CN110294775B - 一种磷酸肌酸钠的纯化方法 - Google Patents
一种磷酸肌酸钠的纯化方法 Download PDFInfo
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- CN110294775B CN110294775B CN201810244057.4A CN201810244057A CN110294775B CN 110294775 B CN110294775 B CN 110294775B CN 201810244057 A CN201810244057 A CN 201810244057A CN 110294775 B CN110294775 B CN 110294775B
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- Prior art keywords
- creatine phosphate
- phosphate sodium
- creatine
- sodium
- flow rate
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- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 title claims abstract description 200
- 239000011734 sodium Substances 0.000 title claims abstract description 95
- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 95
- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000000746 purification Methods 0.000 title claims abstract description 39
- 239000007788 liquid Substances 0.000 claims abstract description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 238000001728 nano-filtration Methods 0.000 claims abstract description 18
- 239000006228 supernatant Substances 0.000 claims abstract description 18
- 102000004190 Enzymes Human genes 0.000 claims abstract description 13
- 108090000790 Enzymes Proteins 0.000 claims abstract description 13
- 238000001035 drying Methods 0.000 claims abstract description 13
- 239000002244 precipitate Substances 0.000 claims abstract description 11
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 8
- 239000012609 strong anion exchange resin Substances 0.000 claims abstract description 8
- 239000012610 weak anion exchange resin Substances 0.000 claims abstract description 8
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000001376 precipitating effect Effects 0.000 claims abstract description 4
- 239000012467 final product Substances 0.000 claims abstract description 3
- 230000000149 penetrating effect Effects 0.000 claims abstract description 3
- 238000011068 loading method Methods 0.000 claims description 47
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims description 34
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 30
- 238000001914 filtration Methods 0.000 claims description 28
- 238000010828 elution Methods 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229960003624 creatine Drugs 0.000 claims description 17
- 239000006046 creatine Substances 0.000 claims description 17
- 239000012528 membrane Substances 0.000 claims description 15
- 239000011780 sodium chloride Substances 0.000 claims description 15
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 13
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 13
- 238000000108 ultra-filtration Methods 0.000 claims description 13
- 239000012535 impurity Substances 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 claims description 8
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 claims description 8
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 claims description 8
- 239000002158 endotoxin Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- RNTXMYSPASRLFT-UHFFFAOYSA-L disodium;2-[[n'-[hydroxy(oxido)phosphoryl]carbamimidoyl]-methylamino]acetate Chemical compound [Na+].[Na+].OC(=O)CN(C)C(N)=NP([O-])([O-])=O RNTXMYSPASRLFT-UHFFFAOYSA-L 0.000 claims description 6
- 229910001437 manganese ion Inorganic materials 0.000 claims description 6
- -1 ammonium ions Chemical class 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 4
- 102000004420 Creatine Kinase Human genes 0.000 claims description 4
- 108010042126 Creatine kinase Proteins 0.000 claims description 4
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910001424 calcium ion Inorganic materials 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229920002521 macromolecule Polymers 0.000 claims description 3
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical group NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 claims description 3
- 229910001414 potassium ion Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 230000001172 regenerating effect Effects 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 claims description 2
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 claims description 2
- 239000013049 sediment Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000012295 chemical reaction liquid Substances 0.000 abstract description 7
- 239000012466 permeate Substances 0.000 abstract description 6
- 239000000243 solution Substances 0.000 description 53
- 239000000523 sample Substances 0.000 description 48
- 238000005406 washing Methods 0.000 description 30
- 239000011347 resin Substances 0.000 description 29
- 229920005989 resin Polymers 0.000 description 29
- 239000013078 crystal Substances 0.000 description 21
- 238000005342 ion exchange Methods 0.000 description 18
- 239000000843 powder Substances 0.000 description 16
- 238000001514 detection method Methods 0.000 description 13
- 229910019142 PO4 Inorganic materials 0.000 description 12
- 239000010452 phosphate Substances 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000035515 penetration Effects 0.000 description 10
- 230000000694 effects Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000000502 dialysis Methods 0.000 description 5
- 230000002255 enzymatic effect Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012527 feed solution Substances 0.000 description 3
- 238000004255 ion exchange chromatography Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229910001412 inorganic anion Inorganic materials 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 229910001422 barium ion Inorganic materials 0.000 description 1
- 238000007675 cardiac surgery Methods 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012540 ion exchange chromatography resin Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/222—Amides of phosphoric acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
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Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101033237A (zh) * | 2007-03-30 | 2007-09-12 | 上海华拓医药科技发展股份有限公司 | 药用磷酸肌酸二钠盐六水合物及其制备方法 |
WO2007146085A2 (en) * | 2006-06-06 | 2007-12-21 | Xenoport, Inc. | Creatine phosphate prodrugs, compositions and uses thereof |
CN101492470A (zh) * | 2008-01-22 | 2009-07-29 | 上海慈瑞医药科技有限公司 | 磷酸肌酸二钠盐的合成方法 |
CN101812088A (zh) * | 2010-03-19 | 2010-08-25 | 海南美大制药有限公司 | 一种高纯度的磷酸肌酸钠化合物 |
CN102295658A (zh) * | 2011-06-02 | 2011-12-28 | 重庆莱美药业股份有限公司 | 一种磷酸肌酸二钠盐的精制方法 |
CN103014083A (zh) * | 2012-12-31 | 2013-04-03 | 湖南宝利士生物技术有限公司 | 一种磷酸肌酸钠的制备方法 |
CN103012472A (zh) * | 2012-12-10 | 2013-04-03 | 天津大学 | 一种磷酸肌酸钠的结晶制备方法 |
CN103242364A (zh) * | 2012-12-28 | 2013-08-14 | 开封明仁药业有限公司 | 磷酸肌酸钠的制备方法 |
CN105132489A (zh) * | 2015-10-16 | 2015-12-09 | 西南药业股份有限公司 | 磷酸肌酸钠的制备方法 |
CN105153222A (zh) * | 2015-10-16 | 2015-12-16 | 西南药业股份有限公司 | 磷酸肌酸钠的纯化方法 |
CN106279267A (zh) * | 2015-05-20 | 2017-01-04 | 重庆圣华曦药业股份有限公司 | 一种磷酸肌酸钠的纯化方法及其无菌粉的制备 |
CN106928288A (zh) * | 2017-03-21 | 2017-07-07 | 华北制药华胜有限公司 | 一种硫酸双氢链霉素的制备方法 |
-
2018
- 2018-03-23 CN CN201810244057.4A patent/CN110294775B/zh active Active
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007146085A2 (en) * | 2006-06-06 | 2007-12-21 | Xenoport, Inc. | Creatine phosphate prodrugs, compositions and uses thereof |
CN101033237A (zh) * | 2007-03-30 | 2007-09-12 | 上海华拓医药科技发展股份有限公司 | 药用磷酸肌酸二钠盐六水合物及其制备方法 |
CN101492470A (zh) * | 2008-01-22 | 2009-07-29 | 上海慈瑞医药科技有限公司 | 磷酸肌酸二钠盐的合成方法 |
CN101812088A (zh) * | 2010-03-19 | 2010-08-25 | 海南美大制药有限公司 | 一种高纯度的磷酸肌酸钠化合物 |
CN102295658A (zh) * | 2011-06-02 | 2011-12-28 | 重庆莱美药业股份有限公司 | 一种磷酸肌酸二钠盐的精制方法 |
CN103012472A (zh) * | 2012-12-10 | 2013-04-03 | 天津大学 | 一种磷酸肌酸钠的结晶制备方法 |
CN103242364A (zh) * | 2012-12-28 | 2013-08-14 | 开封明仁药业有限公司 | 磷酸肌酸钠的制备方法 |
CN103014083A (zh) * | 2012-12-31 | 2013-04-03 | 湖南宝利士生物技术有限公司 | 一种磷酸肌酸钠的制备方法 |
CN106279267A (zh) * | 2015-05-20 | 2017-01-04 | 重庆圣华曦药业股份有限公司 | 一种磷酸肌酸钠的纯化方法及其无菌粉的制备 |
CN105132489A (zh) * | 2015-10-16 | 2015-12-09 | 西南药业股份有限公司 | 磷酸肌酸钠的制备方法 |
CN105153222A (zh) * | 2015-10-16 | 2015-12-16 | 西南药业股份有限公司 | 磷酸肌酸钠的纯化方法 |
CN106928288A (zh) * | 2017-03-21 | 2017-07-07 | 华北制药华胜有限公司 | 一种硫酸双氢链霉素的制备方法 |
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