AU2007298540B2 - 3 -amino- pyridine derivatives for the treatment of metabolic disorders - Google Patents
3 -amino- pyridine derivatives for the treatment of metabolic disorders Download PDFInfo
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- AU2007298540B2 AU2007298540B2 AU2007298540A AU2007298540A AU2007298540B2 AU 2007298540 B2 AU2007298540 B2 AU 2007298540B2 AU 2007298540 A AU2007298540 A AU 2007298540A AU 2007298540 A AU2007298540 A AU 2007298540A AU 2007298540 B2 AU2007298540 B2 AU 2007298540B2
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- Prior art keywords
- chloro
- pyridin
- yloxy
- compound
- formula
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 29
- 208000030159 metabolic disease Diseases 0.000 title claims description 23
- 150000003929 3-aminopyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 226
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 23
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 22
- -1 3,5- dimethylphenyl Chemical group 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 66
- 238000002360 preparation method Methods 0.000 claims description 56
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 239000012453 solvate Substances 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- 206010022489 Insulin Resistance Diseases 0.000 claims description 36
- 239000000460 chlorine Substances 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 201000001421 hyperglycemia Diseases 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000011630 iodine Substances 0.000 claims description 13
- 230000009467 reduction Effects 0.000 claims description 13
- 206010020772 Hypertension Diseases 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
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 10
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 10
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 8
- 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
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 150000002828 nitro derivatives Chemical class 0.000 claims description 8
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 8
- 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 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
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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- 201000008980 hyperinsulinism Diseases 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
- 235000020824 obesity Nutrition 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 229940086542 triethylamine Drugs 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 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 6
- 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 6
- 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 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
- 208000006011 Stroke Diseases 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 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 4
- 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 4
- 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 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 230000003143 atherosclerotic effect Effects 0.000 claims description 4
- 208000029078 coronary artery disease Diseases 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 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 description 3
- 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 3
- 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 3
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- 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 3
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Classifications
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- 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
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- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Diabetes (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
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- Epidemiology (AREA)
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- Child & Adolescent Psychology (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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84619406P | 2006-09-21 | 2006-09-21 | |
| US60/846,194 | 2006-09-21 | ||
| US87567206P | 2006-12-18 | 2006-12-18 | |
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2007298540A1 AU2007298540A1 (en) | 2008-03-27 |
| AU2007298540B2 true AU2007298540B2 (en) | 2013-02-21 |
Family
ID=39048032
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007298540A Ceased AU2007298540B2 (en) | 2006-09-21 | 2007-09-20 | 3 -amino- pyridine derivatives for the treatment of metabolic disorders |
| AU2007298539A Ceased AU2007298539B2 (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 |
|---|---|---|---|
| AU2007298539A Ceased AU2007298539B2 (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) | US8269010B2 (https=) |
| EP (2) | EP2094687A1 (https=) |
| JP (2) | JP5331953B2 (https=) |
| KR (2) | KR20090075827A (https=) |
| AR (2) | AR062941A1 (https=) |
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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 |
| SG11201509186TA (en) | 2013-06-27 | 2016-01-28 | Pfizer | Heteroaromatic compounds and their use as dopamine d1 ligands |
| 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 |
| CN116635380A (zh) | 2020-11-09 | 2023-08-22 | 卫材R&D管理有限公司 | PPAR γ 调节剂和使用方法 |
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 |
| EP1177176B1 (en) * | 1999-04-28 | 2006-04-19 | Aventis Pharma Deutschland GmbH | Tri-aryl acid derivatives as ppar receptor ligands |
| IL147308A0 (en) * | 1999-06-30 | 2002-08-14 | Tularik Inc | Compounds for the modulation of pparγ activity and pharmaceutical compositions containing the same |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| KR100771286B1 (ko) * | 2000-06-28 | 2007-10-29 | 암젠 인크 | 퀴놀리닐 및 벤조티아졸릴 ｐｐａｒ-감마 조절물질 |
| BRPI0411255A (pt) * | 2003-06-12 | 2006-08-01 | Novo Nordisk As | composto, composição farmacêutica, uso de um composto, métodos de tratar um distúrbio de um paciente, e, processo para a preparação de um composto |
| US7223761B2 (en) * | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| MX2007001215A (es) * | 2004-08-06 | 2007-04-17 | Otsuka Pharma Co Ltd | Compuestos aromaticos. |
| EP1799647A1 (en) * | 2004-10-04 | 2007-06-27 | F.Hoffmann-La Roche Ag | Alkil-pyridines as 11-beta inhibitors for diabetes |
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2007
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- 2007-09-20 KR KR1020097008115A patent/KR20090075827A/ko not_active Ceased
- 2007-09-20 JP JP2009528851A patent/JP5331953B2/ja not_active Expired - Fee Related
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- 2007-09-20 MX MX2009002906A patent/MX2009002906A/es active IP Right Grant
- 2007-09-20 EP EP07826468A patent/EP2094687A1/en not_active Withdrawn
- 2007-09-20 WO PCT/IB2007/053812 patent/WO2008035306A1/en not_active Ceased
- 2007-09-20 DE DE602007012299T patent/DE602007012299D1/de active Active
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- 2007-09-20 WO PCT/IB2007/053811 patent/WO2008035305A2/en not_active Ceased
- 2007-09-20 TW TW096135227A patent/TW200817364A/zh unknown
- 2007-09-20 KR KR1020097008116A patent/KR20090074775A/ko not_active Ceased
- 2007-09-20 CA CA002663901A patent/CA2663901A1/en not_active Abandoned
- 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
- 2007-09-21 AR ARP070104184A patent/AR062941A1/es not_active Application Discontinuation
- 2007-09-21 AR ARP070104183A patent/AR062940A1/es unknown
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2009
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