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WO2009082818A8 - Novel c-21-keto lupane derivatives preparation and use thereof - Google Patents

Novel c-21-keto lupane derivatives preparation and use thereof Download PDF

Info

Publication number
WO2009082818A8
WO2009082818A8 PCT/CA2008/002290 CA2008002290W WO2009082818A8 WO 2009082818 A8 WO2009082818 A8 WO 2009082818A8 CA 2008002290 W CA2008002290 W CA 2008002290W WO 2009082818 A8 WO2009082818 A8 WO 2009082818A8
Authority
WO
WIPO (PCT)
Prior art keywords
keto
novel
derivatives preparation
formula
treatment
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/CA2008/002290
Other languages
French (fr)
Other versions
WO2009082818A1 (en
Inventor
Christophe Moinet
Marc Courchesne
Liliane Halab
Nathalie Chauret
Laval Chan Chun Kong
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.)
Virochem Pharma Inc
Original Assignee
Virochem Pharma 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
Application filed by Virochem Pharma Inc filed Critical Virochem Pharma Inc
Priority to JP2010540996A priority Critical patent/JP2011508747A/en
Priority to MX2010007374A priority patent/MX2010007374A/en
Priority to CA2711420A priority patent/CA2711420A1/en
Priority to AU2008342536A priority patent/AU2008342536A1/en
Priority to CN2008801275023A priority patent/CN101977924A/en
Priority to EP08867782A priority patent/EP2240504A1/en
Publication of WO2009082818A1 publication Critical patent/WO2009082818A1/en
Publication of WO2009082818A8 publication Critical patent/WO2009082818A8/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • 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
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Virology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The invention relates to 21 -keto triterpene compounds of formula (I): wherein R1, X and Y are as defined herein, and pharmaceutically acceptable salts and solvates thereof. These compounds exhibit significant anti-HIV activity. Thus, the invention also relates to methods for prevention or treatment of HIV infections by administering therapeutically effective amounts of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof to a subject in need of such treatment.
PCT/CA2008/002290 2008-01-03 2008-12-23 Novel c-21-keto lupane derivatives preparation and use thereof Ceased WO2009082818A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2010540996A JP2011508747A (en) 2008-01-03 2008-12-23 Novel C-21 kettle bread derivatives, their preparation and use
MX2010007374A MX2010007374A (en) 2008-01-03 2008-12-23 Novel c-21-keto lupane derivatives preparation and use thereof.
CA2711420A CA2711420A1 (en) 2008-01-03 2008-12-23 Novel c-21-keto lupane derivatives preparation and use thereof
AU2008342536A AU2008342536A1 (en) 2008-01-03 2008-12-23 Novel C-21-keto lupane derivatives preparation and use thereof
CN2008801275023A CN101977924A (en) 2008-01-03 2008-12-23 Novel c-21-keto lupane derivatives preparation and use thereof
EP08867782A EP2240504A1 (en) 2008-01-03 2008-12-23 Novel c-21-keto lupane derivatives preparation and use thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US1876608P 2008-01-03 2008-01-03
US61/018,766 2008-01-03
US3968008P 2008-03-26 2008-03-26
US61/039,680 2008-03-26

Publications (2)

Publication Number Publication Date
WO2009082818A1 WO2009082818A1 (en) 2009-07-09
WO2009082818A8 true WO2009082818A8 (en) 2009-09-03

Family

ID=40823728

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2008/002290 Ceased WO2009082818A1 (en) 2008-01-03 2008-12-23 Novel c-21-keto lupane derivatives preparation and use thereof

Country Status (7)

Country Link
EP (1) EP2240504A1 (en)
JP (1) JP2011508747A (en)
CN (1) CN101977924A (en)
AU (1) AU2008342536A1 (en)
CA (1) CA2711420A1 (en)
MX (1) MX2010007374A (en)
WO (1) WO2009082818A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11116737B1 (en) 2020-04-10 2021-09-14 University Of Georgia Research Foundation, Inc. Methods of using probenecid for treatment of coronavirus infections

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5562255B2 (en) 2008-01-25 2014-07-30 キメリクス，インコーポレイテッド How to treat viral infections
US9067966B2 (en) 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
SMT201800290T1 (en) 2010-01-27 2018-07-17 Viiv Healthcare Co Antiviral therapy
US20120302534A1 (en) * 2010-02-11 2012-11-29 Daxin Gao Derivatives of betulin
EP3216789A1 (en) 2010-02-12 2017-09-13 Chimerix, Inc. Methods of treating viral infection
CA2797601A1 (en) 2010-04-26 2011-11-10 Chimerix, Inc. Methods of treating retroviral infections and related dosage regimes
WO2013020245A1 (en) * 2011-08-08 2013-02-14 Glaxosmithkline Llc Carbonyl derivatives of betulin
CN104844679B (en) * 2011-12-16 2017-03-01 葛兰素史克有限责任公司 The derivant of betulin
JO3387B1 (en) 2011-12-16 2019-03-13 Glaxosmithkline Llc Derivatives of betulin
CN103242413B (en) * 2012-02-08 2015-08-26 江西青峰药业有限公司 Lupane triterpene system's derivative and pharmaceutical use thereof
AU2013358897B2 (en) * 2012-12-14 2017-01-05 Glaxosmithkline Llc Pharmaceutical compositions
US9637516B2 (en) 2012-12-31 2017-05-02 Hetero Research Foundation Betulinic acid proline derivatives as HIV inhibitors
US20170129916A1 (en) 2014-06-26 2017-05-11 Hetero Research Foundation Novel betulinic proline imidazole derivatives as hiv inhibitors
WO2016046786A1 (en) 2014-09-26 2016-03-31 Glaxosmithkline Intellectual Property (No.2) Limited Long acting pharmaceutical compositions
MA40886B1 (en) 2015-02-09 2020-03-31 Hetero Research Foundation Novel c-3 triterpenone with c-28 reverse amide derivatives as hiv inhibitors
US10370405B2 (en) * 2015-03-16 2019-08-06 Hetero Labs Limited C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors
WO2017115329A1 (en) * 2015-12-30 2017-07-06 Hetero Research Foundation C-3 novel triterpenone derivatives as hiv inhibitors

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11116737B1 (en) 2020-04-10 2021-09-14 University Of Georgia Research Foundation, Inc. Methods of using probenecid for treatment of coronavirus infections
US11903916B2 (en) 2020-04-10 2024-02-20 University Of Georgia Research Foundation, Inc. Methods of using probenecid for treatment of coronavirus infections

Also Published As

Publication number Publication date
MX2010007374A (en) 2010-10-05
WO2009082818A1 (en) 2009-07-09
EP2240504A1 (en) 2010-10-20
CN101977924A (en) 2011-02-16
JP2011508747A (en) 2011-03-17
AU2008342536A1 (en) 2009-07-09
CA2711420A1 (en) 2009-07-09

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