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 EP01979066A priority patent/EP1318986B1/en
Priority to DE60120197T priority patent/DE60120197T2/de
Priority to AU2002211055A priority patent/AU2002211055A1/en
Priority to SI200130558T priority patent/SI1318986T1/sl
Priority to AT01979066T priority patent/ATE327985T1/de
Priority to ES01979066T priority patent/ES2260296T3/es
Priority to DK01979066T priority patent/DK1318986T3/da
Priority to PT01979066T priority patent/PT1318986E/pt
Priority to US10/380,758 priority patent/US6770761B2/en
Priority to PCT/NL2001/000680 priority patent/WO2002022590A1/en
Priority to PT01981155T priority patent/PT1318987E/pt
Priority to AT01981155T priority patent/ATE301646T1/de
Priority to EP01981155A priority patent/EP1318987B1/en
Priority to US09/953,870 priority patent/US6727367B2/en
Priority to ES01981155T priority patent/ES2242778T3/es
Priority to AU2002212815A priority patent/AU2002212815A1/en
Priority to DK01981155T priority patent/DK1318987T3/da
Priority to PCT/NL2001/000691 priority patent/WO2002022591A1/en
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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Indole Compounds (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.
DE60120197T DE60120197T2 (de) 2000-09-18 2001-09-14 Verfahren zur herstellung von 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazolen
AU2002211055A AU2002211055A1 (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
AT01979066T ATE327985T1 (de) 2000-09-18 2001-09-14 Verfahren zur herstellung von 2-amino-6- (alkyl)amino-4,5,6,7-tetrahydrobenzothiazolen
ES01979066T ES2260296T3 (es) 2000-09-18 2001-09-14 Procedimiento para la preparacion de 2-amino-6(alquil)amino-4,5,6,7- tetrahidrobenzotiazoles.
DK01979066T DK1318986T3 (da) 2000-09-18 2001-09-14 Fremgangsmåde til fremstilling af 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazoler
PT01979066T PT1318986E (pt) 2000-09-18 2001-09-14 Processo para preparacao de 2-amino -6-(alquil) amino-4,5,6,7 tetra-hidrobenzotiazoles
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
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
EP01979066A EP1318986B1 (en) 2000-09-18 2001-09-14 Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles
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
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.
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
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
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
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
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
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
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
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
US20050226926A1 (en) 2002-07-25 2005-10-13 Pfizer Inc Sustained-release tablet composition of pramipexole
AR040682A1 (es) 2002-07-25 2005-04-13 Pharmacia Corp Forma de dosificacion una vez al dia de pramipexol
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
EP2289885A1 (en) 2004-03-19 2011-03-02 Dipharma Francis S.r.l. Intermediates for the preparation of pramipexole
EP1773793A2 (en) * 2004-07-03 2007-04-18 Merck Generics (UK) Limited Process for the preparation of pramipexole by chiral chromatography
CN101849921A (zh) * 2004-08-13 2010-10-06 贝林格尔·英格海姆国际有限公司 包含普拉克索或其可药用盐的延长释放片剂
JP4971159B2 (ja) 2004-08-13 2012-07-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング プラミペキソール又はその薬学的に許容しうる塩を含有する徐放性ペレット製剤、その製法及び使用
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
DE112005003227T5 (de) * 2004-12-30 2007-11-15 Chemagis Ltd. Neues Verfahren zur Herstellung von Pramipexol und dem Gemisch seiner optischen Isomeren durch Reduktion mit Natriumtriacetoxyborhydrid
CN1834092B (zh) * 2005-03-15 2010-04-28 姜能桥 盐酸普拉克索的制备方法
WO2006117614A1 (en) * 2005-05-03 2006-11-09 Ranbaxy Laboratories Limited Process for the preparation of pramipexole and new anhydrous forms of its dihydrochloride
JP2009504748A (ja) * 2005-08-15 2009-02-05 ユニバーシティ オブ バージニア パテント ファウンデーション Ｒ（＋）プラミペキソールを用いた神経回復
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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
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US8518926B2 (en) * 2006-04-10 2013-08-27 Knopp Neurosciences, Inc. Compositions and methods of using (R)-pramipexole
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KR20090021169A (ko) 2006-05-16 2009-02-27 크놉 뉴로사이언시스 인코포레이티드 Ｒ(+) 및 ｓ(-) 프라미펙솔을 포함하는 조성물 및 이의 사용 방법
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
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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
PL3019167T3 (pl) 2013-07-12 2021-06-14 Knopp Biosciences Llc Leczenie podwyższonych poziomów eozynofili i/lub bazofili
US9468630B2 (en) 2013-07-12 2016-10-18 Knopp Biosciences Llc Compositions and methods for treating conditions related to increased eosinophils
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
HUE055850T2 (hu) 2013-08-13 2022-01-28 Knopp Biosciences Llc Készítmények és módszerek a krónikus urticaria (csalánkiütés) kezelésére
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
ES2242778T3 (es) 2005-11-16
WO2002022590A1 (en) 2002-03-21
EP1318987B1 (en) 2005-08-10
US20040068119A1 (en) 2004-04-08
ATE327985T1 (de) 2006-06-15
PT1318987E (pt) 2005-10-31
DK1318986T3 (da) 2006-10-02
EP1318986B1 (en) 2006-05-31
ATE301646T1 (de) 2005-08-15
ES2187249B1 (es) 2004-09-16
PT1318986E (pt) 2006-10-31
DK1318987T3 (da) 2005-12-12
AU2002211055A1 (en) 2002-03-26
US6727367B2 (en) 2004-04-27
EP1318987A1 (en) 2003-06-18
EP1318986A1 (en) 2003-06-18
WO2002022591A1 (en) 2002-03-21
AU2002212815A1 (en) 2002-03-26
DE60120197T2 (de) 2007-03-15
DE60120197D1 (de) 2006-07-06
US20020103240A1 (en) 2002-08-01
ES2260296T3 (es) 2006-11-01
US20040029936A1 (en) 2004-02-12
SI1318986T1 (sl) 2006-10-31
US6770761B2 (en) 2004-08-03

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