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
JP34191691 1991-11-29
JP341,916/91 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 (enExample)
JP (1) JP2629542B2 (enExample)
KR (1) KR100275976B1 (enExample)
AT (1) ATE130617T1 (enExample)
AU (1) AU650376B2 (enExample)
BG (1) BG61036B1 (enExample)
CA (1) CA2083534C (enExample)
CZ (1) CZ287304B6 (enExample)
DE (1) DE69206242T2 (enExample)
DK (1) DK0545195T3 (enExample)
DZ (1) DZ1634A1 (enExample)
ES (1) ES2079774T3 (enExample)
FI (1) FI106864B (enExample)
GR (1) GR3018527T3 (enExample)
HU (3) HU9203754D0 (enExample)
IL (1) IL103844A (enExample)
MX (1) MX9206847A (enExample)
MY (1) MY114655A (enExample)
NO (1) NO178929C (enExample)
NZ (1) NZ245203A (enExample)
PL (1) PL171468B1 (enExample)
RO (1) RO113469B1 (enExample)
RU (1) RU2117671C1 (enExample)
SA (1) SA93130351B1 (enExample)
TW (1) TW224469B (enExample)
WO (1) WO1993011145A1 (enExample)
YU (1) YU48963B (enExample)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2230433T3 (es) * 1994-05-09 2005-05-01 Banyu Pharmaceutical Co., Ltd. Procedimientos para la preparacion de derivados de indolopirrolocarbazol.
WO1995030682A1 (en) * 1994-05-09 1995-11-16 Banyu Pharmaceutical Co., Ltd. Antitumor indolopyprolocarbazole derivative
WO1995034663A1 (en) * 1994-06-13 1995-12-21 Banyu Pharmaceutical Co., Ltd. Gene coding for glycosyltransferase and use thereof
AU3086495A (en) * 1994-08-02 1996-03-04 Banyu Pharmaceutical Co., Ltd. Antitumor indolopyrrolocarbazoles
US5591855A (en) * 1994-10-14 1997-01-07 Cephalon, Inc. Fused pyrrolocarbazoles
US5594009A (en) * 1994-10-14 1997-01-14 Cephalon, Inc. Fused pyrrolocarbazoles
US5475110A (en) * 1994-10-14 1995-12-12 Cephalon, Inc. Fused Pyrrolocarbazoles
US5705511A (en) * 1994-10-14 1998-01-06 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
BR9711306A (pt) * 1996-08-22 1999-08-17 Bristol Myers Squibb Co Amino a-Úcar citotÄxico e derivados de a-Úcar correlatos de indolopirrolocarbazÄis
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
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
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
WO2004083228A1 (ja) 1999-09-10 2004-09-30 Katsuhisa Kojiri インドロピロロカルバゾール誘導体及び抗腫瘍剤
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
US6790836B2 (en) 2000-02-24 2004-09-14 Banyu Pharmaceutical Co., Ltd. Process for preparing indolopyrrolocarbazole derivatives, intermediates therefor, and preparation process of the intermediates
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
IL157909A0 (en) 2001-03-22 2004-03-28 Bristol Myers Squibb Co Indolopyrrolocarbazole derivatives and pharmaceutical compositions containing the same
US6559299B2 (en) 2001-03-29 2003-05-06 Merck & Co., Inc. Preparation and isolation of indolocarbazole glycosides
AU2002335472B8 (en) * 2002-03-26 2007-12-20 Banyu Pharmaceutical Co., Ltd. Combined use of antitumor indolopyrrolocarbazole derivative and other antitumor agent
CA2398828A1 (en) 2002-08-09 2004-02-09 Merck & Co., Inc. A pharmaceutical composition containing an indolopyrrolocarbazole derivative
EP1541582A1 (en) * 2002-08-23 2005-06-15 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
AU2004272457A1 (en) * 2003-09-16 2005-03-24 Banyu Pharmaceutical Co., Ltd. Novel indolopyrrolocarbazole derivative with antitumor activity
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.
CN103965204B (zh) 2008-11-19 2016-09-07 赛福伦公司 吲唑并[5,4-a]吡咯并[3,4-c]咔唑化合物的新形式

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
IL97233A (en) * 1990-03-06 1995-03-30 Bristol Myers Squibb Co Rebeccamycin analogs, their production and pharmaceutical compositions containing them
JPH0725787B2 (ja) * 1990-03-06 1995-03-22 ブリストル−マイヤーズ スクイブ カンパニー 臭化物前駆物質物質供給によるレベカマイシン類似体
WO1992018507A1 (en) * 1991-04-11 1992-10-29 Schering Corporation Anti-tumor and anti-psoriatic agents

Also Published As

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

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