AU2002220918A1 - Process for preparing isomers of salbutamol - Google Patents
Process for preparing isomers of salbutamolInfo
- Publication number
- AU2002220918A1 AU2002220918A1 AU2002220918A AU2091802A AU2002220918A1 AU 2002220918 A1 AU2002220918 A1 AU 2002220918A1 AU 2002220918 A AU2002220918 A AU 2002220918A AU 2091802 A AU2091802 A AU 2091802A AU 2002220918 A1 AU2002220918 A1 AU 2002220918A1
- Authority
- AU
- Australia
- Prior art keywords
- salbutamol
- precursor
- optically
- optically pure
- isomer
- 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
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical class CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 title abstract 5
- 229960002052 salbutamol Drugs 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 abstract 3
- NDAUXUAQIAJITI-GFCCVEGCSA-N 4-[(1s)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound CC(C)(C)NC[C@@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-GFCCVEGCSA-N 0.000 abstract 3
- 239000002243 precursor Substances 0.000 abstract 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
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
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- 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)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for making optically Optically pure (R) and (S) salbutamol comprises obtaining the (R) or (S) isomer of either salbutamol or a salbutamol precursor in substantially optically pure form is obtained by resolving a racemic or optically impure mixture of enantiomers of salbutamol or of said a salbutamol precursor with either (L) or (D) tartaric acid, and where necessary converting said isomer of said precursor into either (R) or (S) salbutamol respectively; then optionally converting said optically pure (R) and/or (S) salbutamol into a pharmaceutically acceptable salt.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0030171.3A GB0030171D0 (en) | 2000-12-11 | 2000-12-11 | Process for preparing isomers of salbutamol |
| GB0030171 | 2000-12-11 | ||
| PCT/GB2001/005444 WO2002048090A1 (en) | 2000-12-11 | 2001-12-10 | Process for preparing isomers of salbutamol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2002220918A1 true AU2002220918A1 (en) | 2002-06-24 |
Family
ID=9904845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002220918A Abandoned AU2002220918A1 (en) | 2000-12-11 | 2001-12-10 | Process for preparing isomers of salbutamol |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US6995286B2 (en) |
| EP (1) | EP1349828B1 (en) |
| AT (1) | ATE291006T1 (en) |
| AU (1) | AU2002220918A1 (en) |
| CA (1) | CA2431400C (en) |
| DE (1) | DE60109494T2 (en) |
| ES (1) | ES2240335T3 (en) |
| GB (1) | GB0030171D0 (en) |
| PT (1) | PT1349828E (en) |
| WO (1) | WO2002048090A1 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0030171D0 (en) | 2000-12-11 | 2001-01-24 | Cipla Ltd | Process for preparing isomers of salbutamol |
| DK1671942T4 (en) | 2002-12-10 | 2014-09-22 | Sunovion Pharmaceuticals Inc | Aerosol formulation comprising levalbuterol L-tartrate salt |
| JP2007515402A (en) * | 2003-11-20 | 2007-06-14 | アルターアゴン プロプライエタリー リミテッド | Method for reducing body fat and weight of mammals and birds |
| CA2556921A1 (en) | 2004-05-20 | 2005-12-01 | Teva Pharmaceutical Fine Chemicals S.R.L. | Levalbuterol hydrochloride polymorph b |
| JP2008512434A (en) * | 2004-09-09 | 2008-04-24 | シプラ・リミテッド | Pharmaceutical composition comprising an isomer of a beta mimetic and an anticholinergic agent |
| US7579505B2 (en) * | 2004-12-17 | 2009-08-25 | Cipla Limited | Crystalline levosalbutamol sulphate and polymorphic forms thereof |
| EP2311793A1 (en) | 2004-12-17 | 2011-04-20 | Cipla Ltd. | Crystalline levosalbutamol sulphate (Form II) |
| TW200740779A (en) | 2005-07-22 | 2007-11-01 | Mitsubishi Pharma Corp | Intermediate compound for synthesizing pharmaceutical agent and production method thereof |
| WO2008015689A1 (en) | 2006-08-02 | 2008-02-07 | Aarti Healthcare Limited | A process for the preparation of optically pure r (-) salbutamol and its pharmaceutically acceptable salts |
| EP1935872A1 (en) * | 2006-12-11 | 2008-06-25 | Stirling Products Limited | Process for obtaining the R-enantiomer of salbutamol |
| CN101951773A (en) * | 2008-01-15 | 2011-01-19 | 塔加西普特公司 | Preparation and enantiomeric separation of 7-(3-pyridinyl)-1,7-diazaspiro[4.4] nonane and novel salt forms of the racemate and enantiomers |
| CN102260179A (en) * | 2010-05-24 | 2011-11-30 | 苏州睿克气雾医药有限公司 | Novel technology for resolving salbutamol sulfate |
| CN108947854B (en) * | 2018-06-30 | 2020-09-08 | 常州市阳光药业有限公司 | Method for resolving meta-hydroxylamine bitartrate and isomers thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1200886A (en) | 1966-09-23 | 1970-08-05 | Allen & Hanburys Ltd | Phenylaminoethanol derivatives |
| JPH0285247A (en) * | 1988-09-22 | 1990-03-26 | Kohjin Co Ltd | Optically active thiourea derivative |
| US5399765A (en) | 1994-05-23 | 1995-03-21 | Sepracor, Inc. | Enantioselective preparation of optically pure albuterol |
| US5545745A (en) * | 1994-05-23 | 1996-08-13 | Sepracor, Inc. | Enantioselective preparation of optically pure albuterol |
| AU2539399A (en) * | 1998-02-20 | 1999-09-06 | Flaccida Investments (Proprietary) Limited | Process for the production of optically enriched (r)- or (s)-albuterol |
| CN1173929C (en) * | 1999-10-19 | 2004-11-03 | 中国科学院成都有机化学研究所 | Process for preparing adrenin beta-excitomotors by combinaion and disconnection method |
| GB0030171D0 (en) | 2000-12-11 | 2001-01-24 | Cipla Ltd | Process for preparing isomers of salbutamol |
-
2000
- 2000-12-11 GB GBGB0030171.3A patent/GB0030171D0/en not_active Ceased
-
2001
- 2001-12-10 ES ES01270520T patent/ES2240335T3/en not_active Expired - Lifetime
- 2001-12-10 US US10/450,155 patent/US6995286B2/en not_active Ceased
- 2001-12-10 AU AU2002220918A patent/AU2002220918A1/en not_active Abandoned
- 2001-12-10 AT AT01270520T patent/ATE291006T1/en not_active IP Right Cessation
- 2001-12-10 WO PCT/GB2001/005444 patent/WO2002048090A1/en not_active Ceased
- 2001-12-10 PT PT01270520T patent/PT1349828E/en unknown
- 2001-12-10 US US12/402,752 patent/USRE43984E1/en not_active Expired - Lifetime
- 2001-12-10 CA CA002431400A patent/CA2431400C/en not_active Expired - Fee Related
- 2001-12-10 EP EP01270520A patent/EP1349828B1/en not_active Expired - Lifetime
- 2001-12-10 DE DE60109494T patent/DE60109494T2/en not_active Expired - Lifetime
- 2001-12-10 US US12/026,790 patent/USRE43844E1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1349828A1 (en) | 2003-10-08 |
| PT1349828E (en) | 2005-07-29 |
| DE60109494T2 (en) | 2005-08-04 |
| CA2431400C (en) | 2008-01-22 |
| USRE43844E1 (en) | 2012-12-04 |
| HK1060345A1 (en) | 2004-08-06 |
| EP1349828B1 (en) | 2005-03-16 |
| GB0030171D0 (en) | 2001-01-24 |
| DE60109494D1 (en) | 2005-04-21 |
| WO2002048090A1 (en) | 2002-06-20 |
| ATE291006T1 (en) | 2005-04-15 |
| USRE43984E1 (en) | 2013-02-05 |
| US6995286B2 (en) | 2006-02-07 |
| ES2240335T3 (en) | 2005-10-16 |
| CA2431400A1 (en) | 2002-06-20 |
| US20040054215A1 (en) | 2004-03-18 |
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