CA2501867A1 - Heterocyclic selective androgen receptor modulators and methods of use thereof - Google Patents
Heterocyclic selective androgen receptor modulators and methods of use thereof Download PDFInfo
- Publication number
- CA2501867A1 CA2501867A1 CA002501867A CA2501867A CA2501867A1 CA 2501867 A1 CA2501867 A1 CA 2501867A1 CA 002501867 A CA002501867 A CA 002501867A CA 2501867 A CA2501867 A CA 2501867A CA 2501867 A1 CA2501867 A1 CA 2501867A1
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- Prior art keywords
- androgen receptor
- receptor modulator
- selective androgen
- subject
- modulator compound
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- 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.)
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
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Landscapes
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| US41817302P | 2002-10-15 | 2002-10-15 | |
| US60/418,173 | 2002-10-15 | ||
| PCT/US2003/032510 WO2004035737A2 (en) | 2002-10-15 | 2003-10-14 | Heterocyclic selective androgen receptor modulators and methods of use thereof |
Publications (1)
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| CA2501867A1 true CA2501867A1 (en) | 2004-04-29 |
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| CA002501867A Abandoned CA2501867A1 (en) | 2002-10-15 | 2003-10-14 | Heterocyclic selective androgen receptor modulators and methods of use thereof |
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| US (2) | US7214693B2 (enExample) |
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| TW (1) | TW200502249A (enExample) |
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| US20040260108A1 (en) * | 2001-06-25 | 2004-12-23 | Dalton James T. | Metabolites of selective androgen receptor modulators and methods of use thereof |
| US8853266B2 (en) * | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| US20070161608A1 (en) * | 2001-12-06 | 2007-07-12 | Dalton James T | Selective androgen receptor modulators for treating muscle wasting |
| UA87854C2 (en) * | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| US20110237664A1 (en) * | 2004-06-07 | 2011-09-29 | Dalton James T | Selective androgen receptor modulators for treating diabetes |
| US9889110B2 (en) | 2004-06-07 | 2018-02-13 | University Of Tennessee Research Foundation | Selective androgen receptor modulator for treating hormone-related conditions |
| US9884038B2 (en) | 2004-06-07 | 2018-02-06 | University Of Tennessee Research Foundation | Selective androgen receptor modulator and methods of use thereof |
| US8288366B2 (en) | 2006-06-20 | 2012-10-16 | Chochinov Ronald H | Formulation for hair growth |
| US9604931B2 (en) | 2007-01-22 | 2017-03-28 | Gtx, Inc. | Nuclear receptor binding agents |
| US9623021B2 (en) * | 2007-01-22 | 2017-04-18 | Gtx, Inc. | Nuclear receptor binding agents |
| BRPI0806371A2 (pt) * | 2007-01-22 | 2011-09-13 | Gtx Inc | agentes ligação de receptor nuclear |
| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
| ES2413504T3 (es) | 2007-12-21 | 2013-07-16 | Ligand Pharmaceuticals Inc. | Moduladores selectivos del receptor de andrógeno (SARM) y usos de los mismos |
| US8791158B2 (en) * | 2010-01-11 | 2014-07-29 | Gtx, Inc. | Methods of treating meibomian gland dysfunction |
| US8395552B2 (en) | 2010-11-23 | 2013-03-12 | Metamagnetics, Inc. | Antenna module having reduced size, high gain, and increased power efficiency |
| FR2982261B1 (fr) | 2011-11-04 | 2014-06-13 | Galderma Res & Dev | Nouveaux amides, et leur utilisation pharmaceutique ou cosmetique |
| US10987334B2 (en) | 2012-07-13 | 2021-04-27 | University Of Tennessee Research Foundation | Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs) |
| US9969683B2 (en) | 2012-07-13 | 2018-05-15 | Gtx, Inc. | Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS) |
| US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| US9744149B2 (en) | 2012-07-13 | 2017-08-29 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| US9622992B2 (en) | 2012-07-13 | 2017-04-18 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| IN2015DN01046A (enExample) | 2012-07-13 | 2015-06-26 | Gtx Inc | |
| GB201321601D0 (en) * | 2013-12-06 | 2014-01-22 | Canbex Therapeutics Ltd | Modulator |
| EP3613418A1 (en) | 2014-01-17 | 2020-02-26 | Ligand Pharmaceuticals, Inc. | Methods and compositions for modulating hormone levels |
| CN103772238B (zh) * | 2014-01-24 | 2017-03-22 | 苏州伊莱特新药研发有限公司 | 一类新的含酯基芳香丙酰胺化合物及其制备方法和用途 |
| US10654809B2 (en) | 2016-06-10 | 2020-05-19 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10441570B2 (en) | 2015-04-21 | 2019-10-15 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) Ligands and methods of use thereof |
| US10093613B2 (en) | 2015-04-21 | 2018-10-09 | Gtx, Inc. | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10865184B2 (en) | 2015-04-21 | 2020-12-15 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10806720B2 (en) | 2015-04-21 | 2020-10-20 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10314797B2 (en) * | 2016-06-10 | 2019-06-11 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US11230523B2 (en) | 2016-06-10 | 2022-01-25 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US10806719B2 (en) | 2016-06-10 | 2020-10-20 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| US12202815B2 (en) | 2018-09-05 | 2025-01-21 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
| BR112021020864A2 (pt) | 2019-04-19 | 2021-12-14 | Ligand Pharm Inc | Formas cristalinas e métodos de produção de formas cristalinas de um composto |
| WO2025102293A1 (zh) * | 2023-11-16 | 2025-05-22 | 北京脑科学与类脑研究所 | 神经活性雄激素受体调节剂及其用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU88769I2 (fr) * | 1982-07-23 | 1996-11-05 | Zeneca Ltd | Bicalutamide et ses sels et esters pharmaceutiquement acceptables (Casodex (R)) |
| GB8617653D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
| US6174905B1 (en) * | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| WO1998053826A1 (en) * | 1997-05-30 | 1998-12-03 | The University Of Tennessee Research Corporation | Non-steroidal agonist compounds and their use in male hormone therapy |
| DE19723722A1 (de) * | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| AU2001285230C1 (en) * | 2000-08-24 | 2008-03-13 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| EA200401121A1 (ru) * | 2002-02-28 | 2005-10-27 | Юниверсити Оф Теннесси Рисерч Фаундейшн | Необратимые селективные модуляторы андрогенового рецептора и способы их применения |
| CN100537520C (zh) * | 2002-06-17 | 2009-09-09 | 田纳西大学研究基金会 | N-桥连选择性雄激素受体调节剂及其使用方法 |
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- 2003-10-14 CN CNA2003801061407A patent/CN1726193A/zh active Pending
- 2003-10-14 EP EP03777597A patent/EP1562906A4/en not_active Withdrawn
- 2003-10-14 US US10/683,125 patent/US7214693B2/en not_active Expired - Fee Related
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| JP2006518328A (ja) | 2006-08-10 |
| AU2003287076C1 (en) | 2010-03-04 |
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| AU2003287076A1 (en) | 2004-05-04 |
| AU2003287076A2 (en) | 2004-05-04 |
| AU2009202683A1 (en) | 2009-07-23 |
| WO2004035737A3 (en) | 2004-09-10 |
| TW200502249A (en) | 2005-01-16 |
| CN1726193A (zh) | 2006-01-25 |
| WO2004035737A2 (en) | 2004-04-29 |
| US7214693B2 (en) | 2007-05-08 |
| US20040138244A1 (en) | 2004-07-15 |
| AU2003287076B2 (en) | 2009-04-02 |
| EP1562906A4 (en) | 2009-12-02 |
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