ATE301646T1 - Verfahren zur racematspaltung von 2-amino-6- propylamino-4,5,6,7-tetrahydrobenzothiazol sowie verbindungen dafür - Google Patents
Verfahren zur racematspaltung von 2-amino-6- propylamino-4,5,6,7-tetrahydrobenzothiazol sowie verbindungen dafürInfo
- Publication number
- ATE301646T1 ATE301646T1 AT01981155T AT01981155T ATE301646T1 AT E301646 T1 ATE301646 T1 AT E301646T1 AT 01981155 T AT01981155 T AT 01981155T AT 01981155 T AT01981155 T AT 01981155T AT E301646 T1 ATE301646 T1 AT E301646T1
- Authority
- AT
- Austria
- Prior art keywords
- compounds
- racemat
- tetrahydrobenzothiazole
- propylamino
- cleavage
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 title abstract 3
- FASDKYOPVNHBLU-UHFFFAOYSA-N N6-Propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine Chemical compound C1C(NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-UHFFFAOYSA-N 0.000 title 1
- 238000003776 cleavage reaction Methods 0.000 title 1
- 230000007017 scission Effects 0.000 title 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 abstract 1
- 229960003089 pramipexole Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200002262A ES2187249B1 (es) | 2000-09-18 | 2000-09-18 | Procedimiento para la preparacion de 2-amino-6-(alquil)amino-4,5,6,7-tetrahidrobenzotiazoles. |
| PCT/NL2001/000691 WO2002022591A1 (en) | 2000-09-18 | 2001-09-18 | Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole and compounds therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE301646T1 true ATE301646T1 (de) | 2005-08-15 |
Family
ID=8494959
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT01979066T ATE327985T1 (de) | 2000-09-18 | 2001-09-14 | Verfahren zur herstellung von 2-amino-6- (alkyl)amino-4,5,6,7-tetrahydrobenzothiazolen |
| AT01981155T ATE301646T1 (de) | 2000-09-18 | 2001-09-18 | Verfahren zur racematspaltung von 2-amino-6- propylamino-4,5,6,7-tetrahydrobenzothiazol sowie verbindungen dafür |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT01979066T ATE327985T1 (de) | 2000-09-18 | 2001-09-14 | Verfahren zur herstellung von 2-amino-6- (alkyl)amino-4,5,6,7-tetrahydrobenzothiazolen |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US6770761B2 (de) |
| EP (2) | EP1318986B1 (de) |
| AT (2) | ATE327985T1 (de) |
| AU (2) | AU2002211055A1 (de) |
| DE (1) | DE60120197T2 (de) |
| DK (2) | DK1318986T3 (de) |
| ES (3) | ES2187249B1 (de) |
| PT (2) | PT1318986E (de) |
| SI (1) | SI1318986T1 (de) |
| WO (2) | WO2002022590A1 (de) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2241118A (en) * | 1990-02-15 | 1991-08-21 | Ibm | Electrical apparatus with forced air cooling |
| US20060281797A1 (en) * | 2001-12-11 | 2006-12-14 | University Of Virginia Patent Foundation | Neurorestoration with R(+) Pramipexole |
| ATE480235T1 (de) * | 2001-12-11 | 2010-09-15 | Univ Virginia | Verwendung von pramipexol zur behandlung von amyotrophischer lateralsklerose |
| PA8578501A1 (es) | 2002-07-25 | 2005-02-04 | Pharmacia Corp | Forma de dosificacion una vez al dia de pramipexol |
| US20050226926A1 (en) | 2002-07-25 | 2005-10-13 | Pfizer Inc | Sustained-release tablet composition of pramipexole |
| GB0221513D0 (en) | 2002-09-17 | 2002-10-23 | Generics Uk Ltd | Novel compounds and processes |
| GB2394951A (en) * | 2002-11-04 | 2004-05-12 | Cipla Ltd | One pot synthesis of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole |
| US7365086B2 (en) * | 2003-07-25 | 2008-04-29 | Synthon Ip Inc. | Pramipexole acid addition salts |
| DE602005025988D1 (de) | 2004-03-19 | 2011-03-03 | Dipharma Francis Srl | Zwischenprodukte für die herstellung von pramipexol |
| EP1773793A2 (de) * | 2004-07-03 | 2007-04-18 | Merck Generics (UK) Limited | Verfahren zur herstellung von pramipexol durch chirale chromatographie |
| SG164375A1 (en) * | 2004-08-13 | 2010-09-29 | Boehringer Ingelheim Int | Extended release pellet formulation containing pramipexole or a pharmaceutically acceptable salt thereof, method for manufacturing the same and use thereof |
| DE602005024570D1 (de) | 2004-08-13 | 2010-12-16 | Boehringer Ingelheim Pharma | Tablettenformulierung mit verlängerter freisetzung mit pramipexol oder einem pharmazeutisch zulässigen salz davon, herstellungsverfahren und verwendung dafür |
| US20060069263A1 (en) * | 2004-09-30 | 2006-03-30 | Irina Gribun | Process for the reduction of (S)-2-amino-6-propionamido-4,5,6,7-tetrahydrobenzo-thiazole |
| US20060148866A1 (en) * | 2004-12-30 | 2006-07-06 | Chemagis Ltd. | Novel process for preparing pramipexole and its optical isomeric mixture by reduction with sodium triacetoxyborohydride |
| CN1834092B (zh) * | 2005-03-15 | 2010-04-28 | 姜能桥 | 盐酸普拉克索的制备方法 |
| US20090062549A1 (en) * | 2005-05-03 | 2009-03-05 | Seema Kanwar | Process for the preparation of pramipexole and new anhydrous forms of its dihydrochloride |
| ES2264378B1 (es) * | 2005-05-09 | 2007-11-01 | Ragactives, S.L. | Procedimiento para la resolucion de 2-amino-6propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos intermedios. |
| EP1917014B1 (de) * | 2005-08-15 | 2009-10-07 | University Of Virginia Patent Foundation | Neurorestauration mit r(+) pramipexol |
| WO2007040474A1 (en) * | 2005-09-21 | 2007-04-12 | Chemagis Ltd. | Novel polymorphs of (s)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole monotartrate and methods of producing and using the same |
| WO2007054970A2 (en) * | 2005-10-25 | 2007-05-18 | Alembic Limited | Novel polymorphic forms of (s)-(-)-2-amino-6-(n- propylamino) 4,5,6,7- tetrahydrobenzothiazole |
| PL378587A1 (pl) * | 2005-12-29 | 2007-07-09 | Instytut Farmaceutyczny | Sposób wytwarzania (S)-(-)-2-amino-6-n-propyloamino-4,5,6,7-tetrahydrobenzotiazolu i/lub jego soli |
| ITMI20060044A1 (it) * | 2006-01-13 | 2007-07-14 | Dipharma Spa | Sintesi di intermedi pr la preparazione di pramipexolo |
| WO2007090883A1 (en) * | 2006-02-10 | 2007-08-16 | Boehringer Ingelheim International Gmbh | Extended release formulation |
| US20090041844A1 (en) * | 2006-02-10 | 2009-02-12 | Boehringer Ingelheim International Gmbh | Modified Release Formulation |
| US8518926B2 (en) * | 2006-04-10 | 2013-08-27 | Knopp Neurosciences, Inc. | Compositions and methods of using (R)-pramipexole |
| US20070259930A1 (en) * | 2006-04-10 | 2007-11-08 | Knopp Neurosciences, Inc. | Compositions and methods of using r(+) pramipexole |
| CN102160865A (zh) * | 2006-05-16 | 2011-08-24 | 诺普神经科学股份有限公司 | R(+)和s(-)普拉克索的组合物以及使用该组合物的方法 |
| DE602006002385D1 (de) * | 2006-06-26 | 2008-10-02 | Helm Ag | Verfahren zur Herstellung von Pramipexole |
| WO2008001204A2 (en) * | 2006-06-29 | 2008-01-03 | Antares Pharma Ipl Ag | Transdermal compositions of pramipexole having enhanced permeation properties |
| US8524695B2 (en) * | 2006-12-14 | 2013-09-03 | Knopp Neurosciences, Inc. | Modified release formulations of (6R)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine and methods of using the same |
| JP2010521496A (ja) * | 2007-03-14 | 2010-06-24 | ノップ ニューロサイエンシーズ、インク. | キラル精製置換ベンゾチアゾールジアミンの合成 |
| WO2009087674A2 (en) * | 2007-12-18 | 2009-07-16 | Watson Pharma Private Limited | Improved process for the preparation of (s)-pregabalin |
| EP2334185A4 (de) * | 2008-08-19 | 2011-09-21 | Knopp Neurosciences Inc | Zusammensetzungen und verfahren zur verwendung von (r)-pramipexol |
| CA2765876A1 (en) * | 2009-06-19 | 2010-12-23 | Knopp Neurosciences, Inc. | Compositions and methods for treating amyotrophic lateral sclerosis |
| ITMI20101998A1 (it) * | 2010-10-27 | 2012-04-28 | Dipharma Francis Srl | Procedimento per la racemizzazione di acidi carbossilici |
| US9512096B2 (en) | 2011-12-22 | 2016-12-06 | Knopp Biosciences, LLP | Synthesis of amine substituted 4,5,6,7-tetrahydrobenzothiazole compounds |
| US9662313B2 (en) | 2013-02-28 | 2017-05-30 | Knopp Biosciences Llc | Compositions and methods for treating amyotrophic lateral sclerosis in responders |
| CN104072442B (zh) * | 2013-03-28 | 2016-09-28 | 成都弘达药业有限公司 | 一种化合物及其制备方法 |
| US9468630B2 (en) | 2013-07-12 | 2016-10-18 | Knopp Biosciences Llc | Compositions and methods for treating conditions related to increased eosinophils |
| SMT202100119T1 (it) | 2013-07-12 | 2021-05-07 | Knopp Biosciences Llc | Trattamento dei livelli elevati di eosinofili e/o basofili |
| EP3033081B1 (de) | 2013-08-13 | 2021-05-12 | Knopp Biosciences LLC | Zusammensetzungen und verfahren zur behandlung von chronischer nesselsucht |
| ES2813674T3 (es) | 2013-08-13 | 2021-03-24 | Knopp Biosciences Llc | Composiciones y métodos para el tratamiento de trastornos de células plasmáticas y trastornos prolinfocíticos de células b |
| CN108084115B (zh) * | 2017-12-28 | 2020-03-17 | 上海博志研新药物技术有限公司 | 盐酸普拉克索及其中间体的制备方法 |
| CN110669024A (zh) * | 2019-10-30 | 2020-01-10 | 福建福瑞明德药业有限公司 | 一种(s)-2,6-二氨基-4,5,6,7-四氢苯并噻唑*l-酒石酸盐的碱析方法 |
| CN116178304B (zh) * | 2023-03-10 | 2024-10-25 | 中国药科大学 | 一种盐酸普拉克索的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3572485D1 (en) * | 1984-12-22 | 1989-09-28 | Thomae Gmbh Dr K | Tetrahydro-benzothiazoles, their production and their use as intermediates or drugs |
| EP0207696A1 (de) | 1985-06-24 | 1987-01-07 | Eli Lilly And Company | Dialkylaminotetrahydrobenzothiazole und -oxazole |
| DE3620813A1 (de) * | 1986-06-21 | 1987-12-23 | Boehringer Ingelheim Kg | Neue tetrahydro-benzothiazole, ihre herstellung und verwendung |
-
2000
- 2000-09-18 ES ES200002262A patent/ES2187249B1/es not_active Expired - Fee Related
-
2001
- 2001-09-14 AU AU2002211055A patent/AU2002211055A1/en not_active Abandoned
- 2001-09-14 DE DE60120197T patent/DE60120197T2/de not_active Expired - Fee Related
- 2001-09-14 PT PT01979066T patent/PT1318986E/pt unknown
- 2001-09-14 ES ES01979066T patent/ES2260296T3/es not_active Expired - Lifetime
- 2001-09-14 SI SI200130558T patent/SI1318986T1/sl unknown
- 2001-09-14 DK DK01979066T patent/DK1318986T3/da active
- 2001-09-14 WO PCT/NL2001/000680 patent/WO2002022590A1/en not_active Ceased
- 2001-09-14 US US10/380,758 patent/US6770761B2/en not_active Expired - Fee Related
- 2001-09-14 AT AT01979066T patent/ATE327985T1/de not_active IP Right Cessation
- 2001-09-14 EP EP01979066A patent/EP1318986B1/de not_active Expired - Lifetime
- 2001-09-18 ES ES01981155T patent/ES2242778T3/es not_active Expired - Lifetime
- 2001-09-18 WO PCT/NL2001/000691 patent/WO2002022591A1/en not_active Ceased
- 2001-09-18 AT AT01981155T patent/ATE301646T1/de not_active IP Right Cessation
- 2001-09-18 EP EP01981155A patent/EP1318987B1/de not_active Expired - Lifetime
- 2001-09-18 PT PT01981155T patent/PT1318987E/pt unknown
- 2001-09-18 AU AU2002212815A patent/AU2002212815A1/en not_active Abandoned
- 2001-09-18 DK DK01981155T patent/DK1318987T3/da active
- 2001-09-18 US US09/953,870 patent/US6727367B2/en not_active Expired - Fee Related
-
2003
- 2003-10-06 US US10/678,081 patent/US20040068119A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| SI1318986T1 (sl) | 2006-10-31 |
| ES2260296T3 (es) | 2006-11-01 |
| PT1318987E (pt) | 2005-10-31 |
| US6727367B2 (en) | 2004-04-27 |
| EP1318986A1 (de) | 2003-06-18 |
| ES2242778T3 (es) | 2005-11-16 |
| US20020103240A1 (en) | 2002-08-01 |
| DK1318986T3 (da) | 2006-10-02 |
| US6770761B2 (en) | 2004-08-03 |
| DK1318987T3 (da) | 2005-12-12 |
| US20040029936A1 (en) | 2004-02-12 |
| US20040068119A1 (en) | 2004-04-08 |
| ATE327985T1 (de) | 2006-06-15 |
| EP1318987A1 (de) | 2003-06-18 |
| WO2002022591A1 (en) | 2002-03-21 |
| EP1318986B1 (de) | 2006-05-31 |
| DE60120197D1 (de) | 2006-07-06 |
| DE60120197T2 (de) | 2007-03-15 |
| EP1318987B1 (de) | 2005-08-10 |
| AU2002212815A1 (en) | 2002-03-26 |
| ES2187249B1 (es) | 2004-09-16 |
| AU2002211055A1 (en) | 2002-03-26 |
| ES2187249A1 (es) | 2003-05-16 |
| PT1318986E (pt) | 2006-10-31 |
| WO2002022590A1 (en) | 2002-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification |
Ref document number: 1318987 Country of ref document: EP |
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| REN | Ceased due to non-payment of the annual fee |