CN116768910B - 一种利福布汀的精制方法 - Google Patents
一种利福布汀的精制方法 Download PDFInfo
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- CN116768910B CN116768910B CN202311040148.3A CN202311040148A CN116768910B CN 116768910 B CN116768910 B CN 116768910B CN 202311040148 A CN202311040148 A CN 202311040148A CN 116768910 B CN116768910 B CN 116768910B
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- rifabutin
- organic solvent
- dissolving
- refining
- solution
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- ZWBTYMGEBZUQTK-PVLSIAFMSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c4NC5(CCN(CC(C)C)CC5)N=c4c(=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C ZWBTYMGEBZUQTK-PVLSIAFMSA-N 0.000 title claims abstract description 98
- 229960000885 rifabutin Drugs 0.000 title claims abstract description 98
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000007670 refining Methods 0.000 title claims abstract description 21
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000003960 organic solvent Substances 0.000 claims abstract description 24
- 239000012043 crude product Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 21
- 238000001914 filtration Methods 0.000 claims abstract description 20
- 239000008213 purified water Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 18
- 239000001384 succinic acid Substances 0.000 claims abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 13
- 239000013078 crystal Substances 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 238000001704 evaporation Methods 0.000 claims abstract description 6
- 239000012074 organic phase Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 238000001514 detection method Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical class OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 description 2
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical compound C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108020000946 Bacterial DNA Proteins 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
- 229930189077 Rifamycin Natural products 0.000 description 1
- BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 description 1
- BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960003292 rifamycin Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3914218A (en) * | 1974-01-09 | 1975-10-21 | Pfizer | 3-Methylthiorifamycins |
ES478428A2 (es) * | 1978-04-28 | 1979-05-16 | Archifar Lab Chim Farm | Mejoras introducidas en el objeto de la patente principal n.449.187:procedimiento para la preparacion de compuestos de rifamicina de elevada actividad antibiotica. |
PL290811A1 (en) * | 1991-06-26 | 1992-12-28 | Os Bad Rozwojowy Biotechnologi | Method of obtaining spiropiperidiloriphamycine antibiotics |
BG105672A (en) * | 2001-07-05 | 2003-01-31 | "Биовет" Ад | Method for rifabutin production |
CN101195628A (zh) * | 2006-12-05 | 2008-06-11 | 四川明欣药业有限责任公司 | 一种利福布汀结晶工艺 |
CN101253154A (zh) * | 2005-09-02 | 2008-08-27 | 百奥帝卡技术有限公司 | 新的安莎霉素衍生物 |
CN109400628A (zh) * | 2018-12-26 | 2019-03-01 | 重庆华邦胜凯制药有限公司 | 一种利福布汀中间体的制备方法 |
CN111018887A (zh) * | 2019-12-23 | 2020-04-17 | 成都锦华药业有限责任公司 | 一种纯化利福平的方法 |
-
2023
- 2023-08-18 CN CN202311040148.3A patent/CN116768910B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3914218A (en) * | 1974-01-09 | 1975-10-21 | Pfizer | 3-Methylthiorifamycins |
GB1478469A (en) * | 1974-01-09 | 1977-06-29 | Pfizer | Ansamycin antibiotics produced by a species of micromonospora |
ES478428A2 (es) * | 1978-04-28 | 1979-05-16 | Archifar Lab Chim Farm | Mejoras introducidas en el objeto de la patente principal n.449.187:procedimiento para la preparacion de compuestos de rifamicina de elevada actividad antibiotica. |
PL290811A1 (en) * | 1991-06-26 | 1992-12-28 | Os Bad Rozwojowy Biotechnologi | Method of obtaining spiropiperidiloriphamycine antibiotics |
BG105672A (en) * | 2001-07-05 | 2003-01-31 | "Биовет" Ад | Method for rifabutin production |
CN101253154A (zh) * | 2005-09-02 | 2008-08-27 | 百奥帝卡技术有限公司 | 新的安莎霉素衍生物 |
CN101195628A (zh) * | 2006-12-05 | 2008-06-11 | 四川明欣药业有限责任公司 | 一种利福布汀结晶工艺 |
CN109400628A (zh) * | 2018-12-26 | 2019-03-01 | 重庆华邦胜凯制药有限公司 | 一种利福布汀中间体的制备方法 |
CN111018887A (zh) * | 2019-12-23 | 2020-04-17 | 成都锦华药业有限责任公司 | 一种纯化利福平的方法 |
Non-Patent Citations (2)
Title |
---|
利福布丁中微量未知杂质的量与其HPLC峰面积线性关系的探讨;唐克慧, 王广芳, 王艾莉, 常宁, 王宇驰;中国抗生素杂志(第01期);第23-25页 * |
唐克慧,王广芳,王艾莉,常宁,王宇驰.利福布丁中微量未知杂质的量与其HPLC峰面积线性关系的探讨.中国抗生素杂志.2004,(第01期),第23-25页. * |
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Denomination of invention: A Refinement Method for Levofloxacin Effective date of registration: 20231206 Granted publication date: 20231031 Pledgee: Shandong Linzi Rural Commercial Bank Co.,Ltd. Pledgor: SHANDONG QIDU PHARMACEUTICAL Co.,Ltd. Registration number: Y2023980069709 |
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Granted publication date: 20231031 Pledgee: Shandong Linzi Rural Commercial Bank Co.,Ltd. Pledgor: SHANDONG QIDU PHARMACEUTICAL Co.,Ltd. Registration number: Y2023980069709 |
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