CA2347588A1 - An oxazinone used in preparing taxol and process for preparation thereof - Google Patents

An oxazinone used in preparing taxol and process for preparation thereof

Info

Publication number
CA2347588A1
CA2347588A1 CA002347588A CA2347588A CA2347588A1 CA 2347588 A1 CA2347588 A1 CA 2347588A1 CA 002347588 A CA002347588 A CA 002347588A CA 2347588 A CA2347588 A CA 2347588A CA 2347588 A1 CA2347588 A1 CA 2347588A1
Authority
CA
Canada
Prior art keywords
oxazinone
preparation
heteroaryl
alkynyl
aryl
Prior art date
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.)
Granted
Application number
CA002347588A
Other languages
French (fr)
Other versions
CA2347588C (en
Inventor
Robert A. Holton
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.)
Florida State University
Original Assignee
Florida State University
Robert A. Holton
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.)
Filing date
Publication date
Priority claimed from US07/436,235 external-priority patent/US5015744A/en
Application filed by Florida State University, Robert A. Holton filed Critical Florida State University
Publication of CA2347588A1 publication Critical patent/CA2347588A1/en
Application granted granted Critical
Publication of CA2347588C publication Critical patent/CA2347588C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/76—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members
    • C07C2603/84—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing rings with more than eight members
    • 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

Abstract

Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula:
CA002347588A 1989-11-14 1990-11-13 An oxazinone used in preparing taxol and process for preparation thereof Expired - Fee Related CA2347588C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US07/436,235 1989-11-14
US07/436,235 US5015744A (en) 1989-11-14 1989-11-14 Method for preparation of taxol using an oxazinone
US07/603,041 1990-10-30
US07/603,041 US5136060A (en) 1989-11-14 1990-10-30 Method for preparation of taxol using an oxazinone
CA002029787A CA2029787C (en) 1989-11-14 1990-11-13 Method for preparation of taxol using an oxazinone

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002029787A Division CA2029787C (en) 1989-11-14 1990-11-13 Method for preparation of taxol using an oxazinone

Publications (2)

Publication Number Publication Date
CA2347588A1 true CA2347588A1 (en) 1991-05-15
CA2347588C CA2347588C (en) 2005-08-16

Family

ID=27030868

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002029787A Expired - Fee Related CA2029787C (en) 1989-11-14 1990-11-13 Method for preparation of taxol using an oxazinone
CA002347588A Expired - Fee Related CA2347588C (en) 1989-11-14 1990-11-13 An oxazinone used in preparing taxol and process for preparation thereof

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA002029787A Expired - Fee Related CA2029787C (en) 1989-11-14 1990-11-13 Method for preparation of taxol using an oxazinone

Country Status (28)

Country Link
US (3) US5136060A (en)
EP (1) EP0428376B1 (en)
JP (1) JP2507830B2 (en)
KR (1) KR0161499B1 (en)
CN (1) CN1043528C (en)
AT (1) ATE132860T1 (en)
AU (1) AU633375B2 (en)
BG (1) BG60478B1 (en)
CA (2) CA2029787C (en)
CZ (2) CZ283581B6 (en)
DE (1) DE69024757T2 (en)
DK (1) DK0428376T3 (en)
EG (1) EG19641A (en)
ES (1) ES2083438T3 (en)
FI (1) FI104487B (en)
GR (1) GR3019192T3 (en)
HU (1) HU209299B (en)
IE (2) IE76279B1 (en)
IL (3) IL96304A (en)
MY (1) MY106071A (en)
NO (1) NO177902C (en)
NZ (1) NZ235993A (en)
OA (1) OA09327A (en)
PL (1) PL167898B1 (en)
PT (1) PT95870B (en)
RO (1) RO110491B1 (en)
RU (1) RU2033994C1 (en)
YU (1) YU48232B (en)

Families Citing this family (101)

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US5175315A (en) * 1989-05-31 1992-12-29 Florida State University Method for preparation of taxol using β-lactam
MY110249A (en) * 1989-05-31 1998-03-31 Univ Florida State Method for preparation of taxol using beta lactam
US5136060A (en) * 1989-11-14 1992-08-04 Florida State University Method for preparation of taxol using an oxazinone
US5475120A (en) * 1990-11-02 1995-12-12 University Of Florida Method for the isolation and purification of taxol and its natural analogues
US5380916A (en) * 1990-11-02 1995-01-10 University Of Florida Method for the isolation and purification of taxane derivatives
CA2071160A1 (en) * 1991-07-31 1993-02-01 Vittorio Farina Asymmetric synthesis of taxol side chain
US6011056A (en) 1991-09-23 2000-01-04 Florida State University C9 taxane derivatives and pharmaceutical compositions containing them
US5284864A (en) 1991-09-23 1994-02-08 Florida State University Butenyl substituted taxanes and pharmaceutical compositions containing them
US5283253A (en) * 1991-09-23 1994-02-01 Florida State University Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
US6335362B1 (en) * 1991-09-23 2002-01-01 Florida State University Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them
US5739362A (en) * 1991-09-23 1998-04-14 Florida State University Taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US5274124A (en) * 1991-09-23 1993-12-28 Florida State University Metal alkoxides
US6028205A (en) * 1991-09-23 2000-02-22 Florida State University C2 tricyclic taxanes
US5710287A (en) * 1991-09-23 1998-01-20 Florida State University Taxanes having an amino substituted side-chain and pharmaceutical compositions containing them
US5714513A (en) * 1991-09-23 1998-02-03 Florida State University C10 taxane derivatives and pharmaceutical compositions
US5728850A (en) * 1991-09-23 1998-03-17 Florida State University Taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
DE69233672T2 (en) * 1991-09-23 2007-10-18 Florida State University, Tallahassee Beta-lactams useful for the preparation of substituted isoserine esters with metal alkoxides
US5721268A (en) 1991-09-23 1998-02-24 Florida State University C7 taxane derivatives and pharmaceutical compositions containing them
US5998656A (en) * 1991-09-23 1999-12-07 Florida State University C10 tricyclic taxanes
US5489601A (en) * 1991-09-23 1996-02-06 Florida State University Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them
US7074945B2 (en) * 1991-09-23 2006-07-11 Florida State University Metal alkoxide taxane derivatives
US5728725A (en) * 1991-09-23 1998-03-17 Florida State University C2 taxane derivaties and pharmaceutical compositions containing them
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US5430160A (en) * 1991-09-23 1995-07-04 Florida State University Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides
US6018073A (en) * 1991-09-23 2000-01-25 Florida State University Tricyclic taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US6521660B2 (en) 1991-09-23 2003-02-18 Florida State University 3′-alkyl substituted taxanes and pharmaceutical compositions containing them
US6794523B2 (en) 1991-09-23 2004-09-21 Florida State University Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
US6005138A (en) * 1991-09-23 1999-12-21 Florida State University Tricyclic taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US6495704B1 (en) 1991-09-23 2002-12-17 Florida State University 9-desoxotaxanes and process for the preparation of 9-desoxotaxanes
US5654447A (en) * 1991-09-23 1997-08-05 Florida State University Process for the preparation of 10-desacetoxybaccatin III
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Also Published As

Publication number Publication date
DK0428376T3 (en) 1996-02-05
YU48232B (en) 1997-08-22
ATE132860T1 (en) 1996-01-15
CN1053427A (en) 1991-07-31
PT95870B (en) 1997-04-30
PT95870A (en) 1991-09-30
NO177902B (en) 1995-09-04
CZ313695A3 (en) 1997-11-12
JP2507830B2 (en) 1996-06-19
IL96304A0 (en) 1991-08-16
RU2033994C1 (en) 1995-04-30
CZ283581B6 (en) 1998-05-13
CA2029787A1 (en) 1991-05-15
MY106071A (en) 1995-03-31
CZ283539B6 (en) 1998-04-15
YU216090A (en) 1993-10-20
US5136060A (en) 1992-08-04
DE69024757T2 (en) 1996-05-15
PL287757A1 (en) 1991-12-16
NZ235993A (en) 1992-10-28
IE74154B1 (en) 1997-07-02
BG60478B1 (en) 1995-05-31
US5532363A (en) 1996-07-02
AU6590490A (en) 1991-05-23
EP0428376A1 (en) 1991-05-22
FI104487B (en) 2000-02-15
RO110491B1 (en) 1996-01-30
NO904923L (en) 1991-05-15
OA09327A (en) 1992-09-15
CA2347588C (en) 2005-08-16
IE904061A1 (en) 1991-05-22
KR0161499B1 (en) 1998-12-01
GR3019192T3 (en) 1996-06-30
HUT57200A (en) 1991-11-28
HU209299B (en) 1994-04-28
PL167898B1 (en) 1995-12-30
CA2029787C (en) 2001-10-09
EG19641A (en) 1995-08-30
EP0428376B1 (en) 1996-01-10
IL96304A (en) 1995-06-29
CZ563490A3 (en) 1998-01-14
NO904923D0 (en) 1990-11-13
KR910009681A (en) 1991-06-28
NO177902C (en) 1995-12-13
FI905609A0 (en) 1990-11-13
IL109246A0 (en) 1994-07-31
CN1043528C (en) 1999-06-02
ES2083438T3 (en) 1996-04-16
IE76279B1 (en) 1997-10-08
US5384399A (en) 1995-01-24
DE69024757D1 (en) 1996-02-22
HU907131D0 (en) 1991-05-28
JPH03232869A (en) 1991-10-16
IL109246A (en) 1998-01-04
AU633375B2 (en) 1993-01-28

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