CN101565439B - 改进的泰乐菌素提炼方法 - Google Patents
改进的泰乐菌素提炼方法 Download PDFInfo
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- CN101565439B CN101565439B CN2008100937803A CN200810093780A CN101565439B CN 101565439 B CN101565439 B CN 101565439B CN 2008100937803 A CN2008100937803 A CN 2008100937803A CN 200810093780 A CN200810093780 A CN 200810093780A CN 101565439 B CN101565439 B CN 101565439B
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- extraction
- water
- tylosin
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- Expired - Fee Related
Links
- 229930194936 Tylosin Natural products 0.000 title claims abstract description 124
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 title claims abstract description 124
- 235000019375 tylosin Nutrition 0.000 title claims abstract description 124
- 239000004182 Tylosin Substances 0.000 title claims abstract description 123
- 229960004059 tylosin Drugs 0.000 title claims abstract description 123
- 238000000605 extraction Methods 0.000 title abstract description 175
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 96
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 92
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 56
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000006184 cosolvent Substances 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 21
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims abstract description 9
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960001701 chloroform Drugs 0.000 claims description 92
- 229940043232 butyl acetate Drugs 0.000 claims description 55
- 239000000706 filtrate Substances 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 abstract description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 26
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 abstract description 7
- 238000000855 fermentation Methods 0.000 abstract description 6
- 230000004151 fermentation Effects 0.000 abstract description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 3
- 229940117955 isoamyl acetate Drugs 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 235000019439 ethyl acetate Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000012071 phase Substances 0.000 description 29
- 239000000284 extract Substances 0.000 description 23
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 20
- 229940095064 tartrate Drugs 0.000 description 19
- 238000004821 distillation Methods 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 238000012546 transfer Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 230000018044 dehydration Effects 0.000 description 15
- 238000006297 dehydration reaction Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- ICVKYYINQHWDLM-KBEWXLTPSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;2-[(4r,5s,6s,7r,9r,11e,13e,15r,16r)-6-[(2r,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4 Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 ICVKYYINQHWDLM-KBEWXLTPSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 229960001717 tylosin tartrate Drugs 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YEJCDKJIEMIWRQ-UHFFFAOYSA-N Linopirdine Chemical compound O=C1N(C=2C=CC=CC=2)C2=CC=CC=C2C1(CC=1C=CN=CC=1)CC1=CC=NC=C1 YEJCDKJIEMIWRQ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- -1 phosphoric acid salt Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000187438 Streptomyces fradiae Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical class [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN2008100937803A CN101565439B (zh) | 2008-04-21 | 2008-04-21 | 改进的泰乐菌素提炼方法 |
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CN2008100937803A CN101565439B (zh) | 2008-04-21 | 2008-04-21 | 改进的泰乐菌素提炼方法 |
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CN101565439A CN101565439A (zh) | 2009-10-28 |
CN101565439B true CN101565439B (zh) | 2012-03-21 |
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CN2008100937803A Expired - Fee Related CN101565439B (zh) | 2008-04-21 | 2008-04-21 | 改进的泰乐菌素提炼方法 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102746354A (zh) * | 2012-07-17 | 2012-10-24 | 宁夏泰瑞制药股份有限公司 | 一种利用泰乐菌素发酵液提取泰乐碱的方法 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102584921B (zh) * | 2012-01-20 | 2014-08-06 | 宁夏泰瑞制药股份有限公司 | 一种泰乐菌素提取溶媒及提取方法 |
CN102584920A (zh) * | 2012-01-20 | 2012-07-18 | 宁夏泰瑞制药股份有限公司 | 弗氏链霉菌发酵生产泰乐菌素的培养基及发酵方法 |
CN102659878B (zh) * | 2012-04-11 | 2013-12-04 | 宁夏泰瑞制药股份有限公司 | 一种利用泰乐菌素发酵液合成替米考星及磷酸替米考星的方法 |
CN103709218B (zh) * | 2013-05-22 | 2016-02-10 | 浙江普洛康裕生物制药有限公司 | 一种提高泰乐菌素a组分的提取方法 |
CN104926899A (zh) * | 2015-05-11 | 2015-09-23 | 成都中牧生物药业有限公司 | 避免降低酒石酸泰乐菌素原药药性的制备工艺 |
CN104892705A (zh) * | 2015-05-11 | 2015-09-09 | 成都中牧生物药业有限公司 | 注射用酒石酸泰乐菌素的制备工艺 |
CN109535212A (zh) * | 2018-12-27 | 2019-03-29 | 宁夏泰益欣生物科技有限公司 | 一种泰乐菌素的制备方法 |
CN115403643A (zh) * | 2021-05-28 | 2022-11-29 | 宁夏泰益欣生物科技有限公司 | 一种泰乐菌素的提纯方法 |
-
2008
- 2008-04-21 CN CN2008100937803A patent/CN101565439B/zh not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102746354A (zh) * | 2012-07-17 | 2012-10-24 | 宁夏泰瑞制药股份有限公司 | 一种利用泰乐菌素发酵液提取泰乐碱的方法 |
CN102746354B (zh) * | 2012-07-17 | 2014-09-10 | 宁夏泰瑞制药股份有限公司 | 一种利用泰乐菌素发酵液提取泰乐碱的方法 |
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CN101565439A (zh) | 2009-10-28 |
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Owner name: HERB (BEIJING) PHARMACEUTICAL COMPANY Free format text: FORMER OWNER: WANG YUWAN Effective date: 20131120 |
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Effective date of registration: 20131120 Address after: 102206 Wang Zhuang Industrial Zone, Shahe Airport Road, Changping District, Beijing Patentee after: Hogben (Beijing) Pharmaceutical Co.,Ltd. Address before: 100089 Beijing box 8956 Haidian District Wanliu spring Sinorama District Building 5 room 103 Patentee before: Wang Yuwan |
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