CN102746320A - 盐酸左氧氟沙星的晶型及其制备方法 - Google Patents
盐酸左氧氟沙星的晶型及其制备方法 Download PDFInfo
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- CN102746320A CN102746320A CN201110099303XA CN201110099303A CN102746320A CN 102746320 A CN102746320 A CN 102746320A CN 201110099303X A CN201110099303X A CN 201110099303XA CN 201110099303 A CN201110099303 A CN 201110099303A CN 102746320 A CN102746320 A CN 102746320A
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- CN
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- Prior art keywords
- levofloxacin hydrochloride
- crystal
- water
- crystal form
- solvent
- 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.)
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- 239000013078 crystal Substances 0.000 title claims abstract description 110
- CAOOISJXWZMLBN-PPHPATTJSA-N htn0d03vrz Chemical compound Cl.C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 CAOOISJXWZMLBN-PPHPATTJSA-N 0.000 title claims abstract description 83
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
- 230000015572 biosynthetic process Effects 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 238000002425 crystallisation Methods 0.000 claims description 24
- 230000008025 crystallization Effects 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 17
- 238000000967 suction filtration Methods 0.000 claims description 15
- 238000012512 characterization method Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000012046 mixed solvent Substances 0.000 claims description 9
- 230000003595 spectral effect Effects 0.000 claims description 9
- 238000001228 spectrum Methods 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 4
- 238000002050 diffraction method Methods 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 3
- 230000007774 longterm Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 description 29
- 238000005303 weighing Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 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 description 10
- 229960003376 levofloxacin Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 7
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 238000002834 transmittance Methods 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
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229960001699 ofloxacin Drugs 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 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 1
- FCYFNNCOWAGAGQ-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid;hydrochloride Chemical group Cl.O1NC=CC2=CC(C(=O)O)=CC=C21 FCYFNNCOWAGAGQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110099303.XA CN102746320B (zh) | 2011-04-20 | 2011-04-20 | 盐酸左氧氟沙星的晶型及其制备方法 |
Applications Claiming Priority (1)
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CN201110099303.XA CN102746320B (zh) | 2011-04-20 | 2011-04-20 | 盐酸左氧氟沙星的晶型及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN102746320A true CN102746320A (zh) | 2012-10-24 |
CN102746320B CN102746320B (zh) | 2015-04-22 |
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CN201110099303.XA Active CN102746320B (zh) | 2011-04-20 | 2011-04-20 | 盐酸左氧氟沙星的晶型及其制备方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106674250A (zh) * | 2016-12-27 | 2017-05-17 | 河南康达制药有限公司 | 一种盐酸左氧氟沙星的制备方法 |
CN107522717A (zh) * | 2016-06-20 | 2017-12-29 | 珠海同源药业有限公司 | 一种盐酸左氧氟沙星晶体及其组合物 |
CN112279866A (zh) * | 2020-11-24 | 2021-01-29 | 辽宁药联制药有限公司 | 一种盐酸左氧氟沙星多晶型物及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2006048889A1 (en) * | 2004-11-08 | 2006-05-11 | Neuland Laboratories Ltd. | An improved process for the preparation of levofloxacin hemihydrate |
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 |
CN101863904A (zh) * | 2010-07-08 | 2010-10-20 | 浙江东亚药业有限公司 | 一种高纯度左氧氟沙星半水合物的制备方法 |
-
2011
- 2011-04-20 CN CN201110099303.XA patent/CN102746320B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2006048889A1 (en) * | 2004-11-08 | 2006-05-11 | Neuland Laboratories Ltd. | An improved process for the preparation of levofloxacin hemihydrate |
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 |
CN101863904A (zh) * | 2010-07-08 | 2010-10-20 | 浙江东亚药业有限公司 | 一种高纯度左氧氟沙星半水合物的制备方法 |
Non-Patent Citations (1)
Title |
---|
张薇,等: "喹诺酮类抗菌药物研究进展", 《西北药学杂志》, vol. 22, no. 3, 30 June 2007 (2007-06-30), pages 157 - 158 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107522717A (zh) * | 2016-06-20 | 2017-12-29 | 珠海同源药业有限公司 | 一种盐酸左氧氟沙星晶体及其组合物 |
CN106674250A (zh) * | 2016-12-27 | 2017-05-17 | 河南康达制药有限公司 | 一种盐酸左氧氟沙星的制备方法 |
CN112279866A (zh) * | 2020-11-24 | 2021-01-29 | 辽宁药联制药有限公司 | 一种盐酸左氧氟沙星多晶型物及其制备方法 |
Also Published As
Publication number | Publication date |
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CN102746320B (zh) | 2015-04-22 |
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Address after: 31 Weisan Road, Shangyu Economic and Technological Development Zone, Hangzhou Bay, Shangyu City, Shaoxing City, Zhejiang Province, China, 312369 Patentee after: Shaoxing Jingxin Pharmaceutical Co.,Ltd. Address before: 31 Weisan Road, Shangyu Industrial Park, Hangzhou Bay, Shaoxing City, Zhejiang Province, China Patentee before: SHANGYU JINGXIN PHARMACEUTICAL Co.,Ltd. |
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CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: 312369 No.31, Weisan Road, Shangyu economic and Technological Development Zone, Hangzhou Bay, Shaoxing City, Zhejiang Province Patentee after: Shaoxing Jingxin Pharmaceutical Co.,Ltd. Country or region after: China Address before: 31 Weisan Road, Shangyu Economic and Technological Development Zone, Hangzhou Bay, Shangyu City, Shaoxing City, Zhejiang Province, China, 312369 Patentee before: Shaoxing Jingxin Pharmaceutical Co.,Ltd. Country or region before: China |
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CP03 | Change of name, title or address |