TWI363057B - Process for manufacturing 3(r)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide - Google Patents
Process for manufacturing 3(r)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide Download PDFInfo
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- TWI363057B TWI363057B TW096126654A TW96126654A TWI363057B TW I363057 B TWI363057 B TW I363057B TW 096126654 A TW096126654 A TW 096126654A TW 96126654 A TW96126654 A TW 96126654A TW I363057 B TWI363057 B TW I363057B
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- Prior art keywords
- solvent
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- hydroxy
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Links
- 238000000034 method Methods 0.000 title claims description 13
- XLAKJQPTOJHYDR-QTQXQZBYSA-M aclidinium bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3SC=CC=3)C=3SC=CC=3)[N+]21CCCOC1=CC=CC=C1 XLAKJQPTOJHYDR-QTQXQZBYSA-M 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002904 solvent Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000011877 solvent mixture Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- -1 3-phenoxypropyl Chemical group 0.000 claims 3
- BHUPIKYIGMWGAD-UHFFFAOYSA-N 2-amino-9-(hydroxymethyl)-3-oxophenoxazine-1-carboxylic acid Chemical compound C1=CC=C2OC3=CC(=O)C(N)=C(C(O)=O)C3=NC2=C1CO BHUPIKYIGMWGAD-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000006612 decyloxy group Chemical group 0.000 claims 1
- 230000035622 drinking Effects 0.000 claims 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 4
- NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring 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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
物與2’基·2’2_二嗟吩_2_基乙酸i•氮雜二環[2 2 辛·3⑻ 基酯為有利的。 在另一較佳實施例中，2_羥基_2,2_二噻吩_2基乙酸卜氮 雜一環[2_2.2]辛_3(R)基酯係懸浮（或溶解）於包含每莫耳2_ 經基-2,2_二售吩-2-基乙酸卜氮雜二環[2.2.2]辛-3(R)基醋介 於1.7公升溶劑與7公升溶劑之間的體積之溶劑或溶劑混合 物中。更佳該酯係懸浮（或溶解）於包含每莫耳酯介於丨公升 與7公升之間、更佳介於2公升與4公升之間之體積的 中。 在該等條件下，已證明使混合物反應不超過24小時、較 佳不長於12小時、更佳不長於9小時且最佳至多6小時之時 段為適當的β 當將2-羥基·2,2_二噻吩_2_基乙酸〖_氮雜二環[2 2义辛_ 3(R)基酯懸浮於每莫耳2_經基_2义二噻吩_2_基乙酸卜氣雜 一環[2.2.2]辛-3(R)基酯2 1至4 1之四氫呋喃中，將12當量 至1.3當量之3·苯氧基丙基溴化物添加至所得懸浮液中且將 混合物於惰性氣氛中在回流下攪拌至多9小時較佳至多6 小時時，獲得尤其良好的結果。 以下實例展示用於製備本發明之化合物之例示性方法， 且並非意欲限制本發明之範傳。 【實施方式】 實驗部分 比較性實例1(根據WO 01/04118) 將0.6 mmo丨之2·羥基_2,2_二噻吩·2·基乙酸丨·氮雜二環 122825.doc
Claims (1)
1363Ώ5 ^ 096126654號專利申請案 中文申請專利範圍替換本(99年l〇月） 十、申請專利範圍： 1. 一種藉由使2-羥基_2,2_二噻吩-2_基乙酸卜氮雜二環 [2.2.2]辛_3(R)基g旨與3_苯氧基丙基漠化物反應來製備 3(R)-(2-羥基-2,2-二噻吩-2-基乙醯氧基）_i_(3苯氧基丙 基）-1_氮鑌二環[2.2.2]辛烧漠化物的方法，其中該反應在 具有介於贼幻抓之間的沸點且選自由嗣及環趟組成 之群之溶劑或溶劑混合物中進行。 2·如請求们之方法’其中3·笨氧基丙基漠化物與2·經基_ 2曰，2-二噻吩_2·基乙酸卜氮雜二環[2 2 2]辛3⑻基酿之當 量比在1.0至3.0之範圍内。 月求項2之方法，其中該當量比係在μ至Μ之範圍 内。 4. 如請求項2之方法， 内。 其中該當量比係在1.2至1.3之範圍 5·=清求項1至4中任一項之方法，其中2-經基-2,2-二嗔 % 2基乙酸1_氮雜：環[2.22]辛_3(R)基㈣懸浮或溶解 於包含每莫耳2-經基-2,2•二售吩·2_基乙酸卜氮雜二環 L接2]辛_取)基§旨介於口公升溶劑與7公升溶劑之間的 積之溶劑或溶劑混合物中。 其中該溶劑體積包含每莫耳經基· ’"塞吩-2-基乙酸1_氛雜_ 八扎你 氮雜—環[2,2.2]辛-3(R)基酯介於2 公升與4公升之間。 如請求項1至4中任一 0了烷及四氫呋喃組成之群 m ^ 喝之方法，其中該溶劑係選自由丙 122825-99l012.doc 8. 8. *"""" ； Ή年ί。月（^9修正替換頁 9. 10. 11. 12. 叫求項7之方法，其中該办 如請求項1至4中杠一 ，合劑為四氫呋喃》 一項之方法，其中使該混合物反應不 超過24小時之時段。 如請求項9之方法，其中該時段為至多12小時 如凊求項H)之方法，其中該時段為至多9小時 如。月求項U之方法，其中該時段為至多6小時
l22825-991012.doc
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200601951A ES2298049B1 (es) | 2006-07-21 | 2006-07-21 | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200821307A TW200821307A (en) | 2008-05-16 |
| TWI363057B true TWI363057B (en) | 2012-05-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096126654A TWI363057B (en) | 2006-07-21 | 2007-07-20 | Process for manufacturing 3(r)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US8044205B2 (zh) |
| EP (1) | EP2044067B1 (zh) |
| JP (1) | JP5279708B2 (zh) |
| KR (1) | KR101410198B1 (zh) |
| CN (1) | CN101490048B (zh) |
| AR (1) | AR061933A1 (zh) |
| AT (1) | ATE449096T1 (zh) |
| AU (1) | AU2007276395B2 (zh) |
| BR (1) | BRPI0711500B1 (zh) |
| CA (1) | CA2657679C (zh) |
| CL (1) | CL2007002078A1 (zh) |
| CO (1) | CO6460740A2 (zh) |
| CY (1) | CY1109792T1 (zh) |
| DE (1) | DE602007003375D1 (zh) |
| DK (1) | DK2044067T3 (zh) |
| EC (1) | ECSP099033A (zh) |
| EG (1) | EG25727A (zh) |
| ES (2) | ES2298049B1 (zh) |
| HK (1) | HK1124051A1 (zh) |
| HR (1) | HRP20090652T1 (zh) |
| IL (1) | IL196324A (zh) |
| ME (1) | ME01773B (zh) |
| MX (1) | MX2009000573A (zh) |
| MY (1) | MY145285A (zh) |
| NO (1) | NO20090811L (zh) |
| NZ (1) | NZ573170A (zh) |
| PE (1) | PE20081307A1 (zh) |
| PL (1) | PL2044067T3 (zh) |
| PT (1) | PT2044067E (zh) |
| RS (1) | RS51264B (zh) |
| RU (1) | RU2439070C2 (zh) |
| SI (1) | SI2044067T1 (zh) |
| TW (1) | TWI363057B (zh) |
| UA (1) | UA96453C2 (zh) |
| UY (1) | UY30475A1 (zh) |
| WO (1) | WO2008009397A1 (zh) |
| ZA (1) | ZA200810051B (zh) |
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| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| CA2608561A1 (en) * | 2007-10-29 | 2009-04-29 | Carl Paluszkiewicz | Motorcycle wind deflector accessory support |
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| EP2100598A1 (en) * | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| EP2666465A1 (en) | 2012-05-25 | 2013-11-27 | Almirall, S.A. | Novel dosage and formulation |
| CZ306791B6 (cs) * | 2013-10-29 | 2017-07-12 | Zentiva, K.S. | Průmyslově využitelný způsob přípravy aklidinium bromidu o vysoké čistotě |
| CN103755699A (zh) * | 2014-01-06 | 2014-04-30 | 万特制药(海南)有限公司 | 一种2-羟基-2,2-二噻吩-2-基乙酸-1-氮杂二环[2,2,2]辛-3(r)-基酯制备方法 |
| CN103755698A (zh) * | 2014-01-06 | 2014-04-30 | 万特制药(海南)有限公司 | 一锅法制备阿地溴铵的工艺 |
| CZ2014188A3 (cs) | 2014-03-26 | 2015-10-07 | Zentiva, K.S. | Nové formy aclidinium chloridu a způsob jejich přípravy |
| CN104478871B (zh) * | 2014-12-26 | 2016-09-07 | 东华大学 | 一种胆碱m受体拮抗剂阿地溴铵及其制备方法 |
| PT108370B (pt) * | 2015-03-30 | 2018-10-25 | Hovione Farm S A | Processo de preparação de brometo de aclidínio |
| WO2016162878A1 (en) * | 2015-04-04 | 2016-10-13 | Harman Finochem Limited | An advantageous process for preparing 1-azoniabicyclo[2.2.2]octane,3-[(hydroxydi-2-thienylacetyl)oxy]-1-(3¬phenoxypropyl)-, bromide, (3r)- and its novel crystalline form-i |
| CZ2015257A3 (cs) | 2015-04-16 | 2016-10-26 | Zentiva, K.S. | Způsob pro zmenšování velikosti částic bromidu [(3R)-1-(3-fenoxypropyl)chinuklidin-1-ium-3-yl] 2-hydroxy-2,2-bis(2-thienyl)acetátu |
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| ES2204295B1 (es) * | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| ES2211315B1 (es) | 2002-11-12 | 2005-10-16 | Almirall Prodesfarma, S.A. | Nuevos compuestos triciclicos. |
| ES2211344B1 (es) | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US20050026887A1 (en) * | 2003-07-29 | 2005-02-03 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising an anticholinergic and a steroid |
| US20050026886A1 (en) * | 2003-07-29 | 2005-02-03 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising an anticholinergic and a PDE IV inhibitor |
| US20050026948A1 (en) * | 2003-07-29 | 2005-02-03 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising an anticholinergic and a betamimetic |
| BRPI0413054A (pt) | 2003-07-29 | 2006-10-17 | Boehringer Ingelheim Int | combinação de um anticolinérgico e um esteróide e seu uso no tratamento de distúrbios respiratórios por inalação |
| US20050025718A1 (en) * | 2003-07-31 | 2005-02-03 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising an anticholinergic and a betamimetic |
| ES2232306B1 (es) | 2003-11-10 | 2006-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2239546B1 (es) * | 2004-03-15 | 2006-12-01 | Almirall Prodesfarma, S.A. | Nuevos esteres de quinuclidina cuaternizados. |
| ES2257152B1 (es) | 2004-05-31 | 2007-07-01 | Laboratorios Almirall S.A. | Combinaciones que comprenden agentes antimuscarinicos y agonistas beta-adrenergicos. |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) * | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
-
2006
- 2006-07-21 ES ES200601951A patent/ES2298049B1/es not_active Withdrawn - After Issue
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2007
- 2007-07-09 UY UY30475A patent/UY30475A1/es unknown
- 2007-07-16 CA CA2657679A patent/CA2657679C/en active Active
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- 2007-07-16 JP JP2009519845A patent/JP5279708B2/ja active Active
- 2007-07-16 RU RU2009105827/04A patent/RU2439070C2/ru active
- 2007-07-16 US US12/374,185 patent/US8044205B2/en active Active
- 2007-07-16 KR KR1020097001067A patent/KR101410198B1/ko active IP Right Grant
- 2007-07-16 UA UAA200901336A patent/UA96453C2/uk unknown
- 2007-07-16 DK DK07786080.7T patent/DK2044067T3/da active
- 2007-07-16 SI SI200730159T patent/SI2044067T1/sl unknown
- 2007-07-16 CN CN2007800274230A patent/CN101490048B/zh active Active
- 2007-07-16 MY MYPI20090241A patent/MY145285A/en unknown
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- 2007-07-16 AU AU2007276395A patent/AU2007276395B2/en active Active
- 2007-07-16 NZ NZ573170A patent/NZ573170A/en unknown
- 2007-07-16 AT AT07786080T patent/ATE449096T1/de active
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- 2007-07-16 DE DE602007003375T patent/DE602007003375D1/de active Active
- 2007-07-16 EP EP07786080A patent/EP2044067B1/en active Active
- 2007-07-16 MX MX2009000573A patent/MX2009000573A/es active IP Right Grant
- 2007-07-16 PT PT07786080T patent/PT2044067E/pt unknown
- 2007-07-16 ES ES07786080T patent/ES2336045T3/es active Active
- 2007-07-16 BR BRPI0711500-8A patent/BRPI0711500B1/pt active IP Right Grant
- 2007-07-16 ME MEP-2010-9A patent/ME01773B/me unknown
- 2007-07-17 CL CL2007002078A patent/CL2007002078A1/es unknown
- 2007-07-18 PE PE2007000929A patent/PE20081307A1/es not_active Application Discontinuation
- 2007-07-19 AR ARP070103217A patent/AR061933A1/es unknown
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