CA2573129A1 - Procede pour la preparation de levofloxacine ou de son hydrate - Google Patents
Procede pour la preparation de levofloxacine ou de son hydrate Download PDFInfo
- Publication number
- CA2573129A1 CA2573129A1 CA002573129A CA2573129A CA2573129A1 CA 2573129 A1 CA2573129 A1 CA 2573129A1 CA 002573129 A CA002573129 A CA 002573129A CA 2573129 A CA2573129 A CA 2573129A CA 2573129 A1 CA2573129 A1 CA 2573129A1
- Authority
- CA
- Canada
- Prior art keywords
- mixed solvent
- levofloxacin
- ethyl acetate
- monohydrate
- water
- 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.)
- Granted
Links
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 title claims abstract 4
- 229960003376 levofloxacin Drugs 0.000 title claims abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 7
- 239000012046 mixed solvent Substances 0.000 claims abstract 6
- SUIQUYDRLGGZOL-RCWTXCDDSA-N levofloxacin hemihydrate Chemical compound O.C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1.C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 SUIQUYDRLGGZOL-RCWTXCDDSA-N 0.000 claims abstract 4
- 150000004682 monohydrates Chemical class 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims abstract 2
- 238000010992 reflux Methods 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Abstract
La présente invention a trait à un procédé de préparation de semi-hydrate ou de monohydrate de lévofloxacine sans impuretés, c'est à dire les impuretés B, C, D, E, et F. Le procédé comprend: (a) l'ajout de lévofloxacine à un nouveau mélange de solvant; (b) l'ébullition au reflux du mélange obtenu en (a) pour former une solution; et (c) la récupération de semi-hydrate ou monohydrate de lévofloxacine à partir de la solution obtenue en (b).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020040056637A KR100704641B1 (ko) | 2004-07-21 | 2004-07-21 | 고순도의 레보플록사신 제조방법 |
| KR10-2004-0056637 | 2004-07-21 | ||
| PCT/KR2005/002294 WO2006009374A1 (fr) | 2004-07-21 | 2005-07-18 | Procede pour la preparation de levofloxacine ou de son hydrate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2573129A1 true CA2573129A1 (fr) | 2006-01-26 |
| CA2573129C CA2573129C (fr) | 2012-10-16 |
Family
ID=35785447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2573129A Expired - Fee Related CA2573129C (fr) | 2004-07-21 | 2005-07-18 | Procede pour la preparation de levofloxacine ou de son hydrate |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP5065020B2 (fr) |
| KR (1) | KR100704641B1 (fr) |
| CA (1) | CA2573129C (fr) |
| WO (1) | WO2006009374A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7629458B2 (en) | 2001-10-03 | 2009-12-08 | Teva Pharmaceutical Industries Ltd. | Preparation of levofloxacin and hemihydrate thereof |
| US7964723B2 (en) | 2008-08-02 | 2011-06-21 | Apeloa-Kangyu | And practical process for exclusively producing (S)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido-[1,2,3,de][1,4]benzoxazine-6-carboxylic acid hemihydrate |
| CN111855840A (zh) * | 2020-06-30 | 2020-10-30 | 辰欣药业股份有限公司 | 一种盐酸左氧氟沙星注射液中有关物质的检测方法 |
| CN116953096A (zh) * | 2022-12-24 | 2023-10-27 | 华夏生生药业(北京)有限公司 | 一种左氧氟沙星注射液杂质检测方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4777253A (en) * | 1986-04-25 | 1988-10-11 | Abbott Laboratories | Process for preparation of racemate and optically active ofloxacin and related derivatives |
| JP3105572B2 (ja) * | 1990-03-01 | 2000-11-06 | 第一製薬株式会社 | 水和物の選択的製法 |
| TW208013B (fr) * | 1990-03-01 | 1993-06-21 | Daiichi Co Ltd | |
| KR100309871B1 (ko) * | 1999-02-24 | 2001-10-29 | 윤종용 | (-)피리도벤즈옥사진 카르복실산 유도체의 제조방법 |
| AU2002365416A1 (en) * | 2001-11-29 | 2003-06-10 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
| JP2004099494A (ja) * | 2002-09-09 | 2004-04-02 | Shiono Chemical Co Ltd | 光学活性三環式化合物の製造方法 |
| AU2003285625A1 (en) * | 2002-12-16 | 2004-07-09 | Ranbaxy Laboratories Limited | Pure levofloxacin hemihydrate and processes for preparation thereof |
-
2004
- 2004-07-21 KR KR1020040056637A patent/KR100704641B1/ko active IP Right Grant
-
2005
- 2005-07-18 WO PCT/KR2005/002294 patent/WO2006009374A1/fr active Application Filing
- 2005-07-18 CA CA2573129A patent/CA2573129C/fr not_active Expired - Fee Related
- 2005-07-18 JP JP2007522417A patent/JP5065020B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008507507A (ja) | 2008-03-13 |
| WO2006009374A1 (fr) | 2006-01-26 |
| CA2573129C (fr) | 2012-10-16 |
| KR20060009155A (ko) | 2006-01-31 |
| KR100704641B1 (ko) | 2007-04-06 |
| JP5065020B2 (ja) | 2012-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20220718 |