CA2387873C - Nordihydroguaiaretic derivatives for use in treatment of tumors - Google Patents

Nordihydroguaiaretic derivatives for use in treatment of tumors Download PDF

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Publication number
CA2387873C
CA2387873C CA002387873A CA2387873A CA2387873C CA 2387873 C CA2387873 C CA 2387873C CA 002387873 A CA002387873 A CA 002387873A CA 2387873 A CA2387873 A CA 2387873A CA 2387873 C CA2387873 C CA 2387873C
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CA
Canada
Prior art keywords
tumor
cells
amino acid
substituted
salt
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
CA002387873A
Other languages
English (en)
French (fr)
Other versions
CA2387873A1 (en
Inventor
Ru Chih C. Huang
Jonathan D. Heller
Jih Ru Hwu
Ke Yung King
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.)
Johns Hopkins University
Original Assignee
Johns Hopkins University
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 Johns Hopkins University filed Critical Johns Hopkins University
Publication of CA2387873A1 publication Critical patent/CA2387873A1/en
Application granted granted Critical
Publication of CA2387873C publication Critical patent/CA2387873C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/225—Polycarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/401—Proline; Derivatives thereof, e.g. captopril
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • AIDS & HIV (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA002387873A 1999-10-15 2000-10-16 Nordihydroguaiaretic derivatives for use in treatment of tumors Expired - Lifetime CA2387873C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/418,594 1999-10-15
US09/418,594 US6214874B1 (en) 1999-10-15 1999-10-15 Treatment of HPV induced cancer using in situ application of two nordihydroguiaretic acid derivatives, tetramethyl NDGA M4N and tetraglycinal NDGA G4N
PCT/US2000/028612 WO2001028494A2 (en) 1999-10-15 2000-10-16 Nordihydroguaiaretic derivatives for use in treatment of tumors

Publications (2)

Publication Number Publication Date
CA2387873A1 CA2387873A1 (en) 2001-04-26
CA2387873C true CA2387873C (en) 2008-12-30

Family

ID=23658774

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002387873A Expired - Lifetime CA2387873C (en) 1999-10-15 2000-10-16 Nordihydroguaiaretic derivatives for use in treatment of tumors

Country Status (10)

Country Link
US (4) US6214874B1 (enExample)
EP (1) EP1231914B1 (enExample)
JP (2) JP4062664B2 (enExample)
CN (1) CN1309381C (enExample)
AT (1) ATE350030T1 (enExample)
AU (1) AU783015C (enExample)
CA (1) CA2387873C (enExample)
DE (1) DE60032795T2 (enExample)
SG (1) SG144712A1 (enExample)
WO (1) WO2001028494A2 (enExample)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6365787B1 (en) * 1994-09-30 2002-04-02 The Johns Hopkins University Compounds for the suppression of HIV TAT transactivation
US6214874B1 (en) * 1999-10-15 2001-04-10 John Hopkins University Treatment of HPV induced cancer using in situ application of two nordihydroguiaretic acid derivatives, tetramethyl NDGA M4N and tetraglycinal NDGA G4N
US6608108B2 (en) * 1999-10-15 2003-08-19 Johns Hopkins University Method for treatment of tumors using nordihydroguaiaretic acid derivatives
US20060073530A1 (en) * 2001-08-15 2006-04-06 Olaf Schneewind Methods and compositions involving sortase B
US20060141029A1 (en) * 2003-05-20 2006-06-29 Erimos Pharmaceuticals Llc Methods and compositions for delivery of catecholic butanes for treatment of diseases
AU2004249124A1 (en) * 2003-05-20 2004-12-29 Erimos Pharmaceuticals Llc Methods and compositions for delivery of catecholic butanes for treatment of diseases
US7728036B2 (en) * 2003-05-20 2010-06-01 Erimos Pharmaceuticals, Llc Methods for delivery of catecholic butanes for treatment of tumors
EP1651695B1 (en) * 2003-08-07 2009-01-21 Huntsman Advanced Materials (Switzerland) GmbH Photocrosslinkable polyurethanes
CN100440843C (zh) * 2004-05-12 2008-12-03 华为技术有限公司 一种环网及其业务实现方法
CN102210663B (zh) 2004-05-28 2013-07-31 尤尼根公司 作为双核酶强效抑制剂的二芳基烷烃
US8440648B2 (en) * 2004-07-20 2013-05-14 Erimos Pharmaceuticals Llc Methods and compositions for treatment of intraepithelial neoplasia
WO2006014669A2 (en) * 2004-07-20 2006-02-09 Erimos Pharmaceuticals Llc Methods and compositions for treatment of intraepithelial neoplasia
JP2008520548A (ja) * 2004-10-06 2008-06-19 ジョーンズ ホプキンス ユニバーシティ 薬剤耐性癌、薬剤耐性ウイルス感染症および薬剤耐性微生物感染症におけるノルジヒドログアヤレト酸誘導体の使用
EP1845787B1 (en) * 2005-01-27 2015-04-15 Erimos Pharmaceuticals LLC Formulations for injection of catecholic butanes, including ndga compounds, into animals
KR20090006062A (ko) * 2006-02-23 2009-01-14 에리모스 파마슈티컬스 엘엘씨 인플루엔자 바이러스 감염의 치료 방법
EP2076252B1 (en) * 2006-10-02 2014-04-02 Erimos Pharmaceuticals LLC Tetra-substituted ndga derivatives via ether bonds and carbamate bonds and their synthesis and pharmaceutical use
US9067875B2 (en) 2006-10-02 2015-06-30 Erimos Pharmaceuticals Llc Tetra-substituted NDGA derivatives via ether bonds and carbamate bonds and their synthesis and pharmaceutical use
US9005889B2 (en) * 2007-01-16 2015-04-14 The Johns Hopkins University Synergistic antiviral compositions comprising a viral attachment inhibitor, integration inhibitor, and proviral transcription inhibitor
NZ581837A (en) * 2007-05-11 2012-08-31 Convatec Technologies Inc Stoma seal coupling including stoma seal support
AU2009274158C1 (en) 2008-07-21 2019-09-05 Unigen, Inc. Series of skin-whitening (lightening) compounds
KR20100011963A (ko) * 2008-07-25 2010-02-03 국립암센터 Ｎｄｇａ를 포함하는 트란스글루타미나제 억제용 조성물
US20100093872A1 (en) * 2008-10-15 2010-04-15 Erimos Pharmaceuticals Llc Stable aqueous formulations of water insoluble or poorly soluble drugs
WO2010054264A1 (en) * 2008-11-07 2010-05-14 Triact Therapeutics, Inc. Use of catecholic butane derivatives in cancer therapy
CN109180448A (zh) 2011-03-24 2019-01-11 尤尼根公司 用于制备二芳基丙烷的化合物和方法
WO2012166778A2 (en) * 2011-05-31 2012-12-06 The Johns Hopkins University Conjugates of nitroimidazoles and their use as chemotherapeutic agents
WO2014015136A2 (en) * 2012-07-18 2014-01-23 The Johns Hopkins University Methods for inhibition of bnip3 and prevention and treatment of ischemia reperfusion injury by tetra-o-methyl nordihydroguaiaretic acid
AU2014223548A1 (en) 2013-02-26 2015-10-15 Triact Therapeutics, Inc. Cancer therapy
WO2015035410A1 (en) * 2013-09-09 2015-03-12 Triact Therapeutic, Inc. Cancer therapy
MX391317B (es) 2017-02-17 2025-03-21 Promotora Tecnica Ind S A De C V Composicion mejorada a base de acido norhidroguayaretico.

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5008294A (en) * 1985-02-11 1991-04-16 Chemex Pharmaceuticals, Inc. Methods of treating tumors with compositions of catecholic butanes
US5276060A (en) * 1979-06-19 1994-01-04 Block/Chemex, G.P. Methods of treating tumors with compositions of catecholic butanes
DE3009542A1 (de) * 1980-03-13 1981-09-24 Henkel KGaA, 4000 Düsseldorf Desodorierende kosmetische zusammensetzungen
US4774229A (en) * 1982-04-05 1988-09-27 Chemex Pharmaceuticals, Inc. Modification of plant extracts from zygophyllaceae and pharmaceutical use therefor
US4880637A (en) * 1985-02-11 1989-11-14 Chemex Pharmaceuticals, Inc. Compositions of catecholic butanes with zinc
US5559149A (en) * 1990-01-29 1996-09-24 Johnson & Johnson Consumer Products, Inc. Skin care compositions containing retinoids
US5646186A (en) * 1994-05-17 1997-07-08 Johnson & Johnson Consumer Products, Inc. Retinoid composition
US6071949A (en) * 1995-03-14 2000-06-06 The United States Of America As Represented By The Department Of Health And Human Services Use of lipoxygenase inhibitors as anti-cancer therapeutic and intervention agents
US5837252A (en) 1996-07-01 1998-11-17 Larreacorp, Ltd. Nontoxic extract of Larrea tridentata and method of making same
US5827898A (en) * 1996-10-07 1998-10-27 Shaman Pharmaceuticals, Inc. Use of bisphenolic compounds to treat type II diabetes
US6214874B1 (en) * 1999-10-15 2001-04-10 John Hopkins University Treatment of HPV induced cancer using in situ application of two nordihydroguiaretic acid derivatives, tetramethyl NDGA M4N and tetraglycinal NDGA G4N

Also Published As

Publication number Publication date
CA2387873A1 (en) 2001-04-26
HK1050860A1 (en) 2003-07-11
JP4062664B2 (ja) 2008-03-19
AU1207501A (en) 2001-04-30
JP2003511477A (ja) 2003-03-25
JP2008019278A (ja) 2008-01-31
WO2001028494A3 (en) 2002-01-10
EP1231914B1 (en) 2007-01-03
CN1391471A (zh) 2003-01-15
SG144712A1 (en) 2008-08-28
DE60032795D1 (de) 2007-02-15
CN1309381C (zh) 2007-04-11
US20030065016A1 (en) 2003-04-03
DE60032795T2 (de) 2007-11-08
EP1231914A2 (en) 2002-08-21
US6958411B2 (en) 2005-10-25
EP1231914A4 (en) 2004-04-14
AU783015B2 (en) 2005-09-15
US6214874B1 (en) 2001-04-10
US6417234B1 (en) 2002-07-09
WO2001028494A9 (en) 2002-08-01
US20050267208A1 (en) 2005-12-01
ATE350030T1 (de) 2007-01-15
AU783015C (en) 2006-08-24
WO2001028494A2 (en) 2001-04-26

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Effective date: 20201016