ATE248148T1 - Verfahren zur herstellung von levobupivacaine und analoge - Google Patents
Verfahren zur herstellung von levobupivacaine und analogeInfo
- Publication number
- ATE248148T1 ATE248148T1 AT95934739T AT95934739T ATE248148T1 AT E248148 T1 ATE248148 T1 AT E248148T1 AT 95934739 T AT95934739 T AT 95934739T AT 95934739 T AT95934739 T AT 95934739T AT E248148 T1 ATE248148 T1 AT E248148T1
- Authority
- AT
- Austria
- Prior art keywords
- pct
- levobupivacaine
- amidation
- alkylation
- resultant
- Prior art date
Links
- LEBVLXFERQHONN-INIZCTEOSA-N levobupivacaine Chemical compound CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-INIZCTEOSA-N 0.000 title abstract 2
- 229960004288 levobupivacaine Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 230000009435 amidation Effects 0.000 abstract 2
- 238000007112 amidation reaction Methods 0.000 abstract 2
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 abstract 1
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 abstract 1
- AUGDEGXARBUSFU-UHFFFAOYSA-N piperidin-1-ium-2-carboxylic acid;chloride Chemical compound Cl.OC(=O)C1CCCCN1 AUGDEGXARBUSFU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compounds Of Unknown Constitution (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9421478A GB9421478D0 (en) | 1994-10-25 | 1994-10-25 | Process and compounds |
| GBGB9504925.0A GB9504925D0 (en) | 1995-03-10 | 1995-03-10 | Process for preparing analgesic agents |
| PCT/GB1995/002514 WO1996012700A1 (en) | 1994-10-25 | 1995-10-23 | Process for preparing levobupivacaine and analogues thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE248148T1 true ATE248148T1 (de) | 2003-09-15 |
Family
ID=26305864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT95934739T ATE248148T1 (de) | 1994-10-25 | 1995-10-23 | Verfahren zur herstellung von levobupivacaine und analoge |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5777124A (de) |
| EP (1) | EP0788481B1 (de) |
| JP (1) | JP4118946B2 (de) |
| AT (1) | ATE248148T1 (de) |
| AU (1) | AU694569B2 (de) |
| CA (1) | CA2200356C (de) |
| DE (1) | DE69531624T2 (de) |
| DK (1) | DK0788481T3 (de) |
| ES (1) | ES2203645T3 (de) |
| MX (1) | MX9703025A (de) |
| PT (1) | PT788481E (de) |
| WO (1) | WO1996012700A1 (de) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1433782A4 (de) * | 2001-09-10 | 2005-04-27 | Mercian Corp | Verfahren zur herstellung eines pipecolamidderivats |
| BRPI0104491B8 (pt) * | 2001-10-10 | 2021-05-25 | Cristalia Produtos Quim Farmaceuticos Ltda | n-(2,6-dimetilfenil)-1-propil-2-piperidinocarboxamida; processo de obtenção dos enantiômeros; mistura não racêmica dos anantiômeros e seu processo de obtenção e composição farmacêutica. |
| US20040001889A1 (en) | 2002-06-25 | 2004-01-01 | Guohua Chen | Short duration depot formulations |
| EP1575569B1 (de) | 2002-12-13 | 2010-09-29 | Durect Corporation | Orale darreichungsform mit flüssigen hochviskosen trägersystemen |
| RS52198B (sr) | 2004-09-17 | 2012-10-31 | Durect Corporation | Rastvor lokalnog anestetika koji sadrži saib sa održivim delovanjem |
| US20060270708A1 (en) * | 2005-05-25 | 2006-11-30 | Navinta Llc | Novel process for preparation of isotonic aqueous injection of ropivacaine |
| US7683175B2 (en) * | 2005-06-06 | 2010-03-23 | Navinta, Llc | Process of making optically pure L-pipecolic acid and process of making anesthetics and intermediates therefrom |
| US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
| WO2007123405A1 (en) * | 2006-04-25 | 2007-11-01 | Dishman Pharmaceuticals And Chemicals Ltd. | Ropivacaine hydrochloride anhydrate and the preparation thereof |
| ES2388355T3 (es) | 2006-11-03 | 2012-10-11 | Durect Corporation | Sistemas de suministro transdémico que comprenden bupivacaína |
| KR100844336B1 (ko) | 2007-01-16 | 2008-07-07 | 하나제약 주식회사 | 레보부피바카인 및 이의 염산염의 신규한 제조방법 |
| EP2219622A1 (de) * | 2007-12-06 | 2010-08-25 | Durect Corporation | Verfahren zur behandlung von schmerzen, arthritischen zuständen oder entzündung im zusammenhang mit einer chronischen erkrankung |
| ATE555094T1 (de) * | 2008-01-15 | 2012-05-15 | Pharmathen Sa | Verfahren zur herstellung von pipecol-2-säure-2', 6'-xylidid als zwischenprodukt für die herstellung von lokalanästhetika |
| US20100260844A1 (en) | 2008-11-03 | 2010-10-14 | Scicinski Jan J | Oral pharmaceutical dosage forms |
| CN102558030A (zh) * | 2010-12-11 | 2012-07-11 | 山东方明药业股份有限公司 | 1-n-(2，6-二甲基苯基)-2-哌啶甲酰胺的合成 |
| CN103086954A (zh) * | 2013-02-04 | 2013-05-08 | 山东省医药工业研究所 | 一种制备罗哌卡因的方法 |
| JP2016515523A (ja) | 2013-03-15 | 2016-05-30 | デュレクト コーポレーション | 溶解変動性を低減させるためのレオロジー改質剤を有する組成物 |
| CN103664744B (zh) * | 2013-11-30 | 2015-07-15 | 山东永泰化工有限公司 | 一种左布比卡因的制备方法 |
| CN104003930B (zh) * | 2014-06-13 | 2016-06-08 | 山东金诃药物研究开发有限公司 | 一种盐酸罗哌卡因的制备方法 |
| CN105418489A (zh) * | 2016-01-22 | 2016-03-23 | 江苏宝众宝达药业有限公司 | 一种布比卡因的合成方法 |
| MY205229A (en) | 2016-07-06 | 2024-10-08 | Durect Corp | Oral dosage form with drug composition, barrier layer and drug layer |
| CN106187864B (zh) * | 2016-07-11 | 2018-11-23 | 江苏天和制药有限公司 | 一种由盐酸布比卡因制备高纯度布比卡因碱的方法 |
| CN109438331A (zh) * | 2018-09-20 | 2019-03-08 | 山东科源制药股份有限公司 | 一种制备罗哌卡因中间体的方法 |
| BR112022013784A2 (pt) | 2020-01-13 | 2022-10-11 | Durect Corp | Sistemas de distribuição de fármacos de liberação prolongada com impurezas reduzidas e métodos relacionados |
| CN111548303A (zh) * | 2020-06-28 | 2020-08-18 | 山东美泰医药有限公司 | 一种盐酸左布比卡因的杂质及其制备和分析方法 |
| CA3203561A1 (en) | 2021-01-12 | 2022-07-21 | Adrian Neil Verity | Sustained release drug delivery systems and related methods |
| CN112939848B (zh) * | 2021-02-25 | 2022-07-01 | 浙江工业大学 | 一种布比卡因及其中间体(s)-2-哌啶甲酸的制备方法 |
| US12070454B1 (en) | 2022-05-05 | 2024-08-27 | Pfof Llc | Anesthetic nerve block and method |
| CA3251322A1 (en) | 2022-05-05 | 2023-11-09 | Pfof Llc | ANESTHETIC NERVE BLOCK AND PROCEDURE |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6803337A (de) * | 1967-03-20 | 1968-09-23 | ||
| AU560367B2 (en) * | 1983-08-01 | 1987-04-02 | Astra Lakemedel Aktiebolag | L-n-n-propylpipecolic acid-2,6-xylidide and method for preparing the same |
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
-
1995
- 1995-10-23 EP EP95934739A patent/EP0788481B1/de not_active Expired - Lifetime
- 1995-10-23 JP JP51373996A patent/JP4118946B2/ja not_active Expired - Fee Related
- 1995-10-23 DE DE69531624T patent/DE69531624T2/de not_active Expired - Lifetime
- 1995-10-23 ES ES95934739T patent/ES2203645T3/es not_active Expired - Lifetime
- 1995-10-23 PT PT95934739T patent/PT788481E/pt unknown
- 1995-10-23 DK DK95934739T patent/DK0788481T3/da active
- 1995-10-23 MX MX9703025A patent/MX9703025A/es unknown
- 1995-10-23 US US08/836,449 patent/US5777124A/en not_active Expired - Lifetime
- 1995-10-23 WO PCT/GB1995/002514 patent/WO1996012700A1/en not_active Ceased
- 1995-10-23 AU AU37049/95A patent/AU694569B2/en not_active Ceased
- 1995-10-23 AT AT95934739T patent/ATE248148T1/de not_active IP Right Cessation
- 1995-10-23 CA CA002200356A patent/CA2200356C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PT788481E (pt) | 2004-01-30 |
| US5777124A (en) | 1998-07-07 |
| DK0788481T3 (da) | 2003-12-01 |
| EP0788481A1 (de) | 1997-08-13 |
| DE69531624D1 (de) | 2003-10-02 |
| CA2200356C (en) | 2007-07-31 |
| AU3704995A (en) | 1996-05-15 |
| JPH10507748A (ja) | 1998-07-28 |
| EP0788481B1 (de) | 2003-08-27 |
| JP4118946B2 (ja) | 2008-07-16 |
| WO1996012700A1 (en) | 1996-05-02 |
| MX9703025A (es) | 1997-10-31 |
| AU694569B2 (en) | 1998-07-23 |
| DE69531624T2 (de) | 2004-06-17 |
| ES2203645T3 (es) | 2004-04-16 |
| CA2200356A1 (en) | 1996-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification |
Ref document number: 0788481 Country of ref document: EP |
|
| REN | Ceased due to non-payment of the annual fee |