CN1596256A - 左氧氟沙星的纯化方法 - Google Patents
左氧氟沙星的纯化方法 Download PDFInfo
- Publication number
- CN1596256A CN1596256A CNA028236440A CN02823644A CN1596256A CN 1596256 A CN1596256 A CN 1596256A CN A028236440 A CNA028236440 A CN A028236440A CN 02823644 A CN02823644 A CN 02823644A CN 1596256 A CN1596256 A CN 1596256A
- Authority
- CN
- China
- Prior art keywords
- levofloxacin
- described method
- purifying
- solvent
- mixture
- 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.)
- Pending
Links
- 229960003376 levofloxacin Drugs 0.000 title claims abstract description 111
- 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 description 110
- 238000000034 method Methods 0.000 title claims description 50
- 238000000746 purification Methods 0.000 title description 3
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 19
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 19
- 239000002798 polar solvent Substances 0.000 claims abstract description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 45
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 39
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 20
- 235000006708 antioxidants Nutrition 0.000 claims description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 17
- 238000010992 reflux Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 12
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 11
- -1 levofloxacin N-oxide compound Chemical class 0.000 claims description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical group OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 6
- 230000017858 demethylation Effects 0.000 claims description 6
- 238000010520 demethylation reaction Methods 0.000 claims description 6
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 claims description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Chemical group OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- SRUQARLMFOLRDN-UHFFFAOYSA-N 1-(2,4,5-Trihydroxyphenyl)-1-butanone Chemical compound CCCC(=O)C1=CC(O)=C(O)C=C1O SRUQARLMFOLRDN-UHFFFAOYSA-N 0.000 claims description 2
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims description 2
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 claims description 2
- 241000147041 Guaiacum officinale Species 0.000 claims description 2
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims description 2
- 235000010376 calcium ascorbate Nutrition 0.000 claims description 2
- 229940047036 calcium ascorbate Drugs 0.000 claims description 2
- 239000011692 calcium ascorbate Substances 0.000 claims description 2
- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 claims description 2
- 229940091561 guaiac Drugs 0.000 claims description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 2
- KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001206 natural gum Polymers 0.000 claims description 2
- 235000010388 propyl gallate Nutrition 0.000 claims description 2
- 239000000473 propyl gallate Substances 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 2
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 2
- 229960005055 sodium ascorbate Drugs 0.000 claims description 2
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 2
- 235000010384 tocopherol Nutrition 0.000 claims description 2
- 229930003799 tocopherol Chemical group 0.000 claims description 2
- 239000011732 tocopherol Chemical group 0.000 claims description 2
- 229960001295 tocopherol Drugs 0.000 claims description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical group OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims 3
- 230000003647 oxidation Effects 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 19
- 238000003828 vacuum filtration Methods 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- 238000001291 vacuum drying Methods 0.000 description 14
- 206010013786 Dry skin Diseases 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 238000005406 washing Methods 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 239000002994 raw material Substances 0.000 description 8
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 5
- 229960001699 ofloxacin Drugs 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940124307 fluoroquinolone Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 2
- AAEQXEDPVFIFDK-UHFFFAOYSA-N 3-(4-fluorobenzoyl)-2-(2-methylpropanoyl)-n,3-diphenyloxirane-2-carboxamide Chemical compound C=1C=CC=CC=1NC(=O)C1(C(=O)C(C)C)OC1(C=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1 AAEQXEDPVFIFDK-UHFFFAOYSA-N 0.000 description 2
- NVKWWNNJFKZNJO-YFKPBYRVSA-N Ofloxacin impurity a Chemical compound N1([C@@H](C)CO2)C=C(C(O)=O)C(=O)C3=C1C2=C(F)C(F)=C3 NVKWWNNJFKZNJO-YFKPBYRVSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical class C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- QDEJGQKJMKXYLM-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine Chemical class C1=CC2=NC=CC=C2C2=C1C=CNO2 QDEJGQKJMKXYLM-UHFFFAOYSA-N 0.000 description 1
- VRPQEKUZCDCTNO-UHFFFAOYSA-N 3-piperazin-1-yl-1h-quinolin-2-one Chemical class O=C1NC2=CC=CC=C2C=C1N1CCNCC1 VRPQEKUZCDCTNO-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 description 1
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940089519 levaquin Drugs 0.000 description 1
- MVLAUMUQGRQERL-JTQLQIEISA-N levofloxacin n-oxide Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CC[N+](C)([O-])CC1 MVLAUMUQGRQERL-JTQLQIEISA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
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
- 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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33431601P | 2001-11-29 | 2001-11-29 | |
| US60/334,316 | 2001-11-29 | ||
| US35493902P | 2002-02-11 | 2002-02-11 | |
| US60/354,939 | 2002-02-11 | ||
| US26296502A | 2002-10-03 | 2002-10-03 | |
| US10/263,192 | 2002-10-03 | ||
| US10/262,965 | 2002-10-03 | ||
| US10/263,192 US7629458B2 (en) | 2001-10-03 | 2002-10-03 | Preparation of levofloxacin and hemihydrate thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1596256A true CN1596256A (zh) | 2005-03-16 |
Family
ID=31892240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA028236440A Pending CN1596256A (zh) | 2001-11-29 | 2002-11-27 | 左氧氟沙星的纯化方法 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1460997A4 (pl) |
| JP (3) | JP2005527484A (pl) |
| CN (1) | CN1596256A (pl) |
| AU (1) | AU2002365416A1 (pl) |
| CA (1) | CA2466860A1 (pl) |
| HR (1) | HRP20040546A2 (pl) |
| HU (1) | HUP0500285A3 (pl) |
| IL (1) | IL162172A0 (pl) |
| IS (1) | IS7288A (pl) |
| MX (1) | MXPA04005196A (pl) |
| NO (1) | NO20042731L (pl) |
| PL (1) | PL374558A1 (pl) |
| WO (1) | WO2003045329A2 (pl) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1321121C (zh) * | 2005-04-21 | 2007-06-13 | 浙江医药股份有限公司新昌制药厂 | 左氧氟沙星制备及后处理方法 |
| CN102070650A (zh) * | 2011-01-28 | 2011-05-25 | 山东省药品检验所 | 左氧氟沙星-n-氧化物的制备方法 |
| CN105823851A (zh) * | 2015-12-15 | 2016-08-03 | 浙江海洋学院 | 一种检测海水中氧氟沙星对映体的方法 |
| CN108218892A (zh) * | 2018-03-16 | 2018-06-29 | 乐山职业技术学院 | 一种左氧氟沙星的纯化方法 |
| CN114507242A (zh) * | 2022-01-26 | 2022-05-17 | 上虞京新药业有限公司 | 高光学纯度左氧氟沙星的制备方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL161164A0 (en) | 2001-10-03 | 2004-08-31 | Teva Pharma | Preparation of levofloxacin and forms thereof |
| US20060276463A1 (en) * | 2002-12-16 | 2006-12-07 | Sharma Tarun K | Pure levofloxacin hemihydrate and processes for preparation thereof |
| KR100704641B1 (ko) * | 2004-07-21 | 2007-04-06 | 주식회사유한양행 | 고순도의 레보플록사신 제조방법 |
| JP2006273718A (ja) * | 2005-03-28 | 2006-10-12 | Shiono Chemical Co Ltd | レボフロキサシン・１／２水和物の製法 |
| 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 |
| US20120251685A1 (en) * | 2011-04-04 | 2012-10-04 | Martek Biosciences Corporation | Oil-in-Water Emulsions Comprising a Polyunsaturated Fatty Acid and Methods of Making the Same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK170473B1 (da) * | 1985-06-20 | 1995-09-11 | Daiichi Seiyaku Co | S(-)-pyridobenzoxazinforbindelser |
| US5237060A (en) * | 1985-12-10 | 1993-08-17 | Bayer Aktiengesellschaft | Process of preparing enantiomerically pure 1,8-bridged 4-quinolone-3-carboxylic acids |
| TW208013B (pl) * | 1990-03-01 | 1993-06-21 | Daiichi Co Ltd | |
| KR0131914B1 (ko) * | 1992-10-07 | 1998-04-17 | 조아퀸 가리데 센트멘나트 | 오플로옥사진, 레보플로옥사진과 이 유도체의 합성에 이용될 수 있는 벤조옥사진의 수득과정 |
| KR0125115B1 (ko) * | 1994-03-22 | 1997-12-05 | 김은영 | (-)피페라진 벤즈옥사진 유도체의 제조방법 |
| KR100309871B1 (ko) * | 1999-02-24 | 2001-10-29 | 윤종용 | (-)피리도벤즈옥사진 카르복실산 유도체의 제조방법 |
| IL161164A0 (en) * | 2001-10-03 | 2004-08-31 | Teva Pharma | Preparation of levofloxacin and forms thereof |
-
2002
- 2002-11-27 JP JP2003546834A patent/JP2005527484A/ja active Pending
- 2002-11-27 AU AU2002365416A patent/AU2002365416A1/en not_active Abandoned
- 2002-11-27 IL IL16217202A patent/IL162172A0/xx unknown
- 2002-11-27 PL PL02374558A patent/PL374558A1/pl not_active Application Discontinuation
- 2002-11-27 WO PCT/US2002/038182 patent/WO2003045329A2/en active Application Filing
- 2002-11-27 HU HU0500285A patent/HUP0500285A3/hu unknown
- 2002-11-27 CA CA002466860A patent/CA2466860A1/en not_active Abandoned
- 2002-11-27 CN CNA028236440A patent/CN1596256A/zh active Pending
- 2002-11-27 EP EP02791339A patent/EP1460997A4/en not_active Withdrawn
- 2002-11-27 MX MXPA04005196A patent/MXPA04005196A/es not_active Application Discontinuation
-
2004
- 2004-05-27 IS IS7288A patent/IS7288A/is unknown
- 2004-06-15 HR HR20040546A patent/HRP20040546A2/hr not_active Application Discontinuation
- 2004-06-29 NO NO20042731A patent/NO20042731L/no not_active Application Discontinuation
-
2006
- 2006-05-01 JP JP2006127862A patent/JP2006219496A/ja not_active Withdrawn
-
2007
- 2007-08-22 JP JP2007216178A patent/JP2008007517A/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1321121C (zh) * | 2005-04-21 | 2007-06-13 | 浙江医药股份有限公司新昌制药厂 | 左氧氟沙星制备及后处理方法 |
| CN102070650A (zh) * | 2011-01-28 | 2011-05-25 | 山东省药品检验所 | 左氧氟沙星-n-氧化物的制备方法 |
| CN102070650B (zh) * | 2011-01-28 | 2012-06-27 | 山东省药品检验所 | 左氧氟沙星-n-氧化物的制备方法 |
| CN105823851A (zh) * | 2015-12-15 | 2016-08-03 | 浙江海洋学院 | 一种检测海水中氧氟沙星对映体的方法 |
| CN108218892A (zh) * | 2018-03-16 | 2018-06-29 | 乐山职业技术学院 | 一种左氧氟沙星的纯化方法 |
| CN114507242A (zh) * | 2022-01-26 | 2022-05-17 | 上虞京新药业有限公司 | 高光学纯度左氧氟沙星的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0500285A2 (hu) | 2005-06-28 |
| EP1460997A4 (en) | 2005-06-15 |
| WO2003045329A3 (en) | 2004-02-19 |
| HUP0500285A3 (en) | 2009-03-30 |
| IS7288A (is) | 2004-06-21 |
| IL162172A0 (en) | 2005-11-20 |
| WO2003045329A2 (en) | 2003-06-05 |
| NO20042731L (no) | 2004-06-29 |
| JP2006219496A (ja) | 2006-08-24 |
| JP2005527484A (ja) | 2005-09-15 |
| EP1460997A2 (en) | 2004-09-29 |
| CA2466860A1 (en) | 2003-06-05 |
| JP2008007517A (ja) | 2008-01-17 |
| AU2002365416A1 (en) | 2003-06-10 |
| MXPA04005196A (es) | 2005-11-23 |
| PL374558A1 (pl) | 2005-10-31 |
| HRP20040546A2 (en) | 2004-10-31 |
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