WO2004018475A3 - Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents - Google Patents

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

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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
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WO
WIPO (PCT)
Prior art keywords
compounds
carbinol
chemotherapeutic
metabolites
indole
Prior art date
Application number
PCT/US2003/025772
Other languages
French (fr)
Other versions
WO2004018475A2 (en
Inventor
Ling Jong
Wan-Ru Chao
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
Application filed by Stanford Res Inst Int filed Critical Stanford Res Inst Int
Priority to EP03793096A priority Critical patent/EP1530572B1/en
Priority to CA2496203A priority patent/CA2496203C/en
Priority to AU2003263878A priority patent/AU2003263878A1/en
Priority to JP2004531045A priority patent/JP4764629B2/en
Priority to DE60324155T priority patent/DE60324155D1/en
Publication of WO2004018475A2 publication Critical patent/WO2004018475A2/en
Publication of WO2004018475A3 publication Critical patent/WO2004018475A3/en

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    • 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
    • C07D487/02—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 two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/30—Oestrogens
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/32—Antioestrogens
    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D209/30—Indoles; 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
    • 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
    • C07D209/30—Indoles; 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
    • C07D209/42—Carbon 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 WO2004018475A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP03793096A EP1530572B1 (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
CA2496203A CA2496203C (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
AU2003263878A AU2003263878A1 (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
JP2004531045A JP4764629B2 (en) 2002-08-20 2003-08-15 Analogues of indole-3-carbinol metabolites as chemotherapeutic and chemoprotective agents
DE60324155T DE60324155D1 (en) 2002-08-20 2003-08-15 INDOL-3-CARBINOL METABOLITES AS CHEMOTHERAPEUTIC AND CHEMOPRVENTIVE AGENTS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/224,979 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

Publications (2)

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

Family

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Family Applications (1)

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PCT/US2003/025772 WO2004018475A2 (en) 2002-08-20 2003-08-15 Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents

Country Status (8)

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US (4) US6800655B2 (en)
EP (2) EP1530572B1 (en)
JP (3) JP4764629B2 (en)
AT (1) ATE411317T1 (en)
AU (1) AU2003263878A1 (en)
CA (1) CA2496203C (en)
DE (1) DE60324155D1 (en)
WO (1) WO2004018475A2 (en)

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US8916552B2 (en) 2006-10-12 2014-12-23 Astex Therapeutics Limited Pharmaceutical combinations
WO2008044045A1 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical combinations
US8586621B2 (en) * 2006-10-27 2013-11-19 Michael A. Zeligs 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
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WO2010033198A2 (en) * 2008-09-17 2010-03-25 Sri International Analogs of indole-3-carbinol and their use as agents against infection
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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 method
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US10799479B2 (en) 2015-04-10 2020-10-13 Bioresponse, L.L.C. Self-emulsifying formulations of DIM-related indoles
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
CN105218552B (en) * 2015-09-30 2018-02-27 中国人民解放军军事医学科学院野战输血研究所 A kind of substituted-phenyl indoline carbazole derivates and preparation method and application
CN110698654B (en) * 2018-07-10 2021-04-02 中国科学院长春应用化学研究所 Hyperbranched conjugated polyelectrolyte based on trimeric indole, preparation method and application thereof

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Also Published As

Publication number Publication date
JP2006036796A (en) 2006-02-09
US20060128785A1 (en) 2006-06-15
EP1530572B1 (en) 2008-10-15
AU2003263878A1 (en) 2004-03-11
CA2496203A1 (en) 2004-03-04
DE60324155D1 (en) 2008-11-27
US20040157906A1 (en) 2004-08-12
US20040043965A1 (en) 2004-03-04
JP5599236B2 (en) 2014-10-01
JP4699171B2 (en) 2011-06-08
EP1623985A2 (en) 2006-02-08
US7429610B2 (en) 2008-09-30
EP1623985A3 (en) 2011-06-08
JP2006500379A (en) 2006-01-05
JP2010195840A (en) 2010-09-09
CA2496203C (en) 2012-03-27
EP1623985B1 (en) 2016-02-17
US7078427B2 (en) 2006-07-18
JP4764629B2 (en) 2011-09-07
WO2004018475A2 (en) 2004-03-04
EP1530572A2 (en) 2005-05-18
US20090023796A1 (en) 2009-01-22
US6800655B2 (en) 2004-10-05
ATE411317T1 (en) 2008-10-15
US7666897B2 (en) 2010-02-23

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