ES2187249A1 - Procedimiento para la preparacion de 2-amino-6-(alquil)amino-4,5,6,7-tetrahidrobenzotiazoles - Google Patents

Procedimiento para la preparacion de 2-amino-6-(alquil)amino-4,5,6,7-tetrahidrobenzotiazoles

Info

Publication number
ES2187249A1
ES2187249A1 ES200002262A ES200002262A ES2187249A1 ES 2187249 A1 ES2187249 A1 ES 2187249A1 ES 200002262 A ES200002262 A ES 200002262A ES 200002262 A ES200002262 A ES 200002262A ES 2187249 A1 ES2187249 A1 ES 2187249A1
Authority
ES
Spain
Prior art keywords
amino
group
tetrahydrobenzothiazoles
alkyl
preparation
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
Application number
ES200002262A
Other languages
English (en)
Other versions
ES2187249B1 (es
Inventor
Pospisilik Karel
Hoorn Jan Jan
Hendricus Antonius P Theodorus
Jacobus Maria Lemmens
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Synthon BV
Original Assignee
Synthon BV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to ES200002262A priority Critical patent/ES2187249B1/es
Application filed by Synthon BV filed Critical Synthon BV
Priority to SI200130558T priority patent/SI1318986T1/sl
Priority to ES01979066T priority patent/ES2260296T3/es
Priority to US10/380,758 priority patent/US6770761B2/en
Priority to AU2002211055A priority patent/AU2002211055A1/en
Priority to EP01979066A priority patent/EP1318986B1/en
Priority to AT01979066T priority patent/ATE327985T1/de
Priority to PT01979066T priority patent/PT1318986E/pt
Priority to DK01979066T priority patent/DK1318986T3/da
Priority to DE60120197T priority patent/DE60120197T2/de
Priority to PCT/NL2001/000680 priority patent/WO2002022590A1/en
Priority to ES01981155T priority patent/ES2242778T3/es
Priority to PCT/NL2001/000691 priority patent/WO2002022591A1/en
Priority to US09/953,870 priority patent/US6727367B2/en
Priority to DK01981155T priority patent/DK1318987T3/da
Priority to EP01981155A priority patent/EP1318987B1/en
Priority to AU2002212815A priority patent/AU2002212815A1/en
Priority to AT01981155T priority patent/ATE301646T1/de
Priority to PT01981155T priority patent/PT1318987E/pt
Publication of ES2187249A1 publication Critical patent/ES2187249A1/es
Priority to US10/678,081 priority patent/US20040068119A1/en
Publication of ES2187249B1 publication Critical patent/ES2187249B1/es
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Steroid Compounds (AREA)
  • Indole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Se describe un nuevo procedimiento para la obtención de pramipexol y otros productos relacionados con el mismo. El procedimiento implica la reacción de nuevos compuestos de fórmula (6) **FIGURA** en la que R es hidrógeno o un grupo acilo, R{sub,3} y R{sub,4} tienen el mismo significado y representan, cada uno de ellos, un grupo alcoxi de 1 a 4 carbonos o juntos forman un grupo C{sub,2}-C{sub,5} alquilendioxi o un grupo oxo, con una alquilamina en presencia de un agente reductor o gas hidrógeno con un catalizador de hidrogenación. Se describe también un procedimiento para obtener los nuevos compuestos asignables a la fórmula (6).
ES200002262A 2000-09-18 2000-09-18 Procedimiento para la preparacion de 2-amino-6-(alquil)amino-4,5,6,7-tetrahidrobenzotiazoles. Expired - Fee Related ES2187249B1 (es)

Priority Applications (20)

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.
ES01979066T ES2260296T3 (es) 2000-09-18 2001-09-14 Procedimiento para la preparacion de 2-amino-6(alquil)amino-4,5,6,7- tetrahidrobenzotiazoles.
US10/380,758 US6770761B2 (en) 2000-09-18 2001-09-14 Process for preparation of 2-amino-6 (alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles
AU2002211055A AU2002211055A1 (en) 2000-09-18 2001-09-14 Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles
EP01979066A EP1318986B1 (en) 2000-09-18 2001-09-14 Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles
AT01979066T ATE327985T1 (de) 2000-09-18 2001-09-14 Verfahren zur herstellung von 2-amino-6- (alkyl)amino-4,5,6,7-tetrahydrobenzothiazolen
PT01979066T PT1318986E (pt) 2000-09-18 2001-09-14 Processo para preparacao de 2-amino -6-(alquil) amino-4,5,6,7 tetra-hidrobenzotiazoles
DK01979066T DK1318986T3 (da) 2000-09-18 2001-09-14 Fremgangsmåde til fremstilling af 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazoler
DE60120197T DE60120197T2 (de) 2000-09-18 2001-09-14 Verfahren zur herstellung von 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazolen
PCT/NL2001/000680 WO2002022590A1 (en) 2000-09-18 2001-09-14 Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles
SI200130558T SI1318986T1 (sl) 2000-09-18 2001-09-14 Postopek za pripravo 2-amino-6-(alkil)amino-4,5,6,7 -tetrahidrobenzotiazolov
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
EP01981155A EP1318987B1 (en) 2000-09-18 2001-09-18 Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole and compounds therefor
DK01981155T DK1318987T3 (da) 2000-09-18 2001-09-18 Fremgangsmåde til resolution af 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazol og forbindelser til brug hertil
US09/953,870 US6727367B2 (en) 2000-09-18 2001-09-18 Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzthiazole and compounds therefor
AU2002212815A AU2002212815A1 (en) 2000-09-18 2001-09-18 Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole and compounds therefor
ES01981155T ES2242778T3 (es) 2000-09-18 2001-09-18 Procedimiento para la resolucion de 2-amino-6-propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos utiles para ello.
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
PT01981155T PT1318987E (pt) 2000-09-18 2001-09-18 Processo de resolucao do 2-amino-6-propilamino-4,5,6,7-tetra-hidrobenzotiazole e compostos para esse fim
US10/678,081 US20040068119A1 (en) 2000-09-18 2003-10-06 Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzthiazole and compounds therefor

Applications Claiming Priority (1)

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.

Publications (2)

Publication Number Publication Date
ES2187249A1 true ES2187249A1 (es) 2003-05-16
ES2187249B1 ES2187249B1 (es) 2004-09-16

Family

ID=8494959

Family Applications (3)

Application Number Title Priority Date Filing Date
ES200002262A Expired - Fee Related ES2187249B1 (es) 2000-09-18 2000-09-18 Procedimiento para la preparacion de 2-amino-6-(alquil)amino-4,5,6,7-tetrahidrobenzotiazoles.
ES01979066T Expired - Lifetime ES2260296T3 (es) 2000-09-18 2001-09-14 Procedimiento para la preparacion de 2-amino-6(alquil)amino-4,5,6,7- tetrahidrobenzotiazoles.
ES01981155T Expired - Lifetime ES2242778T3 (es) 2000-09-18 2001-09-18 Procedimiento para la resolucion de 2-amino-6-propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos utiles para ello.

Family Applications After (2)

Application Number Title Priority Date Filing Date
ES01979066T Expired - Lifetime ES2260296T3 (es) 2000-09-18 2001-09-14 Procedimiento para la preparacion de 2-amino-6(alquil)amino-4,5,6,7- tetrahidrobenzotiazoles.
ES01981155T Expired - Lifetime ES2242778T3 (es) 2000-09-18 2001-09-18 Procedimiento para la resolucion de 2-amino-6-propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos utiles para ello.

Country Status (10)

Country Link
US (3) US6770761B2 (es)
EP (2) EP1318986B1 (es)
AT (2) ATE327985T1 (es)
AU (2) AU2002211055A1 (es)
DE (1) DE60120197T2 (es)
DK (2) DK1318986T3 (es)
ES (3) ES2187249B1 (es)
PT (2) PT1318986E (es)
SI (1) SI1318986T1 (es)
WO (2) WO2002022590A1 (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006120268A1 (es) 2005-05-09 2006-11-16 Ragactives, S.L. Procedimiento para la resolución de 2-amino-6-propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos intermedios

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GB2241118A (en) * 1990-02-15 1991-08-21 Ibm Electrical apparatus with forced air cooling
ES2432527T3 (es) * 2001-12-11 2013-12-04 University Of Virginia Patent Foundation Uso de pramipexol para tratar la esclerosis lateral amiotrófica
US20060281797A1 (en) * 2001-12-11 2006-12-14 University Of Virginia Patent Foundation Neurorestoration with R(+) Pramipexole
US20050226926A1 (en) 2002-07-25 2005-10-13 Pfizer Inc Sustained-release tablet composition of pramipexole
US8679533B2 (en) 2002-07-25 2014-03-25 Pharmacia Corporation Pramipexole once-daily dosage form
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
JP2007529446A (ja) 2004-03-19 2007-10-25 ディファルマ・ソシエタ・ペル・アチオニ プラミペキソールの製造のための中間体
US20080096939A1 (en) * 2004-07-03 2008-04-24 Andreas Keil Process For Preparation Of Pramipexole By Chiral Chromatography
WO2006015943A2 (en) * 2004-08-13 2006-02-16 Boehringer Ingelheim International Gmbh Extended release pellet formulation containing pramipexole or a pharmaceutically acceptable salt thereof, method for manufacturing the same and use thereof
EP2345407A1 (en) * 2004-08-13 2011-07-20 Boehringer Ingelheim International GmbH Extended release tablet formulation containing pramipexole or a pharmaceutically acceptable salt thereof, method for manufacturing the same and use thereof
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
ATE444750T1 (de) * 2005-08-15 2009-10-15 Univ Virginia 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
US20090098202A1 (en) * 2006-02-10 2009-04-16 Boehringer Ingelheim International Gmbh Extended Release Formulation
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US8518926B2 (en) 2006-04-10 2013-08-27 Knopp Neurosciences, Inc. Compositions and methods of using (R)-pramipexole
US8017598B2 (en) 2006-05-16 2011-09-13 Knopp Neurosciences, Inc. Compositions of R(+) and S(−) pramipexole and methods of using the same
US20070259930A1 (en) * 2006-04-10 2007-11-08 Knopp Neurosciences, Inc. Compositions and methods of using r(+) pramipexole
ATE405554T1 (de) * 2006-06-26 2008-09-15 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
RU2454409C2 (ru) 2007-03-14 2012-06-27 Нопп Ньюросайенсиз, Инк. Синтез хирально очищенных замещенных бензотиазолдиаминов
EP2225199A2 (en) * 2007-12-18 2010-09-08 Watson Pharma Private Limited Improved process for the preparation of (s)-pregabalin
CN102186350A (zh) 2008-08-19 2011-09-14 诺普神经科学股份有限公司 使用(r)-普拉克索的组合物与方法
US20110009460A1 (en) * 2009-06-19 2011-01-13 Valentin Gribkoff 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
LT3019167T (lt) 2013-07-12 2021-03-25 Knopp Biosciences Llc Eozinofilų ir (arba) bazofilų padidintų kiekių gydymas
US9642840B2 (en) 2013-08-13 2017-05-09 Knopp Biosciences, Llc Compositions and methods for treating plasma cell disorders and B-cell prolymphocytic disorders
DK3033081T3 (da) 2013-08-13 2021-05-31 Knopp Biosciences Llc Sammensætninger og fremgangsmåder til behandling af kronisk urticaria
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
CN116178304A (zh) * 2023-03-10 2023-05-30 中国药科大学 一种盐酸普拉克索的合成方法

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2006120268A1 (es) 2005-05-09 2006-11-16 Ragactives, S.L. Procedimiento para la resolución de 2-amino-6-propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos intermedios

Also Published As

Publication number Publication date
DE60120197D1 (de) 2006-07-06
WO2002022591A1 (en) 2002-03-21
AU2002212815A1 (en) 2002-03-26
EP1318987A1 (en) 2003-06-18
US6770761B2 (en) 2004-08-03
SI1318986T1 (sl) 2006-10-31
EP1318986A1 (en) 2003-06-18
ES2260296T3 (es) 2006-11-01
US20020103240A1 (en) 2002-08-01
US20040029936A1 (en) 2004-02-12
US6727367B2 (en) 2004-04-27
EP1318986B1 (en) 2006-05-31
DE60120197T2 (de) 2007-03-15
DK1318987T3 (da) 2005-12-12
EP1318987B1 (en) 2005-08-10
ES2242778T3 (es) 2005-11-16
US20040068119A1 (en) 2004-04-08
ES2187249B1 (es) 2004-09-16
PT1318987E (pt) 2005-10-31
DK1318986T3 (da) 2006-10-02
AU2002211055A1 (en) 2002-03-26
ATE327985T1 (de) 2006-06-15
PT1318986E (pt) 2006-10-31
WO2002022590A1 (en) 2002-03-21
ATE301646T1 (de) 2005-08-15

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