WO2003028664A2 - Preparation of levofloxacin and forms thereof - Google Patents
Preparation of levofloxacin and forms thereof Download PDFInfo
- Publication number
- WO2003028664A2 WO2003028664A2 PCT/US2002/031850 US0231850W WO03028664A2 WO 2003028664 A2 WO2003028664 A2 WO 2003028664A2 US 0231850 W US0231850 W US 0231850W WO 03028664 A2 WO03028664 A2 WO 03028664A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- levofloxacin
- solvent
- mixture
- polar solvent
- elevated temperature
- Prior art date
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 description 137
- 229960003376 levofloxacin Drugs 0.000 title claims abstract description 133
- 238000002360 preparation method Methods 0.000 title description 24
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 239000002798 polar solvent Substances 0.000 claims abstract description 51
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims abstract description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 65
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 33
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000002002 slurry Substances 0.000 claims description 25
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 23
- 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 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 17
- 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 description 17
- 230000008569 process Effects 0.000 claims description 15
- 238000010992 reflux Methods 0.000 claims description 14
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- 239000012296 anti-solvent Substances 0.000 claims description 10
- 229940113088 dimethylacetamide Drugs 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 239000011877 solvent mixture Substances 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 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 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000000463 material Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 150000004682 monohydrates Chemical class 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 238000001757 thermogravimetry curve Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000004677 hydrates Chemical group 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229960001699 ofloxacin Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 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
- 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 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
- 108010054814 DNA Gyrase Proteins 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- WKRSSAPQZDHYRV-VIFPVBQESA-N Ofloxacin impurity e Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCNCC1 WKRSSAPQZDHYRV-VIFPVBQESA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 101710183280 Topoisomerase Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation 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 class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 239000003306 quinoline derived antiinfective agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- -1 tetraalkyl ammonium halides Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000002424 x-ray crystallography Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- Another embodiment of the invention is a method for preparing a levofloxacin form.
- the wet material was divided in two portions for drying. The first portion was dried under vacuum with stirring at 40°C for 21 hours and the second fraction was dried under vacuum with stirring at 60°C for 21 hours.
- Levofloxacin Form G was resulted after drying at 40°C for 3 or 6 hours, and after drying at 60°C for 3 hours.
- Levofloxacin Form B was resulted after drying at 40°C for 21 hours, and after drying at 60°C for 6, 9 and 21 hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL16116402A IL161164A0 (en) | 2001-10-03 | 2002-10-03 | Preparation of levofloxacin and forms thereof |
DE60215213T DE60215213T3 (en) | 2001-10-03 | 2002-10-03 | PREPARATION OF LEVOFLOXACIN HEMIHYDRATE |
JP2003532000A JP2005504818A (en) | 2001-10-03 | 2002-10-03 | Preparation of levofloxacin and its forms |
AU2002341990A AU2002341990A1 (en) | 2001-10-03 | 2002-10-03 | Preparation of levofloxacin and forms thereof |
CA002462023A CA2462023A1 (en) | 2001-10-03 | 2002-10-03 | Preparation of levofloxacin and forms thereof |
EP02776152A EP1451194B2 (en) | 2001-10-03 | 2002-10-03 | Preparation of levofloxacin hemihydrate |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US32695801P | 2001-10-03 | 2001-10-03 | |
US60/326,958 | 2001-10-03 | ||
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2003028664A2 true WO2003028664A2 (en) | 2003-04-10 |
WO2003028664A3 WO2003028664A3 (en) | 2003-11-20 |
Family
ID=27406493
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/031850 WO2003028664A2 (en) | 2001-10-03 | 2002-10-03 | Preparation of levofloxacin and forms thereof |
PCT/US2002/031851 WO2003028665A2 (en) | 2001-10-03 | 2002-10-03 | Methods for the purification of levofloxacin |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/031851 WO2003028665A2 (en) | 2001-10-03 | 2002-10-03 | Methods for the purification of levofloxacin |
Country Status (11)
Country | Link |
---|---|
US (2) | US7629458B2 (en) |
EP (3) | EP1451194B2 (en) |
JP (5) | JP2005504818A (en) |
AT (1) | ATE341553T1 (en) |
AU (2) | AU2002341991A1 (en) |
CA (1) | CA2462023A1 (en) |
DE (1) | DE60215213T3 (en) |
ES (1) | ES2272781T5 (en) |
IL (1) | IL161164A0 (en) |
PT (1) | PT1451194E (en) |
WO (2) | WO2003028664A2 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1460997A2 (en) * | 2001-11-29 | 2004-09-29 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
WO2006030452A1 (en) * | 2004-09-17 | 2006-03-23 | Matrix Laboratories Ltd | An improved process for the preparation of levofloxacin hemihydrate |
JP2006104184A (en) * | 2004-09-30 | 2006-04-20 | Lab Servier | (alpha)-CRYSTALLINE FORM OF STRONTIUM RANELATE, METHOD FOR PRODUCING THE SAME AND MEDICINAL COMPOSITION CONTAINING THE SAME |
JP2006273718A (en) * | 2005-03-28 | 2006-10-12 | Shiono Chemical Co Ltd | Method for producing levofloxacin-1/2 hydrate |
CN100412075C (en) * | 2004-06-22 | 2008-08-20 | 浙江医药股份有限公司新昌制药厂 | Process for preparing L-ofloxacin and ofloxacin |
US7425628B2 (en) | 2001-10-03 | 2008-09-16 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
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 |
CN102146087A (en) * | 2010-02-10 | 2011-08-10 | 广东东阳光药业有限公司 | Method for preparing high-purity levofloxacin semihydrate |
US11065237B2 (en) | 2013-11-15 | 2021-07-20 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003028664A2 (en) | 2001-10-03 | 2003-04-10 | Teva Pharmaceutical Industries Ltd. | Preparation of levofloxacin and forms thereof |
US20070244318A1 (en) * | 2004-11-08 | 2007-10-18 | Rao Davuluri R | Process for the Preparation of Levofloxacin Hemihydrate |
US7902227B2 (en) | 2007-07-27 | 2011-03-08 | Janssen Pharmaceutica Nv. | C-7 isoxazolinyl quinolone / naphthyridine derivatives useful as antibacterial agents |
KR20130043611A (en) * | 2010-02-25 | 2013-04-30 | 다이이찌 산쿄 가부시키가이샤 | Ophthalmic solution for treating ocular infection comprising levofloxacin or salt thereof or solvate of the same, method for treating ocular infection, levofloxacin or salt thereof or solvate of the same, and use thereof |
CN102558197A (en) * | 2012-01-11 | 2012-07-11 | 浙江医药股份有限公司新昌制药厂 | Preparation method of levofloxacin-N-oxide |
CN102850377B (en) * | 2012-09-04 | 2014-05-21 | 苏州弘森药业有限公司 | Preparation method of levofloxacin hydrochloride |
CN114507242B (en) * | 2022-01-26 | 2023-05-19 | 上虞京新药业有限公司 | Preparation method of levofloxacin with high optical purity |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5545737A (en) * | 1990-03-01 | 1996-08-13 | Daiichi Pharmaceutical Co., Ltd. | Process for selectively producing an (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 or monohydrate |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5746986A (en) | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
DK170473B1 (en) | 1985-06-20 | 1995-09-11 | Daiichi Seiyaku Co | S (-) - pyridobenzoxazinforbindelser |
JPH0747592B2 (en) | 1985-06-20 | 1995-05-24 | 第一製薬株式会社 | Pyridobenzoxazine derivative |
US5237060A (en) | 1985-12-10 | 1993-08-17 | Bayer Aktiengesellschaft | Process of preparing enantiomerically pure 1,8-bridged 4-quinolone-3-carboxylic acids |
DE3543513A1 (en) | 1985-12-10 | 1987-06-11 | Bayer Ag | ENANTIOMER-PURE 1,8-BRIDGED 4-CHINOLON-3-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE MEDICINAL PRODUCTS CONTAINING THEM AND THEIR USE FOR THE PRODUCTION OF MEDICINAL PRODUCTS |
JPS62198685A (en) | 1986-02-26 | 1987-09-02 | Kyorin Pharmaceut Co Ltd | Quinolonecarboxylic acid derivative and production thereof |
US4777253A (en) | 1986-04-25 | 1988-10-11 | Abbott Laboratories | Process for preparation of racemate and optically active ofloxacin and related derivatives |
AU4376589A (en) | 1988-11-07 | 1990-05-10 | Gist-Brocades N.V. | Optically active benzoxazines and benzothiazines |
JP3105572B2 (en) | 1990-03-01 | 2000-11-06 | 第一製薬株式会社 | Selective production of hydrate |
KR920003605B1 (en) | 1990-03-27 | 1992-05-04 | 한국과학기술연구원 | Process for preparing piperazinyl quinolone derivatives |
DE4019023A1 (en) | 1990-06-14 | 1991-12-19 | Bayer Ag | METHOD FOR PRODUCING CHINOLINE CARBONIC ACIDS |
DE4210941A1 (en) | 1992-04-02 | 1993-10-07 | Bayer Ag | New 9-fluoro-7.oxo-7H-pyrido [1,2,3-d, e] [1,4] benzoxacin-6-carboxylic acids and esters |
JPH0632776A (en) | 1992-07-14 | 1994-02-08 | Mitsubishi Rayon Co Ltd | Method for preventing oxidation of n-@(3754/24)d-alpha--methyl-beta-mercaptopropionyl)-l-proline |
EP0619311A1 (en) | 1992-10-07 | 1994-10-12 | Derivados Del Etilo, S.A. | Process for obtaining benzoxazines useful for the synthesis of ofloxacin, levofloxacin and derivatives thereof |
ES2055656B1 (en) | 1992-10-07 | 1995-11-16 | Etilo Derivados | PROCEDURE FOR OBTAINING USEFUL BENZOXAZINES FOR SYNTHESIS OF OFLOXACIN, LEVOFLOXACIN AND DERIVATIVES. |
KR0125115B1 (en) | 1994-03-22 | 1997-12-05 | 김은영 | Process for preparing piperazinyl quinolone derivatives |
DE19729879C2 (en) | 1997-07-11 | 1999-07-08 | Mann Gerhard Chem Pharm Fab | Storage stable ophthalmic compositions comprising diclofenac and ofloxacin |
JPH11349589A (en) | 1997-12-24 | 1999-12-21 | Sankyo Co Ltd | Condensed ring quinolinecarboxylic derivative |
KR100309871B1 (en) | 1999-02-24 | 2001-10-29 | 윤종용 | Process for Preparing (-)Pyridobenzoxazine Carboxylic Acid Derivatives |
DE19826050A1 (en) | 1998-06-12 | 1999-12-16 | Bayer Ag | Process for the preparation of quinolonic and naphthyridonecarboxylic acids and their esters |
EP1211254B1 (en) | 1999-09-08 | 2014-05-07 | Daiichi Sankyo Company, Limited | Process for the preparation of benzoxazine derivatives and intermediates therefor |
WO2003028664A2 (en) | 2001-10-03 | 2003-04-10 | Teva Pharmaceutical Industries Ltd. | Preparation of levofloxacin and forms thereof |
US7425628B2 (en) | 2001-10-03 | 2008-09-16 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
PL374558A1 (en) | 2001-11-29 | 2005-10-31 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
US20040152701A1 (en) | 2002-12-02 | 2004-08-05 | Dr. Reddy's Laboratories Limited | Novel anhydrous crystalline form of Levofloxacin and process for preparation there of |
US20060276463A1 (en) | 2002-12-16 | 2006-12-07 | Sharma Tarun K | Pure levofloxacin hemihydrate and processes for preparation thereof |
KR100704641B1 (en) | 2004-07-21 | 2007-04-06 | 주식회사유한양행 | Methods for the preparation of levofloxacin having a high purity |
US7678903B2 (en) | 2004-09-17 | 2010-03-16 | Matrix Laboratories Limited | Process for the preparation of levofloxacin hemihydrate |
US20100029938A1 (en) | 2006-12-22 | 2010-02-04 | Farmaprojects, S. A. | Process for the preparation of an antibacterial quinolone compound |
-
2002
- 2002-10-03 WO PCT/US2002/031850 patent/WO2003028664A2/en active IP Right Grant
- 2002-10-03 PT PT02776152T patent/PT1451194E/en unknown
- 2002-10-03 WO PCT/US2002/031851 patent/WO2003028665A2/en not_active Application Discontinuation
- 2002-10-03 AU AU2002341991A patent/AU2002341991A1/en not_active Abandoned
- 2002-10-03 AU AU2002341990A patent/AU2002341990A1/en not_active Abandoned
- 2002-10-03 DE DE60215213T patent/DE60215213T3/en not_active Expired - Lifetime
- 2002-10-03 EP EP02776152A patent/EP1451194B2/en not_active Expired - Lifetime
- 2002-10-03 IL IL16116402A patent/IL161164A0/en unknown
- 2002-10-03 AT AT02776152T patent/ATE341553T1/en not_active IP Right Cessation
- 2002-10-03 US US10/263,192 patent/US7629458B2/en not_active Expired - Fee Related
- 2002-10-03 JP JP2003532000A patent/JP2005504818A/en not_active Withdrawn
- 2002-10-03 ES ES02776152T patent/ES2272781T5/en not_active Expired - Lifetime
- 2002-10-03 EP EP08015768A patent/EP1992629A1/en not_active Withdrawn
- 2002-10-03 CA CA002462023A patent/CA2462023A1/en not_active Abandoned
- 2002-10-03 EP EP06020684A patent/EP1772457A3/en not_active Withdrawn
-
2005
- 2005-05-26 US US11/137,348 patent/US20050222409A1/en not_active Abandoned
-
2006
- 2006-05-15 JP JP2006135884A patent/JP2006265261A/en not_active Withdrawn
- 2006-11-17 JP JP2006311904A patent/JP2007131628A/en active Pending
-
2007
- 2007-01-25 JP JP2007015655A patent/JP2007169288A/en active Pending
-
2008
- 2008-04-02 JP JP2008096368A patent/JP2008273956A/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5545737A (en) * | 1990-03-01 | 1996-08-13 | Daiichi Pharmaceutical Co., Ltd. | Process for selectively producing an (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 or monohydrate |
Non-Patent Citations (1)
Title |
---|
See also references of EP1451194A2 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7425628B2 (en) | 2001-10-03 | 2008-09-16 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
EP1460997A4 (en) * | 2001-11-29 | 2005-06-15 | Teva Pharma | Methods for the purification of levofloxacin |
EP1460997A2 (en) * | 2001-11-29 | 2004-09-29 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
CN100412075C (en) * | 2004-06-22 | 2008-08-20 | 浙江医药股份有限公司新昌制药厂 | Process for preparing L-ofloxacin and ofloxacin |
WO2006030452A1 (en) * | 2004-09-17 | 2006-03-23 | Matrix Laboratories Ltd | An improved process for the preparation of levofloxacin hemihydrate |
US7678903B2 (en) * | 2004-09-17 | 2010-03-16 | Matrix Laboratories Limited | Process for the preparation of levofloxacin hemihydrate |
JP2006104184A (en) * | 2004-09-30 | 2006-04-20 | Lab Servier | (alpha)-CRYSTALLINE FORM OF STRONTIUM RANELATE, METHOD FOR PRODUCING THE SAME AND MEDICINAL COMPOSITION CONTAINING THE SAME |
JP2010132669A (en) * | 2004-09-30 | 2010-06-17 | Lab Servier | STRONTIUM RANELATE ALPHA (alpha)-CRYSTALLINE FORM, METHOD OF PRODUCING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME |
JP2006273718A (en) * | 2005-03-28 | 2006-10-12 | Shiono Chemical Co Ltd | Method for producing levofloxacin-1/2 hydrate |
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 |
CN102146087A (en) * | 2010-02-10 | 2011-08-10 | 广东东阳光药业有限公司 | Method for preparing high-purity levofloxacin semihydrate |
US11065237B2 (en) | 2013-11-15 | 2021-07-20 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
US11690836B2 (en) | 2013-11-15 | 2023-07-04 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
Also Published As
Publication number | Publication date |
---|---|
CA2462023A1 (en) | 2003-04-10 |
ES2272781T3 (en) | 2007-05-01 |
JP2008273956A (en) | 2008-11-13 |
EP1451194A2 (en) | 2004-09-01 |
JP2007169288A (en) | 2007-07-05 |
AU2002341990A1 (en) | 2003-04-14 |
JP2006265261A (en) | 2006-10-05 |
EP1451194B1 (en) | 2006-10-04 |
AU2002341991A1 (en) | 2003-04-14 |
IL161164A0 (en) | 2004-08-31 |
DE60215213T2 (en) | 2007-08-30 |
DE60215213T3 (en) | 2010-07-01 |
JP2005504818A (en) | 2005-02-17 |
EP1772457A2 (en) | 2007-04-11 |
US20030130507A1 (en) | 2003-07-10 |
EP1451194B2 (en) | 2009-12-16 |
WO2003028665A3 (en) | 2003-11-20 |
US7629458B2 (en) | 2009-12-08 |
EP1451194A4 (en) | 2005-06-22 |
DE60215213D1 (en) | 2006-11-16 |
JP2007131628A (en) | 2007-05-31 |
EP1772457A3 (en) | 2007-07-04 |
ES2272781T5 (en) | 2010-04-06 |
US20050222409A1 (en) | 2005-10-06 |
ATE341553T1 (en) | 2006-10-15 |
WO2003028664A3 (en) | 2003-11-20 |
PT1451194E (en) | 2007-01-31 |
WO2003028665A2 (en) | 2003-04-10 |
EP1992629A1 (en) | 2008-11-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20050222409A1 (en) | Preparation of levofloxacin and forms thereof | |
WO2007010555A2 (en) | Novel crystalline forms of moxifloxacin hydrochloride and process for preparation thereof | |
EP1837331A2 (en) | New crystalline aripiprazole salts and processes for preparation and purification thereof | |
BRPI0514351A2 (en) | 4 - [[(7r) -8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-4-6-oxo-2-pteridinyl] amino] -3-methoxy hydrates and polymorphs -n- (1-methyl-4-piperidinyl) -b enzamide, processes for its preparation and use as a medicine | |
US20190002444A1 (en) | Crystalline forms of vilazodone hydrochloride and vilazodone free base | |
JP2008007517A (en) | Method for purification of levofloxacin | |
US20050124629A1 (en) | Methods for the purification of levofloxacin | |
WO2002083688A1 (en) | 3,7-diazabicyclo [3.3.1] formulations as antiarhythmic compounds | |
CA2528100A1 (en) | Polymorphic forms of ziprasidone hcl and processes for their preparation | |
US10519150B2 (en) | Salts of morpholine derivative, crystal forms thereof, processes for producing the same, pharmaceutical compositions including the same, and use thereof | |
US20220009929A1 (en) | Polymorphic forms of ibrutinib | |
WO2015170340A2 (en) | Novel polymorphs of sitagliptin hydrochloride, processes for its preparation and pharmaceutical composition thereof | |
WO2012001357A1 (en) | Crystalline form of prulifloxacin and processes for its preparation | |
US20090030207A1 (en) | Polymorphs of Dolasetron base and process for preparation thereof | |
KR20040058336A (en) | Methods for the purification of levofloxacin | |
MX2008000279A (en) | Crystalline forms of macrolide compounds endowed with antiinflammatory activity | |
AU2002307584A1 (en) | 3,7-Diazabicyclo [3.3.1] formulations as antiarhythmic compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR LC LK LR LS LT LU LV MA MD MG MN MW MX MZ NO NZ OM PH PL PT RU SD SE SG SI SK SL TJ TM TN TR TZ UA UG US UZ VC VN YU ZA ZM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): GH GM KE LS MW MZ SD SL SZ UG ZM ZW AM AZ BY KG KZ RU TJ TM AT BE BG CH CY CZ DK EE ES FI FR GB GR IE IT LU MC PT SE SK TR BF BJ CF CG CI GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2462023 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 161164 Country of ref document: IL |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2003532000 Country of ref document: JP Ref document number: 842/DELNP/2004 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002776152 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 2002776152 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 2002776152 Country of ref document: EP |