DK1056736T3 - Alternativ fremgangsmåde til acylering af 10-deacetylbaccatin III selektivt i C-10-stillingen - Google Patents

Alternativ fremgangsmåde til acylering af 10-deacetylbaccatin III selektivt i C-10-stillingen

Info

Publication number: DK1056736T3
Authority: DK; Denmark
Prior art keywords: acylating; deacetylbaccatin iii; solution; iii; baccatin
Prior art date: 1998-01-21

Application number

DK99904208T

Other languages

Danish (da)

English (en)

Inventor

Nicholas J Sisti

Herbert R Brinkman

Madhavi C Chander

Xian Liang

James D Mcchesney

Jan Zygmunt

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

2002-12-30

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

2002-12-30 Application granted granted Critical

2002-12-30 Publication of DK1056736T3 publication Critical patent/DK1056736T3/da

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

DK99904208T 1998-01-21 1999-01-21 Alternativ fremgangsmåde til acylering af 10-deacetylbaccatin III selektivt i C-10-stillingen DK1056736T3 (da)

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
DK1056736T3 true DK1056736T3 (da)	2002-12-30

Family

ID=21745026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK99904208T DK1056736T3 (da)	1998-01-21	1999-01-21	Alternativ fremgangsmåde til acylering af 10-deacetylbaccatin III selektivt i C-10-stillingen

Country Status (20)

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

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
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
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
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
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
BRPI0511109A (pt) *	2004-05-14	2007-11-27	Immunogen Inc	método fácil para sintetizar compostos de baccatin iii

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

Also Published As

Publication number	Publication date
DE69902757T2 (de)	2003-01-09
GEP20022800B (en)	2002-09-25
JP2002501060A (ja)	2002-01-15
WO1999037632A1 (en)	1999-07-29
IL136043A0 (en)	2001-05-20
PT1056736E (pt)	2002-12-31
EP1056736B1 (en)	2002-09-04
EA200000782A1 (ru)	2000-12-25
CA2312350A1 (en)	1999-07-29
EA002576B1 (ru)	2002-06-27
NO20002923D0 (no)	2000-06-08
CN1288463A (zh)	2001-03-21
ATE223394T1 (de)	2002-09-15
NZ505117A (en)	2002-11-26
AU2465799A (en)	1999-08-09
AU741516B2 (en)	2001-12-06
TR200001821T2 (tr)	2001-01-22
ES2182484T3 (es)	2003-03-01
NO20002923L (no)	2000-09-11
US5914411A (en)	1999-06-22
EP1056736A4 (en)	2001-04-11
KR20010034082A (ko)	2001-04-25
EP1056736A1 (en)	2000-12-06
DE69902757D1 (de)	2002-10-10
BR9907160A (pt)	2000-10-24

Publication	Publication Date	Title
NO951281D0 (no)	1995-04-03	Fremgangsmåte for fremstilling av 10-desacetyl-baccatin-III
DK1056736T3 (da)	2002-12-30	Alternativ fremgangsmåde til acylering af 10-deacetylbaccatin III selektivt i C-10-stillingen
EA199900096A1 (ru)	1999-08-26	Способ ацилирования 10-деацетилбаккатина iii селективно в положение с-10
Vorbrueggen	2008	The conversion of primary or secondary alcohols with nonaflyl fluoride into their corresponding inverted fluorides
EA199801068A1 (ru)	2000-06-26	Способ получения доцетаксела
BR0015411A (pt)	2002-06-25	Método de preparo de cefpodoxima proxetil altamente pura
EP1497276B1 (en)	2008-08-20	Conversion of taxane molecules
Andres et al.	1995	Non-metallocatalyzed epoxidation of chiral unsaturated lactams by tertiary amine N-oxides
Mandai et al.	2000	A semisynthesis of paclitaxel via a 10-deacetylbaccatin III derivative bearing a β-keto ester appendage
Oba et al.	2005	Facile Synthesis of 3‐Hydroxyglutamic Acids via Cyanation of Chiral N‐Acyliminium Cation Derived From (S)‐Malic Acid
KR920002520A (ko)	1992-02-28	살균제
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
KR910015557A (ko)	1991-09-30	2-아미노-3,5-디니트로 티오펜의 제조방법
CN103145572A (zh)	2013-06-12	天然产物氯化γ-正缬氨酸盐酸盐的不对称合成方法
KR960010652A (ko)	1996-04-20	결정성 토실산 썰타미실린 2수화물의 제조방법