ZA200100983B - Substituted oxazoles and thiazoles derivatives as hPPAR gamma and hPPAR alpha activators. - Google Patents
Substituted oxazoles and thiazoles derivatives as hPPAR gamma and hPPAR alpha activators. Download PDFInfo
- Publication number
- ZA200100983B ZA200100983B ZA200100983A ZA200100983A ZA200100983B ZA 200100983 B ZA200100983 B ZA 200100983B ZA 200100983 A ZA200100983 A ZA 200100983A ZA 200100983 A ZA200100983 A ZA 200100983A ZA 200100983 B ZA200100983 B ZA 200100983B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- methyl
- propanoic acid
- oxazol
- oxo
- Prior art date
Links
- 239000012190 activator Substances 0.000 title claims description 5
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 title description 4
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 title description 4
- 150000002916 oxazoles Chemical class 0.000 title description 2
- 150000003557 thiazoles Chemical class 0.000 title description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 120
- 235000019260 propionic acid Nutrition 0.000 claims description 119
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 150000002367 halogens Chemical class 0.000 claims description 55
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 43
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- -1 {(Z)-1-methyl-3-oxo-3-[4-(trifluoromethyl)phenyl]-1-propenyl}amino Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 7
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 206010070901 Diabetic dyslipidaemia Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 9
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 239000000126 substance Substances 0.000 claims 6
- DQXNSYWZITXZIQ-IOBJKCMUSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]phenyl]-2-[[(z)-4-oxo-4-[4-(trifluoromethyl)phenyl]but-2-en-2-yl]amino]propanoic acid Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(S1)C)N=C1C1=CC=CC=C1 DQXNSYWZITXZIQ-IOBJKCMUSA-N 0.000 claims 1
- ADFCHMHRJJUJOS-GDZDTEGPSA-N (2s)-3-[4-[2-[2-(4-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[[(z)-1-oxo-1-[4-(trifluoromethyl)phenyl]pent-2-en-3-yl]amino]propanoic acid Chemical compound C([C@H](NC(/CC)=C\C(=O)C=1C=CC(=CC=1)C(F)(F)F)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(OC)C=C1 ADFCHMHRJJUJOS-GDZDTEGPSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000009977 dual effect Effects 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 230000000694 effects Effects 0.000 description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 229940123464 Thiazolidinedione Drugs 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 150000001467 thiazolidinediones Chemical class 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 208000002705 Glucose Intolerance Diseases 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229940125542 dual agonist Drugs 0.000 description 2
- 229940125753 fibrate Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 150000003626 triacylglycerols Chemical class 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
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- 101100168093 Caenorhabditis elegans cogc-2 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 108090001060 Lipase Proteins 0.000 description 1
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- 241000124008 Mammalia Species 0.000 description 1
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- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
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- 101150023417 PPARG gene Proteins 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
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- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 206010060755 Type V hyperlipidaemia Diseases 0.000 description 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
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- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 230000000923 atherogenic effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
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- 208000035475 disorder Diseases 0.000 description 1
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- 230000004136 fatty acid synthesis Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
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- 230000035897 transcription Effects 0.000 description 1
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- 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
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
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
- C07D413/12—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
-
- 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
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
-
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (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)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9817118.4A GB9817118D0 (en) | 1998-08-07 | 1998-08-07 | Pharmaceutical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200100983B true ZA200100983B (en) | 2002-03-05 |
Family
ID=10836805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200100983A ZA200100983B (en) | 1998-08-07 | 2001-02-05 | Substituted oxazoles and thiazoles derivatives as hPPAR gamma and hPPAR alpha activators. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6498174B1 (es) |
| EP (1) | EP1102757B1 (es) |
| JP (1) | JP2002522426A (es) |
| KR (1) | KR20010085340A (es) |
| CN (1) | CN1321152A (es) |
| AP (1) | AP2001002066A0 (es) |
| AR (1) | AR020001A1 (es) |
| AT (1) | ATE264313T1 (es) |
| AU (1) | AU5731099A (es) |
| BR (1) | BR9912866A (es) |
| CA (1) | CA2339773A1 (es) |
| CO (1) | CO5070570A1 (es) |
| CZ (1) | CZ2001490A3 (es) |
| DE (1) | DE69916457T2 (es) |
| EA (1) | EA200100105A1 (es) |
| EE (1) | EE200100074A (es) |
| ES (1) | ES2220110T3 (es) |
| GB (1) | GB9817118D0 (es) |
| HR (1) | HRP20010095A2 (es) |
| HU (1) | HUP0103469A3 (es) |
| ID (1) | ID29543A (es) |
| IL (1) | IL141248A0 (es) |
| IS (1) | IS5840A (es) |
| MA (1) | MA26668A1 (es) |
| NO (1) | NO20010628L (es) |
| PE (1) | PE20000947A1 (es) |
| PL (1) | PL345882A1 (es) |
| SK (1) | SK1962001A3 (es) |
| TR (1) | TR200100372T2 (es) |
| WO (1) | WO2000008002A1 (es) |
| ZA (1) | ZA200100983B (es) |
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| ES2204684T3 (es) * | 1999-08-27 | 2004-05-01 | Eli Lilly And Company | Derivados de biaril-oxa(tia)zol y su uso como modulares de ppar. |
| EP1939188A1 (en) * | 1999-09-22 | 2008-07-02 | Bristol-Myers Squibb Company | Oxa-and thiazole derivatives useful as antidiabetic and antiobesity agents |
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| US6414002B1 (en) | 1999-09-22 | 2002-07-02 | Bristol-Myers Squibb Company | Substituted acid derivatives useful as antidiabetic and antiobesity agents and method |
| GB0002667D0 (en) * | 2000-02-04 | 2000-03-29 | Glaxo Group Ltd | medicamesnts |
| US20040072838A1 (en) | 2000-12-20 | 2004-04-15 | Pierette Banker | Thiazole and oxazole derivatives as activators of human peroxisome proliferator activated receptors |
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| EP1394154A4 (en) | 2001-03-23 | 2005-05-18 | Takeda Pharmaceutical | HETEROCYCLIC DERIVATIVE WITH FIVE MEMBERS OF ALKANOIC ACID |
| GB0111523D0 (en) | 2001-05-11 | 2001-07-04 | Glaxo Group Ltd | Chemical compounds |
| MXPA03010435A (es) | 2001-05-15 | 2004-03-09 | Hoffmann La Roche | Derivados de oxazol acido carboxilico sustituidos para uso como activadores de proliferacion del peroximosa(ppar-alfa y gama) en el tratamiento de diabetes. |
| WO2002096880A1 (fr) * | 2001-05-29 | 2002-12-05 | Kyoto Pharmaceutical Industries, Ltd. | Nouveau compose heterocyclique et son utilisation medicinale |
| KR100874677B1 (ko) | 2001-05-29 | 2008-12-18 | 교토 야쿠힝 고교 가부시키가이샤 | 신규 복소환 유도체 및 그 의약 용도 |
| US6861440B2 (en) | 2001-10-26 | 2005-03-01 | Hoffmann-La Roche Inc. | DPP IV inhibitors |
| TW200300681A (en) * | 2001-11-12 | 2003-06-16 | Ono Pharmaceutical Co | Carboxylic acid derivative compound and medicament containing same as active ingredient |
| JP3884736B2 (ja) | 2002-01-17 | 2007-02-21 | トーアエイヨー株式会社 | ハロゲノベンジルアミノプロピオン酸誘導体 |
| US6716842B2 (en) | 2002-04-05 | 2004-04-06 | Warner-Lambert Company, Llc | Antidiabetic agents |
| US20050119314A1 (en) * | 2002-04-05 | 2005-06-02 | Sankyo Company, Limited | Pharmaceutical composition comprising an ACAT inhibitor and an insulin resistance reducing agent |
| KR100474202B1 (ko) * | 2002-05-04 | 2005-03-08 | 강헌중 | 티아졸 유도체의 제조방법 및 이를 제조하기 위한 중간체 |
| RU2295520C2 (ru) | 2002-07-03 | 2007-03-20 | Ф.Хоффманн-Ля Рош Аг | ПРОИЗВОДНЫЕ ОКСАЗОЛА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ СЕНСИБИЛИЗАТОРОВ ИНСУЛИНА, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, ОБЛАДАЮЩАЯ АКТИВИРУЮЩИМ ДЕЙСТВИЕМ В ОТНОШЕНИИ PRARα И/ИЛИ PRARγ |
| PL374860A1 (en) | 2002-07-09 | 2005-11-14 | Bristol-Myers Squibb Company | Substituted heterocyclic derivatives useful as antidiabetic and antiobesity agents and method |
| DE60334461D1 (de) * | 2002-08-30 | 2010-11-18 | Hoffmann La Roche | Neue 2-arylthiazolverbindungen als ppar-alpha und -gamma agonisten |
| KR100645684B1 (ko) | 2002-09-12 | 2006-11-15 | 에프. 호프만-라 로슈 아게 | 당뇨병 치료에 유용한 ｐｐａｒ 작동제로서 ｎ-치환된-1ｈ-인돌-5-프로파이온산 화합물 |
| AR041481A1 (es) * | 2002-10-07 | 2005-05-18 | Hoffmann La Roche | Derivados de acido arilpropionico-oxazol y su uso como agonistas de ppar |
| EP1567523B1 (en) | 2002-11-25 | 2008-08-20 | F.Hoffmann-La Roche Ag | Indolyl derivatives |
| US7192970B2 (en) | 2002-11-26 | 2007-03-20 | Chipscreen Biosciences, Ltd. | Noncyclic 1,3-dicarbonyl compounds as dual PPAR agonists with potent antihyperglycemic and antihyperlipidemic activity |
| US7268157B2 (en) * | 2002-11-26 | 2007-09-11 | Shenzhen Chipscreen Biosciences, Ltd. | Substituted arylalcanoic acid derivatives as PPAR pan agonists with potent antihyperglycemic and antihyperlipidemic activity |
| KR100744893B1 (ko) | 2003-06-20 | 2007-08-01 | 에프. 호프만-라 로슈 아게 | Ｄｐｐ-ｉｖ 저해제로서 헥사하이드로피리도아이소퀴놀린 |
| ATE489387T1 (de) | 2003-06-20 | 2010-12-15 | Hoffmann La Roche | Pyridoä2,1-aü-isochinolinderivate als dpp-iv inhibitoren |
| UA85711C2 (ru) | 2004-05-06 | 2009-02-25 | Зе Регентс Оф Зе Юниверсити Оф Калифорния | Замещенные енаминоны, их производные и их применение |
| CN100344618C (zh) | 2004-05-24 | 2007-10-24 | 北京摩力克科技有限公司 | 作为hPPARα和hPPARγ激动剂的N－芳丙烯酰基取代的酪氨酸衍生物 |
| CN100467456C (zh) * | 2004-05-24 | 2009-03-11 | 北京摩力克科技有限公司 | 作为hPPARα和/或hPPARγ激活剂的α-哌嗪取代的苯丙酸衍生物 |
| CN100436430C (zh) * | 2004-05-24 | 2008-11-26 | 北京摩力克科技有限公司 | 作为hPPARα和hPPARγ激动剂的烷酰基取代的酪氨酸衍生物 |
| CN1896069B (zh) * | 2005-07-15 | 2011-10-05 | 中国科学院上海药物研究所 | 一类取代噻唑-4酮化合物、制备方法和用途 |
| CN101007790B (zh) * | 2006-01-27 | 2011-03-30 | 北京摩力克科技有限公司 | 草氨酸衍生物、其制备方法和医药用途 |
| WO2007147336A1 (en) * | 2006-06-13 | 2007-12-27 | Shanghai Institue Of Materia Medica, Chinese Academy Of Sciences | Heterocyclic non-nucleoside compounds, their peparation, pharmaceutical composition and their use as antiviral agents |
| GB0719180D0 (en) * | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
| EP2135865A1 (de) | 2008-06-17 | 2009-12-23 | Bayer CropScience AG | Substituierte 1-(Diazinyl) pyrazol-4-yl-essigsäuren, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP2194052A1 (de) | 2008-12-06 | 2010-06-09 | Bayer CropScience AG | Substituierte 1-(Thiazolyl)- und 1-(Isothiazolyl)pyrazol-4-yl-essigsäuren, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| WO2011073098A1 (de) | 2009-12-15 | 2011-06-23 | Bayer Cropscience Ag | 1-(heteroaryl)-pyrazol-4-yl-essigsäuren, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren |
| US20120094959A1 (en) | 2010-10-19 | 2012-04-19 | Bonnie Blazer-Yost | Treatment of cystic diseases |
| CN116367861A (zh) * | 2020-09-14 | 2023-06-30 | 上海弼领生物技术有限公司 | PPARα（过氧化物酶体增殖物激活受体α）配体在制备药物中的应用 |
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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 |
| US6062509A (en) | 1994-12-23 | 2000-05-16 | Hexcel Corporation | Retrofit centerline luggage bin assemblies compatible with existing aircraft bin supports |
| JPH08325263A (ja) | 1995-05-31 | 1996-12-10 | Sumitomo Metal Ind Ltd | 新規２−アミノ−３−フェニルプロピオン酸誘導体 |
| GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| KR20000068151A (ko) * | 1996-08-19 | 2000-11-25 | 미즈노 마사루 | 프로피온산 유도체 및 그의 용도 |
-
1998
- 1998-08-07 GB GBGB9817118.4A patent/GB9817118D0/en not_active Ceased
-
1999
- 1999-08-04 CO CO99049333A patent/CO5070570A1/es unknown
- 1999-08-04 AR ARP990103874A patent/AR020001A1/es not_active Application Discontinuation
- 1999-08-05 IL IL14124899A patent/IL141248A0/xx unknown
- 1999-08-05 KR KR1020017001617A patent/KR20010085340A/ko not_active Application Discontinuation
- 1999-08-05 JP JP2000563635A patent/JP2002522426A/ja active Pending
- 1999-08-05 EE EEP200100074A patent/EE200100074A/xx unknown
- 1999-08-05 PE PE1999000790A patent/PE20000947A1/es not_active Application Discontinuation
- 1999-08-05 DE DE69916457T patent/DE69916457T2/de not_active Expired - Lifetime
- 1999-08-05 ES ES99944335T patent/ES2220110T3/es not_active Expired - Lifetime
- 1999-08-05 CN CN99811640A patent/CN1321152A/zh active Pending
- 1999-08-05 EP EP99944335A patent/EP1102757B1/en not_active Expired - Lifetime
- 1999-08-05 EA EA200100105A patent/EA200100105A1/ru unknown
- 1999-08-05 AP APAP/P/2001/002066A patent/AP2001002066A0/en unknown
- 1999-08-05 WO PCT/EP1999/005666 patent/WO2000008002A1/en not_active Application Discontinuation
- 1999-08-05 BR BR9912866-7A patent/BR9912866A/pt not_active Application Discontinuation
- 1999-08-05 AU AU57310/99A patent/AU5731099A/en not_active Abandoned
- 1999-08-05 ID IDW20010541A patent/ID29543A/id unknown
- 1999-08-05 AT AT99944335T patent/ATE264313T1/de not_active IP Right Cessation
- 1999-08-05 CZ CZ2001490A patent/CZ2001490A3/cs unknown
- 1999-08-05 TR TR2001/00372T patent/TR200100372T2/xx unknown
- 1999-08-05 HU HU0103469A patent/HUP0103469A3/hu unknown
- 1999-08-05 US US09/762,445 patent/US6498174B1/en not_active Expired - Fee Related
- 1999-08-05 MA MA25716A patent/MA26668A1/fr unknown
- 1999-08-05 SK SK196-2001A patent/SK1962001A3/sk unknown
- 1999-08-05 PL PL99345882A patent/PL345882A1/xx not_active Application Discontinuation
- 1999-08-05 CA CA002339773A patent/CA2339773A1/en not_active Abandoned
-
2001
- 2001-02-05 IS IS5840A patent/IS5840A/is unknown
- 2001-02-05 ZA ZA200100983A patent/ZA200100983B/en unknown
- 2001-02-06 NO NO20010628A patent/NO20010628L/no not_active Application Discontinuation
- 2001-02-07 HR HR20010095A patent/HRP20010095A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PE20000947A1 (es) | 2000-09-22 |
| ATE264313T1 (de) | 2004-04-15 |
| GB9817118D0 (en) | 1998-10-07 |
| SK1962001A3 (en) | 2001-11-06 |
| TR200100372T2 (tr) | 2001-09-21 |
| DE69916457D1 (de) | 2004-05-19 |
| CA2339773A1 (en) | 2000-02-17 |
| EE200100074A (et) | 2002-06-17 |
| AP2001002066A0 (en) | 2001-03-31 |
| AR020001A1 (es) | 2002-03-27 |
| IS5840A (is) | 2001-02-05 |
| PL345882A1 (en) | 2002-01-14 |
| HUP0103469A3 (en) | 2002-08-28 |
| NO20010628L (no) | 2001-04-06 |
| IL141248A0 (en) | 2002-03-10 |
| ES2220110T3 (es) | 2004-12-01 |
| JP2002522426A (ja) | 2002-07-23 |
| KR20010085340A (ko) | 2001-09-07 |
| HUP0103469A2 (hu) | 2002-01-28 |
| NO20010628D0 (no) | 2001-02-06 |
| CZ2001490A3 (cs) | 2001-08-15 |
| EP1102757A1 (en) | 2001-05-30 |
| DE69916457T2 (de) | 2005-04-14 |
| EP1102757B1 (en) | 2004-04-14 |
| US6498174B1 (en) | 2002-12-24 |
| ID29543A (id) | 2001-09-06 |
| BR9912866A (pt) | 2001-10-30 |
| MA26668A1 (fr) | 2004-12-20 |
| CN1321152A (zh) | 2001-11-07 |
| HRP20010095A2 (en) | 2002-02-28 |
| CO5070570A1 (es) | 2001-08-28 |
| WO2000008002A1 (en) | 2000-02-17 |
| EA200100105A1 (ru) | 2001-08-27 |
| AU5731099A (en) | 2000-02-28 |
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