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

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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
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
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 CN2008801275023A priority Critical patent/CN101977924A/en
Priority to MX2010007374A priority patent/MX2010007374A/en
Priority to AU2008342536A priority patent/AU2008342536A1/en
Priority to JP2010540996A priority patent/JP2011508747A/en
Priority to EP08867782A priority patent/EP2240504A1/en
Priority to CA2711420A priority patent/CA2711420A1/en
Publication of WO2009082818A1 publication Critical patent/WO2009082818A1/en
Publication of WO2009082818A8 publication Critical patent/WO2009082818A8/en

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

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 WO2009082818A1 (en)

Priority Applications (6)

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

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 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)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8993542B2 (en) * 2008-01-25 2015-03-31 Chimerix Inc. Methods of treating viral infections
US9067966B2 (en) 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
EA202190473A3 (en) 2010-01-27 2021-12-31 Вайв Хелткер Компани ANTIVIRAL THERAPY
WO2011100308A1 (en) * 2010-02-11 2011-08-18 Glaxosmithkline Llc Derivatives of betulin
EP2534150B1 (en) 2010-02-12 2017-04-05 Chimerix, Inc. Methods of treating viral infection
AU2011248620B2 (en) 2010-04-26 2015-11-26 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
JO3387B1 (en) 2011-12-16 2019-03-13 Glaxosmithkline Llc 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
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
CN104902905A (en) 2012-12-14 2015-09-09 葛兰素史克有限责任公司 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
AU2015323321A1 (en) 2014-09-26 2017-04-13 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
US11116737B1 (en) 2020-04-10 2021-09-14 University Of Georgia Research Foundation, Inc. Methods of using probenecid for treatment of coronavirus infections

Also Published As

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

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