BRPI0911208A2 - moduladores inflamatórios antioxidantes: ácido oleanólico derivados com saturação no c-anel. - Google Patents

moduladores inflamatórios antioxidantes: ácido oleanólico derivados com saturação no c-anel.

Info

Publication number
BRPI0911208A2
BRPI0911208A2 BRPI0911208-1A BRPI0911208A BRPI0911208A2 BR PI0911208 A2 BRPI0911208 A2 BR PI0911208A2 BR PI0911208 A BRPI0911208 A BR PI0911208A BR PI0911208 A2 BRPI0911208 A2 BR PI0911208A2
Authority
BR
Brazil
Prior art keywords
acid derivatives
compounds
oleanolic acid
ring saturation
inflammatory modulators
Prior art date
Application number
BRPI0911208-1A
Other languages
English (en)
Inventor
Anderson Eric
Jiang Xin
Liu Xiaofeng
Visnick Melean
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 BRPI0911208A2 publication Critical patent/BRPI0911208A2/pt
Publication of BRPI0911208B1 publication Critical patent/BRPI0911208B1/pt

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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/14—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
    • A61P25/28—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
    • 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
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • C07D413/08—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 linked by a carbon chain containing alicyclic rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Urology & Nephrology (AREA)
  • Oncology (AREA)
  • Psychology (AREA)
  • Dermatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Communicable Diseases (AREA)
  • Emergency Medicine (AREA)
  • Psychiatry (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

compostos moduladores inflamatórios antioxidantes, composição farmacêutica, bem como seu uso a presente invenção refere-se, entre outros compostos, novos derivados do ácido oleanólico com a fórmula: em que as variáveis são definidas neste documento. também são previstas composições farmacêuticas, kits e artigos manufaturados contendo esses compostos, métodos e intermediários usados para produção dos compostos, e métodos de uso desses compostos e composições.
BRPI0911208-1A 2008-04-18 2009-04-20 Compostos moduladores inflamatórios antioxidantes, seu uso, e composição farmacêutica BRPI0911208B1 (pt)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US4633208P 2008-04-18 2008-04-18
US61/046,332 2008-04-18
US11133308P 2008-11-04 2008-11-04
US61/111,333 2008-11-04
PCT/US2009/041170 WO2009129545A1 (en) 2008-04-18 2009-04-20 Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring

Publications (2)

Publication Number Publication Date
BRPI0911208A2 true BRPI0911208A2 (pt) 2019-03-26
BRPI0911208B1 BRPI0911208B1 (pt) 2021-05-25

Family

ID=41726396

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0911208-1A BRPI0911208B1 (pt) 2008-04-18 2009-04-20 Compostos moduladores inflamatórios antioxidantes, seu uso, e composição farmacêutica

Country Status (15)

Country Link
US (6) US7915402B2 (pt)
EP (1) EP2279197B1 (pt)
JP (1) JP5529850B2 (pt)
KR (1) KR101713140B1 (pt)
CN (1) CN102164941B (pt)
AU (1) AU2009237578C1 (pt)
BR (1) BRPI0911208B1 (pt)
CO (1) CO6311106A2 (pt)
EA (1) EA022588B1 (pt)
IL (1) IL208714A (pt)
MX (1) MX2010011437A (pt)
NZ (1) NZ588709A (pt)
TW (1) TWI442925B (pt)
WO (1) WO2009129545A1 (pt)
ZA (1) ZA201007590B (pt)

Families Citing this family (71)

* 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
ZA200706804B (en) 2005-02-03 2008-10-29 Gen Hospital Corp Method for treating gefitinib resistant cancer
KR101354828B1 (ko) 2005-11-04 2014-02-18 와이어쓰 엘엘씨 ｍＴＯＲ 저해자, 헤르셉틴, 및/또는 ＨＫＩ-272의항신생물성 조합
US8022216B2 (en) 2007-10-17 2011-09-20 Wyeth Llc Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
TWI492745B (zh) 2008-01-11 2015-07-21 Reata Pharmaceuticals Inc 合成的三萜系化合物及其使用於治療疾病之方法
WO2009129548A1 (en) 2008-04-18 2009-10-22 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: c-17 homologated oleanolic acid derivatives
MX2010011435A (es) 2008-04-18 2011-01-25 Reata Pharmaceuticals Inc Compuestos que incluyen un nucleo farmaceutico antiinflamatorio y sus metodos de uso.
DK2276493T3 (da) 2008-04-18 2019-01-02 Reata Pharmaceuticals Inc Antioxidative inflammationsmodulatorer: oleanolsyrederivater med amino- og andre modifikationer ved c-17
TW201004627A (en) 2008-04-18 2010-02-01 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: novel derivatives of oleanolic acid
EA022588B1 (ru) 2008-04-18 2016-01-29 Ритэ Фамэсутикл, Инк. Антиоксидантные модуляторы воспаления: производные олеанолевой кислоты с насыщением в с-кольце
CA2725598C (en) 2008-06-17 2013-10-08 Wyeth Llc Antineoplastic combinations containing hki-272 and vinorelbine
AU2009274037B2 (en) 2008-07-22 2015-07-09 Trustees Of Dartmouth College Monocyclic cyanoenones and methods of use thereof
MX2011001318A (es) 2008-08-04 2011-03-04 Wyeth Llc Combinaciones antineoplasicas de 4-anilino-3-cianoquinolinas y capecitabina.
EP2416774B1 (en) 2009-04-06 2015-11-04 Wyeth LLC Treatment regimen utilizing neratinib for breast cancer
KR101837759B1 (ko) 2010-02-18 2018-04-26 브이티브이 테라퓨틱스 엘엘씨 치환된 융합 이미다졸 유도체, 약학적 조성물, 및 그것의 사용 방법
US8759535B2 (en) 2010-02-18 2014-06-24 High Point Pharmaceuticals, Llc Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
ME03713B (me) 2010-04-12 2021-01-20 Reata Pharmaceuticals Inc Bardoksolon meтil za lečenje gojaznosтi
WO2012057343A1 (ja) * 2010-10-28 2012-05-03 国立大学法人九州大学 Ｎａｄ（ｐ）ｈオキシダーゼ阻害剤、酸化ストレス疾患治療薬、酸化ストレス疾患治療方法及びスクリーニング方法
NZ612788A (en) 2010-12-17 2015-10-30 Reata Pharmaceuticals Inc Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators
EP2683731B1 (en) * 2011-03-11 2019-04-24 Reata Pharmaceuticals, Inc. C4-monomethyl triterpenoid derivatives and methods of use thereof
WO2012162260A2 (en) 2011-05-21 2012-11-29 Kdt, Llc. Transgenic biosensors
CN102499925B (zh) * 2011-10-21 2015-11-11 上海中医药大学 一种中性粒细胞弹性蛋白酶抑制剂
JP6211527B2 (ja) * 2011-12-01 2017-10-11 ハンジョウ ベンシェン ファーマシューティカル シーオー．， エルティーディー．Ｈａｎｇｚｈｏｕ Ｂｅｎｓｈｅｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． ２−置換オレアノール酸誘導体、その調製方法及びその用途
CN103945852B (zh) * 2011-12-01 2016-10-19 杭州本生药业有限公司 2-位取代的齐墩果酸衍生物、及其制备方法和应用
WO2013101719A2 (en) * 2011-12-27 2013-07-04 Northeast Ohio Medical University Amooranin compounds and analogs thereof and related methods of use
CN102532246B (zh) * 2012-02-27 2014-06-18 浙江大学 一种齐墩果酸衍生物及其制备方法和应用
CN102631351A (zh) * 2012-03-27 2012-08-15 上海中医药大学附属曙光医院 齐墩果酸在制药中的应用
SI3444261T1 (sl) 2012-04-27 2021-04-30 Reata Pharmaceuticals, Inc. 2,2-difluoropropionamidni derivat bardoksolon metila, njegovi farmacevtski sestavki in polimorfi za uporabo pri zdravljenju določenih stanj
US8921419B2 (en) 2012-05-08 2014-12-30 Trustees Of Dartmouth College Triterpenoids and compositions containing the same
WO2013169740A2 (en) * 2012-05-08 2013-11-14 Trustees Of Dartmouth College Synthetic triterpenoids and methods for modulating stem/progenitor cell gene expression
US8981144B2 (en) 2012-05-08 2015-03-17 Trustees Of Dartmouth College Method for synthesizing 2-cyano-3,12-dioxoolean-1, 9(11)-dien-28-oic acid methyl ester and derivatives thereof
WO2013188818A1 (en) 2012-06-15 2013-12-19 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
PL2892912T3 (pl) 2012-09-10 2019-10-31 Reata Pharmaceuticals Inc C17-alkanodiylowe i alkenodiylowe pochodne kwasu oleanolowego i sposoby ich zastosowania
US9278912B2 (en) 2012-09-10 2016-03-08 Reata Pharmaceuticals, Inc. C13-hydroxy derivatives of oleanolic acid and methods of use thereof
CA2882417C (en) * 2012-09-10 2021-04-20 Reata Pharmaceuticals, Inc. C17-heteroaryl 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
EP2892910B1 (en) * 2012-09-10 2016-09-07 AbbVie Inc. Glycyrrhetinic acid derivatives with anti-inflammatory activity
UY35534A (es) 2013-04-24 2014-10-31 Abbvie Inc Derivados de 2,2-difluoropropanamida y metil bardoxolona, formas polimórficas y métodos de uso
PH12016500358B1 (en) 2013-08-23 2023-08-16 Reata Pharmaceuticals Inc Methods of treating and preventing endothelial dysfunction using bardoxolone methyl or analogs thereof
CN103897011A (zh) * 2014-04-10 2014-07-02 中国药科大学 一类cddo咪唑衍生物、其制备方法和用途
WO2016022543A1 (en) * 2014-08-07 2016-02-11 Northeast Ohio Medical University Lipoprotein lipase activator for mitigation of atherosclerosis and methods of using same
US10189791B2 (en) 2014-08-26 2019-01-29 Trustees Of Dartmouth College Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole
US9896475B2 (en) 2014-08-26 2018-02-20 Trustees Of Dartmouth College Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole
WO2016070063A1 (en) 2014-10-31 2016-05-06 The Regents Of The University Of California Compositions and methods for treating hiv-associated cognitive dysfunction
WO2016089648A1 (en) 2014-12-01 2016-06-09 Vtv Therapeutics Llc Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof
NZ734292A (en) 2015-02-12 2022-09-30 Reata Pharmaceuticals Inc Imidazolyl tricyclic enones as antioxidant inflammation modulators
MX386256B (es) 2015-09-23 2025-03-18 Reata Pharmaceuticals Inc Derivados de acido oleanolico modificado en c4 para la inhibicion de il-17 y otros usos.
WO2019055119A1 (en) 2017-09-14 2019-03-21 Phoenix Biotechnology, Inc. METHOD AND COMPOSITION FOR TREATING VIRAL INFECTION
MX2019005401A (es) 2016-11-08 2019-08-05 Reata Pharmaceuticals Inc Metodos para tratar el sindrome de alport con bardoxolona metilo o analogos de la misma.
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
MX2020002884A (es) 2017-09-14 2020-10-05 Phoenix Biotechnology Inc Método y composición neuroprotectora mejorada para tratar afecciones neurológicas.
US9969768B1 (en) 2017-11-16 2018-05-15 King Saud University Oleanolic acid methyl ester derivatives
EP3746393A4 (en) 2018-02-02 2021-11-03 Galen Therapeutics Llc DEVICE AND METHOD FOR PROTECTING NEURONS AND REDUCING INFLAMMATION AND SCARING
US10137138B1 (en) 2018-05-29 2018-11-27 King Saud University Sulfonylurea derivatives of oleanolic acid
IL279348B2 (en) 2018-06-15 2026-01-01 Reata Pharmaceuticals Inc Decahydro-2h-naphth[1,2-d]imidazole compounds for inhibition of IL-17 and ROR-gamma
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
CN109678922B (zh) * 2018-11-12 2020-07-14 广州市香雪制药股份有限公司 降三萜类化合物及其制备方法、应用
CN111631187B (zh) * 2019-03-01 2022-04-22 广西中医药大学 快速诱导肝纤维化动物模型的方法
WO2021016191A1 (en) 2019-07-19 2021-01-28 Reata Pharmaceuticals, Inc. C17 polar-substituted heteroaromatic synthetic triterpenoids and methods of use thereof
RU2708400C1 (ru) * 2019-08-07 2019-12-06 Федеральное государственное бюджетное учреждение науки Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) (17S)-N-БЕНЗИЛ-5-((3β-АЦЕТОКСИ-28-НОР-УРС-12-ЕН)-17-ИЛ)-1,3,4-ОКСАДИАЗОЛ-2-АМИН, ОБЛАДАЮЩИЙ СЕЛЕКТИВНОЙ ЦИТОТОКСИЧНОСТЬЮ В ОТНОШЕНИИ КЛЕТОК РАКА МОЛОЧНОЙ ЖЕЛЕЗЫ MCF-7
IL293876B1 (en) * 2019-12-19 2025-11-01 Reata Pharmaceuticals Inc Synthetic triterpenoids with nitrogen-based substituents at c-17 and methods of use thereof
CN111205346B (zh) * 2020-02-10 2022-01-28 中国药科大学 齐墩果酸的衍生物及其医药用途
RU2020130238A (ru) 2020-03-31 2022-03-14 Феникс Байотекнолоджи, Инк. Способ и композиции для лечения коронавирусной инфекции
EP4009981B1 (en) 2020-03-31 2023-08-16 Phoenix Biotechnology, Inc. Method and compositions for treating coronavirus infection
CN115803059A (zh) 2020-05-09 2023-03-14 里亚塔医药控股有限责任公司 使用甲基巴多索隆或其类似物治疗covid-19的方法
CN111777657B (zh) * 2020-07-21 2021-08-10 丽水市中医院 一种皂苷化合物及其制备方法与应用
CN114617890A (zh) * 2020-12-08 2022-06-14 四川夏派森医药科技有限公司 DH404在治疗SARS-CoV-2感染中的应用
EP4259155A1 (en) 2020-12-11 2023-10-18 Reata Pharmaceuticals Holdings, LLC Synthetic triterpenoids for use in therapy
US20240140986A1 (en) 2021-01-18 2024-05-02 Reata Pharmaceuticals, Inc. Synthetic ursolic acid derivatives and methods of use thereof
WO2025029691A1 (en) 2023-07-28 2025-02-06 Reata Pharmaceuticals Holdings, LLC Methods for producing triterpenoid derivatives
CN119868373B (zh) * 2025-03-27 2025-06-13 四川省医学科学院·四川省人民医院 一种小分子化合物在缺血性心脏病中的应用

Family Cites Families (88)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5555153Y2 (pt) 1975-03-19 1980-12-20
US4395423A (en) 1978-10-10 1983-07-26 Sterling Drug Inc. Polycyclic cyanoketones
NZ191586A (en) 1978-10-10 1981-10-19 Sterling Drug Inc Cyanoketones derived from glycyrrhetinic acid and pharmaceutical compositions
US4526988A (en) 1983-03-10 1985-07-02 Eli Lilly And Company Difluoro antivirals and intermediate therefor
CA1264738A (en) 1984-12-04 1990-01-23 Eli Lilly And Company Treatment of tumors in mammals
US5013649A (en) 1986-07-01 1991-05-07 Genetics Institute, Inc. DNA sequences encoding osteoinductive products
PT86377B (pt) 1986-12-24 1990-11-20 Lilly Co Eli Processo para a preparacao de conjugados de imunoglobulinas com um difluoronucleosideo acilado
ES2075040T3 (es) 1988-02-16 1995-10-01 Lilly Co Eli 2',3'-dideoxi-2',2'-difluoronucleosidos.
US5064823A (en) 1988-08-24 1991-11-12 Research Triangle Institute Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers
CA2004695C (en) 1988-12-12 1999-08-10 Rosanne Bonjouklian Phospholipid nucleosides
JPH05505815A (ja) 1990-04-04 1993-08-26 ニユコメド・イメージング・アクシエセルカペト ヌクレオシド誘導体
DK0526642T3 (da) 1991-01-29 1998-10-19 Shionogi & Co Triterpenderivat
SE502569C2 (sv) 1991-05-31 1995-11-13 British Tech Group Användning av en immunologiskt inert matris av en sterol och saponiner som kan bilda sfäriska nanopartiklar med snäv storleksfördelning som läkemedelsbärare, partiklar, komposition samt kit
YU43193A (sh) 1992-06-22 1997-01-08 Eli Lilly And Company 2'-deoksi-2',2'-difluoro(4-supstituisani)pirimidinski nukleozidi antivirusnog i antikancerogenog dejstva i međuproizvodi
UA41261C2 (uk) 1992-06-22 2001-09-17 Елі Ліллі Енд Компані Спосіб одержання збагачених бета-аномером нуклеозидів
US5426183A (en) 1992-06-22 1995-06-20 Eli Lilly And Company Catalytic stereoselective glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
US5401838A (en) 1992-06-22 1995-03-28 Eli Lilly And Company Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
US5606048A (en) 1992-06-22 1997-02-25 Eli Lilly And Company Stereoselective glycosylation process for preparing 2'-Deoxy-2', 2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
DE4308042C2 (de) 1993-03-13 2000-10-12 Alstom Energy Syst Gmbh Wälzmühle
US6025395A (en) 1994-04-15 2000-02-15 Duke University Method of preventing or delaying the onset and progression of Alzheimer's disease and related disorders
US5972703A (en) 1994-08-12 1999-10-26 The Regents Of The University Of Michigan Bone precursor cells: compositions and methods
US5521294A (en) 1995-01-18 1996-05-28 Eli Lilly And Company 2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process for the preparation of beta nucleosides
AU3498397A (en) 1996-07-03 1998-01-21 Pharmacia & Upjohn Company Targeted drug delivery using sulfonamide derivatives
NZ336676A (en) 1997-01-24 2000-01-28 Norsk Hydro As Gemcitabine esters or amides useful as anti-cancer and anti-viral agents
US20050276836A1 (en) 1997-06-11 2005-12-15 Michelle Wilson Coated vaginal devices for vaginal delivery of therapeutically effective and/or health-promoting agents
US5965119A (en) 1997-12-30 1999-10-12 Enzon, Inc. Trialkyl-lock-facilitated polymeric prodrugs of amino-containing bioactive agents
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
US6485756B1 (en) 1999-04-06 2002-11-26 Collaborative Technologies, Inc. Stable, homogeneous natural product extracts containing polar and apolar fractions
EP1591437B1 (en) 1999-05-14 2009-11-25 Nereus Pharmaceuticals, Inc. Interleukin-1 and tumor necrosis factor-alpha modulators, syntheses of said modulators and methods of using said modulators
ATE384952T1 (de) 1999-06-25 2008-02-15 Roche Diagnostics Operations Enzymhemmungsimmunverfahren
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
CN1331319A (zh) 2000-06-30 2002-01-16 上海博德基因开发有限公司 一种新的多肽——sr蛋白特异性丝氨酸激酶212.98和编码这种多肽的多核苷酸
WO2002003996A1 (en) 2000-07-12 2002-01-17 RAJKUMAR, Sujatha Use of dammarane-type tritepenoid saporins
EP1322661A1 (en) 2000-09-29 2003-07-02 Regents Of The University Of Minnesota Triterpenes having fungicidal activity against yeast
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
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
AU2002243246A1 (en) 2000-11-28 2002-06-24 Board Of Regents, The University Of Texas System Cddo-compounds and combination therapies thereof
AU2002308701A1 (en) 2001-05-14 2002-11-25 University Of Maryland, Baltimore Novel alanine transaminase enzyme and methods of use
MXPA04004882A (es) 2001-11-23 2005-04-11 Chugai Pharmaceutical Co Ltd Metodo para la identificacion de enzimas que tienen como objetivo tumores.
DK1465615T3 (da) 2002-01-15 2012-11-12 Dartmouth College Tricykliske bisenonderivater og fremgangsmåder til anvendelse heraf
AU2003205244B2 (en) 2002-01-18 2009-01-08 Regents Of The University Of Minnesota Triterpene quaternary salts as biologically active surfactants
US6974801B2 (en) 2002-05-13 2005-12-13 The Trustees Of Dartmounth College Inhibitors and methods of use thereof
EP1567169A4 (en) 2002-11-04 2009-10-21 Xenoport Inc GEMCITABINE PROMOTERS, THEIR PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
WO2004089357A2 (en) 2003-04-02 2004-10-21 Regents Of The University Of Minnesota Anti-fungal formulation of triterpene and essential oil
WO2006029221A2 (en) 2004-09-07 2006-03-16 Pacific Arrow Limited Anti-tumor compounds with angeloyl groups
WO2005042002A2 (en) 2003-10-30 2005-05-12 Entelos, Inc. Treatment of rhematoid 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
JP2006175836A (ja) 2004-12-24 2006-07-06 Fuji Photo Film Co Ltd 感熱記録材料
JP2006347952A (ja) * 2005-06-16 2006-12-28 Yoshihiro Futamura リパーゼ活性化作用を呈するアントラキノン誘導体、それからなる抗肥満薬、食品製剤及び化粧品
WO2007005879A2 (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
DE102005041616B4 (de) 2005-09-01 2011-03-17 Johannes-Gutenberg-Universität Mainz Melanom-assoziierte MHC Klasse I assoziierte Oligopeptide und für diese kodierende Polynukleotide und deren Verwendungen
EP1960790B1 (en) 2005-12-12 2016-12-28 MosaMedix B.V. Annexin derivatives suitable for pretargeting in therapy and diagnosis
US20070232577A1 (en) 2006-03-23 2007-10-04 Advanced Life Sciences, Inc. Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin
US20070249561A1 (en) 2006-04-25 2007-10-25 Taylor Bradley K Pharmacological method for treatment of neuropathic pain
WO2008000068A1 (en) 2006-06-27 2008-01-03 Wellington Laboratories Inc. Method for preparing 2-iodo triterpenoid compounds
JP2008016095A (ja) 2006-07-04 2008-01-24 Sharp Corp 通信システム、復号再生装置、記録装置、通信プログラム及び記録媒体
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
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
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
CA2670099A1 (en) 2006-11-17 2008-05-29 Trustees Of Dartmouth College Synthesis and biological activities of new tricyclic-bis-enones (tbes)
US8299046B2 (en) 2006-11-17 2012-10-30 Trustees Of Dartmouth College Synthetic triterpenoids and tricyclic-bis-enones for use in stimulating bone and cartilage growth
EP2680006A1 (en) 2007-02-08 2014-01-01 Biogen Idec MA Inc. Treatment for Amyotrophic Lateral Sclerosis
WO2008111497A1 (ja) 2007-03-08 2008-09-18 Santen Pharmaceutical 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
TWI492745B (zh) 2008-01-11 2015-07-21 Reata Pharmaceuticals Inc 合成的三萜系化合物及其使用於治療疾病之方法
EA022588B1 (ru) 2008-04-18 2016-01-29 Ритэ Фамэсутикл, Инк. Антиоксидантные модуляторы воспаления: производные олеанолевой кислоты с насыщением в с-кольце
MX2010011435A (es) 2008-04-18 2011-01-25 Reata Pharmaceuticals Inc Compuestos que incluyen un nucleo farmaceutico antiinflamatorio y sus metodos de uso.
TW201004627A (en) 2008-04-18 2010-02-01 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: novel derivatives of oleanolic acid
WO2009129548A1 (en) 2008-04-18 2009-10-22 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: c-17 homologated oleanolic acid derivatives
DK2276493T3 (da) 2008-04-18 2019-01-02 Reata Pharmaceuticals Inc Antioxidative inflammationsmodulatorer: oleanolsyrederivater med amino- og andre modifikationer ved c-17
AU2009274037B2 (en) 2008-07-22 2015-07-09 Trustees Of Dartmouth College Monocyclic cyanoenones and methods of use thereof
US8778990B2 (en) 2008-11-04 2014-07-15 Trustees Of Dartmouth College Betulinic acid derivatives and methods of use thereof
ES2731601T3 (es) 2009-02-13 2019-11-18 Reata Pharmaceuticals Inc Composiciones de dosificación oral de liberación retardada que contienen CDDO-Me amorfo
ME03713B (me) 2010-04-12 2021-01-20 Reata Pharmaceuticals Inc Bardoksolon meтil za lečenje gojaznosтi
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
CA2826113C (en) 2011-01-31 2018-09-04 Bristol-Myers Squibb Company C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity
EP2683731B1 (en) 2011-03-11 2019-04-24 Reata Pharmaceuticals, Inc. C4-monomethyl triterpenoid derivatives and methods of use thereof

Also Published As

Publication number Publication date
US9090574B2 (en) 2015-07-28
JP5529850B2 (ja) 2014-06-25
BRPI0911208B1 (pt) 2021-05-25
USRE45288E1 (en) 2014-12-09
USRE45325E1 (en) 2015-01-06
US7915402B2 (en) 2011-03-29
EP2279197A1 (en) 2011-02-02
EP2279197B1 (en) 2014-11-05
IL208714A (en) 2017-02-28
TWI442925B (zh) 2014-07-01
WO2009129545A8 (en) 2010-04-22
EA201001488A1 (ru) 2011-06-30
CN102164941A (zh) 2011-08-24
US20140179928A1 (en) 2014-06-26
ZA201007590B (en) 2013-09-25
MX2010011437A (es) 2010-12-20
KR20110010610A (ko) 2011-02-01
AU2009237578C1 (en) 2014-12-04
US8124656B2 (en) 2012-02-28
EA022588B1 (ru) 2016-01-29
JP2011518190A (ja) 2011-06-23
IL208714A0 (en) 2010-12-30
AU2009237578A1 (en) 2009-10-22
CN102164941B (zh) 2015-05-27
NZ588709A (en) 2012-11-30
CO6311106A2 (es) 2011-08-22
AU2009237578B2 (en) 2014-07-10
WO2009129545A1 (en) 2009-10-22
US20120245374A1 (en) 2012-09-27
US20110245233A1 (en) 2011-10-06
KR101713140B1 (ko) 2017-03-08
TW201004629A (en) 2010-02-01
US8440820B2 (en) 2013-05-14
US20100056777A1 (en) 2010-03-04

Similar Documents

Publication Publication Date Title
BRPI0911208A2 (pt) moduladores inflamatórios antioxidantes: ácido oleanólico derivados com saturação no c-anel.
BRPI0911422B8 (pt) compostos moduladores inflamatórios antioxidantes, composição farmacêutica e usos dos mesmos
BR112015005168A2 (pt) Derivados de c17-alcanodiila e alquenodiila de ácido oleanólico e métodos de uso dos mesmos
CO6321282A2 (es) Derivados de piperidinilindol como inhibidores de aldosterona sintasa
EA201391313A1 (ru) C4-монометилтритерпеноидные производные и способы их применения
NZ705213A (en) C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
DOP2011000050A (es) Inhibidores de cmet
ECSP10010129A (es) Inhibidores de quinasas símil polo
UY31830A (es) Activadores de glucoquinasa
CR20110309A (es) Compuestos orgánicos
ECSP11011184A (es) Compuestos orgánicos
UY32611A (es) Compuestos de 1-cianoetilheterociclilcarboxamida sustituidos 750
MX2012004311A (es) Derivados de ciclohexano spiro condensados como inhibidores de lipasa sensible a hormonas (hsl) utiles en el tratamiento de diabetes.
BRPI0911105A2 (pt) compostos contendo um farmacóforo anti-inflamatório, composição farmacêutica, bem como seu uso
PA8842101A1 (es) Heteroarilos sustituidos
UY32158A (es) Derivados heterociclicos y metodos de uso de los mismos
CR20110279A (es) Derivados de piridina y pirimidina como inhibidores de fosfodiesterasa 10
BR112012030473A2 (pt) pesticidas baseados em derivados pirrolidina espiroheterocíclicos
EA201390894A1 (ru) Пиразолильные и пиримидинильные трициклические еноны в качестве антиоксидантных модуляторов воспаления
BR112012029647A2 (pt) novos derivados de pirimidinas
UY31905A (es) Derivados de benzoxazinona, procesos de preparación, composiciones farmacéuticas conteniéndolos y aplicaciones.
UY32077A (es) Inhibidores de quinasa tipo polo
BR112015024113A2 (pt) derivados de uréia e seu uso como inibidores da proteína de ligação de ácido graxo (fabp)
UY33181A (es) Derivados de oxazolopirimidina 2,5-sustituidos.
CL2020002058A1 (es) Piridincarboxamidas novedosas.

Legal Events

Date Code Title Description
B07D Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]

Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS.

B06F Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]
B07E Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette]
B06U Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]
B06A Patent application procedure suspended [chapter 6.1 patent gazette]
B09A Decision: intention to grant [chapter 9.1 patent gazette]
B16A Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]

Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 20/04/2009, OBSERVADAS AS CONDICOES LEGAIS. PATENTE CONCEDIDA CONFORME ADI 5.529/DF

B16D Grant of patent or certificate of addition of invention cancelled

Free format text: ANULADA A PUBLICACAO CODIGO 16.1 NA RPI NO 2629 DE 25/05/2021 POR TER SIDO INDEVIDA.

B09X Republication of the decision to grant [chapter 9.1.3 patent gazette]
B16A Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]

Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 20/04/2009, OBSERVADAS AS CONDICOES LEGAIS. PATENTE CONCEDIDA CONFORME ADI 5.529/DF, QUE DETERMINA A ALTERACAO DO PRAZO DE CONCESSAO.