CA2826113C - C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity - Google Patents

C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity Download PDF

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Publication number
CA2826113C
CA2826113C CA2826113A CA2826113A CA2826113C CA 2826113 C CA2826113 C CA 2826113C CA 2826113 A CA2826113 A CA 2826113A CA 2826113 A CA2826113 A CA 2826113A CA 2826113 C CA2826113 C CA 2826113C
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CA
Canada
Prior art keywords
alkyl
compound
cyclopenta
octadecahydro
substituted
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.)
Active
Application number
CA2826113A
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English (en)
French (fr)
Other versions
CA2826113A1 (en
Inventor
Alicia Regueiro-Ren
Zheng Liu
Jacob Swidorski
Ny Sin
Brian Lee Venables
Sing-Yuen Sit
Yan Chen
Jie Chen
Nicholas A. Meanwell
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.)
ViiV Healthcare UK No 4 Ltd
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ViiV Healthcare UK No 4 Ltd
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Application filed by ViiV Healthcare UK No 4 Ltd filed Critical ViiV Healthcare UK No 4 Ltd
Publication of CA2826113A1 publication Critical patent/CA2826113A1/en
Application granted granted Critical
Publication of CA2826113C publication Critical patent/CA2826113C/en
Active legal-status Critical Current
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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
    • 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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • 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
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2826113A 2011-01-31 2012-01-27 C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity Active CA2826113C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161437893P 2011-01-31 2011-01-31
US61/437,893 2011-01-31
PCT/US2012/022852 WO2012106190A1 (en) 2011-01-31 2012-01-27 C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity

Publications (2)

Publication Number Publication Date
CA2826113A1 CA2826113A1 (en) 2012-08-09
CA2826113C true CA2826113C (en) 2018-09-04

Family

ID=45567147

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2826113A Active CA2826113C (en) 2011-01-31 2012-01-27 C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity

Country Status (25)

Country Link
US (3) US8846647B2 (enExample)
EP (1) EP2670765B1 (enExample)
JP (1) JP6001560B2 (enExample)
KR (1) KR101886467B1 (enExample)
CN (1) CN103429607B (enExample)
AR (1) AR085053A1 (enExample)
AU (1) AU2012212509B2 (enExample)
BR (1) BR112013019419A2 (enExample)
CA (1) CA2826113C (enExample)
CL (1) CL2013002185A1 (enExample)
CO (1) CO6751275A2 (enExample)
EA (1) EA022470B1 (enExample)
ES (1) ES2653847T3 (enExample)
IL (1) IL227678B (enExample)
MA (1) MA34909B1 (enExample)
MY (1) MY162186A (enExample)
PE (1) PE20141152A1 (enExample)
PH (1) PH12013501528A1 (enExample)
PT (1) PT2670765T (enExample)
SG (1) SG192144A1 (enExample)
TN (1) TN2013000321A1 (enExample)
TW (1) TWI628188B (enExample)
UY (1) UY33886A (enExample)
WO (1) WO2012106190A1 (enExample)
ZA (1) ZA201306546B (enExample)

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RS58392B1 (sr) 2008-04-18 2019-04-30 Reata Pharmaceuticals Inc Antioksidantni modulatori inflamacije: derivati oleanoličke kiseline sa amino i drugim modifikacijama na c-17
HUE033288T2 (en) 2008-04-18 2017-11-28 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: C-17 homologated oleic acid derivatives
ES2653717T3 (es) 2010-12-17 2018-02-08 Reata Pharmaceuticals, Inc. Pirazolil- y pirimidinil-enonas tricíclicas como moduladores antioxidantes de la inflamación
HRP20151212T1 (hr) * 2011-01-31 2015-12-04 Bristol-Myers Squibb Company C-28 AMINI C-3 MODIFICIRANIH DERIVATA BETULINSKE KISELINE KAO INHIBITORI SAZRIJEVANJA HIV-a P
EA026847B1 (ru) 2011-03-11 2017-05-31 Рита Фармасьютикалз, Инк. C4-монометилтритерпеноидные производные и способы их применения
EP2758419B8 (en) 2011-09-21 2017-04-19 VIIV Healthcare UK (No.5) Limited Novel betulinic acid derivatives with antiviral activity
US8906889B2 (en) 2012-02-15 2014-12-09 Bristol-Myers Squibb Company C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity
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US9512094B2 (en) 2012-09-10 2016-12-06 Reata Pharmaceuticals, Inc. C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
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EA027371B1 (ru) * 2013-02-06 2017-07-31 Бристол-Майерс Сквибб Компани C-19 модифицированные тритерпеноиды с ингибиторной активностью созревания вич
BR112015019590A2 (pt) * 2013-02-25 2017-07-18 Bristol Myers Squibb Co derivados de ácido betulínico modificado com c-3 alquila e alquenila úteis no tratamento de hiv
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US9920090B2 (en) 2014-06-19 2018-03-20 VIIV Healthcare UK (No.5) Limited Betulinic acid derivatives with HIV maturation inhibitory activity
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AU2015346303B2 (en) 2014-11-14 2018-03-15 VIIV Healthcare UK (No.5) Limited Oxolupene derivatives
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RU2018105352A (ru) 2015-07-28 2019-08-29 ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед Производные бетулина для предупреждения или лечения ВИЧ-инфекций
KR20180028534A (ko) 2015-07-28 2018-03-16 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 Hiv 감염을 예방하거나 치료하기 위한 베투인 유도체
WO2017025901A1 (en) * 2015-08-11 2017-02-16 Hetero Research Foundation Novel c28-analogues with c3-modifications of triterpene derivatives as hiv inhibitors
BR112018005861B1 (pt) 2015-09-23 2022-11-22 Reata Pharmaceuticals, Inc Compostos derivados de ácido oleanólico modificado com c4 para a inibição de il-17, composição farmacêutica e usos terapêuticos dos ditos compostos
RU2018112958A (ru) 2015-09-24 2019-10-28 ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед Соединения с ингибирующей созревание ВИЧ активностью
RU2018116772A (ru) 2015-11-20 2019-12-20 ВАЙВ ХЕЛТКЕР ЮКей (N4) ЛИМИТЕД Композиции ингибитора созревания ВИЧ
CN108699103A (zh) * 2016-01-20 2018-10-23 葛兰素史克知识产权第二有限公司 具有hiv成熟抑制活性的羽扇烷类的胺衍生物
AR107512A1 (es) * 2016-02-04 2018-05-09 VIIV HEALTHCARE UK Nº 5 LTD Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1
EP3478703A1 (en) * 2016-06-30 2019-05-08 ViiV Healthcare UK (No.5) Limited Triterpenoid inhibitors of human immunodeficiency virus replication
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Also Published As

Publication number Publication date
CA2826113A1 (en) 2012-08-09
TN2013000321A1 (en) 2015-01-20
AU2012212509B2 (en) 2016-01-21
CN103429607A (zh) 2013-12-04
PE20141152A1 (es) 2014-09-22
KR101886467B1 (ko) 2018-08-07
US8846647B2 (en) 2014-09-30
ES2653847T3 (es) 2018-02-09
CO6751275A2 (es) 2013-09-16
JP6001560B2 (ja) 2016-10-05
SG192144A1 (en) 2013-08-30
PT2670765T (pt) 2018-01-08
IL227678B (en) 2018-04-30
CN103429607B (zh) 2016-02-17
MA34909B1 (fr) 2014-02-01
US20130035318A1 (en) 2013-02-07
KR20140016279A (ko) 2014-02-07
AR085053A1 (es) 2013-08-07
EP2670765A1 (en) 2013-12-11
UY33886A (es) 2012-07-31
PH12013501528A1 (en) 2013-09-16
EA022470B1 (ru) 2016-01-29
NZ614871A (en) 2014-06-27
US20140343000A1 (en) 2014-11-20
AU2012212509A1 (en) 2013-09-19
TW201309717A (zh) 2013-03-01
TWI628188B (zh) 2018-07-01
EA201391127A1 (ru) 2013-12-30
US20160151387A1 (en) 2016-06-02
WO2012106190A1 (en) 2012-08-09
ZA201306546B (en) 2015-03-25
MY162186A (en) 2017-05-31
JP2014503595A (ja) 2014-02-13
CL2013002185A1 (es) 2013-12-27
EP2670765B1 (en) 2017-10-18
BR112013019419A2 (pt) 2019-12-03
IL227678A0 (en) 2013-09-30

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