JP2013501041A5 - - Google Patents
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- Publication number
- JP2013501041A5 JP2013501041A5 JP2012523394A JP2012523394A JP2013501041A5 JP 2013501041 A5 JP2013501041 A5 JP 2013501041A5 JP 2012523394 A JP2012523394 A JP 2012523394A JP 2012523394 A JP2012523394 A JP 2012523394A JP 2013501041 A5 JP2013501041 A5 JP 2013501041A5
- Authority
- JP
- Japan
- Prior art keywords
- tiotropium bromide
- less
- anhydride
- scopine
- glycolate
- 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.)
- Granted
Links
- 229960000257 tiotropium bromide Drugs 0.000 claims 37
- -1 Tiotropium bromide anhydride Chemical class 0.000 claims 28
- 238000000034 method Methods 0.000 claims 24
- VPJFFOQGKSJBAY-UGTXJPTRSA-N scopine di(2-thienyl)glycolate Chemical compound C([C@@H]1N([C@H](C2)[C@@H]3[C@H]1O3)C)C2OC(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 VPJFFOQGKSJBAY-UGTXJPTRSA-N 0.000 claims 13
- 239000012535 impurity Substances 0.000 claims 12
- 239000003960 organic solvent Substances 0.000 claims 12
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims 9
- 238000001035 drying Methods 0.000 claims 9
- 238000001228 spectrum Methods 0.000 claims 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- 150000002576 ketones Chemical group 0.000 claims 6
- 239000012296 anti-solvent Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 229940112141 dry powder inhaler Drugs 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940071648 metered dose inhaler Drugs 0.000 claims 1
- 229940102396 methyl bromide Drugs 0.000 claims 1
- 239000006199 nebulizer Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1048KO2009 | 2009-08-07 | ||
| IN1048/KOL/2009 | 2009-08-07 | ||
| PCT/GB2010/051310 WO2011015882A2 (en) | 2009-08-07 | 2010-08-06 | Novel anhydrate |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015155158A Division JP2015214574A (ja) | 2009-08-07 | 2015-08-05 | チオトロピウム臭化物の無水物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013501041A JP2013501041A (ja) | 2013-01-10 |
| JP2013501041A5 true JP2013501041A5 (enExample) | 2013-08-22 |
| JP5822831B2 JP5822831B2 (ja) | 2015-11-24 |
Family
ID=42830336
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012523394A Expired - Fee Related JP5822831B2 (ja) | 2009-08-07 | 2010-08-06 | チオトロピウム臭化物の無水物 |
| JP2015155158A Pending JP2015214574A (ja) | 2009-08-07 | 2015-08-05 | チオトロピウム臭化物の無水物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015155158A Pending JP2015214574A (ja) | 2009-08-07 | 2015-08-05 | チオトロピウム臭化物の無水物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8697719B2 (enExample) |
| EP (1) | EP2462140A2 (enExample) |
| JP (2) | JP5822831B2 (enExample) |
| CN (1) | CN102639531B (enExample) |
| AU (1) | AU2010280497B2 (enExample) |
| CA (2) | CA2768553C (enExample) |
| IN (1) | IN2012DN00968A (enExample) |
| NZ (2) | NZ597920A (enExample) |
| WO (1) | WO2011015882A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1869035E (pt) | 2005-12-19 | 2013-01-10 | Sicor Inc | Novas formas de brometo de tiotrópio e processos para sua preparação |
| US9108962B2 (en) | 2005-12-19 | 2015-08-18 | Sicor, Inc. | Forms of tiotropium bromide and processes for preparation thereof |
| CA2768553C (en) | 2009-08-07 | 2016-08-02 | Generics [Uk] Limited | Anhydrate of tiotropium bromide |
| TR201111589A2 (tr) * | 2011-03-03 | 2012-09-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür susuz kristal formu. |
| PT106142B (pt) | 2012-02-10 | 2014-07-18 | Hovione Farmaci Ncia S A | Processo para a preparação de brometo de tiotrópio |
| EP2897955B1 (en) * | 2012-09-11 | 2019-11-06 | Bilgic, Mahmut | New tiotropium bromide crystalline form |
| CN104341413A (zh) * | 2013-07-29 | 2015-02-11 | 天津金耀集团有限公司 | 一种无水噻托溴铵的新晶型 |
| HUE045868T2 (hu) * | 2013-11-22 | 2020-01-28 | Teva Branded Pharmaceutical Products R&D Inc | Inhalálható gyógykészítmény |
| EP2913332A1 (en) | 2014-02-27 | 2015-09-02 | Euticals S.P.A. | Crystalline form of tiotropium bromide with lactose |
| US10555903B2 (en) * | 2016-10-14 | 2020-02-11 | Glenmark Specialty S.A. | Nebulizable compositions of tiotropium and formoterol |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931041C2 (de) | 1989-09-16 | 2000-04-06 | Boehringer Ingelheim Kg | Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| US5610163A (en) | 1989-09-16 | 1997-03-11 | Boehringer Ingelheim Gmbh | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
| US6908928B2 (en) | 2000-10-12 | 2005-06-21 | Bi Pharma Kg. | Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions |
| AU2002214996B2 (en) | 2000-10-12 | 2007-03-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Crystalline monohydrate, method for producing the same and the use thereof in the production of a medicament |
| DE10064816A1 (de) | 2000-12-22 | 2002-06-27 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung eines Anticholinergikums |
| US6506900B1 (en) | 2001-01-31 | 2003-01-14 | Boehringer Ingelheim Pharma Ag | Process for preparing a scopine ester intermediate |
| AUPR315301A0 (en) | 2001-02-19 | 2001-03-15 | Silverbrook Research Pty. Ltd. | An Apparatus (ART102) |
| US6608055B2 (en) | 2001-06-22 | 2003-08-19 | Boehringer Ingelheim Pharma Kg | Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition |
| US6610849B2 (en) | 2001-06-28 | 2003-08-26 | Boehringer Ingelheim Pharma Kg | Process for the manufacture of tropenol |
| DE10200943A1 (de) | 2002-01-12 | 2003-07-24 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Scopinestern |
| US6747153B2 (en) | 2002-05-31 | 2004-06-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Industrial process for preparing tropenol |
| ES2329133T3 (es) | 2003-05-28 | 2009-11-23 | Theravance, Inc. | Compuestos azabicicloalcanicos como antagonistas de receptores de muscarinicos. |
| US7968717B2 (en) | 2003-11-03 | 2011-06-28 | Boehringer Ingelhein International Gmbh | Crystalline anhydrate with anticholinergic efficacy |
| WO2005042527A1 (de) * | 2003-11-03 | 2005-05-12 | Boehringer Ingelheim International Gmbh | Neues kristallines anhydrat mit anticholinerger wirksamkeit |
| CN1271073C (zh) * | 2004-10-26 | 2006-08-23 | 江苏正大天晴药业股份有限公司 | 结晶性抗胆碱能药噻托溴铵晶体 |
| WO2006076222A2 (en) | 2005-01-10 | 2006-07-20 | Glaxo Group Limited | Pharmaceutical formulations |
| EP1879888A2 (en) * | 2005-05-02 | 2008-01-23 | Boehringer Ingelheim International GmbH | Crystalline forms of tiotropium bromide |
| KR20080012932A (ko) * | 2005-05-02 | 2008-02-12 | 베링거 인겔하임 인터내셔날 게엠베하 | 티오트로퓸 브로마이드의 신규한 결정형 |
| DE102005035112A1 (de) | 2005-07-27 | 2007-02-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neues Verfahren zur Herstellung von Tiotropiumsalzen unter Anwendung von in organischen Lösungsmitteln löslichen N-Methylscopiniumsalzen |
| PT1869035E (pt) * | 2005-12-19 | 2013-01-10 | Sicor Inc | Novas formas de brometo de tiotrópio e processos para sua preparação |
| JP2008530251A (ja) * | 2005-12-19 | 2008-08-07 | シコール インコーポレイティド | 純粋且つ安定な臭化チオトロピウム |
| US20070167480A1 (en) * | 2005-12-19 | 2007-07-19 | Sicor Inc. | Pure and stable tiotropium bromide |
| CN100410254C (zh) * | 2006-03-07 | 2008-08-13 | 南昌弘益科技有限公司 | 噻托溴铵无水物制备方法 |
| US20080051582A1 (en) | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| WO2008089852A1 (de) | 2007-01-26 | 2008-07-31 | Boehringer Ingelheim Pharma Gmbh & Co.Kg | Neues verfahren zur herstellung von tiotropiumsalzen |
| KR20150038750A (ko) | 2007-02-21 | 2015-04-08 | 알미랄, 에스.에이. | 신규 방법 |
| WO2008104955A1 (en) | 2007-02-28 | 2008-09-04 | Ranbaxy Laboratories Limited | Azoniatricyclo [3.3.1.0] nonane derivatives as muscarinic receptor antagonists |
| WO2009087419A1 (en) | 2008-01-10 | 2009-07-16 | Generics [Uk] Limited | Novel process for the preparation of scopine esters |
| WO2011015884A1 (en) | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Process to prepare scopine esters |
| WO2011015883A1 (en) | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Dichloromethane solvate of tiotropium bromide and its use |
| CA2768553C (en) | 2009-08-07 | 2016-08-02 | Generics [Uk] Limited | Anhydrate of tiotropium bromide |
| WO2011095800A2 (en) | 2010-02-02 | 2011-08-11 | Generics [Uk] Limited | Analytical methods |
-
2010
- 2010-08-06 CA CA2768553A patent/CA2768553C/en not_active Expired - Fee Related
- 2010-08-06 WO PCT/GB2010/051310 patent/WO2011015882A2/en not_active Ceased
- 2010-08-06 CA CA2931876A patent/CA2931876A1/en not_active Abandoned
- 2010-08-06 JP JP2012523394A patent/JP5822831B2/ja not_active Expired - Fee Related
- 2010-08-06 AU AU2010280497A patent/AU2010280497B2/en not_active Ceased
- 2010-08-06 EP EP10743206.4A patent/EP2462140A2/en not_active Ceased
- 2010-08-06 CN CN201080044044.4A patent/CN102639531B/zh not_active Expired - Fee Related
- 2010-08-06 IN IN968DEN2012 patent/IN2012DN00968A/en unknown
- 2010-08-06 NZ NZ597920A patent/NZ597920A/en not_active IP Right Cessation
- 2010-08-06 NZ NZ624602A patent/NZ624602A/en not_active IP Right Cessation
- 2010-08-06 US US13/386,550 patent/US8697719B2/en not_active Expired - Fee Related
-
2014
- 2014-04-07 US US14/246,291 patent/US9181268B2/en active Active
-
2015
- 2015-08-05 JP JP2015155158A patent/JP2015214574A/ja active Pending
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