CA2860581A1 - Lupane triterpenoid derivatives and pharmaceutical use thereof - Google Patents

Lupane triterpenoid derivatives and pharmaceutical use thereof Download PDF

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Publication number
CA2860581A1
CA2860581A1 CA2860581A CA2860581A CA2860581A1 CA 2860581 A1 CA2860581 A1 CA 2860581A1 CA 2860581 A CA2860581 A CA 2860581A CA 2860581 A CA2860581 A CA 2860581A CA 2860581 A1 CA2860581 A1 CA 2860581A1
Authority
CA
Canada
Prior art keywords
compound
independently
mmol
optionally substituted
unsubstituted
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.)
Abandoned
Application number
CA2860581A
Other languages
English (en)
French (fr)
Inventor
Feng Lu
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.)
FENG Qiaodi
JIANGXI QINGFENG PHARMACEUTICAL Inc
Original Assignee
FENG Qiaodi
JIANGXI QINGFENG PHARMACEUTICAL 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 FENG Qiaodi, JIANGXI QINGFENG PHARMACEUTICAL Inc filed Critical FENG Qiaodi
Publication of CA2860581A1 publication Critical patent/CA2860581A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4245—Oxadiazoles
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433—Thidiazoles
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2860581A 2012-02-08 2013-01-30 Lupane triterpenoid derivatives and pharmaceutical use thereof Abandoned CA2860581A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CN201210027090.4 2012-02-08
CN201210027090 2012-02-08
CN201310014849.XA CN103242413B (zh) 2012-02-08 2013-01-15 Lupane三萜系衍生物及其药学用途
CN201310014849X 2013-01-15
PCT/CN2013/071100 WO2013117137A1 (en) 2012-02-08 2013-01-30 Lupane triterpenoid derivatives and pharmaceutical use thereof

Publications (1)

Publication Number Publication Date
CA2860581A1 true CA2860581A1 (en) 2013-08-15

Family

ID=48922317

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2860581A Abandoned CA2860581A1 (en) 2012-02-08 2013-01-30 Lupane triterpenoid derivatives and pharmaceutical use thereof

Country Status (12)

Country Link
US (1) US9428542B2 ( )
EP (1) EP2812343B1 ( )
JP (1) JP5872074B2 ( )
KR (1) KR20140126739A ( )
CN (1) CN103242413B ( )
AU (1) AU2013218441A1 ( )
BR (1) BR112014018953A8 ( )
CA (1) CA2860581A1 ( )
EA (1) EA201491479A1 ( )
HK (1) HK1202553A1 ( )
WO (1) WO2013117137A1 ( )
ZA (1) ZA201405819B ( )

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP3218387A1 (en) * 2014-11-14 2017-09-20 VIIV Healthcare UK (No.5) Limited Oxolupene derivatives
CA2967684A1 (en) * 2014-11-14 2016-05-19 VIIV Healthcare UK (No.5) Limited C17-aryl substituted betulinic acid analogs
AU2015346314B2 (en) * 2014-11-14 2018-04-12 VIIV Healthcare UK (No.5) Limited Extended betulinic acid analogs
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 (en) 2015-03-16 2016-09-22 Hetero Research Foundation C-3 novel triterpenone with c-28 amide derivatives as hiv inhibitors
WO2018029602A1 (en) * 2016-08-08 2018-02-15 Hetero Labs Limited C-3 novel triterpenone with c-28 heterocycle 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
WO2019150300A1 (en) 2018-02-02 2019-08-08 Glaxosmithkline Intellectual Property (No.2) Limited Crystalline forms of 4-(((3ar,5ar,5br,7ar,9s,11ar,11br,13as)-3a-((r)-2-((4-chlorobenzyl)(2-(dimethylamino)ethyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2h-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid
PL237998B1 (pl) 2018-05-28 2021-06-28 Narodowy Inst Lekow Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie
CN114369134A (zh) * 2020-10-15 2022-04-19 江西青峰药业有限公司 一种Lupane三萜系衍生物葡甲胺盐无定型物及其制备方法和应用
CN115504947B (zh) * 2022-08-23 2024-04-26 山东和源制药有限公司 一种呋喃酮酸的制备方法
CN116041415B (zh) * 2023-02-01 2023-08-18 吉林农业大学 一种裂环羽扇豆烷衍生物及其制备方法与应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008127364A2 (en) * 2006-10-13 2008-10-23 Myriad Genetics, Inc. Antiviral compounds and use thereof
WO2008057420A2 (en) * 2006-11-03 2008-05-15 Panacos Pharmaceuticals, Inc. Extended triterpene derivatives
WO2009073818A1 (en) * 2007-12-04 2009-06-11 Myriad Genetics, Inc. Compounds and therapeutic use thereof
AU2008342536A1 (en) * 2008-01-03 2009-07-09 Virochem Pharma Inc. Novel C-21-keto lupane derivatives preparation and use thereof
MX2010007375A (es) * 2008-01-03 2010-09-30 Virochem Pharma Inc Nuevos derivados de lupano.
EA201290632A1 (ru) * 2010-02-11 2013-03-29 ГЛАКСОСМИТКЛАЙН ЭлЭлСи Производные бетулина
JO3387B1 (ar) * 2011-12-16 2019-03-13 Glaxosmithkline Llc مشتقات بيتولين

Also Published As

Publication number Publication date
BR112014018953A2 ( ) 2017-06-20
HK1202553A1 (en) 2015-10-02
EP2812343A1 (en) 2014-12-17
EP2812343B1 (en) 2019-03-13
KR20140126739A (ko) 2014-10-31
CN103242413B (zh) 2015-08-26
EA201491479A1 (ru) 2014-11-28
ZA201405819B (en) 2015-12-23
BR112014018953A8 (pt) 2017-07-11
WO2013117137A1 (en) 2013-08-15
AU2013218441A1 (en) 2014-07-24
JP2015505545A (ja) 2015-02-23
CN103242413A (zh) 2013-08-14
EP2812343A4 (en) 2015-12-02
US9428542B2 (en) 2016-08-30
JP5872074B2 (ja) 2016-03-01
US20150011517A1 (en) 2015-01-08

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Legal Events

Date Code Title Description
FZDE Discontinued

Effective date: 20180130