WO2009082819A8 - Nouveaux dérivés de lupane - Google Patents

Nouveaux dérivés de lupane Download PDF

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Publication number
WO2009082819A8
WO2009082819A8 PCT/CA2008/002291 CA2008002291W WO2009082819A8 WO 2009082819 A8 WO2009082819 A8 WO 2009082819A8 CA 2008002291 W CA2008002291 W CA 2008002291W WO 2009082819 A8 WO2009082819 A8 WO 2009082819A8
Authority
WO
WIPO (PCT)
Prior art keywords
formula
treatment
pharmaceutically acceptable
relates
novel
Prior art date
Application number
PCT/CA2008/002291
Other languages
English (en)
Other versions
WO2009082819A1 (fr
Inventor
Christophe Moinet
Liliane Halab
Nathalie Turcotte
Monica Bubenik
Marc Courchesne
Carl Poisson
Oswy Z. Pereira
Paul Nguyen-Ba
Bingcan Liu
Nathalie Chauret
Caroline Cadilhac
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 CN2008801275273A priority Critical patent/CN101981047A/zh
Priority to AU2008342537A priority patent/AU2008342537A1/en
Priority to EP08869088A priority patent/EP2250185A4/fr
Priority to JP2010540997A priority patent/JP2011508748A/ja
Priority to CA2711424A priority patent/CA2711424A1/fr
Priority to MX2010007375A priority patent/MX2010007375A/es
Publication of WO2009082819A1 publication Critical patent/WO2009082819A1/fr
Publication of WO2009082819A8 publication Critical patent/WO2009082819A8/fr
Priority to US12/830,293 priority patent/US8269026B2/en
Priority to US12/830,294 priority patent/US8431556B2/en

Links

Classifications

    • 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
    • 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
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05—Dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/55—Protease inhibitors
    • 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)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Immunology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Communicable Diseases (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • AIDS & HIV (AREA)
  • Molecular Biology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La présente invention concerne des composés de 21-céto triterpènes de formule (I) : R1, X, et Y étant tels que définis dans la description, et des sels et des solvates de ceux-ci pharmaceutiquement acceptables. Ces composés présentent une activité anti-VIH significative. L'invention concerne également des procédés de prévention ou de traitement des infections par le VIH par administration de quantités thérapeutiquement efficaces d'un composé de formule (I), ou d'un sel ou solvate pharmaceutiquement acceptable de celui-ci, à un sujet ayant besoin d'un tel traitement.
PCT/CA2008/002291 2008-01-03 2008-12-23 Nouveaux dérivés de lupane WO2009082819A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CN2008801275273A CN101981047A (zh) 2008-01-03 2008-12-23 新的羽扇烷衍生物
AU2008342537A AU2008342537A1 (en) 2008-01-03 2008-12-23 Novel lupane derivatives
EP08869088A EP2250185A4 (fr) 2008-01-03 2008-12-23 Nouveaux dérivés de lupane
JP2010540997A JP2011508748A (ja) 2008-01-03 2008-12-23 新規のルパン誘導体
CA2711424A CA2711424A1 (fr) 2008-01-03 2008-12-23 Nouveaux derives de lupane
MX2010007375A MX2010007375A (es) 2008-01-03 2008-12-23 Nuevos derivados de lupano.
US12/830,293 US8269026B2 (en) 2008-01-03 2010-07-03 Lupane derivatives useful for treating HIV
US12/830,294 US8431556B2 (en) 2008-03-26 2010-07-03 C-21-keto lupane derivatives preparation and use thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US1875908P 2008-01-03 2008-01-03
US61/018,759 2008-01-03
US3966008P 2008-03-26 2008-03-26
US61/039,660 2008-03-26

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/830,293 Continuation US8269026B2 (en) 2008-01-03 2010-07-03 Lupane derivatives useful for treating HIV
US12/830,294 Continuation US8431556B2 (en) 2008-03-26 2010-07-03 C-21-keto lupane derivatives preparation and use thereof

Publications (2)

Publication Number Publication Date
WO2009082819A1 WO2009082819A1 (fr) 2009-07-09
WO2009082819A8 true WO2009082819A8 (fr) 2009-10-22

Family

ID=40823729

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2008/002291 WO2009082819A1 (fr) 2008-01-03 2008-12-23 Nouveaux dérivés de lupane

Country Status (7)

Country Link
EP (1) EP2250185A4 (fr)
JP (1) JP2011508748A (fr)
CN (1) CN101981047A (fr)
AU (1) AU2008342537A1 (fr)
CA (1) CA2711424A1 (fr)
MX (1) MX2010007375A (fr)
WO (1) WO2009082819A1 (fr)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2254582B1 (fr) * 2008-01-25 2016-01-20 Chimerix, Inc. Méthodes de traitement d'infections virales
RU2527451C2 (ru) * 2008-12-11 2014-08-27 Вайв Хелткер Компани Синтез карбамоилпиридоновых ингибиторов интегразы вич и промежуточных соединений
US8802727B2 (en) 2009-07-14 2014-08-12 Hetero Research Foundation, Hetero Drugs Limited Pharmaceutically acceptable salts of betulinic acid derivatives
US9067966B2 (en) * 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
DK3494972T3 (da) * 2010-01-27 2024-01-29 Viiv Healthcare Co Kombinationer af dolutegravir og lamivudin til behandling af HIV-infektion
AU2011215986A1 (en) * 2010-02-11 2012-08-30 Glaxosmithkline Llc Derivatives of betulin
US9006218B2 (en) 2010-02-12 2015-04-14 Chimerix Inc. Nucleoside phosphonate salts
EP2563367A4 (fr) 2010-04-26 2013-12-04 Chimerix Inc Méthodes de traitement d'infections rétrovirales et régimes posologiques associés
RU2613554C2 (ru) * 2011-12-14 2017-03-17 ГЛАКСОСМИТКЛАЙН ЭлЭлСи Пропеноатные производные бетулина
JO3387B1 (ar) 2011-12-16 2019-03-13 Glaxosmithkline Llc مشتقات بيتولين
CN103242413B (zh) * 2012-02-08 2015-08-26 江西青峰药业有限公司 Lupane三萜系衍生物及其药学用途
US8906889B2 (en) * 2012-02-15 2014-12-09 Bristol-Myers Squibb Company C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity
WO2014093941A1 (fr) 2012-12-14 2014-06-19 Glaxosmithkline Llc Compositions pharmaceutiques
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
CN106999425A (zh) 2014-09-26 2017-08-01 葛兰素史克知识产权第二有限公司 长效药物组合物
RU2017118489A (ru) * 2014-11-14 2018-12-14 ВАЙВ ХЕЛТКЕР ЮКей (N5) ЛИМИТЕД Оксолупеновые производные
MA40886B1 (fr) 2015-02-09 2020-03-31 Hetero Research Foundation Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih
WO2016147099A2 (fr) * 2015-03-16 2016-09-22 Hetero Research Foundation Nouveaux triterpénone c-3 avec des dérivés amide c-28 servant d'inhibiteurs de vih
US10669305B2 (en) * 2015-10-13 2020-06-02 Hetero Labs Limited C-3 novel triterpenone with C-28 urea derivatives as HIV inhibitors
US20190023733A1 (en) * 2016-01-20 2019-01-24 Glaxosmithkline Intellectual Property (No.2) Limited Amine derivatives of lupanes with hiv maturation inhibitory activity
WO2018025247A1 (fr) * 2016-08-05 2018-02-08 Hetero Labs Limited Nouvelle triterpénone en c-3 avec des dérivés de diamide en c-28 en tant qu'inhibiteurs du vih
WO2018029604A1 (fr) * 2016-08-08 2018-02-15 Hetero Labs Limited Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-17 en tant qu'inhibiteurs du vih
WO2018029610A1 (fr) * 2016-08-09 2018-02-15 Hetero Labs Limited Nouvelle triterpénone en c-3 avec des dérivés de n-amide en c-17 en tant qu'inhibiteurs du vih
WO2018065930A1 (fr) * 2016-10-05 2018-04-12 Hetero Labs Limited Triterpénone en c-3 avec des dérivés amides inversés en c-17 en tant qu'inhibiteurs du vih
WO2018069857A1 (fr) * 2016-10-12 2018-04-19 Hetero Labs Limited Nouvelle triterpénone en c-3 à dérivés hétérocycliques d'amide inverse en c-17 utilisés comme inhibiteurs du vih
US11116737B1 (en) 2020-04-10 2021-09-14 University Of Georgia Research Foundation, Inc. Methods of using probenecid for treatment of coronavirus infections

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0012528D0 (en) * 2000-05-23 2000-07-12 Univ Palackeho Triterpenoid derivatives
EP1292562A1 (fr) * 2000-05-23 2003-03-19 Univerzita palackeho V Olomouci Derives triterpenoides
WO2005112929A2 (fr) * 2004-05-20 2005-12-01 Cornell Research Foundation, Inc. Activite anti vih-1 de derives de betulinol
TW200628161A (en) * 2004-11-12 2006-08-16 Panacos Pharmaceuticals Inc Novel betulin derivatives, preparation thereof and use thereof

Also Published As

Publication number Publication date
MX2010007375A (es) 2010-09-30
AU2008342537A1 (en) 2009-07-09
EP2250185A4 (fr) 2011-11-16
WO2009082819A1 (fr) 2009-07-09
JP2011508748A (ja) 2011-03-17
EP2250185A1 (fr) 2010-11-17
CA2711424A1 (fr) 2009-07-09
CN101981047A (zh) 2011-02-23

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