ATE223394T1 - Verahren zur selektiven acylierung von 10- deacetylbaccatin-iii in der c-10 position - Google Patents

Verahren zur selektiven acylierung von 10- deacetylbaccatin-iii in der c-10 position

Info

Publication number: ATE223394T1
Authority: AT; Austria
Prior art keywords: iii; deacetylbaccatin; solution; baccatin; organic phase
Prior art date: 1998-01-21

Application number

AT99904208T

Other languages

English (en)

Inventor

Nicholas J Sisti

Jan Zygmunt

Herbert R Brinkman

Madhavi C Chander

Xian Liang

James D Mcchesney

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.)

1998-01-21

Filing date

1999-01-21

Publication date

2002-09-15

1999-01-21 Application filed by Napro Biotherapeutics Inc filed Critical Napro Biotherapeutics Inc

2002-09-15 Application granted granted Critical

2002-09-15 Publication of ATE223394T1 publication Critical patent/ATE223394T1/de

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
230000010933 acylation Effects 0.000 title 1
238000005917 acylation reaction Methods 0.000 title 1
OVMSOCFBDVBLFW-VHLOTGQHSA-N (-)-Baccatin III Natural products 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 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
229930014667 baccatin III Natural products 0.000 abstract 2
239000003795 chemical substances by application Substances 0.000 abstract 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 2
239000012074 organic phase Substances 0.000 abstract 2
229930190007 Baccatin Natural products 0.000 abstract 1
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
239000008346 aqueous phase Substances 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
229910003002 lithium salt Inorganic materials 0.000 abstract 1
159000000002 lithium salts Chemical class 0.000 abstract 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
238000001953 recrystallisation Methods 0.000 abstract 1
239000002904 solvent Substances 0.000 abstract 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Compounds Of Unknown Constitution (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Steroid Compounds (AREA)
Peptides Or Proteins (AREA)
Paper (AREA)
Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Cephalosporin Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

AT99904208T 1998-01-21 1999-01-21 Verahren zur selektiven acylierung von 10- deacetylbaccatin-iii in der c-10 position ATE223394T1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/010,285 US5914411A (en)	1998-01-21	1998-01-21	Alternate method for acylating 10-deacetylbaccatin III selectively at the C-10 position
PCT/US1999/001384 WO1999037632A1 (en)	1998-01-21	1999-01-21	Alternate method for acylating 10-deacetylbaccatin iii selectively at the c-10 position

Publications (1)

Publication Number	Publication Date
ATE223394T1 true ATE223394T1 (de)	2002-09-15

Family

ID=21745026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT99904208T ATE223394T1 (de)	1998-01-21	1999-01-21	Verahren zur selektiven acylierung von 10- deacetylbaccatin-iii in der c-10 position

Country Status (20)

Country	Link
US (1)	US5914411A (de)
EP (1)	EP1056736B1 (de)
JP (1)	JP2002501060A (de)
KR (1)	KR20010034082A (de)
CN (1)	CN1288463A (de)
AT (1)	ATE223394T1 (de)
AU (1)	AU741516B2 (de)
BR (1)	BR9907160A (de)
CA (1)	CA2312350A1 (de)
DE (1)	DE69902757T2 (de)
DK (1)	DK1056736T3 (de)
EA (1)	EA002576B1 (de)
ES (1)	ES2182484T3 (de)
GE (1)	GEP20022800B (de)
IL (1)	IL136043A0 (de)
NO (1)	NO20002923L (de)
NZ (1)	NZ505117A (de)
PT (1)	PT1056736E (de)
TR (1)	TR200001821T2 (de)
WO (1)	WO1999037632A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7288665B1 (en)	1997-08-18	2007-10-30	Florida State University	Process for selective derivatization of taxanes
DE69918300T2 (de)	1998-05-01	2005-06-30	Napro Biotherapeutics, Inc., Boulder	Verfahren und verwendbare zwischenprodukte für paclitaxel synthese von c-7,c-10 di-cbz baccatin iii
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
AU2003273671A1 (en) *	2002-10-09	2004-05-04	Phytogen Life Sciences, Inc.	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

Family Cites Families (3)

* 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
US5440057A (en) *	1993-08-20	1995-08-08	The Scripps Research Institute	Access to taxol analogs
US5750736A (en) *	1996-07-11	1998-05-12	Napro Biotherapeutics, Inc.	Method for acylating 10-deacetylbaccatin III selectively at the c-10 position

1998
- 1998-01-21 US US09/010,285 patent/US5914411A/en not_active Expired - Fee Related
1999
- 1999-01-21 KR KR1020007007691A patent/KR20010034082A/ko not_active Withdrawn
- 1999-01-21 CN CN99802200A patent/CN1288463A/zh active Pending
- 1999-01-21 DE DE69902757T patent/DE69902757T2/de not_active Expired - Fee Related
- 1999-01-21 DK DK99904208T patent/DK1056736T3/da active
- 1999-01-21 BR BR9907160-6A patent/BR9907160A/pt not_active IP Right Cessation
- 1999-01-21 EA EA200000782A patent/EA002576B1/ru not_active IP Right Cessation
- 1999-01-21 IL IL13604399A patent/IL136043A0/xx unknown
- 1999-01-21 EP EP99904208A patent/EP1056736B1/de not_active Expired - Lifetime
- 1999-01-21 CA CA002312350A patent/CA2312350A1/en not_active Abandoned
- 1999-01-21 JP JP2000528555A patent/JP2002501060A/ja active Pending
- 1999-01-21 AT AT99904208T patent/ATE223394T1/de not_active IP Right Cessation
- 1999-01-21 ES ES99904208T patent/ES2182484T3/es not_active Expired - Lifetime
- 1999-01-21 GE GEAP19995525A patent/GEP20022800B/en unknown
- 1999-01-21 WO PCT/US1999/001384 patent/WO1999037632A1/en not_active Ceased
- 1999-01-21 PT PT99904208T patent/PT1056736E/pt unknown
- 1999-01-21 AU AU24657/99A patent/AU741516B2/en not_active Ceased
- 1999-01-21 NZ NZ505117A patent/NZ505117A/xx unknown
- 1999-01-21 TR TR2000/01821T patent/TR200001821T2/xx unknown
2000
- 2000-06-08 NO NO20002923A patent/NO20002923L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IL136043A0 (en)	2001-05-20
AU2465799A (en)	1999-08-09
DE69902757D1 (de)	2002-10-10
NZ505117A (en)	2002-11-26
NO20002923D0 (no)	2000-06-08
AU741516B2 (en)	2001-12-06
CN1288463A (zh)	2001-03-21
WO1999037632A1 (en)	1999-07-29
NO20002923L (no)	2000-09-11
EA002576B1 (ru)	2002-06-27
EA200000782A1 (ru)	2000-12-25
ES2182484T3 (es)	2003-03-01
DE69902757T2 (de)	2003-01-09
CA2312350A1 (en)	1999-07-29
TR200001821T2 (tr)	2001-01-22
PT1056736E (pt)	2002-12-31
US5914411A (en)	1999-06-22
DK1056736T3 (da)	2002-12-30
JP2002501060A (ja)	2002-01-15
GEP20022800B (en)	2002-09-25
KR20010034082A (ko)	2001-04-25
BR9907160A (pt)	2000-10-24
EP1056736A1 (de)	2000-12-06
EP1056736B1 (de)	2002-09-04
EP1056736A4 (de)	2001-04-11

Legal Events

Date	Code	Title	Description
2004-04-15	REN	Ceased due to non-payment of the annual fee

Publication	Publication Date	Title
AU5115493A (en)	1994-04-26	Method of obtaining 10-deacetylbaccatine iii
DE69729100D1 (de)	2004-06-17	Methoden zur selektiven acylierung von 10-deacetylbaccatin iii in der c-10 position
DE69902757D1 (de)	2002-10-10	Verahren zur selektiven acylierung von 10-deacetylbaccatin-iii in der c-10 position
US6133462A (en)	2000-10-17	C-7 CBZ baccatin III and production method therefor
CY1108244T1 (el)	2014-02-12	Παρασκευη μορφης ι καβεργολινης και επιδιαλυτωμενου συμπλοκου αυτης
CA2246541A1 (en)	1997-09-04	Intermediate for use in docetaxel synthesis and production method therefor
BR0015411A (pt)	2002-06-25	Método de preparo de cefpodoxima proxetil altamente pura
Huang et al.	2002	A facile method for the synthesis of glaucine and norglaucine from boldine
EP1497276B1 (de)	2008-08-20	Umwandlung von taxanmolekülen
Andres et al.	1995	Non-metallocatalyzed epoxidation of chiral unsaturated lactams by tertiary amine N-oxides
CZ289996A3 (en)	1997-01-15	Process for preparing 7-hydroxytaxans
Oba et al.	2005	Facile Synthesis of 3‐Hydroxyglutamic Acids via Cyanation of Chiral N‐Acyliminium Cation Derived From (S)‐Malic Acid
CA2361922A1 (en)	2000-08-24	C-7 metal alkoxides of baccatin iii
DE69918300D1 (de)	2004-07-29	Verfahren und verwendbare zwischenprodukte für paclitaxel synthese von c-7,c-10 di-cbz baccatin iii
KR890002125A (ko)	1989-04-08	4-아미노-6, 7-디메톡시 퀴나졸린 유도체의 제조방법.
Zhang et al.	2007	Facile and Efficient Synthesis of Substituted 1, 4‐Dithiafulvalenes from β‐Dicarbonyl Compounds
DE69915081D1 (de)	2004-04-01	Verfahren zur herstellung von c-4-deacetyltaxanen
Jammula et al.	2015	Dehydrative Annulation Strategy for the Construction of Octahydroindolizine Framework: A Diastereoselective Synthesis of (6 R, 8a S)-Octahydroindolizin-6-ol
KR860001087A (ko)	1986-02-22	치환된 1,3-디옥산의 제조방법
KR930700386A (ko)	1993-03-15	페닐이소세린 유도체의 입체선택적 제조 방법
KR970006299A (ko)	1997-02-19	란소프라졸의 제조방법