JP2011509284A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011509284A5 JP2011509284A5 JP2010541849A JP2010541849A JP2011509284A5 JP 2011509284 A5 JP2011509284 A5 JP 2011509284A5 JP 2010541849 A JP2010541849 A JP 2010541849A JP 2010541849 A JP2010541849 A JP 2010541849A JP 2011509284 A5 JP2011509284 A5 JP 2011509284A5
- Authority
- JP
- Japan
- Prior art keywords
- base
- alkyl
- scopine
- aryl
- iii
- 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
- 238000000034 method Methods 0.000 claims 10
- 239000002585 base Substances 0.000 claims 9
- 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 8
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical group 0.000 claims 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 claims 5
- 229960000257 tiotropium bromide Drugs 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- -1 scopine ester Chemical class 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000005025 alkynylaryl group Chemical group 0.000 claims 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- 229940110309 tiotropium Drugs 0.000 claims 3
- 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 3
- 238000005809 transesterification reaction Methods 0.000 claims 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 229940112141 dry powder inhaler Drugs 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical group CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940071648 metered dose inhaler Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000006199 nebulizer Substances 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN77/KOL/2008 | 2008-01-10 | ||
| IN77KO2008 | 2008-01-10 | ||
| PCT/GB2009/050014 WO2009087419A1 (en) | 2008-01-10 | 2009-01-09 | Novel process for the preparation of scopine esters |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014165472A Division JP5902774B2 (ja) | 2008-01-10 | 2014-08-15 | スコピンエステルを調製するための新規プロセス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509284A JP2011509284A (ja) | 2011-03-24 |
| JP2011509284A5 true JP2011509284A5 (enExample) | 2012-02-23 |
| JP6087492B2 JP6087492B2 (ja) | 2017-03-01 |
Family
ID=40451439
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010541849A Expired - Fee Related JP6087492B2 (ja) | 2008-01-10 | 2009-01-09 | スコピンエステルを調製するための新規プロセス |
| JP2014165472A Expired - Fee Related JP5902774B2 (ja) | 2008-01-10 | 2014-08-15 | スコピンエステルを調製するための新規プロセス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014165472A Expired - Fee Related JP5902774B2 (ja) | 2008-01-10 | 2014-08-15 | スコピンエステルを調製するための新規プロセス |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20110028508A1 (enExample) |
| EP (1) | EP2240477B8 (enExample) |
| JP (2) | JP6087492B2 (enExample) |
| CN (2) | CN101918401A (enExample) |
| AU (1) | AU2009203579B2 (enExample) |
| CA (1) | CA2710523C (enExample) |
| CY (1) | CY1116076T1 (enExample) |
| DK (1) | DK2240477T3 (enExample) |
| ES (1) | ES2523695T3 (enExample) |
| HR (1) | HRP20141004T1 (enExample) |
| PL (1) | PL2240477T3 (enExample) |
| PT (1) | PT2240477E (enExample) |
| SI (1) | SI2240477T1 (enExample) |
| WO (1) | WO2009087419A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080051582A1 (en) | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| WO2011015884A1 (en) | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Process to prepare scopine esters |
| US8697719B2 (en) | 2009-08-07 | 2014-04-15 | Generics [Uk] Limited | Anhydrate of tiotropium bromide |
| WO2011095800A2 (en) | 2010-02-02 | 2011-08-11 | Generics [Uk] Limited | Analytical methods |
| TR201005222A2 (tr) * | 2010-04-01 | 2011-10-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür sentez yöntemi |
| TR201005221A2 (tr) * | 2010-04-01 | 2012-01-23 | Bi̇lgi̇ç Mahmut | Geliştirilmiş sentez metodu. |
| US8957209B2 (en) | 2010-04-01 | 2015-02-17 | Mahmut Bilgic | Methods for the synthesis of tiotropium bromide |
| TR201002520A2 (tr) * | 2010-04-01 | 2010-05-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür imalat metodu. |
| CN101979391B (zh) * | 2010-11-16 | 2013-06-05 | 济南德信佳生物科技有限公司 | 一种噻托溴铵的制备方法 |
| US8680297B2 (en) * | 2011-10-06 | 2014-03-25 | Drug Process Licensing Assoc., LLC | Manufacturing process for tiotropium bromide |
| PT106142B (pt) | 2012-02-10 | 2014-07-18 | Hovione Farmaci Ncia S A | Processo para a preparação de brometo de tiotrópio |
| CZ304808B6 (cs) | 2012-03-16 | 2014-11-05 | Zentiva, K.S. | Způsob přípravy skopinesteru kyseliny di(2-thienyl)glykolové, intermediátu v syntéze tiotropium bromidu a jeho nová forma |
| CZ305012B6 (cs) | 2012-03-30 | 2015-03-25 | Zentiva, K.S. | Způsob přípravy skopinesteru kyseliny di(2-thienyl)glykolové, intermediátu v syntéze tiotropium bromidu |
| WO2014140318A1 (en) * | 2013-03-14 | 2014-09-18 | K.H.S. Pharma Holding Gmbh | Improved process for acyl transfer reactions |
| CN117486893B (zh) * | 2023-12-29 | 2024-03-12 | 北京中医药大学深圳医院(龙岗) | anti-pso B及其在制备预防和/或治疗银屑病的药物中的应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6908928B2 (en) * | 2000-10-12 | 2005-06-21 | Bi Pharma Kg. | Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions |
| 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 |
| AUPR315301A0 (en) * | 2001-02-19 | 2001-03-15 | Silverbrook Research Pty. Ltd. | An Apparatus (ART102) |
| 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 |
| US6610849B2 (en) * | 2001-06-28 | 2003-08-26 | Boehringer Ingelheim Pharma Kg | Process for the manufacture of tropenol |
| DE10200943A1 (de) * | 2002-01-12 | 2003-07-24 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Scopinestern |
| US6747153B2 (en) * | 2002-05-31 | 2004-06-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Industrial process for preparing tropenol |
| ATE435862T1 (de) * | 2003-05-28 | 2009-07-15 | Theravance Inc | Azabicycloalkanverbindungen als muscarinrezeptor antagonisten |
| US7968717B2 (en) * | 2003-11-03 | 2011-06-28 | Boehringer Ingelhein International Gmbh | Crystalline anhydrate with anticholinergic efficacy |
| CA2606549A1 (en) * | 2005-05-02 | 2006-11-09 | Boehringer Ingelheim International Gmbh | Crystalline forms of tiotropium bromide |
| 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 |
| CN102731494A (zh) * | 2005-12-19 | 2012-10-17 | 西科尔公司 | 噻托溴铵的新形式及其制备方法 |
| US20070167480A1 (en) * | 2005-12-19 | 2007-07-19 | Sicor Inc. | Pure and stable tiotropium bromide |
| US20080051582A1 (en) * | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| WO2008089852A1 (de) * | 2007-01-26 | 2008-07-31 | Boehringer Ingelheim Pharma Gmbh & Co.Kg | Neues verfahren zur herstellung von tiotropiumsalzen |
| WO2008104955A1 (en) * | 2007-02-28 | 2008-09-04 | Ranbaxy Laboratories Limited | Azoniatricyclo [3.3.1.0] nonane derivatives as muscarinic receptor antagonists |
-
2009
- 2009-01-09 PT PT97010425T patent/PT2240477E/pt unknown
- 2009-01-09 EP EP09701042.5A patent/EP2240477B8/en active Active
- 2009-01-09 SI SI200931062T patent/SI2240477T1/sl unknown
- 2009-01-09 CN CN2009801017774A patent/CN101918401A/zh active Pending
- 2009-01-09 HR HRP20141004AT patent/HRP20141004T1/hr unknown
- 2009-01-09 JP JP2010541849A patent/JP6087492B2/ja not_active Expired - Fee Related
- 2009-01-09 US US12/810,231 patent/US20110028508A1/en not_active Abandoned
- 2009-01-09 DK DK09701042.5T patent/DK2240477T3/en active
- 2009-01-09 AU AU2009203579A patent/AU2009203579B2/en not_active Ceased
- 2009-01-09 ES ES09701042.5T patent/ES2523695T3/es active Active
- 2009-01-09 CN CN201610056741.0A patent/CN105601628A/zh active Pending
- 2009-01-09 WO PCT/GB2009/050014 patent/WO2009087419A1/en not_active Ceased
- 2009-01-09 PL PL09701042T patent/PL2240477T3/pl unknown
- 2009-01-09 CA CA2710523A patent/CA2710523C/en not_active Expired - Fee Related
-
2014
- 2014-08-15 JP JP2014165472A patent/JP5902774B2/ja not_active Expired - Fee Related
- 2014-11-11 CY CY20141100937T patent/CY1116076T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011509284A5 (enExample) | ||
| JP5902774B2 (ja) | スコピンエステルを調製するための新規プロセス | |
| CA2296313C (en) | 2-aminopyridines containing fused ring substituents as nos inhibitors | |
| US20090124636A1 (en) | Chemical compounds | |
| JP5753790B2 (ja) | ８−アザビシクロ［３．２．１］オクタン−８−カルボキサミド誘導体 | |
| HRP970174A2 (en) | 6-phenylpyridil-2-amine derivatives | |
| TN2012000139A1 (en) | Cgrp receptor antagonists | |
| EA034868B1 (ru) | Пиридазиноновые соединения и их применение | |
| TW200304824A (en) | Nicotinamide derivatives useful as PDE4 inhibitors | |
| MX2010012189A (es) | Derivados de quinuclidina como antagonistas del receptor m3 muscarinico. | |
| HRP20191339T1 (hr) | Novi anelirani fenoksiacetamidi | |
| JP2012532191A5 (enExample) | ||
| US20160229807A1 (en) | New phenyl-dihydropyridine derivatives as aldosterone synthase inhibitors | |
| WO2011015884A1 (en) | Process to prepare scopine esters | |
| EP2552911B1 (en) | Tiotropium bromide preparation process | |
| TW200836732A (en) | Novel compounds | |
| CN104098560A (zh) | 噻托溴铵的结晶形式 | |
| US9636338B2 (en) | Phenyl-dihydropyridine derivatives as inhibitors of aldosterone synthase | |
| EP1831210A1 (en) | 8-aza-bicyclo[3.2.1]octane derivatives with an activity on chemokine ccr5 receptors | |
| CN101883767A (zh) | Abcg2抑制剂 | |
| US20070232659A1 (en) | Novel Alkyl Substituted Piperidine Derivatives as Monoamine Neurotransmitter Re-Uptake Inhibitors | |
| US20100286195A1 (en) | Novel benzooxazol-and benzooxathiol-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors | |
| HK1174914A1 (zh) | Cgrp受體拮抗劑 | |
| UA99521C2 (ru) | Хинуклидин-производные как антагонисты мускариновых рецепторов м3 | |
| HK1175776B (en) | 8-azabicyclo[3.2.1]octane-8-carboxamide derivative |