IL139316A0 - Methods and intermediate compounds for preparing paclitaxel - Google Patents

Methods and intermediate compounds for preparing paclitaxel

Info

Publication number: IL139316A0
Authority: IL; Israel
Prior art keywords: paclitaxel; added; analog; hydroxy; acylating
Prior art date: 1998-05-01

Application number

IL13931699A

Other languages

English (en)

Original Assignee

Napro Biotherapeutics Inc

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.)

1998-05-01

Filing date

1999-04-29

Publication date

2001-11-25

1998-05-01 Priority claimed from US09/071,261 external-priority patent/US6066749A/en

1998-05-01 Priority claimed from US09/071,258 external-priority patent/US6048990A/en

1999-04-29 Application filed by Napro Biotherapeutics Inc filed Critical Napro Biotherapeutics Inc

2001-11-25 Publication of IL139316A0 publication Critical patent/IL139316A0/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
238000000034 method Methods 0.000 title abstract 5
229930012538 Paclitaxel Natural products 0.000 title abstract 4
229960001592 paclitaxel Drugs 0.000 title abstract 4
150000001875 compounds Chemical class 0.000 title abstract 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
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 abstract 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
150000004703 alkoxides Chemical class 0.000 abstract 2
239000002585 base Substances 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
239000002184 metal Substances 0.000 abstract 2
239000002904 solvent Substances 0.000 abstract 2
RZARFIRJROUVLM-UHFFFAOYSA-N 3-azaniumyl-2-hydroxy-3-phenylpropanoate Chemical group OC(=O)C(O)C(N)C1=CC=CC=C1 RZARFIRJROUVLM-UHFFFAOYSA-N 0.000 abstract 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
125000002252 acyl group Chemical group 0.000 abstract 1
239000003513 alkali Substances 0.000 abstract 1
150000001447 alkali salts Chemical class 0.000 abstract 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
230000032050 esterification Effects 0.000 abstract 1
238000005886 esterification reaction Methods 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
125000005270 trialkylamine 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
- 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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL13931699A 1998-05-01 1999-04-29 Methods and intermediate compounds for preparing paclitaxel IL139316A0 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US09/071,261 US6066749A (en)	1998-05-01	1998-05-01	Method for conversion of C-2'-O-protected-10-hydroxy taxol to c-2'-O-protected taxol:useful intermediates in paclitaxel synthesis
US09/071,258 US6048990A (en)	1998-05-01	1998-05-01	Method for selective acylation of C-2'-O-protected-10-hydroxy-taxol at the C-10 position
PCT/US1999/009321 WO1999057105A1 (en)	1998-05-01	1999-04-29	Methods and useful intermediates for paclitaxel synthesis from c-7, c-10 di-cbz baccatin iii

Publications (1)

Publication Number	Publication Date
IL139316A0 true IL139316A0 (en)	2001-11-25

Family

ID=26752024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13931699A IL139316A0 (en)	1998-05-01	1999-04-29	Methods and intermediate compounds for preparing paclitaxel

Country Status (17)

Country	Link
US (1)	US6448417B1 (de)
EP (1)	EP1082316B1 (de)
JP (1)	JP2002513786A (de)
KR (1)	KR20010043230A (de)
CN (1)	CN100348589C (de)
AT (1)	ATE269854T1 (de)
AU (1)	AU745731B2 (de)
BR (1)	BR9910103A (de)
CA (1)	CA2331094A1 (de)
DE (1)	DE69918300T2 (de)
ES (1)	ES2230849T3 (de)
IL (1)	IL139316A0 (de)
NO (1)	NO20005340L (de)
PT (1)	PT1082316E (de)
RU (1)	RU2000130226A (de)
TR (1)	TR200003168T2 (de)
WO (1)	WO1999057105A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2410632A1 (en)	2000-06-22	2001-12-27	David S. Garvey	Nitrosated and nitrosylated taxanes, compositions and methods of use
EP1537094B1 (de) *	2002-08-04	2014-07-02	Phyton Holdings, LLC	Verfahren zur Umwandlung von Taxanamiden in Paclitaxel oder andere Taxane
US20090156828A1 (en) *	2005-12-21	2009-06-18	Tapestry Pharmaceuticals, Inc.	Novel Compounds and Methods for Forming Taxanes and Using the Same
WO2012117417A1 (en) *	2011-02-28	2012-09-07	Shilpa Medicare Limited	Process for preparing (2r, 3s) 2-benzyloxy-3-tert-butoxy carbonyl amino-3-phenyl propionic acid

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
US5015744A (en)	1989-11-14	1991-05-14	Florida State University	Method for preparation of taxol using an oxazinone
FR2678930B1 (fr) *	1991-07-10	1995-01-13	Rhone Poulenc Rorer Sa	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii.
US5229526A (en)	1991-09-23	1993-07-20	Florida State University	Metal alkoxides
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
US5948919A (en) *	1993-02-05	1999-09-07	Napro Biotherapeutics, Inc.	Paclitaxel synthesis from precursor compounds and methods of producing the same
WO1994018186A1 (en)	1993-02-05	1994-08-18	Bryn Mawr College	Synthesis of taxol, analogs and intermediates with variable a-ring side chains
US5675025A (en)	1995-06-07	1997-10-07	Napro Biotherapeutics, Inc.	Paclitaxel synthesis from precursor compounds and methods of producing the same
US6107497A (en) *	1996-02-29	2000-08-22	Napro Biotherapeutics, Inc.	Intermediate for use in docetaxel synthesis and production method therefor
US5688977A (en) *	1996-02-29	1997-11-18	Napro Biotherapeutics, Inc.	Method for docetaxel synthesis
US5750736A (en)	1996-07-11	1998-05-12	Napro Biotherapeutics, Inc.	Method for acylating 10-deacetylbaccatin III selectively at the c-10 position
US5750737A (en) *	1996-09-25	1998-05-12	Sisti; Nicholas J.	Method for paclitaxel synthesis
US5914411A (en)	1998-01-21	1999-06-22	Napro Biotherapeutics, Inc.	Alternate method for acylating 10-deacetylbaccatin III selectively at the C-10 position
US6048990A (en)	1998-05-01	2000-04-11	Napro Biotherapeutics, Inc.	Method for selective acylation of C-2'-O-protected-10-hydroxy-taxol at the C-10 position
US6066749A (en)	1998-05-01	2000-05-23	Napro Biotherapeutics, Inc.	Method for conversion of C-2'-O-protected-10-hydroxy taxol to c-2'-O-protected taxol:useful intermediates in paclitaxel synthesis

1999
- 1999-04-29 DE DE69918300T patent/DE69918300T2/de not_active Expired - Fee Related
- 1999-04-29 AT AT99918900T patent/ATE269854T1/de not_active IP Right Cessation
- 1999-04-29 CA CA002331094A patent/CA2331094A1/en not_active Abandoned
- 1999-04-29 US US09/674,404 patent/US6448417B1/en not_active Expired - Fee Related
- 1999-04-29 CN CNB998057061A patent/CN100348589C/zh not_active Expired - Fee Related
- 1999-04-29 IL IL13931699A patent/IL139316A0/xx unknown
- 1999-04-29 RU RU2000130226/04A patent/RU2000130226A/ru not_active Application Discontinuation
- 1999-04-29 PT PT99918900T patent/PT1082316E/pt unknown
- 1999-04-29 WO PCT/US1999/009321 patent/WO1999057105A1/en not_active Ceased
- 1999-04-29 EP EP99918900A patent/EP1082316B1/de not_active Expired - Lifetime
- 1999-04-29 KR KR1020007012169A patent/KR20010043230A/ko not_active Withdrawn
- 1999-04-29 JP JP2000547075A patent/JP2002513786A/ja active Pending
- 1999-04-29 TR TR2000/03168T patent/TR200003168T2/xx unknown
- 1999-04-29 ES ES99918900T patent/ES2230849T3/es not_active Expired - Lifetime
- 1999-04-29 AU AU36707/99A patent/AU745731B2/en not_active Ceased
- 1999-04-29 BR BR9910103-3A patent/BR9910103A/pt not_active IP Right Cessation
2000
- 2000-10-23 NO NO20005340A patent/NO20005340L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1299355A (zh)	2001-06-13
EP1082316B1 (de)	2004-06-23
US6448417B1 (en)	2002-09-10
KR20010043230A (ko)	2001-05-25
WO1999057105A1 (en)	1999-11-11
NO20005340D0 (no)	2000-10-23
AU3670799A (en)	1999-11-23
ATE269854T1 (de)	2004-07-15
ES2230849T3 (es)	2005-05-01
CA2331094A1 (en)	1999-11-11
DE69918300T2 (de)	2005-06-30
EP1082316A1 (de)	2001-03-14
DE69918300D1 (de)	2004-07-29
AU745731B2 (en)	2002-03-28
RU2000130226A (ru)	2002-11-10
PT1082316E (pt)	2004-11-30
BR9910103A (pt)	2000-12-26
CN100348589C (zh)	2007-11-14
NO20005340L (no)	2000-12-27
JP2002513786A (ja)	2002-05-14
TR200003168T2 (tr)	2001-06-21

Publication	Publication Date	Title
AU678423B2 (en)	1997-05-29	2-debenzoyl-2-acyl taxol derivatives and methods for making same
DK0690856T3 (da)	2003-03-31	Antitumorforbindelser, farmaceutiske præparater, fremgangsmåder til fremstilling deraf og til behandling
NZ534374A (en)	2004-12-24	Method of synthesizing camptothecin-relating compounds
AU2336997A (en)	1997-10-10	Method for docetaxel synthesis
HU225973B1 (en)	2008-02-28	Novel method of esterification of baccatine iii and 10-deacetylbaccatine iii
ZA200207037B (en)	2003-12-02	C-4 carbonate taxanes.
EP0935596A1 (de)	1999-08-18	Verfahren zur hertellung von paclitaxel
PT1082316E (pt)	2004-11-30	Processos e intermediarios uteis para a sintese de paclitaxel a partir de c-7,c-10-di-cbz-bacatina iii
GEP19991873B (en)	1999-12-06	Paclitaxel Synthesis from Precursor Compounds and Methods of Producing the Same
IL127850A0 (en)	1999-10-28	A method for acylating 10-deacetylbaccatin III at the C-10 position
SI1049686T1 (sl)	2006-02-28	Intermediati in postopki, uporabni pri semisintezi paklitaksela in analogov
ES2503265T3 (es)	2014-10-06	Métodos para convertir amidas de taxano en paclitaxel u otros taxanos
EP0941219A4 (de)	1999-10-27
US5973170A (en)	1999-10-26	C-7 metal alkoxides of baccatin III
CA2889448A1 (en)	2014-05-15	Process for the preparation of cabazitaxel and its intermediates
EP1192126A1 (de)	2002-04-03	An der c2-hydroxygruppe geschützte, aktivierte n-acyl(2r,3s)-3-phenylisoserinester und verfahren zu ihrer herstellung