ES2613952T3 - Nuevo procedimiento para preparar sales de tiotropio - Google Patents
Nuevo procedimiento para preparar sales de tiotropio Download PDFInfo
- Publication number
- ES2613952T3 ES2613952T3 ES06777919.9T ES06777919T ES2613952T3 ES 2613952 T3 ES2613952 T3 ES 2613952T3 ES 06777919 T ES06777919 T ES 06777919T ES 2613952 T3 ES2613952 T3 ES 2613952T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- group
- tiotropium salts
- kat
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title abstract 2
- 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 abstract 2
- -1 hexafluorophosphate Chemical compound 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000001450 anions Chemical class 0.000 abstract 2
- 102000004882 Lipase Human genes 0.000 abstract 1
- 108090001060 Lipase Proteins 0.000 abstract 1
- 239000004367 Lipase Substances 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 235000019421 lipase Nutrition 0.000 abstract 1
- 150000002892 organic cations Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229960002317 succinimide Drugs 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 239000010457 zeolite 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- 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
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Procedimiento para preparar sales de tiotropio de la fórmula 1**Fórmula** en donde X‾ puede significar un anión con carga negativa sencilla, caracterizado por que se hace reaccionar un compuesto de la fórmula 2**Fórmula** en donde Y‾ puede significar un anión lipófilo con carga negativa sencilla, distinto de X‾ , seleccionado del grupo consistente en hexafluorofosfato, tetrafluoroborato y tetrafenilborato, de manera especialmente preferible hexafluorofosfato o tetrafenilborato, en un solo paso, con un compuesto de la fórmula 3**Fórmula** en donde R significa un radical seleccionado del grupo consistente en metoxi, etoxi, propoxi, isopropoxi, isopropeniloxi, butoxi, O-N-succinimida, O-N-ftalimida, feniloxi, nitrofeniloxi, fluorofeniloxi, pentafluorofeniloxi, viniloxi, 2-aliloxi, -S-metilo, -S-etilo y -S-fenilo, en un disolvente adecuado y con adición de una base adecuada y un catalizador seleccionado del grupo consistente en zeolitas, alcóxidos, lipasas y aminas terciarias, para proporcionar un compuesto de la fórmula 4**Fórmula** pudiendo tener el grupo Y‾ los significados antes indicados, y se transforma el compuesto de la fórmula 4, sin aislamiento, mediante reacción con una sal Kat+X‾ , en donde Kat+ representa un catión seleccionado del grupo consistente en Li+, Na+, K+, Mg2+, Ca2+ y cationes orgánicos con N cuaternario y X‾ puede tener los significados antes indicados, en el compuesto de la fórmula 1.
Description
Claims (1)
-
imagen1 imagen2 imagen3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005035112 | 2005-07-27 | ||
| DE102005035112A DE102005035112A1 (de) | 2005-07-27 | 2005-07-27 | Neues Verfahren zur Herstellung von Tiotropiumsalzen unter Anwendung von in organischen Lösungsmitteln löslichen N-Methylscopiniumsalzen |
| PCT/EP2006/064559 WO2007012626A2 (de) | 2005-07-27 | 2006-07-24 | Neues verfahren zur herstellung von tiotropiumsalzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2613952T3 true ES2613952T3 (es) | 2017-05-29 |
Family
ID=37110331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06777919.9T Active ES2613952T3 (es) | 2005-07-27 | 2006-07-24 | Nuevo procedimiento para preparar sales de tiotropio |
Country Status (24)
| Country | Link |
|---|---|
| US (5) | US20070027320A1 (es) |
| EP (2) | EP1910354B1 (es) |
| JP (1) | JP5210861B2 (es) |
| KR (1) | KR101299929B1 (es) |
| CN (2) | CN101309920A (es) |
| AR (1) | AR057690A1 (es) |
| AU (1) | AU2006274012B2 (es) |
| BR (1) | BRPI0614062B8 (es) |
| CA (1) | CA2616222C (es) |
| DE (1) | DE102005035112A1 (es) |
| DK (1) | DK1910354T3 (es) |
| EA (1) | EA014271B1 (es) |
| EC (1) | ECSP088138A (es) |
| ES (1) | ES2613952T3 (es) |
| HU (1) | HUE032259T2 (es) |
| IL (1) | IL188989A (es) |
| MX (1) | MX2008001093A (es) |
| NO (2) | NO340877B1 (es) |
| NZ (1) | NZ566039A (es) |
| PL (1) | PL1910354T3 (es) |
| TW (3) | TWI486345B (es) |
| UA (1) | UA94914C2 (es) |
| WO (1) | WO2007012626A2 (es) |
| ZA (1) | ZA200711113B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008089852A1 (de) * | 2007-01-26 | 2008-07-31 | Boehringer Ingelheim Pharma Gmbh & Co.Kg | Neues verfahren zur herstellung von tiotropiumsalzen |
| EP1953156A1 (de) * | 2007-01-29 | 2008-08-06 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung von Scopiniumsalzen |
| EP1950196A1 (de) * | 2007-01-29 | 2008-07-30 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung von Ammoniumhexafluorophosphaten |
| EP1997819A1 (de) * | 2007-05-25 | 2008-12-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung von Scopinestern |
| EP2036898A2 (de) * | 2007-09-13 | 2009-03-18 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung von 1,3-Dioxolan-2Onen sowie von Carbonsäureestern durch Transacylierung unter Basischen Reaktionsbedingungen |
| JP6087492B2 (ja) * | 2008-01-10 | 2017-03-01 | ジェネリクス・［ユーケー］・リミテッド | スコピンエステルを調製するための新規プロセス |
| EP2462140A2 (en) | 2009-08-07 | 2012-06-13 | Generics [UK] Limited | Anhydrate of triotropium bromide |
| WO2011015884A1 (en) * | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Process to prepare scopine esters |
| CZ305012B6 (cs) * | 2012-03-30 | 2015-03-25 | Zentiva, K.S. | Způsob přípravy skopinesteru kyseliny di(2-thienyl)glykolové, intermediátu v syntéze tiotropium bromidu |
| WO2021133280A1 (en) * | 2019-12-27 | 2021-07-01 | Deva Holding | An improved process for preparation of scopine hydrobromide |
Family Cites Families (18)
| 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 |
| US7441045B2 (en) * | 1999-12-13 | 2008-10-21 | F5 Networks, Inc. | Method and system for balancing load distribution on a wide area network |
| US6934686B1 (en) | 2000-06-30 | 2005-08-23 | I2 Technologies Us, Inc. | Warranty transaction system and method |
| US7574499B1 (en) * | 2000-07-19 | 2009-08-11 | Akamai Technologies, Inc. | Global traffic management system using IP anycast routing and dynamic load-balancing |
| US6706726B2 (en) * | 2000-10-14 | 2004-03-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anticholinergics which may be used as medicaments as well as processes for preparing them |
| 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 |
| US7237017B1 (en) * | 2001-03-13 | 2007-06-26 | Panamsat Corporation | Micronode in a satellite based content delivery system |
| US20020143798A1 (en) * | 2001-04-02 | 2002-10-03 | Akamai Technologies, Inc. | Highly available distributed storage system for internet content with storage site redirection |
| JP2004530705A (ja) * | 2001-05-25 | 2004-10-07 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | 閉塞性気道疾患及びその他の炎症性疾患を治療するためのｐｄｅ４インヒビター及びチオトロピウム又はその誘導体の組み合わせ |
| WO2003027906A2 (en) * | 2001-09-28 | 2003-04-03 | Savvis Communications Corporation | System and method for policy dependent name to address resolutioin. |
| DE10200943A1 (de) * | 2002-01-12 | 2003-07-24 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Scopinestern |
| US7305429B2 (en) * | 2002-06-10 | 2007-12-04 | Utstarcom, Inc. | Method and apparatus for global server load balancing |
| EP1504756A1 (en) * | 2003-08-06 | 2005-02-09 | Kyowa Hakko Kogyo Co., Ltd | Medicament compositions comprising a heterocyclic compound and an anticholinergic |
| ATE478071T1 (de) * | 2003-11-03 | 2010-09-15 | Boehringer Ingelheim Int | Verfahren zur herstellung neuer tiotropiumsalze |
| HRP20100149T1 (hr) * | 2003-11-03 | 2010-04-30 | Boehringer Ingelheim International Gmbh | Postupak priprave tiotropijevih soli |
| DE102004041253A1 (de) * | 2004-08-26 | 2006-03-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neues Verfahren zur Herstellung von Tiotropiumsalzen |
| CN101227905A (zh) * | 2005-06-15 | 2008-07-23 | 贝林格尔·英格海姆国际有限公司 | 制备噻托铵盐的方法、噻托铵盐及其药物组合物 |
-
2005
- 2005-07-27 DE DE102005035112A patent/DE102005035112A1/de not_active Withdrawn
-
2006
- 2006-07-24 EA EA200800324A patent/EA014271B1/ru not_active IP Right Cessation
- 2006-07-24 CN CNA2006800257279A patent/CN101309920A/zh active Pending
- 2006-07-24 PL PL06777919T patent/PL1910354T3/pl unknown
- 2006-07-24 BR BRPI0614062A patent/BRPI0614062B8/pt active IP Right Grant
- 2006-07-24 HU HUE06777919A patent/HUE032259T2/en unknown
- 2006-07-24 ES ES06777919.9T patent/ES2613952T3/es active Active
- 2006-07-24 UA UAA200802325A patent/UA94914C2/ru unknown
- 2006-07-24 JP JP2008523343A patent/JP5210861B2/ja active Active
- 2006-07-24 WO PCT/EP2006/064559 patent/WO2007012626A2/de not_active Ceased
- 2006-07-24 CN CN201410719910.5A patent/CN104356129A/zh active Pending
- 2006-07-24 DK DK06777919.9T patent/DK1910354T3/en active
- 2006-07-24 NZ NZ566039A patent/NZ566039A/en unknown
- 2006-07-24 AU AU2006274012A patent/AU2006274012B2/en active Active
- 2006-07-24 CA CA2616222A patent/CA2616222C/en not_active Expired - Fee Related
- 2006-07-24 EP EP06777919.9A patent/EP1910354B1/de active Active
- 2006-07-24 EP EP16197435.7A patent/EP3153512A1/de not_active Withdrawn
- 2006-07-24 MX MX2008001093A patent/MX2008001093A/es active IP Right Grant
- 2006-07-24 US US11/459,457 patent/US20070027320A1/en not_active Abandoned
- 2006-07-24 KR KR1020087004605A patent/KR101299929B1/ko active Active
- 2006-07-26 AR ARP060103225A patent/AR057690A1/es not_active Application Discontinuation
- 2006-07-26 TW TW103103865A patent/TWI486345B/zh active
- 2006-07-26 TW TW095127339A patent/TWI443097B/zh active
- 2006-07-26 TW TW103103866A patent/TWI486346B/zh active
-
2007
- 2007-12-20 ZA ZA200711113A patent/ZA200711113B/xx unknown
- 2007-12-28 NO NO20076681A patent/NO340877B1/no unknown
-
2008
- 2008-01-24 IL IL188989A patent/IL188989A/en active IP Right Grant
- 2008-01-25 EC EC2008008138A patent/ECSP088138A/es unknown
-
2010
- 2010-04-29 US US12/769,927 patent/US20100210844A1/en not_active Abandoned
-
2012
- 2012-12-27 US US13/727,799 patent/US20130116435A1/en not_active Abandoned
-
2014
- 2014-07-07 US US14/324,610 patent/US20140323732A1/en not_active Abandoned
-
2015
- 2015-04-23 US US14/694,155 patent/US20150225395A1/en not_active Abandoned
-
2017
- 2017-04-11 NO NO20170613A patent/NO20170613A1/no not_active Application Discontinuation
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