WO1995026967A1 - Procede de preparation de trialcoylsilyl-7 baccatine iii - Google Patents

Procede de preparation de trialcoylsilyl-7 baccatine iii Download PDF

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Publication number
WO1995026967A1
WO1995026967A1 PCT/FR1995/000419 FR9500419W WO9526967A1 WO 1995026967 A1 WO1995026967 A1 WO 1995026967A1 FR 9500419 W FR9500419 W FR 9500419W WO 9526967 A1 WO9526967 A1 WO 9526967A1
Authority
WO
WIPO (PCT)
Prior art keywords
iii
trialcoylsilyl
baccatin iii
general formula
deacetyl
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/FR1995/000419
Other languages
English (en)
French (fr)
Inventor
Jean-Pierre Bastart
Jean-Pierre Leconte
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.)
Aventis Pharma SA
Original Assignee
Rhone Poulenc Rorer SA
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
Priority to AU23096/95A priority Critical patent/AU683560B2/en
Priority to UA96093735A priority patent/UA44730C2/uk
Priority to NZ284490A priority patent/NZ284490A/en
Priority to MX9604466A priority patent/MX9604466A/es
Priority to JP52546695A priority patent/JP3718225B2/ja
Priority to EP95916696A priority patent/EP0754185B1/fr
Priority to EE9600143A priority patent/EE03240B1/xx
Priority to RU96120192/04A priority patent/RU2127729C1/ru
Priority to US08/722,103 priority patent/US5670658A/en
Priority to RO96-01921A priority patent/RO115631B1/ro
Priority to CA002186916A priority patent/CA2186916C/fr
Priority to PL95316588A priority patent/PL316588A1/xx
Priority to GEAP19953433A priority patent/GEP19991537B/en
Priority to DE69501080T priority patent/DE69501080T2/de
Application filed by Rhone Poulenc Rorer SA filed Critical Rhone Poulenc Rorer SA
Priority to BR9507444A priority patent/BR9507444A/pt
Priority to SK1265-96A priority patent/SK280448B6/sk
Publication of WO1995026967A1 publication Critical patent/WO1995026967A1/fr
Priority to NO964103A priority patent/NO305839B1/no
Priority to FI964001A priority patent/FI115970B/fi
Priority to BG100886A priority patent/BG62735B1/bg
Anticipated expiration legal-status Critical
Priority to LVP-96-392A priority patent/LV11691B/lv
Priority to GR970401504T priority patent/GR3025448T3/el
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages

Definitions

  • the present invention relates to a new process for the preparation of trialcoylsilyl-7 baccatine III of general formula:
  • OCOC 6 H 5 in which the symbols R, which are identical or different, represent alkyl radicals containing 1 to 4 carbon atoms optionally substituted by a phenyl radical from 10-deacetyl baccatin HI of formula:
  • each of the symbols R preferably represents a straight or branched alkyl radical containing 1 to 4 carbon atoms. More particularly still each of the symbols R represents an ethyl radical.
  • the silylation reaction is carried out by treating 10-deacetyl baccatin III with an excess of a trialkylsilyl halide of general formula:
  • a basic organic solvent such as pyridine
  • trialcoylsilyl-7 deacetyl-10 baccatin III is obtained with a yield close to 85.
  • acetylation is carried out by treating triethylsilyl-7 desaceyl-10 baccatin III with an excess of acetyl chloride, operating in a basic organic solvent such as pyridine at a temperature in the region of 0 ° C.
  • the trialkylsilyloxy-7 baccatin III of formula (I) is obtained with a yield of 85% from triethylsilyl-7 baccatin read.
  • a trialcoylsilyl-7 baccatine III is obtained with a yield close to 72%.
  • 10-deacetyl baccatin III in solution in a basic organic solvent chosen from pyridine and pyridines substituted by one or more alkyl radicals containing 1 to 4 carbon atoms, is treated with a silylating agent of formula general (III) at a temperature between 0 and 15 ° C, then with acetic anhydride at a temperature close to 20 ° C.
  • the implementation of the method according to the invention requires the use of an excess of silylating agent much lower than in the known method.
  • silylating agent Generally, 1.5 to 2.5 moles of silylating agent are used per mole of 10-deacetyl baccatin III used.
  • acetic anhydride Generally, 5 to 7 moles of acetic anhydride are used per mole of 10-deacetyl baccatin III used.
  • Trialkylsilyl-7 baccatin III can be isolated after precipitation in water and crystallization, from its solution in an aliphatic ester such as ethyl acetate, using an ether such as isopropyl ether . Generally, the yield is close to 80% from the 10-deacetyl baccatin HI used.
  • Trialkylsilyl-7 baccatin III obtained according to the method of the present invention, can be used, after isolation or in solution in an aliphatic ester such as ethyl acetate, to prepare paclitaxel or its derivatives according to known methods such as described for example in European patent EP-0 336 840 or in international application WO 92/09589.
  • an aliphatic ester such as ethyl acetate

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epoxy Compounds (AREA)
  • Silicon Compounds (AREA)
  • Crystals, And After-Treatments Of Crystals (AREA)
  • Peptides Or Proteins (AREA)
  • Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
  • Saccharide Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)
  • Internal Circuitry In Semiconductor Integrated Circuit Devices (AREA)
  • Cephalosporin Compounds (AREA)
  • Steroid Compounds (AREA)
  • Silicon Polymers (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/FR1995/000419 1994-04-05 1995-04-03 Procede de preparation de trialcoylsilyl-7 baccatine iii Ceased WO1995026967A1 (fr)

Priority Applications (21)

Application Number Priority Date Filing Date Title
GEAP19953433A GEP19991537B (en) 1994-04-05 1995-04-03 Process for Preparing 7-Trialkylsilyl Baccatin III
NZ284490A NZ284490A (en) 1994-04-05 1995-04-03 Preparation of 7-trialkylsilyl baccatin iii from 10-deacetyl baccatin iii
MX9604466A MX9604466A (es) 1994-04-05 1995-04-03 Proceso de preparacion de 7-trialquilsilil-baccatina iii.
JP52546695A JP3718225B2 (ja) 1994-04-05 1995-04-03 ７−トリアルキルシリルバッカチン▲ｉｉｉ▼の製造法
EP95916696A EP0754185B1 (fr) 1994-04-05 1995-04-03 Procede de preparation de la trialcoylsilyl-7 baccatine iii
EE9600143A EE03240B1 (et) 1994-04-05 1995-04-03 7-trialküülsilüülbakatiin III valmistamise meetod
RU96120192/04A RU2127729C1 (ru) 1994-04-05 1995-04-03 Способ получения 7-триалкилсилил-баккатина iii
US08/722,103 US5670658A (en) 1994-04-05 1995-04-03 Process for preparing 7-trialkylsilyl baccatin III
UA96093735A UA44730C2 (uk) 1994-04-05 1995-04-03 Спосіб одержання 7-триалкілсиліл баккатину iii
CA002186916A CA2186916C (fr) 1994-04-05 1995-04-03 Procede de preparation de trialcoylsilyl-7 baccatine iii
PL95316588A PL316588A1 (en) 1994-04-05 1995-04-03 Method of obtaining trialkylosulyl-7 bacatin iii
AU23096/95A AU683560B2 (en) 1994-04-05 1995-04-03 Process for preparing 7-trialkylsilyl baccatin III
DE69501080T DE69501080T2 (de) 1994-04-05 1995-04-03 Verfahren zur herstellung von 7-trialkylsilyl baccatin iii
RO96-01921A RO115631B1 (ro) 1994-04-05 1995-04-03 Procedeu pentru prepararea 7- trialchilsililbaccatinei iii
BR9507444A BR9507444A (pt) 1994-04-05 1995-04-03 Processo de preparação de trialcoilsilil 7 bacatina III
SK1265-96A SK280448B6 (sk) 1994-04-05 1995-04-03 Spôsob prípravy 7-trialkylsilylbaccatínu iii
NO964103A NO305839B1 (no) 1994-04-05 1996-09-27 FremgangsmÕte for fremstilling av 7-trialkylsilyl-baccatin-III
BG100886A BG62735B1 (bg) 1994-04-05 1996-10-04 Метод за получаване на 7-триалкилсилилбакатин iii
FI964001A FI115970B (fi) 1994-04-05 1996-10-04 Menetelmä 7-trialkyylisilyylibakkatiini III:n valmistamiseksi
LVP-96-392A LV11691B (en) 1994-04-05 1996-10-07 Process for preparing 7-trialkylsilyl baccatin iii
GR970401504T GR3025448T3 (en) 1994-04-05 1997-11-20 Process for preparing 7-trialkylsilyl baccatin iii

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR94/03979 1994-04-05
FR9403979A FR2718137B1 (fr) 1994-04-05 1994-04-05 Procédé de préparation de trialcoylsilyl-7 baccatine III.

Publications (1)

Publication Number Publication Date
WO1995026967A1 true WO1995026967A1 (fr) 1995-10-12

Family

ID=9461745

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR1995/000419 Ceased WO1995026967A1 (fr) 1994-04-05 1995-04-03 Procede de preparation de trialcoylsilyl-7 baccatine iii

Country Status (33)

Country Link
US (1) US5670658A (https=)
EP (1) EP0754185B1 (https=)
JP (1) JP3718225B2 (https=)
KR (1) KR100399246B1 (https=)
CN (1) CN1058497C (https=)
AT (1) ATE160351T1 (https=)
AU (1) AU683560B2 (https=)
BG (1) BG62735B1 (https=)
BR (1) BR9507444A (https=)
CA (1) CA2186916C (https=)
CZ (1) CZ288397B6 (https=)
DE (1) DE69501080T2 (https=)
DK (1) DK0754185T3 (https=)
EE (1) EE03240B1 (https=)
ES (1) ES2109103T3 (https=)
FI (1) FI115970B (https=)
FR (1) FR2718137B1 (https=)
GE (1) GEP19991537B (https=)
GR (1) GR3025448T3 (https=)
HU (1) HU214158B (https=)
LT (1) LT4185B (https=)
LV (1) LV11691B (https=)
MX (1) MX9604466A (https=)
NO (1) NO305839B1 (https=)
NZ (1) NZ284490A (https=)
PL (1) PL316588A1 (https=)
RO (1) RO115631B1 (https=)
RU (1) RU2127729C1 (https=)
SK (1) SK280448B6 (https=)
TW (1) TW284765B (https=)
UA (1) UA44730C2 (https=)
WO (1) WO1995026967A1 (https=)
ZA (1) ZA952733B (https=)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1747209A4 (en) * 2004-05-14 2007-12-12 Immunogen Inc A SIMPLE METHOD OF SYNTHESIZING BACCATINE III COMPOUNDS
WO2012088391A1 (en) 2010-12-22 2012-06-28 Nektar Therapeutics Non-ring hydroxy substituted taxanes and methods for synthesizing the same
US9504755B2 (en) 2008-08-11 2016-11-29 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
US10098865B2 (en) 2010-12-22 2018-10-16 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10894087B2 (en) 2010-12-22 2021-01-19 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5973160A (en) * 1992-12-23 1999-10-26 Poss; Michael A. Methods for the preparation of novel sidechain-bearing taxanes
US7288665B1 (en) * 1997-08-18 2007-10-30 Florida State University Process for selective derivatization of taxanes
CA2302699A1 (en) 1997-08-21 1999-02-25 Florida State University Method for the synthesis of taxanes
HUP0302599A3 (en) 2000-09-22 2005-05-30 Bristol Myers Squibb Co Method for reducing toxicity of combined chemotherapic compositions
ITMI20012185A1 (it) * 2001-10-19 2003-04-19 Indena Spa Procedimento per la preparazione della 14beta-idrossi-baccatina iii-1,14-carbonato
ITMI20012186A1 (it) * 2001-10-19 2003-04-19 Indena Spa Procedimento per la preparazione della 14-beta-idrossi-baccatina iii-1,14-carbonato
JP2006513152A (ja) * 2002-10-09 2006-04-20 ファイトジェン ライフ サイエンシズ インコーポレイテッド 新規タキサンならびにその使用および調製に関する方法
US7202370B2 (en) * 2003-10-27 2007-04-10 Conor Medsystems, Inc. Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III
CZ298333B6 (cs) * 2005-09-26 2007-08-29 Zentiva, A. S Zpusob prípravy 7-trialkylsilylbaccatinu III

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0336840A1 (fr) * 1988-04-06 1989-10-11 Centre National De La Recherche Scientifique (Cnrs) Procédé de préparation du taxol

Family Cites Families (7)

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US4823167A (en) * 1986-12-16 1989-04-18 Baxter International Inc. Catheter calibration device
MX9102128A (es) 1990-11-23 1992-07-08 Rhone Poulenc Rorer Sa Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene
US5229526A (en) * 1991-09-23 1993-07-20 Florida State University Metal alkoxides
US5597931A (en) * 1992-03-30 1997-01-28 Sloan-Kettering Institute For Cancer Research Total synthesis of taxol and analogues thereof
US5475011A (en) * 1993-03-26 1995-12-12 The Research Foundation Of State University Of New York Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment
US5405972A (en) * 1993-07-20 1995-04-11 Florida State University Synthetic process for the preparation of taxol and other tricyclic and tetracyclic taxanes
US5449790A (en) * 1994-04-06 1995-09-12 Hauser Chemical Research, Inc. Preparation of 10-deacetylbaccatin III and 7-protected-10-deacetylbaccatin III derivatives from 10-deacetyl taxol A, 10-deacetyl taxol B, and 10-deacetyl taxol C

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0336840A1 (fr) * 1988-04-06 1989-10-11 Centre National De La Recherche Scientifique (Cnrs) Procédé de préparation du taxol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DENIS J N ET AL: "Highly efficient, practical approach to natural taxol", J. AM. CHEM. SOC. (JACSAT,00027863);88; VOL.110 (17); PP.5917-19, UNIV. SCI., TECHNOL. MED. GRENOBLE;LEDSS; ST. MARTIN D'HERES; 38402; FR. (FR) *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1747209A4 (en) * 2004-05-14 2007-12-12 Immunogen Inc A SIMPLE METHOD OF SYNTHESIZING BACCATINE III COMPOUNDS
US9504755B2 (en) 2008-08-11 2016-11-29 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
US10039737B2 (en) 2008-08-11 2018-08-07 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
US11672776B2 (en) 2008-08-11 2023-06-13 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
WO2012088391A1 (en) 2010-12-22 2012-06-28 Nektar Therapeutics Non-ring hydroxy substituted taxanes and methods for synthesizing the same
US9199954B2 (en) 2010-12-22 2015-12-01 Nektar Therapeutics Non-ring hydroxy substituted taxanes and methods for synthesizing the same
US10098865B2 (en) 2010-12-22 2018-10-16 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10894087B2 (en) 2010-12-22 2021-01-19 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
US11813241B2 (en) 2010-12-22 2023-11-14 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds

Also Published As

Publication number Publication date
HU214158B (hu) 1998-01-28
NO305839B1 (no) 1999-08-02
CZ288397B6 (en) 2001-06-13
LT96137A (en) 1997-02-25
LT4185B (en) 1997-07-25
CN1058497C (zh) 2000-11-15
KR100399246B1 (ko) 2004-02-11
HUT76035A (en) 1997-06-30
TW284765B (https=) 1996-09-01
FI964001L (fi) 1996-10-04
BR9507444A (pt) 1997-09-16
SK126596A3 (en) 1997-04-09
PL316588A1 (en) 1997-01-20
LV11691A (lv) 1997-02-20
EP0754185A1 (fr) 1997-01-22
EE03240B1 (et) 1999-12-15
GEP19991537B (en) 1999-03-05
DE69501080D1 (de) 1998-01-02
NO964103D0 (no) 1996-09-27
LV11691B (en) 1997-06-20
HU9602735D0 (en) 1996-11-28
US5670658A (en) 1997-09-23
BG100886A (en) 1998-01-30
ES2109103T3 (es) 1998-01-01
DE69501080T2 (de) 1998-04-02
DK0754185T3 (da) 1998-01-26
JPH09512522A (ja) 1997-12-16
FR2718137A1 (fr) 1995-10-06
FI115970B (fi) 2005-08-31
UA44730C2 (uk) 2002-03-15
SK280448B6 (sk) 2000-02-14
CZ290096A3 (en) 1997-01-15
FR2718137B1 (fr) 1996-04-26
AU2309695A (en) 1995-10-23
RU2127729C1 (ru) 1999-03-20
ATE160351T1 (de) 1997-12-15
CN1145073A (zh) 1997-03-12
GR3025448T3 (en) 1998-02-27
JP3718225B2 (ja) 2005-11-24
CA2186916A1 (fr) 1995-10-12
NO964103L (no) 1996-09-27
ZA952733B (en) 1996-01-09
CA2186916C (fr) 2004-05-25
NZ284490A (en) 1998-08-26
BG62735B1 (bg) 2000-06-30
AU683560B2 (en) 1997-11-13
RO115631B1 (ro) 2000-04-28
EP0754185B1 (fr) 1997-11-19
MX9604466A (es) 1997-07-31
FI964001A0 (fi) 1996-10-04

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