DE69433297T2 - Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten - Google Patents

Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten Download PDF

Info

Publication number: DE69433297T2
Authority: DE; Germany
Prior art keywords: taxol; analogs; synthesis; ring side; intermediates
Prior art date: 1993-02-05
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.): Expired - Lifetime

Application number

DE69433297T

Other languages

English (en)

Other versions

DE69433297D1 (de

Inventor

Charles Swindell

Nancy Krauss

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.)

Bryn Mawr College

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

1994-02-04

Publication date

2004-10-21

1994-02-04 Application filed by Bryn Mawr College filed Critical Bryn Mawr College

2003-12-11 Application granted granted Critical

2003-12-11 Publication of DE69433297D1 publication Critical patent/DE69433297D1/de

2004-10-21 Publication of DE69433297T2 publication Critical patent/DE69433297T2/de

2014-02-05 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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 6
229930012538 Paclitaxel Natural products 0.000 title abstract 5
229960001592 paclitaxel Drugs 0.000 title abstract 5
230000015572 biosynthetic process Effects 0.000 title abstract 3
238000003786 synthesis reaction Methods 0.000 title abstract 3
239000000543 intermediate Substances 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
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
238000000034 method 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)

DE69433297T 1993-02-05 1994-02-04 Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten Expired - Lifetime DE69433297T2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1509593A	1993-02-05	1993-02-05
PCT/US1994/001293 WO1994018186A1 (en)	1993-02-05	1994-02-04	Synthesis of taxol, analogs and intermediates with variable a-ring side chains

Publications (2)

Publication Number	Publication Date
DE69433297D1 DE69433297D1 (de)	2003-12-11
DE69433297T2 true DE69433297T2 (de)	2004-10-21

Family

ID=21769500

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE69433297T Expired - Lifetime DE69433297T2 (de)	1993-02-05	1994-02-04	Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten

Country Status (12)

Country	Link
US (6)	US5770745A (de)
EP (2)	EP1260507A1 (de)
JP (1)	JP3031715B2 (de)
CN (2)	CN1102829A (de)
AT (1)	ATE253563T1 (de)
AU (1)	AU695530B2 (de)
BR (1)	BR9405687C1 (de)
CA (1)	CA2155304C (de)
DE (1)	DE69433297T2 (de)
IL (1)	IL108581A0 (de)
NZ (1)	NZ262030A (de)
WO (1)	WO1994018186A1 (de)

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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
US5442065A (en) *	1993-09-09	1995-08-15	Board Of Regents, The University Of Texas System	Synthesis of tetrahydroquinoline enediyne core analogs of dynemicin
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CA2162759A1 (en) *	1994-11-17	1996-05-18	Kenji Tsujihara	Baccatin derivatives and processes for preparing the same
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US5750737A (en) *	1996-09-25	1998-05-12	Sisti; Nicholas J.	Method for paclitaxel synthesis
CA2188190A1 (en) *	1996-10-18	1998-04-18	Sarala Balachandran	The semi-synthesis of a protected bacatin iii compound
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
CA2331094A1 (en)	1998-05-01	1999-11-11	Herbert R. Brinkman	Methods and useful intermediates for paclitaxel synthesis from c-7, c-10di-cbz 10-deacetylbaccatin iii
FI981717A (fi)	1998-08-07	2000-02-08	Borealis As	Katalysaattorikomponentti, joka käsittää magnesiumia, titaania, halogeenia ja elektronidonorin, sen valmistus ja käyttö
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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
EP2289549A3 (de)	1999-10-01	2011-06-15	Immunogen, Inc.	Immunokonjugate für Krebsbehandlung
JP2003522168A (ja) *	2000-02-02	2003-07-22	フロリダ・ステイト・ユニバーシティ・リサーチ・ファウンデイション・インコーポレイテッド	抗腫瘍剤としてのｃ７カルバモイルオキシ置換タキサン
WO2001057030A1 (en) *	2000-02-02	2001-08-09	Florida State University Research Foundation, Inc.	C7 carbonate 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
AU2001270070B2 (en) *	2000-06-22	2006-03-16	Nitromed, Inc.	Nitrosated and nitrosylated taxanes, compositions and methods of use
EP1744193A1 (de) *	2000-08-18	2007-01-17	Nikon Corporation	Halter für ein optisches Element mit einem Antriebsmechanismus, der die Bewegung des optischen Elements entlang dreier Koordinatenachsen erlaubt
CA2422964A1 (en) *	2000-09-22	2002-03-28	Bristol Myers Squibb Company	Method for reducing toxicity of combined chemotherapies
US6825166B2 (en) *	2001-03-23	2004-11-30	Tapestry Pharmaceuticals, Inc.	Molecular conjugates for use in treatment of cancer
DE01924282T1 (de) *	2001-03-23	2007-04-19	Scinopharm Taiwan, Ltd.	Verfahren zur herstellung von taxanderivaten
US6479679B1 (en)	2001-04-25	2002-11-12	Napro Biotherapeutics, Inc.	Two-step conversion of protected taxane ester to paclitaxel
US6452025B1 (en) *	2001-04-25	2002-09-17	Napro Biotherapeutics, Inc.	Three-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
WO2003048284A1 (en) *	2001-11-29	2003-06-12	University Of Maryland	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
EP1562927B1 (de) *	2002-10-09	2009-05-13	Chatham Biotec Ltd.	Thio-analoga von paclitaxel und deren vorprodukte
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
US20060244948A1 (en) *	2005-04-12	2006-11-02	Overbeck James L	Systems and methods for validating a security feature of an object
AU2005339274A1 (en) *	2005-12-21	2007-06-28	Tapestry Pharmaceuticals, Inc.	Novel compounds and methods for forming taxanes and using the same
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 (en)	2015-09-29	2017-04-06	Academisch Medisch Centrum	Stabilized env proteins of hiv
WO2019042950A1 (en)	2017-08-26	2019-03-07	Academisch Medisch Centrum	IMPROVED HIV ENVELOPE GLYCOPROTETIC IMMUNOGENS

Family Cites Families (18)

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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
FR2629818B1 (fr) *	1988-04-06	1990-11-16	Centre Nat Rech Scient	Procede de preparation du 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
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
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FR2696460B1 (fr)	1992-10-05	1994-11-25	Rhone Poulenc Rorer Sa	Procédé de préparation de dérivés du taxane.
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ATE253563T1 (de)	1993-02-05	2003-11-15	Bryn Mawr College	Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten
FR2703353B1 (fr) *	1993-03-29	1995-05-05	Rhone Poulenc Rorer Sa	Procédé de préparation de dérivés de la beta-phénylisosérine.
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1994
- 1994-02-04 AT AT94907973T patent/ATE253563T1/de not_active IP Right Cessation
- 1994-02-04 DE DE69433297T patent/DE69433297T2/de not_active Expired - Lifetime
- 1994-02-04 JP JP6518249A patent/JP3031715B2/ja not_active Expired - Fee Related
- 1994-02-04 AU AU61336/94A patent/AU695530B2/en not_active Expired
- 1994-02-04 EP EP02014256A patent/EP1260507A1/de not_active Withdrawn
- 1994-02-04 EP EP94907973A patent/EP0682660B1/de not_active Expired - Lifetime
- 1994-02-04 WO PCT/US1994/001293 patent/WO1994018186A1/en active IP Right Grant
- 1994-02-04 BR BR9405687-0A patent/BR9405687C1/pt not_active Application Discontinuation
- 1994-02-04 NZ NZ262030A patent/NZ262030A/en unknown
- 1994-02-04 CA CA2155304A patent/CA2155304C/en not_active Expired - Lifetime
- 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
AU6133694A (en)	1994-08-29
EP1260507A1 (de)	2002-11-27
EP0682660B1 (de)	2003-11-05
JPH08506587A (ja)	1996-07-16
WO1994018186A1 (en)	1994-08-18
US6072060A (en)	2000-06-06
CA2155304A1 (en)	1994-08-18
CA2155304C (en)	2010-07-20
EP0682660A1 (de)	1995-11-22
CN1102829A (zh)	1995-05-24
EP0682660A4 (de)	1995-12-20
US6509484B2 (en)	2003-01-21
US5770745A (en)	1998-06-23
IL108581A0 (en)	1994-05-30
NZ262030A (en)	1997-10-24
BR9405687A (pt)	1995-11-21
US20020052517A1 (en)	2002-05-02
JP3031715B2 (ja)	2000-04-10
CN1284501A (zh)	2001-02-21
AU695530B2 (en)	1998-08-13
DE69433297D1 (de)	2003-12-11
US6262281B1 (en)	2001-07-17
ATE253563T1 (de)	2003-11-15
BR9405687C1 (pt)	2001-08-07
US5939566A (en)	1999-08-17
US6307088B1 (en)	2001-10-23

Publication	Publication Date	Title
DE69433297D1 (de)	2003-12-11	Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten
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
DE59300852D1 (de)	1995-12-07	Schuh.
BG93228A (bg)	1993-12-24	Метод за получаване на таксол
DE69333905D1 (de)	2005-12-15	Seitenkette tragende Taxanen und deren Zwischenprodukten
NO930774L (no)	1993-09-07	Baccatin-iii-derivater
DE69031534D1 (de)	1997-11-06	Verfahren zur Herstellung von optisch aktiven Zyklobutannukleosiden
PT617018E (pt)	2004-02-27	Beta-lactamas metodos para a preparacao de taxanos e taxanos portadores de cadeias laterais
ATE288427T1 (de)	2005-02-15	Verfahren zur hertellung von paclitaxel
RU93004623A (ru)	1996-03-20	Производные таксана iii, способы их получения
EA199800048A1 (ru)	1998-06-25	С-2′-гидроксил-бензил защищенный, n-карбамат защищенный (2r,3s)-3-фенилизосерин и способ его получения
DE69015956D1 (de)	1995-02-23	Verfahren zur stereochemischen Inversion von (2S,3S)-2-Amino-3-phenyl-1,3-Propandiolen in ihre (2R,3R)-Enantiomere.
ES2065446T3 (es)	1995-02-16	Proceso para la preparacion de amino-compuestos ciclicos con actividad anticonvulsiva.
BR9103343A (pt)	1992-05-05	Processo para a preparacao de esteres e amidas organicos
DE68901582D1 (de)	1992-06-25	Enantiomere glutaramide als harntreibende verbindungen.
ATE175967T1 (de)	1999-02-15	Verfahren zur herstellung von 2-amino-6- halogenopurin und synthese einer zwischenverbindung
FI872195A (fi)	1987-12-03	Foerfarande foer framstaellning av penemderivat.
PT94127A (pt)	1991-01-08	Processo para a producao de 2-oxindol-1-carboxamidas
ES2108997T3 (es)	1998-01-01	Columna publicitaria.
IT1261231B (it)	1996-05-09	Procedimento migliorato per la preparazione di l-(-)-carnitina a partire da un prodotto di scarto avente opposta configurazione.
DE68909143D1 (de)	1993-10-21	Prostaglandin-Vorläufer und ihre Herstellung.
DE69611214D1 (de)	2001-01-18	Hältbare Beschichtungszusammensetzung
DE69014378D1 (de)	1995-01-12	Zwischenprodukte, nutzbar für die Synthese von Delphinidinchlorid.
DE69018531D1 (de)	1995-05-18	Monocyclische Terpen-Derivate.

Legal Events

Date	Code	Title	Description
2008-03-20	8364	No opposition during term of opposition