CA2469649C - Derivatives of isoindigo, indigo and indirubin and use in treating cancer - Google Patents

Derivatives of isoindigo, indigo and indirubin and use in treating cancer Download PDF

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Publication number
CA2469649C
CA2469649C CA2469649A CA2469649A CA2469649C CA 2469649 C CA2469649 C CA 2469649C CA 2469649 A CA2469649 A CA 2469649A CA 2469649 A CA2469649 A CA 2469649A CA 2469649 C CA2469649 C CA 2469649C
Authority
CA
Canada
Prior art keywords
cancer
compound
natura
agents
meisoindigo
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 - Lifetime
Application number
CA2469649A
Other languages
English (en)
French (fr)
Other versions
CA2469649A1 (en
Inventor
Longgui Wang
Xiaomei Liu
Ruihuan Chen
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.)
Natrogen Therapeutics Inc
Original Assignee
Natrogen Therapeutics Inc
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 US10/021,589 external-priority patent/US6566341B1/en
Application filed by Natrogen Therapeutics Inc filed Critical Natrogen Therapeutics Inc
Publication of CA2469649A1 publication Critical patent/CA2469649A1/en
Application granted granted Critical
Publication of CA2469649C publication Critical patent/CA2469649C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/23Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • 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
    • C07D209/32Oxygen atoms
    • C07D209/34Oxygen atoms in position 2

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)
CA2469649A 2001-12-13 2002-12-13 Derivatives of isoindigo, indigo and indirubin and use in treating cancer Expired - Lifetime CA2469649C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US10/021,589 US6566341B1 (en) 2001-12-13 2001-12-13 Derivative of isoindigo, indigo and indirubin for the treatment of cancer
US10/021,589 2001-12-13
US40726702P 2002-09-03 2002-09-03
US60/407,267 2002-09-03
PCT/US2002/039866 WO2003051900A1 (en) 2001-12-13 2002-12-13 Derivatives of isoindigo, indigo and indirubin and use in treating cancer

Publications (2)

Publication Number Publication Date
CA2469649A1 CA2469649A1 (en) 2003-06-26
CA2469649C true CA2469649C (en) 2011-05-03

Family

ID=26694875

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2469649A Expired - Lifetime CA2469649C (en) 2001-12-13 2002-12-13 Derivatives of isoindigo, indigo and indirubin and use in treating cancer

Country Status (8)

Country Link
US (1) US6933315B2 (enExample)
EP (1) EP1458734B1 (enExample)
JP (1) JP2005516938A (enExample)
AT (1) ATE484514T1 (enExample)
AU (1) AU2002357191A1 (enExample)
CA (1) CA2469649C (enExample)
DE (1) DE60237993D1 (enExample)
WO (1) WO2003051900A1 (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8748475B2 (en) 2004-01-12 2014-06-10 Natrogen Therapeutics International, Inc. Methods and compositions for treating lupus
US8563525B2 (en) 2004-01-12 2013-10-22 Natrogen Therapeutics International, Inc. Methods of treating an inflammatory-related disease
US7582670B2 (en) 2001-12-13 2009-09-01 Natrogen Therapeutics, Inc. Methods of treating an inflammatory-related disease
US20100098702A1 (en) 2008-09-16 2010-04-22 Longgui Wang Method of treating androgen independent prostate cancer
US20050154046A1 (en) * 2004-01-12 2005-07-14 Longgui Wang Methods of treating an inflammatory-related disease
CN101074229B (zh) * 2007-06-08 2010-09-01 无锡杰西医药科技有限公司 7-氮杂靛玉红和7-氮杂异靛蓝衍生物制备及其药学用途
CN101426268B (zh) * 2007-11-02 2010-08-25 大唐移动通信设备有限公司 导频资源分配方法、系统和设备
US8563595B2 (en) * 2008-11-14 2013-10-22 Board Of Regents, The University Of Texas System Treatment of cancer with complex organic-inorganic pigment compositions
CA2868302A1 (en) * 2012-03-23 2013-09-26 Dennis M. Brown Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo
JP6382187B2 (ja) 2012-06-21 2018-08-29 フォスフォレックス,インコーポレーテッド インジルビンのナノ微粒子、その誘導体およびそれらを作製しかつ利用する方法
CN103333161B (zh) * 2013-05-28 2015-09-30 滁州市洛达生物科技有限公司 1’-氧代靛玉红的制备和用途
KR102361918B1 (ko) 2017-05-26 2022-02-14 다이호야쿠힌고교 가부시키가이샤 신규 비페닐 화합물 또는 그의 염
JP6738962B2 (ja) * 2017-05-26 2020-08-12 大鵬薬品工業株式会社 新規なビフェニル化合物を用いた抗腫瘍効果増強剤
WO2018221555A1 (ja) 2017-05-31 2018-12-06 大鵬薬品工業株式会社 Insm1の発現に基づくlsd1阻害剤の治療効果の予測方法
CN113365990A (zh) * 2018-12-07 2021-09-07 纳特罗根治疗国际有限公司 甲异靛的多晶型和甲异靛的改进制剂
EP4058151B1 (en) 2019-11-13 2025-05-21 Taiho Pharmaceutical Co., Ltd. Novel salt of terphenyl compound
US11345818B1 (en) 2020-12-29 2022-05-31 Industrial Technology Research Institute Dye for fiber and dyeing method
WO2022232243A1 (en) * 2021-04-27 2022-11-03 Curapep Llc Compositions for wound relief and inhibiting a phd protein and methods of treatment
CN114920728B (zh) * 2022-05-27 2023-10-20 中南大学 一种甲异靛衍生物及其制备方法与应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS617254A (ja) * 1984-06-20 1986-01-13 Isukura Sangyo Kk ビスインドリノンおよびそれを主成分とする制癌剤
US5696092A (en) * 1995-03-07 1997-12-09 George Washington University Methods and compositions for inhibiting metastasis of epithelial cell-derived cancers
EP1079826B1 (en) * 1998-05-29 2003-03-05 CNRS, Centre National de la Recherche Scientifique Use of indigoid bisindole derivatives for the manufacture of a medicament to inhibit cyclin dependent kinases
EP1169305A1 (en) * 1999-04-12 2002-01-09 Eisenbrand, Gerhard, Prof. Dr. Indigoid bisindole derivatives
US6664285B1 (en) * 1999-04-12 2003-12-16 Gerhard Eisenbrand Use of cell membrane penetrating indigoid bisindole derivatives

Also Published As

Publication number Publication date
WO2003051900A1 (en) 2003-06-26
EP1458734A1 (en) 2004-09-22
ATE484514T1 (de) 2010-10-15
AU2002357191A1 (en) 2003-06-30
EP1458734B1 (en) 2010-10-13
EP1458734A4 (en) 2007-12-19
JP2005516938A (ja) 2005-06-09
US20040225002A1 (en) 2004-11-11
DE60237993D1 (de) 2010-11-25
US6933315B2 (en) 2005-08-23
CA2469649A1 (en) 2003-06-26

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Effective date: 20221213