AU2003282038A1 - Method for the production of (r)-salbutamol - Google Patents
Method for the production of (r)-salbutamolInfo
- 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
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.
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)
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)
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 |
-
2002
- 2002-10-24 DE DE10249576A patent/DE10249576B3/en not_active Expired - Fee Related
-
2003
- 2003-10-18 CN CN200380101904.3A patent/CN1289465C/en not_active Expired - Fee Related
- 2003-10-18 DE DE50307735T patent/DE50307735D1/en not_active Expired - Lifetime
- 2003-10-18 CA CA002503439A patent/CA2503439A1/en not_active Abandoned
- 2003-10-18 EP EP03773653A patent/EP1585718B1/en not_active Expired - Lifetime
- 2003-10-18 JP JP2004545893A patent/JP2006503884A/en active Pending
- 2003-10-18 ES ES03773653T patent/ES2290509T3/en not_active Expired - Lifetime
- 2003-10-18 AU AU2003282038A patent/AU2003282038A1/en not_active Abandoned
- 2003-10-18 AT AT03773653T patent/ATE367372T1/en not_active IP Right Cessation
- 2003-10-18 WO PCT/EP2003/011583 patent/WO2004037767A1/en active IP Right Grant
-
2006
- 2006-04-28 HK HK06105082A patent/HK1084938A1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
WO2004037767A1 (en) | 2004-05-06 |
EP1585718B1 (en) | 2007-07-18 |
DE50307735D1 (en) | 2007-08-30 |
ES2290509T3 (en) | 2008-02-16 |
CN1289465C (en) | 2006-12-13 |
JP2006503884A (en) | 2006-02-02 |
CN1705634A (en) | 2005-12-07 |
CA2503439A1 (en) | 2004-05-06 |
HK1084938A1 (en) | 2006-08-11 |
DE10249576B3 (en) | 2004-04-08 |
ATE367372T1 (en) | 2007-08-15 |
EP1585718A1 (en) | 2005-10-19 |
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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 |