WO1987006227A3 - Indoloquinone compounds - Google Patents

Indoloquinone compounds Download PDF

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Publication number
WO1987006227A3
WO1987006227A3 PCT/GB1987/000253 GB8700253W WO8706227A3 WO 1987006227 A3 WO1987006227 A3 WO 1987006227A3 GB 8700253 W GB8700253 W GB 8700253W WO 8706227 A3 WO8706227 A3 WO 8706227A3
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
hydrogen
alkyl
alkyl group
Prior art date
Application number
PCT/GB1987/000253
Other languages
French (fr)
Other versions
WO1987006227A2 (en
Inventor
Willem Nico Speckamp
Everardus Arnoldus Oostveen
Original Assignee
Jouhar Akbar Jan
Willem Nico Speckamp
Everardus Arnoldus Oostveen
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
Priority claimed from GB868609369A external-priority patent/GB8609369D0/en
Priority claimed from GB868615383A external-priority patent/GB8615383D0/en
Priority claimed from GB868629049A external-priority patent/GB8629049D0/en
Application filed by Jouhar Akbar Jan, Willem Nico Speckamp, Everardus Arnoldus Oostveen filed Critical Jouhar Akbar Jan
Priority to JP62502324A priority Critical patent/JPH0819095B2/en
Priority to AT87902608T priority patent/ATE82961T1/en
Publication of WO1987006227A2 publication Critical patent/WO1987006227A2/en
Priority to DK659887A priority patent/DK171079B1/en
Publication of WO1987006227A3 publication Critical patent/WO1987006227A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

Indoloquinone compounds useful as cytostatic agents have formula (I), where R2 and R3 are in each case, hydrogen, halogen, an alkyl group (which may be substituted), an alkoxy group or an aryloxy group, an alkylthio group or an arylthio group, a primary or secondary amino group, hydroxy group or an amino group; R5 is hydrogen, a hydroxy group, an alkoxy group, an alkyl group (which may be substituted), or a carbohydrate moiety; R6 and R7 are in each case hydrogen, halogen, or an alkyl group; R8 is a group -CH2X1, a group -CO2-M+, where M+ is a metal ion; a group -CO2R10, where R10 is hydrogen or an alkyl group (which may be substituted); a group -CONR'R'', where R' and R'' are hydrogen or alkyl groups (which may be substituted);R9 is a group -CR11R12X2, a group -CO2-M+, where M+ is a metal ion; a group -CO2R13, where R11, R12 and R13 are in each case hydrogen or an alkyl group (which may be substituted); a group -CONR'R'', where R' and R'' are in each case hydrogen or an alkyl group (which may be substituted); and X1 and X2 (when present) are hydrogen, or groups selected from OH, OR, -OC=OR, -OCO2R, -OC=ONRR, SH, SR, -SC=OR, -SC=SR, -SCO2R, -SC=SOR, -SC-ONRR, -SC-SNRR, and -NRR [where R is hydrogen, an alkyl group (which by be substituted), or an aryl group (which may be substituted)], -OSOR, -OSO2R and OP(OR)2 [where R is hydrogen, an alkyl group (which may be substituted), an aryl group (which may be substituted), or a carbohydrate moiety]; and X1 and X2 may be the same or different. Preferred compounds and methods for their manufacture are provided.
PCT/GB1987/000253 1986-04-17 1987-04-15 Indoloquinone compounds WO1987006227A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP62502324A JPH0819095B2 (en) 1986-04-17 1987-04-15 Indoloquinone compound
AT87902608T ATE82961T1 (en) 1986-04-17 1987-04-15 INDOCHINONE COMPOUNDS.
DK659887A DK171079B1 (en) 1986-04-17 1987-12-16 Indoloquinone compounds and methods for their preparation as well as drug containing them

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB8609369 1986-04-17
GB868609369A GB8609369D0 (en) 1986-04-17 1986-04-17 Indoloquinone compounds
GB8615383 1986-06-24
GB868615383A GB8615383D0 (en) 1986-06-24 1986-06-24 Pathways to bioactive indoletype compounds
GB8629049 1986-12-04
GB868629049A GB8629049D0 (en) 1986-12-04 1986-12-04 Indoloquinone compounds

Publications (2)

Publication Number Publication Date
WO1987006227A2 WO1987006227A2 (en) 1987-10-22
WO1987006227A3 true WO1987006227A3 (en) 1988-01-28

Family

ID=27262993

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1987/000253 WO1987006227A2 (en) 1986-04-17 1987-04-15 Indoloquinone compounds

Country Status (8)

Country Link
US (1) US5079257A (en)
EP (1) EP0302874B1 (en)
JP (1) JPH0819095B2 (en)
AT (1) ATE82961T1 (en)
AU (1) AU615877B2 (en)
DE (1) DE3782938T2 (en)
DK (1) DK171079B1 (en)
WO (1) WO1987006227A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3891468C2 (en) * 1989-01-12 1994-02-24 Vni Skij Chimiko Farmacevtices Ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxylic acid monohydrate hydrochloride, process for its preparation and pharmaceutical preparation with antiviral, interferon-inducing and immunomodulating action on its basis
JPH0616628A (en) * 1992-04-07 1994-01-25 Kyowa Hakko Kogyo Co Ltd Indole derivative
WO1997023456A1 (en) * 1995-12-21 1997-07-03 British Technology Group Ltd. Indoloquinone derivatives as bioreductive agents
US8563592B2 (en) 2001-11-01 2013-10-22 Spectrum Pharmaceuticals, Inc. Bladder cancer treatment and methods
ES2384208T3 (en) * 2001-11-01 2012-07-02 Spectrum Pharmaceuticals, Inc. MEDICINAL COMPOSITIONS FOR INTRAVESICAL TREATMENT OF BLADDER CANCER.
AU2004218412A1 (en) * 2003-02-28 2004-09-16 Oxigene, Inc. Compositions and methods with enhanced therapeutic activity
AU2006230582A1 (en) * 2005-03-31 2006-10-05 Spectrum Pharmaceuticals, Inc. Indoloquinone tumor radiation sensitization
US9278124B2 (en) 2012-10-16 2016-03-08 Halozyme, Inc. Hypoxia and hyaluronan and markers thereof for diagnosis and monitoring of diseases and conditions and related methods

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3265698A (en) * 1964-08-07 1966-08-09 American Cyanamid Co Novel substituted 3-(alpha-carbamoyloxy-lower alkyl)-4, 7-indoloquinones
GB1087325A (en) * 1963-10-11 1967-10-18 American Cyanamid Co Novel 3-substituted-4,7-indoloquinones and methods of preparing the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1087325A (en) * 1963-10-11 1967-10-18 American Cyanamid Co Novel 3-substituted-4,7-indoloquinones and methods of preparing the same
US3265698A (en) * 1964-08-07 1966-08-09 American Cyanamid Co Novel substituted 3-(alpha-carbamoyloxy-lower alkyl)-4, 7-indoloquinones

Also Published As

Publication number Publication date
EP0302874B1 (en) 1992-12-02
DK659887A (en) 1988-02-15
WO1987006227A2 (en) 1987-10-22
DK659887D0 (en) 1987-12-16
ATE82961T1 (en) 1992-12-15
JPH0819095B2 (en) 1996-02-28
DE3782938T2 (en) 1993-10-21
JPH01502906A (en) 1989-10-05
AU7236187A (en) 1987-11-09
AU615877B2 (en) 1991-10-17
DE3782938D1 (en) 1993-01-14
US5079257A (en) 1992-01-07
EP0302874A1 (en) 1989-02-15
DK171079B1 (en) 1996-05-28

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