HK1019596A1 - Method for acylating 10-deacetylbaccatin iii selectively at the c-10 position - Google Patents

Method for acylating 10-deacetylbaccatin iii selectively at the c-10 position

Info

Publication number: HK1019596A1
Authority: HK; Hong Kong
Prior art keywords: acylating; baccatin iii; iii; solution; deacetylbaccatin iii
Prior art date: 1996-07-11

Application number

HK99104736A

Other languages

English (en)

Inventor

Nicholas J Sisti

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.)

1996-07-11

Filing date

1999-10-25

Publication date

2000-02-18

1999-10-25 Application filed by Napro Biotherapeutics Inc filed Critical Napro Biotherapeutics Inc

2000-02-18 Publication of HK1019596A1 publication Critical patent/HK1019596A1/xx

Links

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 title abstract 6
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 7
229930014667 baccatin III Natural products 0.000 abstract 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
239000003795 chemical substances by application Substances 0.000 abstract 2
229910052744 lithium Inorganic materials 0.000 abstract 2
239000002904 solvent Substances 0.000 abstract 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
239000012346 acetyl chloride Substances 0.000 abstract 1
235000019270 ammonium chloride Nutrition 0.000 abstract 1
125000003834 baccatin III group Chemical group 0.000 abstract 1
238000004440 column chromatography Methods 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
238000001953 recrystallisation Methods 0.000 abstract 1
-1 salt compounds Chemical class 0.000 abstract 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cephalosporin Compounds (AREA)

HK99104736A 1996-07-11 1999-10-25 Method for acylating 10-deacetylbaccatin iii selectively at the c-10 position HK1019596A1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/678,759 US5750736A (en)	1996-07-11	1996-07-11	Method for acylating 10-deacetylbaccatin III selectively at the c-10 position
PCT/US1997/012307 WO1998002427A1 (en)	1996-07-11	1997-07-09	Method for acylating 10-deacetylbaccatin iii selectively at the c-10 position

Publications (1)

Publication Number	Publication Date
HK1019596A1 true HK1019596A1 (en)	2000-02-18

Family

ID=24724151

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HK99104736A HK1019596A1 (en)	1996-07-11	1999-10-25	Method for acylating 10-deacetylbaccatin iii selectively at the c-10 position

Country Status (16)

Country	Link
US (1)	US5750736A (zh)
EP (1)	EP0918764B1 (zh)
JP (1)	JP2000514458A (zh)
KR (1)	KR20000023649A (zh)
CN (1)	CN1096453C (zh)
AT (1)	ATE266650T1 (zh)
AU (1)	AU731651B2 (zh)
BR (1)	BR9710234A (zh)
CA (1)	CA2259906A1 (zh)
DE (1)	DE69729100D1 (zh)
EA (1)	EA002001B1 (zh)
HK (1)	HK1019596A1 (zh)
IL (1)	IL127850A (zh)
NO (1)	NO986066L (zh)
NZ (1)	NZ333889A (zh)
WO (1)	WO1998002427A1 (zh)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6005120A (en)	1993-07-20	1999-12-21	Florida State University	Tricyclic and tetracyclic taxanes
US7288665B1 (en) *	1997-08-18	2007-10-30	Florida State University	Process for selective derivatization of taxanes
US5914411A (en) *	1998-01-21	1999-06-22	Napro Biotherapeutics, Inc.	Alternate method for acylating 10-deacetylbaccatin III selectively at the C-10 position
IL139316A0 (en) *	1998-05-01	2001-11-25	Napro Biotherapeutics Inc	Methods and intermediate compounds for preparing paclitaxel
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
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
US6281368B1 (en)	2000-03-16	2001-08-28	Napro Biotherapeutics, Inc.	Simple and efficient hydrazinolysis of C-10 and C-13 ester functionalities of taxanes to obtain 10-DAB III
US6495705B2 (en)	2000-03-16	2002-12-17	Napro Biotherapeutics, Inc.	Efficient process for the production of 10-DAB III by selective hydrazinolysis of various taxanes
US6358996B1 (en)	2000-06-09	2002-03-19	Napro Biotherapeutics, Inc.	Stable isotope labeling of paclitaxel
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

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5229526A (en) *	1991-09-23	1993-07-20	Florida State University	Metal alkoxides
IT1254517B (it) *	1992-03-06	1995-09-25	Indena Spa	14-beta idrossi-10-deacetil-baccatina iii, suoi derivati, loro prepazione ed impiego terapeutico
FR2696463B1 (fr) *	1992-10-05	1994-11-25	Rhone Poulenc Rorer Sa	Procédé d'obtention de la désacétyl-10 baccatine III.
FR2750989B1 (fr) *	1996-07-09	1998-09-25	Rhone Poulenc Rorer Sa	Procede de monoacylation d'hydroxy taxanes
ES2210451T3 (es) *	1997-05-02	2004-07-01	Pharmachemie B.V.	Procedimiento de preparacion de baccatina iii y derivados de los mismos a partir de 10-desacetilbaccatina iii.
US7288665B1 (en) *	1997-08-18	2007-10-30	Florida State University	Process for selective derivatization of taxanes

1996
- 1996-07-11 US US08/678,759 patent/US5750736A/en not_active Expired - Fee Related
1997
- 1997-07-09 AU AU38002/97A patent/AU731651B2/en not_active Ceased
- 1997-07-09 DE DE69729100T patent/DE69729100D1/de not_active Expired - Lifetime
- 1997-07-09 WO PCT/US1997/012307 patent/WO1998002427A1/en active IP Right Grant
- 1997-07-09 EP EP97934954A patent/EP0918764B1/en not_active Expired - Lifetime
- 1997-07-09 IL IL12785097A patent/IL127850A/en not_active IP Right Cessation
- 1997-07-09 JP JP10506245A patent/JP2000514458A/ja not_active Ceased
- 1997-07-09 CA CA002259906A patent/CA2259906A1/en not_active Abandoned
- 1997-07-09 EA EA199900096A patent/EA002001B1/ru not_active IP Right Cessation
- 1997-07-09 AT AT97934954T patent/ATE266650T1/de not_active IP Right Cessation
- 1997-07-09 CN CN97196319A patent/CN1096453C/zh not_active Expired - Fee Related
- 1997-07-09 BR BR9710234-2A patent/BR9710234A/pt unknown
- 1997-07-09 NZ NZ333889A patent/NZ333889A/xx unknown
1998
- 1998-12-22 NO NO986066A patent/NO986066L/no not_active Application Discontinuation
1999
- 1999-01-08 KR KR1019997000102A patent/KR20000023649A/ko not_active Application Discontinuation
- 1999-10-25 HK HK99104736A patent/HK1019596A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
NZ333889A (en)	1999-03-29
DE69729100D1 (de)	2004-06-17
CN1096453C (zh)	2002-12-18
EP0918764B1 (en)	2004-05-12
IL127850A (en)	2001-11-25
KR20000023649A (ko)	2000-04-25
ATE266650T1 (de)	2004-05-15
CA2259906A1 (en)	1998-01-22
EA199900096A1 (ru)	1999-08-26
WO1998002427A1 (en)	1998-01-22
CN1225089A (zh)	1999-08-04
IL127850A0 (en)	1999-10-28
EP0918764A4 (en)	1999-09-01
US5750736A (en)	1998-05-12
JP2000514458A (ja)	2000-10-31
AU731651B2 (en)	2001-04-05
BR9710234A (pt)	2000-01-11
NO986066D0 (no)	1998-12-22
EA002001B1 (ru)	2001-10-22
EP0918764A1 (en)	1999-06-02
AU3800297A (en)	1998-02-09
NO986066L (no)	1999-03-05

Publication	Publication Date	Title
NZ333889A (en)	1999-03-29	Method for acylating 10-deacetylbaccatin iii selectively at the c-10 position
EP0935596B1 (en)	2005-02-02	Method for paclitaxel synthesis
NZ505117A (en)	2002-11-26	Alternate method for acylating 10-deacetylbaccatin III selectively at the C-10 position
CA2246541A1 (en)	1997-09-04	Intermediate for use in docetaxel synthesis and production method therefor
EP1497276B1 (en)	2008-08-20	Conversion of taxane molecules
US5973170A (en)	1999-10-26	C-7 metal alkoxides of baccatin III
RU2007137695A (ru)	2009-04-20	Способ очистки 10-деацетилбаккатина iii от 10-деацетил-2-дебензоил-2-пентеноилбаккатина iii
CZ289996A3 (en)	1997-01-15	Process for preparing 7-hydroxytaxans
Chmielewski et al.	1992	Synthesis of (3 R, 5 S, 6 R) 2, 6-Diacetoxymethylclavam from D-Galactal
WO1999057105A1 (en)	1999-11-11	Methods and useful intermediates for paclitaxel synthesis from c-7, c-10 di-cbz baccatin iii
IL153043A (en)	2004-07-25	Intermediate for baccatin iii derivatives and methods for the production thereof
MXPA99000448A (es)	2000-11-01	Metodo para acilar selectivamente el 10-deacetilbaccatin iii en la posicion c-10
MXPA99002793A (en)	2000-02-02	Method for paclitaxel synthesis

Legal Events

Date	Code	Title	Description
2004-12-15	PF	Patent in force
2007-02-16	PC	Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)	Effective date: 20060709