SK280448B6 - Spôsob prípravy 7-trialkylsilylbaccatínu iii - Google Patents

Spôsob prípravy 7-trialkylsilylbaccatínu iii Download PDF

Info

Publication number: SK280448B6
Authority: SK; Slovakia
Prior art keywords: process according; formula; iii; carbon atoms; desacetylbaccatin
Prior art date: 1994-04-05

Application number

SK1265-96A

Other languages

English (en)

Slovak (sk)

Other versions

SK126596A3 (en

Inventor

Jean-Pierre Bastart

Jean-Pierre Leconte

Original Assignee

Rhone-Poulenc Rorer S. A.

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.)

1994-04-05

Filing date

1995-04-03

Publication date

2000-02-14

1995-04-03 Application filed by Rhone-Poulenc Rorer S. A. filed Critical Rhone-Poulenc Rorer S. A.

1997-04-09 Publication of SK126596A3 publication Critical patent/SK126596A3/sk

2000-02-14 Publication of SK280448B6 publication Critical patent/SK280448B6/sk

Links

238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 18
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 abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
238000002955 isolation Methods 0.000 claims description 3
RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims 1
229910003849 O-Si Inorganic materials 0.000 claims 1
229910003872 O—Si Inorganic materials 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
-1 trialkylsilyl halide Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000006884 silylation reaction Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
229930012538 Paclitaxel Natural products 0.000 description 1
229940123237 Taxane Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical group 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 description 1
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 description 1

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Epoxy Compounds (AREA)
Saccharide Compounds (AREA)
Crystals, And After-Treatments Of Crystals (AREA)
Silicon Compounds (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
Magnetic Resonance Imaging Apparatus (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Internal Circuitry In Semiconductor Integrated Circuit Devices (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Cephalosporin Compounds (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Silicon Polymers (AREA)

SK1265-96A 1994-04-05 1995-04-03 Spôsob prípravy 7-trialkylsilylbaccatínu iii SK280448B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9403979A FR2718137B1 (fr)	1994-04-05	1994-04-05	Procédé de préparation de trialcoylsilyl-7 baccatine III.
PCT/FR1995/000419 WO1995026967A1 (fr)	1994-04-05	1995-04-03	Procede de preparation de trialcoylsilyl-7 baccatine iii

Publications (2)

Publication Number	Publication Date
SK126596A3 SK126596A3 (en)	1997-04-09
SK280448B6 true SK280448B6 (sk)	2000-02-14

Family

ID=9461745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1265-96A SK280448B6 (sk)	1994-04-05	1995-04-03	Spôsob prípravy 7-trialkylsilylbaccatínu iii

Country Status (33)

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

Families Citing this family (12)

* 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
ES2195378T3 (es)	1997-08-21	2003-12-01	Univ Florida State	Procedimiento para la sintesis de taxanos.
EP1318794A2 (de) *	2000-09-22	2003-06-18	Bristol-Myers Squibb Company	Methode zur reduktion der toxizität von kombinationschemotherapien
WO2004033442A2 (en) *	2002-10-09	2004-04-22	Chatham Biotec Ltd.	Novel taxanes and methods related to use and preparation thereof
US7202370B2 (en) *	2003-10-27	2007-04-10	Conor Medsystems, Inc.	Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III
WO2005113528A1 (en) *	2004-05-14	2005-12-01	Immunogen, Inc.	A facile method for synthesizing baccatin iii compounds
CZ298333B6 (cs) *	2005-09-26	2007-08-29	Zentiva, A. S	Zpusob prípravy 7-trialkylsilylbaccatinu III
AU2009282413B2 (en)	2008-08-11	2014-07-17	Nektar Therapeutics	Multi-arm polymeric alkanoate conjugates
WO2012088422A1 (en)	2010-12-22	2012-06-28	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of taxane-based compounds
WO2012088391A1 (en)	2010-12-22	2012-06-28	Nektar Therapeutics	Non-ring hydroxy substituted taxanes and methods for synthesizing the same
US10894087B2 (en)	2010-12-22	2021-01-19	Nektar Therapeutics	Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4823167A (en) *	1986-12-16	1989-04-18	Baxter International Inc.	Catheter calibration device
FR2629818B1 (fr) *	1988-04-06	1990-11-16	Centre Nat Rech Scient	Procede de preparation du taxol
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

1994
- 1994-04-05 FR FR9403979A patent/FR2718137B1/fr not_active Expired - Fee Related
1995
- 1995-03-22 TW TW084102793A patent/TW284765B/zh not_active IP Right Cessation
- 1995-04-03 US US08/722,103 patent/US5670658A/en not_active Expired - Lifetime
- 1995-04-03 CA CA002186916A patent/CA2186916C/fr not_active Expired - Lifetime
- 1995-04-03 NZ NZ284490A patent/NZ284490A/en not_active IP Right Cessation
- 1995-04-03 BR BR9507444A patent/BR9507444A/pt not_active IP Right Cessation
- 1995-04-03 DK DK95916696.8T patent/DK0754185T3/da active
- 1995-04-03 CZ CZ19962900A patent/CZ288397B6/cs not_active IP Right Cessation
- 1995-04-03 WO PCT/FR1995/000419 patent/WO1995026967A1/fr active IP Right Grant
- 1995-04-03 ZA ZA952733A patent/ZA952733B/xx unknown
- 1995-04-03 HU HU9602735A patent/HU214158B/hu unknown
- 1995-04-03 KR KR1019960705642A patent/KR100399246B1/ko not_active IP Right Cessation
- 1995-04-03 UA UA96093735A patent/UA44730C2/uk unknown
- 1995-04-03 ES ES95916696T patent/ES2109103T3/es not_active Expired - Lifetime
- 1995-04-03 CN CN95192429A patent/CN1058497C/zh not_active Expired - Lifetime
- 1995-04-03 DE DE69501080T patent/DE69501080T2/de not_active Expired - Lifetime
- 1995-04-03 EE EE9600143A patent/EE03240B1/xx unknown
- 1995-04-03 AT AT95916696T patent/ATE160351T1/de active
- 1995-04-03 EP EP95916696A patent/EP0754185B1/de not_active Expired - Lifetime
- 1995-04-03 SK SK1265-96A patent/SK280448B6/sk not_active IP Right Cessation
- 1995-04-03 RU RU96120192/04A patent/RU2127729C1/ru active
- 1995-04-03 AU AU23096/95A patent/AU683560B2/en not_active Expired
- 1995-04-03 PL PL95316588A patent/PL316588A1/xx unknown
- 1995-04-03 GE GEAP19953433A patent/GEP19991537B/en unknown
- 1995-04-03 RO RO96-01921A patent/RO115631B1/ro unknown
- 1995-04-03 MX MX9604466A patent/MX9604466A/es unknown
- 1995-04-03 JP JP52546695A patent/JP3718225B2/ja not_active Expired - Lifetime
1996
- 1996-09-24 LT LT96-137A patent/LT4185B/lt not_active IP Right Cessation
- 1996-09-27 NO NO964103A patent/NO305839B1/no not_active IP Right Cessation
- 1996-10-04 BG BG100886A patent/BG62735B1/bg unknown
- 1996-10-04 FI FI964001A patent/FI115970B/fi not_active IP Right Cessation
- 1996-10-07 LV LVP-96-392A patent/LV11691B/lv unknown
1997
- 1997-11-20 GR GR970401504T patent/GR3025448T3/el unknown

Also Published As

Publication number	Publication date
EP0754185A1 (de)	1997-01-22
HUT76035A (en)	1997-06-30
SK126596A3 (en)	1997-04-09
JPH09512522A (ja)	1997-12-16
BG62735B1 (bg)	2000-06-30
NO305839B1 (no)	1999-08-02
PL316588A1 (en)	1997-01-20
GR3025448T3 (en)	1998-02-27
TW284765B (de)	1996-09-01
NO964103L (no)	1996-09-27
CA2186916C (fr)	2004-05-25
DE69501080D1 (de)	1998-01-02
FR2718137A1 (fr)	1995-10-06
GEP19991537B (en)	1999-03-05
ATE160351T1 (de)	1997-12-15
DK0754185T3 (da)	1998-01-26
LT4185B (en)	1997-07-25
DE69501080T2 (de)	1998-04-02
US5670658A (en)	1997-09-23
NZ284490A (en)	1998-08-26
KR100399246B1 (ko)	2004-02-11
NO964103D0 (no)	1996-09-27
LV11691B (en)	1997-06-20
MX9604466A (es)	1997-07-31
AU683560B2 (en)	1997-11-13
AU2309695A (en)	1995-10-23
HU9602735D0 (en)	1996-11-28
JP3718225B2 (ja)	2005-11-24
BR9507444A (pt)	1997-09-16
LT96137A (en)	1997-02-25
RU2127729C1 (ru)	1999-03-20
CN1145073A (zh)	1997-03-12
UA44730C2 (uk)	2002-03-15
WO1995026967A1 (fr)	1995-10-12
CN1058497C (zh)	2000-11-15
LV11691A (lv)	1997-02-20
ZA952733B (en)	1996-01-09
FI115970B (fi)	2005-08-31
FI964001A (fi)	1996-10-04
HU214158B (hu)	1998-01-28
EE03240B1 (et)	1999-12-15
ES2109103T3 (es)	1998-01-01
BG100886A (en)	1998-01-30
CA2186916A1 (fr)	1995-10-12
EP0754185B1 (de)	1997-11-19
CZ290096A3 (en)	1997-01-15
FI964001A0 (fi)	1996-10-04
CZ288397B6 (en)	2001-06-13
RO115631B1 (ro)	2000-04-28
FR2718137B1 (fr)	1996-04-26

Legal Events

Date	Code	Title	Description
2015-06-02	MK4A	Patent expired	Expiry date: 20150403

Publication	Publication Date	Title
SK280448B6 (sk)	2000-02-14	Spôsob prípravy 7-trialkylsilylbaccatínu iii
CA2563905A1 (en)	2005-12-01	A facile method for synthesizing baccatin iii compounds
KR20010102444A (ko)	2001-11-15	10-데아세틸바카틴 ⅲ으로부터 탁산류의 제조 방법
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