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

Info

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
Authority
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
Other languages
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
Original Assignee
ViiV Healthcare UK No 4 Ltd
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 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
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J63/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/18Antivirals for RNA viruses for HIV
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J63/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008Expansion 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)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • AIDS & HIV (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)
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 (2)
EP (1) EP2670765B1 (2)
JP (1) JP6001560B2 (2)
KR (1) KR101886467B1 (2)
CN (1) CN103429607B (2)
AR (1) AR085053A1 (2)
AU (1) AU2012212509B2 (2)
BR (1) BR112013019419A2 (2)
CA (1) CA2826113C (2)
CL (1) CL2013002185A1 (2)
CO (1) CO6751275A2 (2)
EA (1) EA022470B1 (2)
ES (1) ES2653847T3 (2)
IL (1) IL227678B (2)
MA (1) MA34909B1 (2)
MY (1) MY162186A (2)
PE (1) PE20141152A1 (2)
PH (1) PH12013501528A1 (2)
PT (1) PT2670765T (2)
SG (1) SG192144A1 (2)
TN (1) TN2013000321A1 (2)
TW (1) TWI628188B (2)
UY (1) UY33886A (2)
WO (1) WO2012106190A1 (2)
ZA (1) ZA201306546B (2)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5529851B2 (ja) 2008-04-18 2014-06-25 リアタ ファーマシューティカルズ インコーポレイテッド 抗酸化炎症モジュレーター:c−17においてアミノ改変およびその他の改変を加えたオレアノール酸誘導体
KR101713140B1 (ko) 2008-04-18 2017-03-08 리타 파마슈티컬스 잉크. C-환에서 포화된 산화방지성 염증 조절제 올레아놀산 유도체
MX2010011439A (es) 2008-04-18 2011-01-25 Reata Pharmaceuticals Inc Moduladores de inflamacion antioxidantes: derivados del acido oleanolico homologacion c-17.
WO2009146218A2 (en) 2008-04-18 2009-12-03 Reata Pharmaceuticals, Inc. Compounds including an anti-inflammatory pharmacore and methods of use
CN103596929B (zh) 2010-12-17 2016-10-19 里亚塔医药公司 作为抗氧化发炎调节剂的吡唑及嘧啶三环烯酮
HUE026371T2 (en) * 2011-01-31 2016-05-30 Bristol Myers Squibb Co C-28 amines from modified C-3 betulinic acid derivatives as anti-HIV matrices
MX348862B (es) 2011-03-11 2017-07-03 Reata Pharmaceuticals Inc Derivados c4-monometil triterpenoides y sus metodos de uso.
MX2014002936A (es) 2011-09-21 2014-04-25 Bristol Myers Squibb Co Nuevos derivados de acido betulinico con actividad antiviral.
US8906889B2 (en) * 2012-02-15 2014-12-09 Bristol-Myers Squibb Company C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity
TWI623548B (zh) 2012-04-27 2018-05-11 瑞塔醫藥有限責任公司 齊墩果酸(bardoxolone methyl)之2,2-二氟基丙醯胺衍生物、多晶型及其使用方法
US8889854B2 (en) 2012-05-07 2014-11-18 Bristol-Myers Squibb Company C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity
WO2013188818A1 (en) 2012-06-15 2013-12-19 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
BR112015003101B1 (pt) * 2012-08-15 2022-06-14 Glaxo Group Limited Processo para a preparação de um composto
WO2014040073A1 (en) 2012-09-10 2014-03-13 Reata Pharmaceuticals, Inc. C13-hydroxy derivatives of oleanolic acid and methods of use thereof
US9512094B2 (en) 2012-09-10 2016-12-06 Reata Pharmaceuticals, Inc. C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
JP6243428B2 (ja) 2012-09-10 2017-12-06 リアタ ファーマシューティカルズ インコーポレイテッド オレアノール酸のc17−アルカンジイルおよびアルケンジイル誘導体ならびにその使用方法
JP6186010B2 (ja) * 2013-02-06 2017-08-23 ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company Hiv成熟阻害活性を有するc−19修飾トリテルペノイド類
KR20150121712A (ko) * 2013-02-25 2015-10-29 브리스톨-마이어스 스큅 컴퍼니 Hiv의 치료에 유용한 c-3 알킬 및 알케닐 개질된 베툴린산 유도체
UY36070A (es) 2014-04-11 2015-10-30 Bristol Myers Squibb Company Una Corporación Del Estado De Delaware Triterpenoides con actividad inhibidora de la maduración de hiv
WO2015195776A1 (en) 2014-06-19 2015-12-23 Bristol-Myers Squibb Company Betulinic acid derivatives with hiv maturation inhibitory activity
US9969767B2 (en) 2014-11-14 2018-05-15 VIIV Healthcare UK (No.5) Limited Oxolupene derivatives
CN107250152A (zh) * 2014-11-14 2017-10-13 Viiv保健英国第五有限公司 C17‑芳基取代的桦木酸类似物
EP3283467A1 (en) * 2015-04-14 2018-02-21 VIIV Healthcare UK(No.4) Limited Methods of producing an hiv maturation inhibitor
US20180194799A1 (en) 2015-07-28 2018-07-12 Glaxosmithkline Intellectual Property (No.2) Limited Betuin derivatives for preventing or treating hiv infections
WO2017017609A1 (en) 2015-07-28 2017-02-02 Glaxosmithkline Intellectual Property (No.2) Limited Betuin derivatives for preventing or treating hiv infections
WO2017025901A1 (en) * 2015-08-11 2017-02-16 Hetero Research Foundation Novel c28-analogues with c3-modifications of triterpene derivatives as hiv inhibitors
JP7074674B2 (ja) 2015-09-23 2022-05-24 リアタ ファーマシューティカルズ インコーポレイテッド Il-17の阻害及び他の使用のためのc4修飾オレアノール酸誘導体
KR20180054826A (ko) 2015-09-24 2018-05-24 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 Hiv 성숙 억제 활성을 갖는 화합물
EP3377177A2 (en) 2015-11-20 2018-09-26 VIIV Healthcare UK(No.4) Limited Hiv maturation inhibitor formulations
EP3405474A1 (en) * 2016-01-20 2018-11-28 Glaxosmithkline Intellectual Property (No. 2) Limited Amine derivatives of lupanes with hiv maturation inhibitory activity
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
WO2018044822A1 (en) * 2016-08-31 2018-03-08 Viiv Healthcare Company Combinations and uses and treatments thereof
MX2020001412A (es) 2017-08-04 2020-08-03 Ardelyx Inc Compuestos y métodos para tratar la hiperpotasemia.
JP6926939B2 (ja) * 2017-10-23 2021-08-25 東京エレクトロン株式会社 半導体装置の製造方法
JP6977474B2 (ja) * 2017-10-23 2021-12-08 東京エレクトロン株式会社 半導体装置の製造方法
ES2970042T3 (es) 2018-04-24 2024-05-24 Viiv Healthcare Uk No 5 Ltd Compuestos con actividad inhibidora de la maduración del VIH
PL237998B1 (pl) 2018-05-28 2021-06-28 Narodowy Inst Lekow Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie
US12060340B2 (en) 2018-06-20 2024-08-13 Reata Pharmaceuticals, Inc Cysteine-dependent inverse agonists of nuclear receptors ROR-gamma/ROR-gamma-t and methods of treating diseases or disorders therewith
PH12021551892A1 (en) 2019-02-07 2022-08-01 Ardelyx Inc Glycyrrhetinic acid derivatives for use in treating hyperkalemia
AU2020222299C1 (en) 2019-02-11 2024-05-16 Hetero Labs Limited Novel triterpene derivatives as HIV inhibitors
EP3999522B1 (en) 2019-07-19 2025-09-03 Reata Pharmaceuticals, Inc. C17 polar-substituted heteroaromatic synthetic triterpenoids and methods of use thereof
GB2598300A (en) * 2020-08-21 2022-03-02 Univ Durham Cross-linking method and applications in bioconjugation

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5413999A (en) 1991-11-08 1995-05-09 Merck & Co., Inc. HIV protease inhibitors useful for the treatment of AIDS
US5869535A (en) 1995-03-21 1999-02-09 The Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma
US5962527A (en) 1995-03-21 1999-10-05 The Board Of Trustees Of The University Of Illinois Method and composition for treating cancers
US5679828A (en) 1995-06-05 1997-10-21 Biotech Research Labs, Inc. Betulinic acid and dihydrobetulinic acid derivatives and uses therefor
US20020137755A1 (en) 2000-12-04 2002-09-26 Bilodeau Mark T. Tyrosine kinase inhibitors
US20040110785A1 (en) 2001-02-02 2004-06-10 Tao Wang Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives
US7365221B2 (en) 2002-09-26 2008-04-29 Panacos Pharmaceuticals, Inc. Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof
WO2004089357A2 (en) 2003-04-02 2004-10-21 Regents Of The University Of Minnesota Anti-fungal formulation of triterpene and essential oil
US7745625B2 (en) 2004-03-15 2010-06-29 Bristol-Myers Squibb Company Prodrugs of piperazine and substituted piperidine antiviral agents
BRPI0508854A (pt) 2004-03-17 2007-08-28 Panacos Pharmaceuticals Inc sais farmacêuticos de ácido-3-o-(3',3'-dimetilsuccinil) betulìnico
TW200628161A (en) * 2004-11-12 2006-08-16 Panacos Pharmaceuticals Inc Novel betulin derivatives, preparation thereof and use thereof
US8067620B2 (en) 2005-05-04 2011-11-29 Medicines For Malaria Venture Mmv Dispiro 1,2,4-trioxolane antimalarials
WO2008127364A2 (en) * 2006-10-13 2008-10-23 Myriad Genetics, Inc. Antiviral compounds and use thereof
WO2008115281A2 (en) 2006-10-16 2008-09-25 Myriad Genetics, Inc. Compounds for treating viral infections
CA2714049A1 (en) 2008-02-14 2009-08-20 Virochem Pharma Inc. Novel 17.beta. lupane derivatives
US9067966B2 (en) * 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
RS54239B1 (sr) * 2010-06-04 2015-12-31 Bristol-Myers Squibb Company C-28 amidi modifikovanih derivata c-3 betulinske kiseline kao inhibitori sazrevanja hiv-a
US8754068B2 (en) * 2010-06-04 2014-06-17 Bristol-Myers Squibb Company Modified C-3 betulinic acid derivatives as HIV maturation inhibitors

Also Published As

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

Similar Documents

Publication Publication Date Title
CA2826113C (en) C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity
CA2801491C (en) C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors
EP2670764B1 (en) C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors
CA2872891C (en) C-17 bicyclic amines of triterpenoids with hiv maturation inhibitory activity
AU2014215468B2 (en) C-19 modified triterpenoids with HIV maturation inhibitory activity
AU2014218754B2 (en) C-3 alkyl and alkenyl modified betulinic acid derivatives useful in the treatment of HIV
CA2864656A1 (en) C-3 cycloalkenyl triterpenoids with hiv maturation inhibitory activity
CA2967679A1 (en) Oxolupene derivatives
NZ614871B2 (en) C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity
CA2967601A1 (en) Extended betulinic acid analogs
CA2967684A1 (en) C17-aryl substituted betulinic acid analogs

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20161011

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 13TH ANNIV.) - STANDARD

Year of fee payment: 13

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241223

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241223

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241223

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260310