WO2004018475A2 - 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 PDFInfo
- Publication number
- WO2004018475A2 WO2004018475A2 PCT/US2003/025772 US0325772W WO2004018475A2 WO 2004018475 A2 WO2004018475 A2 WO 2004018475A2 US 0325772 W US0325772 W US 0325772W WO 2004018475 A2 WO2004018475 A2 WO 2004018475A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- substituted
- hydrogen
- compound
- cancer
- Prior art date
Links
- 0 *c1c(c2c(*)c(*)c(*)c(*)c2[n]2*)c2c(*)c2c1c(c(*)c(*)c(*)c1*)c1[n]2* Chemical compound *c1c(c2c(*)c(*)c(*)c(*)c2[n]2*)c2c(*)c2c1c(c(*)c(*)c(*)c1*)c1[n]2* 0.000 description 3
- VFTRKSBEFQDZKX-UHFFFAOYSA-N C(c1c[nH]c2ccccc12)c1c[nH]c2c1cccc2 Chemical compound C(c1c[nH]c2ccccc12)c1c[nH]c2c1cccc2 VFTRKSBEFQDZKX-UHFFFAOYSA-N 0.000 description 1
- IVYPNXXAYMYVSP-UHFFFAOYSA-N OCc1c[nH]c2ccccc12 Chemical compound OCc1c[nH]c2ccccc12 IVYPNXXAYMYVSP-UHFFFAOYSA-N 0.000 description 1
- YCPBCVTUBBBNJJ-UHFFFAOYSA-N c(cc1c2c3)ccc1[nH]c2cc1c3[nH]c2ccccc12 Chemical compound c(cc1c2c3)ccc1[nH]c2cc1c3[nH]c2ccccc12 YCPBCVTUBBBNJJ-UHFFFAOYSA-N 0.000 description 1
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
- C07D487/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Virology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003263878A AU2003263878A1 (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 |
JP2004531045A JP4764629B2 (ja) | 2002-08-20 | 2003-08-15 | 化学療法薬および化学防御薬としてのインドール−3−カルビノール代謝物の類似物 |
DE60324155T DE60324155D1 (de) | 2002-08-20 | 2003-08-15 | Indol-3-carbinol metaboliten als chemotherapeutische und chemopräventive wirkstoffen |
EP03793096A EP1530572B1 (en) | 2002-08-20 | 2003-08-15 | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/224,979 | 2002-08-20 | ||
US10/224,979 US6800655B2 (en) | 2002-08-20 | 2002-08-20 | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004018475A2 true WO2004018475A2 (en) | 2004-03-04 |
WO2004018475A3 WO2004018475A3 (en) | 2004-04-01 |
Family
ID=31946289
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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)
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1811842A2 (en) * | 2004-11-06 | 2007-08-01 | The Regents of the University of California | 3,3'-diindolylmethane immune activating compositions |
JP2008545663A (ja) * | 2005-05-27 | 2008-12-18 | クイーンズ ユニバーシティ アット キングストン | タンパク質フォールディング障害の治療 |
WO2010033198A3 (en) * | 2008-09-17 | 2010-08-19 | Sri International | Analogs of indole-3-carbinol and their use as agents against infection |
US8404726B2 (en) | 2006-04-18 | 2013-03-26 | Nippon Chemiphar Co. Ltd. | Activating agent for peroxisome proliferator activated receptor δ |
US8648208B2 (en) | 2008-04-15 | 2014-02-11 | Nippon Chemiphar Co. Ltd. | Activating agent for peroxisome proliferator activated receptor |
CN104030964A (zh) * | 2014-06-05 | 2014-09-10 | 天津科技大学 | 双吲哚类化合物及合成方法 |
CN105218552A (zh) * | 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 | 一种取代苯基二氢吲哚咔唑衍生物及其制备方法与应用 |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6800655B2 (en) * | 2002-08-20 | 2004-10-05 | Sri International | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
US8080577B2 (en) * | 2004-05-06 | 2011-12-20 | Bioresponse, L.L.C. | Diindolylmethane formulations for the treatment of leiomyomas |
EP1838303B1 (en) | 2004-12-30 | 2011-02-09 | Bioresponse LLC | Use of diindolylmethane-related indoles for the treatment and prevention of respiratory syncytial virus associates conditions |
KR101345002B1 (ko) | 2005-01-21 | 2013-12-31 | 아스텍스 테라퓨틱스 리미티드 | 제약 화합물 |
CN1807413B (zh) * | 2005-09-28 | 2010-05-05 | 中国医学科学院医药生物技术研究所 | 咔唑磺酰胺衍生物及其制备方法 |
US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
BRPI0717753B1 (pt) | 2006-10-27 | 2022-04-12 | Bioresponse, Llc | Uso de uma composição compreendendo 50-250 mg de um ou mais indóis relacionados com dim e um ou mais agentes anti-protozoários, e, composição |
US7807705B2 (en) * | 2007-05-18 | 2010-10-05 | 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 |
KR101477613B1 (ko) * | 2009-03-31 | 2014-12-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 |
WO2010118339A2 (en) * | 2009-04-09 | 2010-10-14 | University Of Kansas | Formulations of indole-3-carbinol derived antitumor agents with increased oral bioavailability |
CN102724978A (zh) * | 2009-08-14 | 2012-10-10 | 塞伦尼斯治疗公司 | 用于治疗或预防炎症或能量代谢/产生相关疾病的PPARδ配体的用途 |
US8153680B2 (en) * | 2009-08-25 | 2012-04-10 | The Ohio State University Research Foundation | Alkyl indole-3-carbinol-derived antitumor agents |
DE102009052428A1 (de) * | 2009-11-10 | 2011-05-12 | Merck Patent Gmbh | Verbindung für elektronische Vorrichtungen |
AU2011248175A1 (en) * | 2010-05-06 | 2012-10-25 | Merck Sharp & Dohme Corp. | Aza-Indole derivatives useful as modulators of FAAH |
JP6034853B2 (ja) * | 2011-04-01 | 2016-11-30 | エスアールアイ インターナショナルSRI International | リポキシゲナーゼ阻害剤 |
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 |
US9969686B2 (en) * | 2014-08-05 | 2018-05-15 | Wisconsin Alumni Research Foundation | Synthesis of diindolylmethanes and indolo[3,2-b]carbazoles, compounds formed thereby, and pharmaceutical compositions containing them |
US9918965B2 (en) | 2015-04-10 | 2018-03-20 | Bioresponse, L.L.C. | Self-emulsifying formulations of DIM-related indoles |
CA3030582A1 (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 |
CN110698654B (zh) * | 2018-07-10 | 2021-04-02 | 中国科学院长春应用化学研究所 | 基于三聚吲哚的超支化共轭聚电解质及其制备方法和用途 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1998050357A2 (en) * | 1997-03-07 | 1998-11-12 | The Texas A & M University System | Substituted analogs of indole-3-carbinol and of diindolymethane as antiestrogens |
WO2002036561A1 (en) * | 2000-11-03 | 2002-05-10 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Bis-heterocyclic compounds with antitumour and chemosensitising activity |
Family Cites Families (18)
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DE1282451B (de) * | 1965-09-01 | 1968-11-07 | Kalle Ag | Lichtempfindliche Schicht und Verfahren zur Herstellung fixierter Bilder |
US4636820A (en) * | 1980-03-06 | 1987-01-13 | The Hilton-Davis Chemical | Compositions, process and systems |
EP0266310B1 (de) * | 1986-10-28 | 2001-12-05 | Ciba SC Holding AG | Chromogene Phthalide |
GB8713564D0 (en) | 1987-06-10 | 1987-07-15 | Kong Y C | Synthesis |
CZ280738B6 (cs) * | 1988-02-10 | 1996-04-17 | F. Hoffmann - La Roche And Co., Aktiengesellschaft | Substituované pyrroly, jejich použití pro výrobu léčiv a léčiva na jejich bázi |
US5086171A (en) * | 1989-03-08 | 1992-02-04 | Appleton Papers Inc. | Bis-(indolyl)ethylenes |
US5116978A (en) * | 1989-03-08 | 1992-05-26 | Appleton Papers Inc. | Process for bis(indolyl)ethylene synthesis |
JP3038064B2 (ja) * | 1991-10-07 | 2000-05-08 | 日清製粉株式会社 | インドール誘導体およびこれを有効成分とする抗潰瘍薬 |
DE59207620D1 (de) * | 1991-10-30 | 1997-01-16 | Ciba Geigy Ag | NIR-Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
US5206377A (en) * | 1991-12-05 | 1993-04-27 | Whitby Research, Inc. | Compounds useful as antiproliferative agents |
US5407102A (en) * | 1994-02-15 | 1995-04-18 | Freudinger; Mark J. | Apparatus for dispensing a quantity of flowable material |
US5942340A (en) * | 1997-10-02 | 1999-08-24 | Xerox Corporation | Indolocarbazole electroluminescent devices |
US5843607A (en) * | 1997-10-02 | 1998-12-01 | Xerox Corporation | Indolocarbazole photoconductors |
AU752464B2 (en) * | 1998-05-04 | 2002-09-19 | Zentaris Gmbh | Indole derivatives and their use in the treatment of malignant and other diseases caused by pathological cell proliferation |
CA2335254A1 (en) * | 1998-07-08 | 2000-01-20 | Harbor Branch Oceanographic Institution, Inc. | Bis-indole derivatives and their use as antiinflammatory agents |
IT1317926B1 (it) | 2000-11-03 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Derivati triciclici dell'indolo ad attivita' antiangiogenica. |
JP2003346530A (ja) | 2002-05-23 | 2003-12-05 | Nippon Sheet Glass Co Ltd | 面状光源装置および画像読み取り装置 |
US6800655B2 (en) * | 2002-08-20 | 2004-10-05 | Sri International | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
-
2002
- 2002-08-20 US US10/224,979 patent/US6800655B2/en not_active Expired - Lifetime
-
2003
- 2003-08-15 AU AU2003263878A patent/AU2003263878A1/en not_active Abandoned
- 2003-08-15 CA CA2496203A patent/CA2496203C/en not_active Expired - Fee Related
- 2003-08-15 DE DE60324155T patent/DE60324155D1/de not_active Expired - Lifetime
- 2003-08-15 JP JP2004531045A patent/JP4764629B2/ja not_active Expired - Fee Related
- 2003-08-15 EP EP03793096A patent/EP1530572B1/en not_active Expired - Lifetime
- 2003-08-15 AT AT03793096T patent/ATE411317T1/de not_active IP Right Cessation
- 2003-08-15 EP EP05077401.7A patent/EP1623985B1/en not_active Expired - Fee Related
- 2003-08-15 WO PCT/US2003/025772 patent/WO2004018475A2/en active Application Filing
-
2004
- 2004-02-03 US US10/772,036 patent/US7078427B2/en not_active Expired - Lifetime
-
2005
- 2005-10-19 JP JP2005305080A patent/JP4699171B2/ja not_active Expired - Fee Related
-
2006
- 2006-02-07 US US11/350,232 patent/US7429610B2/en not_active Expired - Lifetime
-
2008
- 2008-09-05 US US12/205,532 patent/US7666897B2/en not_active Expired - Fee Related
-
2010
- 2010-06-18 JP JP2010139927A patent/JP5599236B2/ja not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1998050357A2 (en) * | 1997-03-07 | 1998-11-12 | The Texas A & M University System | Substituted analogs of indole-3-carbinol and of diindolymethane as antiestrogens |
WO2002036561A1 (en) * | 2000-11-03 | 2002-05-10 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Bis-heterocyclic compounds with antitumour and chemosensitising activity |
Non-Patent Citations (12)
Title |
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ALLESSANDRA NAPOLITANO ET AL.: "Oxidation chemistry of 5,6-dihyroxy-2-methylindole" TETRAHEDRON, (INCL TETRAHEDRON REPORTS), vol. 49, no. 40, - 1993 pages 9143-9150, XP002265926 OXFORD GB * |
ALPARSLAN AYGÜN ET AL.: "Synthesis and biological evaluation of structural variants of carbazoquinocin C" JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 40, no. 3, - 2003 pages 411-417, XP002265924 * |
ANTHONY H. JACKSON ET AL.: "Electrophilic substitution in indoles. Part 15. The reaction between methylenedi-indoles and p-nitrobenzenediazonium fluoroborate." JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1., vol. 11, - 1987 pages 2543-2551, XP002265927 CHEMICAL SOCIETY. LETCHWORTH., GB ISSN: 0300-922X * |
C. K. LAU ET AL.: "Reductive deoxygenation of aryl aldehydes and ketones and benzylic, allylic, and tertiary alcohols by ZnI2-NaCNBH3" JOURNAL OF ORGANIC CHEMISTRY., vol. 51, no. 15, - 1986 pages 3038-3043, XP002265928 AMERICAN CHEMICAL SOCIETY. EASTON., US ISSN: 0022-3263 * |
CHEMICAL ABSTRACTS, vol. 80, no. 11, 18 March 1974 (1974-03-18) Columbus, Ohio, US; abstract no. 59818c, HINO, TOHRU ET AL.: "Preparation of 3-substituted 2-indolinethiones via diindolyl disulfides. Reaction of 3-substituted indoles with sulfur monochloride." XP002265932 & CHEM. PHARM. BULL., vol. 21, no. 12, - 1973 pages 2739-2748, -& DATABASE CAPLUS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; Database accession no. 80:59818 XP002265934 * |
CHEMICAL ABSTRACTS, vol. 82, no. 17, 28 April 1975 (1975-04-28) Columbus, Ohio, US; abstract no. 111897k, HINO, TOHRU ET AL.: "Reaction of skatole with iodine in the presence of thiourea." XP002265931 & CHEM. PHARM. BULL., vol. 22, no. 11, - 1974 pages 2728-2731, -& DATABASE CAPLUS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; Database accession no. 82:111897 XP002265933 * |
DAVID ST. C. BLACK ET AL.: "Calix[3]indoles, new macrocyclic tris(indolylmethylene)compounds with 2,7-linkages" CHEMICAL COMMUNICATIONS - CHEMCOM., vol. 10, - 1993 pages 819-821, XP002265922 ROYAL SOCIETY OF CHEMISTRY., GB ISSN: 1359-7345 * |
DAVID STC. BLACK ET AL.: "Synthesis of indolo[3,2-b]carbazoles from 4,6-dimethoxyindole and aryl aldehydes" TETRAHEDRON, (INCL TETRAHEDRON REPORTS), vol. 51, no. 43, - 1995 pages 11801-11808, XP002265921 OXFORD GB * |
GREGOR WILLE ET AL.: "Malassezin- a novel agonist of the arylhydrocarbon receptor from the yeast Malassezia furfur" BIOORGANIC & MEDICINAL CHEMISTRY, vol. 9, no. 4, - 2001 pages 955-960, XP002265925 * |
HENNING VON DOBENECK ET AL.: "Zur Chemie des Indols, VI. Alpha.beta'-Diindolylmethane und -methene. Der Urorosein-Chromophor" CHEMISCHE BERICHTE., vol. 102, no. 4, - 1969 pages 1347-1356, XP002265930 VERLAG CHEMIE GMBH. WEINHEIM., DE ISSN: 0009-2940 * |
SIEGFRIED HÜNIG ET AL.: "Synthese vinyloger und azavinyloger Redoxsysteme mit Indolylresten als Endgruppen" JUSTUS LIEBIGS ANNALEN DER CHEMIE., vol. 6, - 1976 pages 1039-1059, XP002265929 VERLAG CHEMIE GMBH. WEINHEIM., DE ISSN: 0075-4617 * |
ULF PINDUR ET AL.: "Reaktivität und Reaktionswege von methylsubstituierten Bisindolylcarbenium-Ionen" JOURNAL OF HETEROCYCLIC CHEMISTRY., vol. 24, no. 1, - 1987 pages 159-163, XP002265923 HETEROCORPORATION. PROVO., US ISSN: 0022-152X * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1811842A2 (en) * | 2004-11-06 | 2007-08-01 | The Regents of the University of California | 3,3'-diindolylmethane immune activating compositions |
EP1811842A4 (en) * | 2004-11-06 | 2008-02-27 | Univ California | 3,3'-DIINDOLYLMETHANE IMMUNA-ACTIVE COMPOSITIONS |
EP2314294A3 (en) * | 2004-11-06 | 2011-09-14 | The Regents of The University of California | 3,3'-diindolylmethane immune activating compositions |
JP2008545663A (ja) * | 2005-05-27 | 2008-12-18 | クイーンズ ユニバーシティ アット キングストン | タンパク質フォールディング障害の治療 |
US8404726B2 (en) | 2006-04-18 | 2013-03-26 | Nippon Chemiphar Co. Ltd. | Activating agent for peroxisome proliferator activated receptor δ |
US8648208B2 (en) | 2008-04-15 | 2014-02-11 | Nippon Chemiphar Co. Ltd. | Activating agent for peroxisome proliferator activated receptor |
WO2010033198A3 (en) * | 2008-09-17 | 2010-08-19 | Sri International | Analogs of indole-3-carbinol and their use as agents against infection |
US8278341B2 (en) | 2008-09-17 | 2012-10-02 | Sri International | Analogs of indole-3-carbinol and their use as agents against infection |
CN104030964A (zh) * | 2014-06-05 | 2014-09-10 | 天津科技大学 | 双吲哚类化合物及合成方法 |
CN104030964B (zh) * | 2014-06-05 | 2016-06-29 | 天津科技大学 | 双吲哚类化合物及合成方法 |
CN105218552A (zh) * | 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 | 一种取代苯基二氢吲哚咔唑衍生物及其制备方法与应用 |
CN105218552B (zh) * | 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 | 一种取代苯基二氢吲哚咔唑衍生物及其制备方法与应用 |
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WO2004018475A3 (en) | 2004-04-01 |
EP1623985A2 (en) | 2006-02-08 |
US20090023796A1 (en) | 2009-01-22 |
US7666897B2 (en) | 2010-02-23 |
US6800655B2 (en) | 2004-10-05 |
US20060128785A1 (en) | 2006-06-15 |
EP1623985A3 (en) | 2011-06-08 |
US20040157906A1 (en) | 2004-08-12 |
US7078427B2 (en) | 2006-07-18 |
EP1530572B1 (en) | 2008-10-15 |
JP2006036796A (ja) | 2006-02-09 |
US7429610B2 (en) | 2008-09-30 |
JP4764629B2 (ja) | 2011-09-07 |
ATE411317T1 (de) | 2008-10-15 |
JP5599236B2 (ja) | 2014-10-01 |
AU2003263878A1 (en) | 2004-03-11 |
EP1623985B1 (en) | 2016-02-17 |
EP1530572A2 (en) | 2005-05-18 |
DE60324155D1 (de) | 2008-11-27 |
JP2010195840A (ja) | 2010-09-09 |
CA2496203A1 (en) | 2004-03-04 |
JP4699171B2 (ja) | 2011-06-08 |
CA2496203C (en) | 2012-03-27 |
JP2006500379A (ja) | 2006-01-05 |
US20040043965A1 (en) | 2004-03-04 |
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