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WO2007045093A1 - Preparation de taxanes - Google Patents

Preparation de taxanes Download PDF

Info

Publication number
WO2007045093A1
WO2007045093A1 PCT/CA2006/001717 CA2006001717W WO2007045093A1 WO 2007045093 A1 WO2007045093 A1 WO 2007045093A1 CA 2006001717 W CA2006001717 W CA 2006001717W WO 2007045093 A1 WO2007045093 A1 WO 2007045093A1
Authority
WO
WIPO (PCT)
Prior art keywords
bio
taxanes
oil
mixture
reactor
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
Application number
PCT/CA2006/001717
Other languages
English (en)
Inventor
Mamdouth Abou-Zaid
Robert G. Graham
Barry A. Freel
David C. Boulard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Canada Minister of Natural Resources
Original Assignee
Canada Minister of Natural Resources
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Canada Minister of Natural Resources filed Critical Canada Minister of Natural Resources
Publication of WO2007045093A1 publication Critical patent/WO2007045093A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
    • C10B53/00—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form
    • C10B53/02—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form of cellulose-containing material
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/141—Feedstock
    • Y02P20/145—Feedstock the feedstock being materials of biological origin

Definitions

  • the resin present in the chromatographic resin/bio-oil mixture may be the
  • Such a separation may involve removing the solvent from the eluted fractions obtained by the above-described procedure, reconstituting the samples in a suitable water miscible organic solvent or aqueous mixture thereof, equilibrating the hydrophobic-interaction resin with a loading solvent (wash solvent) comprising a buffered or unbuffered aqueous/organic solvent mixture that induces the adsorption of taxanes to the resin but does not result in any appreciable retention of impurities having a relatively higher hydrophilicity than that of the taxanes, directly loading the reconstituted mixture of taxanes onto the
  • a loading solvent comprising a buffered or unbuffered aqueous/organic solvent mixture that induces the adsorption of taxanes to the resin but does not result in any appreciable retention of impurities having a relatively higher hydrophilicity than that of the taxanes
  • Sorbent lg/20ml Giga Tubes (Phenomenex, 8B-S100-JEG).
  • the strata-X was
  • Table 7 includes the sample information and peak results from Figure 4c.
  • Table 13 includes the sample information and peak results from Figure 5.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Epoxy Compounds (AREA)

Abstract

La présente invention concerne un procédé permettant de séparer un mélange de taxanes d'une bio-huile composée d'une substance de la biomasse contenant un diterpénoïde. La composition bio-huile peut être tirée d'un végétal des genres Taxus or Austrotaxus. Le procédé comprend la distillation destructrice de la biomasse pour produire une composition bio-huile, suivie par le mélangeage d'une résine chromatographique avec la composition bio-huile afin de former un mélange bio-huile/résine, puis par l'élution du mélange de taxanes à partir du mélange bio-huile/résine en utilisant un solvant d'élution.
PCT/CA2006/001717 2005-10-21 2006-10-20 Preparation de taxanes Ceased WO2007045093A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US72873805P 2005-10-21 2005-10-21
US60/728,738 2005-10-21

Publications (1)

Publication Number Publication Date
WO2007045093A1 true WO2007045093A1 (fr) 2007-04-26

Family

ID=37962164

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2006/001717 Ceased WO2007045093A1 (fr) 2005-10-21 2006-10-20 Preparation de taxanes

Country Status (1)

Country Link
WO (1) WO2007045093A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102653528A (zh) * 2012-04-19 2012-09-05 重庆市碚圣农业科技股份有限公司 用大孔树脂分离纯化紫杉醇与10dabⅲ的方法
US8524087B2 (en) 2009-12-23 2013-09-03 Uop Llc Low metal, low water biomass-derived pyrolysis oils and methods for producing the same
EP2007744A4 (fr) * 2006-04-03 2014-03-26 Pharmatherm Chemicals Inc Procédé et produit d'extraction thermique
US8715490B2 (en) 2009-12-23 2014-05-06 Uop Llc Low metal biomass-derived pyrolysis oils and processes for producing the same
US8864999B2 (en) 2009-12-23 2014-10-21 Uop Llc Methods for regenerating acidic ion-exchange resins and reusing regenerants in such methods
CN104230858A (zh) * 2014-08-08 2014-12-24 中山大学 一种从红豆杉枝叶或树皮中分离纯化紫杉醇的方法
US8961743B2 (en) 2007-11-20 2015-02-24 Ensyn Renewables, Inc. Rapid thermal conversion of biomass
US9044727B2 (en) 2011-09-22 2015-06-02 Ensyn Renewables, Inc. Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material
US9102890B2 (en) 2011-12-12 2015-08-11 Ensyn Renewables, Inc. Fluidized catalytic cracking apparatus
CN105017182A (zh) * 2015-07-06 2015-11-04 贵州玉福临科技开发有限公司 一种从红豆杉中高效提取紫杉醇的方法
US9347005B2 (en) 2011-09-13 2016-05-24 Ensyn Renewables, Inc. Methods and apparatuses for rapid thermal processing of carbonaceous material
US9422478B2 (en) 2010-07-15 2016-08-23 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
US9670413B2 (en) 2012-06-28 2017-06-06 Ensyn Renewables, Inc. Methods and apparatuses for thermally converting biomass
US9951278B2 (en) 2010-05-20 2018-04-24 Ensyn Renewables, Inc. Processes for controlling afterburn in a reheater and for controlling loss of entrained solid particles in combustion product flue gas
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
US10337726B2 (en) 2015-08-21 2019-07-02 Ensyn Renewables, Inc. Liquid biomass heating system
US10400176B2 (en) 2016-12-29 2019-09-03 Ensyn Renewables, Inc. Demetallization of liquid biomass
US10400175B2 (en) 2011-09-22 2019-09-03 Ensyn Renewables, Inc. Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material
US10633606B2 (en) 2012-12-10 2020-04-28 Ensyn Renewables, Inc. Systems and methods for renewable fuel

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2108265A1 (fr) * 1991-04-19 1992-10-20 Hala N. Eisohly Methodes et compositions pour l'isolement de taxanes
CA2470124A1 (fr) * 1992-10-05 1994-04-14 Rhone-Poulenc Rorer S.A. Procede d'obtention de la desacetyl-10 baccatine iii
CA2149151A1 (fr) * 1992-11-27 1994-06-09 David R. Carver Extraction de taxanes grace a des milieux d'echange ionique
US5670673A (en) * 1990-11-02 1997-09-23 University Of Florida Method for the isolation and purification of taxol and its natural analogues
CA2519474A1 (fr) * 2003-03-17 2004-09-30 Natural Pharmaceuticals, Inc. Purification de taxanes et melanges de taxane avec resines liees par polyethyleneimine
US6844420B1 (en) * 1999-07-29 2005-01-18 Ensyn Renewables, Inc. Natural resin formulations

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5670673A (en) * 1990-11-02 1997-09-23 University Of Florida Method for the isolation and purification of taxol and its natural analogues
CA2108265A1 (fr) * 1991-04-19 1992-10-20 Hala N. Eisohly Methodes et compositions pour l'isolement de taxanes
CA2470124A1 (fr) * 1992-10-05 1994-04-14 Rhone-Poulenc Rorer S.A. Procede d'obtention de la desacetyl-10 baccatine iii
CA2149151A1 (fr) * 1992-11-27 1994-06-09 David R. Carver Extraction de taxanes grace a des milieux d'echange ionique
US6844420B1 (en) * 1999-07-29 2005-01-18 Ensyn Renewables, Inc. Natural resin formulations
CA2519474A1 (fr) * 2003-03-17 2004-09-30 Natural Pharmaceuticals, Inc. Purification de taxanes et melanges de taxane avec resines liees par polyethyleneimine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CASS B.J. ET AL.: "Challenges in the isolation of taxanes from Taxus canadensis by fast pyrolysis", J. ANAL. AND APPL. PYROLYSIS, vol. 57, 2001, pages 275 - 285, XP003012157 *

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3252128A1 (fr) * 2006-04-03 2017-12-06 Pharmatherm Chemicals Inc. Procédé d'extraction thermique pour la préparation d'un extrait de taxane
US9127208B2 (en) 2006-04-03 2015-09-08 Pharmatherm Chemicals, Inc. Thermal extraction method and product
EP2007744A4 (fr) * 2006-04-03 2014-03-26 Pharmatherm Chemicals Inc Procédé et produit d'extraction thermique
US9809564B2 (en) 2006-04-03 2017-11-07 Pharmatherm Chemicals, Inc. Thermal extraction method and product
US10544368B2 (en) 2007-11-20 2020-01-28 Ensyn Renewables, Inc. Rapid thermal conversion of biomass
US9631145B2 (en) 2007-11-20 2017-04-25 Ensyn Renewables, Inc. Rapid thermal conversion of biomass
US8961743B2 (en) 2007-11-20 2015-02-24 Ensyn Renewables, Inc. Rapid thermal conversion of biomass
US8864999B2 (en) 2009-12-23 2014-10-21 Uop Llc Methods for regenerating acidic ion-exchange resins and reusing regenerants in such methods
US8524087B2 (en) 2009-12-23 2013-09-03 Uop Llc Low metal, low water biomass-derived pyrolysis oils and methods for producing the same
US8715490B2 (en) 2009-12-23 2014-05-06 Uop Llc Low metal biomass-derived pyrolysis oils and processes for producing the same
US10563127B2 (en) 2010-05-20 2020-02-18 Ensyn Renewables, Inc. Processes for controlling afterburn in a reheater and for controlling loss of entrained solid particles in combustion product flue gas
US9951278B2 (en) 2010-05-20 2018-04-24 Ensyn Renewables, Inc. Processes for controlling afterburn in a reheater and for controlling loss of entrained solid particles in combustion product flue gas
US9422478B2 (en) 2010-07-15 2016-08-23 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
US11028325B2 (en) 2011-02-22 2021-06-08 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
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
US10400175B2 (en) 2011-09-22 2019-09-03 Ensyn Renewables, Inc. Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material
US10794588B2 (en) 2011-09-22 2020-10-06 Ensyn Renewables, Inc. Apparatuses for controlling heat for rapid thermal processing of carbonaceous material and methods for the same
US9410091B2 (en) 2011-12-12 2016-08-09 Ensyn Renewables, Inc. Preparing a fuel from liquid biomass
US9120988B2 (en) 2011-12-12 2015-09-01 Ensyn Renewables, Inc. Methods to increase gasoline yield
US9102888B2 (en) 2011-12-12 2015-08-11 Ensyn Renewables, Inc. Methods for renewable fuels with reduced waste streams
US9102889B2 (en) 2011-12-12 2015-08-11 Ensyn Renewables, Inc. Fluidized catalytic cracker riser quench system
US9422485B2 (en) 2011-12-12 2016-08-23 Ensyn Renewables, Inc. Method of trading cellulosic-renewable identification numbers
US9127223B2 (en) 2011-12-12 2015-09-08 Ensyn Renewables, Inc. Systems and methods for renewable fuel
US9127224B2 (en) 2011-12-12 2015-09-08 Ensyn Renewables, Inc. External steam reduction method in a fluidized catalytic cracker
US10570340B2 (en) 2011-12-12 2020-02-25 Ensyn Renewables, Inc. Systems and methods for renewable fuel
US9120990B2 (en) 2011-12-12 2015-09-01 Ensyn Renewables, Inc. Systems for fuels from biomass
US9102890B2 (en) 2011-12-12 2015-08-11 Ensyn Renewables, Inc. Fluidized catalytic cracking apparatus
US9120989B2 (en) 2011-12-12 2015-09-01 Ensyn Renewables, Inc. Generating cellulosic-renewable identification numbers in a refinery
US9969942B2 (en) 2011-12-12 2018-05-15 Ensyn Renewables, Inc. Systems and methods for renewable fuel
US9109177B2 (en) 2011-12-12 2015-08-18 Ensyn Renewables, Inc. Systems and methods for renewable fuel
US10975315B2 (en) 2011-12-12 2021-04-13 Ensyn Renewables, Inc. Systems and methods for renewable fuel
CN102653528B (zh) * 2012-04-19 2014-07-16 重庆市碚圣农业科技股份有限公司 用大孔树脂分离纯化紫杉醇与10dabⅲ的方法
CN102653528A (zh) * 2012-04-19 2012-09-05 重庆市碚圣农业科技股份有限公司 用大孔树脂分离纯化紫杉醇与10dabⅲ的方法
US9670413B2 (en) 2012-06-28 2017-06-06 Ensyn Renewables, Inc. Methods and apparatuses for thermally converting biomass
US10633606B2 (en) 2012-12-10 2020-04-28 Ensyn Renewables, Inc. Systems and methods for renewable fuel
US10640719B2 (en) 2013-06-26 2020-05-05 Ensyn Renewables, Inc. Systems and methods for renewable fuel
CN104230858B (zh) * 2014-08-08 2016-04-20 中山大学 一种从红豆杉枝叶或树皮中分离纯化紫杉醇的方法
CN104230858A (zh) * 2014-08-08 2014-12-24 中山大学 一种从红豆杉枝叶或树皮中分离纯化紫杉醇的方法
CN105017182A (zh) * 2015-07-06 2015-11-04 贵州玉福临科技开发有限公司 一种从红豆杉中高效提取紫杉醇的方法
US10948179B2 (en) 2015-08-21 2021-03-16 Ensyn Renewables, Inc. Liquid biomass heating system
US10337726B2 (en) 2015-08-21 2019-07-02 Ensyn Renewables, Inc. Liquid biomass heating system
US10400176B2 (en) 2016-12-29 2019-09-03 Ensyn Renewables, Inc. Demetallization of liquid biomass
US10982152B2 (en) 2016-12-29 2021-04-20 Ensyn Renewables, Inc. Demetallization of liquid biomass

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