es active IP Right Grant
- 2007-09-20 JP JP2009528850A patent/JP2010504321A/ja not_active Ceased
- 2007-09-20 CA CA002663943A patent/CA2663943A1/en not_active Abandoned
- 2007-09-20 BR BRPI0717106-4A patent/BRPI0717106A2/pt not_active IP Right Cessation
- 2007-09-21 AR ARP070104184A patent/AR062941A1/es not_active Application Discontinuation
- 2007-09-21 AR ARP070104183A patent/AR062940A1/es unknown
-
2009
- 2009-03-19 IL IL197695A patent/IL197695A0/en unknown
- 2009-03-19 IL IL197694A patent/IL197694A0/en unknown
-
2011
- 2011-08-31 US US13/222,662 patent/US8349862B2/en not_active Expired - Fee Related
-
2012
- 2012-08-13 US US13/584,134 patent/US20120309786A1/en not_active Abandoned
- 2012-08-13 US US13/584,043 patent/US20130040988A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| ASS | Change of ownership |
Owner name: PIRAMAL ENTERPRISES LIMITED, IN Effective date: 20130207 |
|
| LAPS | Patent lapsed |