EA009331B1 - Способ получения полиморфа малеата розиглитазона - Google Patents
Способ получения полиморфа малеата розиглитазона Download PDFInfo
- Publication number
- EA009331B1 EA009331B1 EA200501527A EA200501527A EA009331B1 EA 009331 B1 EA009331 B1 EA 009331B1 EA 200501527 A EA200501527 A EA 200501527A EA 200501527 A EA200501527 A EA 200501527A EA 009331 B1 EA009331 B1 EA 009331B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- rosiglitazone maleate
- solvent
- rosiglitazone
- crystallization
- Prior art date
Links
- SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 title claims abstract description 68
- 229960003271 rosiglitazone maleate Drugs 0.000 title claims abstract description 68
- 238000004519 manufacturing process Methods 0.000 title abstract description 13
- 229940125904 compound 1 Drugs 0.000 claims abstract description 58
- 238000002425 crystallisation Methods 0.000 claims abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 37
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 230000008025 crystallization Effects 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 14
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 12
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 11
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 11
- 229940075894 denatured ethanol Drugs 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 8
- 229940011051 isopropyl acetate Drugs 0.000 claims description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 3
- SWXDHFLZCMRYEP-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-6-[3-(trifluoromethyl)pyridin-2-yl]oxyquinazolin-4-one Chemical compound FC1=CC(F)=CC=C1CN1C2=CC=C(OC=3C(=CC=CN=3)C(F)(F)F)C=C2C(=O)N=C1 SWXDHFLZCMRYEP-UHFFFAOYSA-N 0.000 claims 2
- 238000000151 deposition Methods 0.000 claims 1
- 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 abstract description 6
- 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 46
- 239000000047 product Substances 0.000 description 26
- 229960004586 rosiglitazone Drugs 0.000 description 23
- 238000001914 filtration Methods 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 17
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 17
- 239000011976 maleic acid Substances 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 17
- 239000000725 suspension Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 9
- 238000004566 IR spectroscopy Methods 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- -1 (2-pyridyl) amino Chemical group 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 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 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125708 antidiabetic agent Drugs 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
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0307259.2A GB0307259D0 (en) | 2003-03-28 | 2003-03-28 | Process |
| PCT/GB2004/001306 WO2004085435A1 (en) | 2003-03-28 | 2004-03-25 | Process for preparing a polymorph of rosiglitazone maleate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200501527A1 EA200501527A1 (ru) | 2006-02-24 |
| EA009331B1 true EA009331B1 (ru) | 2007-12-28 |
Family
ID=9955778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200501527A EA009331B1 (ru) | 2003-03-28 | 2004-03-25 | Способ получения полиморфа малеата розиглитазона |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20070167494A1 (https=) |
| EP (1) | EP1615918A1 (https=) |
| JP (1) | JP2006521340A (https=) |
| KR (1) | KR20050120670A (https=) |
| CN (1) | CN1768057A (https=) |
| AU (2) | AU2004224068A1 (https=) |
| BR (1) | BRPI0408752A (https=) |
| CA (1) | CA2520249A1 (https=) |
| EA (1) | EA009331B1 (https=) |
| EC (1) | ECSP056038A (https=) |
| GB (1) | GB0307259D0 (https=) |
| IS (1) | IS8087A (https=) |
| MA (1) | MA27727A1 (https=) |
| MX (1) | MXPA05010413A (https=) |
| NO (1) | NO20054911L (https=) |
| OA (1) | OA13042A (https=) |
| WO (1) | WO2004085435A1 (https=) |
| ZA (1) | ZA200507100B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20040248945A1 (en) | 1999-04-23 | 2004-12-09 | Smithkline Beecham P.L.C. | Thiazolidinedione derivative and its use as antidiabetic |
| 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 |
| WO2018140092A1 (en) | 2017-01-27 | 2018-08-02 | Obrien Christopher F | Methods for the administration of certain vmat2 inhibitors |
| ES3024958T3 (en) | 2017-09-21 | 2025-06-05 | Neurocrine Biosciences Inc | High dosage valbenazine formulation and compositions, methods, and kits related thereto |
| JP2021502959A (ja) | 2017-10-10 | 2021-02-04 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | 特定のｖｍａｔ２インヒビターを投与するための方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994005659A1 (en) * | 1992-09-05 | 1994-03-17 | Smithkline Beecham Plc | Substituted thiazolidinedione derivatives |
| WO2000064896A1 (en) * | 1999-04-23 | 2000-11-02 | Smithkline Beecham Plc | Polymorph of 5-[4-[2- (n-methyl-n-( 2-pyridyl)amino) ethoxy]benzyl] thiazolidine-2,4-dione, maleic acid salt |
| WO2002026737A1 (en) * | 2000-09-26 | 2002-04-04 | Dr. Reddy's Research Foundation | Novel polymorphic forms of 5-[4-[2-[n-methyl-n-(2-pyridyl)amino]ethoxy]benzyl] thiazolidine-2,4-dione maleate and process for their preparation |
| EP1219620A1 (en) * | 1997-11-04 | 2002-07-03 | Smithkline Beecham Plc | Process for the preparation of thiazolidinedione derivatives |
| EP1277753A1 (en) * | 1999-04-23 | 2003-01-22 | SmithKline Beecham plc | Thiazolidinedione derivative and its use as antidiabetic |
| EP1284268A1 (en) * | 1999-04-23 | 2003-02-19 | Smithkline Beecham Plc | Thiazolidinedione derivative and its use as antidiabetic |
-
2003
- 2003-03-28 GB GBGB0307259.2A patent/GB0307259D0/en not_active Ceased
-
2004
- 2004-03-25 KR KR1020057018143A patent/KR20050120670A/ko not_active Withdrawn
- 2004-03-25 BR BRPI0408752-6A patent/BRPI0408752A/pt not_active IP Right Cessation
- 2004-03-25 OA OA1200500267A patent/OA13042A/en unknown
- 2004-03-25 WO PCT/GB2004/001306 patent/WO2004085435A1/en not_active Ceased
- 2004-03-25 CA CA002520249A patent/CA2520249A1/en not_active Abandoned
- 2004-03-25 US US10/551,021 patent/US20070167494A1/en not_active Abandoned
- 2004-03-25 EP EP04723254A patent/EP1615918A1/en not_active Withdrawn
- 2004-03-25 CN CNA2004800083916A patent/CN1768057A/zh active Pending
- 2004-03-25 AU AU2004224068A patent/AU2004224068A1/en not_active Abandoned
- 2004-03-25 EA EA200501527A patent/EA009331B1/ru unknown
- 2004-03-25 MX MXPA05010413A patent/MXPA05010413A/es unknown
- 2004-03-25 JP JP2006506028A patent/JP2006521340A/ja not_active Withdrawn
-
2005
- 2005-09-05 ZA ZA200507100A patent/ZA200507100B/en unknown
- 2005-09-26 EC EC2005006038A patent/ECSP056038A/es unknown
- 2005-10-11 MA MA28549A patent/MA27727A1/fr unknown
- 2005-10-24 NO NO20054911A patent/NO20054911L/no not_active Application Discontinuation
- 2005-10-24 IS IS8087A patent/IS8087A/is unknown
-
2008
- 2008-10-30 AU AU2008237610A patent/AU2008237610A1/en not_active Abandoned
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994005659A1 (en) * | 1992-09-05 | 1994-03-17 | Smithkline Beecham Plc | Substituted thiazolidinedione derivatives |
| EP1219620A1 (en) * | 1997-11-04 | 2002-07-03 | Smithkline Beecham Plc | Process for the preparation of thiazolidinedione derivatives |
| WO2000064896A1 (en) * | 1999-04-23 | 2000-11-02 | Smithkline Beecham Plc | Polymorph of 5-[4-[2- (n-methyl-n-( 2-pyridyl)amino) ethoxy]benzyl] thiazolidine-2,4-dione, maleic acid salt |
| EP1277753A1 (en) * | 1999-04-23 | 2003-01-22 | SmithKline Beecham plc | Thiazolidinedione derivative and its use as antidiabetic |
| EP1284268A1 (en) * | 1999-04-23 | 2003-02-19 | Smithkline Beecham Plc | Thiazolidinedione derivative and its use as antidiabetic |
| WO2002026737A1 (en) * | 2000-09-26 | 2002-04-04 | Dr. Reddy's Research Foundation | Novel polymorphic forms of 5-[4-[2-[n-methyl-n-(2-pyridyl)amino]ethoxy]benzyl] thiazolidine-2,4-dione maleate and process for their preparation |
Non-Patent Citations (1)
| Title |
|---|
| WOLFFENBUTTEL B.H.R. ET AL.: "ROSIGLITAZONE," EXPERT OPINION ON PHARMACOTHERAPY, ASHLEY, LONDON, GB, vol. 2, no. 3, 2001, pages 467-478, XP001121064, ISSN: 1465-6566, the whole document * |
Also Published As
| Publication number | Publication date |
|---|---|
| OA13042A (en) | 2006-11-10 |
| IS8087A (is) | 2005-10-24 |
| EA200501527A1 (ru) | 2006-02-24 |
| CN1768057A (zh) | 2006-05-03 |
| MXPA05010413A (es) | 2005-11-04 |
| BRPI0408752A (pt) | 2006-03-28 |
| ZA200507100B (en) | 2006-07-26 |
| NO20054911L (no) | 2005-10-24 |
| KR20050120670A (ko) | 2005-12-22 |
| AU2008237610A1 (en) | 2008-11-27 |
| US20070167494A1 (en) | 2007-07-19 |
| JP2006521340A (ja) | 2006-09-21 |
| AU2004224068A1 (en) | 2004-10-07 |
| WO2004085435A1 (en) | 2004-10-07 |
| EP1615918A1 (en) | 2006-01-18 |
| CA2520249A1 (en) | 2004-10-07 |
| MA27727A1 (fr) | 2006-01-02 |
| ECSP056038A (es) | 2006-01-27 |
| GB0307259D0 (en) | 2003-05-07 |
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