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AU2002211055A1 - Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles - Google Patents

Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles

Info

Publication number
AU2002211055A1
AU2002211055A1 AU2002211055A AU1105502A AU2002211055A1 AU 2002211055 A1 AU2002211055 A1 AU 2002211055A1 AU 2002211055 A AU2002211055 A AU 2002211055A AU 1105502 A AU1105502 A AU 1105502A AU 2002211055 A1 AU2002211055 A1 AU 2002211055A1
Authority
AU
Australia
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.)
Abandoned
Application number
AU2002211055A
Inventor
Hans Jan Hoorn
Jacobus Maria Lemmens
Theodorus Hendricus Antonius Peters
Karel Pospisilik
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
Application filed by Synthon BV filed Critical Synthon BV
Publication of AU2002211055A1 publication Critical patent/AU2002211055A1/en
Abandoned 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)
  • Indole Compounds (AREA)
  • Steroid Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A new process to obtain pramipexole and related products is described. The process involves the reaction of new compounds of formula (6), wherein R is hydrogen or acyl group, R3 and R4 are either the same and each of them represents an alkoxy group of 1-4 carbons or they together form a C2-C5 alkylenedioxy group or an oxo-group, with an alkylamine in the presence of a reducing agent or a hydrogen gas with hydrogenation catalyst. A process to obtain new compounds of formula (6) is also described.
AU2002211055A 2000-09-18 2001-09-14 Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles Abandoned AU2002211055A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ES200002262A ES2187249B1 (en) 2000-09-18 2000-09-18 PROCEDURE FOR THE PREPARATION OF 2-AMINO-6- (RENT) AMINO-4,5,6,7-TETRAHYDROBENZOTIAZOLES.
ES200002262 2000-09-18
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

Publications (1)

Publication Number Publication Date
AU2002211055A1 true AU2002211055A1 (en) 2002-03-26

Family

ID=8494959

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2002211055A Abandoned AU2002211055A1 (en) 2000-09-18 2001-09-14 Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles
AU2002212815A Abandoned AU2002212815A1 (en) 2000-09-18 2001-09-18 Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole and compounds therefor

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU2002212815A Abandoned AU2002212815A1 (en) 2000-09-18 2001-09-18 Process for resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole and compounds therefor

Country Status (10)

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

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GB2241118A (en) * 1990-02-15 1991-08-21 Ibm Electrical apparatus with forced air cooling
ATE480235T1 (en) * 2001-12-11 2010-09-15 Univ Virginia USE OF PRAMIPEXOLE TO TREAT AMYOTROPHIC LATERAL SCLERosis
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
DE602005025988D1 (en) 2004-03-19 2011-03-03 Dipharma Francis Srl INTERMEDIATE PRODUCTS FOR THE PREPARATION OF PRAMIPEXOL
WO2006003471A2 (en) * 2004-07-03 2006-01-12 Generics [Uk] Limited Process for the preparation of pramipexole by chiral chromatography
ATE486588T1 (en) * 2004-08-13 2010-11-15 Boehringer Ingelheim Int EXTENDED RELEASE TABLET FORMULATION CONTAINING PRAMIPEXOLE OR A PHARMACEUTICALLY APPROVED SALT THEREOF, METHOD OF PREPARATION AND USE THEREOF
EP2431027A1 (en) * 2004-08-13 2012-03-21 Boehringer Ingelheim International GmbH Extended release pellet 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
DE112005003227T5 (en) * 2004-12-30 2007-11-15 Chemagis Ltd. A new process for the preparation of pramipexole and the mixture of its optical isomers by reduction with sodium triacetoxyborohydride
CN1834092B (en) * 2005-03-15 2010-04-28 姜能桥 Preparation of pramipexole
US20090062549A1 (en) * 2005-05-03 2009-03-05 Seema Kanwar Process for the preparation of pramipexole and new anhydrous forms of its dihydrochloride
ES2264378B1 (en) * 2005-05-09 2007-11-01 Ragactives, S.L. PROCEDURE FOR THE RESOLUTION OF 2-AMINO-6PROPILAMINO-4,5,6,7-TETRAHYDROBENZOTIAZOL AND INTERMEDIATE COMPOUNDS.
WO2007022182A1 (en) * 2005-08-15 2007-02-22 University Of Virginia Patent Foundation Neurorestoration with r(+) pramipexole
EP1926486A4 (en) * 2005-09-21 2009-06-10 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 (en) * 2005-12-29 2007-07-09 Instytut Farmaceutyczny Methods of (S)-(-)-2-amino-6-n-propyloamino-4,5,6,7-tetrahydrobenzotiazole and/or its salts
ITMI20060044A1 (en) * 2006-01-13 2007-07-14 Dipharma Spa SUMMARY OF INTERMEDIATES PR PREPARATION OF PRAMIPEXOL
US20090098202A1 (en) * 2006-02-10 2009-04-16 Boehringer Ingelheim International Gmbh Extended Release Formulation
JP2009526021A (en) * 2006-02-10 2009-07-16 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 Formulation with controlled release
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
EP2026803B1 (en) * 2006-05-16 2011-12-21 Knopp Neurosciences, Inc. Compositions of r(+) and s(-) pramipexole and methods of using the same
ATE405554T1 (en) * 2006-06-26 2008-09-15 Helm Ag METHOD FOR PRODUCING 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
EP2137171A4 (en) * 2007-03-14 2010-05-19 Knopp Neurosciences Inc Synthesis of chirally purified substituted benzothiazole diamines
EP2225199A2 (en) * 2007-12-18 2010-09-08 Watson Pharma Private Limited Improved process for the preparation of (s)-pregabalin
WO2010022140A1 (en) 2008-08-19 2010-02-25 Knopp Neurosciences, Inc. Compositions and methods of using (r)-pramipexole
CN102802418A (en) * 2009-06-19 2012-11-28 诺普神经科学股份有限公司 Compositions and methods for treating amyotrophic lateral sclerosis
ITMI20101998A1 (en) * 2010-10-27 2012-04-28 Dipharma Francis Srl PROCEDURE FOR THE RACEMIZATION OF CARBOXYLIC ACIDS
WO2013096816A1 (en) 2011-12-22 2013-06-27 Biogen Idec Ma Inc. Improved 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 (en) * 2013-03-28 2016-09-28 成都弘达药业有限公司 A kind of compound and preparation method thereof
US9468630B2 (en) 2013-07-12 2016-10-18 Knopp Biosciences Llc Compositions and methods for treating conditions related to increased eosinophils
EP3019167B1 (en) 2013-07-12 2021-02-17 Knopp Biosciences LLC Treating elevated levels of eosinophils and/or basophils
EP3038467B1 (en) 2013-08-13 2020-07-29 Knopp Biosciences LLC Compositions and methods for treating plasma cell disorders and b-cell prolymphocytic disorders
PL3033081T3 (en) 2013-08-13 2021-08-30 Knopp Biosciences Llc Compositions and methods for treating chronic urticaria
CN108084115B (en) * 2017-12-28 2020-03-17 上海博志研新药物技术有限公司 Preparation method of pramipexole dihydrochloride and intermediate thereof
CN110669024A (en) * 2019-10-30 2020-01-10 福建福瑞明德药业有限公司 Alkali precipitation method of (S) -2, 6-diamino-4, 5,6, 7-tetrahydrobenzothiazole L-tartrate
CN116178304B (en) * 2023-03-10 2024-10-25 中国药科大学 Synthesis method of pramipexole dihydrochloride

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EP0186087B1 (en) * 1984-12-22 1989-08-23 Dr. Karl Thomae GmbH Tetrahydro-benzothiazoles, their production and their use as intermediates or drugs
ZA864626B (en) * 1985-06-24 1988-02-24 Lilly Co Eli Dialkylaminotetrahydrobenzothiazoles and oxazoles
DE3620813A1 (en) * 1986-06-21 1987-12-23 Boehringer Ingelheim Kg NEW TETRAHYDRO-BENZOTHIAZOLES, THEIR PRODUCTION AND USE

Also Published As

Publication number Publication date
EP1318986B1 (en) 2006-05-31
ATE327985T1 (en) 2006-06-15
US20040068119A1 (en) 2004-04-08
SI1318986T1 (en) 2006-10-31
WO2002022591A1 (en) 2002-03-21
DK1318986T3 (en) 2006-10-02
PT1318986E (en) 2006-10-31
ES2187249B1 (en) 2004-09-16
DK1318987T3 (en) 2005-12-12
ES2187249A1 (en) 2003-05-16
AU2002212815A1 (en) 2002-03-26
US20020103240A1 (en) 2002-08-01
DE60120197D1 (en) 2006-07-06
PT1318987E (en) 2005-10-31
US6727367B2 (en) 2004-04-27
EP1318987B1 (en) 2005-08-10
WO2002022590A1 (en) 2002-03-21
EP1318987A1 (en) 2003-06-18
ES2260296T3 (en) 2006-11-01
ES2242778T3 (en) 2005-11-16
ATE301646T1 (en) 2005-08-15
US6770761B2 (en) 2004-08-03
EP1318986A1 (en) 2003-06-18
US20040029936A1 (en) 2004-02-12
DE60120197T2 (en) 2007-03-15

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