KR20000062437A - 폴리머 수지관에 대한 공업 제조용 저압 크로마토그래피에의한 파크리탁셀 및 기타 관련 택산들의 분리 및 정제방법 - Google Patents
폴리머 수지관에 대한 공업 제조용 저압 크로마토그래피에의한 파크리탁셀 및 기타 관련 택산들의 분리 및 정제방법 Download PDFInfo
- Publication number
- KR20000062437A KR20000062437A KR1020000000588A KR20000000588A KR20000062437A KR 20000062437 A KR20000062437 A KR 20000062437A KR 1020000000588 A KR1020000000588 A KR 1020000000588A KR 20000000588 A KR20000000588 A KR 20000000588A KR 20000062437 A KR20000062437 A KR 20000062437A
- Authority
- KR
- South Korea
- Prior art keywords
- taxane
- taxanes
- source
- separating
- fractions
- 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
- 229940123237 Taxane Drugs 0.000 title claims abstract description 58
- 239000002952 polymeric resin Substances 0.000 title claims abstract description 12
- 229920003002 synthetic resin Polymers 0.000 title claims abstract description 12
- 238000000746 purification Methods 0.000 title claims abstract description 6
- 229930012538 Paclitaxel Natural products 0.000 title claims description 39
- 229960001592 paclitaxel Drugs 0.000 title claims description 39
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title claims description 39
- 238000004587 chromatography analysis Methods 0.000 title claims description 17
- 238000002955 isolation Methods 0.000 title description 3
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 41
- 238000000926 separation method Methods 0.000 claims abstract description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 29
- 239000012452 mother liquor Substances 0.000 claims description 26
- 239000012044 organic layer Substances 0.000 claims description 21
- 238000004809 thin layer chromatography Methods 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000002250 absorbent Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000741 silica gel Substances 0.000 claims description 12
- 229910002027 silica gel Inorganic materials 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 241000015728 Taxus canadensis Species 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 229930003935 flavonoid Natural products 0.000 claims description 6
- 150000002215 flavonoids Chemical class 0.000 claims description 6
- 235000017173 flavonoids Nutrition 0.000 claims description 6
- -1 taxane compound Chemical class 0.000 claims description 6
- 230000002745 absorbent Effects 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 229930013686 lignan Natural products 0.000 claims description 5
- 150000005692 lignans Chemical class 0.000 claims description 5
- 235000009408 lignans Nutrition 0.000 claims description 5
- TUSIZTVSUSBSQI-UHFFFAOYSA-N Dihydrocarveol acetate Chemical compound CC1CCC(C(C)=C)CC1OC(C)=O TUSIZTVSUSBSQI-UHFFFAOYSA-N 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 4
- 241001330449 Taxus wallichiana Species 0.000 claims description 4
- 239000003791 organic solvent mixture Substances 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 238000005191 phase separation Methods 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 241001116500 Taxus Species 0.000 claims description 2
- 241001116498 Taxus baccata Species 0.000 claims description 2
- 241000202349 Taxus brevifolia Species 0.000 claims description 2
- 241001330459 Taxus wallichiana var. wallichiana Species 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 235000009065 Taxus cuspidata Nutrition 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000000227 grinding Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229930014667 baccatin III Natural products 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 241000218631 Coniferophyta Species 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 208000037819 metastatic cancer Diseases 0.000 description 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- E—FIXED CONSTRUCTIONS
- E06—DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
- E06B—FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
- E06B7/00—Special arrangements or measures in connection with doors or windows
- E06B7/16—Sealing arrangements on wings or parts co-operating with the wings
- E06B7/22—Sealing arrangements on wings or parts co-operating with the wings by means of elastic edgings, e.g. elastic rubber tubes; by means of resilient edgings, e.g. felt or plush strips, resilient metal strips
- E06B7/23—Plastic, sponge rubber, or like strips or tubes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- E—FIXED CONSTRUCTIONS
- E06—DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
- E06B—FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
- E06B3/00—Window sashes, door leaves, or like elements for closing wall or like openings; Layout of fixed or moving closures, e.g. windows in wall or like openings; Features of rigidly-mounted outer frames relating to the mounting of wing frames
- E06B3/66—Units comprising two or more parallel glass or like panes permanently secured together
- E06B3/67—Units comprising two or more parallel glass or like panes permanently secured together characterised by additional arrangements or devices for heat or sound insulation or for controlled passage of light
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Civil Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Structural Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/226,192 US5969165A (en) | 1999-01-07 | 1999-01-07 | Isolation and purification of paclitaxel and other related taxanes by industrial preparative low pressure chromatography on a polymeric resin column |
| US9/226,192 | 1999-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000062437A true KR20000062437A (ko) | 2000-10-25 |
Family
ID=22847945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020000000588A Ceased KR20000062437A (ko) | 1999-01-07 | 2000-01-07 | 폴리머 수지관에 대한 공업 제조용 저압 크로마토그래피에의한 파크리탁셀 및 기타 관련 택산들의 분리 및 정제방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5969165A (enExample) |
| EP (1) | EP1018510B1 (enExample) |
| JP (1) | JP2000204090A (enExample) |
| KR (1) | KR20000062437A (enExample) |
| CN (1) | CN1266059A (enExample) |
| AR (1) | AR022218A1 (enExample) |
| AT (1) | ATE260908T1 (enExample) |
| AU (1) | AU768026B2 (enExample) |
| BR (1) | BR0000884A (enExample) |
| DE (1) | DE69915241T2 (enExample) |
| DK (1) | DK1018510T3 (enExample) |
| ES (1) | ES2216431T3 (enExample) |
| IL (1) | IL133956A (enExample) |
| IN (1) | IN186600B (enExample) |
| NO (1) | NO321779B1 (enExample) |
| NZ (1) | NZ502204A (enExample) |
| PL (1) | PL337764A1 (enExample) |
| PT (1) | PT1018510E (enExample) |
| RU (1) | RU2201788C2 (enExample) |
| SG (1) | SG87072A1 (enExample) |
| SK (1) | SK292000A3 (enExample) |
| ZA (1) | ZA200000036B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ538766A (en) * | 2000-01-13 | 2006-09-29 | Purdue Research Foundation | A process to purify taxanes from plant biomass |
| US6452024B1 (en) | 2000-02-22 | 2002-09-17 | Chaichem Pharmaceuticals International | Process for extraction and purification of paclitaxel from natural sources |
| US6229027B1 (en) * | 2000-03-10 | 2001-05-08 | Jian Liu | Process for manufacturing paclitaxel and 13-acetyl-9-dihydrobaccatin IV |
| AU2006201733B2 (en) * | 2000-03-10 | 2007-05-24 | Ivax Research, Inc. | Process for manufacturing paclitaxel and 13-acetyl-9-dihydrobaccatin III |
| US6469186B1 (en) | 2000-11-08 | 2002-10-22 | Actipharm, Inc. | Process for mass production of GMP paclitaxel and related taxanes |
| CA2428654A1 (en) * | 2000-11-13 | 2002-05-16 | Lahu Saiji | Isolation of taxanes |
| US6333419B1 (en) * | 2000-11-28 | 2001-12-25 | Indena Spa | Chromatographic separation method of paclitaxel and cephalomannin |
| JP2006503102A (ja) * | 2002-10-17 | 2006-01-26 | ジンギュ リァン | 糖尿病の予防および治療のための天然化合物、その調製方法、およびその薬物的使用。 |
| US6759539B1 (en) | 2003-02-27 | 2004-07-06 | Chaichem Pharmaceuticals International | Process for isolation and purification of paclitaxel from natural sources |
| US8703982B2 (en) | 2003-03-17 | 2014-04-22 | Phyton Holdings Llc | Purification of taxanes |
| CN100448859C (zh) * | 2003-03-17 | 2009-01-07 | 天然医药品公司 | 使用键合有聚乙烯亚胺的树脂提纯紫杉醇和紫杉醇混合物的方法 |
| US6956123B2 (en) | 2003-03-17 | 2005-10-18 | Natural Pharmaccuticals, Inc. | Purification of taxanes and taxane mixtures using polyethyleneimine-bonded resins |
| FR2859996B1 (fr) * | 2003-09-19 | 2006-02-03 | Aventis Pharma Sa | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
| US7259268B2 (en) * | 2003-12-31 | 2007-08-21 | Samyang Genex Corporation | Method for purification of paclitaxel from paclitaxel-containing materials |
| ATE372993T1 (de) * | 2004-07-13 | 2007-09-15 | Indena Spa | Verfahren zur gewinnung von paclitaxel aus taxuspflanzen |
| US7169307B2 (en) * | 2004-09-02 | 2007-01-30 | Jian Liu | Process for the extraction of paclitaxel and 9-dihydro-13-acetylbaccatin III from Taxus |
| US20060074254A1 (en) * | 2004-09-30 | 2006-04-06 | Zisheng Zhang | Process for extracting taxanes |
| CN1331859C (zh) * | 2005-01-04 | 2007-08-15 | 四川华申科技开发有限公司 | 分离紫杉醇和三尖杉磷碱的方法 |
| EP1818328A1 (en) * | 2006-02-10 | 2007-08-15 | 6570763 Canada Inc. | Chromatographic method for the isolation and purification of taxane derivatives |
| WO2007111390A1 (en) * | 2006-03-24 | 2007-10-04 | Postech Foundation | Stationary phase and column using cucurbituril bonded silica gel, and separation method of taxol using the column |
| EP2007744B1 (en) | 2006-04-03 | 2017-05-17 | Pharmatherm Chemicals Inc. | Thermal extraction method for producing a taxane extract |
| US7905990B2 (en) | 2007-11-20 | 2011-03-15 | Ensyn Renewables, Inc. | Rapid thermal conversion of biomass |
| KR101149600B1 (ko) * | 2009-12-31 | 2012-05-29 | 주식회사 삼양제넥스바이오 | 고순도 무수결정형 도세탁셀 제조방법 |
| US20110284359A1 (en) | 2010-05-20 | 2011-11-24 | Uop Llc | Processes for controlling afterburn in a reheater and for controlling loss of entrained solid particles in combustion product flue gas |
| US8499702B2 (en) | 2010-07-15 | 2013-08-06 | Ensyn Renewables, Inc. | Char-handling processes in a pyrolysis system |
| US9441887B2 (en) | 2011-02-22 | 2016-09-13 | Ensyn Renewables, Inc. | Heat removal and recovery in biomass pyrolysis |
| US9347005B2 (en) | 2011-09-13 | 2016-05-24 | Ensyn Renewables, Inc. | Methods and apparatuses for rapid thermal processing of carbonaceous material |
| US9044727B2 (en) | 2011-09-22 | 2015-06-02 | Ensyn Renewables, Inc. | Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material |
| US10400175B2 (en) | 2011-09-22 | 2019-09-03 | Ensyn Renewables, Inc. | Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material |
| US10041667B2 (en) | 2011-09-22 | 2018-08-07 | Ensyn Renewables, Inc. | Apparatuses for controlling heat for rapid thermal processing of carbonaceous material and methods for the same |
| US9109177B2 (en) | 2011-12-12 | 2015-08-18 | Ensyn Renewables, Inc. | Systems and methods for renewable fuel |
| US9670413B2 (en) | 2012-06-28 | 2017-06-06 | Ensyn Renewables, Inc. | Methods and apparatuses for thermally converting biomass |
| WO2014210150A1 (en) | 2013-06-26 | 2014-12-31 | Ensyn Renewables, Inc. | Systems and methods for renewable fuel |
| CN104422749A (zh) * | 2013-09-04 | 2015-03-18 | 南京工业大学 | 一种分离、纯化紫杉醇与三尖杉宁碱的制备方法 |
| CN103588736B (zh) * | 2013-12-03 | 2015-06-03 | 云南汉德生物技术有限公司 | 13-乙酰基-9-羟基巴卡亭iii的提取分离方法 |
| US10337726B2 (en) | 2015-08-21 | 2019-07-02 | Ensyn Renewables, Inc. | Liquid biomass heating system |
| HUP1500603A2 (en) | 2015-12-11 | 2017-06-28 | Rotachrom Tech Kft | Process for the separation of 10-deacetyl baccatin iii |
| WO2018125753A1 (en) | 2016-12-29 | 2018-07-05 | Ensyn Renewables, Inc. | Demetallization of liquid biomass |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5475120A (en) * | 1990-11-02 | 1995-12-12 | University Of Florida | Method for the isolation and purification of taxol and its natural analogues |
| DE69229267T2 (de) * | 1991-04-19 | 1999-12-16 | The University Of Mississippi, University | Verfahren und zubereitungen zur isolierung von taxanen |
| FR2696462B1 (fr) * | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé d'obtention de la désacétyl-10 baccatine III. |
| US5281727A (en) * | 1992-11-27 | 1994-01-25 | Napro Biotherapeutics, Inc. | Method of using ion exchange media to increase taxane yields |
| HU0203995D0 (en) * | 1992-12-23 | 2003-04-28 | Bristol Myers Squibb Co | Oxazole derivatives for synthesis of sidechain-bearing taxanes and preparation thereof |
| US5620875A (en) * | 1995-02-17 | 1997-04-15 | University Of Portland | Transfer of taxol from yew tree cuttings into a culture medium over time |
| JPH08277280A (ja) * | 1995-04-06 | 1996-10-22 | Nippon Steel Corp | イチイ細胞からのタキサン化合物の抽出方法 |
| EP0774010B1 (en) * | 1995-04-29 | 2001-09-26 | Samyang Genex Co., Ltd. | A method for mass production of taxol from taxus genus plant |
| US5654448A (en) * | 1995-10-02 | 1997-08-05 | Xechem International, Inc. | Isolation and purification of paclitaxel from organic matter containing paclitaxel, cephalomannine and other related taxanes |
| JPH1052296A (ja) * | 1996-08-09 | 1998-02-24 | Nippon Oil Co Ltd | タキサン類化合物の製造方法（ｉｉｉ） |
-
1999
- 1999-01-07 US US09/226,192 patent/US5969165A/en not_active Expired - Fee Related
- 1999-12-27 ES ES99126036T patent/ES2216431T3/es not_active Expired - Lifetime
- 1999-12-27 AT AT99126036T patent/ATE260908T1/de not_active IP Right Cessation
- 1999-12-27 DE DE69915241T patent/DE69915241T2/de not_active Expired - Fee Related
- 1999-12-27 DK DK99126036T patent/DK1018510T3/da active
- 1999-12-27 PT PT99126036T patent/PT1018510E/pt unknown
- 1999-12-27 EP EP99126036A patent/EP1018510B1/en not_active Expired - Lifetime
-
2000
- 2000-01-06 RU RU2000100420/12A patent/RU2201788C2/ru not_active IP Right Cessation
- 2000-01-06 JP JP2000000798A patent/JP2000204090A/ja active Pending
- 2000-01-06 IN IN7CA2000 patent/IN186600B/en unknown
- 2000-01-06 NO NO20000070A patent/NO321779B1/no unknown
- 2000-01-07 KR KR1020000000588A patent/KR20000062437A/ko not_active Ceased
- 2000-01-07 SG SG200000086A patent/SG87072A1/en unknown
- 2000-01-07 AU AU10145/00A patent/AU768026B2/en not_active Ceased
- 2000-01-07 CN CN00102118A patent/CN1266059A/zh active Pending
- 2000-01-07 BR BR0000884-2A patent/BR0000884A/pt not_active IP Right Cessation
- 2000-01-07 NZ NZ502204A patent/NZ502204A/en not_active IP Right Cessation
- 2000-01-07 SK SK29-2000A patent/SK292000A3/sk unknown
- 2000-01-07 PL PL00337764A patent/PL337764A1/xx not_active Application Discontinuation
- 2000-01-07 ZA ZA200000036A patent/ZA200000036B/xx unknown
- 2000-01-07 AR ARP000100057A patent/AR022218A1/es active IP Right Grant
- 2000-01-09 IL IL13395600A patent/IL133956A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT1018510E (pt) | 2004-06-30 |
| BR0000884A (pt) | 2001-08-21 |
| DK1018510T3 (da) | 2004-07-05 |
| NO20000070L (no) | 2000-07-10 |
| PL337764A1 (en) | 2000-07-17 |
| AU1014500A (en) | 2000-07-13 |
| US5969165A (en) | 1999-10-19 |
| NO20000070D0 (no) | 2000-01-06 |
| RU2201788C2 (ru) | 2003-04-10 |
| IL133956A (en) | 2003-10-31 |
| AR022218A1 (es) | 2002-09-04 |
| NZ502204A (en) | 2001-06-29 |
| SK292000A3 (en) | 2000-10-09 |
| IL133956A0 (en) | 2001-04-30 |
| EP1018510A1 (en) | 2000-07-12 |
| SG87072A1 (en) | 2002-03-19 |
| EP1018510B1 (en) | 2004-03-03 |
| ATE260908T1 (de) | 2004-03-15 |
| NO321779B1 (no) | 2006-07-03 |
| DE69915241T2 (de) | 2004-12-30 |
| DE69915241D1 (de) | 2004-04-08 |
| AU768026B2 (en) | 2003-11-27 |
| CN1266059A (zh) | 2000-09-13 |
| JP2000204090A (ja) | 2000-07-25 |
| ZA200000036B (en) | 2000-07-12 |
| IN186600B (enExample) | 2001-10-06 |
| ES2216431T3 (es) | 2004-10-16 |
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