CN106083883A - 一种米尔贝霉素肟粗品的纯化方法 - Google Patents
一种米尔贝霉素肟粗品的纯化方法 Download PDFInfo
- Publication number
- CN106083883A CN106083883A CN201610504593.4A CN201610504593A CN106083883A CN 106083883 A CN106083883 A CN 106083883A CN 201610504593 A CN201610504593 A CN 201610504593A CN 106083883 A CN106083883 A CN 106083883A
- Authority
- CN
- China
- Prior art keywords
- mibemycin
- crude product
- oxime
- purified water
- mibemycin oxime
- 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.)
- Granted
Links
- 150000002923 oximes Chemical class 0.000 title claims abstract description 120
- 239000012043 crude product Substances 0.000 title claims abstract description 34
- 238000000746 purification Methods 0.000 title claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 61
- 239000000047 product Substances 0.000 claims abstract description 30
- 238000001914 filtration Methods 0.000 claims abstract description 21
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 16
- 238000005516 engineering process Methods 0.000 claims abstract description 15
- 238000002425 crystallisation Methods 0.000 claims abstract description 13
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 12
- 230000008025 crystallization Effects 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000013517 stratification Methods 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 6
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims abstract description 5
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims abstract description 5
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000012545 processing Methods 0.000 claims abstract description 3
- 239000008213 purified water Substances 0.000 claims description 52
- 238000003756 stirring Methods 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 238000007599 discharging Methods 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 4
- 229920001429 chelating resin Polymers 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 239000010865 sewage Substances 0.000 claims description 2
- -1 isobutyl ester Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 8
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000005728 strengthening Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 235000015170 shellfish Nutrition 0.000 description 10
- 238000012360 testing method Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CKVMAPHTVCTEMM-ALPQRHTBSA-N milbemycin oxime Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\2)O)C[C@H]4C1.C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\1)O)C[C@H]4C2 CKVMAPHTVCTEMM-ALPQRHTBSA-N 0.000 description 3
- 229940099245 milbemycin oxime Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 208000003917 Dirofilariasis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001655322 Streptomycetales Species 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 208000010717 cat disease Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 238000012503 pharmacopoeial method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 208000009920 trichuriasis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (11)
Priority Applications (1)
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CN201610504593.4A CN106083883B (zh) | 2016-07-01 | 2016-07-01 | 一种米尔贝霉素肟粗品的纯化方法 |
Applications Claiming Priority (1)
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---|---|---|---|
CN201610504593.4A CN106083883B (zh) | 2016-07-01 | 2016-07-01 | 一种米尔贝霉素肟粗品的纯化方法 |
Publications (2)
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CN106083883A true CN106083883A (zh) | 2016-11-09 |
CN106083883B CN106083883B (zh) | 2017-12-26 |
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CN201610504593.4A Active CN106083883B (zh) | 2016-07-01 | 2016-07-01 | 一种米尔贝霉素肟粗品的纯化方法 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000281683A (ja) * | 1999-03-29 | 2000-10-10 | Sankyo Co Ltd | ミルベマイシン類及びアベルメクチン類の精製法 |
CN104497003A (zh) * | 2014-11-27 | 2015-04-08 | 北大医药重庆大新药业股份有限公司 | 一种高纯度米尔贝霉素的制备方法 |
CN105061457A (zh) * | 2015-08-20 | 2015-11-18 | 湖北宏中药业股份有限公司 | 一种米尔贝肟的合成方法 |
CN105440049A (zh) * | 2014-08-27 | 2016-03-30 | 北大医药重庆大新药业股份有限公司 | 一种制备高纯度米尔贝肟的方法 |
-
2016
- 2016-07-01 CN CN201610504593.4A patent/CN106083883B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000281683A (ja) * | 1999-03-29 | 2000-10-10 | Sankyo Co Ltd | ミルベマイシン類及びアベルメクチン類の精製法 |
CN105440049A (zh) * | 2014-08-27 | 2016-03-30 | 北大医药重庆大新药业股份有限公司 | 一种制备高纯度米尔贝肟的方法 |
CN104497003A (zh) * | 2014-11-27 | 2015-04-08 | 北大医药重庆大新药业股份有限公司 | 一种高纯度米尔贝霉素的制备方法 |
CN105061457A (zh) * | 2015-08-20 | 2015-11-18 | 湖北宏中药业股份有限公司 | 一种米尔贝肟的合成方法 |
Non-Patent Citations (3)
Title |
---|
HAI-YANWANG ET AL.: ""Combined application of plasma mutagenesis and gene engineering leads to 5-oxomilbemycins A3/A4 as main components from Streptomyces bingchenggensis"", 《APPL MICROBIOL BIOTECHNOL》 * |
YOSHIHISA TSUKAMOTO ET AL.: ""Synthesis of 5-Keto-5-oxime Derivatives of Milbemycins Their Activities against Microfilariae"", 《AGRIC.BIOL.CHEM.》 * |
谢捷 等: ""大孔树脂分离纯化米尔贝霉素工艺研究"", 《浙江工业大学学报》 * |
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Publication number | Publication date |
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CN106083883B (zh) | 2017-12-26 |
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Effective date of registration: 20240520 Address after: 750411 West side of Qihe Road and south side of Qiyuan Road in Ningdong Base New Materials Park, Yinchuan City, Ningxia Hui Autonomous Region Patentee after: Ningxia Taisheng Biotechnology Co.,Ltd. Country or region after: China Address before: 750101 Wangyuan Industrial Park, Yongning County, Yinchuan City, Ningxia Hui Autonomous Region Patentee before: NINGXIA TAIRUI PHARMACEUTICAL Co.,Ltd. Country or region before: China |
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