DE69330496D1 - Verfahren und zwischenprodukte zur asymmetrischen synthese von camptothecin und camptothecin-analogen - Google Patents

Verfahren und zwischenprodukte zur asymmetrischen synthese von camptothecin und camptothecin-analogen

Info

Publication number
DE69330496D1
DE69330496D1 DE69330496T DE69330496T DE69330496D1 DE 69330496 D1 DE69330496 D1 DE 69330496D1 DE 69330496 T DE69330496 T DE 69330496T DE 69330496 T DE69330496 T DE 69330496T DE 69330496 D1 DE69330496 D1 DE 69330496D1
Authority
DE
Germany
Prior art keywords
alkyl
camptothecin
analogs
intermediate products
chem
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.)
Expired - Fee Related
Application number
DE69330496T
Other languages
English (en)
Other versions
DE69330496T2 (de
Inventor
Daniel L Comins
Matthew F Baevsky
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.)
North Carolina State University
University of California
Original Assignee
North Carolina State University
University of California
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
Application filed by North Carolina State University, University of California filed Critical North Carolina State University
Application granted granted Critical
Publication of DE69330496D1 publication Critical patent/DE69330496D1/de
Publication of DE69330496T2 publication Critical patent/DE69330496T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
DE69330496T 1992-06-18 1993-04-23 Verfahren und zwischenprodukte zur asymmetrischen synthese von camptothecin und camptothecin-analogen Expired - Fee Related DE69330496T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/900,650 US5212317A (en) 1990-12-20 1992-06-18 Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs
PCT/US1993/003839 WO1993025556A1 (en) 1992-06-18 1993-04-23 Methods and intermediates for the asymmetric synthesis of camptothecin and camptothecin analogs

Publications (2)

Publication Number Publication Date
DE69330496D1 true DE69330496D1 (de) 2001-08-30
DE69330496T2 DE69330496T2 (de) 2002-05-29

Family

ID=25412873

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69330496T Expired - Fee Related DE69330496T2 (de) 1992-06-18 1993-04-23 Verfahren und zwischenprodukte zur asymmetrischen synthese von camptothecin und camptothecin-analogen

Country Status (12)

Country Link
US (1) US5212317A (de)
EP (2) EP1020468A3 (de)
JP (1) JP3499554B2 (de)
AT (1) ATE203538T1 (de)
AU (1) AU4114293A (de)
DE (1) DE69330496T2 (de)
DK (1) DK0646117T3 (de)
ES (1) ES2161716T3 (de)
GR (1) GR3036890T3 (de)
HU (1) HUT71411A (de)
PT (1) PT646117E (de)
WO (1) WO1993025556A1 (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5428166A (en) * 1992-06-18 1995-06-27 North Carolina State University Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs
US5459269A (en) * 1992-06-18 1995-10-17 North Carolina State University 14-halo-camptothecins
US5475108A (en) * 1993-08-31 1995-12-12 North Carolina State University Camptothecin intermediates and method of making camptothecin and comptothecin analogs
US5395939A (en) * 1993-11-30 1995-03-07 North Carolina State University Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs
US5491237A (en) * 1994-05-03 1996-02-13 Glaxo Wellcome Inc. Intermediates in pharmaceutical camptothecin preparation
US5496952A (en) * 1995-02-07 1996-03-05 North Carolina State University Method of making asymmetric DE ring intermediates for the synthesis of camptothecin and camptothecin analogs
WO1996040886A1 (en) * 1995-06-07 1996-12-19 Thomas Jefferson University Anti-fungal agents and methods of identifying and using the same
US6716982B2 (en) 1995-11-02 2004-04-06 Osi Pharmaceuticals, Inc. Method for preparing camptothecin derivatives
US6559309B2 (en) 1996-11-01 2003-05-06 Osi Pharmaceuticals, Inc. Preparation of a camptothecin derivative by intramolecular cyclisation

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3109018A (en) * 1961-06-15 1963-10-29 Chemetron Corp Resolution of dl-menthol
US3607651A (en) * 1968-12-11 1971-09-21 Takasago Perfumery Co Ltd Method for the biochemical isolation of l-menthol
US3943181A (en) * 1971-02-27 1976-03-09 Haarmann & Reimer Gesellschaft Mit Beschrankter Haftung Separating optically pure d-l-isomers of menthol, neomenthol and isomenthol
JPS5251095A (en) * 1975-10-22 1977-04-23 Meito Sangyo Kk Preparation f menthol rich in -menthol from racemic menthol
JPS54101487A (en) * 1978-01-25 1979-08-10 Nippon Terpen Kagaku Kk Optical splitting of racemic menthol and isopregol
US4418225A (en) * 1982-01-08 1983-11-29 Uop Inc. Resolution of d,1-menthol
US4578381A (en) * 1982-07-05 1986-03-25 Otsuka Pharmaceutical Co., Ltd. Carbostyril derivatives
DE3511210A1 (de) * 1985-03-28 1986-10-02 Bayer Ag, 5090 Leverkusen Verfahren zur inversion der konfiguration sekundaerer alkohole
US4916074A (en) * 1986-10-30 1990-04-10 Chisso Corporation Process for producing optically active compounds
US5032523A (en) * 1987-01-14 1991-07-16 Lion Corporation Preparation of optically active esters
US4894456A (en) * 1987-03-31 1990-01-16 Research Triangle Institute Synthesis of camptothecin and analogs thereof
JP2707076B2 (ja) * 1987-05-01 1998-01-28 チッソ株式会社 光学活性化合物の製造法
DE3737335A1 (de) * 1987-11-04 1989-05-18 Basf Ag Verfahren zur herstellung eines biokatalysators und dessen verwendung zur razematspaltung
DE3743824C2 (de) * 1987-12-23 1997-03-06 Hoechst Ag Verfahren zur enzymatischen Racematspaltung von racemischen Alkoholen mit/in Vinylestern durch Umesterung
US4996158A (en) * 1987-12-26 1991-02-26 Junichi Oda Optical resolution of racemic alcohols
JPH01235599A (ja) * 1988-03-16 1989-09-20 Lion Corp ラセミアルコールの光学分割法
JPH0615547B2 (ja) * 1988-01-20 1994-03-02 株式会社ヤクルト本社 新規なカンプトテシン誘導体
US5057427A (en) * 1988-04-07 1991-10-15 Sepracor, Inc. Method for resolution of stereoisomers
US5162532A (en) * 1990-12-20 1992-11-10 North Carolina State University Intermediates and method of making camptothecin and camptothecin analogs

Also Published As

Publication number Publication date
ES2161716T3 (es) 2001-12-16
PT646117E (pt) 2002-01-30
EP0646117B1 (de) 2001-07-25
EP1020468A2 (de) 2000-07-19
DE69330496T2 (de) 2002-05-29
US5212317A (en) 1993-05-18
WO1993025556A1 (en) 1993-12-23
HUT71411A (en) 1995-11-28
AU4114293A (en) 1994-01-04
EP1020468A3 (de) 2000-07-26
HU9403638D0 (en) 1995-02-28
EP0646117A1 (de) 1995-04-05
JPH07507795A (ja) 1995-08-31
DK0646117T3 (da) 2001-11-12
ATE203538T1 (de) 2001-08-15
GR3036890T3 (en) 2002-01-31
JP3499554B2 (ja) 2004-02-23
EP0646117A4 (de) 1995-11-15

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Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee