CA2479274C - Thiazolidinedione derivatives and pharmaceutical composition comprising the same - Google Patents
Thiazolidinedione derivatives and pharmaceutical composition comprising the same Download PDFInfo
- Publication number
- CA2479274C CA2479274C CA2479274A CA2479274A CA2479274C CA 2479274 C CA2479274 C CA 2479274C CA 2479274 A CA2479274 A CA 2479274A CA 2479274 A CA2479274 A CA 2479274A CA 2479274 C CA2479274 C CA 2479274C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- amino
- ethoxy
- thiazolidinedione
- phenoxy
- 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 - Lifetime
Links
- 150000001467 thiazolidinediones Chemical class 0.000 title claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 149
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 124
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 118
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 102
- 125000004076 pyridyl group Chemical group 0.000 claims description 45
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
- 239000008280 blood Substances 0.000 claims description 19
- 210000004369 blood Anatomy 0.000 claims description 19
- 206010012601 diabetes mellitus Diseases 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 4
- CXBDFTRFZWXPCP-UHFFFAOYSA-N 5-[[4-[2-[[2-(4-aminophenyl)pyridin-3-yl]-methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CN=C(C=2C=CC(N)=CC=2)C=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O CXBDFTRFZWXPCP-UHFFFAOYSA-N 0.000 claims description 3
- RXOMMCZPEYMATH-UHFFFAOYSA-N 5-[[4-[2-[[2-(4-aminophenyl)pyridin-3-yl]-methylamino]ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CN=C(C=2C=CC(N)=CC=2)C=1N(C)CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O RXOMMCZPEYMATH-UHFFFAOYSA-N 0.000 claims description 3
- CZDIIWPOXLTRFV-UHFFFAOYSA-N 5-[[4-[2-[[4-(4-aminophenyl)pyrimidin-2-yl]-methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C=CC(C=2C=CC(N)=CC=2)=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O CZDIIWPOXLTRFV-UHFFFAOYSA-N 0.000 claims description 3
- CSDIEQDNZJIDST-UHFFFAOYSA-N 5-[[4-[2-[[4-(4-aminophenyl)pyrimidin-2-yl]-methylamino]ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound N=1C=CC(C=2C=CC(N)=CC=2)=NC=1N(C)CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O CSDIEQDNZJIDST-UHFFFAOYSA-N 0.000 claims description 3
- ZPVXPCRSNDOUJI-UHFFFAOYSA-N 5-[[4-[2-[methyl-(2-thiophen-3-yloxypyridin-3-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CN=C(OC2=CSC=C2)C=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O ZPVXPCRSNDOUJI-UHFFFAOYSA-N 0.000 claims description 3
- REIYLXDQWQVUQG-UHFFFAOYSA-N 5-[[4-[2-[methyl-(4-thiophen-3-yloxypyrimidin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C=CC(OC2=CSC=C2)=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O REIYLXDQWQVUQG-UHFFFAOYSA-N 0.000 claims description 3
- WTIDJWPEDOETIE-UHFFFAOYSA-N C=1C=CN=C(OC2=CSC=C2)C=1N(C)CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O Chemical compound C=1C=CN=C(OC2=CSC=C2)C=1N(C)CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O WTIDJWPEDOETIE-UHFFFAOYSA-N 0.000 claims description 3
- DVCCOSRHEFCTAL-UHFFFAOYSA-N N=1C=CC(OC2=CSC=C2)=NC=1N(C)CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O Chemical compound N=1C=CC(OC2=CSC=C2)=NC=1N(C)CCOC(C=C1)=CC=C1C=C1SC(=O)NC1=O DVCCOSRHEFCTAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 196
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 12
- 125000003118 aryl group Chemical group 0.000 abstract description 12
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 abstract description 9
- 229910052736 halogen Inorganic materials 0.000 abstract description 7
- 150000002367 halogens Chemical class 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 description 126
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 111
- 238000000034 method Methods 0.000 description 92
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 80
- 238000005160 1H NMR spectroscopy Methods 0.000 description 75
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 56
- 101150041968 CDC13 gene Proteins 0.000 description 54
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 38
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 17
- 229960004586 rosiglitazone Drugs 0.000 description 16
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 14
- 229940123464 Thiazolidinedione Drugs 0.000 description 13
- 229940093499 ethyl acetate Drugs 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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 8
- -1 is not found Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- QOKNQKPGYNQUPP-UHFFFAOYSA-N 4-chloro-2-phenoxypyrimidine Chemical compound ClC1=CC=NC(OC=2C=CC=CC=2)=N1 QOKNQKPGYNQUPP-UHFFFAOYSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 6
- 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 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
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- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
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- 239000004480 active ingredient Substances 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
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- 125000005843 halogen group Chemical group 0.000 description 5
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- 235000019341 magnesium sulphate Nutrition 0.000 description 5
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
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- DTWGZYZQUZUDLX-UHFFFAOYSA-N 2-chloro-4-phenylsulfanylpyridine Chemical compound C1=NC(Cl)=CC(SC=2C=CC=CC=2)=C1 DTWGZYZQUZUDLX-UHFFFAOYSA-N 0.000 description 2
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- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2002-0015755A KR100450700B1 (ko) | 2002-03-22 | 2002-03-22 | 티아졸리딘디온 유도체 화합물 및 이를 함유하는 약제학적조성물 |
| KR2002/15755 | 2002-03-22 | ||
| PCT/KR2002/000542 WO2003080605A1 (en) | 2002-03-22 | 2002-03-28 | Thiazolidinedione derivatives and pharmaceutical composition comprising the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2479274A1 CA2479274A1 (en) | 2003-10-02 |
| CA2479274C true CA2479274C (en) | 2010-02-16 |
Family
ID=28450054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2479274A Expired - Lifetime CA2479274C (en) | 2002-03-22 | 2002-03-28 | Thiazolidinedione derivatives and pharmaceutical composition comprising the same |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6787551B2 (und) |
| EP (1) | EP1490360B1 (und) |
| JP (1) | JP4181050B2 (und) |
| KR (1) | KR100450700B1 (und) |
| CN (1) | CN1276920C (und) |
| AT (1) | ATE502034T1 (und) |
| AU (1) | AU2002244985A1 (und) |
| CA (1) | CA2479274C (und) |
| DE (1) | DE60239491D1 (und) |
| ES (1) | ES2360381T3 (und) |
| WO (1) | WO2003080605A1 (und) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7833513B2 (en) | 2004-12-03 | 2010-11-16 | Rhode Island Hospital | Treatment of Alzheimer's Disease |
| US7435741B2 (en) | 2006-05-09 | 2008-10-14 | Teva Pharmaceutical Industries, Ltd. | 2-N{5-[[4-[2-(methyl-2-pyridinylamino) ethoxy] phenyl]methyl]-2,4-thiazolidinedione} butanedioic acid, methods of preparation and compositions with rosiglitazone maleate |
| WO2013082106A1 (en) | 2011-12-02 | 2013-06-06 | The General Hospital Corporation | Differentiation into brown adipocytes |
| KR101721831B1 (ko) | 2014-11-06 | 2017-03-31 | 주식회사 종근당 | 로베글리타존을 함유하는 경구 투여용 약제학적 조성물 |
| WO2016153949A1 (en) * | 2015-03-20 | 2016-09-29 | Deuterx, Llc | 5-deutero-thiazolidine-2,4-dione compounds and methods of treating medical disorders using same |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1003445B (zh) * | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| AR240698A1 (es) * | 1985-01-19 | 1990-09-28 | Takeda Chemical Industries Ltd | Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales |
| DE10199003I1 (de) * | 1987-09-04 | 2003-06-12 | Beecham Group Plc | Substituierte Thiazolidinionderivate |
| US5441971A (en) | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| CA2118706A1 (en) * | 1992-07-13 | 1994-01-20 | Saizo Shibata | Novel thiazolidinedione compounds and use thereof |
| US6046222A (en) | 1993-09-15 | 2000-04-04 | Warner-Lambert Company | Use of thiazolidinedione derivatives in the treatment of polycystic ovary syndrome, gestational diabetes and disease states at risk for progressing to noninsulin-dependent diabetes mellitus |
| US5457109A (en) * | 1993-09-15 | 1995-10-10 | Warner-Lambert Company | Use of thiazolidinedione derivatives and related antihyperglycemic agents in the treatment of disease states at risk for progressing to noninsulin-dependent diabetes mellitus |
| US5708012A (en) * | 1995-04-28 | 1998-01-13 | Sankyo Company, Limited | Use of thiazolidinedione derivatives and related antihyperglycemic agents in the treatment of insulin resistant subjects with normal glucose tolerance in order to prevent or delay the onset of noninsulin-dependent mellitus |
| GB9726563D0 (en) * | 1997-12-16 | 1998-02-11 | Smithkline Beecham Plc | Novel pharmaceutical |
| GB9909075D0 (en) * | 1999-04-20 | 1999-06-16 | Smithkline Beecham Plc | Novel pharmaceutical |
| IL148164A0 (en) * | 1999-08-17 | 2002-09-12 | Smithkline Beecham Plc | Pharmaceutical compositions containing thiazolidinedione derivatives and process for their preparation |
| ES2156574B1 (es) * | 1999-11-18 | 2002-02-01 | Vita Invest Sa | Nuevos derivados de tiazolidindiona como agentes antidiabeticos |
-
2002
- 2002-03-22 KR KR10-2002-0015755A patent/KR100450700B1/ko not_active Expired - Lifetime
- 2002-03-28 AU AU2002244985A patent/AU2002244985A1/en not_active Abandoned
- 2002-03-28 CA CA2479274A patent/CA2479274C/en not_active Expired - Lifetime
- 2002-03-28 EP EP02713320A patent/EP1490360B1/en not_active Expired - Lifetime
- 2002-03-28 WO PCT/KR2002/000542 patent/WO2003080605A1/en active Application Filing
- 2002-03-28 JP JP2003578359A patent/JP4181050B2/ja not_active Expired - Lifetime
- 2002-03-28 ES ES02713320T patent/ES2360381T3/es not_active Expired - Lifetime
- 2002-03-28 CN CNB028286103A patent/CN1276920C/zh not_active Expired - Lifetime
- 2002-03-28 DE DE60239491T patent/DE60239491D1/de not_active Expired - Lifetime
- 2002-03-28 AT AT02713320T patent/ATE502034T1/de active
- 2002-03-28 US US10/250,502 patent/US6787551B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003080605A1 (en) | 2003-10-02 |
| DE60239491D1 (de) | 2011-04-28 |
| CN1622945A (zh) | 2005-06-01 |
| EP1490360B1 (en) | 2011-03-16 |
| US20040122031A1 (en) | 2004-06-24 |
| ES2360381T3 (es) | 2011-06-03 |
| EP1490360A1 (en) | 2004-12-29 |
| KR20030076094A (ko) | 2003-09-26 |
| JP4181050B2 (ja) | 2008-11-12 |
| JP2005520862A (ja) | 2005-07-14 |
| KR100450700B1 (ko) | 2004-10-01 |
| AU2002244985A1 (en) | 2003-10-08 |
| US6787551B2 (en) | 2004-09-07 |
| ATE502034T1 (de) | 2011-04-15 |
| EP1490360A4 (en) | 2006-07-05 |
| CA2479274A1 (en) | 2003-10-02 |
| CN1276920C (zh) | 2006-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20220328 |
|
| MKEX | Expiry |
Effective date: 20220328 |