ES2161716T3 - Procedimiento e intermedios para la sintesis asimetrica de camptotecina y de sus analogos. - Google Patents

Procedimiento e intermedios para la sintesis asimetrica de camptotecina y de sus analogos.

Info

Publication number
ES2161716T3
ES2161716T3 ES93910758T ES93910758T ES2161716T3 ES 2161716 T3 ES2161716 T3 ES 2161716T3 ES 93910758 T ES93910758 T ES 93910758T ES 93910758 T ES93910758 T ES 93910758T ES 2161716 T3 ES2161716 T3 ES 2161716T3
Authority
ES
Spain
Prior art keywords
alkyl
analogs
camptotecina
intermediates
procedure
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 - Lifetime
Application number
ES93910758T
Other languages
English (en)
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 ES2161716T3 publication Critical patent/ES2161716T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

SE DESCRIBEN PROCESOS PARA OBTENER COMPUESTOS DE FORMULA (XIV), (XV) Y (XVII), DONDE R6 ALQUILO DE BAJO NUMERO DE CARBONOS, R7 BAJO NUMERO DE CARBONOS, R ALQUILO DE BAJO NUMERO DE CARBONOS, Y ES H, F O CL, R8 ES UN RADICAL DE ALQUILO DE C1-4 DONDE N ES 1, 2 O 3, R11 ALQUILO DE C1-4 Y R12 ES IDENTICO A R11 O R11 Y R12 CONJUNTAMENTE FORMAN CICLOPENTANO O CICLOHEXANO Y R13 ES (A) FENILO SUBSTITUIDO UNA A CINCO VECES CON ALQUILO SECUNDARIO DE C3 A 7 O ALQUILO TERCIARIO DE C4 A 7 O (B) SELECCIONADO DEL GRUPO CONSISTENTE EN NAFTILO, ANTIRILO Y FENANTILO SUBSTITUIDO OPCIONALMENTE UNA A CINCO VECES CON GRUPOS ALQUILO SECUNDARIO DE C3 A 7 O GRUPOS ALQUILO TERCIARIO C4 A 7, R10 ALQUILO DE C 6 A 10 ARILO ALQUILARILO E Y H, F O CL. ESTOS PROCESOS SE UTILIZAN PARA OBTENER COMPUESTOS CON FORMAS PURAS OPTICAS Y CON PROPIEDADES OPTICAS AUMENTADAS Y DICHOS COMPUESTOS SE EMPLEAN EN LA OBTENCION DE UNA COMPOTECINA Y ANALOGOS DE LA MISMA.
ES93910758T 1992-06-18 1993-04-23 Procedimiento e intermedios para la sintesis asimetrica de camptotecina y de sus analogos. Expired - Lifetime ES2161716T3 (es)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
ES2161716T3 true ES2161716T3 (es) 2001-12-16

Family

ID=25412873

Family Applications (1)

Application Number Title Priority Date Filing Date
ES93910758T Expired - Lifetime ES2161716T3 (es) 1992-06-18 1993-04-23 Procedimiento e intermedios para la sintesis asimetrica de camptotecina y de sus analogos.

Country Status (12)

Country Link
US (1) US5212317A (es)
EP (2) EP0646117B1 (es)
JP (1) JP3499554B2 (es)
AT (1) ATE203538T1 (es)
AU (1) AU4114293A (es)
DE (1) DE69330496T2 (es)
DK (1) DK0646117T3 (es)
ES (1) ES2161716T3 (es)
GR (1) GR3036890T3 (es)
HU (1) HUT71411A (es)
PT (1) PT646117E (es)
WO (1) WO1993025556A1 (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5459269A (en) * 1992-06-18 1995-10-17 North Carolina State University 14-halo-camptothecins
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
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
EP0835303A4 (en) * 1995-06-07 2000-09-13 Univ Jefferson ANTIFUNGAL AGENTS AND THEIR IDENTIFICATION AND UTILIZATION METHODS
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
FI80022C (fi) * 1982-07-05 1990-04-10 Otsuka Pharma Co Ltd Foerfarande foer framstaellning av ett nytt, terapeutiskt anvaendbart karbostyrilderivat.
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
GR3036890T3 (en) 2002-01-31
DE69330496D1 (de) 2001-08-30
EP1020468A2 (en) 2000-07-19
EP1020468A3 (en) 2000-07-26
ATE203538T1 (de) 2001-08-15
AU4114293A (en) 1994-01-04
EP0646117B1 (en) 2001-07-25
DK0646117T3 (da) 2001-11-12
HU9403638D0 (en) 1995-02-28
US5212317A (en) 1993-05-18
WO1993025556A1 (en) 1993-12-23
EP0646117A1 (en) 1995-04-05
JPH07507795A (ja) 1995-08-31
DE69330496T2 (de) 2002-05-29
HUT71411A (en) 1995-11-28
EP0646117A4 (en) 1995-11-15
PT646117E (pt) 2002-01-30
JP3499554B2 (ja) 2004-02-23

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