DE60208682T2 - Verfahren zur herstellung eines thiazol-ppar-liganden sowie dessen polymorphe - Google Patents
Verfahren zur herstellung eines thiazol-ppar-liganden sowie dessen polymorphe Download PDFInfo
- Publication number
- DE60208682T2 DE60208682T2 DE60208682T DE60208682T DE60208682T2 DE 60208682 T2 DE60208682 T2 DE 60208682T2 DE 60208682 T DE60208682 T DE 60208682T DE 60208682 T DE60208682 T DE 60208682T DE 60208682 T2 DE60208682 T2 DE 60208682T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- ppar
- compounds
- solution
- 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.)
- Expired - Fee Related
Links
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title abstract description 11
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title abstract description 11
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000003446 ligand Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 8
- 229940011051 isopropyl acetate Drugs 0.000 description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 5
- 230000002051 biphasic effect Effects 0.000 description 5
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 5
- IPRFNMJROWWFBH-UHFFFAOYSA-N 4-(trifluoromethyl)benzenecarbothioamide Chemical compound NC(=S)C1=CC=C(C(F)(F)F)C=C1 IPRFNMJROWWFBH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- BSVHTRRLCAVQCZ-JDEXMCKMSA-N (2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-2-[[(2s)-1-[(2s)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrro Chemical compound C([C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CC=C(O)C=C1 BSVHTRRLCAVQCZ-JDEXMCKMSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GBGYSMXMZDBILF-UHFFFAOYSA-N 2-(4-cyanophenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(C#N)C=C1 GBGYSMXMZDBILF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- ILUPZUOBHCUBKB-UHFFFAOYSA-N 2-methyl-2-(4-{[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}carbonyl)amino]methyl}phenoxy)propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C=C1 ILUPZUOBHCUBKB-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 102000016978 Orphan receptors Human genes 0.000 description 1
- 108070000031 Orphan receptors Proteins 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 108010077495 Peptide oostatic hormone Proteins 0.000 description 1
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 description 1
- 101710117029 Peroxisome proliferator-activated receptor delta Proteins 0.000 description 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 108010085012 Steroid Receptors Proteins 0.000 description 1
- 102000007451 Steroid Receptors Human genes 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002293 adipogenic effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000004322 lipid homeostasis Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 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
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 102000027483 retinoid hormone receptors Human genes 0.000 description 1
- 108091008679 retinoid hormone receptors Proteins 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C07D277/32—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- 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
- A61P9/10—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0113232.3A GB0113232D0 (en) | 2001-05-31 | 2001-05-31 | Chemical process |
| GB0113232 | 2001-05-31 | ||
| PCT/EP2002/005884 WO2002096893A1 (en) | 2001-05-31 | 2002-05-29 | Process for preparing a thialzole ppar-ligand and polymorphs thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60208682D1 DE60208682D1 (de) | 2006-04-06 |
| DE60208682T2 true DE60208682T2 (de) | 2006-08-24 |
Family
ID=9915637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60208682T Expired - Fee Related DE60208682T2 (de) | 2001-05-31 | 2002-05-29 | Verfahren zur herstellung eines thiazol-ppar-liganden sowie dessen polymorphe |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7244849B2 (enExample) |
| EP (1) | EP1395572B1 (enExample) |
| JP (1) | JP2004532265A (enExample) |
| KR (1) | KR20040007631A (enExample) |
| CN (1) | CN1551871A (enExample) |
| AT (1) | ATE315556T1 (enExample) |
| AU (1) | AU2002317764B2 (enExample) |
| BR (1) | BR0209892A (enExample) |
| CA (1) | CA2448101A1 (enExample) |
| CO (1) | CO5540298A2 (enExample) |
| CZ (1) | CZ20033256A3 (enExample) |
| DE (1) | DE60208682T2 (enExample) |
| ES (1) | ES2256493T3 (enExample) |
| GB (1) | GB0113232D0 (enExample) |
| HU (1) | HUP0400117A3 (enExample) |
| IL (1) | IL158641A0 (enExample) |
| MX (1) | MXPA03010943A (enExample) |
| NO (1) | NO20035313L (enExample) |
| NZ (1) | NZ529486A (enExample) |
| PL (1) | PL367114A1 (enExample) |
| WO (1) | WO2002096893A1 (enExample) |
| ZA (1) | ZA200308570B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7105551B2 (en) * | 2000-12-20 | 2006-09-12 | Smithkline Beecham Corporation | Thiazole derivatives for treating PPAR related disorders |
| BR0311834A (pt) | 2002-06-19 | 2005-04-12 | Lilly Co Eli | Composto, composição farmacêutica, métodos para mudular um receptor ativado por proliferador de peroxisoma, para tratar e prevenir diabetes mellitus em um mamìfero e para tratar sìndrome x em um mamìfero, e, uso de um composto ou seu sal farmaceuticamente aceitável |
| TW200400816A (en) | 2002-06-26 | 2004-01-16 | Lilly Co Eli | Tricyclic steroid hormone nuclear receptor modulators |
| US7553867B2 (en) | 2002-09-06 | 2009-06-30 | Takeda Pharmaceutical Company Limited | Furan or thiophene derivative and medicinal use thereof |
| EP1680131A4 (en) | 2003-08-01 | 2009-05-27 | Janssen Pharmaceutica Nv | SUBSTITUTED INDOLE-O-GLUCOSIDES |
| EP1734930A2 (en) * | 2004-04-09 | 2006-12-27 | Smithkline Beecham Corporation | Low dose pharmaceutical products |
| JP2009523132A (ja) * | 2006-01-10 | 2009-06-18 | スミスクライン ビーチャム コーポレーション | ｛２−メチル−４−［４−メチル−２−（４−トリフルオロメチルフェニル）チアゾール−５−イルメチルチオ］フェノキシ｝−酢酸の多形体形態 |
| WO2012168948A2 (en) * | 2011-06-06 | 2012-12-13 | Hetero Research Foundation | Process for febuxostat |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100620337B1 (ko) * | 1998-03-10 | 2006-09-13 | 오노 야꾸힝 고교 가부시키가이샤 | 카르복실산 유도체와 그 유도체를 유효 성분으로서함유하는 약제 |
| PE20011010A1 (es) * | 1999-12-02 | 2001-10-18 | Glaxo Group Ltd | Oxazoles y tiazoles sustituidos como agonista del receptor activado por el proliferador de peroxisomas humano |
| AU2002233271A1 (en) * | 2000-12-20 | 2002-07-01 | Glaxo Group Limited | Substitued oxazoles and thiazoles as hppar alpha agonists |
| GB0111523D0 (en) * | 2001-05-11 | 2001-07-04 | Glaxo Group Ltd | Chemical compounds |
| GB0113233D0 (en) * | 2001-05-31 | 2001-07-25 | Glaxo Group Ltd | Chemical compounds |
-
2001
- 2001-05-31 GB GBGB0113232.3A patent/GB0113232D0/en not_active Ceased
-
2002
- 2002-05-29 AU AU2002317764A patent/AU2002317764B2/en not_active Ceased
- 2002-05-29 ES ES02747330T patent/ES2256493T3/es not_active Expired - Lifetime
- 2002-05-29 US US10/478,260 patent/US7244849B2/en not_active Expired - Fee Related
- 2002-05-29 CZ CZ20033256A patent/CZ20033256A3/cs unknown
- 2002-05-29 KR KR10-2003-7015677A patent/KR20040007631A/ko not_active Ceased
- 2002-05-29 BR BR0209892-0A patent/BR0209892A/pt not_active IP Right Cessation
- 2002-05-29 HU HU0400117A patent/HUP0400117A3/hu unknown
- 2002-05-29 CA CA002448101A patent/CA2448101A1/en not_active Abandoned
- 2002-05-29 AT AT02747330T patent/ATE315556T1/de not_active IP Right Cessation
- 2002-05-29 PL PL02367114A patent/PL367114A1/xx not_active Application Discontinuation
- 2002-05-29 IL IL15864102A patent/IL158641A0/xx unknown
- 2002-05-29 JP JP2003500072A patent/JP2004532265A/ja active Pending
- 2002-05-29 DE DE60208682T patent/DE60208682T2/de not_active Expired - Fee Related
- 2002-05-29 MX MXPA03010943A patent/MXPA03010943A/es unknown
- 2002-05-29 NZ NZ529486A patent/NZ529486A/en unknown
- 2002-05-29 WO PCT/EP2002/005884 patent/WO2002096893A1/en not_active Ceased
- 2002-05-29 EP EP02747330A patent/EP1395572B1/en not_active Expired - Lifetime
- 2002-05-29 CN CNA02810885XA patent/CN1551871A/zh active Pending
-
2003
- 2003-11-03 ZA ZA200308570A patent/ZA200308570B/en unknown
- 2003-11-26 CO CO03104438A patent/CO5540298A2/es not_active Application Discontinuation
- 2003-11-28 NO NO20035313A patent/NO20035313L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040007631A (ko) | 2004-01-24 |
| NO20035313D0 (no) | 2003-11-28 |
| CO5540298A2 (es) | 2005-07-29 |
| BR0209892A (pt) | 2004-06-08 |
| CA2448101A1 (en) | 2002-12-05 |
| HUP0400117A3 (en) | 2005-09-28 |
| US7244849B2 (en) | 2007-07-17 |
| CZ20033256A3 (en) | 2004-04-14 |
| EP1395572B1 (en) | 2006-01-11 |
| US20040242657A1 (en) | 2004-12-02 |
| ES2256493T3 (es) | 2006-07-16 |
| AU2002317764B2 (en) | 2005-01-06 |
| JP2004532265A (ja) | 2004-10-21 |
| WO2002096893A1 (en) | 2002-12-05 |
| HUP0400117A2 (hu) | 2005-03-29 |
| PL367114A1 (en) | 2005-02-21 |
| MXPA03010943A (es) | 2004-02-27 |
| NO20035313L (no) | 2003-12-09 |
| ATE315556T1 (de) | 2006-02-15 |
| CN1551871A (zh) | 2004-12-01 |
| EP1395572A1 (en) | 2004-03-10 |
| GB0113232D0 (en) | 2001-07-25 |
| DE60208682D1 (de) | 2006-04-06 |
| ZA200308570B (en) | 2005-02-03 |
| NZ529486A (en) | 2005-12-23 |
| IL158641A0 (en) | 2004-05-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60010333T2 (de) | Substituierte oxazole und thiazole derivate als hppar-alpha aktivatore | |
| CH635578A5 (en) | Process for preparing novel 5-(subst. phenyl)-oxazolidinones and their sulphur analogs | |
| DE60127845T2 (de) | Benzylidenthiazolidindione und ihre verwendung als antimykotische mittel | |
| DE69201748T2 (de) | Pyrazinderivate. | |
| EP0041215B1 (de) | Imidazoazolalkensäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln | |
| CZ323094A3 (en) | Branched amino derivatives of thiazole, process of their preparation and pharmaceutical compositions containing thereof | |
| DE60208682T2 (de) | Verfahren zur herstellung eines thiazol-ppar-liganden sowie dessen polymorphe | |
| DE69728180T2 (de) | Verfahren zur herstellung von carbamoylsubstituierten imidazolderivaten | |
| DE69825880T2 (de) | Verfahren zur herstellung von eprosartan | |
| DE2119730B2 (de) | Verfahren zur herstellung von 1,2-benzisothiazolin-3-onen | |
| EP0305593A2 (de) | Neue Zwischenprodukte für 2-Pyridinyloxyphenoxypropionsäure-cyanamide | |
| EP0471262B1 (de) | Verfahren zur Herstellung von substituierten 3-Aminoacrylestern | |
| DE2733181A1 (de) | Verfahren zur herstellung von n-substituierten alpha-ketocarbonsaeureamiden | |
| DE2441201A1 (de) | Anthelminthisch wirksame 2-carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und verfahren zu ihrer herstellung | |
| EP0293742B1 (de) | Verfahren zur Herstellung von 4-Nitro-5-imidazolylethern und -thioethern | |
| DE1543612A1 (de) | Verfahren zur Herstellung von Alkylmercaptoaniliden | |
| DE2364474C3 (de) | Verfahren zur Herstellung von 4-Aminol,2,4-triazin-5-onen | |
| DE3879650T2 (de) | N-acyl-n-naphthoylglycine als aldose-reductase-inhibitoren. | |
| DE2747122A1 (de) | Derivate von 6-(m-aminophenyl)-2, 3,5,6-tetrahydroimidazo eckige klammer auf 2,1-b eckige klammer zu -thiazol, verfahren zu ihrer herstellung und ihre verwendung | |
| DE1918070A1 (de) | Neue,an der Aminogruppe substituierte 2-Amino-5-nitro-thiazole und Verfahren zur Herstellung | |
| DE1695067B1 (de) | Verfahren zur Herstellung von 5-Cyanuracilen | |
| DE2728870C2 (de) | Verfahren zur Herstellung von D-Penicillamin und dessen Salzen | |
| DE1695909C3 (de) | Verfahren zur Herstellung von 1-(5-Nitro-2-thiazolyl)-2-oxo-imidazolidinen | |
| DE947970C (de) | Verfahren zur Herstellung von 2, 5-Diphenyl-thiodiazol-(1,3,4) und seinen im Phenylrest substituierten Abkoemmlingen | |
| EP0050225A1 (de) | Neue Sulfone, deren Herstellung und Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |