EA019263B1 - Антиоксидативные модуляторы воспаления: производные олеанолевой кислоты с аминовыми и другими модификациями на с-17 - Google Patents
Антиоксидативные модуляторы воспаления: производные олеанолевой кислоты с аминовыми и другими модификациями на с-17 Download PDFInfo
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- EA019263B1 EA019263B1 EA201001555A EA201001555A EA019263B1 EA 019263 B1 EA019263 B1 EA 019263B1 EA 201001555 A EA201001555 A EA 201001555A EA 201001555 A EA201001555 A EA 201001555A EA 019263 B1 EA019263 B1 EA 019263B1
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
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Families Citing this family (62)
| 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 |
| CA2626326C (en) | 2005-11-04 | 2021-02-16 | Wyeth | Antineoplastic combinations with mtor inhibitor, herceptin, and/or hki-272 |
| 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 |
| ME03529B (me) | 2008-01-11 | 2020-04-20 | Reata Pharmaceuticals Inc | Sintetički triterpenoidi i metode njihove upotrebe u tretmanu bolesti |
| ES2326065B1 (es) * | 2008-03-28 | 2010-07-08 | Consejo Superior De Investigaciones Cientificas (Csic) | Utilizacion de un triterpeno pentaciclico para la preparacion de una composicion farmaceutica destinada al tratamiento de la esclerosis multiple. |
| CN102066398B (zh) | 2008-04-18 | 2014-09-10 | 里亚塔医药公司 | 抗氧化剂炎症调节剂:c-17同系化齐墩果酸衍生物 |
| MX2010011437A (es) | 2008-04-18 | 2010-12-20 | Reata Pharmaceuticals Inc | Moduladores antioxidantes de inflamacion: derivados del acido oleanolico con saturacion en el anillo c. |
| WO2009146216A2 (en) | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
| KR101665042B1 (ko) | 2008-04-18 | 2016-10-11 | 리타 파마슈티컬스 잉크. | 소염성 골격군을 포함하는 화합물 및 사용 방법 |
| JP5529851B2 (ja) | 2008-04-18 | 2014-06-25 | リアタ ファーマシューティカルズ インコーポレイテッド | 抗酸化炎症モジュレーター:c−17においてアミノ改変およびその他の改変を加えたオレアノール酸誘導体 |
| DK2310011T3 (da) | 2008-06-17 | 2013-10-14 | Wyeth Llc | Antineoplastiske kombinationer indeholdende hki-272 og vinorelbin |
| AU2009274037B2 (en) | 2008-07-22 | 2015-07-09 | Trustees Of Dartmouth College | Monocyclic cyanoenones and methods of use thereof |
| CA2730715C (en) | 2008-08-04 | 2013-10-01 | Wyeth Llc | Antineoplastic combinations of 4-anilino-3-cyanoquinolines and capecitabine |
| KR20140036332A (ko) | 2009-04-06 | 2014-03-25 | 와이어쓰 엘엘씨 | 네라티닙을 이용한 유방암의 치료법 |
| ES2768204T3 (es) | 2010-04-12 | 2020-06-22 | Reata Pharmaceuticals Inc | Metil bardoxolona para el tratamiento de la obesidad |
| ME02973B (me) | 2010-12-17 | 2018-07-20 | Reata Pharmaceuticals Inc | Pirazolil i pirimidinil triciklični enoni kao antioksidantni modulatori inflamacije |
| UY33946A (es) | 2011-03-11 | 2012-08-31 | Reata Pharmaceuticals Inc | Derivados de c4-monometil triterpenoides y sus métodos de uso |
| BR112013029672A2 (pt) * | 2011-05-16 | 2017-01-17 | Bayer Ip Gmbh | uso de inibição da catepsina k para o tratamento e/ou profilaxia da hipertensão pulmonar e/ou insuficiência cardíaca |
| US8987502B2 (en) | 2011-12-01 | 2015-03-24 | Hangzhou Bensheng Pharmaceutical Co., Ltd. | Oleanolic acid amidate derivatives, preparation methods and uses thereof |
| LT2841445T (lt) | 2012-04-27 | 2017-09-11 | Reata Pharmaceuticals, Inc. | Bardoksolonmetilo 2,2-difluorpropionamido dariniai, polimorfinės formos ir jų panaudojimo būdai |
| 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 |
| US8921419B2 (en) | 2012-05-08 | 2014-12-30 | Trustees Of Dartmouth College | Triterpenoids and compositions containing the same |
| WO2013188818A1 (en) | 2012-06-15 | 2013-12-19 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| CA2884400A1 (en) * | 2012-09-10 | 2014-03-13 | Abbvie Inc. | Glycyrrhetinic acid derivatives and methods of use thereof |
| WO2014040073A1 (en) | 2012-09-10 | 2014-03-13 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| PT2892912T (pt) | 2012-09-10 | 2019-07-12 | Reata Pharmaceuticals Inc | Derivados c17-alcanodiilo e alcenodiilo de ácido oleanólico e métodos de utilização dos mesmos |
| NZ705213A (en) | 2012-09-10 | 2018-07-27 | 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 |
| US9796752B2 (en) | 2013-03-19 | 2017-10-24 | Daiichi Sankyo Company, Limited | Terpenoid derivatives |
| AR096046A1 (es) | 2013-04-24 | 2015-12-02 | Abbvie Inc | Derivados de 2,2-difluoropropanamida de metil bardoxolona, formas polimórficas y métodos de uso |
| MX380589B (es) | 2013-08-23 | 2025-03-12 | Reata Pharmaceuticals Holdings Llc | Métodos de tratamiento y prevencion de la disfunción endotelial utilizando metil bardoxolona o sus análogos. |
| 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 |
| 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 |
| WO2016033132A1 (en) | 2014-08-26 | 2016-03-03 | Trustees Of Dartmouth College | Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole |
| WO2016039359A1 (ja) | 2014-09-10 | 2016-03-17 | 第一三共株式会社 | 眼疾患治療用及び予防用徐放性医薬組成物 |
| US20170333450A1 (en) * | 2014-10-31 | 2017-11-23 | The Regents Of The University Of California | Compositions and methods for treating hiv-associated cognitive dysfunction |
| JP6748652B2 (ja) | 2015-02-12 | 2020-09-02 | リアタ ファーマシューティカルズ インコーポレイテッド | 抗酸化性炎症調節剤としてのイミダゾリル三環式エノン |
| CA2998681C (en) | 2015-09-23 | 2024-02-06 | Reata Pharmaceuticals, Inc. | C4-modified oleanolic acid derivatives for inhibition of il-17 and other uses |
| US10526657B2 (en) * | 2015-12-10 | 2020-01-07 | Universitat Fur Bodenkultur Wien | Compositions and methods for the diagnosis and treatment of bone fractures and disorders |
| 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 |
| KR102486434B1 (ko) | 2016-11-08 | 2023-01-09 | 리아타 파마슈티컬즈 홀딩스, 엘엘씨 | 바독솔론 메틸 또는 이의 유사체를 사용하는 알포트 증후군의 치료 방법 |
| 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 |
| JP7370966B2 (ja) | 2017-09-14 | 2023-10-30 | フェニックス・バイオテクノロジー・インコーポレイテッド | 神経学的状態を治療するための方法および改善された神経保護組成物 |
| KR20210107904A (ko) | 2017-09-14 | 2021-09-01 | 피닉스 바이오테크놀러지 인코포레이티드. | 바이러스 감염 치료를 위한 조성물 |
| IL322405A (en) | 2018-06-15 | 2025-09-01 | 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 |
| BR112021005919A2 (pt) * | 2018-09-28 | 2021-07-27 | Sichuan Haisco Pharmaceutical Co., Ltd. | composto, composição farmacêutica e método para tratar uma doença em um mamífero |
| JP7695229B2 (ja) | 2019-07-19 | 2025-06-18 | リアタ ファーマシューティカルズ インコーポレイテッド | C17極性置換ヘテロ芳香族合成トリテルペノイドおよびその使用方法 |
| JP7711059B2 (ja) * | 2019-11-27 | 2025-07-22 | ▲魯▼南制▲薬▼集▲団▼股▲フン▼有限公司 | オレアナンシンナムアミド誘導体及びその製造方法と用途 |
| JP2023507402A (ja) * | 2019-12-19 | 2023-02-22 | リアタ ファーマシューティカルズ インコーポレイテッド | C17位に窒素ベースの置換基を有する合成トリテルペノイドおよびその使用方法 |
| KR102464428B1 (ko) | 2020-03-31 | 2022-11-04 | 피닉스 바이오테크놀러지 인코포레이티드. | 코로나바이러스 감염 치료를 위한 방법 및 조성물 |
| EP4009981B1 (en) | 2020-03-31 | 2023-08-16 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| EP4146226A1 (en) | 2020-05-09 | 2023-03-15 | Reata Pharmaceuticals Holdings, LLC | Methods of treating covid-19 using bardoxolone methyl or analogs thereof |
| EP4259155A1 (en) | 2020-12-11 | 2023-10-18 | Reata Pharmaceuticals Holdings, LLC | Synthetic triterpenoids for use in therapy |
| WO2022155614A1 (en) | 2021-01-18 | 2022-07-21 | Reata Pharmaceuticals, Inc. | Synthetic ursolic acid derivatives and methods of use thereof |
| CN113603743B (zh) * | 2021-08-06 | 2022-07-15 | 南通大学 | 一类具有联合治疗作用的cddo/川芎嗪醇杂合物及其制备方法和用途 |
| CN117050134A (zh) * | 2022-05-05 | 2023-11-14 | 中国科学院上海有机化学研究所 | 酰胺化合物的合成及其用途 |
| KR20240118918A (ko) | 2023-01-27 | 2024-08-06 | (주)내츄럴코리아 | 올레아놀산 및 유청 단백질 가수분해산물을 포함하는 항산화 화장료 조성물 |
| WO2025029691A1 (en) | 2023-07-28 | 2025-02-06 | Reata Pharmaceuticals Holdings, LLC | Methods for producing triterpenoid derivatives |
| CN117343122B (zh) * | 2023-09-08 | 2025-09-02 | 安徽医科大学 | 一种治疗炎症免疫性疾病的齐墩果酸酰胺衍生物、其制备方法及其用途 |
Family Cites Families (115)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5555153Y2 (enExample) | 1975-03-19 | 1980-12-20 | ||
| 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 |
| 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 |
| IL89258A0 (en) | 1988-02-16 | 1989-09-10 | Lilly Co Eli | 2',3'-dideoxy-2',2'-difluoro-nucleosides |
| 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 |
| CA2079796A1 (en) | 1990-04-04 | 1991-10-05 | Jo Klaveness | Nucleoside derivatives |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| PT909184E (pt) | 1996-07-03 | 2004-02-27 | Upjohn Co | Libertacao de farmaco para um alvo utilizando derivados de sulfonamida |
| ATE236188T1 (de) | 1997-01-24 | 2003-04-15 | Conpharma As | Gemcitabin-derivate |
| 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 |
| NZ515675A (en) | 1999-05-14 | 2004-06-25 | Nereus Pharmaceuticals Inc | Novel interleukin-1 and tumor necrosis factor-alpha modulators, syntheses of said modulators and methods of using said modulators |
| DE60037864T2 (de) | 1999-06-25 | 2009-01-22 | Roche Diagnostics Gmbh | 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 |
| WO2002003996A1 (en) | 2000-07-12 | 2002-01-17 | RAJKUMAR, Sujatha | Use of dammarane-type tritepenoid saporins |
| AU2001294959A1 (en) | 2000-09-29 | 2002-04-08 | Robert M. Carlson | Triterpenes having antibacterial activity |
| WO2002026761A1 (en) | 2000-09-29 | 2002-04-04 | Regents Of The University Of Minnesota | Triterpenes having fungicidal activity against yeast |
| 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 |
| EP1395255A4 (en) | 2000-11-28 | 2007-09-12 | Univ Texas | CDDO COMPOUNDS AND ASSOCIATED POLYTHERAPIES |
| WO2002092768A2 (en) | 2001-05-14 | 2002-11-21 | University Of Maryland, Baltimore | Novel alanine transaminase enzyme and methods of use |
| YU44404A (sh) | 2001-11-23 | 2006-08-17 | Chugai Seiyaku Kabushiki Kaisha | Postupak za identifikovanje ciljnih enzima tumora |
| AU2003235676A1 (en) | 2002-01-15 | 2003-07-30 | Trustees Of Dartmouth College | Tricyclic-bis-enone derivatives and methods of use thereof |
| JP2005519913A (ja) | 2002-01-18 | 2005-07-07 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | 生物学的に活性な表面活性剤としてのトリテルペン第4アンモニウム塩 |
| WO2004064723A2 (en) | 2002-05-13 | 2004-08-05 | Trustees Of Dartmouth College | Inhibitors and methods of use thereof |
| US7265096B2 (en) | 2002-11-04 | 2007-09-04 | Xenoport, Inc. | Gemcitabine prodrugs, pharmaceutical compositions and uses thereof |
| US20050014730A1 (en) | 2003-04-02 | 2005-01-20 | Carlson Robert M. | 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 |
| US8288439B2 (en) | 2003-11-04 | 2012-10-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods and compositions for the inhibition of HIV-1 replication |
| CN1897972A (zh) | 2003-12-22 | 2007-01-17 | 爱尔康公司 | 用于治疗青光眼性视网膜病和视神经病的活性剂 |
| 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 |
| CN1272340C (zh) * | 2004-07-14 | 2006-08-30 | 中国药科大学 | 齐墩果酸偶联衍生物及其药物用途 |
| CN101235071B (zh) * | 2004-12-29 | 2013-02-06 | 浙江大学 | 一类双烯齐墩果酸五环三萜类衍生物及用途 |
| 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 |
| EP1959969A2 (en) | 2005-07-01 | 2008-08-27 | 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 |
| AU2006325586B2 (en) | 2005-12-12 | 2013-01-31 | Mosamedix B.V. | Annexin derivatives suitable for pretargeting in therapy and diagnosis |
| JP2009530405A (ja) | 2006-03-23 | 2009-08-27 | アドバンスト ライフ サイエンシズ インコーポレイテッド | 合成五環性トリテルペノイド、ならびにベツリン酸およびベツリンの誘導体 |
| 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 |
| 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 |
| 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 |
| 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 |
| EP2680009A1 (en) | 2007-02-08 | 2014-01-01 | Biogen Idec MA Inc. | Nrf2 screening assays and related methods and compositions |
| 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 |
| US20080254055A1 (en) | 2007-04-11 | 2008-10-16 | John Erich Oblong | Compositions for Regulation of Hair Growth |
| WO2008136838A1 (en) * | 2007-05-04 | 2008-11-13 | Trustees Of Dartmouth College | Novel amide derivatives of cddo and methods of use thereof |
| WO2009023845A2 (en) | 2007-08-15 | 2009-02-19 | The Board Of Regents Of The University Of Texas System | Combination therapy with synthetic triterpenoids and gemcitabine |
| US8088824B2 (en) * | 2007-08-15 | 2012-01-03 | Reata Pharmaceuticals Inc. | Forms of CDDO methyl ester |
| WO2009058849A1 (en) | 2007-10-29 | 2009-05-07 | 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 |
| JP5529851B2 (ja) | 2008-04-18 | 2014-06-25 | リアタ ファーマシューティカルズ インコーポレイテッド | 抗酸化炎症モジュレーター:c−17においてアミノ改変およびその他の改変を加えたオレアノール酸誘導体 |
| KR101665042B1 (ko) | 2008-04-18 | 2016-10-11 | 리타 파마슈티컬스 잉크. | 소염성 골격군을 포함하는 화합물 및 사용 방법 |
| MX2010011437A (es) | 2008-04-18 | 2010-12-20 | Reata Pharmaceuticals Inc | Moduladores antioxidantes de inflamacion: derivados del acido oleanolico con saturacion en el anillo c. |
| CN102066398B (zh) * | 2008-04-18 | 2014-09-10 | 里亚塔医药公司 | 抗氧化剂炎症调节剂:c-17同系化齐墩果酸衍生物 |
| WO2009146216A2 (en) | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
| JP2010016572A (ja) * | 2008-07-02 | 2010-01-21 | Fujitsu Ltd | 無線通信装置及びシステム |
| AU2009274037B2 (en) | 2008-07-22 | 2015-07-09 | Trustees Of Dartmouth College | Monocyclic cyanoenones and methods of use thereof |
| WO2010053817A1 (en) | 2008-11-04 | 2010-05-14 | Trustees Of Dartmouth College | Betulinic acid derivatives and methods of use thereof |
| JP5775464B2 (ja) | 2009-02-13 | 2015-09-09 | リアタ ファーマシューティカルズ,インク | 非晶質cddo−meを含有する遅延放出性経口投薬組成物 |
| WO2010127029A1 (en) | 2009-05-01 | 2010-11-04 | Ophthotech Corporation | Methods for treating or preventing ophthalmological diseases |
| ES2768204T3 (es) | 2010-04-12 | 2020-06-22 | Reata Pharmaceuticals Inc | Metil bardoxolona para el tratamiento de la obesidad |
| 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 |
| ME02973B (me) | 2010-12-17 | 2018-07-20 | Reata Pharmaceuticals Inc | Pirazolil i pirimidinil triciklični enoni kao antioksidantni modulatori inflamacije |
| MA34909B1 (fr) | 2011-01-31 | 2014-02-01 | Bristol Myers Squibb Co | Triterpénoïdes modifi2s en c-17 et c-3 presentant une activité inhibitrice de la maturation du vih |
| UY33946A (es) | 2011-03-11 | 2012-08-31 | Reata Pharmaceuticals Inc | Derivados de c4-monometil triterpenoides y sus métodos de uso |
| WO2012154554A1 (en) | 2011-05-06 | 2012-11-15 | Catabasis Pharmaceuticals, Inc. | Fatty acid triterpene derivatives and their uses |
| LT2841445T (lt) | 2012-04-27 | 2017-09-11 | Reata Pharmaceuticals, Inc. | Bardoksolonmetilo 2,2-difluorpropionamido dariniai, polimorfinės formos ir jų panaudojimo būdai |
| WO2013169740A2 (en) | 2012-05-08 | 2013-11-14 | Trustees Of Dartmouth College | Synthetic triterpenoids and methods for modulating stem/progenitor cell gene expression |
| US8921419B2 (en) | 2012-05-08 | 2014-12-30 | Trustees Of Dartmouth College | Triterpenoids and compositions containing the same |
| 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 |
| SI2855435T1 (sl) | 2012-05-29 | 2018-09-28 | Parion Sciences Inc. | Dendrimeru podobni amino amidi, ki imajo delovanje blokatorja natrijevih kanalov za zdravljenje suhih oči in drugih mukoznih bolezni |
| WO2013188818A1 (en) | 2012-06-15 | 2013-12-19 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| WO2014040073A1 (en) | 2012-09-10 | 2014-03-13 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| CA2884400A1 (en) | 2012-09-10 | 2014-03-13 | Abbvie Inc. | Glycyrrhetinic acid derivatives and methods of use thereof |
| NZ705213A (en) | 2012-09-10 | 2018-07-27 | Reata Pharmaceuticals Inc | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| PT2892912T (pt) | 2012-09-10 | 2019-07-12 | Reata Pharmaceuticals Inc | Derivados c17-alcanodiilo e alcenodiilo de ácido oleanólico e métodos de utilização dos mesmos |
| WO2014048033A1 (en) | 2012-09-28 | 2014-04-03 | Applied Pharmaceutical Science, Inc. | Polymorphs of cddo ethyl ester and uses thereof |
| CN102887936A (zh) | 2012-10-24 | 2013-01-23 | 苏州晶云药物科技有限公司 | 2-氰基-3,12-二氧代齐墩果-1,9(11)-二烯-28-酸甲酯晶型 |
| CN103788166A (zh) | 2012-10-30 | 2014-05-14 | 中国药科大学 | △13(18)-cddo衍生物、其制备方法与在制药中的用途 |
| AR096046A1 (es) | 2013-04-24 | 2015-12-02 | Abbvie Inc | Derivados de 2,2-difluoropropanamida de metil bardoxolona, formas polimórficas y métodos de uso |
| MX380589B (es) | 2013-08-23 | 2025-03-12 | Reata Pharmaceuticals Holdings Llc | Métodos de tratamiento y prevencion de la disfunción endotelial utilizando metil bardoxolona o sus análogos. |
| EP3097089B1 (en) | 2014-01-24 | 2021-02-24 | Reata Pharmaceuticals, Inc. | Aryl and arylalkyl substituted pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators |
| JP6748652B2 (ja) | 2015-02-12 | 2020-09-02 | リアタ ファーマシューティカルズ インコーポレイテッド | 抗酸化性炎症調節剤としてのイミダゾリル三環式エノン |
| CA2998681C (en) | 2015-09-23 | 2024-02-06 | Reata Pharmaceuticals, Inc. | C4-modified oleanolic acid derivatives for inhibition of il-17 and other uses |
| KR102486434B1 (ko) | 2016-11-08 | 2023-01-09 | 리아타 파마슈티컬즈 홀딩스, 엘엘씨 | 바독솔론 메틸 또는 이의 유사체를 사용하는 알포트 증후군의 치료 방법 |
| 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 |
| JP7695229B2 (ja) | 2019-07-19 | 2025-06-18 | リアタ ファーマシューティカルズ インコーポレイテッド | C17極性置換ヘテロ芳香族合成トリテルペノイドおよびその使用方法 |
| JP2023507402A (ja) | 2019-12-19 | 2023-02-22 | リアタ ファーマシューティカルズ インコーポレイテッド | C17位に窒素ベースの置換基を有する合成トリテルペノイドおよびその使用方法 |
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Non-Patent Citations (2)
| Title |
|---|
| HONDA T. ET AL.: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, 1998, pages 2711-2714, XP002537196, cited in the application, the whole document * |
| SUN H. ET AL.: BOTANICAL STUDIES, vol. 47, 2006, pages 339-368, XP008108435, the whole document * |
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