WO1996029068A3 - Use of betulinic acid and its derivatives for inhibiting malignant melanoma growth and a method of monitoring this - Google Patents

Use of betulinic acid and its derivatives for inhibiting malignant melanoma growth and a method of monitoring this Download PDF

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Publication number
WO1996029068A3
WO1996029068A3 PCT/US1996/004016 US9604016W WO9629068A3 WO 1996029068 A3 WO1996029068 A3 WO 1996029068A3 US 9604016 W US9604016 W US 9604016W WO 9629068 A3 WO9629068 A3 WO 9629068A3
Authority
WO
WIPO (PCT)
Prior art keywords
betulinic acid
malignant melanoma
derivatives
monitoring
composition
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.)
Ceased
Application number
PCT/US1996/004016
Other languages
French (fr)
Other versions
WO1996029068A2 (en
Inventor
Tapas K Dasgupta
John M Pezzuto
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.)
University of Illinois at Urbana Champaign
University of Illinois System
Original Assignee
University of Illinois at Urbana Champaign
University of Illinois System
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 University of Illinois at Urbana Champaign, University of Illinois System filed Critical University of Illinois at Urbana Champaign
Priority to EP96910535A priority Critical patent/EP0814795B1/en
Priority to JP52865496A priority patent/JP4052485B2/en
Priority to CA002215067A priority patent/CA2215067C/en
Priority to DE69634951T priority patent/DE69634951T2/en
Publication of WO1996029068A2 publication Critical patent/WO1996029068A2/en
Publication of WO1996029068A3 publication Critical patent/WO1996029068A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • 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
    • A61K31/075—Ethers or acetals
    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • 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
    • A61K31/13—Amines
    • A61K31/133—Amines having hydroxy groups, e.g. sphingosine
    • 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
    • A61K31/13—Amines
    • A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
    • 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
    • A61K31/16—Amides, e.g. hydroxamic 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • 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
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • 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
    • 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
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/72—Rhamnaceae (Buckthorn family), e.g. buckthorn, chewstick or umbrella-tree
    • A61K36/725—Ziziphus, e.g. jujube
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • 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)
  • Natural Medicines & Medicinal Plants (AREA)
  • Emergency Medicine (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Engineering & Computer Science (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medical Informatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

A composition and method of inhibiting tumor growth and treating malignant melanoma without toxic side effects are disclosed. Betulinic acid or a betulinic acid derivative is the active compound of the composition, which is topically applied to the situs of tumor. Betulinic acid is obtained by the steps of preparing an extract from the stem bark of Ziziphus mauritiana to mediate selective cytotoxic profile against human melanoma in the subject panel of human cancer cell lines, conducting a bioassay-directed fractionation based on the profile of biological activity using cultured human melanoma cells as the monitor, and obtaining betulinic acid.
PCT/US1996/004016 1995-03-21 1996-03-19 Use of betulinic acid and its derivatives for inhibiting malignant melanoma growth and a method of monitoring this Ceased WO1996029068A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP96910535A EP0814795B1 (en) 1995-03-21 1996-03-19 Topical use of betulinic acid for the treatment of malignant melanoma
JP52865496A JP4052485B2 (en) 1995-03-21 1996-03-19 How to inhibit melanoma growth
CA002215067A CA2215067C (en) 1995-03-21 1996-03-19 Use of betulinic acid and its derivatives for inhibiting malignant melanoma growth and a method of monitoring this
DE69634951T DE69634951T2 (en) 1995-03-21 1996-03-19 TOPICAL USE OF BETULINIC ACID FOR THE TREATMENT OF POOR MELANOMA

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/407,756 1995-03-21
US08/407,756 US5658947A (en) 1995-03-21 1995-03-21 Method and composition for selectively inhibiting melanoma using betalinic acid

Publications (2)

Publication Number Publication Date
WO1996029068A2 WO1996029068A2 (en) 1996-09-26
WO1996029068A3 true WO1996029068A3 (en) 1997-02-06

Family

ID=23613396

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/004016 Ceased WO1996029068A2 (en) 1995-03-21 1996-03-19 Use of betulinic acid and its derivatives for inhibiting malignant melanoma growth and a method of monitoring this

Country Status (6)

Country Link
US (1) US5658947A (en)
EP (1) EP0814795B1 (en)
JP (1) JP4052485B2 (en)
CA (1) CA2215067C (en)
DE (1) DE69634951T2 (en)
WO (1) WO1996029068A2 (en)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962527A (en) * 1995-03-21 1999-10-05 The Board Of Trustees Of The University Of Illinois Method and composition for treating cancers
US5869535A (en) * 1995-03-21 1999-02-09 The Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma
US7074768B2 (en) * 1995-08-17 2006-07-11 Idera Pharmaceuticals, Inc. Modified protein kinase A-specific oligonucleotides and methods of their use
FR2749510B1 (en) * 1996-06-07 2001-01-05 Clarins PROTECTIVE COMPOSITION AGAINST SOLAR ULTRA-VIOLET RAYS
DE19713768B4 (en) * 1997-04-03 2006-07-13 Martin-Luther-Universität Halle-Wittenberg Production of betulinic acid
EP1473301A3 (en) * 1997-06-04 2005-01-26 Cornell Research Foundation, Inc. Betulinol derivatives
AU7813598A (en) * 1997-06-04 1998-12-21 Cornell Research Foundation Inc. Betulinol derivatives
US6670345B1 (en) * 1997-09-30 2003-12-30 Dabur Research Foundation Betulinic acid derivatives for inhabiting cancer growth and process for the manufacture of betulinic acid
US6048847A (en) * 1997-09-30 2000-04-11 Dabur Research Foundation Use of betulinic acid and its derivatives for inhibiting cancer growth and a method of monitoring this
US6228850B1 (en) 1997-09-30 2001-05-08 Dabur Research Foundation Antiangiogenic activity of betulinic acid and its derivatives
DE69832363D1 (en) * 1998-03-18 2005-12-22 Dabur Pharma Ltd Betulinic derivatives for inhibiting cancer growth
US6214814B1 (en) 1998-03-18 2001-04-10 Dabur Research Foundation Use of betulinic acid derivatives for inhibiting cancer growth
US6124362A (en) * 1998-07-17 2000-09-26 The Procter & Gamble Company Method for regulating hair growth
US6482857B1 (en) 1998-07-17 2002-11-19 The University Of Texas Southwestern Medical Center Compositions which contain triterpenes for regulating hair growth
US6369109B1 (en) 1998-10-28 2002-04-09 Deutsches Krebsforschungszentrum Stiftung Des Offentlichen Rechts Betulinic acid and derivatives thereof useful for the treatment of neuroectodermal tumor
US6369101B1 (en) 1999-02-26 2002-04-09 Regents Of The University Of Minnesota Therapeutic method to treat herpes virus infection
US6392070B1 (en) * 1999-08-10 2002-05-21 Regents Of The University Of Minnesota Birch bark processing and the isolation of natural products from birch bark
DE60014180T2 (en) 2000-04-04 2005-10-06 Color Access, Inc. PREPARATION FOR IMPROVING THE EPITHELIAL LIPID BARRIER FUNCTION
GB2362649A (en) * 2000-05-25 2001-11-28 Univerzita Palackeho V Olomouc Triterpenoid derivatives
EP1309605A1 (en) 2000-08-18 2003-05-14 The Board Of Trustees Of The University Of Illinois Prodrugs of betulinic acid derivatives for the treatment of cancer and hiv
WO2002091858A1 (en) * 2001-05-11 2002-11-21 University Of Ottawa Anxiolytic marcgraviaceae compositions containing betulinic acid, betulinic acid derivatives, and methods
EP1594885B8 (en) * 2003-02-11 2009-03-25 Novelix Pharmaceuticals, Inc. Medicament for inhibiting tumour growth
US20060019934A1 (en) * 2004-05-20 2006-01-26 Saxena Brij B Anti-HIV-1 activity of betulinol derivatives
US10980865B2 (en) 2012-08-10 2021-04-20 Aquavit Pharmaceuticals, Inc. Direct application system and method for the delivery of bioactive compositions and formulations
US9808011B2 (en) 2014-12-15 2017-11-07 Biovectra Inc. Pentacyclic triterpene compounds and uses thereof
KR101909885B1 (en) * 2018-05-25 2018-10-19 김예원 Composition for Improving Meningioma Using a Salidroside and Betulin
US11202753B1 (en) 2020-03-06 2021-12-21 Aquavit Pharmaceuticals, Inc. Systems and methods for generating immune responses in subjects using microchannel delivery devices

Citations (3)

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JPH01143832A (en) * 1987-12-01 1989-06-06 Toa Nenryo Kogyo Kk Carcinostatic agent
WO1994026725A1 (en) * 1993-05-11 1994-11-24 Rhone-Poulenc Rorer S.A. Novel lupane derivatives, their preparation and pharmaceutical compositions containing same
WO1995004526A1 (en) * 1993-08-09 1995-02-16 Glycomed Incorporated Lupane triterpenoid derivatives

Family Cites Families (1)

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Patent Citations (3)

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JPH01143832A (en) * 1987-12-01 1989-06-06 Toa Nenryo Kogyo Kk Carcinostatic agent
WO1994026725A1 (en) * 1993-05-11 1994-11-24 Rhone-Poulenc Rorer S.A. Novel lupane derivatives, their preparation and pharmaceutical compositions containing same
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Title
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YASUKAWA K ET AL: "Sterol and triterpene derivatives from plants inhibit the effects of a tumor promoter, and sitosterol and betulinic acid inhibit tumor formation in mouse skin two-stage carcinogenesis.", ONCOLOGY, 1991, 48 (1) P72-6, SWITZERLAND, XP000567825 *
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Also Published As

Publication number Publication date
JPH11502525A (en) 1999-03-02
CA2215067A1 (en) 1996-09-26
WO1996029068A2 (en) 1996-09-26
JP4052485B2 (en) 2008-02-27
DE69634951T2 (en) 2006-04-20
US5658947A (en) 1997-08-19
EP0814795A2 (en) 1998-01-07
CA2215067C (en) 2006-12-05
DE69634951D1 (en) 2005-08-25
EP0814795B1 (en) 2005-07-20

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