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Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents

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Publication number
WO2004018475A3
WO2004018475A3 PCT/US2003/025772 US0325772W WO2004018475A3 WO 2004018475 A3 WO2004018475 A3 WO 2004018475A3 US 0325772 W US0325772 W US 0325772W WO 2004018475 A3 WO2004018475 A3 WO 2004018475A3
Authority
WO
Grant status
Application
Patent type
Prior art keywords
compounds
provided
carbinol
metabolites
cancer
Prior art date
Application number
PCT/US2003/025772
Other languages
French (fr)
Other versions
WO2004018475A2 (en )
Inventor
Wan-Ru Chao
Ling Jong
Original Assignee
Stanford Res Inst Int
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

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/08Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/30Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/30Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of indole-3-carbinol metabolites wherein the structures and substituents of the compounds are selected to enhance the compounds’ overall efficacy, particularly with respect to therapeutic activity, oral bioavailability, long-term safety, patient tolerability, and therapeutic window. The compounds are useful not only in treatment of cancer but also in prevention of cancer. One preferred class of the novel compounds have the structure of formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are defined herein. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.
PCT/US2003/025772 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents WO2004018475A3 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10224979 US6800655B2 (en) 2002-08-20 2002-08-20 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
US10/224,979 2002-08-20

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP20030793096 EP1530572B1 (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
CA 2496203 CA2496203C (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
DE2003624155 DE60324155D1 (en) 2002-08-20 2003-08-15 Indole-3-carbinol metabolites as chemotherapeutic and chemopreventive active ingredients
JP2004531045A JP4764629B2 (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic agents and chemopreventive agents

Publications (2)

Publication Number Publication Date
WO2004018475A2 true WO2004018475A2 (en) 2004-03-04
WO2004018475A3 true true WO2004018475A3 (en) 2004-04-01

Family

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Family Applications (1)

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PCT/US2003/025772 WO2004018475A3 (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents

Country Status (6)

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US (4) US6800655B2 (en)
JP (3) JP4764629B2 (en)
CA (1) CA2496203C (en)
DE (1) DE60324155D1 (en)
EP (2) EP1530572B1 (en)
WO (1) WO2004018475A3 (en)

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CN1807413B (en) * 2005-09-28 2010-05-05 中国医学科学院医药生物技术研究所;佐治亚州立大学研究基金会 Carbazole sulfonamide derivative and its preparation method
WO2007119887A1 (en) 2006-04-18 2007-10-25 Nippon Chemiphar Co., Ltd. ACTIVATING AGENT FOR PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR δ
EP2073807A1 (en) 2006-10-12 2009-07-01 Astex Therapeutics Limited Pharmaceutical combinations
JP5528806B2 (en) 2006-10-12 2014-06-25 アステックス、セラピューティックス、リミテッドAstex Therapeutics Limited Complex drug
WO2008057253A3 (en) 2006-10-27 2008-11-27 Bioresponse Llc Anti-parasitic methods and compositions utilizing diindolylmethane-related indoles
WO2008144263A1 (en) * 2007-05-18 2008-11-27 The Ohio State University Research Foundation Potent indole-3-carbinol-derived antitumor agents
US20100292316A1 (en) * 2007-07-18 2010-11-18 Research Development Foundation Improved therapeutic methods and compositions comprising chroman ring compounds
WO2009128558A1 (en) * 2008-04-15 2009-10-22 日本ケミファ株式会社 Activator for peroxisome proliferator-activated receptor
JP5550151B2 (en) * 2008-09-17 2014-07-16 エスアールアイ インターナショナルSRI International Indole-3-carbinol analogues and use as a medicament for the infection
KR101477613B1 (en) * 2009-03-31 2014-12-30 롬엔드하스전자재료코리아유한회사 The organic electronic device containing this compound, and for novel organic electronic material
WO2010118339A3 (en) * 2009-04-09 2011-02-17 University Of Kansas Formulations of indole-3-carbinol derived antitumor agents with increased oral bioavailability
CA2770494A1 (en) * 2009-08-14 2011-02-17 Ronald Barbaras Use of ppar delta ligands for the treatment or prevention of inflammation or energy metabolism/production related diseases
US8153680B2 (en) * 2009-08-25 2012-04-10 The Ohio State University Research Foundation Alkyl indole-3-carbinol-derived antitumor agents
DE102009052428A1 (en) * 2009-11-10 2011-05-12 Merck Patent Gmbh Compound for electronic devices
WO2011140164A1 (en) * 2010-05-06 2011-11-10 Merck Sharp & Dohme Corp. Aza-indole derivatives useful as modulators of faah
WO2012135133A1 (en) * 2011-04-01 2012-10-04 Sri International Lipoxygenase inhibitors
WO2015042170A1 (en) 2013-09-17 2015-03-26 Wayne State University Compositions and uses of combinations of dim-related indoles and selected anti-androgen compounds
CN104030964B (en) * 2014-06-05 2016-06-29 天津科技大学 Bis-indole compounds and synthetic methods
WO2017011920A1 (en) * 2015-07-22 2017-01-26 The Royal Institution For The Advancement Of Learning/Mcgill University Compounds and uses thereof in the treatment of cancers and other medical conditions
CN105218552A (en) * 2015-09-30 2016-01-06 中国人民解放军军事医学科学院野战输血研究所 Substituted phenyl indoline carbazole derivative and preparation method and application thereof

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Also Published As

Publication number Publication date Type
EP1530572A2 (en) 2005-05-18 application
CA2496203A1 (en) 2004-03-04 application
US20040157906A1 (en) 2004-08-12 application
EP1623985B1 (en) 2016-02-17 grant
JP4764629B2 (en) 2011-09-07 grant
DE60324155D1 (en) 2008-11-27 grant
EP1623985A3 (en) 2011-06-08 application
EP1530572B1 (en) 2008-10-15 grant
EP1623985A2 (en) 2006-02-08 application
JP4699171B2 (en) 2011-06-08 grant
WO2004018475A2 (en) 2004-03-04 application
US7078427B2 (en) 2006-07-18 grant
US20060128785A1 (en) 2006-06-15 application
JP2006500379A (en) 2006-01-05 application
US6800655B2 (en) 2004-10-05 grant
US20090023796A1 (en) 2009-01-22 application
JP2010195840A (en) 2010-09-09 application
US20040043965A1 (en) 2004-03-04 application
US7666897B2 (en) 2010-02-23 grant
JP2006036796A (en) 2006-02-09 application
JP5599236B2 (en) 2014-10-01 grant
CA2496203C (en) 2012-03-27 grant
US7429610B2 (en) 2008-09-30 grant

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