KR20210093886A - 안드로겐 수용체 조절제 및 그 사용 방법 - Google Patents
안드로겐 수용체 조절제 및 그 사용 방법 Download PDFInfo
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- KR20210093886A KR20210093886A KR1020217014230A KR20217014230A KR20210093886A KR 20210093886 A KR20210093886 A KR 20210093886A KR 1020217014230 A KR1020217014230 A KR 1020217014230A KR 20217014230 A KR20217014230 A KR 20217014230A KR 20210093886 A KR20210093886 A KR 20210093886A
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- alkyl
- optionally substituted
- compound
- halogen
- pharmaceutically acceptable
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- WMPQMBUXZHMEFZ-YJPJVVPASA-N turosteride Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(C(C)C)C(=O)NC(C)C)[C@@]2(C)CC1 WMPQMBUXZHMEFZ-YJPJVVPASA-N 0.000 description 1
- 229950007816 turosteride Drugs 0.000 description 1
- 229960000200 ulipristal Drugs 0.000 description 1
- 239000002525 vasculotropin inhibitor Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
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- 229950003684 zibotentan Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Images
Classifications
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6884100B2 (ja) | 2015-01-13 | 2021-06-09 | ブリティッシュ コロンビア キャンサー エージェンシー ブランチ | がんの画像化及び治療用のヘテロ環式化合物ならびにそれらの使用方法 |
| US10471023B2 (en) | 2015-03-12 | 2019-11-12 | British Columbia Cancer Agency Branch | Bisphenol ether derivatives and methods for using the same |
| US20170298033A1 (en) | 2016-04-15 | 2017-10-19 | The University Of British Columbia | Bisphenol derivatives and their use as androgen receptor activity modulators |
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| MX2021004427A (es) | 2018-10-18 | 2021-11-12 | Univ British Columbia | Moduladores del receptor de andrógenos y métodos para su uso. |
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| CN116490165A (zh) | 2020-09-02 | 2023-07-25 | 普洛佩拉治疗公司 | 阿比特龙前药 |
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Family Cites Families (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2571217A (en) | 1951-10-16 | Horace s | ||
| US2890189A (en) | 1954-06-14 | 1959-06-09 | Johnson & Son Inc S C | Alkali soluble resins and compositions containing the same |
| US3074974A (en) | 1957-12-06 | 1963-01-22 | Monsanto Chemicals | Method for the preparation of diglycidyl ether of tetrachlorobisphenol-a |
| US3162615A (en) | 1961-01-03 | 1964-12-22 | Dow Chemical Co | Polyesters from cyclic polyhaloalkane polyols and unsaturated dicarboxylic acids |
| FR1389005A (fr) | 1963-01-09 | 1965-02-12 | Bayer Ag | Procédé perfectionné pour durcir des polyépoxydes |
| SU638596A1 (ru) | 1975-09-01 | 1978-12-25 | Государственный Научно-Исследовательский И Проектный Институт Полимерных Клеев Им. Э.Л.Тер-Газаряна | Хлоргидриднное производное диаллилизоциануровой кислоты в качестве пластификатора поливинилацетатной эмульсии |
| US4284574A (en) | 1979-06-15 | 1981-08-18 | Ciba-Geigy Corporation | Diglycidyl ethers of di-secondary alcohols, their preparation, and curable compositions containing them |
| SU929630A1 (ru) | 1980-02-06 | 1982-05-23 | Научно-Исследовательский Институт Биологии При Иркутском Государственном Университете Им.А.А.Жданова | Способ получени ди-или триоксидифенил-сульфонов |
| US4369298A (en) | 1980-05-27 | 1983-01-18 | Tokuyama Soda Kabushiki Kaisha | Novel cured resin, process for production thereof, and lens composed of said resin from bis(alkyleneoxyphenyl)-diacrylate, bis(alkyleneoxyphenyl)diallyl ether, bis(alkyleneoxyphenyl)diallyl carbonate monomers |
| EP0056175B1 (en) | 1981-01-13 | 1985-05-02 | Teijin Limited | Ion-permeable composite membrane and its use in selective separation |
| IN169231B (https=) | 1984-03-15 | 1991-09-14 | Ciba Geigy Ag | |
| PL141793B1 (en) | 1984-10-08 | 1987-08-31 | Politechnika Warszawska | Method of obtaining bisphenolic resins |
| US5753730A (en) | 1986-12-15 | 1998-05-19 | Mitsui Toatsu Chemicals, Inc. | Plastic lenses having a high-refractive index, process for the preparation thereof and casting polymerization process for preparing sulfur-containing urethane resin lens and lens prepared thereby |
| JPH0832844B2 (ja) | 1987-02-09 | 1996-03-29 | パイロツトインキ株式会社 | 筆記板用不透明性インキ |
| DE3852839T2 (de) | 1987-04-27 | 1995-06-22 | Mitsubishi Gas Chemical Co | Hitzehärtbare Harzzusammensetzung. |
| WO1988009782A1 (en) | 1987-06-01 | 1988-12-15 | The Dow Chemical Company | Process for making propargyl ethers of hydroxyaromatic compounds |
| US5155196A (en) | 1987-06-01 | 1992-10-13 | The Dow Chemical Company | Polymer resulting from the cure of a preformed chromene-containing mixture |
| JP2572020B2 (ja) | 1987-06-19 | 1997-01-16 | 竹本油脂株式会社 | 熱硬化性樹脂用難燃剤 |
| DE3821585A1 (de) | 1987-09-13 | 1989-03-23 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial fuer hochenergetische strahlung |
| US4855184A (en) | 1988-02-02 | 1989-08-08 | Minnesota Mining And Manufacturing Company | Radiation-curable protective coating composition |
| DE3939760A1 (de) | 1989-12-01 | 1991-06-06 | Bayer Ag | Verfahren zur lackierung von kunststoffen, lackierte kunststoffe und die verwendung von hierzu geeigneten haftvermittlern |
| EP0515128A1 (en) | 1991-05-23 | 1992-11-25 | Konica Corporation | Silver halide color photographic light-sensitive material |
| JPH0649473A (ja) | 1992-08-04 | 1994-02-22 | Asahi Chem Ind Co Ltd | 冷媒組成物 |
| DE4323512A1 (de) | 1992-09-01 | 1994-04-28 | Agfa Gevaert Ag | Fotografisches Aufzeichnungsmaterial |
| DE4326393A1 (de) * | 1993-08-06 | 1995-02-09 | Merck Patent Gmbh | Trifluorethoxypyri(mi)din-Derivate und flüssigkristallines Medium |
| JPH07117349A (ja) | 1993-10-27 | 1995-05-09 | Asahi Denka Kogyo Kk | 感熱記録材料 |
| CN1167437A (zh) | 1994-11-29 | 1997-12-10 | 赫彻斯特马里恩鲁斯公司 | 用三芳基-乙烯衍生物治疗和预防骨质疏松的方法 |
| DE19526146A1 (de) | 1995-07-07 | 1997-01-09 | Schering Ag | Triphenylethylene, Verfahren zu deren Herstellung, diese Triphenylethylene enthaltene pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| JPH09176240A (ja) | 1995-12-27 | 1997-07-08 | Mitsubishi Chem Corp | 光重合性組成物 |
| JPH10133427A (ja) | 1996-11-05 | 1998-05-22 | Fuji Xerox Co Ltd | 静電潜像現像用キャリア、静電潜像現像剤及び画像形成方法 |
| ZA98900B (en) | 1997-02-07 | 1998-08-03 | Shell Int Research | Process for the manufacture of epoxy compounds |
| JPH10316803A (ja) | 1997-05-16 | 1998-12-02 | Teijin Chem Ltd | 難燃性樹脂組成物 |
| IL125840A (en) | 1997-08-22 | 2002-12-01 | Teijin Chemicals Ltd | Bromine compound production method |
| JPH11166087A (ja) | 1997-12-04 | 1999-06-22 | Teijin Chem Ltd | 難燃性樹脂組成物 |
| AU4494399A (en) | 1998-06-30 | 2000-01-24 | University Of British Columbia, The | Inhibitors of androgen-independent activation of androgen receptor |
| US6245117B1 (en) | 1998-08-07 | 2001-06-12 | Ipposha Oil Industries Co., Ltd. | Modifier of cellulose fibers and modification method of cellulose fibers |
| US6218430B1 (en) | 1998-08-24 | 2001-04-17 | Ligand Pharmaceuticals Incorporated | Vitamin D3 mimics |
| JP3795679B2 (ja) | 1998-09-01 | 2006-07-12 | 帝人化成株式会社 | 臭素化合物の製造方法 |
| AU775928B2 (en) | 1999-10-14 | 2004-08-19 | Bristol-Myers Squibb Company | Crystallographic structure of the androgen receptor ligand binding domain |
| US6534621B2 (en) | 2000-05-18 | 2003-03-18 | Dow Global Technologies Inc. | Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom |
| US6472436B1 (en) | 2000-07-17 | 2002-10-29 | The Salk Institute For Biological Studies | Methods for protecting cells from amyloid toxicity and for inhibiting amyloid protein production |
| US6756400B2 (en) | 2000-08-31 | 2004-06-29 | Theravance, Inc. | Sodium channel modulators |
| DE10102322A1 (de) * | 2001-01-19 | 2002-07-25 | Merck Patent Gmbh | Phenylderivate |
| US6646102B2 (en) | 2001-07-05 | 2003-11-11 | Dow Global Technologies Inc. | Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom |
| US20030092724A1 (en) | 2001-09-18 | 2003-05-15 | Huaihung Kao | Combination sustained release-immediate release oral dosage forms with an opioid analgesic and a non-opioid analgesic |
| US7344700B2 (en) | 2002-02-28 | 2008-03-18 | University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
| GB0324551D0 (en) | 2003-10-21 | 2003-11-26 | Karobio Ab | Novel compounds |
| US7595345B2 (en) | 2003-11-20 | 2009-09-29 | Eli Lilly And Company | Vitamin D receptor modulators |
| CA2555597C (en) | 2004-02-13 | 2016-06-14 | The University Of British Columbia | Radiolabeled compounds and compositions, their precursors and methods for their production |
| JP2005325301A (ja) | 2004-05-17 | 2005-11-24 | Fuji Photo Film Co Ltd | セルロースアシレートドープ組成物、およびセルロースアシレートフィルム |
| EP1781280A2 (en) | 2004-08-18 | 2007-05-09 | Warner-Lambert Company LLC | Androgen modulators |
| JP2006208607A (ja) | 2005-01-26 | 2006-08-10 | Fuji Photo Film Co Ltd | パターン形成材料、並びにパターン形成装置及び永久パターン形成方法 |
| JP4753601B2 (ja) | 2005-03-23 | 2011-08-24 | 旭化成イーマテリアルズ株式会社 | 感光性組成物 |
| EP1717235A3 (en) | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| FR2885904B1 (fr) | 2005-05-19 | 2007-07-06 | Aventis Pharma Sa | Nouveaux derives du fluorene, compositions les contenant et utilisation |
| EP1792622A1 (en) | 2005-11-11 | 2007-06-06 | GPC Biotech AG | Anti-proliferative combination therapy comprising a platinum-based chemotherapeutic agent and EGFR inhibitors or pyrimidine analogues |
| WO2007079078A1 (en) * | 2005-12-29 | 2007-07-12 | Bayer Schering Pharma Aktiengesellschaft | Diamine derivatives as inhibitors of leukotriene a4 hydrolase |
| JP2007290980A (ja) | 2006-04-21 | 2007-11-08 | Shin Etsu Chem Co Ltd | 含フッ素(メタ)アクリル酸エステル |
| DE102006019044A1 (de) * | 2006-04-25 | 2007-10-31 | Merck Patent Gmbh | Antioxidantien |
| TW200819421A (en) | 2006-10-31 | 2008-05-01 | Univ Nat Chunghsing | The method of synthesizing biphenol A, BPA having di-alkoxyl group by using polycarbonate or its waste |
| US8198311B2 (en) * | 2006-11-01 | 2012-06-12 | Bristol-Myers Squibb Company | Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| KR20090115797A (ko) | 2007-02-20 | 2009-11-06 | 바스프 에스이 | 고굴절률 단량체, 이의 조성물 및 용도 |
| RU2572596C2 (ru) | 2008-07-02 | 2016-01-20 | Бритиш Коламбиа Кэнсер Эйдженси Бранч | Терапевтические средства на основе производных диглицилиловых простых эфиров и способы их применения |
| AU2009279936A1 (en) | 2008-08-05 | 2010-02-11 | Banyu Pharmaceutical Co., Ltd. | Therapeutic compounds |
| AR079975A1 (es) | 2010-01-06 | 2012-03-07 | British Columbia Cancer Agency | Agentes terapeuticos derivados de bisfenol u metodos para su uso, composiciones farmaceuticas y uso de los mismos |
| AR079846A1 (es) | 2010-01-06 | 2012-02-22 | British Columbia Cancer Agency | Agentes terapeuticos derivados de bisfenol que contienen un grupo aquiral y su uso en el tratamiento del cancer |
| EP2693875A4 (en) | 2011-04-08 | 2014-10-22 | British Columbia Cancer Agency | BISPHENOL COMPOUNDS AND METHOD FOR THEIR USE |
| WO2012145328A1 (en) | 2011-04-18 | 2012-10-26 | The University Of British Columbia | Dibenzylphenyl compounds and methods for their use |
| WO2012145330A1 (en) | 2011-04-18 | 2012-10-26 | The University Of British Columbia | Fluorene-9-bisphenol compounds and methods for their use |
| WO2013028572A1 (en) | 2011-08-19 | 2013-02-28 | British Columbia Cancer Agency Branch | Fluorinated bisphenol ether compounds and methods for their use |
| WO2013028791A1 (en) | 2011-08-22 | 2013-02-28 | British Columbia Cancer Agency Branch | 18f compounds for cancer imaging and methods for their use |
| WO2013131018A1 (en) * | 2012-03-02 | 2013-09-06 | Zalicus Pharmaceuticals Ltd. | Biaryl inhibitors of the sodium channel |
| US9365510B2 (en) | 2012-04-16 | 2016-06-14 | British Columbia Cancer Agency Branch | Aziridine bisphenol ethers and related compounds and methods for their use |
| CN105358522A (zh) * | 2013-05-10 | 2016-02-24 | 不列颠哥伦比亚癌症局分支机构 | 雄激素受体调节剂的酯衍生物及其使用方法 |
| CN103342892A (zh) | 2013-06-06 | 2013-10-09 | 西安交通大学 | 一种双马来酰亚胺树脂的增韧改性剂及其制备方法 |
| US20150010469A1 (en) | 2013-07-03 | 2015-01-08 | British Columbia Cancer Agency Branch | Bisphenol ether compounds with novel bridging groups and methods for their use |
| SG11201601431VA (en) | 2013-09-09 | 2016-03-30 | British Columbia Cancer Agency | Halogenated compounds for cancer imaging and treatment and methods for their use |
| WO2015042414A1 (en) * | 2013-09-20 | 2015-03-26 | Karyopharm Therapeutics Inc. | Multicyclic compounds and methods of using same |
| WO2016058080A1 (en) | 2014-10-14 | 2016-04-21 | British Columbia Cancer Agency Branch | Fluoro-chloro bisphenol ether compounds and methods for their use |
| WO2016058082A1 (en) | 2014-10-14 | 2016-04-21 | British Columbia Cancer Agency Branch | 18f compounds for cancer imaging and methods for their use |
| JP6884100B2 (ja) * | 2015-01-13 | 2021-06-09 | ブリティッシュ コロンビア キャンサー エージェンシー ブランチ | がんの画像化及び治療用のヘテロ環式化合物ならびにそれらの使用方法 |
| US10471023B2 (en) | 2015-03-12 | 2019-11-12 | British Columbia Cancer Agency Branch | Bisphenol ether derivatives and methods for using the same |
| CA2929345A1 (en) | 2015-09-02 | 2017-03-02 | British Columbia Cancer Agency Branch | Co-targeting androgen receptor splice variants and mtor signaling pathway for the treatment of castration-resistant prostate cancer |
| US20170298033A1 (en) * | 2016-04-15 | 2017-10-19 | The University Of British Columbia | Bisphenol derivatives and their use as androgen receptor activity modulators |
| WO2017210771A1 (en) | 2016-06-06 | 2017-12-14 | British Columbia Cancer Agency Branch | Compounds and compositions for radiation therapy and methods of using the same |
| WO2018045450A1 (en) * | 2016-09-09 | 2018-03-15 | British Columbia Cancer Agency Branch | Bisphenol a compounds and methods for treating drug-resistant androgen receptor mediated cancers |
| MX2021004427A (es) | 2018-10-18 | 2021-11-12 | Univ British Columbia | Moduladores del receptor de andrógenos y métodos para su uso. |
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| CN113195441B (zh) | 2024-07-12 |
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| EP3867216A1 (en) | 2021-08-25 |
| AU2019362061B2 (en) | 2024-09-26 |
| CN118684633A (zh) | 2024-09-24 |
| IL282257A (en) | 2021-05-31 |
| US11059795B2 (en) | 2021-07-13 |
| BR112021007222A2 (pt) | 2021-08-10 |
| EP3867216A4 (en) | 2022-07-13 |
| SG11202103325WA (en) | 2021-05-28 |
| NZ774611A (en) | 2025-03-28 |
| CL2021000977A1 (es) | 2021-10-22 |
| CO2021006354A2 (es) | 2021-05-31 |
| MX2021004427A (es) | 2021-11-12 |
| JP2022504949A (ja) | 2022-01-13 |
| JP2024123097A (ja) | 2024-09-10 |
| ZA202102202B (en) | 2024-06-26 |
| PH12021550800A1 (en) | 2021-10-04 |
| US20200123117A1 (en) | 2020-04-23 |
| PE20211543A1 (es) | 2021-08-16 |
| AU2019362061A8 (en) | 2021-06-17 |
| CN113195441A (zh) | 2021-07-30 |
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