CA2418104A1 - Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists - Google Patents
Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists Download PDFInfo
- Publication number
- CA2418104A1 CA2418104A1 CA002418104A CA2418104A CA2418104A1 CA 2418104 A1 CA2418104 A1 CA 2418104A1 CA 002418104 A CA002418104 A CA 002418104A CA 2418104 A CA2418104 A CA 2418104A CA 2418104 A1 CA2418104 A1 CA 2418104A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- phenyl
- compound
- oxazol
- propionic acid
- 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.)
- Abandoned
Links
- 239000002253 acid Substances 0.000 title description 20
- 101150014691 PPARA gene Proteins 0.000 title description 11
- 239000000556 agonist Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 306
- -1 thiophen-2,5-diyl Chemical group 0.000 claims abstract description 75
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 239000012453 solvate Substances 0.000 claims abstract description 31
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 25
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 14
- 150000004677 hydrates Chemical class 0.000 claims abstract description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 12
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 115
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
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- 241000124008 Mammalia Species 0.000 claims description 30
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
- 102000005962 receptors Human genes 0.000 claims description 17
- 108020003175 receptors Proteins 0.000 claims description 17
- 210000002966 serum Anatomy 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 15
- 210000004369 blood Anatomy 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 15
- 150000003626 triacylglycerols Chemical class 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 208000011580 syndromic disease Diseases 0.000 claims description 9
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- 102000007330 LDL Lipoproteins Human genes 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
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- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
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- UYZRCSAVQYPXAQ-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(1-methylcyclohexyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-(2-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2(C)CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C UYZRCSAVQYPXAQ-UHFFFAOYSA-N 0.000 claims description 3
- DVIHJHMWKIYVCZ-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(3-thiophen-3-ylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC(C=1)=CC=CC=1C=1C=CSC=1 DVIHJHMWKIYVCZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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- JSTSZHVRXHMZQK-NDEPHWFRSA-N (2s)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound O([C@@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 JSTSZHVRXHMZQK-NDEPHWFRSA-N 0.000 claims description 2
- KWSPYUOBNIMILB-SANMLTNESA-N (2s)-2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound O([C@@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1SC=CC=1)C(O)=O)C1=CC=CC=C1 KWSPYUOBNIMILB-SANMLTNESA-N 0.000 claims description 2
- TYWOJTKDVPFCLY-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC=C1OC(C)(C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 TYWOJTKDVPFCLY-UHFFFAOYSA-N 0.000 claims description 2
- GYDYGMALAVXYJR-UHFFFAOYSA-N 2-methyl-2-(2-methylphenoxy)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C GYDYGMALAVXYJR-UHFFFAOYSA-N 0.000 claims description 2
- XNNSVDBLAAWIHF-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-quinolin-6-yloxypropanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4C=CC=NC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C1=CC=CC=C1 XNNSVDBLAAWIHF-UHFFFAOYSA-N 0.000 claims description 2
- KLYSGRRZNYRRDA-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(2-methoxyphenoxy)-2-methylpropanoic acid Chemical compound COC1=CC=CC=C1OC(C)(C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C2CCCCC2)=N1 KLYSGRRZNYRRDA-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- GGVARJZTVCDHIS-SANMLTNESA-N (2s)-3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(4-methylphenoxy)propanoic acid Chemical compound O([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C1CCCCC1)C(O)=O)C1=CC=C(C)C=C1 GGVARJZTVCDHIS-SANMLTNESA-N 0.000 claims 1
- VITUOJRLJBPZMW-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC=C1OC(C)(C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2SC=CC=2)=N1 VITUOJRLJBPZMW-UHFFFAOYSA-N 0.000 claims 1
- SHUMAHDDIVFREX-UHFFFAOYSA-N 2-(3-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(1-methylcyclohexyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C2(C)CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(Cl)=C1 SHUMAHDDIVFREX-UHFFFAOYSA-N 0.000 claims 1
- QYHAWNLDQLOSNT-UHFFFAOYSA-N 2-(3-chlorophenoxy)-3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methylpropanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(Cl)=C1 QYHAWNLDQLOSNT-UHFFFAOYSA-N 0.000 claims 1
- UGFDMEAQMIZMJH-UHFFFAOYSA-N 2-methyl-2-(2-methylphenoxy)-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C UGFDMEAQMIZMJH-UHFFFAOYSA-N 0.000 claims 1
- KWSPYUOBNIMILB-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 KWSPYUOBNIMILB-UHFFFAOYSA-N 0.000 claims 1
- GGVARJZTVCDHIS-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(4-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)OC1=CC=C(C)C=C1 GGVARJZTVCDHIS-UHFFFAOYSA-N 0.000 claims 1
- ZJASNYLZHSZJRM-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(2-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C ZJASNYLZHSZJRM-UHFFFAOYSA-N 0.000 claims 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- PFFHWUQMSVPUIP-UHFFFAOYSA-N methyl 2-[5-methyl-2-(5-methylthiophen-2-yl)-1,3-oxazol-4-yl]acetate Chemical compound O1C(C)=C(CC(=O)OC)N=C1C1=CC=C(C)S1 PFFHWUQMSVPUIP-UHFFFAOYSA-N 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
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- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22723400P | 2000-08-23 | 2000-08-23 | |
| US60/227,234 | 2000-08-23 | ||
| PCT/US2001/022616 WO2002016331A1 (en) | 2000-08-23 | 2001-08-23 | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2418104A1 true CA2418104A1 (en) | 2002-02-28 |
Family
ID=22852309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002418104A Abandoned CA2418104A1 (en) | 2000-08-23 | 2001-08-23 | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6930120B2 (enExample) |
| EP (1) | EP1313716B1 (enExample) |
| JP (1) | JP2004506721A (enExample) |
| KR (1) | KR20030027054A (enExample) |
| CN (1) | CN1471517A (enExample) |
| AT (1) | ATE361283T1 (enExample) |
| AU (1) | AU2001284659A1 (enExample) |
| BR (1) | BR0113409A (enExample) |
| CA (1) | CA2418104A1 (enExample) |
| CY (1) | CY1107679T1 (enExample) |
| CZ (1) | CZ2003482A3 (enExample) |
| DE (1) | DE60128239T2 (enExample) |
| DK (1) | DK1313716T3 (enExample) |
| EA (1) | EA200300286A1 (enExample) |
| EC (1) | ECSP034504A (enExample) |
| ES (1) | ES2286137T3 (enExample) |
| HU (1) | HUP0300857A3 (enExample) |
| IL (1) | IL154110A0 (enExample) |
| MX (1) | MXPA03001558A (enExample) |
| NO (1) | NO20030729L (enExample) |
| NZ (1) | NZ523804A (enExample) |
| PL (1) | PL360744A1 (enExample) |
| PT (1) | PT1313716E (enExample) |
| SK (1) | SK1872003A3 (enExample) |
| WO (1) | WO2002016331A1 (enExample) |
| ZA (1) | ZA200300570B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6982278B2 (en) | 2000-08-23 | 2006-01-03 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| EP1313717B1 (en) * | 2000-08-23 | 2007-10-17 | Eli Lilly And Company | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
| IL158589A0 (en) * | 2001-05-15 | 2004-05-12 | Hoffmann La Roche | Carboxylic acid substituted oxazole derivatives for use as ppar-alpha and -gamma activators in the treatment of diabetes |
| KR100459917B1 (ko) * | 2001-12-14 | 2004-12-03 | (주)바이오뉴트리젠 | 페놀릭산 유도체 및 이를 포함하는 혈중 지질 농도 관련질환의 예방 및 치료용 조성물 |
| US6833380B2 (en) | 2002-03-07 | 2004-12-21 | Warner-Lambert Company, Llc | Compounds that modulate PPAR activity and methods of preparation |
| US6867224B2 (en) | 2002-03-07 | 2005-03-15 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods of preparation |
| ATE372990T1 (de) | 2002-07-03 | 2007-09-15 | Hoffmann La Roche | Oxazolderivat und deren verwendung als insulinsensibilisatoren |
| MXPA05002115A (es) * | 2002-08-30 | 2005-05-23 | Hoffmann La Roche | Compuestos novedosos de 2-ariltiazol como agonistas de pparalfa y ppargama. |
| NZ537979A (en) | 2002-09-12 | 2007-08-31 | Hoffmann La Roche | N-substituted-1H-indol-5-propionic acid compounds as PPAR agonists useful for the treatment of diabetes |
| TWI343915B (en) | 2002-10-07 | 2011-06-21 | Hoffmann La Roche | Chirale ppar agonists |
| EP1572203B1 (en) | 2002-11-08 | 2007-11-07 | F. Hoffmann-La Roche Ag | Substituted 4-alkoxyoxazol derivatives as ppar agonists |
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| US5089514A (en) * | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
| US5232945A (en) * | 1992-07-20 | 1993-08-03 | Pfizer Inc. | 3-aryl-2-hydroxypropionic acid derivatives and analogs as antihypertensives |
| US6062509A (en) | 1994-12-23 | 2000-05-16 | Hexcel Corporation | Retrofit centerline luggage bin assemblies compatible with existing aircraft bin supports |
| US5902726A (en) * | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
| JP2002503202A (ja) | 1996-02-02 | 2002-01-29 | メルク エンド カンパニー インコーポレーテッド | 抗糖尿病薬 |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| EP0930299A1 (en) * | 1996-08-19 | 1999-07-21 | Japan Tobacco Inc. | Propionic acid derivatives and applications thereof |
| DE69941777D1 (de) | 1998-03-10 | 2010-01-21 | Ono Pharmaceutical Co | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
| US6417212B1 (en) | 1999-08-27 | 2002-07-09 | Eli Lilly & Company | Modulators of peroxisome proliferator activated receptors |
| JP4316787B2 (ja) | 2000-01-11 | 2009-08-19 | 壽製薬株式会社 | エーテル又はアミド誘導体、その製法並びにそれを含有する糖尿病治療剤、 |
| US6982278B2 (en) | 2000-08-23 | 2006-01-03 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| EP1313717B1 (en) | 2000-08-23 | 2007-10-17 | Eli Lilly And Company | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
-
2001
- 2001-08-23 AT AT01963733T patent/ATE361283T1/de not_active IP Right Cessation
- 2001-08-23 PT PT01963733T patent/PT1313716E/pt unknown
- 2001-08-23 CZ CZ2003482A patent/CZ2003482A3/cs unknown
- 2001-08-23 JP JP2002521432A patent/JP2004506721A/ja not_active Withdrawn
- 2001-08-23 US US10/343,476 patent/US6930120B2/en not_active Expired - Fee Related
- 2001-08-23 CN CNA018177387A patent/CN1471517A/zh active Pending
- 2001-08-23 EP EP01963733A patent/EP1313716B1/en not_active Expired - Lifetime
- 2001-08-23 MX MXPA03001558A patent/MXPA03001558A/es unknown
- 2001-08-23 ES ES01963733T patent/ES2286137T3/es not_active Expired - Lifetime
- 2001-08-23 BR BR0113409-4A patent/BR0113409A/pt not_active IP Right Cessation
- 2001-08-23 AU AU2001284659A patent/AU2001284659A1/en not_active Abandoned
- 2001-08-23 IL IL15411001A patent/IL154110A0/xx unknown
- 2001-08-23 CA CA002418104A patent/CA2418104A1/en not_active Abandoned
- 2001-08-23 EA EA200300286A patent/EA200300286A1/ru unknown
- 2001-08-23 SK SK187-2003A patent/SK1872003A3/sk not_active Application Discontinuation
- 2001-08-23 WO PCT/US2001/022616 patent/WO2002016331A1/en not_active Ceased
- 2001-08-23 DK DK01963733T patent/DK1313716T3/da active
- 2001-08-23 KR KR10-2003-7002472A patent/KR20030027054A/ko not_active Withdrawn
- 2001-08-23 PL PL01360744A patent/PL360744A1/xx not_active Application Discontinuation
- 2001-08-23 HU HU0300857A patent/HUP0300857A3/hu unknown
- 2001-08-23 DE DE60128239T patent/DE60128239T2/de not_active Expired - Lifetime
- 2001-08-23 NZ NZ523804A patent/NZ523804A/en unknown
-
2003
- 2003-01-21 ZA ZA200300570A patent/ZA200300570B/en unknown
- 2003-02-14 NO NO20030729A patent/NO20030729L/no not_active Application Discontinuation
- 2003-03-06 EC EC2003004504A patent/ECSP034504A/es unknown
-
2005
- 2005-02-09 US US11/054,226 patent/US7345070B2/en not_active Expired - Fee Related
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2007
- 2007-06-19 CY CY20071100810T patent/CY1107679T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK1313716T3 (da) | 2007-08-27 |
| US6930120B2 (en) | 2005-08-16 |
| MXPA03001558A (es) | 2003-06-06 |
| AU2001284659A1 (en) | 2002-03-04 |
| JP2004506721A (ja) | 2004-03-04 |
| PL360744A1 (en) | 2004-09-20 |
| IL154110A0 (en) | 2003-07-31 |
| SK1872003A3 (en) | 2003-07-01 |
| ES2286137T3 (es) | 2007-12-01 |
| WO2002016331A1 (en) | 2002-02-28 |
| EA200300286A1 (ru) | 2003-08-28 |
| CN1471517A (zh) | 2004-01-28 |
| KR20030027054A (ko) | 2003-04-03 |
| US20050245584A1 (en) | 2005-11-03 |
| NO20030729D0 (no) | 2003-02-14 |
| DE60128239T2 (de) | 2008-01-10 |
| HUP0300857A3 (en) | 2007-03-28 |
| NO20030729L (no) | 2003-04-02 |
| ECSP034504A (es) | 2003-04-25 |
| BR0113409A (pt) | 2003-07-01 |
| US7345070B2 (en) | 2008-03-18 |
| ZA200300570B (en) | 2004-04-21 |
| DE60128239D1 (de) | 2007-06-14 |
| HUP0300857A2 (hu) | 2003-10-28 |
| EP1313716A1 (en) | 2003-05-28 |
| NZ523804A (en) | 2004-09-24 |
| ATE361283T1 (de) | 2007-05-15 |
| US20040097590A1 (en) | 2004-05-20 |
| CY1107679T1 (el) | 2013-04-18 |
| EP1313716B1 (en) | 2007-05-02 |
| PT1313716E (pt) | 2007-07-11 |
| CZ2003482A3 (cs) | 2003-05-14 |
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| EEER | Examination request | ||
| FZDE | Discontinued |