KR20090074775A - 대사성 질환 치료용 3-아미노-피리딘 유도체 - Google Patents
대사성 질환 치료용 3-아미노-피리딘 유도체 Download PDFInfo
- Publication number
- KR20090074775A KR20090074775A KR1020097008116A KR20097008116A KR20090074775A KR 20090074775 A KR20090074775 A KR 20090074775A KR 1020097008116 A KR1020097008116 A KR 1020097008116A KR 20097008116 A KR20097008116 A KR 20097008116A KR 20090074775 A KR20090074775 A KR 20090074775A
- Authority
- KR
- South Korea
- 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.)
- Ceased
Links
- 208000030159 metabolic disease Diseases 0.000 title claims abstract description 26
- 150000003929 3-aminopyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 214
- 150000003839 salts Chemical class 0.000 claims abstract description 65
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000012453 solvate Substances 0.000 claims abstract description 40
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 39
- 125000003118 aryl group Chemical group 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 28
- 201000001421 hyperglycemia Diseases 0.000 claims abstract description 28
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 19
- 239000000843 powder Substances 0.000 claims abstract description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- -1 3,5-dimethylphenyl Chemical group 0.000 claims description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 20
- 239000008103 glucose Substances 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
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- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 235000020824 obesity Nutrition 0.000 claims description 10
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- 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 9
- 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 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
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- 201000008980 hyperinsulinism Diseases 0.000 claims description 9
- 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 9
- 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 9
- 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 9
- 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 9
- 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 9
- 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 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000011630 iodine 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 6
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 6
- 208000029078 coronary artery disease Diseases 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
- 229940086542 triethylamine Drugs 0.000 claims description 6
- 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 description 5
- 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
- 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 description 5
- 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 5
- 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 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
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- 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
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- 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
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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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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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)
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- Hematology (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
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| US60/875,672 | 2006-12-18 |
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| KR20090074775A true KR20090074775A (ko) | 2009-07-07 |
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| KR1020097008116A Ceased KR20090074775A (ko) | 2006-09-21 | 2007-09-20 | 대사성 질환 치료용 3-아미노-피리딘 유도체 |
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| KR1020097008115A Ceased KR20090075827A (ko) | 2006-09-21 | 2007-09-20 | 인슐린 저항 또는 고혈당증에 관련된 대사성 질환용 피리딘 유도체 |
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| JP (2) | JP2010504321A (enExample) |
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| BR (2) | BRPI0717106A2 (enExample) |
| CA (2) | CA2663901A1 (enExample) |
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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 |
| CA2916653C (en) | 2013-06-27 | 2017-07-18 | 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 |
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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 |
| EE200100558A (et) * | 1999-04-28 | 2002-12-16 | Aventis Pharma Deutschland Gmbh | Triarüülhappe derivaat, seda sisaldav farmatseutiline kompositsioon ja ühendi raviotstarbeline kasutamine |
| DK1192137T3 (da) * | 1999-06-30 | 2013-11-11 | Amgen Inc | Forbindelser til modulering af PPAR-gamma aktivitet |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| ES2265435T3 (es) * | 2000-06-28 | 2007-02-16 | Amgen Inc. | Moduladores benzotiazolilo de ppar-gamma. |
| AU2004247319A1 (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 |
| EP1773797A2 (en) * | 2004-08-06 | 2007-04-18 | Otsuka Pharmaceutical Co., Ltd. | Aromatic compounds |
| 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 |
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2007
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- 2007-09-20 TW TW096135227A patent/TW200817364A/zh unknown
- 2007-09-20 AU AU2007298539A patent/AU2007298539B2/en not_active Ceased
- 2007-09-20 NZ NZ576197A patent/NZ576197A/en not_active IP Right Cessation
- 2007-09-20 BR BRPI0717106-4A patent/BRPI0717106A2/pt not_active IP Right Cessation
- 2007-09-20 RU RU2009114544/04A patent/RU2448093C2/ru not_active IP Right Cessation
- 2007-09-20 CA CA002663901A patent/CA2663901A1/en not_active Abandoned
- 2007-09-20 AU AU2007298540A patent/AU2007298540B2/en not_active Ceased
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- 2007-09-20 NZ NZ576196A patent/NZ576196A/en not_active IP Right Cessation
- 2007-09-20 EP EP07826468A patent/EP2094687A1/en not_active Withdrawn
- 2007-09-20 PT PT07826467T patent/PT2094663E/pt unknown
- 2007-09-20 KR KR1020097008116A patent/KR20090074775A/ko not_active Ceased
- 2007-09-20 MX MX2009002906A patent/MX2009002906A/es active IP Right Grant
- 2007-09-20 WO PCT/IB2007/053811 patent/WO2008035305A2/en not_active Ceased
- 2007-09-20 JP JP2009528850A patent/JP2010504321A/ja not_active Ceased
- 2007-09-20 US US12/441,802 patent/US8030324B2/en not_active Expired - Fee Related
- 2007-09-20 DK DK07826467.8T patent/DK2094663T3/da active
- 2007-09-20 BR BRPI0718510-3A patent/BRPI0718510A2/pt not_active IP Right Cessation
- 2007-09-20 TW TW096135229A patent/TW200820970A/zh unknown
- 2007-09-20 AT AT07826467T patent/ATE496890T1/de active
- 2007-09-20 PL PL07826467T patent/PL2094663T3/pl unknown
- 2007-09-20 DE DE602007012299T patent/DE602007012299D1/de active Active
- 2007-09-20 CA CA002663943A patent/CA2663943A1/en not_active Abandoned
- 2007-09-20 JP JP2009528851A patent/JP5331953B2/ja not_active Expired - Fee Related
- 2007-09-20 RU RU2009114545/04A patent/RU2460729C2/ru 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
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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 US13/584,043 patent/US20130040988A1/en not_active Abandoned
- 2012-08-13 US US13/584,134 patent/US20120309786A1/en not_active Abandoned
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