JP2008540366A5 - - Google Patents
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- Publication number
- JP2008540366A5 JP2008540366A5 JP2008509408A JP2008509408A JP2008540366A5 JP 2008540366 A5 JP2008540366 A5 JP 2008540366A5 JP 2008509408 A JP2008509408 A JP 2008509408A JP 2008509408 A JP2008509408 A JP 2008509408A JP 2008540366 A5 JP2008540366 A5 JP 2008540366A5
- Authority
- JP
- Japan
- Prior art keywords
- tiotropium bromide
- solvate
- crystalline
- dried
- crystalline tiotropium
- 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 43
- 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 41
- 239000012453 solvate Substances 0.000 claims 40
- 239000002904 solvent Substances 0.000 claims 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 21
- 239000013078 crystal Substances 0.000 claims 17
- MQLXPRBEAHBZTK-SEINRUQRSA-M tiotropium bromide hydrate Chemical compound O.[Br-].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 MQLXPRBEAHBZTK-SEINRUQRSA-M 0.000 claims 16
- 238000004519 manufacturing process Methods 0.000 claims 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 11
- 238000010586 diagram Methods 0.000 claims 10
- 239000000843 powder Substances 0.000 claims 10
- 238000001816 cooling Methods 0.000 claims 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 4
- 238000001035 drying Methods 0.000 claims 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 238000012916 structural analysis Methods 0.000 claims 4
- 229940110309 tiotropium Drugs 0.000 claims 4
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- 235000013772 propylene glycol Nutrition 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- 239000000808 adrenergic beta-agonist Substances 0.000 claims 2
- 230000003454 betamimetic effect Effects 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- -1 tiotropium bromide anhydride Chemical class 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 229940121647 egfr inhibitor Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 150000003431 steroids Chemical group 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67680705P | 2005-05-02 | 2005-05-02 | |
| US60/676,807 | 2005-05-02 | ||
| PCT/EP2006/061763 WO2006117299A2 (en) | 2005-05-02 | 2006-04-21 | Novel crystalline forms of tiotropium bromide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008540366A JP2008540366A (ja) | 2008-11-20 |
| JP2008540366A5 true JP2008540366A5 (cg-RX-API-DMAC7.html) | 2009-06-18 |
| JP5227790B2 JP5227790B2 (ja) | 2013-07-03 |
Family
ID=36693210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008509408A Active JP5227790B2 (ja) | 2005-05-02 | 2006-04-21 | 新規結晶性臭化チオトロピウム |
Country Status (23)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101395881B1 (ko) * | 2005-12-19 | 2014-05-21 | 시코르, 인크. | 브롬화 티오트로피움의 신규한 형태 및 이의 제조 방법 |
| CN101360744A (zh) * | 2005-12-19 | 2009-02-04 | 西科尔公司 | 纯和稳定的噻托溴铵 |
| US9108962B2 (en) | 2005-12-19 | 2015-08-18 | Sicor, Inc. | Forms of tiotropium bromide and processes for preparation thereof |
| CN100999521B (zh) * | 2006-01-13 | 2010-12-08 | 江苏正大天晴药业股份有限公司 | 结晶性抗胆碱药噻托溴铵 |
| US20080051582A1 (en) | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| EP1923393A1 (en) * | 2006-11-17 | 2008-05-21 | Boehringer Ingelheim Pharma GmbH & Co. KG | Crystalline form of tiotropium bromide and urea |
| GB0716026D0 (en) * | 2007-08-16 | 2007-09-26 | Norton Healthcare Ltd | An inhalable medicament |
| PT2240477E (pt) * | 2008-01-10 | 2014-11-19 | Generics Uk Ltd | Um novo processo para a preparação de ésteres de escopina |
| BRPI0916047A2 (pt) * | 2008-11-04 | 2015-11-10 | Cipla Ltd | composição farmacêutica em aerossol, uso de uma composição farmacêutica em aerossol, método para tratamento de sintomas crônicos ou agudos severos, moderados ou leves, ou para tratamento profilático de um distúrbio respiratório, dispensador farmacêutico em aerossol, processo para fabricação de um dispensador farmacêutico em aerossol e processo para fabricação de um complexo de um agente ativo e um adjuvante |
| KR101557633B1 (ko) * | 2008-11-04 | 2015-10-06 | 시플라 리미티드 | 낮은 결정화도를 갖는 티오트로피움 브로마이드 |
| WO2010101538A2 (en) | 2009-03-06 | 2010-09-10 | Bilgic Mahmut | New crystal forms |
| WO2011015883A1 (en) | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Dichloromethane solvate of tiotropium bromide and its use |
| US8697719B2 (en) * | 2009-08-07 | 2014-04-15 | Generics [Uk] Limited | Anhydrate of tiotropium bromide |
| TR201007108A2 (tr) * | 2010-08-25 | 2012-03-21 | B�Lg�� Mahmut | Yeni tiotropyum bromür kristali ve üretim yöntemi.@ |
| TR201102068A2 (tr) | 2011-03-03 | 2012-09-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür içeren kristal maddeler |
| TR201111589A2 (tr) * | 2011-03-03 | 2012-09-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür susuz kristal formu. |
| CZ304368B6 (cs) | 2011-11-28 | 2014-04-02 | Zentiva, K.S. | Směsný solvát tiotropium bromidu a způsob jeho přípravy |
| GB201200525D0 (en) | 2011-12-19 | 2012-02-29 | Teva Branded Pharmaceutical Prod R & D Inc | An inhalable medicament |
| 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 |
| UA115888C2 (uk) * | 2012-11-05 | 2018-01-10 | Зентіва, К.С. | Стабілізація сольватів тіотропію |
| KR20150135328A (ko) | 2013-04-01 | 2015-12-02 | 풀매트릭스 인코퍼레이티드 | 티오트로피움 건조 분말 |
| EP2913332A1 (en) | 2014-02-27 | 2015-09-02 | Euticals S.P.A. | Crystalline form of tiotropium bromide with lactose |
| US10034866B2 (en) | 2014-06-19 | 2018-07-31 | Teva Branded Pharmaceutical Products R&D, Inc. | Inhalable medicament comprising tiotropium |
| EP3414243A1 (en) * | 2016-02-11 | 2018-12-19 | Sima Patent Ve Lisanslama Hizmetleri Ltd. STI | Crystalline form of tiotropium bromide anhydrate |
| PT115583B (pt) | 2019-06-17 | 2022-05-02 | Hovione Farm S A | Processo contínuo para a preparação de medicamentos anticolinérgicos |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB845056A (en) | 1957-07-05 | 1960-08-17 | Egyt Gyogyszervegyeszeti Gyar | Improvements in or relating to tropane derivatives |
| DE1166787B (de) | 1960-07-09 | 1964-04-02 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von neuen Granatanol-(3ª‰)-estern und ihren Hydrohalogeniden |
| GB955535A (en) | 1962-10-22 | 1964-04-15 | Boehringer & Soehne Gmbh | New n-substituted norgranatanol-(3ª‰)-esters |
| DE2046659A1 (cg-RX-API-DMAC7.html) | 1970-01-28 | 1972-03-23 | ||
| US3808263A (en) * | 1970-05-12 | 1974-04-30 | Tanabe Seiyaku Co | 6,6-dimethyl-9-alkyl-9-azabicyclo(3.3.1)nonan-3-ols |
| US3673195A (en) * | 1970-05-25 | 1972-06-27 | Tanabe Seiyaku Co | Derivatives of 6,6,9-tri-lower alkyl-9-azabicyclo(3.3.1) nonan-3{60 -or 3{62 -ol |
| US4353922A (en) * | 1981-03-13 | 1982-10-12 | Syntex (U.S.A.) Inc. | Anticholinergic bronchodilators |
| US4570630A (en) | 1983-08-03 | 1986-02-18 | Miles Laboratories, Inc. | Medicament inhalation device |
| GR861995B (en) | 1985-07-30 | 1986-11-04 | Glaxo Group Ltd | Devices for administering medicaments to patients |
| DE3546218A1 (de) * | 1985-12-27 | 1987-07-02 | Madaus & Co Dr | Azoniaspironortropanolester, verfahren zu deren herstellung und pharmazeutisches mittel |
| US5610163A (en) * | 1989-09-16 | 1997-03-11 | Boehringer Ingelheim Gmbh | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
| 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 |
| US5770738A (en) * | 1992-03-05 | 1998-06-23 | Boehringer Ingelheim Kg | Esters of bi- and tricyclic amino alcohols, their preparation and their use in pharmaceutical compositions |
| ES2129117T3 (es) | 1992-12-09 | 1999-06-01 | Boehringer Ingelheim Pharma | Formulaciones en disolucion en forma de aerosol medicinales estabilizadas. |
| DE4318455A1 (de) | 1993-06-03 | 1994-12-08 | Boehringer Ingelheim Kg | Kapselhalterung |
| CN1150890C (zh) | 1998-08-04 | 2004-05-26 | 杰格研究股份公司 | 药用气溶胶制剂 |
| DE19921693A1 (de) * | 1999-05-12 | 2000-11-16 | Boehringer Ingelheim Pharma | Neuartige Arzneimittelkompositionen auf der Basis von anticholinergisch wirksamen Verbindungen und ß-Mimetika |
| MXPA02005666A (es) * | 2000-10-12 | 2002-11-29 | Boehringer Ingelheim Pharma | Nuevos polvos para anhalacion que contienen tiotropio. |
| IL155335A0 (en) | 2000-10-12 | 2003-11-23 | Boehringer Ingelheim Pharma | Crystalline monohydrate, method for producing the same and the use thereof in the production of a medicament |
| US6908928B2 (en) * | 2000-10-12 | 2005-06-21 | Bi Pharma Kg. | Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions |
| UA75375C2 (en) | 2000-10-12 | 2006-04-17 | Boehringer Ingelheim Pharma | Method for producing powdery preparations for inhaling |
| ME00244B (me) | 2000-10-31 | 2011-05-10 | Boehringer Ingelheim Pharma | Formulacija rastvora za inhalaciju sa soli tiotropijma |
| US20020111363A1 (en) * | 2000-10-31 | 2002-08-15 | Karin Drechsel | Inhalable formulation of a solution containing a tiotropium salt |
| US20020193392A1 (en) * | 2000-11-13 | 2002-12-19 | Christel Schmelzer | Pharmaceutical compositions based on tiotropium salts of salts of salmeterol |
| DE10056104A1 (de) | 2000-11-13 | 2002-05-23 | Boehringer Ingelheim Pharma | Neue Arzneimittelkompositionen auf der Basis von Tiotropiumsalzen und Salzen des Salmeterols |
| 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 |
| US20020193394A1 (en) * | 2001-03-13 | 2002-12-19 | Bernd Disse | Compounds for treating inflammatory diseases |
| DE10111843A1 (de) | 2001-03-13 | 2002-09-19 | Boehringer Ingelheim Pharma | Verbindungen zur Behandlung von inflammatorischen Erkrankungen |
| HRP20031066B1 (en) * | 2001-06-22 | 2011-10-31 | Boehringer Ingelheim Pharma Gmbh & Co.Kg. | Crystalline anticholinergic, method for its production, and use thereof in the production of a drug |
| 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 |
| GB0118373D0 (en) * | 2001-07-27 | 2001-09-19 | Glaxo Group Ltd | Novel therapeutic method |
| DE10200943A1 (de) * | 2002-01-12 | 2003-07-24 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Scopinestern |
| US20030229227A1 (en) * | 2002-03-16 | 2003-12-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New difurylglycolic acid esters, processes for the preparation thereof as well as the use thereof as pharmaceutical compositions |
| US7309707B2 (en) * | 2002-03-20 | 2007-12-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Crystalline micronisate, process for the manufacture thereof and use thereof for the preparation of a medicament |
| DE10212264A1 (de) | 2002-03-20 | 2003-10-02 | Boehringer Ingelheim Pharma | Kristallines Mikronisat, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung eines Arzneimittels |
| DE10214264A1 (de) * | 2002-03-28 | 2003-10-16 | Boehringer Ingelheim Pharma | HFA-Suspensionsformulierungen eines Anhydrats |
| US7244415B2 (en) * | 2002-03-28 | 2007-07-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | HFA suspension formulations of an anhydrate |
| US7311894B2 (en) * | 2002-03-28 | 2007-12-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | HFA suspension formulations containing an anticholinergic |
| PL375868A1 (en) * | 2002-12-16 | 2005-12-12 | Boehringer Ingelheim Pharma Gmbh & Co.Kg | Tiotropium containing hfc solution formulations |
| US7968717B2 (en) * | 2003-11-03 | 2011-06-28 | Boehringer Ingelhein International Gmbh | Crystalline anhydrate with anticholinergic efficacy |
| DE102004041253A1 (de) * | 2004-08-26 | 2006-03-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neues Verfahren zur Herstellung von Tiotropiumsalzen |
-
2006
- 2006-04-21 PL PL06754794T patent/PL1881980T3/pl unknown
- 2006-04-21 KR KR1020077028139A patent/KR20080012932A/ko not_active Ceased
- 2006-04-21 ES ES06754794T patent/ES2393794T3/es active Active
- 2006-04-21 AU AU2006243238A patent/AU2006243238B2/en not_active Ceased
- 2006-04-21 EP EP06754794A patent/EP1881980B1/en active Active
- 2006-04-21 CA CA002606549A patent/CA2606549A1/en not_active Abandoned
- 2006-04-21 WO PCT/EP2006/061763 patent/WO2006117299A2/en not_active Ceased
- 2006-04-21 CN CN2006800142275A patent/CN101166738B/zh active Active
- 2006-04-21 PT PT67547943T patent/PT1881980E/pt unknown
- 2006-04-21 DK DK06754794.3T patent/DK1881980T3/da active
- 2006-04-21 EP EP09157096A patent/EP2085396A3/en not_active Withdrawn
- 2006-04-21 BR BRPI0609295-0A patent/BRPI0609295A2/pt not_active IP Right Cessation
- 2006-04-21 NZ NZ563596A patent/NZ563596A/en not_active IP Right Cessation
- 2006-04-21 JP JP2008509408A patent/JP5227790B2/ja active Active
- 2006-04-21 RU RU2007144521/04A patent/RU2417224C2/ru active
- 2006-04-21 SI SI200631474T patent/SI1881980T1/sl unknown
- 2006-04-28 PE PE2006000456A patent/PE20061438A1/es not_active Application Discontinuation
- 2006-04-28 AR ARP060101714A patent/AR053599A1/es unknown
- 2006-04-28 UY UY29506A patent/UY29506A1/es not_active Application Discontinuation
- 2006-04-28 TW TW095115408A patent/TWI392674B/zh not_active IP Right Cessation
- 2006-05-01 US US11/381,076 patent/US7879871B2/en active Active
- 2006-12-07 MX MX2007013142A patent/MX2007013142A/es active IP Right Grant
-
2007
- 2007-09-19 ZA ZA200708048A patent/ZA200708048B/xx unknown
- 2007-10-31 IL IL187055A patent/IL187055A/en active IP Right Grant
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