CA2882417C - C17-heteroaryl derivatives of oleanolic acid and methods of use thereof - Google Patents

C17-heteroaryl derivatives of oleanolic acid and methods of use thereof Download PDF

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Publication number
CA2882417C
CA2882417C CA2882417A CA2882417A CA2882417C CA 2882417 C CA2882417 C CA 2882417C CA 2882417 A CA2882417 A CA 2882417A CA 2882417 A CA2882417 A CA 2882417A CA 2882417 C CA2882417 C CA 2882417C
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Canada
Prior art keywords
compound
groups
carbon
acid
compounds
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CA2882417A
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English (en)
French (fr)
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CA2882417A1 (en
Inventor
Xin Jiang
Christopher F. Bender
Melean Visnick
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Reata Pharmaceuticals Inc
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Reata Pharmaceuticals Inc
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Publication of CA2882417A1 publication Critical patent/CA2882417A1/en
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Publication of CA2882417C publication Critical patent/CA2882417C/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D271/00Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/101,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00General protective or antinoxious agents
    • A61P39/06Free radical scavengers or antioxidants
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D271/00Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/061,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Biochemistry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Lubricants (AREA)
  • Steroid Compounds (AREA)
  • Epidemiology (AREA)
CA2882417A 2012-09-10 2013-09-10 C17-heteroaryl derivatives of oleanolic acid and methods of use thereof Active CA2882417C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261699199P 2012-09-10 2012-09-10
US61/699,199 2012-09-10
PCT/US2013/059015 WO2014040056A1 (en) 2012-09-10 2013-09-10 C17-heteroaryl derivatives of oleanolic acid and methods of use thereof

Publications (2)

Publication Number Publication Date
CA2882417A1 CA2882417A1 (en) 2014-03-13
CA2882417C true CA2882417C (en) 2021-04-20

Family

ID=49253401

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2882417A Active CA2882417C (en) 2012-09-10 2013-09-10 C17-heteroaryl derivatives of oleanolic acid and methods of use thereof

Country Status (28)

Country Link
US (1) US20140088163A1 (enExample)
EP (1) EP2892911B1 (enExample)
JP (1) JP6272870B2 (enExample)
KR (1) KR102237364B1 (enExample)
CN (1) CN104768965B (enExample)
AU (1) AU2013312102B2 (enExample)
BR (1) BR112015005200B1 (enExample)
CA (1) CA2882417C (enExample)
CY (1) CY1119762T1 (enExample)
DK (1) DK2892911T3 (enExample)
EA (1) EA029069B1 (enExample)
ES (1) ES2644615T3 (enExample)
HR (1) HRP20171565T1 (enExample)
HU (1) HUE036797T2 (enExample)
IL (1) IL237638B (enExample)
IN (1) IN2015DN01547A (enExample)
LT (1) LT2892911T (enExample)
ME (1) ME02911B (enExample)
MX (1) MX366954B (enExample)
NZ (1) NZ705213A (enExample)
PL (1) PL2892911T3 (enExample)
PT (1) PT2892911T (enExample)
RS (1) RS56563B1 (enExample)
SG (1) SG11201501800UA (enExample)
SI (1) SI2892911T1 (enExample)
SM (1) SMT201700501T1 (enExample)
WO (1) WO2014040056A1 (enExample)
ZA (1) ZA201501203B (enExample)

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LT2252283T (lt) 2008-01-11 2019-03-25 Reata Pharmaceuticals, Inc. Sintetiniai triterpenoidai ir jų panaudojimo būdai gydant ligą
KR101735807B1 (ko) 2008-04-18 2017-05-15 리타 파마슈티컬스 잉크. C-17에 아미노 및 기타 변형을 갖는 올레아놀산 유도체를 포함하는 항산화 염증 조절제
CA2721665C (en) 2008-04-18 2017-01-24 Reata Pharmaceuticals, Inc. Compounds including an anti-inflammatory pharmacore and methods of use
HUE038046T2 (hu) 2010-12-17 2018-09-28 Reata Pharmaceuticals Inc Antioxidáns gyulladáscsökkentõ pirazolil és pirimidinil triciklusos enonok
ME02926B (me) 2012-04-27 2018-04-20 Reata Pharmaceuticals Inc 2,2-difluoropropionamidni derivati bardoksolon metila, polimorfni oblici i postupci za njihovu upotrebu
US9556222B2 (en) 2012-06-15 2017-01-31 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators 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
CR20150117A (es) 2012-09-10 2016-10-10 Reata Pharmaceuticals Inc Derivados c17-alcandilo y alquendilo del ácido oleanólico y sus métodos de uso
UY39092A (es) 2013-04-24 2021-03-26 Abbvie Inc Derivados de 2,2-difluoropropanamida y metil bardoxolona, formas polimórficas y métodos de uso
US11059792B2 (en) 2015-02-12 2021-07-13 Reata Pharmaceuticals, Inc. Imidazolyl tricyclic enones as antioxidant inflammation modulators
EA201890767A1 (ru) 2015-09-23 2019-09-30 Рита Фармасьютикалз, Инк. C4-модифицированные производные олеаноловой кислоты для ингибирования il-17 и других применений
MA46749A (fr) 2016-11-08 2019-09-18 Reata Pharmaceuticals Inc Méthodes de traitement du syndrome d'alport à l'aide d'un méthyle de bardoxolone ou d'analogues de ce dernier
CN106632574B (zh) * 2016-12-07 2018-05-29 广东天键生物科技有限公司 一种化合物、其制备方法及用途
TWI831738B (zh) 2016-12-16 2024-02-11 美商瑞塔醫藥有限責任公司 用於抑制RORγ及其他用途的嘧啶三環烯酮衍生物
RU2020113341A (ru) 2017-09-14 2021-10-15 Феникс Байотекнолоджи, Инк. Способ и композиция для лечения вирусной инфекции
EP3681477A4 (en) 2017-09-14 2021-06-09 Phoenix Biotechnology, Inc. PROCEDURES AND IMPROVED COMPOSITION FOR TREATMENT OF TREITERPEN RESPONSIBLE CONDITIONS, DISEASES, OR DISORDERS
BR112020025605A2 (pt) 2018-06-15 2021-03-23 Reata Pharmaceuticals, Inc. compostos de pirazol e imidazol para inibição de il-17 e rorgama
EP3810141A1 (en) 2018-06-20 2021-04-28 Reata Pharmaceuticals, Inc. Cysteine-dependent inverse agonists of nuclear receptors ror-gamma/ror-gamma-t and methods of treating diseases or disorders therewith
MX2021003643A (es) * 2018-09-28 2021-08-19 Sichuan Haisco Pharmaceutical Co Ltd Derivados de terpenoides y usos de los mismos.
KR102891865B1 (ko) * 2019-07-19 2025-11-26 리아타 파마슈티컬즈, 아이엔씨. C17 극성-치환된 헤테로방향족 합성 트리터페노이드 및 그의 사용 방법
JP7153083B2 (ja) 2020-03-31 2022-10-13 フェニックス・バイオテクノロジー・インコーポレイテッド コロナウイルス感染を治療するための方法および組成物
EP4295854A3 (en) 2020-03-31 2024-04-03 Phoenix Biotechnology, Inc. Method and compositions for treating coronavirus infection
JP7214696B2 (ja) * 2020-10-01 2023-01-30 一般財団法人 化学物質評価研究機構 新規in vitro皮膚感作性試験法
WO2022126129A1 (en) 2020-12-11 2022-06-16 Reata Pharmaceuticals, Inc. Synthetic triterpenoids for use in therapy
MX2023008454A (es) 2021-01-18 2023-08-07 Reata Pharmaceuticals Inc Derivados sintéticos de ácido ursólico y métodos de uso de estos.

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6326507B1 (en) * 1998-06-19 2001-12-04 Trustees Of Dartmouth College Therapeutic compounds and methods of use
EP1507541A4 (en) * 2002-05-13 2009-06-03 Dartmouth College HEMMER AND APPLICATION METHOD THEREFOR
LT2252283T (lt) 2008-01-11 2019-03-25 Reata Pharmaceuticals, Inc. Sintetiniai triterpenoidai ir jų panaudojimo būdai gydant ligą
HUE033288T2 (en) 2008-04-18 2017-11-28 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: C-17 homologated oleic acid derivatives
WO2009129545A1 (en) * 2008-04-18 2009-10-22 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring
WO2009146216A2 (en) 2008-04-18 2009-12-03 Reata Pharmaceuticals. Inc. Antioxidant inflammation modulators: novel derivatives of oleanolic acid
KR101735807B1 (ko) 2008-04-18 2017-05-15 리타 파마슈티컬스 잉크. C-17에 아미노 및 기타 변형을 갖는 올레아놀산 유도체를 포함하는 항산화 염증 조절제
CN103619866B (zh) * 2011-03-11 2016-06-22 里亚塔医药公司 C4-一甲基三萜系化合物的衍生物及其使用方法
US9556222B2 (en) * 2012-06-15 2017-01-31 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof

Also Published As

Publication number Publication date
MX2015003078A (es) 2015-07-14
EA201590539A1 (ru) 2015-08-31
EP2892911B1 (en) 2017-08-30
IL237638A0 (en) 2015-04-30
IN2015DN01547A (enExample) 2015-07-03
US20140088163A1 (en) 2014-03-27
DK2892911T3 (en) 2017-10-23
NZ705213A (en) 2018-07-27
AU2013312102A1 (en) 2015-03-12
KR20150053982A (ko) 2015-05-19
CA2882417A1 (en) 2014-03-13
BR112015005200A2 (enExample) 2017-08-15
IL237638B (en) 2020-04-30
HRP20171565T1 (hr) 2017-12-15
KR102237364B1 (ko) 2021-04-06
PT2892911T (pt) 2017-11-02
HK1211295A1 (en) 2016-05-20
CN104768965A (zh) 2015-07-08
SG11201501800UA (en) 2015-04-29
AU2013312102B2 (en) 2018-03-08
ME02911B (me) 2018-10-20
CN104768965B (zh) 2018-05-11
MX366954B (es) 2019-07-31
CY1119762T1 (el) 2018-06-27
JP2015529227A (ja) 2015-10-05
ES2644615T3 (es) 2017-11-29
RS56563B1 (sr) 2018-02-28
BR112015005200B1 (pt) 2022-07-05
HUE036797T2 (hu) 2018-07-30
WO2014040056A1 (en) 2014-03-13
LT2892911T (lt) 2017-11-10
SMT201700501T1 (it) 2017-11-15
PL2892911T3 (pl) 2018-03-30
EA029069B1 (ru) 2018-02-28
JP6272870B2 (ja) 2018-01-31
SI2892911T1 (sl) 2017-12-29
EP2892911A1 (en) 2015-07-15
ZA201501203B (en) 2021-08-25

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