ZA200406350B - Method for extracting a macrolide from biomatter - Google Patents
Method for extracting a macrolide from biomatter Download PDFInfo
- Publication number
- ZA200406350B ZA200406350B ZA200406350A ZA200406350A ZA200406350B ZA 200406350 B ZA200406350 B ZA 200406350B ZA 200406350 A ZA200406350 A ZA 200406350A ZA 200406350 A ZA200406350 A ZA 200406350A ZA 200406350 B ZA200406350 B ZA 200406350B
- Authority
- ZA
- South Africa
- Prior art keywords
- tacrolimus
- macrolide
- biomatter
- solution
- iso
- Prior art date
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title claims description 110
- 238000000034 method Methods 0.000 title claims description 57
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 73
- 238000000605 extraction Methods 0.000 claims description 71
- 229960001967 tacrolimus Drugs 0.000 claims description 71
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 71
- 239000002904 solvent Substances 0.000 claims description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
- 230000002209 hydrophobic effect Effects 0.000 claims description 46
- 238000000855 fermentation Methods 0.000 claims description 30
- 230000004151 fermentation Effects 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 25
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 25
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 244000005700 microbiome Species 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- -1 aliphatic ketones Chemical class 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 241000187391 Streptomyces hygroscopicus Species 0.000 claims description 7
- 241000187398 Streptomyces lividans Species 0.000 claims description 7
- 241001647839 Streptomyces tsukubensis Species 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 5
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 5
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 5
- 229940090181 propyl acetate Drugs 0.000 claims description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 4
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 238000010898 silica gel chromatography Methods 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 4
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229940041033 macrolides Drugs 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001378407 Seegeriella Species 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229960004099 azithromycin Drugs 0.000 description 1
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 229960002626 clarithromycin Drugs 0.000 description 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000008266 deoxy sugars Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- JBAXWZGBNPCMNR-UHFFFAOYSA-N hexan-2-one Chemical compound CCCCC(C)=O.CCCCC(C)=O JBAXWZGBNPCMNR-UHFFFAOYSA-N 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/22—Eight-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0288—Applications, solvents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/005—Selection of auxiliary, e.g. for control of crystallisation nuclei, of crystal growth, of adherence to walls; Arrangements for introduction thereof
- B01D9/0054—Use of anti-solvent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
- Y10S435/898—Streptomyces hygroscopicus
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35695902P | 2002-02-13 | 2002-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200406350B true ZA200406350B (en) | 2006-11-29 |
Family
ID=27734710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200406350A ZA200406350B (en) | 2002-02-13 | 2003-02-12 | Method for extracting a macrolide from biomatter |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7432074B2 (de) |
| EP (1) | EP1474404A4 (de) |
| JP (1) | JP4261365B2 (de) |
| KR (1) | KR20040086369A (de) |
| CN (1) | CN100338043C (de) |
| AU (1) | AU2003213024A1 (de) |
| CA (1) | CA2475383C (de) |
| HR (1) | HRP20040765A2 (de) |
| IL (1) | IL163481A (de) |
| IS (1) | IS7393A (de) |
| MX (1) | MXPA04007847A (de) |
| NO (1) | NO20043788L (de) |
| PL (1) | PL374059A1 (de) |
| WO (1) | WO2003068980A2 (de) |
| ZA (1) | ZA200406350B (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7452692B2 (en) * | 2002-02-13 | 2008-11-18 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Method for extracting a macrolide from biomatter |
| JP4261365B2 (ja) | 2002-02-13 | 2009-04-30 | テバ ジョジセルジャール ザ−トケルエン ムケド レ−スベニュタ−ルシャシャ−グ | 生物学的物質からのマクロライドの抽出方法 |
| US7232486B2 (en) * | 2003-03-31 | 2007-06-19 | TEVA Gyógyszergyár Zártkörűen Működő Részvénytársaság | Crystallization and purification of macrolides |
| US20060169199A1 (en) * | 2003-03-31 | 2006-08-03 | Vilmos Keri | Crystallization and purification of macrolides |
| ES2297481T3 (es) * | 2003-07-24 | 2008-05-01 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Metodo para purificar macrolidos. |
| AU2003286417A1 (en) * | 2003-12-05 | 2005-06-24 | Biocon Limited | Process for the purification of macrolides |
| KR100485877B1 (ko) * | 2003-12-30 | 2005-04-28 | 종근당바이오 주식회사 | 타크롤리무스를 생산하는 미생물 및 이를 이용한타크롤리무스의 대량 생산방법 |
| CA2562805C (en) | 2004-04-12 | 2014-03-11 | Biocon Limited | Process for the production of macrolides using a novel strain, streptomyces sp. bicc 7522 |
| CN101031653A (zh) * | 2004-09-10 | 2007-09-05 | 伊瓦克斯制药有限公司 | 大环内酯化合物的分离方法 |
| BRPI0515695A (pt) * | 2004-09-10 | 2008-03-04 | Ivax Pharmaceuticals Sro | processo para isolamento de tacrolimus cristalino |
| JP2007519757A (ja) * | 2004-12-01 | 2007-07-19 | テバ ジョジセルジャール ザ−トケルエン ムケド レ−スベニュタ−ルシャシャ−グ | ピメクロリマスの調製方法 |
| US20060149057A1 (en) * | 2004-12-22 | 2006-07-06 | Vilmos Keri | Method of purifying macrolides |
| JP2007527434A (ja) * | 2005-01-05 | 2007-09-27 | テバ ジョジセルジャール ザ−トケルエン ムケド レ−スベニュタ−ルシャシャ−グ | 非晶質タクロリマス及びその調製 |
| CN108384819B (zh) * | 2017-02-03 | 2021-06-25 | 上海医药工业研究院 | 一种用于发酵他克莫司的培养基以及发酵方法 |
| CN112390817B (zh) * | 2019-08-19 | 2023-07-07 | 鲁南制药集团股份有限公司 | 一种盐析萃取他克莫司发酵液的方法 |
| CN112730704B (zh) * | 2021-02-04 | 2022-08-16 | 福建省微生物研究所 | 一种他克莫司软膏有关物质测定的前处理方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2121517C3 (de) | 1971-04-30 | 1974-06-27 | Leningradskij Nautschno-Issledowatelskij Institut Antibiotikow, Ssr, Leningrad (Sowjetunion) | Verfahren zur Gewinnung von Amphoterizin B |
| US3993749A (en) * | 1974-04-12 | 1976-11-23 | Ayerst Mckenna And Harrison Ltd. | Rapamycin and process of preparation |
| US4160861A (en) | 1977-10-03 | 1979-07-10 | Merck & Co., Inc. | Method for the separation of antibiotic macrolides |
| JPS591694B2 (ja) * | 1981-12-28 | 1984-01-13 | 三菱瓦斯化学株式会社 | ４−ヒドロキシ−２，４，６−トリメチルシクロヘキサ−２，５−ジエン−１−オンの製造法 |
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| JP4261365B2 (ja) | 2002-02-13 | 2009-04-30 | テバ ジョジセルジャール ザ−トケルエン ムケド レ−スベニュタ−ルシャシャ−グ | 生物学的物質からのマクロライドの抽出方法 |
-
2003
- 2003-02-12 JP JP2003568091A patent/JP4261365B2/ja not_active Expired - Fee Related
- 2003-02-12 PL PL03374059A patent/PL374059A1/xx not_active Application Discontinuation
- 2003-02-12 EP EP03709066A patent/EP1474404A4/de not_active Withdrawn
- 2003-02-12 US US10/366,266 patent/US7432074B2/en not_active Expired - Fee Related
- 2003-02-12 CA CA002475383A patent/CA2475383C/en not_active Expired - Fee Related
- 2003-02-12 MX MXPA04007847A patent/MXPA04007847A/es active IP Right Grant
- 2003-02-12 ZA ZA200406350A patent/ZA200406350B/en unknown
- 2003-02-12 AU AU2003213024A patent/AU2003213024A1/en not_active Abandoned
- 2003-02-12 CN CNB038073277A patent/CN100338043C/zh not_active Expired - Fee Related
- 2003-02-12 KR KR10-2004-7012482A patent/KR20040086369A/ko active IP Right Grant
- 2003-02-12 WO PCT/US2003/004222 patent/WO2003068980A2/en active Application Filing
-
2004
- 2004-08-11 IS IS7393A patent/IS7393A/is unknown
- 2004-08-12 IL IL163481A patent/IL163481A/en not_active IP Right Cessation
- 2004-08-25 HR HR20040765A patent/HRP20040765A2/hr not_active Application Discontinuation
- 2004-09-09 NO NO20043788A patent/NO20043788L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003068980A3 (en) | 2003-12-31 |
| IS7393A (is) | 2004-08-11 |
| PL374059A1 (en) | 2005-09-19 |
| US7432074B2 (en) | 2008-10-07 |
| CN100338043C (zh) | 2007-09-19 |
| AU2003213024A1 (en) | 2003-09-04 |
| NO20043788L (no) | 2004-09-09 |
| US20030166924A1 (en) | 2003-09-04 |
| WO2003068980A2 (en) | 2003-08-21 |
| EP1474404A2 (de) | 2004-11-10 |
| CA2475383A1 (en) | 2003-08-21 |
| EP1474404A4 (de) | 2006-01-11 |
| JP4261365B2 (ja) | 2009-04-30 |
| IL163481A (en) | 2010-04-29 |
| JP2005525105A (ja) | 2005-08-25 |
| KR20040086369A (ko) | 2004-10-08 |
| CA2475383C (en) | 2009-12-22 |
| MXPA04007847A (es) | 2005-02-24 |
| CN1649852A (zh) | 2005-08-03 |
| HRP20040765A2 (en) | 2005-02-28 |
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