CA2083534C - Indolopyrrolocarbazole derivatives - Google Patents

Indolopyrrolocarbazole derivatives Download PDF

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Publication number
CA2083534C
CA2083534C CA002083534A CA2083534A CA2083534C CA 2083534 C CA2083534 C CA 2083534C CA 002083534 A CA002083534 A CA 002083534A CA 2083534 A CA2083534 A CA 2083534A CA 2083534 C CA2083534 C CA 2083534C
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CA
Canada
Prior art keywords
group
groups
compound
formula
lower alkyl
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
CA002083534A
Other languages
English (en)
French (fr)
Other versions
CA2083534A1 (en
Inventor
Katsuhisa Kojiri
Hisao Kondo
Hiroharu Arakawa
Mitsuru Ohkubo
Hiroyuki Suda
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.)
MSD KK
Original Assignee
Banyu Phamaceutical Co Ltd
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 Banyu Phamaceutical Co Ltd filed Critical Banyu Phamaceutical Co Ltd
Publication of CA2083534A1 publication Critical patent/CA2083534A1/en
Application granted granted Critical
Publication of CA2083534C publication Critical patent/CA2083534C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/044—Pyrrole radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Genetics & Genomics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Silicon Polymers (AREA)
CA002083534A 1991-11-29 1992-11-23 Indolopyrrolocarbazole derivatives Expired - Fee Related CA2083534C (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP341,916/91 1991-11-29
JP34191691 1991-11-29
JP6926992 1992-02-18
JP69,269,92 1992-02-18
JP257,306/92 1992-09-01
JP25730692 1992-09-01

Publications (2)

Publication Number Publication Date
CA2083534A1 CA2083534A1 (en) 1993-05-30
CA2083534C true CA2083534C (en) 2003-01-28

Family

ID=27300000

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002083534A Expired - Fee Related CA2083534C (en) 1991-11-29 1992-11-23 Indolopyrrolocarbazole derivatives

Country Status (27)

Country Link
EP (1) EP0545195B1 (OSRAM)
JP (1) JP2629542B2 (OSRAM)
KR (1) KR100275976B1 (OSRAM)
AT (1) ATE130617T1 (OSRAM)
AU (1) AU650376B2 (OSRAM)
BG (1) BG61036B1 (OSRAM)
CA (1) CA2083534C (OSRAM)
CZ (1) CZ287304B6 (OSRAM)
DE (1) DE69206242T2 (OSRAM)
DK (1) DK0545195T3 (OSRAM)
DZ (1) DZ1634A1 (OSRAM)
ES (1) ES2079774T3 (OSRAM)
FI (1) FI106864B (OSRAM)
GR (1) GR3018527T3 (OSRAM)
HU (3) HU9203754D0 (OSRAM)
IL (1) IL103844A (OSRAM)
MX (1) MX9206847A (OSRAM)
MY (1) MY114655A (OSRAM)
NO (1) NO178929C (OSRAM)
NZ (1) NZ245203A (OSRAM)
PL (1) PL171468B1 (OSRAM)
RO (1) RO113469B1 (OSRAM)
RU (1) RU2117671C1 (OSRAM)
SA (1) SA93130351B1 (OSRAM)
TW (1) TW224469B (OSRAM)
WO (1) WO1993011145A1 (OSRAM)
YU (1) YU48963B (OSRAM)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995030682A1 (en) * 1994-05-09 1995-11-16 Banyu Pharmaceutical Co., Ltd. Antitumor indolopyprolocarbazole derivative
PT760375E (pt) * 1994-05-09 2004-04-30 Banyu Pharma Co Ltd Derivado de indolopiprolocarbazole anti-tumoral
ES2206506T3 (es) * 1994-06-13 2004-05-16 Banyu Pharmaceutical Co., Ltd. Gen que codifica glicosil-transferasa, y su utilizacion.
AU3086495A (en) * 1994-08-02 1996-03-04 Banyu Pharmaceutical Co., Ltd. Antitumor indolopyrrolocarbazoles
US5475110A (en) * 1994-10-14 1995-12-12 Cephalon, Inc. Fused Pyrrolocarbazoles
US5591855A (en) * 1994-10-14 1997-01-07 Cephalon, Inc. Fused pyrrolocarbazoles
US5705511A (en) * 1994-10-14 1998-01-06 Cephalon, Inc. Fused pyrrolocarbazoles
US5594009A (en) * 1994-10-14 1997-01-14 Cephalon, Inc. Fused pyrrolocarbazoles
AU6836696A (en) * 1995-09-05 1997-03-27 Banyu Pharmaceutical Co., Ltd. Antitumor indolopyrrolocarbazole derivatives
US5616724A (en) * 1996-02-21 1997-04-01 Cephalon, Inc. Fused pyrrolo[2,3-c]carbazole-6-ones
ES2169414T3 (es) * 1996-08-22 2002-07-01 Bristol Myers Squibb Co Amino-azucar citotoxico y derivados de azucares relacionados de indolopirrolocarbazoles.
GB9811624D0 (en) * 1998-05-29 1998-07-29 Merck Sharp & Dohme Therapeutic use
US6013646A (en) * 1998-07-02 2000-01-11 Bayer Corporation Indolocarbazole derivatives useful for the treatment of neurodegenerative diseases and cancer
US6858598B1 (en) 1998-12-23 2005-02-22 G. D. Searle & Co. Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US6833373B1 (en) 1998-12-23 2004-12-21 G.D. Searle & Co. Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US6703373B1 (en) 1999-09-10 2004-03-09 Banyu Pharmaceutical Co., Ltd. Indolopyrrolocarbazole derivatives and antitumor agents
FR2801054B1 (fr) * 1999-11-17 2003-06-13 Adir Nouveaux derives de 12,13-(pyranosyl)-indolo[2,3-a]pyrrolo [3,4-c]carbazole et 12,13-(pyranosyl)-furo[3,4-c]indolo [2,3-a]carbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
DK1258490T3 (da) 2000-02-24 2004-04-05 Banyu Pharma Co Ltd Fremgangsmåde til fremstilling af indolopyrrolocarbazol, mellemprodukter dertil og fremgangsmåde til fremstillingen af mellemprodukterne
US6653290B2 (en) 2000-10-06 2003-11-25 Bristol-Myers Squibb Company Tumor proliferation inhibitors
US6677450B2 (en) 2000-10-06 2004-01-13 Bristol-Myers Squibb Company Topoisomerase inhibitors
US6610727B2 (en) 2000-10-06 2003-08-26 Bristol-Myers Squibb Company Anhydro sugar derivatives of indolocarbazoles
US6555677B2 (en) 2000-10-31 2003-04-29 Merck & Co., Inc. Phase transfer catalyzed glycosidation of an indolocarbazole
MXPA03008589A (es) 2001-03-22 2003-12-08 Bristol Myers Squibb Co Derivados de azucar citotoxicos selectivos de topoisomerasa i de indolopirrolocarbazoles.
US6559299B2 (en) 2001-03-29 2003-05-06 Merck & Co., Inc. Preparation and isolation of indolocarbazole glycosides
US20050171036A1 (en) * 2002-03-26 2005-08-04 Banyu Pharmaceutical Co., Ltd. Use of antitumor indolopyrrolocarbazole derivative and other anticancer agent in combination
CA2398828A1 (en) 2002-08-09 2004-02-09 Merck & Co., Inc. A pharmaceutical composition containing an indolopyrrolocarbazole derivative
AU2003261708A1 (en) * 2002-08-23 2004-03-11 Banyu Pharmaceutical Co., Ltd. Process for producing indolopyrrolocarbazole derivative
AU2003248103A1 (en) * 2003-07-24 2005-02-14 Banyu Pharmaceutical Co., Ltd Indolopyrrolocarbazole derivative and antitumor agent
CN1852914A (zh) * 2003-09-16 2006-10-25 万有制药株式会社 抗肿瘤性新型吲哚并吡咯并咔唑衍生物
US7169802B2 (en) 2003-12-23 2007-01-30 Cephalon, Inc. Fused pyrrolocarbazoles
US7241779B2 (en) * 2003-12-23 2007-07-10 Cephalon, Inc. Fused pyrrolocarbazoles
RU2255089C1 (ru) * 2003-12-26 2005-06-27 Закрытое акционерное общество "АСГЛ-Исследовательские Лаборатории" Производные гликозидов индоло[2,3-а]пирроло[3,4-с]карбазол-5,7-дионов, обладающие цитотоксической и противоопухолевой активностью
ES2326459B1 (es) 2008-04-08 2010-05-28 Universidad De Oviedo Indolocarbazoles glicosilados, su procedimiento de obtencion y sus usos.
MX2011005055A (es) 2008-11-19 2011-05-31 Cephalon Inc Nuevas formas de un compuesto de indazolo [5,4-a]pirrolo[3,4-c]car bazol.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4785085A (en) * 1986-11-21 1988-11-15 Bristol-Myers Company Rebeccamycin analogs
DE4005969A1 (de) * 1990-02-26 1991-08-29 Boehringer Mannheim Gmbh Neue trisubstituierte pyrrole, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten
EP0445736A1 (en) * 1990-03-06 1991-09-11 Bristol-Myers Squibb Company Rebeccamycin analog and pharmaceutical composition containing it
IL97233A (en) * 1990-03-06 1995-03-30 Bristol Myers Squibb Co Rebeccamycin analogs, their production and pharmaceutical compositions containing them
TW214553B (OSRAM) * 1991-04-11 1993-10-11 Schering Corp

Also Published As

Publication number Publication date
ES2079774T3 (es) 1996-01-16
KR930010039A (ko) 1993-06-21
FI106864B (fi) 2001-04-30
CZ350892A3 (en) 1993-10-13
HU217611B (hu) 2000-03-28
CZ287304B6 (cs) 2000-10-11
NO178929C (no) 1996-07-03
AU2963792A (en) 1993-06-03
CA2083534A1 (en) 1993-05-30
HU211254A9 (en) 1995-11-28
NO924593L (no) 1993-06-01
YU48963B (sh) 2003-01-31
TW224469B (OSRAM) 1994-06-01
BG61036B1 (bg) 1996-09-30
RO113469B1 (ro) 1998-07-30
FI925422A0 (fi) 1992-11-27
HUT65699A (en) 1994-07-28
DE69206242D1 (de) 1996-01-04
GR3018527T3 (en) 1996-03-31
MY114655A (en) 2002-12-31
NO924593D0 (no) 1992-11-27
DE69206242T2 (de) 1996-03-28
IL103844A0 (en) 1993-04-04
FI925422L (fi) 1993-05-30
IL103844A (en) 1997-09-30
EP0545195B1 (en) 1995-11-22
DK0545195T3 (da) 1995-12-18
ATE130617T1 (de) 1995-12-15
KR100275976B1 (ko) 2001-02-01
PL171468B1 (pl) 1997-05-30
RU2117671C1 (ru) 1998-08-20
EP0545195A1 (en) 1993-06-09
AU650376B2 (en) 1994-06-16
DZ1634A1 (fr) 2002-02-17
HU9203754D0 (en) 1993-03-29
MX9206847A (es) 1993-06-30
WO1993011145A1 (en) 1993-06-10
NO178929B (no) 1996-03-25
SA93130351B1 (ar) 2005-10-16
PL304729A1 (en) 1995-01-09
JPH06128283A (ja) 1994-05-10
BG97970A (bg) 1994-04-29
NZ245203A (en) 1997-07-27
YU102692A (sh) 1996-02-19
JP2629542B2 (ja) 1997-07-09

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