HRP20020426A2 - Novel thiazolidinedione derivatives as antidiabetic agents - Google Patents
Novel thiazolidinedione derivatives as antidiabetic agents Download PDFInfo
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- HRP20020426A2 HRP20020426A2 HR20020426A HRP20020426A HRP20020426A2 HR P20020426 A2 HRP20020426 A2 HR P20020426A2 HR 20020426 A HR20020426 A HR 20020426A HR P20020426 A HRP20020426 A HR P20020426A HR P20020426 A2 HRP20020426 A2 HR P20020426A2
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- Croatia
- Prior art keywords
- thiazolidine
- dione
- benzyl
- ethoxy
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- 239000003472 antidiabetic agent Substances 0.000 title claims description 6
- 150000001467 thiazolidinediones Chemical class 0.000 title description 6
- 229940125708 antidiabetic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229940123208 Biguanide Drugs 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- 150000004283 biguanides Chemical class 0.000 claims description 4
- 230000002255 enzymatic effect Effects 0.000 claims description 4
- 201000001421 hyperglycemia Diseases 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 201000001431 Hyperuricemia Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 230000003178 anti-diabetic effect Effects 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 230000002124 endocrine Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000002503 metabolic effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
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- 150000002739 metals Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- -1 R2: H Chemical group 0.000 claims 6
- 238000006722 reduction reaction Methods 0.000 claims 3
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- 238000003786 synthesis reaction Methods 0.000 description 8
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- 125000004076 pyridyl group Chemical group 0.000 description 4
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- BARHZCGUELEWRA-UHFFFAOYSA-N 5-[[4-[2-[methyl(pyrimidin-4-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=NC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O BARHZCGUELEWRA-UHFFFAOYSA-N 0.000 description 3
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 3
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- ZXQIYCGAOJJLGY-UHFFFAOYSA-N 5-[[4-[2-[(5-amino-6-chloropyrimidin-4-yl)-methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C=NC(Cl)=C(N)C=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O ZXQIYCGAOJJLGY-UHFFFAOYSA-N 0.000 description 1
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- URBOKHJCLHLVLS-UHFFFAOYSA-N 5-[[4-[2-[[6-(dimethylamino)pyrimidin-4-yl]-methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=NC(N(C)C)=CC(N(C)CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=N1 URBOKHJCLHLVLS-UHFFFAOYSA-N 0.000 description 1
- VWYQXIOVYLIADH-UHFFFAOYSA-N 5-[[4-[2-[methyl-(2-methylsulfanylpyrimidin-4-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CSC1=NC=CC(N(C)CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=N1 VWYQXIOVYLIADH-UHFFFAOYSA-N 0.000 description 1
- RDTPHIADUBCKKU-UHFFFAOYSA-N 5-[[4-[2-[methyl-(2-phenylquinazolin-4-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O RDTPHIADUBCKKU-UHFFFAOYSA-N 0.000 description 1
- GMMAWFITQJPLAK-UHFFFAOYSA-N 5-[[4-[2-[methyl-(7-methylpurin-6-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C=NC=2N=CN(C)C=2C=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O GMMAWFITQJPLAK-UHFFFAOYSA-N 0.000 description 1
- NCZREVPKGQGLFM-UHFFFAOYSA-N 6-chloro-7-methylpurine Chemical compound C1=NC(Cl)=C2N(C)C=NC2=N1 NCZREVPKGQGLFM-UHFFFAOYSA-N 0.000 description 1
- RHDBIPGIAGHQMT-HEEXEHOYSA-N 6-chloro-7h-purine;(2r,3r,4r)-2,3,4,5-tetrahydroxypentanal Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O.ClC1=NC=NC2=C1NC=N2 RHDBIPGIAGHQMT-HEEXEHOYSA-N 0.000 description 1
- QSTASPNCKDPSAH-UHFFFAOYSA-N 6-chloro-9-(oxan-2-yl)purine Chemical compound C1=NC=2C(Cl)=NC=NC=2N1C1CCCCO1 QSTASPNCKDPSAH-UHFFFAOYSA-N 0.000 description 1
- UEZNSCCMEMUEMO-UHFFFAOYSA-N 6-chloro-9-methylpurine Chemical compound N1=CN=C2N(C)C=NC2=C1Cl UEZNSCCMEMUEMO-UHFFFAOYSA-N 0.000 description 1
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- BAWFJGJZGIEFAR-DQQFMEOOSA-N [[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)O[P@@](O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-DQQFMEOOSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002058 anti-hyperglycaemic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- JORABGDXCIBAFL-UHFFFAOYSA-M iodonitrotetrazolium chloride Chemical compound [Cl-].C1=CC([N+](=O)[O-])=CC=C1N1[N+](C=2C=CC(I)=CC=2)=NC(C=2C=CC=CC=2)=N1 JORABGDXCIBAFL-UHFFFAOYSA-M 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000004066 metabolic change Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P3/08—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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
-
- 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
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009902533A ES2156574B1 (es) | 1999-11-18 | 1999-11-18 | Nuevos derivados de tiazolidindiona como agentes antidiabeticos |
| PCT/ES2000/000432 WO2001036416A1 (es) | 1999-11-18 | 2000-11-15 | Nuevos derivados de tiazolidindiona como agentes antidiabeticos |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020426A2 true HRP20020426A2 (en) | 2004-02-29 |
Family
ID=8310628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020426A HRP20020426A2 (en) | 1999-11-18 | 2002-05-15 | Novel thiazolidinedione derivatives as antidiabetic agents |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US7001910B1 (sh) |
| EP (1) | EP1231211B1 (sh) |
| JP (1) | JP2003514817A (sh) |
| KR (1) | KR100518110B1 (sh) |
| CN (1) | CN1159314C (sh) |
| AP (1) | AP1330A (sh) |
| AR (1) | AR031080A1 (sh) |
| AT (1) | ATE241622T1 (sh) |
| AU (1) | AU770045B2 (sh) |
| BG (1) | BG106699A (sh) |
| BR (1) | BR0015613A (sh) |
| CA (1) | CA2391913A1 (sh) |
| CO (1) | CO5261560A1 (sh) |
| CR (1) | CR6640A (sh) |
| CZ (1) | CZ20021654A3 (sh) |
| DE (1) | DE60003072T2 (sh) |
| DK (1) | DK1231211T3 (sh) |
| EA (1) | EA004301B1 (sh) |
| EE (1) | EE200200254A (sh) |
| ES (2) | ES2156574B1 (sh) |
| GE (1) | GEP20043240B (sh) |
| HR (1) | HRP20020426A2 (sh) |
| HU (1) | HUP0203478A2 (sh) |
| IL (1) | IL149634A0 (sh) |
| IS (1) | IS2014B (sh) |
| MA (1) | MA26844A1 (sh) |
| MX (1) | MXPA02005011A (sh) |
| NO (2) | NO20022336L (sh) |
| NZ (1) | NZ519264A (sh) |
| OA (1) | OA12089A (sh) |
| PE (1) | PE20010858A1 (sh) |
| PL (1) | PL354877A1 (sh) |
| PT (1) | PT1231211E (sh) |
| SK (1) | SK6752002A3 (sh) |
| WO (1) | WO2001036416A1 (sh) |
| YU (1) | YU40202A (sh) |
| ZA (1) | ZA200203906B (sh) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2174748B1 (es) * | 2001-01-31 | 2003-09-16 | Vita Lab | Nueva sal de tiazolidindiona y sus polimorfos como agentes antidiabeticos y procedimiento para la obtencion de los mismos. |
| KR100450700B1 (ko) * | 2002-03-22 | 2004-10-01 | 주식회사종근당 | 티아졸리딘디온 유도체 화합물 및 이를 함유하는 약제학적조성물 |
| US7713983B2 (en) | 2003-03-03 | 2010-05-11 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| CL2004000409A1 (es) * | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| US20050014732A1 (en) * | 2003-03-14 | 2005-01-20 | Pharmacia Corporation | Combination of an aldosterone receptor antagonist and an anti-diabetic agent |
| US7928107B2 (en) | 2004-09-02 | 2011-04-19 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| US8283354B2 (en) | 2004-09-02 | 2012-10-09 | Vertex Pharmaceuticals Incorporated | Quinazolines useful as modulators of ion channels |
| CZ297347B6 (cs) * | 2004-09-21 | 2006-11-15 | Zentiva, A. S. | Zpusob prípravy rosiglitazonu |
| JP5546372B2 (ja) * | 2010-06-30 | 2014-07-09 | 積水メディカル株式会社 | ベンジルヒダントイン化合物の製造法 |
| WO2016184895A1 (en) | 2015-05-18 | 2016-11-24 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Means for detecting or measuring a biological activity of a botulinum toxin |
| US10689374B1 (en) | 2019-07-12 | 2020-06-23 | United Arab Emirates University | Pyrimidine-thiazolidinone derivatives |
| US10702525B1 (en) | 2019-09-04 | 2020-07-07 | United Arab Emirates University | Pyrimidine derivatives as anti-diabetic agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP0842925A1 (en) * | 1987-09-04 | 1998-05-20 | Beecham Group Plc | Substituted thiazolidinedione derivatives |
| GB9023583D0 (en) * | 1990-10-30 | 1990-12-12 | Beecham Group Plc | Novel compounds |
-
1999
- 1999-11-18 ES ES009902533A patent/ES2156574B1/es not_active Expired - Fee Related
-
2000
- 2000-11-06 AR ARP000105830A patent/AR031080A1/es unknown
- 2000-11-07 PE PE2000001189A patent/PE20010858A1/es not_active Application Discontinuation
- 2000-11-14 CO CO00086452A patent/CO5261560A1/es not_active Application Discontinuation
- 2000-11-15 AP APAP/P/2002/002512A patent/AP1330A/en active
- 2000-11-15 BR BR0015613-2A patent/BR0015613A/pt not_active IP Right Cessation
- 2000-11-15 IL IL14963400A patent/IL149634A0/xx unknown
- 2000-11-15 PT PT00974559T patent/PT1231211E/pt unknown
- 2000-11-15 SK SK675-2002A patent/SK6752002A3/sk unknown
- 2000-11-15 EP EP00974559A patent/EP1231211B1/en not_active Expired - Lifetime
- 2000-11-15 AT AT00974559T patent/ATE241622T1/de not_active IP Right Cessation
- 2000-11-15 ES ES00974559T patent/ES2199878T3/es not_active Expired - Lifetime
- 2000-11-15 CN CNB008166412A patent/CN1159314C/zh not_active Expired - Fee Related
- 2000-11-15 DK DK00974559T patent/DK1231211T3/da active
- 2000-11-15 YU YU40202A patent/YU40202A/sh unknown
- 2000-11-15 PL PL00354877A patent/PL354877A1/xx not_active IP Right Cessation
- 2000-11-15 HU HU0203478A patent/HUP0203478A2/hu unknown
- 2000-11-15 JP JP2001538905A patent/JP2003514817A/ja active Pending
- 2000-11-15 MX MXPA02005011A patent/MXPA02005011A/es active IP Right Grant
- 2000-11-15 AU AU12815/01A patent/AU770045B2/en not_active Ceased
- 2000-11-15 US US10/130,576 patent/US7001910B1/en not_active Expired - Fee Related
- 2000-11-15 EA EA200200470A patent/EA004301B1/ru not_active IP Right Cessation
- 2000-11-15 CA CA002391913A patent/CA2391913A1/en not_active Abandoned
- 2000-11-15 EE EEP200200254A patent/EE200200254A/xx unknown
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- 2000-11-15 CZ CZ20021654A patent/CZ20021654A3/cs unknown
- 2000-11-15 GE GEAP20006452A patent/GEP20043240B/en unknown
- 2000-11-15 DE DE60003072T patent/DE60003072T2/de not_active Expired - Fee Related
- 2000-11-15 WO PCT/ES2000/000432 patent/WO2001036416A1/es not_active Application Discontinuation
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- 2002-05-14 BG BG106699A patent/BG106699A/bg unknown
- 2002-05-15 IS IS6386A patent/IS2014B/is unknown
- 2002-05-15 CR CR6640A patent/CR6640A/es not_active Application Discontinuation
- 2002-05-15 HR HR20020426A patent/HRP20020426A2/hr not_active Application Discontinuation
- 2002-05-15 NO NO20022336A patent/NO20022336L/no not_active Application Discontinuation
- 2002-05-15 MA MA26638A patent/MA26844A1/fr unknown
- 2002-05-16 NO NO20022379A patent/NO20022379D0/no unknown
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