NZ588894A - Process for preparing (s)-pregabalin by chiral resolution - Google Patents
Process for preparing (s)-pregabalin by chiral resolutionInfo
- Publication number
- NZ588894A NZ588894A NZ588894A NZ58889409A NZ588894A NZ 588894 A NZ588894 A NZ 588894A NZ 588894 A NZ588894 A NZ 588894A NZ 58889409 A NZ58889409 A NZ 58889409A NZ 588894 A NZ588894 A NZ 588894A
- Authority
- NZ
- New Zealand
- Prior art keywords
- acid
- sulphonic
- camphor
- pregabalin
- tartaric
- Prior art date
Links
- 229960001233 pregabalin Drugs 0.000 title abstract 2
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000011975 tartaric acid Substances 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- CBEMVOYIUQADIA-ZETCQYMHSA-N (2s)-2-(3-bromophenyl)-2-hydroxyacetic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC(Br)=C1 CBEMVOYIUQADIA-ZETCQYMHSA-N 0.000 abstract 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 abstract 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract 1
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 abstract 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 abstract 1
- JNZWSZKRZCXVLX-UHFFFAOYSA-N 2-hydroxy-1-methyl-4-prop-1-en-2-ylcyclohexane-1-sulfonic acid Chemical compound CC(=C)C1CCC(C)(S(O)(=O)=O)C(O)C1 JNZWSZKRZCXVLX-UHFFFAOYSA-N 0.000 abstract 1
- VNTAONUWHQBAMC-UHFFFAOYSA-N 3-phenothiazin-10-ylpropanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C3=CC=CC=C3SC2=C1 VNTAONUWHQBAMC-UHFFFAOYSA-N 0.000 abstract 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 abstract 1
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- WXNXCEHXYPACJF-ZETCQYMHSA-N N-acetyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(C)=O WXNXCEHXYPACJF-ZETCQYMHSA-N 0.000 abstract 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-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
- 229960000669 acetylleucine Drugs 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- 239000001630 malic acid Substances 0.000 abstract 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Analytical Chemistry (AREA)
- Psychiatry (AREA)
- Toxicology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN679KO2008 | 2008-04-04 | ||
| PCT/GB2009/050326 WO2009122215A1 (en) | 2008-04-04 | 2009-04-02 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ588894A true NZ588894A (en) | 2012-12-21 |
Family
ID=40674128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ588894A NZ588894A (en) | 2008-04-04 | 2009-04-02 | Process for preparing (s)-pregabalin by chiral resolution |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20110124909A1 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2262761A1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2011516459A (cg-RX-API-DMAC10.html) |
| CN (1) | CN102089273A (cg-RX-API-DMAC10.html) |
| AU (1) | AU2009233536A1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2719892A1 (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ588894A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2009122215A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010110361A1 (ja) | 2009-03-26 | 2010-09-30 | 第一三共株式会社 | 二環性γ－アミノ酸誘導体の製造方法 |
| HUP1000186A2 (en) | 2010-04-08 | 2011-10-28 | Richter Gedeon Nyrt | Novel industrial process of preparing (s)-(+) pregabalin |
| JP2013539470A (ja) * | 2010-09-01 | 2013-10-24 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ロルカセリンと光学活性な酸との塩 |
| EP2527319A1 (en) * | 2011-05-24 | 2012-11-28 | Laboratorios Del. Dr. Esteve, S.A. | Crystalline forms of pregabalin and co-formers in the treatment of pain |
| JP6482465B2 (ja) | 2012-11-07 | 2019-03-13 | ハイカル リミテッド | プレガバリンの調製方法 |
| CN105085290A (zh) * | 2015-08-18 | 2015-11-25 | 太仓运通生物化工有限公司 | 一种合成普瑞巴林的方法 |
| CN105348124A (zh) * | 2015-11-26 | 2016-02-24 | 太仓运通生物化工有限公司 | 一种以氧代吡咯烷为中间体合成普瑞巴林的方法 |
| CN108456144A (zh) * | 2017-11-03 | 2018-08-28 | 乳源东阳光药业有限公司 | 一种小粒径晶状普瑞巴林、组合物及其制备工艺 |
| CN113801031B (zh) * | 2021-10-26 | 2023-12-26 | 浙江华海药业股份有限公司 | 一种普瑞巴林的纯化方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637767A (en) * | 1995-06-07 | 1997-06-10 | Warner-Lambert Company | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| US20060270871A1 (en) * | 2005-05-30 | 2006-11-30 | Khanduri Chandra H | Polymorphic form i of pregabalin and processes for its preparation |
| EP1736462A1 (en) * | 2005-06-22 | 2006-12-27 | Sandoz AG | Recovery of optically active tartaric acid resolving agents |
| WO2008117305A2 (en) * | 2007-03-28 | 2008-10-02 | Glenmark Pharmaceuticals Limited | A novel process for preparing pregabalin and its acid addition salts |
| WO2008138874A1 (en) * | 2007-05-09 | 2008-11-20 | Chemo Ibérica, S.A. | Process for preparing (s)-pregabalin by optical resolution of racemic pregabalin |
| US8168828B2 (en) * | 2007-06-25 | 2012-05-01 | Msn Laboratories, Limited | Process for the preparation of pregabalin |
| WO2009044409A2 (en) * | 2007-10-01 | 2009-04-09 | Natco Pharma Limited | Novel resolution process for pregabalin |
-
2009
- 2009-04-02 AU AU2009233536A patent/AU2009233536A1/en not_active Abandoned
- 2009-04-02 EP EP09726578A patent/EP2262761A1/en not_active Withdrawn
- 2009-04-02 US US12/935,764 patent/US20110124909A1/en not_active Abandoned
- 2009-04-02 WO PCT/GB2009/050326 patent/WO2009122215A1/en not_active Ceased
- 2009-04-02 JP JP2011502439A patent/JP2011516459A/ja not_active Withdrawn
- 2009-04-02 CA CA2719892A patent/CA2719892A1/en not_active Abandoned
- 2009-04-02 CN CN2009801189268A patent/CN102089273A/zh active Pending
- 2009-04-02 NZ NZ588894A patent/NZ588894A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2719892A1 (en) | 2009-10-08 |
| CN102089273A (zh) | 2011-06-08 |
| US20110124909A1 (en) | 2011-05-26 |
| WO2009122215A1 (en) | 2009-10-08 |
| JP2011516459A (ja) | 2011-05-26 |
| EP2262761A1 (en) | 2010-12-22 |
| AU2009233536A1 (en) | 2009-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| LAPS | Patent lapsed |