KR20140091739A - 테이코플라닌의 정제 방법 - Google Patents
테이코플라닌의 정제 방법 Download PDFInfo
- Publication number
- KR20140091739A KR20140091739A KR1020147015313A KR20147015313A KR20140091739A KR 20140091739 A KR20140091739 A KR 20140091739A KR 1020147015313 A KR1020147015313 A KR 1020147015313A KR 20147015313 A KR20147015313 A KR 20147015313A KR 20140091739 A KR20140091739 A KR 20140091739A
- Authority
- KR
- South Korea
- Prior art keywords
- teicoplanin
- solution
- resin
- water
- ultrafiltration
- 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.)
- Ceased
Links
- 108010053950 Teicoplanin Proteins 0.000 title claims abstract description 175
- DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 title claims abstract description 174
- 229960001608 teicoplanin Drugs 0.000 title claims abstract description 174
- 238000000034 method Methods 0.000 title claims abstract description 96
- 230000008569 process Effects 0.000 title claims abstract description 30
- 238000000746 purification Methods 0.000 title abstract description 17
- 229920005989 resin Polymers 0.000 claims abstract description 112
- 239000011347 resin Substances 0.000 claims abstract description 112
- 239000000243 solution Substances 0.000 claims abstract description 91
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 50
- 239000003960 organic solvent Substances 0.000 claims abstract description 48
- 239000003463 adsorbent Substances 0.000 claims abstract description 46
- 238000001179 sorption measurement Methods 0.000 claims abstract description 39
- 239000003610 charcoal Substances 0.000 claims abstract description 28
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 28
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 192
- 229920001429 chelating resin Polymers 0.000 claims description 61
- 239000012528 membrane Substances 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 26
- 239000011148 porous material Substances 0.000 claims description 21
- 230000002378 acidificating effect Effects 0.000 claims description 20
- 239000002609 medium Substances 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 13
- 239000012736 aqueous medium Substances 0.000 claims description 11
- 239000000872 buffer Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- 238000011033 desalting Methods 0.000 claims description 6
- 238000005119 centrifugation Methods 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 229920005553 polystyrene-acrylate Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000007738 vacuum evaporation Methods 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000001694 spray drying Methods 0.000 claims description 3
- 241000187842 Actinoplanes teichomyceticus Species 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 239000012535 impurity Substances 0.000 abstract description 64
- 239000000203 mixture Substances 0.000 abstract description 38
- 238000010828 elution Methods 0.000 abstract description 19
- 239000000706 filtrate Substances 0.000 abstract description 19
- 238000000855 fermentation Methods 0.000 abstract description 17
- 230000004151 fermentation Effects 0.000 abstract description 17
- 239000000047 product Substances 0.000 abstract description 12
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
- 239000012466 permeate Substances 0.000 description 21
- 238000003795 desorption Methods 0.000 description 20
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 17
- 238000002955 isolation Methods 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 230000001590 oxidative effect Effects 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000012488 sample solution Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 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 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000011026 diafiltration Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- LCTCUBQFWLTHNS-MDZDMXLPSA-N 61036-64-4 Chemical compound CCCCC\C=C\CCC(=O)NC1C(O)C(O)C(CO)OC1OC(C(=C1)OC=2C(=CC(=CC=2)C(OC2C(C(O)C(O)C(CO)O2)NC(C)=O)C2C(NC(C3=CC(O)=CC(OC4C(C(O)C(O)C(CO)O4)O)=C3C=3C(O)=CC=C(C=3)C(NC3=O)C(=O)N2)C(=O)OC)=O)Cl)=C(OC=2C(=CC(=CC=2)C(O)C(C(N2)=O)NC(=O)C(N)C=4C=C(O5)C(O)=CC=4)Cl)C=C1C3NC(=O)C2C1=CC(O)=C(C)C5=C1 LCTCUBQFWLTHNS-MDZDMXLPSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012296 anti-solvent Substances 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000006240 deamidation Effects 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- -1 for example Chemical compound 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 2
- 229910001853 inorganic hydroxide Inorganic materials 0.000 description 2
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 238000001728 nano-filtration Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- 230000001698 pyrogenic effect Effects 0.000 description 2
- 239000012465 retentate Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- BJNLLBUOHPVGFT-CAYRISATSA-N (1S,2R,19R,22R,34S,37R,40R,52S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-amino-5,15-dichloro-64-[(2S,3R,4R,5S,6R)-3-(decanoylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid Chemical compound CCCCCCCCCC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1Oc1c2Oc3ccc(C[C@H]4NC(=O)[C@H](N)c5ccc(O)c(Oc6cc(O)cc(c6)[C@H](NC4=O)C(=O)N[C@@H]4c(c2)cc1Oc1ccc(cc1Cl)[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O)[C@@H]1NC(=O)[C@H](NC4=O)c2ccc(O)c(c2)-c2c(OC4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)cc(O)cc2[C@H](NC1=O)C(O)=O)c5)cc3Cl BJNLLBUOHPVGFT-CAYRISATSA-N 0.000 description 1
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 1
- QPILHXCDZYWYLQ-UHFFFAOYSA-N 2-nonyl-1,3-dioxolane Chemical compound CCCCCCCCCC1OCCO1 QPILHXCDZYWYLQ-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010015899 Glycopeptides Proteins 0.000 description 1
- 102000002068 Glycopeptides Human genes 0.000 description 1
- 101000851593 Homo sapiens Separin Proteins 0.000 description 1
- 108010081391 Ristocetin Proteins 0.000 description 1
- 102100036750 Separin Human genes 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 241000985696 Tecoma Species 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002547 anomalous effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011284 combination treatment 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
- 238000009295 crossflow filtration Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 125000003473 lipid group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229950004257 ristocetin Drugs 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000005549 size reduction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940049565 targocid Drugs 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11188759.2 | 2011-11-11 | ||
| EP11188759.2A EP2592089A1 (en) | 2011-11-11 | 2011-11-11 | Process of purification of teicoplanin |
| PCT/EP2012/072279 WO2013068538A1 (en) | 2011-11-11 | 2012-11-09 | Process of purification of teicoplanin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140091739A true KR20140091739A (ko) | 2014-07-22 |
Family
ID=47148819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147015313A Ceased KR20140091739A (ko) | 2011-11-11 | 2012-11-09 | 테이코플라닌의 정제 방법 |
Country Status (10)
| Country | Link |
|---|---|
| EP (2) | EP2592089A1 (enExample) |
| KR (1) | KR20140091739A (enExample) |
| CN (1) | CN104066747A (enExample) |
| DK (1) | DK2776452T3 (enExample) |
| ES (1) | ES2558581T3 (enExample) |
| HU (1) | HUE026335T2 (enExample) |
| IN (1) | IN2014KN01209A (enExample) |
| PL (1) | PL2776452T3 (enExample) |
| SI (1) | SI2776452T1 (enExample) |
| WO (1) | WO2013068538A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104231044B (zh) * | 2014-08-13 | 2017-03-22 | 甘肃汇能生物工程有限公司 | 那西肽过柱纯化工艺 |
| CN104371011A (zh) * | 2014-10-21 | 2015-02-25 | 福建省微生物研究所 | 高纯度替考拉宁精粉的纯化方法 |
| CN104910259A (zh) * | 2015-06-02 | 2015-09-16 | 苏州纳微科技有限公司 | 一种替考拉宁的层析纯化方法 |
| CN106589075B (zh) * | 2017-01-23 | 2020-05-05 | 福建省微生物研究所 | 一种替考拉宁的提纯方法 |
| CN109608523B (zh) * | 2018-11-23 | 2023-01-10 | 江苏九阳生物制药有限公司 | 一种高纯度替考拉宁的生产工艺 |
| CN113637050B (zh) * | 2021-09-15 | 2023-03-31 | 丽珠集团福州福兴医药有限公司 | 一种替考拉宁的脱色方法 |
| CN115260294B (zh) * | 2022-08-23 | 2025-09-02 | 北大方正集团有限公司 | 一种替考拉宁的分离纯化方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1496386A (en) | 1975-03-05 | 1977-12-30 | Lepetit Spa | Antibiotics |
| GB8608798D0 (en) | 1986-04-11 | 1986-05-14 | Lepetit Spa | Recovery of glycopeptide antibiotics from aqueous solutions |
| US4845194A (en) | 1987-02-27 | 1989-07-04 | Eli Lilly And Company | Glycopeptide recovery process |
| DE69112750T2 (de) | 1990-10-01 | 1996-09-19 | Lepetit Spa | Verfahren zur Gewinnung von Teicoplanin. |
| KR100321304B1 (ko) | 1999-04-16 | 2002-03-18 | 박호군 | 테이코플라닌의 정제방법 |
| KR100367890B1 (ko) | 2000-03-02 | 2003-01-14 | 은언기 | 랩핑/폴리싱 휠 및 그 제조방법 |
| KR20030017067A (ko) | 2001-08-23 | 2003-03-03 | 정용진 | 변이주 액티노플라네스 테이코마이세티커스 지안네시스 및이로부터 테이코플라닌을 생산하는 방법 |
| KR100459289B1 (ko) | 2002-05-30 | 2004-12-03 | 이연제약주식회사 | 발효액으로부터 테이코플라닌a₂의 회수방법 |
| KR100476818B1 (ko) | 2002-07-19 | 2005-03-17 | 종근당바이오 주식회사 | 테이코플라닌 에이 투 정제 방법 |
| KR100474653B1 (ko) | 2004-04-16 | 2005-03-14 | 동국제약 주식회사 | 타이코플라닌의 고순도 생산방법 |
| CN101423547B (zh) * | 2007-10-31 | 2012-10-17 | 浙江医药股份有限公司新昌制药厂 | 替考拉宁的提纯方法 |
-
2011
- 2011-11-11 EP EP11188759.2A patent/EP2592089A1/en not_active Ceased
-
2012
- 2012-11-09 CN CN201280066349.4A patent/CN104066747A/zh active Pending
- 2012-11-09 PL PL12784004T patent/PL2776452T3/pl unknown
- 2012-11-09 WO PCT/EP2012/072279 patent/WO2013068538A1/en not_active Ceased
- 2012-11-09 EP EP12784004.9A patent/EP2776452B1/en active Active
- 2012-11-09 DK DK12784004.9T patent/DK2776452T3/en active
- 2012-11-09 HU HUE12784004A patent/HUE026335T2/en unknown
- 2012-11-09 IN IN1209KON2014 patent/IN2014KN01209A/en unknown
- 2012-11-09 SI SI201230427T patent/SI2776452T1/sl unknown
- 2012-11-09 KR KR1020147015313A patent/KR20140091739A/ko not_active Ceased
- 2012-11-09 ES ES12784004.9T patent/ES2558581T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN104066747A (zh) | 2014-09-24 |
| EP2592089A1 (en) | 2013-05-15 |
| DK2776452T3 (en) | 2016-01-18 |
| PL2776452T3 (pl) | 2016-03-31 |
| HUE026335T2 (en) | 2016-05-30 |
| EP2776452A1 (en) | 2014-09-17 |
| IN2014KN01209A (enExample) | 2015-10-16 |
| WO2013068538A1 (en) | 2013-05-16 |
| EP2776452B1 (en) | 2015-10-07 |
| SI2776452T1 (sl) | 2016-04-29 |
| ES2558581T3 (es) | 2016-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20140091739A (ko) | 테이코플라닌의 정제 방법 | |
| KR101291494B1 (ko) | 고순도 리포펩티드와 그 제조 방법, 리포펩티드 미셀과 그 제조 방법, 및 고순도 리포펩티드 및 리포펩티드 미셀을 함유하는 약학 조성물 | |
| EP2236513B1 (en) | An improved purification process for lipopeptides | |
| CN102596987B (zh) | 用于纯化粘菌素的方法和纯化的粘菌素组分 | |
| WO2009144739A1 (en) | Amorphous daptomycin and a method of purification thereof | |
| WO2009046618A1 (fr) | Vancomycine déshydroxylée, sa préparation, composition pharmaceutique et son utilisation | |
| US5853720A (en) | Combined process for the purification of vancomycin hydrochloride | |
| EP1735337B1 (en) | Method of producing highly pure teicoplanin | |
| CN113004373B (zh) | 一种达托霉素的纯化方法 | |
| KR0184644B1 (ko) | 테이코플라닌 회수 방법 | |
| WO2018108896A1 (en) | Process for the purification of lipopolypeptide antibiotics | |
| EP2776453B1 (en) | Process of purification of teicoplanin | |
| KR100652320B1 (ko) | 테이코플라닌의 분리 및 정제 방법 | |
| EP2376646B1 (en) | Process for purifying vancomycin wet body | |
| DE102004004043B4 (de) | Reinigung von hochmolekularen Verbindungen mittels Affinitätsmembranchromatographie | |
| CA2628798C (en) | Process for the purification of macrolide antibiotics | |
| MX2008007566A (en) | Process for the purification of macrolide antibiotics |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20140605 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20171109 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20181023 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20190829 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20181023 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |