ES484181A1 - Un procedimiento para la preparacion de hidroxi-9-elipticina - Google Patents

Un procedimiento para la preparacion de hidroxi-9-elipticina

Info

Publication number
ES484181A1
ES484181A1 ES484181A ES484181A ES484181A1 ES 484181 A1 ES484181 A1 ES 484181A1 ES 484181 A ES484181 A ES 484181A ES 484181 A ES484181 A ES 484181A ES 484181 A1 ES484181 A1 ES 484181A1
Authority
ES
Spain
Prior art keywords
derivatives
hydroxy
group
condensation
ellipticin
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
Application number
ES484181A
Other languages
English (en)
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.)
Labaz SA
Bpifrance Financement SA
Original Assignee
Agence National de Valorisation de la Recherche ANVAR
Labaz SA
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 Agence National de Valorisation de la Recherche ANVAR, Labaz SA filed Critical Agence National de Valorisation de la Recherche ANVAR
Publication of ES484181A1 publication Critical patent/ES484181A1/es
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

1.Un procedimiento para la preparación de hidroxi-9- elipticina, así como de derivados de ésta, sustituidos en las posiciones 6 y/ó 9 y/o cuaternizados en el átomo de nitrógeno de la posición 2, caracterizado por el hecho de que : 1) se condensa metoxi-5-indol con hexano-diona-2,5 para preparar metoxi-6-dimetil-1,4-carbazol; 2) se desmetila este metoxi-6- dimetil-1,4-carbazol para preparar el hidroxi-6-dimetil-1,4- carbazol; 3) se protege el grupo hidroxi de éste último por bencilación o por benzoilación del hidroxi-6-dimetil-1,4- carbazol; 4) se efectúa si se desea una metalación del bencil ( o benzoil)-oxi-6-dimetil-1,4-carbazol así preparado, y se trata el producto de esta metalación con yoduro de alcohilo para preparar el alcohil-9-bencil (o benzoil)-oxi-6-dimetil- 1,4-carbazol; 5) se formila el producto de la etapa 3) ó 4) para preparar el formil-3-bencil (o benzoil)-oxi-6-dimetil- 1,4-carbazol, o el formil-3-alcohil-9-bencil(o benzoil)-oxi.6- dimetil-1,4-carbazol; 6) se condensa éstecon el dimetil- acetal del aminoacetaldehido para preparar el (Beta, Beta- dimetoxi-etil-iminometil)-3-alcohil-9-bencil (o benzoil)-oxi- 6-dimetil-1,4-carbazol, o en homólogo alcohilado en la posición 9; 7) se ciclisa el producto de la etapa 6), y 8) se saponifica la benzoil-oxi-9-elipticina o la benzoil-oxi-9- alcohil-6-elipticina o se somete a una hidrogenolisis la benciloxi-9-elipticina o la benciloxi-9-alcohil-6- elipticina correspondiente, y, si se desea, 9) se trata el producto de la etapa 8) con un halogenuro de hidroxi-9-alcohil-2-elipticinio, o el halogenuro de hidroxi-9-dialcohil-2,6-elipticinio correpondiente, y eventualmente, 10) se convierte el hologenuro de elipticinio sustituido obtenido en la etapa 9) en una sal hidrosoluble correspondiente cuaternizada en el átamo de nitrógeno de la posición 2.
ES484181A 1978-09-15 1979-09-14 Un procedimiento para la preparacion de hidroxi-9-elipticina Expired ES484181A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/942,793 US4310667A (en) 1976-04-22 1978-09-15 2-N Quaternary ammonium salt derivatives of 9-hydroxy ellipticine

Publications (1)

Publication Number Publication Date
ES484181A1 true ES484181A1 (es) 1980-05-16

Family

ID=25478610

Family Applications (1)

Application Number Title Priority Date Filing Date
ES484181A Expired ES484181A1 (es) 1978-09-15 1979-09-14 Un procedimiento para la preparacion de hidroxi-9-elipticina

Country Status (9)

Country Link
US (1) US4310667A (es)
EP (1) EP0009445B1 (es)
JP (2) JPS5951956B2 (es)
AT (1) ATE3427T1 (es)
DE (1) DE2965444D1 (es)
ES (1) ES484181A1 (es)
HU (1) HU183081B (es)
SU (1) SU1053753A3 (es)
WO (1) WO1980000564A1 (es)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6137799A (ja) * 1984-07-31 1986-02-22 Suntory Ltd エリプチシン誘導体およびその製造法
FR2584409B1 (fr) * 1985-07-04 1987-11-20 Sanofi Sa Chlorhydrates de chlorures de derives d'aminoalkyl-2 hydroxy-9 ellipticinium et compositions pharmaceutiques en contenant
US4851417A (en) * 1988-05-26 1989-07-25 Rensselaer Polytechnic Institute 9-substituted 6H-pyrido[4,3-b]carbazoles
JPH02121545U (es) * 1989-03-17 1990-10-03
KR950002885B1 (ko) * 1990-06-05 1995-03-28 토레이가부시키가이샤 인돌 유도체
US5272146A (en) * 1992-10-02 1993-12-21 The United States Of America As Represented By The United States Department Of Health And Human Services 1,2-dihydroellipticines with activity against CNS specific cancer cell lines
AU666416B2 (en) * 1993-01-29 1996-02-08 Tanabe Seiyaku Co., Ltd. Ellipticine derivative and process for preparing the same
US5424315A (en) * 1993-08-02 1995-06-13 Sri International Benzothiophen analogs as antiviral agents
JPH0861498A (ja) * 1995-08-29 1996-03-08 S T K Shokai:Kk 油圧シリンダ
JP4299375B2 (ja) 1996-05-31 2009-07-22 積水化学工業株式会社 発泡性熱可塑性樹脂シート状体、熱可塑性樹脂発泡体、及びそれらの製造方法
WO1997046559A1 (en) * 1996-06-04 1997-12-11 Tanabe Seiyaku Co., Ltd. Process for preparing 9-hydroxyellipticine
CA2247314A1 (en) 1996-12-26 1998-07-09 Tomoyuki Kobayashi Foamable thermoplastic sheet-like synthetic resin, thermoplastic foamed resin and their production method
US20070027175A1 (en) * 2005-07-27 2007-02-01 Shaughnessy John Jr Antineoplastic activities of ellipticine and its derivatives
JP2009537626A (ja) * 2006-05-22 2009-10-29 ビオアリアンス ファルマ ９−ヒドロキシエリプチシン誘導体による悪性表現型の復帰変異
PL2508207T3 (pl) 2011-03-31 2013-09-30 Bioalliance Pharma Nanocząsteczki zawierające chemioterapeutyczny lek przeciwnowotworowy
WO2014036395A1 (en) * 2012-08-30 2014-03-06 The Scripps Research Institute SMALL MOLECULES TARGETING REPEAT r(CGG) SEQUENCES

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2248828B1 (es) * 1973-10-29 1977-04-15 Anvar
US3933827A (en) * 1974-10-29 1976-01-20 Hoffmann-La Roche Inc. 9-Acyloxy-5,11-dimethyl-6H-pyrido[4,3-B]carbazoles
FR2308365A2 (fr) * 1975-04-25 1976-11-19 Anvar Derives de l'hydroxy-9 ellipticine et leur application therapeutique

Also Published As

Publication number Publication date
JPS6141917B2 (es) 1986-09-18
JPS5951956B2 (ja) 1984-12-17
HU183081B (en) 1984-04-28
SU1053753A3 (ru) 1983-11-07
EP0009445B1 (fr) 1983-05-18
WO1980000564A1 (fr) 1980-04-03
JPS55500630A (es) 1980-09-11
US4310667A (en) 1982-01-12
ATE3427T1 (de) 1983-06-15
EP0009445A1 (fr) 1980-04-02
JPS6045579A (ja) 1985-03-12
DE2965444D1 (en) 1983-07-07

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19970401