JP2007523201A - タクロリムスを精製する方法 - Google Patents
タクロリムスを精製する方法 Download PDFInfo
- Publication number
- JP2007523201A JP2007523201A JP2006554356A JP2006554356A JP2007523201A JP 2007523201 A JP2007523201 A JP 2007523201A JP 2006554356 A JP2006554356 A JP 2006554356A JP 2006554356 A JP2006554356 A JP 2006554356A JP 2007523201 A JP2007523201 A JP 2007523201A
- Authority
- JP
- Japan
- Prior art keywords
- tacrolimus
- less
- hplc
- area percent
- water
- 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.)
- Pending
Links
- 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 title claims abstract description 148
- 229960001967 tacrolimus Drugs 0.000 title claims abstract description 145
- 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 title claims abstract description 145
- 238000000034 method Methods 0.000 title claims abstract description 49
- 239000012535 impurity Substances 0.000 claims abstract description 73
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 57
- 229920005989 resin Polymers 0.000 claims abstract description 55
- 239000011347 resin Substances 0.000 claims abstract description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003480 eluent Substances 0.000 claims abstract description 30
- 238000011049 filling Methods 0.000 claims abstract description 25
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 60
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
- 238000001179 sorption measurement Methods 0.000 claims description 27
- 239000003463 adsorbent Substances 0.000 claims description 23
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- ZDQSOHOQTUFQEM-PKUCKEGBSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C\C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-PKUCKEGBSA-N 0.000 claims description 15
- ZDQSOHOQTUFQEM-XCXYXIJFSA-N ascomycin Natural products CC[C@H]1C=C(C)C[C@@H](C)C[C@@H](OC)[C@H]2O[C@@](O)([C@@H](C)C[C@H]2OC)C(=O)C(=O)N3CCCC[C@@H]3C(=O)O[C@H]([C@H](C)[C@@H](O)CC1=O)C(=C[C@@H]4CC[C@@H](O)[C@H](C4)OC)C ZDQSOHOQTUFQEM-XCXYXIJFSA-N 0.000 claims description 15
- RQYGKZGKXDOUEO-HHRHWXIDSA-N dihydro-fk 506 Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)OC([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CCC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 RQYGKZGKXDOUEO-HHRHWXIDSA-N 0.000 claims description 14
- RQYGKZGKXDOUEO-UHFFFAOYSA-N dihydrotacrolimus Natural products CC1C(O)CC(=O)C(CCC)C=C(C)CC(C)CC(OC)C(C(CC2C)OC)OC2(O)C(=O)C(=O)N2CCCCC2C(=O)OC1C(C)=CC1CCC(O)C(OC)C1 RQYGKZGKXDOUEO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 229920001429 chelating resin Polymers 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 238000012856 packing Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 238000004891 communication Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 2
- 229960004592 isopropanol Drugs 0.000 claims description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000002594 sorbent Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 27
- 238000010828 elution Methods 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000001514 detection method Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 239000012296 anti-solvent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000003120 macrolide antibiotic agent Substances 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000011210 chromatographic step Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229940072288 prograf Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 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
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 101001055216 Homo sapiens Interleukin-9 Proteins 0.000 description 1
- 102100026871 Interleukin-9 Human genes 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000008266 deoxy sugars Chemical class 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/282—Porous sorbents
- B01J20/285—Porous sorbents based on polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/42—Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
- B01D15/424—Elution mode
- B01D15/426—Specific type of solvent
-
- 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
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/18—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63862804P | 2004-12-22 | 2004-12-22 | |
| US63881504P | 2004-12-23 | 2004-12-23 | |
| PCT/US2005/047264 WO2006069386A1 (en) | 2004-12-22 | 2005-12-22 | Method of purifying tacrolimus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2007523201A true JP2007523201A (ja) | 2007-08-16 |
Family
ID=36128612
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006554356A Pending JP2007523201A (ja) | 2004-12-22 | 2005-12-22 | タクロリムスを精製する方法 |
| JP2006554355A Pending JP2007523200A (ja) | 2004-12-22 | 2005-12-22 | マクロライドを精製する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006554355A Pending JP2007523200A (ja) | 2004-12-22 | 2005-12-22 | マクロライドを精製する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20060142565A1 (https=) |
| EP (2) | EP1828204A1 (https=) |
| JP (2) | JP2007523201A (https=) |
| CA (2) | CA2586700A1 (https=) |
| IL (2) | IL183241A0 (https=) |
| MX (2) | MX2007005867A (https=) |
| TW (2) | TW200637834A (https=) |
| WO (2) | WO2006069333A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101344012B1 (ko) | 2012-04-09 | 2013-12-23 | 인하대학교 산학협력단 | 모사이동층 크로마토그래피를 이용하여 타크로리무스와 아스코마이신의 혼합액으로부터 타크로리무스를 분리하는 방법 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008059516A2 (en) * | 2006-08-21 | 2008-05-22 | Concord Biotech Limited | Process for purification of macrolides |
| WO2008065887A1 (en) * | 2006-11-27 | 2008-06-05 | Terumo Kabushiki Kaisha | Process for producing o-alkylated rapamycin derivative, and o-alkylated rapamycin derivative |
| KR101003042B1 (ko) * | 2008-03-17 | 2010-12-21 | 종근당바이오 주식회사 | 고순도 타크로리무스의 정제 방법 |
| GB201020032D0 (en) * | 2010-11-25 | 2011-01-12 | Sigmoid Pharma Ltd | Composition |
| CN103554133B (zh) * | 2013-10-31 | 2015-06-24 | 国药集团川抗制药有限公司 | 一种制备高纯度他克莫司的工艺 |
| CN105301159B (zh) * | 2015-10-29 | 2017-01-18 | 无锡福祈制药有限公司 | 一种西罗莫司的高效液相色谱分析方法 |
| CN117402175A (zh) * | 2023-10-18 | 2024-01-16 | 国药集团川抗制药有限公司 | 一种他克莫司的结晶方法及其应用 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3244592A (en) * | 1962-06-09 | 1966-04-05 | Arai Tadashi | Ascomycin and process for its production |
| 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 |
| US4894366A (en) * | 1984-12-03 | 1990-01-16 | Fujisawa Pharmaceutical Company, Ltd. | Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same |
| US5182207A (en) * | 1984-09-14 | 1993-01-26 | American Cyanamid Company | Strains of streptomyces thermoarchaensis |
| US4874843A (en) * | 1987-12-03 | 1989-10-17 | Eli Lilly And Company | Chromatographic purification process |
| JP2639737B2 (ja) * | 1990-01-23 | 1997-08-13 | 寳酒造株式会社 | 新規ｒ１０６類化合物 |
| US5116756A (en) * | 1991-01-28 | 1992-05-26 | Merck & Co., Inc. | Process for producing FK-506 |
| US5194378A (en) * | 1991-01-28 | 1993-03-16 | Merck & Co., Inc. | Process for producing fk-506 |
| US5091389A (en) * | 1991-04-23 | 1992-02-25 | Merck & Co., Inc. | Lipophilic macrolide useful as an immunosuppressant |
| US5227295A (en) * | 1991-11-08 | 1993-07-13 | Dowelanco | Process for isolating A83543 and its components |
| WO1993018042A1 (en) * | 1992-03-02 | 1993-09-16 | Pfizer Inc. | Desosamino derivatives of macrolides as immunosuppressants and antifungal agents |
| US5612316A (en) * | 1992-03-02 | 1997-03-18 | Pfizer Inc. | Fluorosugar derivatives of macrolides |
| US5264355A (en) * | 1992-07-02 | 1993-11-23 | Merck & Co., Inc. | Methlating enzyme from streptomyces MA6858 |
| UA41884C2 (uk) * | 1993-11-05 | 2001-10-15 | Амерікан Хоум Продактс Корпорейшн | Спосіб відокремлення рапаміцину від кислотних, основних та неполярних нейтральних домішок, присутніх в концентраті екстрактів ферментаційного бульйону або маточних розчинів |
| US5622866A (en) * | 1994-06-23 | 1997-04-22 | Merck & Co., Inc. | Expression cassettes useful in construction of integrative and replicative expression vectors for Streptomyces |
| GB9618952D0 (en) * | 1996-09-11 | 1996-10-23 | Sandoz Ltd | Process |
| US5616595A (en) * | 1995-06-07 | 1997-04-01 | Abbott Laboratories | Process for recovering water insoluble compounds from a fermentation broth |
| NZ510819A (en) * | 1998-10-02 | 2004-03-26 | Kosan Biosciences Inc | Polyketide synthase enzymes and recombinant DNA constructs therefor |
| AU1214400A (en) * | 1998-10-20 | 2000-05-08 | Ben Venue Laboratories, Inc. | Process for purification of solvents useful in the preparation of pharmaceuticalcompositions |
| CA2351222A1 (en) * | 1998-11-09 | 2000-05-18 | Aventis Pharma Deutschland Gmbh | Vancoresmycin, a process for its production and its use as a pharmaceutical |
| CN1154651C (zh) * | 1999-05-25 | 2004-06-23 | 藤泽药品工业株式会社 | 分离类似的有机化合物的方法 |
| TW553946B (en) * | 1999-09-08 | 2003-09-21 | Fujisawa Pharmaceutical Co | Method for separating lactone-containing high-molecular weight compounds |
| HRP20020683A2 (en) * | 2000-02-24 | 2004-12-31 | Biogal Gyogyszergyar | Method of purifying a fermentation broth |
| MXPA04007847A (es) * | 2002-02-13 | 2005-02-24 | Biogal Gyogyszergyar | Metodo para extraer un macrolido de biomateria. |
| TW200523266A (en) * | 2003-07-24 | 2005-07-16 | Biogal Gyogyszergyar | Method of purifying macrolides |
-
2005
- 2005-12-22 WO PCT/US2005/046856 patent/WO2006069333A1/en not_active Ceased
- 2005-12-22 TW TW094145958A patent/TW200637834A/zh unknown
- 2005-12-22 EP EP05855421A patent/EP1828204A1/en not_active Withdrawn
- 2005-12-22 CA CA002586700A patent/CA2586700A1/en not_active Abandoned
- 2005-12-22 JP JP2006554356A patent/JP2007523201A/ja active Pending
- 2005-12-22 EP EP05855772A patent/EP1828205A1/en not_active Withdrawn
- 2005-12-22 TW TW094145959A patent/TW200637835A/zh unknown
- 2005-12-22 US US11/317,155 patent/US20060142565A1/en not_active Abandoned
- 2005-12-22 WO PCT/US2005/047264 patent/WO2006069386A1/en not_active Ceased
- 2005-12-22 CA CA002586692A patent/CA2586692A1/en not_active Abandoned
- 2005-12-22 JP JP2006554355A patent/JP2007523200A/ja active Pending
- 2005-12-22 US US11/317,152 patent/US20060149057A1/en not_active Abandoned
- 2005-12-22 MX MX2007005867A patent/MX2007005867A/es unknown
- 2005-12-22 MX MX2007005868A patent/MX2007005868A/es not_active Application Discontinuation
-
2007
- 2007-05-15 IL IL183241A patent/IL183241A0/en unknown
- 2007-05-15 IL IL183240A patent/IL183240A0/en unknown
Non-Patent Citations (1)
| Title |
|---|
| JPN6010027386, Ｋｉｎｏ， Ｔ． ｅｔ． ａｌ．, "ＦＫ−５０６， Ａ ＮＯＶＥＬ ＩＭＭＵＮＯＳＵＰＰＲＥＳＳＡＮＴ ＩＳＯＬＡＴＥＤ ＦＲＯＭ Ａ ＳＴＲＥＰＴＯＭＹＣＥＳ． Ｉ． ＦＥＲＭＥＮＴＡＴＩＯＮ， ＩＳＯＬＡＴＩＯＮ， ＡＮＤ ＰＨＹＳ", Ｔｈｅ Ｊｏｕｒｎａｌ ｏｆ Ａｎｔｉｂｉｏｔｉｃｓ, 1987, Ｖｏｌ．４０ ， Ｎｏ．９, １２４９−１２５５ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101344012B1 (ko) | 2012-04-09 | 2013-12-23 | 인하대학교 산학협력단 | 모사이동층 크로마토그래피를 이용하여 타크로리무스와 아스코마이신의 혼합액으로부터 타크로리무스를 분리하는 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1828204A1 (en) | 2007-09-05 |
| IL183241A0 (en) | 2007-08-19 |
| CA2586700A1 (en) | 2006-06-29 |
| WO2006069333A1 (en) | 2006-06-29 |
| IL183240A0 (en) | 2007-08-19 |
| US20060142565A1 (en) | 2006-06-29 |
| WO2006069386A1 (en) | 2006-06-29 |
| TW200637834A (en) | 2006-11-01 |
| MX2007005868A (es) | 2007-07-04 |
| EP1828205A1 (en) | 2007-09-05 |
| CA2586692A1 (en) | 2006-06-29 |
| US20060149057A1 (en) | 2006-07-06 |
| JP2007523200A (ja) | 2007-08-16 |
| MX2007005867A (es) | 2007-07-04 |
| TW200637835A (en) | 2006-11-01 |
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