JP2008543805A5 - - Google Patents
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- Publication number
- JP2008543805A5 JP2008543805A5 JP2008516267A JP2008516267A JP2008543805A5 JP 2008543805 A5 JP2008543805 A5 JP 2008543805A5 JP 2008516267 A JP2008516267 A JP 2008516267A JP 2008516267 A JP2008516267 A JP 2008516267A JP 2008543805 A5 JP2008543805 A5 JP 2008543805A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- binding
- crystalline tiotropium
- tiotropium
- ray powder
- 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
- 229940110309 tiotropium Drugs 0.000 claims 34
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class 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 30
- -1 substituted alkenyl sulfonate Chemical compound 0.000 claims 24
- 238000010586 diagram Methods 0.000 claims 20
- 239000000843 powder Substances 0.000 claims 20
- 239000013078 crystal Substances 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 238000012916 structural analysis Methods 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 5
- 150000001450 anions Chemical class 0.000 claims 5
- HVIDCXBJDYXPTO-JAZONYGRSA-M tiotropium salicylate Chemical compound OC(=O)C1=CC=CC=C1[O-].C([C@H]1[N+]([C@H](C2)[C@H]3[C@@H]1O3)(C)C)C2OC(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 HVIDCXBJDYXPTO-JAZONYGRSA-M 0.000 claims 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 230000002452 interceptive effect Effects 0.000 claims 4
- 150000004682 monohydrates Chemical class 0.000 claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 229940095064 tartrate Drugs 0.000 claims 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- OIXMUQLVDNPHNS-UHFFFAOYSA-N methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O OIXMUQLVDNPHNS-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 238000005245 sintering Methods 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- CAQZTSCRGMRSHX-TYYBGVCCSA-N (e)-but-2-enedioic acid;ethanol Chemical compound CCO.OC(=O)\C=C\C(O)=O CAQZTSCRGMRSHX-TYYBGVCCSA-N 0.000 claims 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 claims 1
- ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 claims 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- TWHXWYVOWJCXSI-UHFFFAOYSA-N phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O TWHXWYVOWJCXSI-UHFFFAOYSA-N 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05105270.2 | 2005-06-15 | ||
| EP05105270 | 2005-06-15 | ||
| PCT/EP2006/062688 WO2006134021A2 (en) | 2005-06-15 | 2006-05-30 | Process for preparing tiotropium salts, tiotropium salts as such and pharmaceutical compositions thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008543805A JP2008543805A (ja) | 2008-12-04 |
| JP2008543805A5 true JP2008543805A5 (https=) | 2009-07-16 |
| JP5315048B2 JP5315048B2 (ja) | 2013-10-16 |
Family
ID=35057150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008516267A Active JP5315048B2 (ja) | 2005-06-15 | 2006-05-30 | 新規チオトロピウム塩の製造方法、新規チオトロピウム塩及びその医薬組成物 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20060287530A1 (https=) |
| EP (1) | EP1896026B1 (https=) |
| JP (1) | JP5315048B2 (https=) |
| KR (1) | KR20080024532A (https=) |
| CN (1) | CN101227905A (https=) |
| AR (1) | AR057067A1 (https=) |
| AU (1) | AU2006259202B2 (https=) |
| BR (1) | BRPI0611763A2 (https=) |
| CA (1) | CA2611902C (https=) |
| IL (1) | IL188069A0 (https=) |
| MX (1) | MX2007015997A (https=) |
| NZ (2) | NZ564697A (https=) |
| RU (2) | RU2418796C2 (https=) |
| TW (1) | TW200718698A (https=) |
| WO (1) | WO2006134021A2 (https=) |
| ZA (1) | ZA200709331B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06004697A (es) * | 2003-11-03 | 2006-07-05 | Boehringer Ingelheim Int | Procedimiento para la preparacion de sales de tiotropio, sles de tiotropio, asi como formulaciones medicamentosas que las contienen. |
| AU2004285685B2 (en) * | 2003-11-03 | 2011-03-24 | Boehringer Ingelheim International Gmbh | Novel tiotropium salts, methods for the production thereof, and pharmaceutical formulations containing the same |
| 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 |
| WO2008101728A1 (de) * | 2007-02-23 | 2008-08-28 | K.H.S. Pharma Holding Gmbh | Verfahren zur herstellung von azoniaspironortropinestern und von nortropan-3-on verbindungen |
| GB0716026D0 (en) | 2007-08-16 | 2007-09-26 | Norton Healthcare Ltd | An inhalable medicament |
| WO2009031011A2 (en) * | 2007-09-05 | 2009-03-12 | Pfizer Limited | Xinafoate salt of n4-(2, 2-difluoro-4h-benz0 [1,4] 0xazin-3-one) -6-yl] -5-fluoro-n2- [3- (methylaminocar bonylmethyleneoxy) phenyl] 2, 4-pyrimidinediamine |
| PL388070A1 (pl) * | 2009-05-19 | 2010-11-22 | Adamed Spółka Z Ograniczoną Odpowiedzialnością | Nowe sole tiotropium |
| GB201200525D0 (en) | 2011-12-19 | 2012-02-29 | Teva Branded Pharmaceutical Prod R & D Inc | An inhalable medicament |
| CZ201241A3 (cs) | 2012-01-20 | 2013-07-31 | Zentiva, K.S. | Nové polymorfní formy tiotropium jodidu a zpusob jejich prípravy |
| US10034866B2 (en) | 2014-06-19 | 2018-07-31 | Teva Branded Pharmaceutical Products R&D, Inc. | Inhalable medicament comprising tiotropium |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3551492A (en) * | 1967-10-31 | 1970-12-29 | Ciba Geigy Corp | N,n'-diaminoalkoxy-benzyl-diamino-alkanes and the salts thereof |
| 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 |
| 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 |
| 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 |
| DE19528145A1 (de) * | 1995-08-01 | 1997-02-06 | Boehringer Ingelheim Kg | Neue Arzneimittel und ihre Verwendung |
| DE19921693A1 (de) * | 1999-05-12 | 2000-11-16 | Boehringer Ingelheim Pharma | Neuartige Arzneimittelkompositionen auf der Basis von anticholinergisch wirksamen Verbindungen und ß-Mimetika |
| ATE275391T1 (de) * | 2000-10-12 | 2004-09-15 | Boehringer Ingelheim Pharma | Neue tiotropium-haltige inhalationspulver |
| US6908928B2 (en) * | 2000-10-12 | 2005-06-21 | Bi Pharma Kg. | Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions |
| CN100519558C (zh) * | 2000-10-12 | 2009-07-29 | 贝林格尔英格海姆法玛两合公司 | 结晶单水合物、其制备方法及其在制备药物组合中的用途 |
| 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 |
| 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 |
| DE10111843A1 (de) * | 2001-03-13 | 2002-09-19 | Boehringer Ingelheim Pharma | Verbindungen zur Behandlung von inflammatorischen Erkrankungen |
| US20020193394A1 (en) * | 2001-03-13 | 2002-12-19 | Bernd Disse | Compounds for treating inflammatory diseases |
| 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 |
| 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 |
| US7311894B2 (en) * | 2002-03-28 | 2007-12-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | HFA suspension formulations containing an anticholinergic |
| WO2004064789A2 (en) * | 2003-01-16 | 2004-08-05 | University Of Rochester | Quaternary antimuscarinic compounds for the treatment of bladder diseases |
| AU2004285685B2 (en) * | 2003-11-03 | 2011-03-24 | Boehringer Ingelheim International Gmbh | Novel tiotropium salts, methods for the production thereof, and pharmaceutical formulations containing the same |
| MXPA06004697A (es) * | 2003-11-03 | 2006-07-05 | Boehringer Ingelheim Int | Procedimiento para la preparacion de sales de tiotropio, sles de tiotropio, asi como formulaciones medicamentosas que las contienen. |
| 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
- 2006-05-30 NZ NZ564697A patent/NZ564697A/en not_active IP Right Cessation
- 2006-05-30 CA CA2611902A patent/CA2611902C/en not_active Expired - Fee Related
- 2006-05-30 JP JP2008516267A patent/JP5315048B2/ja active Active
- 2006-05-30 CN CNA2006800215844A patent/CN101227905A/zh active Pending
- 2006-05-30 AU AU2006259202A patent/AU2006259202B2/en not_active Ceased
- 2006-05-30 WO PCT/EP2006/062688 patent/WO2006134021A2/en not_active Ceased
- 2006-05-30 MX MX2007015997A patent/MX2007015997A/es not_active Application Discontinuation
- 2006-05-30 KR KR1020087001206A patent/KR20080024532A/ko not_active Ceased
- 2006-05-30 BR BRPI0611763-5A patent/BRPI0611763A2/pt not_active IP Right Cessation
- 2006-05-30 NZ NZ583872A patent/NZ583872A/en not_active IP Right Cessation
- 2006-05-30 EP EP06763345.3A patent/EP1896026B1/en active Active
- 2006-05-30 RU RU2007148256/04A patent/RU2418796C2/ru not_active IP Right Cessation
- 2006-06-14 AR ARP060102507A patent/AR057067A1/es unknown
- 2006-06-14 TW TW095121214A patent/TW200718698A/zh unknown
- 2006-06-15 US US11/424,244 patent/US20060287530A1/en not_active Abandoned
-
2007
- 2007-10-30 ZA ZA200709331A patent/ZA200709331B/xx unknown
- 2007-12-12 IL IL188069A patent/IL188069A0/en unknown
-
2010
- 2010-09-15 RU RU2010138174/04A patent/RU2010138174A/ru not_active Application Discontinuation
-
2014
- 2014-07-03 US US14/323,361 patent/US20140316138A1/en not_active Abandoned
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