AU2012229244B2 - C4-monomethyl triterpenoid derivatives and methods of use thereof - Google Patents

C4-monomethyl triterpenoid derivatives and methods of use thereof Download PDF

Info

Publication number
AU2012229244B2
AU2012229244B2 AU2012229244A AU2012229244A AU2012229244B2 AU 2012229244 B2 AU2012229244 B2 AU 2012229244B2 AU 2012229244 A AU2012229244 A AU 2012229244A AU 2012229244 A AU2012229244 A AU 2012229244A AU 2012229244 B2 AU2012229244 B2 AU 2012229244B2
Authority
AU
Australia
Prior art keywords
compound
mmol
alkyl
etoac
alkoxy
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
AU2012229244A
Other languages
English (en)
Other versions
AU2012229244A1 (en
Inventor
Eric Anderson
Christopher F. Bender
Xin Jiang
Xiaofeng Liu
Melean Visnick
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.)
Reata Pharmaceuticals Inc
Original Assignee
Reata Pharmaceuticals 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 Reata Pharmaceuticals Inc filed Critical Reata Pharmaceuticals Inc
Publication of AU2012229244A1 publication Critical patent/AU2012229244A1/en
Application granted granted Critical
Publication of AU2012229244B2 publication Critical patent/AU2012229244B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Psychiatry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Diabetes (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Pulmonology (AREA)
  • Urology & Nephrology (AREA)
  • Transplantation (AREA)
  • Emergency Medicine (AREA)
  • Rheumatology (AREA)
  • Biochemistry (AREA)
  • Cardiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Vascular Medicine (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Dermatology (AREA)
  • Heart & Thoracic Surgery (AREA)
AU2012229244A 2011-03-11 2012-03-09 C4-monomethyl triterpenoid derivatives and methods of use thereof Active AU2012229244B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161452017P 2011-03-11 2011-03-11
US61/452,017 2011-03-11
PCT/US2012/028569 WO2012125488A1 (en) 2011-03-11 2012-03-09 C4-monomethyl triterpenoid derivatives and methods of use thereof

Publications (2)

Publication Number Publication Date
AU2012229244A1 AU2012229244A1 (en) 2013-10-24
AU2012229244B2 true AU2012229244B2 (en) 2017-05-25

Family

ID=45856041

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2012229244A Active AU2012229244B2 (en) 2011-03-11 2012-03-09 C4-monomethyl triterpenoid derivatives and methods of use thereof

Country Status (31)

Country Link
US (1) US9290536B2 (enExample)
EP (1) EP2683731B1 (enExample)
JP (1) JP6129084B2 (enExample)
KR (1) KR101956399B1 (enExample)
CN (1) CN103619866B (enExample)
AR (1) AR085666A1 (enExample)
AU (1) AU2012229244B2 (enExample)
BR (1) BR112013023174B1 (enExample)
CA (1) CA2829618C (enExample)
CL (1) CL2013002612A1 (enExample)
CO (1) CO6801741A2 (enExample)
CY (1) CY1121744T1 (enExample)
DK (1) DK2683731T3 (enExample)
EA (1) EA026847B1 (enExample)
ES (1) ES2729405T3 (enExample)
HR (1) HRP20191164T1 (enExample)
HU (1) HUE044081T2 (enExample)
IL (1) IL228297B (enExample)
LT (1) LT2683731T (enExample)
ME (1) ME03469B (enExample)
MX (1) MX348862B (enExample)
PL (1) PL2683731T3 (enExample)
PT (1) PT2683731T (enExample)
RS (1) RS59200B1 (enExample)
SG (1) SG193404A1 (enExample)
SI (1) SI2683731T1 (enExample)
SM (1) SMT201900433T1 (enExample)
TR (1) TR201909788T4 (enExample)
TW (1) TWI535731B (enExample)
UY (1) UY33946A (enExample)
WO (1) WO2012125488A1 (enExample)

Families Citing this family (36)

* 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
ME03529B (me) 2008-01-11 2020-04-20 Reata Pharmaceuticals Inc Sintetički triterpenoidi i metode njihove upotrebe u tretmanu bolesti
HUE033288T2 (en) 2008-04-18 2017-11-28 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: C-17 homologated oleic acid derivatives
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
TW201006474A (en) 2008-04-18 2010-02-16 Reata Pharmaceuticals Inc Natural products including an anti-flammatory pharmacore and methods of use
EP2279197B1 (en) 2008-04-18 2014-11-05 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring
ES2449396T3 (es) 2008-07-22 2014-03-19 Trustees Of Dartmouth College Cianoenonas monocíclicas y métodos de uso de las mismas
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
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
US9512094B2 (en) * 2012-09-10 2016-12-06 Reata Pharmaceuticals, Inc. C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
MX2015003021A (es) * 2012-09-10 2015-11-09 Abbvie Inc Derivados de acido glicirretinico y metodos de uso de los mismos.
US9278912B2 (en) 2012-09-10 2016-03-08 Reata Pharmaceuticals, Inc. C13-hydroxy derivatives of oleanolic acid and methods of use thereof
LT2892911T (lt) * 2012-09-10 2017-11-10 Reata Pharmaceuticals, Inc. Oleanolinės rūgšties c17 heteroarilo dariniai ir jų panaudojimo būdas
EP2977381B1 (en) 2013-03-19 2018-09-26 Daiichi Sankyo Company, Limited Terpenoid derivative
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
CA2814303A1 (en) 2013-04-26 2014-10-26 Cellphone-Mate, Inc. Apparatus and methods for radio frequency signal boosters
CN104861027A (zh) * 2014-02-24 2015-08-26 上海兰蒂斯生物医药科技有限公司 新型齐墩果酸衍生物、其制备方法及其应用
CN104861028A (zh) * 2014-02-24 2015-08-26 上海兰蒂斯生物医药科技有限公司 新型熊果酸衍生物、其制备方法及其应用
EP3192875B1 (en) 2014-09-10 2019-12-18 Daiichi Sankyo Company, Limited Sustained-release pharmaceutical composition for treating and preventing ophthalmic diseases
AU2016219109B2 (en) 2015-02-12 2020-05-14 Reata Pharmaceuticals, Inc. Imidazolyl tricyclic enones as antioxidant iflammation modulators
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
CN105820207A (zh) * 2016-03-24 2016-08-03 庄立 一种茴拉西坦的药物组合物及其抗氧化作用
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
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
MX2021003643A (es) * 2018-09-28 2021-08-19 Sichuan Haisco Pharmaceutical Co Ltd Derivados de terpenoides y usos de los mismos.
CN120248001A (zh) * 2019-07-19 2025-07-04 里亚塔医药公司 C17极性的-取代的杂芳族合成三萜类化合物及其使用方法
US20240293351A1 (en) 2020-12-11 2024-09-05 Reata Pharmaceuticals Holdings, LLC Methods of administering synthetic triterpenoids
EP4277916A1 (en) 2021-01-18 2023-11-22 Reata Pharmaceuticals, Inc. Synthetic ursolic acid derivatives and methods of use thereof
EP4479369A1 (en) 2022-02-16 2024-12-25 Firmenich SA Process for preparing octahydro-2(1h)-naphthalenone derivatives
GB202211190D0 (en) * 2022-08-01 2022-09-14 Royal College Surgeons Ireland Fluorination process
CN117964678A (zh) * 2024-01-29 2024-05-03 烟台大学 C17位杂芳族羰基修饰的齐墩果烷三萜衍生物及其制备方法和用途

Family Cites Families (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US5064823A (en) 1988-08-24 1991-11-12 Research Triangle Institute Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers
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
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
US6951847B2 (en) 2000-09-29 2005-10-04 Regents Of The University Of Minnesota Methods of treating fungal infections using lupeol
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
US6878751B1 (en) 2000-10-19 2005-04-12 Imperial College Of Science Technology And Medicine Administration of resveratrol to treat inflammatory respiratory disorders
WO2002047611A2 (en) 2000-11-28 2002-06-20 Board Of Regents, The University Of Texas System Cddo-compounds and combination therapies thereof
US7435755B2 (en) 2000-11-28 2008-10-14 The Trustees Of Dartmouth College CDDO-compounds and combination therapies thereof
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
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
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
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
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
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
CN101117348B (zh) 2006-08-01 2010-12-29 浙江海正药业股份有限公司 A环和c环多氧化取代的五环三萜及其制备方法和用途
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
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
US20090048205A1 (en) 2007-08-15 2009-02-19 Colin Meyer Combination therapy with synthetic triterpenoids and gemcitabine
US8088824B2 (en) 2007-08-15 2012-01-03 Reata Pharmaceuticals Inc. Forms of CDDO methyl ester
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
TW201006474A (en) 2008-04-18 2010-02-16 Reata Pharmaceuticals Inc Natural products including an anti-flammatory pharmacore and methods of use
HUE033288T2 (en) 2008-04-18 2017-11-28 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: C-17 homologated oleic acid derivatives
US8071632B2 (en) 2008-04-18 2011-12-06 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: novel derivatives of oleanolic acid
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
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
CN101704874A (zh) * 2009-11-26 2010-05-12 中国药科大学 五环三萜及其衍生物的二甲双胍盐、其制备方法及医药用途
AU2011240690C1 (en) 2010-04-12 2014-11-06 Reata Pharmaceuticals Holdings, LLC Method of treating obesity using antioxidant inflammation modulators
WO2011140078A1 (en) 2010-05-04 2011-11-10 Concert Pharmaceuticals, Inc. Synthetic triterpenoid derivatives
CN102070697A (zh) 2010-12-09 2011-05-25 中国药科大学 一种齐墩果酸衍生物、其制备方法及用途
EA026847B1 (ru) 2011-03-11 2017-05-31 Рита Фармасьютикалз, Инк. C4-монометилтритерпеноидные производные и способы их применения

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
CHEUNG, H.T. et al, Phytochemistry, 1972, vol. 11, pp. 1771-17 *
HONDA, T. et al, Journal of Medicinal Chemistry, 2000, vol. 43, 1866-1877 *
HONDA, T. et al, Journal of Organic Chemistry, 1998, vol. 63, pp. 4846-4849 *
JOHNS, S.R. et al, Australian Journal of Chemistry, 1983, vol. 36, pp. 2537-1547 *
PEAKMAN, T.M. et al, Tetrahedron, 1991, vol. 47, pp. 3779 *
RUZICKA, L. et al, Helvetica Chimica Acta, 1944, vol. 27, pp. 1185-1196 *
WOLFF, G.A. et al, Tetrahedron, 1989, vol. 45, pp. 6721-6728 *

Also Published As

Publication number Publication date
US9290536B2 (en) 2016-03-22
IL228297B (en) 2019-02-28
TR201909788T4 (tr) 2019-07-22
SMT201900433T1 (it) 2019-09-09
CO6801741A2 (es) 2013-11-29
TWI535731B (zh) 2016-06-01
SI2683731T1 (sl) 2019-07-31
PT2683731T (pt) 2019-07-12
RS59200B1 (sr) 2019-10-31
MX348862B (es) 2017-07-03
CL2013002612A1 (es) 2014-05-09
KR101956399B1 (ko) 2019-03-08
CA2829618C (en) 2019-07-09
SG193404A1 (en) 2013-10-30
JP2014508781A (ja) 2014-04-10
EP2683731B1 (en) 2019-04-24
DK2683731T3 (da) 2019-06-11
CN103619866A (zh) 2014-03-05
AU2012229244A1 (en) 2013-10-24
MX2013010429A (es) 2013-10-03
CA2829618A1 (en) 2012-09-20
HRP20191164T1 (hr) 2019-10-04
HUE044081T2 (hu) 2019-09-30
JP6129084B2 (ja) 2017-05-17
UY33946A (es) 2012-08-31
US20120252776A1 (en) 2012-10-04
CN103619866B (zh) 2016-06-22
PL2683731T3 (pl) 2019-09-30
LT2683731T (lt) 2019-07-10
BR112013023174B1 (pt) 2021-09-21
EA026847B1 (ru) 2017-05-31
ES2729405T3 (es) 2019-11-04
WO2012125488A1 (en) 2012-09-20
TW201247696A (en) 2012-12-01
EA201391313A1 (ru) 2014-03-31
KR20140025383A (ko) 2014-03-04
AR085666A1 (es) 2013-10-16
CY1121744T1 (el) 2020-07-31
WO2012125488A8 (en) 2013-10-24
EP2683731A1 (en) 2014-01-15
BR112013023174A2 (pt) 2016-08-09
ME03469B (me) 2020-01-20

Similar Documents

Publication Publication Date Title
EP2683731B1 (en) C4-monomethyl triterpenoid derivatives and methods of use thereof
DK2892911T3 (en) C17 heteroaryl derivatives of oleanolic acid and methods of use thereof
EP2892912B1 (en) C17-alkanediyl and alkenediyl derivatives of oleanolic acid and methods of use thereof
US9278912B2 (en) C13-hydroxy derivatives of oleanolic acid and methods of use thereof
US10898499B2 (en) C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
AU2011343466B2 (en) Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators
US9556222B2 (en) A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
HK1189894A (en) C4-monomethyl triterpenoid derivatives and methods of use thereof

Legal Events

Date Code Title Description
DA3 Amendments made section 104

Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE NAME OF THE INVENTOR TO READ ANDERSON, ERIC; JIANG, XIN; VISNICK, MELEAN; BENDER, CHRISTOPHER F. AND LIU, XIAOFENG

FGA Letters patent sealed or granted (standard patent)