WO2010032165A3 - Prodrugs of artemisinin - Google Patents

Prodrugs of artemisinin Download PDF

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Publication number
WO2010032165A3
WO2010032165A3 PCT/IB2009/053940 IB2009053940W WO2010032165A3 WO 2010032165 A3 WO2010032165 A3 WO 2010032165A3 IB 2009053940 W IB2009053940 W IB 2009053940W WO 2010032165 A3 WO2010032165 A3 WO 2010032165A3
Authority
WO
WIPO (PCT)
Prior art keywords
prodrugs
artemisinin
relates
treatment
moieties derived
Prior art date
Application number
PCT/IB2009/053940
Other languages
French (fr)
Other versions
WO2010032165A2 (en
Inventor
Jaco Cornelius Breytenbach
David Dago N'da
Michael Ashton
Original Assignee
North-West 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 North-West University filed Critical North-West University
Publication of WO2010032165A2 publication Critical patent/WO2010032165A2/en
Priority to ZA2010/04357A priority Critical patent/ZA201004357B/en
Publication of WO2010032165A3 publication Critical patent/WO2010032165A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/18—Bridged systems
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4706—4-Aminoquinolines; 8-Aminoquinolines, e.g. chloroquine, primaquine
    • 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
    • A61K47/55—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 the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug, i.e. a dimer, oligomer or polymer of pharmacologically or therapeutically active compounds
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

This invention relates to prodrugs based on artemisinin and to a method of manufacturing such prodrugs. The prodrugs of artemisinin according to the invention have the general structure A-B-M wherein A is a dihydroartemisinin moiety; B is a linking group; and M is a moiety selected from the group consisting of moieties derived from anti-malarial drugs other than artemisinin, in particular quinoline derivatives, and moieties derived from amine compounds. The invention further relates to the use of such prodrugs in the prevention and treatment of malaria and in the manufacture of a medicament for use in such treatment. This invention also relates to the oral and transdermal application of such prodrugs.
PCT/IB2009/053940 2008-09-19 2009-09-09 Prodrugs of artemisinin WO2010032165A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ZA2010/04357A ZA201004357B (en) 2008-09-19 2010-06-21 Prodrugs of artemisinin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ZA2008/08051 2008-09-19
ZA200808051 2008-09-19

Publications (2)

Publication Number Publication Date
WO2010032165A2 WO2010032165A2 (en) 2010-03-25
WO2010032165A3 true WO2010032165A3 (en) 2010-11-18

Family

ID=41786289

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2009/053940 WO2010032165A2 (en) 2008-09-19 2009-09-09 Prodrugs of artemisinin

Country Status (2)

Country Link
WO (1) WO2010032165A2 (en)
ZA (1) ZA201004357B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019202609A1 (en) * 2018-04-16 2019-10-24 Council Of Scientific And Industrial Research Novel antimalarial compounds, process for preparation and their use for drug resistant malaria
CN110590803B (en) * 2019-08-28 2022-03-04 西南大学 Dihydroartemisinin carbonyl phenol-containing conjugate, reduction product thereof, synthetic method and application
CN111548355B (en) * 2020-04-29 2021-08-03 宁夏大学 Artemisia apiacea sulfone-piperazine-furanone derivative and preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0974354A1 (en) * 1998-07-14 2000-01-26 The Hong Kong University of Science & Technology Artemisinin derivatives
CN1296009A (en) * 1999-11-12 2001-05-23 中国科学院上海药物研究所 Arteannuin derivant containing azacyclic radical and preparation process thereof
WO2007067333A2 (en) * 2005-12-08 2007-06-14 Johns Hopkins University Trioxane dimers having high anticancer and long-lasting antimalarial activities
BRPI0700836A (en) * 2007-03-20 2008-11-04 Fundacao Oswaldo Cruz substituted quinoline derivatives, process for preparing these derivatives, pharmaceutical composition containing said derivatives, use of such derivatives in the treatment or prevention of malaria or other parasitic diseases and therapeutic method

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0974354A1 (en) * 1998-07-14 2000-01-26 The Hong Kong University of Science & Technology Artemisinin derivatives
CN1296009A (en) * 1999-11-12 2001-05-23 中国科学院上海药物研究所 Arteannuin derivant containing azacyclic radical and preparation process thereof
WO2007067333A2 (en) * 2005-12-08 2007-06-14 Johns Hopkins University Trioxane dimers having high anticancer and long-lasting antimalarial activities
BRPI0700836A (en) * 2007-03-20 2008-11-04 Fundacao Oswaldo Cruz substituted quinoline derivatives, process for preparing these derivatives, pharmaceutical composition containing said derivatives, use of such derivatives in the treatment or prevention of malaria or other parasitic diseases and therapeutic method

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
ARAUJO N C P ET AL: "Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS 20090401 GB LNKD- DOI:10.1016/J.BMCL.2009.02.013, vol. 19, no. 7, 1 April 2009 (2009-04-01), pages 2038 - 2043, XP025974914, ISSN: 0960-894X *
BELL ET AL: "Antimalarial drug synergism and antagonism: Mechanistic and clinical significance", FEMS MICROBIOLOGY LETTERS, BLACKWELL PUBLISHING, AMSTERDAM, NL LNKD- DOI:10.1016/J.FEMSLE.2005.09.035, vol. 253, no. 2, 15 December 2005 (2005-12-15), pages 171 - 184, XP005175066, ISSN: 0378-1097 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 10 February 2002 (2002-02-10), LI, YING ET AL: "Preparation of arteannuin derivatives containing azacyclic radical", XP002580976, retrieved from STN Database accession no. 2002:105791 *
HAYNES RICHARD K ET AL: "Artemisone--a highly active antimalarial drug of the artemisinin class.", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH) 20 MAR 2006 LNKD- PUBMED:16444785, vol. 45, no. 13, 20 March 2006 (2006-03-20), pages 2082 - 2088, XP002580975, ISSN: 1433-7851 *
LI YING ET AL: "Synthesis and antimalarial activity of artemisinin derivatives containing an amino group", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US LNKD- DOI:10.1021/JM990552W, vol. 43, 1 January 2000 (2000-01-01), pages 1635 - 1640, XP002236364, ISSN: 0022-2623 *
WALSH ET AL: "A novel artemisinin-quinine hybrid with potent antimalarial activity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB LNKD- DOI:10.1016/J.BMCL.2007.04.054, vol. 17, no. 13, 1 July 2007 (2007-07-01), pages 3599 - 3602, XP022114545, ISSN: 0960-894X *

Also Published As

Publication number Publication date
WO2010032165A2 (en) 2010-03-25
ZA201004357B (en) 2011-06-29

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