AU2003282038A1 - Method for the production of (r)-salbutamol - Google Patents

Method for the production of (r)-salbutamol

Info

Publication number
AU2003282038A1
AU2003282038A1 AU2003282038A AU2003282038A AU2003282038A1 AU 2003282038 A1 AU2003282038 A1 AU 2003282038A1 AU 2003282038 A AU2003282038 A AU 2003282038A AU 2003282038 A AU2003282038 A AU 2003282038A AU 2003282038 A1 AU2003282038 A1 AU 2003282038A1
Authority
AU
Australia
Prior art keywords
hydrogenation
salbutamol
acid
treatment
optionally
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
AU2003282038A
Inventor
Franz Dietrich Klingler
Paul Kreye
Alfons Lenhart
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
BOEHRINGER INGELHEIM PHARMA
Boehringer Ingelheim Pharma GmbH and Co KG
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 BOEHRINGER INGELHEIM PHARMA, Boehringer Ingelheim Pharma GmbH and Co KG filed Critical BOEHRINGER INGELHEIM PHARMA
Publication of AU2003282038A1 publication Critical patent/AU2003282038A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Saccharide Compounds (AREA)

Abstract

Method for producing levo-salbutamol (I; alpha-(((1,1-dimethylethyl)amino)methyl)-4-hydroxy-1,3-benzenedimethanol) or its salts by asymmetric hydrogenation of prochiral salbutamone (II) in presence of rhodium and a chiral, bidentate phosphine ligand (III), optionally followed by treatment with acid to form a salt. An Independent claim is also included for preparation of (I) by: (1) bromination of 4-acetoxy-3-acetoxymethylacetophenone; (2) reaction of the product with N-tert-butyl-N-benzylamine; (3) hydrogenation of palladium catalyst (debenzylation); (4) hydrogenation of the resulting (II) by the new method and (5) optionally treatment with acid.
AU2003282038A 2002-10-24 2003-10-18 Method for the production of (r)-salbutamol Abandoned AU2003282038A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10249576A DE10249576B3 (en) 2002-10-24 2002-10-24 Preparation of levo-salbutamol, useful as bronchodilator, by asymmetrical catalytic hydrogenation of its ketone precursor in presence of rhodium and chiral phosphine
DE10249576.9 2002-10-24
PCT/EP2003/011583 WO2004037767A1 (en) 2002-10-24 2003-10-18 Method for the production of (r)-salbutamol

Publications (1)

Publication Number Publication Date
AU2003282038A1 true AU2003282038A1 (en) 2004-05-13

Family

ID=31984428

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2003282038A Abandoned AU2003282038A1 (en) 2002-10-24 2003-10-18 Method for the production of (r)-salbutamol

Country Status (10)

Country Link
EP (1) EP1585718B1 (en)
JP (1) JP2006503884A (en)
CN (1) CN1289465C (en)
AT (1) ATE367372T1 (en)
AU (1) AU2003282038A1 (en)
CA (1) CA2503439A1 (en)
DE (2) DE10249576B3 (en)
ES (1) ES2290509T3 (en)
HK (1) HK1084938A1 (en)
WO (1) WO2004037767A1 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004033313A1 (en) 2004-07-08 2006-01-26 Boehringer Ingelheim Pharma Gmbh & Co. Kg Process for the preparation of enantiomers 3-hydroxy-3-phenyl-propylamines
WO2007145203A1 (en) * 2006-06-13 2007-12-21 Daiichi Fine Chemical Co., Ltd. Optically active 2-amino-1-(4-fluorophenyl)ethanol
CN103553941B (en) * 2013-10-30 2015-02-18 新乡学院 Method for preparing levalbuterol
CN108623486A (en) * 2018-07-13 2018-10-09 重庆康刻尔制药有限公司 A kind of preparation method of V hydrochloride of salbutamol intermediate
CN110963929B (en) * 2019-11-26 2022-10-21 安徽恒星制药有限公司 Preparation method of salbutamol hydrochloride suitable for industrial production
CN112062684B (en) * 2020-09-15 2021-06-15 重庆康刻尔制药股份有限公司 Method for purifying salbutamol intermediate IV
CN112500291B (en) * 2020-12-14 2022-11-04 上海医药集团(本溪)北方药业有限公司 Preparation and purification method of beta 2 receptor agonist intermediate
CN115286521B (en) * 2022-07-11 2023-11-03 上海医药集团(本溪)北方药业有限公司 Synthesis method of levosalbutamol hydrochloride
CN115073313B (en) * 2022-08-24 2022-11-25 山东省食品药品检验研究院 Method for synthesizing terbutaline sulfate impurity C

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1200886A (en) * 1966-09-23 1970-08-05 Allen & Hanburys Ltd Phenylaminoethanol derivatives
ZW6584A1 (en) * 1983-04-18 1985-04-17 Glaxo Group Ltd Phenethanolamine derivatives
US5442118A (en) * 1994-04-22 1995-08-15 Sepracor, Inc. Asymmetric synthesis of (R)- and (S)-arylethanolamines from iminoketones
DE19902229C2 (en) * 1999-01-21 2000-11-02 Boehringer Ingelheim Pharma Process for the preparation of L-phenylephrine hydrochloride

Also Published As

Publication number Publication date
WO2004037767A1 (en) 2004-05-06
ES2290509T3 (en) 2008-02-16
HK1084938A1 (en) 2006-08-11
DE10249576B3 (en) 2004-04-08
CA2503439A1 (en) 2004-05-06
CN1705634A (en) 2005-12-07
JP2006503884A (en) 2006-02-02
CN1289465C (en) 2006-12-13
EP1585718B1 (en) 2007-07-18
ATE367372T1 (en) 2007-08-15
EP1585718A1 (en) 2005-10-19
DE50307735D1 (en) 2007-08-30

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Legal Events

Date Code Title Description
MK6 Application lapsed section 142(2)(f)/reg. 8.3(3) - pct applic. not entering national phase