UA63980C2 - A hydrate of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salts - Google Patents
A hydrate of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salts Download PDFInfo
- Publication number
- UA63980C2 UA63980C2 UA2000063484A UA2000063484A UA63980C2 UA 63980 C2 UA63980 C2 UA 63980C2 UA 2000063484 A UA2000063484 A UA 2000063484A UA 2000063484 A UA2000063484 A UA 2000063484A UA 63980 C2 UA63980 C2 UA 63980C2
- Authority
- UA
- Ukraine
- Prior art keywords
- hydrate
- hydrate according
- diabetes
- methyl
- dione
- Prior art date
Links
- 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 title abstract 2
- 150000002688 maleic acid derivatives Chemical class 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000002329 infrared spectrum Methods 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- HAFWELDDNUXLCK-ODZAUARKSA-N (z)-but-2-enedioic acid;hydrate Chemical compound O.OC(=O)\C=C/C(O)=O HAFWELDDNUXLCK-ODZAUARKSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 150000002689 maleic acids Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 239000000203 mixture Substances 0.000 abstract description 17
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 description 11
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- 150000003839 salts Chemical class 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
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- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
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- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 206010020710 Hyperphagia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
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- 239000011230 binding agent Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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- 208000028208 end stage renal disease Diseases 0.000 description 1
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
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- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
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- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical group COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
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- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9726568.0A GB9726568D0 (en) | 1997-12-16 | 1997-12-16 | Novel pharmaceutical |
| PCT/EP1998/008154 WO1999031094A1 (en) | 1997-12-16 | 1998-12-14 | Hydrate of 5-[4-[2- (n-methyl-n- (2-pyridil)amino) ethoxy]benzyl] thiazolidine-2, 4-dione maleic acid salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA63980C2 true UA63980C2 (en) | 2004-02-16 |
Family
ID=10823694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2000063484A UA63980C2 (en) | 1997-12-16 | 1998-12-14 | A hydrate of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salts |
Country Status (37)
| Country | Link |
|---|---|
| US (2) | US7045633B2 (sr) |
| EP (1) | EP1045847A1 (sr) |
| JP (1) | JP2002508372A (sr) |
| KR (1) | KR100549143B1 (sr) |
| CN (3) | CN101412714A (sr) |
| AP (1) | AP1441A (sr) |
| AR (2) | AR017213A1 (sr) |
| AU (1) | AU2272399A (sr) |
| BG (1) | BG64905B1 (sr) |
| BR (1) | BR9813604A (sr) |
| CA (1) | CA2314965A1 (sr) |
| CO (1) | CO4990927A1 (sr) |
| CZ (1) | CZ299970B6 (sr) |
| DZ (1) | DZ2680A1 (sr) |
| EA (1) | EA002355B1 (sr) |
| EG (2) | EG23694A (sr) |
| GB (1) | GB9726568D0 (sr) |
| HR (1) | HRP20000405A2 (sr) |
| HU (1) | HUP0100500A3 (sr) |
| ID (1) | ID24744A (sr) |
| IL (1) | IL136381A (sr) |
| IN (1) | IN190821B (sr) |
| MA (1) | MA26582A1 (sr) |
| MY (1) | MY135770A (sr) |
| NO (1) | NO317253B1 (sr) |
| NZ (1) | NZ504704A (sr) |
| OA (1) | OA11634A (sr) |
| PE (1) | PE20000057A1 (sr) |
| PL (1) | PL341147A1 (sr) |
| RS (1) | RS50079B (sr) |
| SK (1) | SK286197B6 (sr) |
| TR (2) | TR200001798T2 (sr) |
| TW (1) | TW467913B (sr) |
| UA (1) | UA63980C2 (sr) |
| UY (2) | UY25305A1 (sr) |
| WO (1) | WO1999031094A1 (sr) |
| ZA (1) | ZA9811505B (sr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9909041D0 (en) * | 1999-04-20 | 1999-06-16 | Smithkline Beecham Plc | Novel pharmaceutical |
| US20040248945A1 (en) | 1999-04-23 | 2004-12-09 | Smithkline Beecham P.L.C. | Thiazolidinedione derivative and its use as antidiabetic |
| PL351686A1 (en) | 1999-04-23 | 2003-06-02 | Smithkline Beecham Plc | Novel pharmaceutical |
| UA67845C2 (uk) * | 1999-04-23 | 2004-07-15 | Smithkline Beecham Plc | Поліморф 5-[4-[2- (n-метил-n-(2-піридил)аміно)етокси]бензил]тіазолідин-2,4-діону солі малеїнової кислоти |
| GB0014005D0 (en) * | 2000-06-08 | 2000-08-02 | Smithkline Beecham Plc | Novel pharmaceutical |
| GB0021784D0 (en) * | 2000-09-05 | 2000-10-18 | Smithkline Beecham Plc | Novel pharmaceutical |
| GB0021978D0 (en) * | 2000-09-07 | 2000-10-25 | Smithkline Beecham Plc | Novel pharmaceutical |
| AU2002352391A1 (en) * | 2001-12-13 | 2003-06-23 | Smithkline Beecham Plc | A 5(-4-(2-(n-methyl-n-(2-pyridil)amino)ethoxy)benzyl)thiazolidine-2,4-dione (i) 10-camphorsulphonic acid salt and use against diabetes mellitus |
| GB0129876D0 (en) * | 2001-12-13 | 2002-02-06 | Smithkline Beecham Plc | Novel pharmaceutical |
| WO2003050112A1 (en) * | 2001-12-13 | 2003-06-19 | Smithkline Beecham Plc | Toluenesulfonate hydrates of a thiazolidinedione derivative |
| AU2002352479A1 (en) * | 2001-12-20 | 2003-07-09 | Smithkline Beecham Plc | 5- (4- (2- (n-methyl-n- (2-pyridyl) amino) ethoxy) benzyl) thiazolidine-2, 4-dione malic acid salt and use against diabetes mellitus |
| GB0130511D0 (en) * | 2001-12-20 | 2002-02-06 | Smithkline Beecham Plc | Novel pharmaceutical |
| GB2405403A (en) * | 2003-08-29 | 2005-03-02 | Cipla Ltd | Rosiglitazone maleate of particular polymorphic forms and methods of preparing rosiglitazone free base |
| ITMI20041537A1 (it) * | 2004-07-28 | 2004-10-28 | Chemi Spa | Nuova forma polimorfa del rosiglitazone maleato |
| CZ298424B6 (cs) * | 2005-05-24 | 2007-09-26 | Zentiva, A. S. | Zpusob krystalizace rosiglitazonu a jeho derivátuze smesných rozpouštedel |
| EP2184055A1 (en) | 2008-11-07 | 2010-05-12 | LEK Pharmaceuticals d.d. | Process for preparing solid dosage forms of rosiglitazone maleate |
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| 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 |
| US4812570A (en) * | 1986-07-24 | 1989-03-14 | Takeda Chemical Industries, Ltd. | Method for producing thiazolidinedione derivatives |
| EP0842925A1 (en) | 1987-09-04 | 1998-05-20 | Beecham Group Plc | Substituted thiazolidinedione derivatives |
| GB8820389D0 (en) * | 1988-08-26 | 1988-09-28 | Beecham Group Plc | Novel compounds |
| GB9124513D0 (en) | 1991-11-19 | 1992-01-08 | Smithkline Beecham Plc | Novel process |
| JPH08500835A (ja) | 1992-08-28 | 1996-01-30 | メルク エンド カンパニー インコーポレーテッド | 陽イオン性−２−ヘテロアリールフェニル−カルバペネム抗菌剤 |
| GB9218830D0 (en) | 1992-09-05 | 1992-10-21 | Smithkline Beecham Plc | Novel compounds |
| US5741803A (en) | 1992-09-05 | 1998-04-21 | Smithkline Beecham Plc | Substituted thiazolidinedionle derivatives |
| TW245716B (sr) * | 1992-12-28 | 1995-04-21 | Takeda Pharm Industry Co | |
| DE4404198A1 (de) | 1994-02-10 | 1995-08-17 | Henkel Kgaa | 2-Fluor-6-nitroaniline |
| US20020137940A1 (en) | 1997-12-16 | 2002-09-26 | Smithkline Beecham P.L.C. | 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2, 4-dione, maleic acid salt, hydrate as pharmaceutical |
| GB9726563D0 (en) | 1997-12-16 | 1998-02-11 | Smithkline Beecham Plc | Novel pharmaceutical |
| GB9726566D0 (en) | 1997-12-16 | 1998-02-11 | Smithkline Beecham Plc | Novel pharmaceutical |
| US6664278B2 (en) * | 1997-12-16 | 2003-12-16 | Smithkline Beecham P.L.C. | Hydrate of 5-[4-[2-(N-methyl-N-(2-pyridil)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt |
| CZ432299A3 (cs) * | 1998-06-02 | 2000-08-16 | Smithkline Beecham Plc | Kompozice obsahující 5-[4-[2-(N-methyl-N-(2- pyridyI)amino)ethoxy]benzyl]thiazolidin-2,4-dion |
| UA67845C2 (uk) | 1999-04-23 | 2004-07-15 | Smithkline Beecham Plc | Поліморф 5-[4-[2- (n-метил-n-(2-піридил)аміно)етокси]бензил]тіазолідин-2,4-діону солі малеїнової кислоти |
| PL351686A1 (en) | 1999-04-23 | 2003-06-02 | Smithkline Beecham Plc | Novel pharmaceutical |
| AU765005B2 (en) | 1999-04-23 | 2003-09-04 | Smithkline Beecham Plc | Polymorph of 5-(4-(2- (N-methyl-N-( 2-pyridyl)amino) ethoxy)benzyl) thiazolidine-2,4-dione, maleic acid salt |
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1997
- 1997-12-16 GB GBGB9726568.0A patent/GB9726568D0/en not_active Ceased
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1998
- 1998-12-14 MA MA25392A patent/MA26582A1/fr unknown
- 1998-12-14 IL IL13638198A patent/IL136381A/xx unknown
- 1998-12-14 AP APAP/P/2000/001830A patent/AP1441A/en active
- 1998-12-14 CZ CZ20002205A patent/CZ299970B6/cs not_active IP Right Cessation
- 1998-12-14 EA EA200000655A patent/EA002355B1/ru not_active IP Right Cessation
- 1998-12-14 OA OA1200000179A patent/OA11634A/en unknown
- 1998-12-14 TR TR2000/01798T patent/TR200001798T2/xx unknown
- 1998-12-14 CN CNA2008100930575A patent/CN101412714A/zh active Pending
- 1998-12-14 WO PCT/EP1998/008154 patent/WO1999031094A1/en active IP Right Grant
- 1998-12-14 HU HU0100500A patent/HUP0100500A3/hu unknown
- 1998-12-14 CN CN98812092A patent/CN1281454A/zh active Pending
- 1998-12-14 BR BR9813604-6A patent/BR9813604A/pt not_active Application Discontinuation
- 1998-12-14 JP JP2000539018A patent/JP2002508372A/ja not_active Withdrawn
- 1998-12-14 UA UA2000063484A patent/UA63980C2/uk unknown
- 1998-12-14 RS YUP-362/00A patent/RS50079B/sr unknown
- 1998-12-14 KR KR1020007006517A patent/KR100549143B1/ko not_active IP Right Cessation
- 1998-12-14 CA CA002314965A patent/CA2314965A1/en not_active Abandoned
- 1998-12-14 CN CNA2008100930560A patent/CN101412713A/zh active Pending
- 1998-12-14 NZ NZ504704A patent/NZ504704A/xx unknown
- 1998-12-14 PL PL98341147A patent/PL341147A1/xx not_active Application Discontinuation
- 1998-12-14 AU AU22723/99A patent/AU2272399A/en not_active Abandoned
- 1998-12-14 ID IDW20001126A patent/ID24744A/id unknown
- 1998-12-14 EP EP98966321A patent/EP1045847A1/en not_active Ceased
- 1998-12-14 SK SK910-2000A patent/SK286197B6/sk not_active IP Right Cessation
- 1998-12-15 AR ARP980106369A patent/AR017213A1/es not_active Application Discontinuation
- 1998-12-15 UY UY25305A patent/UY25305A1/es not_active IP Right Cessation
- 1998-12-15 UY UY25310A patent/UY25310A1/es not_active IP Right Cessation
- 1998-12-15 MY MYPI98005675A patent/MY135770A/en unknown
- 1998-12-15 EG EG155098A patent/EG23694A/xx active
- 1998-12-15 DZ DZ980290A patent/DZ2680A1/xx active
- 1998-12-15 AR ARP980106365A patent/AR017430A1/es not_active Application Discontinuation
- 1998-12-15 EG EG155498A patent/EG21417A/xx active
- 1998-12-15 ZA ZA9811505A patent/ZA9811505B/xx unknown
- 1998-12-16 IN IN3770DE1998 patent/IN190821B/en unknown
- 1998-12-16 TW TW087121122A patent/TW467913B/zh not_active IP Right Cessation
- 1998-12-16 PE PE1998001232A patent/PE20000057A1/es not_active Application Discontinuation
- 1998-12-16 TR TR1998/02626A patent/TR199802626A2/xx unknown
- 1998-12-16 CO CO98074830A patent/CO4990927A1/es unknown
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2000
- 2000-06-15 NO NO20003068A patent/NO317253B1/no not_active IP Right Cessation
- 2000-06-16 HR HR20000405A patent/HRP20000405A2/hr not_active Application Discontinuation
- 2000-07-11 BG BG104595A patent/BG64905B1/bg unknown
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2003
- 2003-10-24 US US10/692,544 patent/US7045633B2/en not_active Expired - Fee Related
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2006
- 2006-03-16 US US11/377,470 patent/US20060189659A1/en not_active Abandoned
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