KR102000301B1 - 산화방지성 염증 조절제로서의 피라졸릴 및 피리미디닐 트리사이클릭 엔온 - Google Patents

산화방지성 염증 조절제로서의 피라졸릴 및 피리미디닐 트리사이클릭 엔온 Download PDF

Info

Publication number
KR102000301B1
KR102000301B1 KR1020137018672A KR20137018672A KR102000301B1 KR 102000301 B1 KR102000301 B1 KR 102000301B1 KR 1020137018672 A KR1020137018672 A KR 1020137018672A KR 20137018672 A KR20137018672 A KR 20137018672A KR 102000301 B1 KR102000301 B1 KR 102000301B1
Authority
KR
South Korea
Prior art keywords
delete delete
compound
amino
aralkyl
heteroaryl
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
KR1020137018672A
Other languages
English (en)
Korean (ko)
Other versions
KR20130130784A (ko
Inventor
에릭 앤더슨
게리 엘. 볼턴
브래들리 카프래드
신 지앙
치테즈 리
윌리엄 에이치. 로아크
멜리언 비스닉
Original Assignee
리아타 파마슈티컬즈, 아이엔씨.
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 리아타 파마슈티컬즈, 아이엔씨. filed Critical 리아타 파마슈티컬즈, 아이엔씨.
Publication of KR20130130784A publication Critical patent/KR20130130784A/ko
Application granted granted Critical
Publication of KR102000301B1 publication Critical patent/KR102000301B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Biochemistry (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Toxicology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
KR1020137018672A 2010-12-17 2011-12-19 산화방지성 염증 조절제로서의 피라졸릴 및 피리미디닐 트리사이클릭 엔온 Active KR102000301B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201061424601P 2010-12-17 2010-12-17
US61/424,601 2010-12-17
PCT/US2011/065897 WO2012083306A2 (en) 2010-12-17 2011-12-19 Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators

Publications (2)

Publication Number Publication Date
KR20130130784A KR20130130784A (ko) 2013-12-02
KR102000301B1 true KR102000301B1 (ko) 2019-07-15

Family

ID=45470714

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020137018672A Active KR102000301B1 (ko) 2010-12-17 2011-12-19 산화방지성 염증 조절제로서의 피라졸릴 및 피리미디닐 트리사이클릭 엔온

Country Status (32)

Country Link
US (6) US8513436B2 (enExample)
EP (1) EP2651902B1 (enExample)
JP (1) JP5857068B2 (enExample)
KR (1) KR102000301B1 (enExample)
CN (1) CN103596929B (enExample)
AR (1) AR084353A1 (enExample)
AU (1) AU2011343466B2 (enExample)
BR (1) BR112013015241B1 (enExample)
CA (1) CA2822071C (enExample)
CL (1) CL2013001754A1 (enExample)
CO (1) CO6910185A2 (enExample)
CY (1) CY1120032T1 (enExample)
DK (1) DK2651902T3 (enExample)
EA (1) EA025568B1 (enExample)
ES (1) ES2653717T3 (enExample)
HR (1) HRP20171859T1 (enExample)
HU (1) HUE038046T2 (enExample)
IL (1) IL226923A (enExample)
LT (1) LT2651902T (enExample)
ME (1) ME02973B (enExample)
MX (1) MX2013006902A (enExample)
NO (1) NO2651902T3 (enExample)
NZ (1) NZ612788A (enExample)
PL (1) PL2651902T3 (enExample)
PT (1) PT2651902T (enExample)
RS (1) RS56795B1 (enExample)
SG (1) SG191181A1 (enExample)
SI (1) SI2651902T1 (enExample)
SM (1) SMT201800069T1 (enExample)
TW (1) TWI527788B (enExample)
WO (1) WO2012083306A2 (enExample)
ZA (1) ZA201305060B (enExample)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ME03529B (me) 2008-01-11 2020-04-20 Reata Pharmaceuticals Inc Sintetički triterpenoidi i metode njihove upotrebe u tretmanu bolesti
TW201006474A (en) 2008-04-18 2010-02-16 Reata Pharmaceuticals Inc Natural products including an anti-flammatory pharmacore and methods of use
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
PL2651918T3 (pl) 2010-12-17 2017-12-29 Novartis Ag Krystaliczne formy 5-chloro-N2-(2-izopropoksy-5-metylo-4-piperydyn-4-ylofenylo)-N4-[2-(propano-2-sulfonylo)-fenylo]-pirymidyno-2,4-diaminy
ES2653717T3 (es) 2010-12-17 2018-02-08 Reata Pharmaceuticals, Inc. Pirazolil- y pirimidinil-enonas tricíclicas como moduladores antioxidantes de la inflamación
EP2841445B1 (en) 2012-04-27 2017-06-14 Reata Pharmaceuticals, Inc. 2.2-difluoropropionamide derivatives of bardoxolone methyl, polymorphic forms and methods of use thereof
US9556222B2 (en) 2012-06-15 2017-01-31 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
TWI630212B (zh) 2012-09-10 2018-07-21 瑞塔醫藥有限責任公司 丁香油素(oleanolic acid)之c17-烷二基與烯二基衍生物及其使用方法
US9278912B2 (en) 2012-09-10 2016-03-08 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
TWI649330B (zh) 2013-04-24 2019-02-01 艾伯維有限公司 甲基巴多索龍之2,2-二氟丙醯胺衍生物、其多晶形及其使用方法
WO2015112792A1 (en) * 2014-01-24 2015-07-30 Abbvie Inc. Aryl and arylalkyl substituted pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators
AU2016219109B2 (en) * 2015-02-12 2020-05-14 Reata Pharmaceuticals, Inc. Imidazolyl tricyclic enones as antioxidant iflammation modulators
BR112019009256A2 (pt) 2016-11-08 2019-07-16 Reata Pharmaceuticals, Inc. métodos para tratar síndrome de alport usando bardoxolona metil ou análogos do mesmo
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
US11286226B2 (en) 2017-09-21 2022-03-29 Northwestern University Polycyclic carbogenic molecules and uses thereof as anti-cancer agents
US11465963B2 (en) * 2017-11-21 2022-10-11 Biogen Ma Inc. Tetrahydronaphthalene derivatives useful as Nrf2 activators
US11993574B2 (en) * 2018-06-15 2024-05-28 Reata Pharmaceuticals, Inc Pyrazole and imidazole compounds for inhibition of IL-17 and RORgamma
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
WO2021145655A1 (ko) 2020-01-13 2021-07-22 압타바이오 주식회사 신규한 피라졸 유도체
US20250025465A1 (en) * 2021-11-17 2025-01-23 Northwestern University Wt-idh1 inhibition using a covalent and brain-penetrant small molecular inhibitor for ferroptosis induction in high-grade glioma
WO2024255851A1 (en) * 2023-06-16 2024-12-19 Nanjing Curegene Technology Co., Ltd. Tumor-specific expression cassette and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009146216A2 (en) 2008-04-18 2009-12-03 Reata Pharmaceuticals. Inc. Antioxidant inflammation modulators: novel derivatives of oleanolic acid

Family Cites Families (83)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2875201A (en) 1957-08-28 1959-02-24 Searle & Co Dehydrotigogenone intermediates
US3071577A (en) * 1959-08-13 1963-01-01 Syntex Corp Pyrimidinyl androstanes
US3994935A (en) 1975-11-24 1976-11-30 E. R. Squibb & Sons, Inc. Steroidal 16β-alkyl[16α,17-b]naphthalenes
NZ191586A (en) 1978-10-10 1981-10-19 Sterling Drug Inc Cyanoketones derived from glycyrrhetinic acid and pharmaceutical compositions
US4395423A (en) 1978-10-10 1983-07-26 Sterling Drug Inc. Polycyclic cyanoketones
CN1013672B (zh) * 1983-10-03 1991-08-28 美国辉瑞有限公司 2-氨基-5-羟基-4-甲基嘧啶衍生物的制备方法
US5064823A (en) 1988-08-24 1991-11-12 Research Triangle Institute Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers
DE4014171A1 (de) 1990-05-03 1991-11-07 Basf Ag Cyanochinolinverbindungen
JPH08208479A (ja) * 1994-04-29 1996-08-13 Takeda Chem Ind Ltd クラビンアルカロイド誘導体を含有する鎮痛剤
AU2267995A (en) 1994-04-29 1995-11-29 Takeda Chemical Industries Ltd. Ergoline derivatives as analgesics
KR100418202B1 (ko) * 1994-09-09 2004-07-05 쇼죠 고야마 분자발현기능의억제방법
US6326507B1 (en) 1998-06-19 2001-12-04 Trustees Of Dartmouth College Therapeutic compounds and methods of use
US6369101B1 (en) 1999-02-26 2002-04-09 Regents Of The University Of Minnesota Therapeutic method to treat herpes virus infection
PT1178952E (pt) 1999-05-14 2007-12-04 Univ California Novos moduladores da interleucina-1 e do factor alfa de necrose tumoral, síntese dos referidos moduladores e métodos de utilização dos referidos moduladores
US6649654B1 (en) 1999-11-23 2003-11-18 The Regents Of The University Of California Methods for identifying and using IKK inhibitors
US6890946B2 (en) 1999-12-23 2005-05-10 Indiana University Research And Technology Corporation Use of parthenolide to inhibit cancer
JP4331913B2 (ja) 2000-02-14 2009-09-16 メルク エンド カムパニー インコーポレーテッド エストロゲンレセプターモデュレーター
JP2001240573A (ja) 2000-03-01 2001-09-04 Meiji Seika Kaisha Ltd トリテルペン誘導体及び肝疾患治療剤
WO2002003996A1 (en) 2000-07-12 2002-01-17 RAJKUMAR, Sujatha Use of dammarane-type tritepenoid saporins
US6689767B2 (en) 2000-09-29 2004-02-10 Regents Of The University Of Minnesota Triterpenes having antibacterial activity
JP2004509972A (ja) 2000-09-29 2004-04-02 リージェンツ オブ ザ ユニバーシティ オブ ミネソタ 酵母に対する殺真菌活性を有するトリテルペン
US6951847B2 (en) 2000-09-29 2005-10-04 Regents Of The University Of Minnesota Methods of treating fungal infections using lupeol
US6878751B1 (en) 2000-10-19 2005-04-12 Imperial College Of Science Technology And Medicine Administration of resveratrol to treat inflammatory respiratory disorders
US7435755B2 (en) 2000-11-28 2008-10-14 The Trustees Of Dartmouth College CDDO-compounds and combination therapies thereof
WO2002047611A2 (en) 2000-11-28 2002-06-20 Board Of Regents, The University Of Texas System Cddo-compounds and combination therapies thereof
AU2002226674B2 (en) * 2000-12-28 2007-03-22 Ono Pharmaceutical Co., Ltd. Tricyclic and heterocyclic derivative compounds and drugs containing these compounds as the active ingredient
CN1636058B (zh) 2001-05-14 2011-06-08 龚大为 新型丙氨酸转氨酶及其应用方法
JP2005502654A (ja) 2001-08-13 2005-01-27 メルク エンド カムパニー インコーポレーテッド 選択的エストロゲン受容体調節剤
EP1444207A2 (en) 2001-09-19 2004-08-11 Pharmacia Corporation Substituted pyrazolyl-compounds for the treatment of inflammation
US6991814B2 (en) 2001-12-13 2006-01-31 Council Of Scientific And Industrial Research Herbal medicaments for the treatment of neurocerebrovascular disorders
DK1465615T3 (da) 2002-01-15 2012-11-12 Dartmouth College Tricykliske bisenonderivater og fremgangsmåder til anvendelse heraf
DE60325329D1 (de) 2002-01-18 2009-01-29 Univ Minnesota Quaternäre terpensalze als biologisch aktive tenside
WO2003081210A2 (en) 2002-03-21 2003-10-02 Sunesis Pharmaceuticals, Inc. Identification of kinase inhibitors
EP1507541A4 (en) 2002-05-13 2009-06-03 Dartmouth College HEMMER AND APPLICATION METHOD THEREFOR
US20050014730A1 (en) 2003-04-02 2005-01-20 Carlson Robert M. Anti-fungal formulation of triterpene and essential oil
NZ545565A (en) 2003-09-02 2009-06-26 Unigen Pharmaceuticals Inc Formulation of a mixture of Free-B-Ring flavonoids and flavans for use in the prevention and treatment of cognitive decline and age-related memory impairments
AU2005282437B2 (en) 2004-09-07 2013-01-10 Pacific Arrow Limited Anti-tumor compounds with angeloyl groups
US20050208151A1 (en) 2003-10-30 2005-09-22 Entelos, Inc. Treatment of rheumatoid arthritis with FLIP antagonists
WO2005046732A2 (en) 2003-11-04 2005-05-26 THE UNITED SATES OF AMERICA as represented by THE SECRETARY OF HEALTH AND HUMAN SERVICES, NIH Methods and compositions for the inhibition of hiv-1 replication
US20060258752A1 (en) 2004-02-12 2006-11-16 Vander Jagt David L Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors
JP2005314381A (ja) 2004-03-30 2005-11-10 Anges Mg Inc 増殖性腎疾患の予防・治療・改善剤
WO2006089406A1 (en) * 2005-02-22 2006-08-31 Gemin X Biotechnologies Inc. Diterpenoid compounds, compositions thereof and their use as anti-cancer or anti-fungal agents
CN101189229A (zh) 2005-03-17 2008-05-28 哈佛大学校长及研究员协会 阿韦艾利酰胺、斯特伐希丁b和其类似物的合成
AU2006265113A1 (en) 2005-07-01 2007-01-11 The Johns Hopkins University Compositions and methods for the treatment or prevention of disorders relating to oxidative stress
DE102005041613A1 (de) 2005-09-01 2007-03-08 Ergonex Pharma Gmbh Pharmazeutische Zusammensetzungen zur Behandlung von Karzinoid-Syndrom
US20070232577A1 (en) 2006-03-23 2007-10-04 Advanced Life Sciences, Inc. Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin
WO2007127791A2 (en) 2006-04-25 2007-11-08 The Administrators Of The Tulane Educational Fund New pharmacological method for treatment of neuropathic pain
WO2008000070A1 (en) 2006-06-27 2008-01-03 Wellington Laboratories Inc. Glycyrrhetinic acid derivatives
WO2008016095A1 (en) 2006-08-02 2008-02-07 Santen Pharmaceutical Co., Ltd. PREVENTIVE OR REMEDY FOR KERATOCONJUNCTIVAL DISORDERS CONTAINING Nrf2 ACTIVATOR AS THE ACTIVE INGREDIENT
JP2008110962A (ja) 2006-08-02 2008-05-15 Santen Pharmaceut Co Ltd Nrf2活性化物質を有効成分として含む角結膜障害の予防または治療剤
US8735411B2 (en) 2006-10-02 2014-05-27 Abbvie Inc. Macrocyclic benzofused pyrimidine derivatives
WO2008063318A2 (en) 2006-10-12 2008-05-29 The Texas A & M University System And Safe Et Al Betulinic acid, derivatives and analogs thereof and uses therefor
WO2008064132A2 (en) 2006-11-17 2008-05-29 Trustees Of Dartmouth College Synthetic triterpenoids and tricyclic-bis-enones for use in stimulating bone and cartilage growth
EP2094651A1 (en) 2006-11-17 2009-09-02 Trustees Of Dartmouth College Synthesis and biological activities of new tricyclic-bis-enones (tbes)
WO2012106190A1 (en) 2011-01-31 2012-08-09 Bristol-Myers Squibb Company C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity
EP2653873B8 (en) 2007-02-08 2022-08-24 Biogen MA Inc. Compositions and uses for treating Multiple Sclerosis
JP2008247898A (ja) 2007-03-08 2008-10-16 Santen Pharmaceut Co Ltd トリテルペノイドを有効成分として含有する酸化ストレスが関連する眼疾患の予防又は治療剤
WO2008136838A1 (en) 2007-05-04 2008-11-13 Trustees Of Dartmouth College Novel amide derivatives of cddo and methods of use thereof
US8088824B2 (en) 2007-08-15 2012-01-03 Reata Pharmaceuticals Inc. Forms of CDDO methyl ester
US20090048205A1 (en) 2007-08-15 2009-02-19 Colin Meyer Combination therapy with synthetic triterpenoids and gemcitabine
US9012439B2 (en) 2007-10-29 2015-04-21 University Of Rochester Use of electrophilic compounds for inducing platelet production or maintaining platelet function
ME03529B (me) 2008-01-11 2020-04-20 Reata Pharmaceuticals Inc Sintetički triterpenoidi i metode njihove upotrebe u tretmanu bolesti
EP2279197B1 (en) 2008-04-18 2014-11-05 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring
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
TW201006474A (en) 2008-04-18 2010-02-16 Reata Pharmaceuticals Inc Natural products including an anti-flammatory pharmacore and methods of use
US8278311B2 (en) 2008-04-28 2012-10-02 Abbott Laboratories Substituted pyrimidine derivatives
ES2449396T3 (es) 2008-07-22 2014-03-19 Trustees Of Dartmouth College Cianoenonas monocíclicas y métodos de uso de las mismas
WO2010053817A1 (en) 2008-11-04 2010-05-14 Trustees Of Dartmouth College Betulinic acid derivatives and methods of use thereof
SG173601A1 (en) 2009-02-13 2011-09-29 Reata Pharmaceuticals Inc Delayed release, oral dosage compositions that contain amorphous cddo-me
TWI481607B (zh) 2009-12-17 2015-04-21 Lundbeck & Co As H 作為pde10a酵素抑制劑的2-芳基咪唑衍生物
AU2011240690C1 (en) 2010-04-12 2014-11-06 Reata Pharmaceuticals Holdings, LLC Method of treating obesity using antioxidant inflammation modulators
CN102079772A (zh) 2010-12-09 2011-06-01 中国药科大学 一类五环三萜-13,28-内酯化合物、其制备方法和用途
KR20140017520A (ko) 2010-12-17 2014-02-11 이 아이 듀폰 디 네모아 앤드 캄파니 살진균제 아조사이클릭 아미드
ES2653717T3 (es) 2010-12-17 2018-02-08 Reata Pharmaceuticals, Inc. Pirazolil- y pirimidinil-enonas tricíclicas como moduladores antioxidantes de la inflamación
EA026847B1 (ru) 2011-03-11 2017-05-31 Рита Фармасьютикалз, Инк. C4-монометилтритерпеноидные производные и способы их применения
EP2841445B1 (en) 2012-04-27 2017-06-14 Reata Pharmaceuticals, Inc. 2.2-difluoropropionamide derivatives of bardoxolone methyl, polymorphic forms and methods of use thereof
US9556222B2 (en) 2012-06-15 2017-01-31 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
US9278912B2 (en) 2012-09-10 2016-03-08 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
TWI630212B (zh) 2012-09-10 2018-07-21 瑞塔醫藥有限責任公司 丁香油素(oleanolic acid)之c17-烷二基與烯二基衍生物及其使用方法
LT2892911T (lt) 2012-09-10 2017-11-10 Reata Pharmaceuticals, Inc. Oleanolinės rūgšties c17 heteroarilo dariniai ir jų panaudojimo būdas
IL285832B2 (en) 2013-08-23 2024-01-01 Reata Pharmaceuticals Inc Methods of treating and preventing endothelial dysfunction using bardoxolone methyl or analogs thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009146216A2 (en) 2008-04-18 2009-12-03 Reata Pharmaceuticals. Inc. Antioxidant inflammation modulators: novel derivatives of oleanolic acid

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Bioorganic & Medicinal Chemistry Letters, 1997, 제7권, 제13호, 페이지 1623-1628
Organic Letters, 2010, 제12권, 제3호, 페이지 508-511

Also Published As

Publication number Publication date
CN103596929A (zh) 2014-02-19
JP2014501250A (ja) 2014-01-20
PT2651902T (pt) 2018-02-01
US20140051739A1 (en) 2014-02-20
MX2013006902A (es) 2013-10-17
US20200207706A1 (en) 2020-07-02
AR084353A1 (es) 2013-05-08
IL226923A (en) 2016-06-30
US8513436B2 (en) 2013-08-20
SG191181A1 (en) 2013-07-31
WO2012083306A2 (en) 2012-06-21
HUE038046T2 (hu) 2018-09-28
EP2651902A2 (en) 2013-10-23
US9884809B2 (en) 2018-02-06
AU2011343466B2 (en) 2017-01-05
DK2651902T3 (en) 2018-01-08
US20120196880A1 (en) 2012-08-02
BR112013015241B1 (pt) 2022-03-29
RS56795B1 (sr) 2018-04-30
US11192852B2 (en) 2021-12-07
AU2011343466A1 (en) 2013-07-25
NZ612788A (en) 2015-10-30
CA2822071A1 (en) 2012-06-21
KR20130130784A (ko) 2013-12-02
PL2651902T3 (pl) 2018-04-30
HK1189595A1 (zh) 2014-06-13
NO2651902T3 (enExample) 2018-04-07
EA025568B1 (ru) 2017-01-30
CY1120032T1 (el) 2018-12-12
CN103596929B (zh) 2016-10-19
ME02973B (me) 2018-07-20
US20160130220A1 (en) 2016-05-12
CA2822071C (en) 2019-07-16
HRP20171859T1 (hr) 2018-01-26
US9174941B2 (en) 2015-11-03
US11814338B2 (en) 2023-11-14
WO2012083306A3 (en) 2012-10-11
US20180265455A1 (en) 2018-09-20
SI2651902T1 (en) 2018-02-28
SMT201800069T1 (it) 2018-03-08
US20220281807A1 (en) 2022-09-08
ZA201305060B (en) 2016-07-27
ES2653717T3 (es) 2018-02-08
EP2651902B1 (en) 2017-11-08
EA201390894A1 (ru) 2013-12-30
JP5857068B2 (ja) 2016-02-10
CO6910185A2 (es) 2014-03-31
CL2013001754A1 (es) 2013-11-29
TWI527788B (zh) 2016-04-01
BR112013015241A2 (pt) 2021-04-20
LT2651902T (lt) 2018-01-10
TW201249785A (en) 2012-12-16

Similar Documents

Publication Publication Date Title
US11814338B2 (en) Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators
KR101956399B1 (ko) C4­모노메틸 트리터페노이드 유도체 및 그의 이용 방법
KR102237359B1 (ko) 올레아놀산의 c17―알칸디일 및 알켄디일 유도체 및 그의 사용 방법
KR102237364B1 (ko) 올레아놀산의 c17―헤테로아릴 유도체 및 그의 사용 방법
US20140088188A1 (en) C13-hydroxy derivatives of oleanolic acid and methods of use thereof
KR102686868B1 (ko) 항산화 염증 조절제로서의 이미다졸릴 트리사이클릭 에논
KR20230147077A (ko) 합성 우르솔산 유도체 및 이의 사용 방법
HK1212355B (en) C17-alkanediyl and alkenediyl derivatives of oleanolic acid and methods of use thereof
HK1189894A (en) C4-monomethyl triterpenoid derivatives and methods of use thereof

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20130716

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20161214

Comment text: Request for Examination of Application

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20180409

Patent event code: PE09021S01D

E90F Notification of reason for final refusal
PE0902 Notice of grounds for rejection

Comment text: Final Notice of Reason for Refusal

Patent event date: 20181023

Patent event code: PE09021S02D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20190418

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20190709

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20190709

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
PR1001 Payment of annual fee

Payment date: 20220630

Start annual number: 4

End annual number: 4

PR1001 Payment of annual fee

Payment date: 20230628

Start annual number: 5

End annual number: 5

PR1001 Payment of annual fee

Payment date: 20240617

Start annual number: 6

End annual number: 6

PR1001 Payment of annual fee

Payment date: 20250630

Start annual number: 7

End annual number: 7