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WO2009082819A8 - Novel lupane derivatives - Google Patents

Novel lupane derivatives 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
French (fr)
Other versions
WO2009082819A1 (en
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 EP08869088A priority Critical patent/EP2250185A4/en
Priority to JP2010540997A priority patent/JP2011508748A/en
Priority to CA2711424A priority patent/CA2711424A1/en
Priority to CN2008801275273A priority patent/CN101981047A/en
Priority to MX2010007375A priority patent/MX2010007375A/en
Priority to AU2008342537A priority patent/AU2008342537A1/en
Publication of WO2009082819A1 publication Critical patent/WO2009082819A1/en
Publication of WO2009082819A8 publication Critical patent/WO2009082819A8/en
Priority to US12/830,294 priority patent/US8431556B2/en
Priority to US12/830,293 priority patent/US8269026B2/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)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (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/CA2008/002291 2008-01-03 2008-12-23 Novel lupane derivatives WO2009082819A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP08869088A EP2250185A4 (en) 2008-01-03 2008-12-23 Novel lupane derivatives
JP2010540997A JP2011508748A (en) 2008-01-03 2008-12-23 New lupine derivatives
CA2711424A CA2711424A1 (en) 2008-01-03 2008-12-23 Novel lupane derivatives
CN2008801275273A CN101981047A (en) 2008-01-03 2008-12-23 Novel lupane derivatives
MX2010007375A MX2010007375A (en) 2008-01-03 2008-12-23 Novel lupane derivatives.
AU2008342537A AU2008342537A1 (en) 2008-01-03 2008-12-23 Novel lupane derivatives
US12/830,294 US8431556B2 (en) 2008-03-26 2010-07-03 C-21-keto lupane derivatives preparation and use thereof
US12/830,293 US8269026B2 (en) 2008-01-03 2010-07-03 Lupane derivatives useful for treating HIV

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

Publications (2)

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

Family

ID=40823729

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2008/002291 WO2009082819A1 (en) 2008-01-03 2008-12-23 Novel lupane derivatives

Country Status (7)

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

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105055432A (en) * 2008-01-25 2015-11-18 奇默里克斯公司 Methods of treating viral infections
KR101733625B1 (en) * 2008-12-11 2017-05-10 시오노기세야쿠 가부시키가이샤 Synthesis of carbamoylpyridone hiv integrase inhibitors and intermediates
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
SI2932970T1 (en) 2010-01-27 2018-07-31 Viiv Healthcare Company Antiviral therapy
AU2011215986A1 (en) * 2010-02-11 2012-08-30 Glaxosmithkline Llc Derivatives of betulin
PT2534150T (en) 2010-02-12 2017-05-02 Chimerix Inc Methods of treating viral infection
WO2011139709A2 (en) 2010-04-26 2011-11-10 Chimerix, Inc. Methods of treating retroviral infections and related dosage regimes
RU2613554C2 (en) * 2011-12-14 2017-03-17 ГЛАКСОСМИТКЛАЙН ЭлЭлСи Propenoate betulin derivatives
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
US8906889B2 (en) * 2012-02-15 2014-12-09 Bristol-Myers Squibb Company C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity
BR112015013695A2 (en) 2012-12-14 2017-07-11 Glaxosmithkline Llc pharmaceutical composition and methods for treating and preventing an HIV infection
WO2014105926A1 (en) 2012-12-31 2014-07-03 Hetero Research Foundation Novel 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
JP2017528497A (en) 2014-09-26 2017-09-28 グラクソスミスクライン、インテレクチュアル、プロパティー、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ Long-acting pharmaceutical composition
BR112017009850A2 (en) * 2014-11-14 2018-01-16 Viiv Healthcare Uk No 5 Ltd compound, composition, and use of an hiv enhancer amount of a compound
MA40886B1 (en) 2015-02-09 2020-03-31 Hetero Research Foundation Novel c-3 triterpenone with c-28 reverse amide derivatives as hiv inhibitors
WO2016147099A2 (en) * 2015-03-16 2016-09-22 Hetero Research Foundation C-3 novel triterpenone with c-28 amide derivatives as hiv inhibitors
WO2017064628A1 (en) * 2015-10-13 2017-04-20 Hetero Research Foundation C-3 novel triterpenone with c-28 urea derivatives as hiv inhibitors
JP2019502728A (en) * 2016-01-20 2019-01-31 グラクソスミスクライン、インテレクチュアル、プロパティー、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ Lupine amine derivatives having HIV maturation inhibitory activity
WO2018025247A1 (en) * 2016-08-05 2018-02-08 Hetero Labs Limited C-3 novel triterpenone with c-28 diamide derivatives as hiv inhibitors
WO2018029604A1 (en) * 2016-08-08 2018-02-15 Hetero Labs Limited C-3 novel triterpenone with c-17 reverse amide derivatives as hiv inhibitors
WO2018029610A1 (en) * 2016-08-09 2018-02-15 Hetero Labs Limited C-3 novel triterpenone with c-17 n-amide derivatives as hiv inhibitors
WO2018065930A1 (en) * 2016-10-05 2018-04-12 Hetero Labs Limited C-3 triterpenone with c-17 reverse amide derivatives as hiv inhibitors
WO2018069857A1 (en) * 2016-10-12 2018-04-19 Hetero Labs Limited C-3 novel triterpenone with c-17 reverse amide heterocycle 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

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 (en) * 2000-05-23 2003-03-19 Univerzita palackeho V Olomouci Triterpenoid derivatives
WO2005112929A2 (en) * 2004-05-20 2005-12-01 Cornell Research Foundation, Inc. Anti-hiv-1 activity of betulinol derivatives
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
CN101981047A (en) 2011-02-23
EP2250185A4 (en) 2011-11-16
CA2711424A1 (en) 2009-07-09
AU2008342537A1 (en) 2009-07-09
WO2009082819A1 (en) 2009-07-09
JP2011508748A (en) 2011-03-17
EP2250185A1 (en) 2010-11-17
MX2010007375A (en) 2010-09-30

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