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)
  • 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

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)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
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 (en) * 2001-12-11 2010-09-15 Univ Virginia USE OF PRAMIPEXOLE TO TREAT AMYOTROPHIC LATERAL SCLERosis
US20050226926A1 (en) 2002-07-25 2005-10-13 Pfizer Inc Sustained-release tablet composition of pramipexole
AR040682A1 (en) 2002-07-25 2005-04-13 Pharmacia Corp DOSAGE FORM ONCE A DAY OF 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 (en) * 2004-08-13 2010-10-06 贝林格尔·英格海姆国际有限公司 The prolongation release tablet that comprises pramipexole or its officinal salt
JP4971159B2 (en) 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 Sustained release pellet preparation containing pramipexole or a pharmaceutically acceptable salt thereof, its production method and use
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
WO2006117614A1 (en) * 2005-05-03 2006-11-09 Ranbaxy Laboratories Limited 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.
JP2009504748A (en) * 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 Nerve recovery with R (+) pramipexole
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 (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
CA2641665A1 (en) * 2006-02-10 2007-08-16 Boehringer Ingelheim International Gmbh Modified release formulation
WO2007090883A1 (en) * 2006-02-10 2007-08-16 Boehringer Ingelheim International Gmbh Extended 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
KR20090021169A (en) 2006-05-16 2009-02-27 크놉 뉴로사이언시스 인코포레이티드 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
WO2008113056A2 (en) * 2007-03-14 2008-09-18 Knopp Neurosciences, Inc. Synthesis of chirally purified substituted benzothiazole diamines
US20100312010A1 (en) * 2007-12-18 2010-12-09 Watson Pharma Private Limited Process for the Preparation of (S)-Pregabalin
EP2334185A4 (en) * 2008-08-19 2011-09-21 Knopp Neurosciences Inc Compositions and methods of using (r)-pramipexole
MX2011013577A (en) * 2009-06-19 2012-04-10 Knopp Neurosciences Inc 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
PL3019167T3 (en) 2013-07-12 2021-06-14 Knopp Biosciences Llc Treating elevated levels of eosinophils and/or basophils
US9468630B2 (en) 2013-07-12 2016-10-18 Knopp Biosciences Llc Compositions and methods for treating conditions related to increased eosinophils
ES2813674T3 (en) 2013-08-13 2021-03-24 Knopp Biosciences Llc Compositions and methods for treating plasma cell disorders and b-cell prolymphocytic disorders
HUE055850T2 (en) 2013-08-13 2022-01-28 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
CN116178304A (en) * 2023-03-10 2023-05-30 中国药科大学 Synthesis method of pramipexole dihydrochloride

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0186087B1 (en) * 1984-12-22 1989-08-23 Dr. Karl Thomae GmbH Tetrahydro-benzothiazoles, their production and their use as intermediates or drugs
EP0207696A1 (en) * 1985-06-24 1987-01-07 Eli Lilly And Company 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
ES2242778T3 (en) 2005-11-16
WO2002022590A1 (en) 2002-03-21
ES2187249A1 (en) 2003-05-16
EP1318987B1 (en) 2005-08-10
US20040068119A1 (en) 2004-04-08
ATE327985T1 (en) 2006-06-15
PT1318987E (en) 2005-10-31
DK1318986T3 (en) 2006-10-02
EP1318986B1 (en) 2006-05-31
ATE301646T1 (en) 2005-08-15
ES2187249B1 (en) 2004-09-16
PT1318986E (en) 2006-10-31
DK1318987T3 (en) 2005-12-12
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 (en) 2007-03-15
DE60120197D1 (en) 2006-07-06
US20020103240A1 (en) 2002-08-01
ES2260296T3 (en) 2006-11-01
US20040029936A1 (en) 2004-02-12
SI1318986T1 (en) 2006-10-31
US6770761B2 (en) 2004-08-03

Similar Documents

Publication Publication Date Title
AU2002211055A1 (en) Process for preparation of 2-amino-6-(alkyl) amino-4,5,6,7-tetrahydrobenzothiazoles
HK1023987A1 (en) Sulphinic acid derivatives, method for producing, and their use
NZ524857A (en) Piperidine compounds as anti-allergics
BG105457A (en) Method for the preparation of citalopram
ES2005745A6 (en) Process for the preparation of aryl-piperidine carbinols.
PT804200E (en) USE OF NORIBOGAINE DERIVATIVES FOR TREATMENT OF CHEMICAL DEPENDENCY IN MAMMALS
BR0214142A (en) N-Adamantyl methyl derivatives and intermediates as pharmaceutical compositions and processes for their preparation
CA2304713A1 (en) Biphenyl-5-alkanoic acid derivatives and use thereof
HUP0104295A2 (en) Use of organic substance forming a complex with a transition metal for preparing a bleaching composition and method for bleaching a substrate
ID21547A (en) CRYSTALS OF THE BENZIMIDAZOL DERIVES AND THEIR PRODUCTS
CA2369093A1 (en) Anticonvulsant derivatives useful in lowering lipids
ES8801221A1 (en) Cyclopenta[d]pyrimidine derivatives, their preparation and use.
HK1065781A1 (en) Process and intermediates to prepare latanoprost
HUP0102657A2 (en) Method for the preparation of ortho-alkylated benzoic acid derivatives as intermediates and ingredients
TW238304B (en) A process for the preparation of 1-substituted-5(4H)-tetrazolinones
SI1102765T1 (en) PROCESS FOR THE SYNTHESIS OF (1$i(H))-BENZO C)QUINOLIZIN-3-ONES DERIVATIVES
EP0247373A3 (en) 7-(phenylacetamido)-4-alkyl coumarins, process for their preparation as well as their application in processes for the fluorometric determination of the activity of hydrolases, especially of penicilline g acylase
IL155486A0 (en) Process for producing substituted aniline compound
JO2433B1 (en) Process for the preparation of heterocyclic indene analogs
FR2498184B1 (en)
AU4900499A (en) Use of amino azoic dyes as markers of oil distillation products
CA2024114A1 (en) Phenolic compounds as chain-terminators for the anionic solution polymerisation of dienes
HUP0104064A2 (en) Method and intermediates for producing bis(oxim)monoethers
PL363756A1 (en) Process for preparing fluconazole and its crystal modifications
ES2103044T3 (en) PROCEDURE TO PREPARE 5-CHLOROXINDOL.