NO321872B1 - Tiazol- og oksazolderivater, samt anvendelse derav og farmasoytisk preparat. - Google Patents
Tiazol- og oksazolderivater, samt anvendelse derav og farmasoytisk preparat. Download PDFInfo
- Publication number
- NO321872B1 NO321872B1 NO20016078A NO20016078A NO321872B1 NO 321872 B1 NO321872 B1 NO 321872B1 NO 20016078 A NO20016078 A NO 20016078A NO 20016078 A NO20016078 A NO 20016078A NO 321872 B1 NO321872 B1 NO 321872B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- phenyl
- trifluoromethyl
- thiazol
- sulfanyl
- Prior art date
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- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
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- ISRINYSAVKOINR-CSKARUKUSA-N methyl (e)-3-[3-methoxy-4-[[4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]phenyl]prop-2-enoate Chemical compound COC1=CC(/C=C/C(=O)OC)=CC=C1OCC1=C(C)N=C(C=2C=C(C=CC=2)C(F)(F)F)S1 ISRINYSAVKOINR-CSKARUKUSA-N 0.000 description 1
- OTWKBNMPICRZQQ-LFYBBSHMSA-N methyl (e)-3-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]methoxy]phenyl]prop-2-enoate Chemical compound C1=CC(/C=C/C(=O)OC)=CC=C1OCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)O1 OTWKBNMPICRZQQ-LFYBBSHMSA-N 0.000 description 1
- JJJSFAGPWHEUBT-UHFFFAOYSA-N methyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(OC)=C1 JJJSFAGPWHEUBT-UHFFFAOYSA-N 0.000 description 1
- DKLZRLRMFNWRFB-UHFFFAOYSA-N methyl 2-(4-hydroxyanilino)acetate Chemical compound COC(=O)CNC1=CC=C(O)C=C1 DKLZRLRMFNWRFB-UHFFFAOYSA-N 0.000 description 1
- DCSBCLDLEBBYAH-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)sulfanylacetate Chemical compound COC(=O)CSC1=CC=C(O)C=C1 DCSBCLDLEBBYAH-UHFFFAOYSA-N 0.000 description 1
- WKKORULHEAYTIF-UHFFFAOYSA-N methyl 2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]methylsulfanyl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)O1 WKKORULHEAYTIF-UHFFFAOYSA-N 0.000 description 1
- BIBBTZDLGZDWHG-UHFFFAOYSA-N methyl 2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1OCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 BIBBTZDLGZDWHG-UHFFFAOYSA-N 0.000 description 1
- QODOIZHAPCCMJN-UHFFFAOYSA-N methyl 2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 QODOIZHAPCCMJN-UHFFFAOYSA-N 0.000 description 1
- BDRKCQMYMBYQCC-UHFFFAOYSA-N methyl 2-[3-chloro-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]methoxy]phenyl]acetate Chemical compound ClC1=CC(CC(=O)OC)=CC=C1OCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)O1 BDRKCQMYMBYQCC-UHFFFAOYSA-N 0.000 description 1
- ILHKSQRFSMXNKA-UHFFFAOYSA-N methyl 2-[3-chloro-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]acetate Chemical compound ClC1=CC(CC(=O)OC)=CC=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 ILHKSQRFSMXNKA-UHFFFAOYSA-N 0.000 description 1
- MNUZKVAAUBRAOW-UHFFFAOYSA-N methyl 2-[3-methoxy-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]acetate Chemical compound COC1=CC(CC(=O)OC)=CC=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 MNUZKVAAUBRAOW-UHFFFAOYSA-N 0.000 description 1
- BUWRBLWTDVOLII-UHFFFAOYSA-N methyl 2-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]methylsulfanyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)O1 BUWRBLWTDVOLII-UHFFFAOYSA-N 0.000 description 1
- IUCKBHRNVNQOMO-UHFFFAOYSA-N methyl 2-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 IUCKBHRNVNQOMO-UHFFFAOYSA-N 0.000 description 1
- RDTDBZNJPPQLDV-UHFFFAOYSA-N methyl 2-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 RDTDBZNJPPQLDV-UHFFFAOYSA-N 0.000 description 1
- PDTCYIZPTRRYOT-UHFFFAOYSA-N methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(O)C(OC)=C1 PDTCYIZPTRRYOT-UHFFFAOYSA-N 0.000 description 1
- OBLIYYKVAGNUHN-UHFFFAOYSA-N methyl 3-[3-methoxy-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]phenyl]propanoate Chemical compound COC1=CC(CCC(=O)OC)=CC=C1OCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 OBLIYYKVAGNUHN-UHFFFAOYSA-N 0.000 description 1
- ROHPLQNLWCRYAQ-UHFFFAOYSA-N methyl 3-[4-[2-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1OCCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 ROHPLQNLWCRYAQ-UHFFFAOYSA-N 0.000 description 1
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- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000003893 regulation of appetite Effects 0.000 description 1
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- 230000028327 secretion Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 108091008012 small dense LDL Proteins 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
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- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- AUJXJFHANFIVKH-GQCTYLIASA-N trans-methylferulate Chemical compound COC(=O)\C=C\C1=CC=C(O)C(OC)=C1 AUJXJFHANFIVKH-GQCTYLIASA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 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
- 229960001641 troglitazone Drugs 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
- 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
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- 239000000080 wetting agent Substances 0.000 description 1
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Classifications
-
- 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
- C07D277/26—Radicals substituted by sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- 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
- 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
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9914977.5A GB9914977D0 (en) | 1999-06-25 | 1999-06-25 | Chemical compounds |
| PCT/EP2000/005720 WO2001000603A1 (en) | 1999-06-25 | 2000-06-22 | Thiazole and oxazole derivatives and their pharmaceutical use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20016078L NO20016078L (no) | 2001-12-13 |
| NO20016078D0 NO20016078D0 (no) | 2001-12-13 |
| NO321872B1 true NO321872B1 (no) | 2006-07-17 |
Family
ID=10856125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20016078A NO321872B1 (no) | 1999-06-25 | 2001-12-13 | Tiazol- og oksazolderivater, samt anvendelse derav og farmasoytisk preparat. |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6710063B1 (cs) |
| EP (1) | EP1189895B8 (cs) |
| JP (2) | JP3490704B2 (cs) |
| KR (1) | KR100668026B1 (cs) |
| CN (1) | CN1164579C (cs) |
| AR (1) | AR035320A1 (cs) |
| AT (1) | ATE297384T1 (cs) |
| AU (1) | AU765347B2 (cs) |
| BR (1) | BR0011891A (cs) |
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