IL108581A0 - Process for the preparation of taxol, taxol analogues, and their intermediates - Google Patents

Process for the preparation of taxol, taxol analogues, and their intermediates

Info

Publication number: IL108581A0
Authority: IL; Israel
Prior art keywords: taxol; intermediates; analogs; synthesis; preparation
Prior art date: 1993-02-05

Application number

IL10858194A

Other languages

English (en)

Original Assignee

Bryn Mawr College

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.)

1993-02-05

Filing date

1994-02-07

Publication date

1994-05-30

1994-02-07 Application filed by Bryn Mawr College filed Critical Bryn Mawr College

1994-05-30 Publication of IL108581A0 publication Critical patent/IL108581A0/xx

Links

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 abstract 7
229930012538 Paclitaxel Natural products 0.000 title abstract 5
229960001592 paclitaxel Drugs 0.000 title abstract 5
239000000543 intermediate Substances 0.000 title abstract 2
238000000034 method Methods 0.000 title abstract 2
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 abstract 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N DL-isoserine Natural products NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 2
229930014667 baccatin III Natural products 0.000 abstract 2
230000015572 biosynthetic process Effects 0.000 abstract 2
238000003786 synthesis reaction Methods 0.000 abstract 2
RZARFIRJROUVLM-UHFFFAOYSA-N 3-azaniumyl-2-hydroxy-3-phenylpropanoate Chemical class OC(=O)C(O)C(N)C1=CC=CC=C1 RZARFIRJROUVLM-UHFFFAOYSA-N 0.000 abstract 1
238000005917 acylation reaction Methods 0.000 abstract 1
230000032050 esterification Effects 0.000 abstract 1
238000005886 esterification reaction Methods 0.000 abstract 1
238000005222 photoaffinity labeling Methods 0.000 abstract 1
125000002456 taxol group Chemical group 0.000 abstract 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

IL10858194A 1993-02-05 1994-02-07 Process for the preparation of taxol, taxol analogues, and their intermediates IL108581A0 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US1509593A	1993-02-05	1993-02-05

Publications (1)

Publication Number	Publication Date
IL108581A0 true IL108581A0 (en)	1994-05-30

Family

ID=21769500

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10858194A IL108581A0 (en)	1993-02-05	1994-02-07	Process for the preparation of taxol, taxol analogues, and their intermediates

Country Status (12)

Country	Link
US (6)	US5770745A (fr)
EP (2)	EP0682660B1 (fr)
JP (1)	JP3031715B2 (fr)
CN (2)	CN1102829A (fr)
AT (1)	ATE253563T1 (fr)
AU (1)	AU695530B2 (fr)
BR (1)	BR9405687C1 (fr)
CA (1)	CA2155304C (fr)
DE (1)	DE69433297T2 (fr)
IL (1)	IL108581A0 (fr)
NZ (1)	NZ262030A (fr)
WO (1)	WO1994018186A1 (fr)

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* Cited by examiner, † Cited by third party
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US5684175A (en) *	1993-02-05	1997-11-04	Napro Biotherapeutics, Inc.	C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor
ATE253563T1 (de)	1993-02-05	2003-11-15	Bryn Mawr College	Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten
US5442065A (en) *	1993-09-09	1995-08-15	Board Of Regents, The University Of Texas System	Synthesis of tetrahydroquinoline enediyne core analogs of dynemicin
US5677470A (en) *	1994-06-28	1997-10-14	Tanabe Seiyaku Co., Ltd.	Baccatin derivatives and processes for preparing the same
CA2162759A1 (fr) *	1994-11-17	1996-05-18	Kenji Tsujihara	Derives de la baccatine et methodes de preparation
EP0868422A1 (fr) *	1996-09-24	1998-10-07	Marigen S.A.	Ultramicroemulsions constituees de concentres pouvant etre disperses de fa on spontanne, renfermant des esters de composes de baccatine-iii a effet antitumoral et antiviral
US5750737A (en) *	1996-09-25	1998-05-12	Sisti; Nicholas J.	Method for paclitaxel synthesis
CA2188190A1 (fr) *	1996-10-18	1998-04-18	Sarala Balachandran	La semi-synthese d'une composition bacatin iii protegee
US6150537A (en)	1997-12-12	2000-11-21	Emory University	Methods for the esterification of alcohols and compounds useful therefor as potential anticancer agents
US6020507A (en)	1998-03-02	2000-02-01	Bristol-Myers Squibb Company	Synthesis of paclitaxel from baccatin III by protection of the 7-hydroxyl of baccatin III using a strong base and an electrophile
KR20010043230A (ko)	1998-05-01	2001-05-25	패트리샤 에이, 필리어	Ｃ-7, ｃ-10 디-ｃｂｚ 박카틴 ｉｉｉ로부터 파클리탁셀을제조하는 방법 및 이를 제조하는데 사용하기 위한 중간체
FI981717A7 (fi)	1998-08-07	2000-02-08	Borealis As	Katalysaattorikomponentti, joka käsittää magnesiumia, titaania, halogeenia ja elektronidonorin, sen valmistus ja käyttö
US6025516A (en) *	1998-10-14	2000-02-15	Chiragene, Inc.	Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its conversion to C-13 sidechain of taxanes
EP1183250B1 (fr) *	1999-05-28	2006-10-11	Bristol-Myers Squibb Company	Semi-synthese de paclitaxel utilisant des dialkyldichlorosilanes
US6136999A (en) *	1999-06-21	2000-10-24	Napro Biotherapeutics, Inc.	C-2 hydroxyl protected-n-acyl (2R,3S)-3-phenylisoserine substituted phenyl activated esters and method for production thereof
US6143902A (en) *	1999-06-21	2000-11-07	Napro Biotherapeutics, Inc.	C-2 hydroxyl protected-N-acyl (2R,3S)-3-phenylisoserine N-imido activated esters and method for production thereof
AU775373B2 (en)	1999-10-01	2004-07-29	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
IL145637A0 (en) *	2000-02-02	2002-06-30	Univ Florida State Res Found	C7 carbonate substituted taxanes as antitumor agents
AU778991B2 (en) *	2000-02-02	2004-12-23	Florida State University Research Foundation, Inc.	C7 carbamoyloxy substituted taxanes as antitumor agents
US6452024B1 (en)	2000-02-22	2002-09-17	Chaichem Pharmaceuticals International	Process for extraction and purification of paclitaxel from natural sources
US6362217B2 (en) *	2000-03-17	2002-03-26	Bristol-Myers Squibb Company	Taxane anticancer agents
US6358996B1 (en)	2000-06-09	2002-03-19	Napro Biotherapeutics, Inc.	Stable isotope labeling of paclitaxel
CA2410632A1 (fr)	2000-06-22	2001-12-27	David S. Garvey	Taxanes nitroses et nitrosyles, compositions et procedes d'utilisation
DE60126103T2 (de) *	2000-08-18	2007-11-15	Nikon Corp.	Haltevorrichtung für optisches Element
HUP0302599A3 (en)	2000-09-22	2005-05-30	Bristol Myers Squibb Co	Method for reducing toxicity of combined chemotherapic compositions
EP1383754B1 (fr) *	2001-03-23	2011-02-23	ScinoPharm Taiwan, Ltd.	Procede de fabrication de derives de taxane
CA2441484A1 (fr) *	2001-03-23	2002-10-03	Napro Biotherapeutics, Inc.	Conjugues moleculaires destines a etre utilises dans le traitement du cancer
US6452025B1 (en) *	2001-04-25	2002-09-17	Napro Biotherapeutics, Inc.	Three-step conversion of protected taxane ester to paclitaxel
US6479679B1 (en)	2001-04-25	2002-11-12	Napro Biotherapeutics, Inc.	Two-step conversion of protected taxane ester to paclitaxel
US6653501B2 (en)	2001-06-27	2003-11-25	Napro Biotherapeutics, Inc.	Chiral resolution method for producing compounds useful in the synthesis of taxanes
US7173145B2 (en) *	2001-11-29	2007-02-06	University Of Maryland, College Park	Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
ITMI20020782A1 (it) *	2002-04-12	2003-10-13	Indena Spa	Processo semisintetico per la preparazione di n-debenzoilpaclitaxel
US7981928B2 (en)	2002-09-05	2011-07-19	Nanodynamics, Inc.	Chemotherapy method using x-rays
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
US6759539B1 (en)	2003-02-27	2004-07-06	Chaichem Pharmaceuticals International	Process for isolation and purification of paclitaxel from natural sources
US7202370B2 (en)	2003-10-27	2007-04-10	Conor Medsystems, Inc.	Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III
EP1875178A4 (fr) *	2005-04-12	2010-05-26	X Rite Inc	Systemes et procedes pour valider un element de securite d'un objet
CN101370798A (zh) *	2005-12-21	2009-02-18	挂毯药品公司	用于形成紫杉烷的新化合物和方法及其应用
JP2009531446A (ja) *	2006-03-27	2009-09-03	タペストリーファーマシューティカルズインコーポレーテッド	タキサン誘導体の合成のためのコンバージェントプロセス
GB0701523D0 (en)	2007-01-26	2007-03-07	Chatham Biotec Ltd	Semi-synthetic process for the preparation of taxane derivatives
KR101096282B1 (ko)	2009-04-24	2011-12-20	주식회사 삼양제넥스	탁산 유도체를 제조하는 방법
WO2017055522A1 (fr)	2015-09-29	2017-04-06	Academisch Medisch Centrum	Protéines env stabilisées du vih
EP3672983A1 (fr)	2017-08-26	2020-07-01	Academisch Medisch Centrum	Immunogènes glycoprotéiques d'enveloppe de vih améliorés

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2601675B1 (fr) *	1986-07-17	1988-09-23	Rhone Poulenc Sante	Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2601676B1 (fr) *	1986-07-17	1988-09-23	Rhone Poulenc Sante	Procede de preparation du taxol et du desacetyl-10 taxol
FR2629819B1 (fr) *	1988-04-06	1990-11-16	Rhone Poulenc Sante	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii
FR2629818B1 (fr) *	1988-04-06	1990-11-16	Centre Nat Rech Scient	Procede de preparation du taxol
US5175315A (en) *	1989-05-31	1992-12-29	Florida State University	Method for preparation of taxol using β-lactam
US5015744A (en) *	1989-11-14	1991-05-14	Florida State University	Method for preparation of taxol using an oxazinone
US5136060A (en) *	1989-11-14	1992-08-04	Florida State University	Method for preparation of taxol using an oxazinone
FR2658513B1 (fr) *	1990-02-21	1994-02-04	Rhone Poulenc Sante	Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r).
FR2680506B1 (fr) *	1991-08-19	1994-09-02	Rhone Poulenc Rorer Sa	Procede de preparation de derives de la beta-phenylisoserine et leur utilisation.
FR2687150B1 (fr) *	1992-02-07	1995-04-28	Rhone Poulenc Rorer Sa	Procede de preparation de derives du taxane.
FR2687151B1 (fr)	1992-02-07	1994-03-25	Rhone Poulenc Rorer Sa	Nouveaux derives de la baccatine iii et de la desacetyl-10 baccatine iii, leur preparation et les compositions pharmaceutiques qui les contiennent.
US5470866A (en) *	1992-08-18	1995-11-28	Virginia Polytechnic Institute And State University	Method for the conversion of cephalomannine to taxol and for the preparation of n-acyl analogs of taxol
US5319112A (en) *	1992-08-18	1994-06-07	Virgnia Tech Intellectual Properties, Inc.	Method for the conversion of cephalomannine to taxol and for the preparation of N-acyl analogs of taxol
FR2696460B1 (fr)	1992-10-05	1994-11-25	Rhone Poulenc Rorer Sa	Procédé de préparation de dérivés du taxane.
ATE253563T1 (de)	1993-02-05	2003-11-15	Bryn Mawr College	Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten
US5684175A (en) *	1993-02-05	1997-11-04	Napro Biotherapeutics, Inc.	C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor
FR2703353B1 (fr) *	1993-03-29	1995-05-05	Rhone Poulenc Rorer Sa	Procédé de préparation de dérivés de la beta-phénylisosérine.
US5679807A (en)	1995-01-30	1997-10-21	Hauser, Inc.	Preparation of taxol and docetaxel through primary amines

1994
- 1994-02-04 AT AT94907973T patent/ATE253563T1/de not_active IP Right Cessation
- 1994-02-04 JP JP6518249A patent/JP3031715B2/ja not_active Expired - Fee Related
- 1994-02-04 EP EP94907973A patent/EP0682660B1/fr not_active Expired - Lifetime
- 1994-02-04 EP EP02014256A patent/EP1260507A1/fr not_active Withdrawn
- 1994-02-04 AU AU61336/94A patent/AU695530B2/en not_active Expired
- 1994-02-04 NZ NZ262030A patent/NZ262030A/en unknown
- 1994-02-04 BR BR9405687-0A patent/BR9405687C1/pt not_active Application Discontinuation
- 1994-02-04 DE DE69433297T patent/DE69433297T2/de not_active Expired - Lifetime
- 1994-02-04 CA CA2155304A patent/CA2155304C/fr not_active Expired - Lifetime
- 1994-02-04 WO PCT/US1994/001293 patent/WO1994018186A1/fr not_active Ceased
- 1994-02-05 CN CN94102253A patent/CN1102829A/zh active Pending
- 1994-02-07 IL IL10858194A patent/IL108581A0/xx unknown
- 1994-12-15 US US08/357,507 patent/US5770745A/en not_active Expired - Lifetime
1995
- 1995-06-07 US US08/483,083 patent/US5939566A/en not_active Expired - Lifetime
1998
- 1998-02-09 US US09/020,742 patent/US6262281B1/en not_active Expired - Fee Related
1999
- 1999-02-19 US US09/253,325 patent/US6072060A/en not_active Expired - Fee Related
2000
- 2000-03-01 CN CN00103725A patent/CN1284501A/zh active Pending
- 2000-04-11 US US09/547,327 patent/US6307088B1/en not_active Expired - Fee Related
2001
- 2001-05-22 US US09/863,889 patent/US6509484B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2155304A1 (fr)	1994-08-18
CN1284501A (zh)	2001-02-21
DE69433297T2 (de)	2004-10-21
EP0682660B1 (fr)	2003-11-05
US6072060A (en)	2000-06-06
NZ262030A (en)	1997-10-24
EP0682660A1 (fr)	1995-11-22
US6307088B1 (en)	2001-10-23
BR9405687C1 (pt)	2001-08-07
ATE253563T1 (de)	2003-11-15
US5939566A (en)	1999-08-17
JP3031715B2 (ja)	2000-04-10
CA2155304C (fr)	2010-07-20
US6262281B1 (en)	2001-07-17
BR9405687A (pt)	1995-11-21
US5770745A (en)	1998-06-23
AU695530B2 (en)	1998-08-13
EP0682660A4 (fr)	1995-12-20
US6509484B2 (en)	2003-01-21
CN1102829A (zh)	1995-05-24
AU6133694A (en)	1994-08-29
DE69433297D1 (de)	2003-12-11
EP1260507A1 (fr)	2002-11-27
WO1994018186A1 (fr)	1994-08-18
JPH08506587A (ja)	1996-07-16
US20020052517A1 (en)	2002-05-02

Publication	Publication Date	Title
IL108581A0 (en)	1994-05-30	Process for the preparation of taxol, taxol analogues, and their intermediates
EA199800031A1 (ru)	1998-06-25	Синтез паклитаксела из предшественников соединений и способы их получения
EA199800024A1 (ru)	1998-06-25	Синтез паклитаксела из соединений-предшественников и способы их получения
HUT75195A (en)	1997-04-28	Sidechain-bearing taxane derivatives, intermediates and processes for preparation thereof
AU4242993A (en)	1993-12-13	Cultured (taxus) tissues as a source of taxol, related taxanes and other novel anti-tumor/anti-viral compounds
ES8802018A1 (es)	1988-03-16	Un procedimiento para preparar derivados de diamidas sustituidas con 7-oxabicicloheptano y sus analogos de prostaglandina
DE69031534D1 (de)	1997-11-06	Verfahren zur Herstellung von optisch aktiven Zyklobutannukleosiden
FR2696463B1 (fr)	1994-11-25	Procédé d'obtention de la désacétyl-10 baccatine III.
FR2741620B1 (fr)	1997-12-26	Procede de preparation de composes a groupement beta-hydroxy -delta-lactone analogues de la (+) compactine et de la (+) mevinoline
IL129100A0 (en)	2000-02-17	Method for paclitaxel synthesis and a C7-CBZ baccatin III compound
CA2142354A1 (fr)	1994-03-03	Methode de conversion de taxanes en baccatine iii et en 10-desacetylbaccatine iii
GR3015686T3 (en)	1995-07-31	Process for the stereochemical inversion of (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R) enantiomers.
SI1114815T1 (en)	2005-04-30	Process to prepare taxol
DE68901582D1 (de)	1992-06-25	Enantiomere glutaramide als harntreibende verbindungen.
ATE157187T1 (de)	1997-09-15	Werbesäule
ATE121074T1 (de)	1995-04-15	Monocyclische terpen-derivate.
TW284753B (fr)	1996-09-01
HUT49120A (en)	1989-08-28	Process for producing 16-methoxy-16-methyl-prostaglandin el derivative and its intermediate
GB8907008D0 (en)	1989-05-10	Intermediates useful for the synthesis for delphinidin chloride
DE69915081D1 (de)	2004-04-01	Verfahren zur herstellung von c-4-deacetyltaxanen
AR002507A1 (es)	1998-03-25	Proceso mejorado para sintetizar intermediarios de carbapenem
MX9800042A (es)	1998-08-30	Metodos, composiciones, y/o articulos de limpieza/saneamiento, para superficies inanimadas no alimenticias.
MX9604593A (es)	1999-02-01	Composicion de revestimiento curable