WO2008070347A3 - Betulin-peptide conjugates - Google Patents

Betulin-peptide conjugates Download PDF

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Publication number
WO2008070347A3
WO2008070347A3 PCT/US2007/082694 US2007082694W WO2008070347A3 WO 2008070347 A3 WO2008070347 A3 WO 2008070347A3 US 2007082694 W US2007082694 W US 2007082694W WO 2008070347 A3 WO2008070347 A3 WO 2008070347A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
iii
provides
present
compound
Prior art date
Application number
PCT/US2007/082694
Other languages
French (fr)
Other versions
WO2008070347A2 (en
Inventor
Robert M Carlson
Pavel A Krasutsky
Liliya Kacharova
Original Assignee
Univ Minnesota
Robert M Carlson
Pavel A Krasutsky
Liliya Kacharova
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 Univ Minnesota, Robert M Carlson, Pavel A Krasutsky, Liliya Kacharova filed Critical Univ Minnesota
Publication of WO2008070347A2 publication Critical patent/WO2008070347A2/en
Publication of WO2008070347A3 publication Critical patent/WO2008070347A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The present invention provides for novel compounds of formula I, II, III and IV, as described herein. The present invention also provides for novel methods of manufacturing compounds of formula I, II and III from compounds of formula IV, that include contacting the compound of formula IV and an amino acid (or peptide). The present invention also provides for methods of killing or inhibiting a virus, bacteria and/or fungus. The methods include contacting a virus, bacteria and/or fungus, respectively, with a suitable amount of a compound of formula I, II or III. The present invention also provides for a method of treating a mammal afflicted with a viral infection, bacterial infection and/or fungal infection. The method includes administering to a mammal in need of such treatment an effective amount of a compound of formula I, II or III.
PCT/US2007/082694 2006-10-27 2007-10-26 Betulin-peptide conjugates WO2008070347A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US85495106P 2006-10-27 2006-10-27
US60/854,951 2006-10-27

Publications (2)

Publication Number Publication Date
WO2008070347A2 WO2008070347A2 (en) 2008-06-12
WO2008070347A3 true WO2008070347A3 (en) 2008-08-21

Family

ID=39358146

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/082694 WO2008070347A2 (en) 2006-10-27 2007-10-26 Betulin-peptide conjugates

Country Status (1)

Country Link
WO (1) WO2008070347A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102558280B (en) * 2011-11-18 2014-09-17 温州大学 Method for producing 30-halogenated betulinic acid
CN102634560B (en) * 2012-04-12 2013-10-30 华南理工大学 Method for preparing Birch ketol through Dothideales mycete region-selectivity catalysis of betulin
CN103114042B (en) * 2012-12-20 2014-07-02 华南理工大学 Dothideomycete sp. mutant strain and method for catalytic production of betulin alcohol by using same
RU2535052C1 (en) * 2013-05-21 2014-12-10 Владимир Николаевич Иванов Pharmaceutical composition containing lysine, proline and triterpenic acid derivatives for treating and preventing viral infections caused by rna- and dna-containing viruses, such as: influenza, herpes, herpes zoster, human papilloma, adenoviruses, as well as bacterial infections caused by gram-positive and gram-negative microorganisms
RU2546118C1 (en) * 2014-02-10 2015-04-10 Федеральное Государственное Бюджетное Учреждение Науки Институт Химии И Химической Технологии Сибирского Отделения Российской Академии Наук (Иххт Со Ран) Method of obtaining allobetulin 3-sulphate derivatives
CN104045680B (en) 2014-06-20 2016-09-14 东北林业大学 Acetylamino acid acyl analog derivative of betulinol and preparation method thereof
PL227790B1 (en) 2015-08-13 2018-01-31 Slaski Univ Medyczny W Katowicach Phosphonates of acetylene derivatives of betulin with antitumour effects, method for producing them and applications

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020198141A1 (en) * 2001-03-23 2002-12-26 Mcchesney James D. Molecular conjugates for use in treatment of cancer
US20040001837A1 (en) * 1997-06-04 2004-01-01 Arkadiy L. Bomshteyn Betulinol derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040001837A1 (en) * 1997-06-04 2004-01-01 Arkadiy L. Bomshteyn Betulinol derivatives
US20020198141A1 (en) * 2001-03-23 2002-12-26 Mcchesney James D. Molecular conjugates for use in treatment of cancer

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
FRANCIS G W ET AL: "APPROACHES TO THE SYNTHESIS OF TERPENYL CARBOHYDRATES", ACTA CHEMICA SCANDINAVICA, vol. 45, no. 6, 1991, pages 652 - 658, XP008091594, ISSN: 0904-213X *
JEONG H-J ET AL: "Preparation of amino acid conjugates of betulinic acid with activity against human melanoma", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 9, no. 8, 19 April 1999 (1999-04-19), pages 1201 - 1204, XP004163995, ISSN: 0960-894X *
MUSTAFAEV M ET AL: "Novel betulin-containing polyelectrolyte conjugates", JOURNAL OF BIOACTIVE AND COMPATIBLE POLYMERS 200207 GB, vol. 17, no. 4, July 2002 (2002-07-01), pages 251 - 269, XP008091521, ISSN: 0883-9115 *
SAMSON, ANTONIO S.; STEVENSON, ROBERT: "Partial synthesis of glochidone", ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, vol. 5, no. 2, 1973, pages 59 - 63, XP008091518 *

Also Published As

Publication number Publication date
WO2008070347A2 (en) 2008-06-12

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