RU2418796C2 - Способ получения новых солей тиотропия - Google Patents
Способ получения новых солей тиотропия Download PDFInfo
- Publication number
- RU2418796C2 RU2418796C2 RU2007148256/04A RU2007148256A RU2418796C2 RU 2418796 C2 RU2418796 C2 RU 2418796C2 RU 2007148256/04 A RU2007148256/04 A RU 2007148256/04A RU 2007148256 A RU2007148256 A RU 2007148256A RU 2418796 C2 RU2418796 C2 RU 2418796C2
- Authority
- RU
- Russia
- Prior art keywords
- group
- alkyl
- coo
- hso
- alkenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 12
- 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 title claims abstract 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract 6
- 150000001450 anions Chemical class 0.000 claims abstract 6
- 229940110309 tiotropium Drugs 0.000 claims abstract 5
- 239000002904 solvent Substances 0.000 claims abstract 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- -1 for example Chemical class 0.000 claims 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 150000004767 nitrides Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
-
- 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
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05105270 | 2005-06-15 | ||
| EP05105270.2 | 2005-06-15 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010138174/04A Division RU2010138174A (ru) | 2005-06-15 | 2010-09-15 | Способ получения новых солей тиотропия, новые соли тиотропия как таковые и в качестве фармацевтических композиций |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007148256A RU2007148256A (ru) | 2009-07-20 |
| RU2418796C2 true RU2418796C2 (ru) | 2011-05-20 |
Family
ID=35057150
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007148256/04A RU2418796C2 (ru) | 2005-06-15 | 2006-05-30 | Способ получения новых солей тиотропия |
| RU2010138174/04A RU2010138174A (ru) | 2005-06-15 | 2010-09-15 | Способ получения новых солей тиотропия, новые соли тиотропия как таковые и в качестве фармацевтических композиций |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010138174/04A RU2010138174A (ru) | 2005-06-15 | 2010-09-15 | Способ получения новых солей тиотропия, новые соли тиотропия как таковые и в качестве фармацевтических композиций |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20060287530A1 (enExample) |
| EP (1) | EP1896026B1 (enExample) |
| JP (1) | JP5315048B2 (enExample) |
| KR (1) | KR20080024532A (enExample) |
| CN (1) | CN101227905A (enExample) |
| AR (1) | AR057067A1 (enExample) |
| AU (1) | AU2006259202B2 (enExample) |
| BR (1) | BRPI0611763A2 (enExample) |
| CA (1) | CA2611902C (enExample) |
| IL (1) | IL188069A0 (enExample) |
| MX (1) | MX2007015997A (enExample) |
| NZ (2) | NZ564697A (enExample) |
| RU (2) | RU2418796C2 (enExample) |
| TW (1) | TW200718698A (enExample) |
| WO (1) | WO2006134021A2 (enExample) |
| ZA (1) | ZA200709331B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2336126A1 (de) * | 2003-11-03 | 2011-06-22 | Boehringer Ingelheim International GmbH | Tiotropiumsalze, Verfahren zu deren Herstellung und Arzneimittelformulierungen diese enthaltend |
| JP5165245B2 (ja) * | 2003-11-03 | 2013-03-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規なチオトロピウム塩、その製造方法及びチオトロピウム塩を含有する医薬組成物 |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2171258C2 (ru) * | 1995-08-01 | 2001-07-27 | Берингер Ингельхайм КГ | Бромид l-(-)-энантиомера(эндо,син)-(-)-3-(3-окси-1-оксо-2-фенилпропокси)-8-метил- 8-(1-метилэтил)-8-азони-абицикло[3.2.1]октана с чистотой 90-100% и ингаляционный препарат для ингибирования бронхоспазма, вызванного ацетилхолином |
| WO2004064789A2 (en) * | 2003-01-16 | 2004-08-05 | University Of Rochester | Quaternary antimuscarinic compounds for the treatment of bladder diseases |
Family Cites Families (26)
| 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 |
| DE19921693A1 (de) * | 1999-05-12 | 2000-11-16 | Boehringer Ingelheim Pharma | Neuartige Arzneimittelkompositionen auf der Basis von anticholinergisch wirksamen Verbindungen und ß-Mimetika |
| US6908928B2 (en) * | 2000-10-12 | 2005-06-21 | Bi Pharma Kg. | Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions |
| AU1499602A (en) * | 2000-10-12 | 2002-04-22 | Boehringer Ingelheim Pharma | Crystalline monohydrate, method for producing the same and the use thereof in the production of a medicament |
| IL149984A0 (en) * | 2000-10-12 | 2002-12-01 | Boehringer Ingelheim Pharma | Novel tiotropium-containing inhalation powder |
| 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 |
| JP5165245B2 (ja) * | 2003-11-03 | 2013-03-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規なチオトロピウム塩、その製造方法及びチオトロピウム塩を含有する医薬組成物 |
| EP2336126A1 (de) * | 2003-11-03 | 2011-06-22 | Boehringer Ingelheim International GmbH | Tiotropiumsalze, Verfahren zu deren Herstellung und Arzneimittelformulierungen diese enthaltend |
| 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 AU AU2006259202A patent/AU2006259202B2/en not_active Ceased
- 2006-05-30 NZ NZ564697A patent/NZ564697A/en not_active IP Right Cessation
- 2006-05-30 EP EP06763345.3A patent/EP1896026B1/en active Active
- 2006-05-30 MX MX2007015997A patent/MX2007015997A/es not_active Application Discontinuation
- 2006-05-30 WO PCT/EP2006/062688 patent/WO2006134021A2/en not_active Ceased
- 2006-05-30 CN CNA2006800215844A patent/CN101227905A/zh active Pending
- 2006-05-30 JP JP2008516267A patent/JP5315048B2/ja active Active
- 2006-05-30 RU RU2007148256/04A patent/RU2418796C2/ru not_active IP Right Cessation
- 2006-05-30 CA CA2611902A patent/CA2611902C/en not_active Expired - Fee Related
- 2006-05-30 NZ NZ583872A patent/NZ583872A/en not_active IP Right Cessation
- 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
- 2006-06-14 TW TW095121214A patent/TW200718698A/zh unknown
- 2006-06-14 AR ARP060102507A patent/AR057067A1/es 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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2171258C2 (ru) * | 1995-08-01 | 2001-07-27 | Берингер Ингельхайм КГ | Бромид l-(-)-энантиомера(эндо,син)-(-)-3-(3-окси-1-оксо-2-фенилпропокси)-8-метил- 8-(1-метилэтил)-8-азони-абицикло[3.2.1]октана с чистотой 90-100% и ингаляционный препарат для ингибирования бронхоспазма, вызванного ацетилхолином |
| WO2004064789A2 (en) * | 2003-01-16 | 2004-08-05 | University Of Rochester | Quaternary antimuscarinic compounds for the treatment of bladder diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007015997A (es) | 2008-03-07 |
| AU2006259202A1 (en) | 2006-12-21 |
| NZ583872A (en) | 2011-10-28 |
| TW200718698A (en) | 2007-05-16 |
| RU2010138174A (ru) | 2012-03-20 |
| CA2611902C (en) | 2013-08-27 |
| AU2006259202B2 (en) | 2012-05-10 |
| KR20080024532A (ko) | 2008-03-18 |
| WO2006134021A2 (en) | 2006-12-21 |
| WO2006134021A3 (en) | 2007-04-19 |
| US20140316138A1 (en) | 2014-10-23 |
| EP1896026A2 (en) | 2008-03-12 |
| NZ564697A (en) | 2010-04-30 |
| US20060287530A1 (en) | 2006-12-21 |
| JP2008543805A (ja) | 2008-12-04 |
| ZA200709331B (en) | 2008-10-29 |
| EP1896026B1 (en) | 2013-10-09 |
| IL188069A0 (en) | 2008-03-20 |
| AR057067A1 (es) | 2007-11-14 |
| RU2007148256A (ru) | 2009-07-20 |
| CN101227905A (zh) | 2008-07-23 |
| BRPI0611763A2 (pt) | 2010-09-28 |
| JP5315048B2 (ja) | 2013-10-16 |
| CA2611902A1 (en) | 2006-12-21 |
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| Publication | Publication Date | Title |
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