WO2007045093A1 - Preparation de taxanes - Google Patents
Preparation de taxanes Download PDFInfo
- 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
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- 229940123237 Taxane Drugs 0.000 title claims abstract description 129
- 238000002360 preparation method Methods 0.000 title description 3
- 239000012075 bio-oil Substances 0.000 claims abstract description 92
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 238000000034 method Methods 0.000 claims abstract description 81
- 229920005989 resin Polymers 0.000 claims abstract description 75
- 239000011347 resin Substances 0.000 claims abstract description 75
- 238000000197 pyrolysis Methods 0.000 claims abstract description 73
- 239000002904 solvent Substances 0.000 claims abstract description 52
- 239000002028 Biomass Substances 0.000 claims abstract description 48
- 241001116500 Taxus Species 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 15
- 241000030967 Austrotaxus Species 0.000 claims abstract description 8
- 150000004141 diterpene derivatives Chemical class 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 81
- 239000000047 product Substances 0.000 claims description 54
- 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 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 26
- 229930012538 Paclitaxel Natural products 0.000 claims description 25
- 229960001592 paclitaxel Drugs 0.000 claims description 25
- 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 claims description 25
- 230000008569 process Effects 0.000 claims description 16
- 239000000377 silicon dioxide Substances 0.000 claims description 16
- 241001116498 Taxus baccata Species 0.000 claims description 14
- 239000012535 impurity Substances 0.000 claims description 14
- 241000894007 species Species 0.000 claims description 13
- 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 claims description 10
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- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 claims description 6
- ZVEGOBHUZTXSFK-TZIKQHFSSA-N 7-xylosyltaxol 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@H]3[C@@H]([C@@H](O)[C@H](O)CO3)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 ZVEGOBHUZTXSFK-TZIKQHFSSA-N 0.000 claims description 6
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- -1 10-O-deacetyltaxol Chemical compound 0.000 claims description 5
- 229930014667 baccatin III Natural products 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
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
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- 238000002955 isolation Methods 0.000 description 8
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960003668 docetaxel Drugs 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
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- ADDGUHVEJPNWQZ-GJKIWTKTSA-N 10-deacetyltaxol b Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](O)C(=O)[C@]3(C)[C@@H](O)C[C@H]4OC[C@]4([C@H]31)OC(C)=O)C2(C)C)C)OC(=O)[C@H](O)[C@@H](NC(=O)C(/C)=C/C)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 ADDGUHVEJPNWQZ-GJKIWTKTSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
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- 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.
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 WO2007045093A1 (fr) | 2005-10-21 | 2006-10-20 | Preparation de taxanes |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2007045093A1 (fr) |
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| EP2007744A1 (fr) * | 2006-04-03 | 2008-12-31 | Pharmatherm Chemicals Inc. | Procédé et produit d'extraction thermique |
| 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 |
| US8715490B2 (en) | 2009-12-23 | 2014-05-06 | Uop Llc | Low metal biomass-derived pyrolysis oils and processes for producing the same |
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| 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 |
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