CN102731584A - 一种单唾液酸四己糖神经节苷脂的制备方法 - Google Patents
一种单唾液酸四己糖神经节苷脂的制备方法 Download PDFInfo
- Publication number
- CN102731584A CN102731584A CN2012100760424A CN201210076042A CN102731584A CN 102731584 A CN102731584 A CN 102731584A CN 2012100760424 A CN2012100760424 A CN 2012100760424A CN 201210076042 A CN201210076042 A CN 201210076042A CN 102731584 A CN102731584 A CN 102731584A
- Authority
- CN
- China
- Prior art keywords
- monostalotetrahexosylgangliside
- preparation
- extraction
- sialo
- liquid
- 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
- 238000002360 preparation method Methods 0.000 title claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 95
- 238000000605 extraction Methods 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 40
- 210000004556 brain Anatomy 0.000 claims abstract description 33
- 239000000843 powder Substances 0.000 claims abstract description 13
- 238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 239000007788 liquid Substances 0.000 claims description 49
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 38
- 150000003408 sphingolipids Chemical class 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 238000007127 saponification reaction Methods 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 238000001556 precipitation Methods 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 229920005989 resin Polymers 0.000 claims description 18
- 238000013016 damping Methods 0.000 claims description 13
- 238000000151 deposition Methods 0.000 claims description 13
- 230000008021 deposition Effects 0.000 claims description 13
- 239000012530 fluid Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 238000010898 silica gel chromatography Methods 0.000 claims description 8
- 239000002893 slag Substances 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 125000005630 sialyl group Chemical group 0.000 claims description 7
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000004809 thin layer chromatography Methods 0.000 claims description 3
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 11
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 150000002270 gangliosides Chemical class 0.000 abstract description 4
- 239000000284 extract Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 239000013558 reference substance Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229960001866 silicon dioxide Drugs 0.000 description 8
- 239000006228 supernatant Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 6
- 230000008676 import Effects 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 210000005013 brain tissue Anatomy 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical class O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002271 DEAE-Sepharose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 102000005348 Neuraminidase Human genes 0.000 description 1
- 108010006232 Neuraminidase Proteins 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000012614 Q-Sepharose Substances 0.000 description 1
- 241000364021 Tulsa Species 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002156 adsorbate Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000001549 ceramide group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000004069 differentiation 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
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000010571 fourier transform-infrared absorption spectrum Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- -1 sulfuric acid ester Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Landscapes
- Medicines Containing Plant Substances (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210076042.4A CN102731584B (zh) | 2012-03-21 | 2012-03-21 | 一种单唾液酸四己糖神经节苷脂的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210076042.4A CN102731584B (zh) | 2012-03-21 | 2012-03-21 | 一种单唾液酸四己糖神经节苷脂的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102731584A true CN102731584A (zh) | 2012-10-17 |
CN102731584B CN102731584B (zh) | 2015-04-22 |
Family
ID=46987958
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201210076042.4A Active CN102731584B (zh) | 2012-03-21 | 2012-03-21 | 一种单唾液酸四己糖神经节苷脂的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102731584B (zh) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104151372A (zh) * | 2014-07-30 | 2014-11-19 | 湖南利诺生物药业有限公司 | 单唾液酸四已糖神经节苷脂钠gm1原料的制备方法 |
CN106905387A (zh) * | 2017-03-20 | 2017-06-30 | 泸州瑞兴生物工程有限公司 | 一种单唾液酸四己糖神经节苷脂钠的制备方法 |
CN108546276A (zh) * | 2018-05-23 | 2018-09-18 | 海南益尔生物制药有限公司 | 一种快速高效制备高纯度神经节苷脂的方法 |
CN108822164A (zh) * | 2018-05-23 | 2018-11-16 | 海南益尔生物制药有限公司 | 高质量单唾液酸四己糖神经节苷脂钠的制备工艺 |
CN109651458A (zh) * | 2019-01-31 | 2019-04-19 | 定安益尔生物技术有限公司 | 高效水解转化制备神经节苷脂的方法 |
CN109705176A (zh) * | 2019-01-23 | 2019-05-03 | 苏州纳微科技股份有限公司 | 一种猪神经节苷脂的分离纯化方法 |
CN109725068A (zh) * | 2017-10-27 | 2019-05-07 | 齐鲁制药有限公司 | 高效测定神经节苷脂gm1及其杂质的药物分析方法 |
CN110592164A (zh) * | 2019-09-23 | 2019-12-20 | 东北师范大学 | 一种单唾液酸四己糖神经节苷脂的制备方法 |
CN111499671A (zh) * | 2020-04-14 | 2020-08-07 | 内蒙古自治区中医药研究所 | 羊脑中几种不同类型神经节苷脂的提取制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1400216A (zh) * | 2001-07-26 | 2003-03-05 | 上海绿谷伟业生态工程有限公司 | 一种从动物组织中提取神经节苷脂的方法 |
CN101108868A (zh) * | 2007-07-12 | 2008-01-23 | 四川阳光博睿生物技术有限公司 | 制备高纯度单唾液酸四己糖神经节苷脂的方法 |
-
2012
- 2012-03-21 CN CN201210076042.4A patent/CN102731584B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1400216A (zh) * | 2001-07-26 | 2003-03-05 | 上海绿谷伟业生态工程有限公司 | 一种从动物组织中提取神经节苷脂的方法 |
CN101108868A (zh) * | 2007-07-12 | 2008-01-23 | 四川阳光博睿生物技术有限公司 | 制备高纯度单唾液酸四己糖神经节苷脂的方法 |
Non-Patent Citations (1)
Title |
---|
TOMOMI SUMIDA ET AL: "Utilization of Ganglioside-Degrading Paenibacillus sp. Strain TS12 for Production of Glucosylceramide", 《APPLIED AND ENVIRONMENTAL MICROBIOLOGY》 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104151372A (zh) * | 2014-07-30 | 2014-11-19 | 湖南利诺生物药业有限公司 | 单唾液酸四已糖神经节苷脂钠gm1原料的制备方法 |
CN106905387A (zh) * | 2017-03-20 | 2017-06-30 | 泸州瑞兴生物工程有限公司 | 一种单唾液酸四己糖神经节苷脂钠的制备方法 |
CN109725068A (zh) * | 2017-10-27 | 2019-05-07 | 齐鲁制药有限公司 | 高效测定神经节苷脂gm1及其杂质的药物分析方法 |
CN108546276A (zh) * | 2018-05-23 | 2018-09-18 | 海南益尔生物制药有限公司 | 一种快速高效制备高纯度神经节苷脂的方法 |
CN108822164A (zh) * | 2018-05-23 | 2018-11-16 | 海南益尔生物制药有限公司 | 高质量单唾液酸四己糖神经节苷脂钠的制备工艺 |
CN109705176A (zh) * | 2019-01-23 | 2019-05-03 | 苏州纳微科技股份有限公司 | 一种猪神经节苷脂的分离纯化方法 |
CN109651458A (zh) * | 2019-01-31 | 2019-04-19 | 定安益尔生物技术有限公司 | 高效水解转化制备神经节苷脂的方法 |
CN110592164A (zh) * | 2019-09-23 | 2019-12-20 | 东北师范大学 | 一种单唾液酸四己糖神经节苷脂的制备方法 |
CN111499671A (zh) * | 2020-04-14 | 2020-08-07 | 内蒙古自治区中医药研究所 | 羊脑中几种不同类型神经节苷脂的提取制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN102731584B (zh) | 2015-04-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102731584B (zh) | 一种单唾液酸四己糖神经节苷脂的制备方法 | |
CN101108868B (zh) | 制备高纯度单唾液酸四己糖神经节苷脂的方法 | |
CN101508715A (zh) | 一种蛹虫草中虫草素提取纯化方法 | |
CN108864217B (zh) | 一种石榴皮安石榴苷的纯化方法 | |
CN108689852A (zh) | 一种从平卧菊三七中提取绿原酸和异绿原酸的方法 | |
CN105334301B (zh) | 一种吡咯并喹啉醌pqq二钠盐杂质的分离纯化方法 | |
CN108553556A (zh) | 一种从西红花中制备西红花总苷的方法 | |
CN113201081A (zh) | 具免疫活性的平卧菊三七多糖及其制备方法和应用 | |
CN114591448A (zh) | 一种桑树桑黄子实体甘露半乳聚糖及其制备和用途 | |
CN100453550C (zh) | 人参皂苷Rb2的制备工艺 | |
CN102260286B (zh) | 一种分离纯化粗产品L-α-甘油磷酸胆碱的方法 | |
Manikowski et al. | An alternative route for fondaparinux sodium synthesis via selective hydrogenations and sulfation of appropriate pentasaccharides | |
CN109942663B (zh) | 利用双相酸水解制备环黄芪醇的方法 | |
CN102093453B (zh) | 20(R)-25-羟基-达玛烷型-3β,12β,20-三醇的制备方法 | |
CN111747881A (zh) | 两种具有α-葡萄糖苷酶抑制作用的异戊烯基取代吲哚生物碱及其制备方法和应用 | |
CN108558621B (zh) | 一种柠檬醛二冰片基缩醛衍生物及其制备方法与用途 | |
CN103788232A (zh) | 一种硫酸乙酰肝素十糖及其制备方法和应用 | |
CN108042618B (zh) | 一种利用亚临界水提取芍药总苷的方法 | |
CN115677795A (zh) | 一种吡喃葡萄糖苷衍生物的提取方法 | |
CN110592164A (zh) | 一种单唾液酸四己糖神经节苷脂的制备方法 | |
CN102924629B (zh) | 依诺肝素钠化合物及其制备方法 | |
CN113511967B (zh) | 一种从银杏叶提取物层析废水中提取奎宁酸的方法 | |
CN102297905B (zh) | 用手性柱分离鉴定及制备葫芦素混合物中单体物质的hplc方法 | |
CN108059603B (zh) | 伏格列波糖杂质n-甲基井岗酶醇胺的精制工艺 | |
CN102260313B (zh) | 无定形态人参皂苷Rb1及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20151123 Address after: 646100 Lily Town, Luzhou, Sichuan, Luxian County Patentee after: Luzhou Ruixing Biological Engineering Co. Ltd. Address before: 646100 Lily Town, Luzhou, Sichuan, Luxian County Patentee before: Luzhou Ruixing Chemical Industry Co., Ltd. Patentee before: Chongqing Zihe Pharmaceutical Technology Development Co., Ltd. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of monosialoteterahexosylganglioside Effective date of registration: 20180828 Granted publication date: 20150422 Pledgee: Luzhou Xinglu finance Company limited by guarantee Pledgor: Luzhou Ruixing Biological Engineering Co. Ltd. Registration number: 2018510000087 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20190819 Granted publication date: 20150422 Pledgee: Luzhou Xinglu finance Company limited by guarantee Pledgor: Luzhou Ruixing Biological Engineering Co. Ltd. Registration number: 2018510000087 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of monosialoteterahexosylganglioside Effective date of registration: 20190827 Granted publication date: 20150422 Pledgee: Luzhou Xinglu Financing Guarantee Group Co., Ltd. Pledgor: Luzhou Ruixing Biological Engineering Co. Ltd. Registration number: Y2019510000013 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of monosialoteterahexosylganglioside Effective date of registration: 20190827 Granted publication date: 20150422 Pledgee: Luzhou Xinglu Financing Guarantee Group Co., Ltd. Pledgor: Luzhou Ruixing Biological Engineering Co. Ltd. Registration number: Y2019510000013 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20200903 Granted publication date: 20150422 Pledgee: Luzhou Xinglu Financing Guarantee Group Co.,Ltd. Pledgor: LUZHOU RUIXING BIOENGINEERING Co.,Ltd. Registration number: Y2019510000013 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20210407 Address after: 646100 Lingang Economic Park, Luxian Economic Development Zone, Luzhou City, Sichuan Province Patentee after: SICHUAN QIGEMAN PHARMACEUTICAL Co.,Ltd. Address before: 646100 Baihe Town, Luxian County, Luzhou City, Sichuan Province Patentee before: LUZHOU RUIXING BIOENGINEERING Co.,Ltd. |
|
TR01 | Transfer of patent right |