MXPA06013329A - Moduladores del receptor androgeno, y metodo para tratar enfermedades en el que se utilizan los mismos. - Google Patents
Moduladores del receptor androgeno, y metodo para tratar enfermedades en el que se utilizan los mismos.Info
- Publication number
- MXPA06013329A MXPA06013329A MXPA06013329A MXPA06013329A MXPA06013329A MX PA06013329 A MXPA06013329 A MX PA06013329A MX PA06013329 A MXPA06013329 A MX PA06013329A MX PA06013329 A MXPA06013329 A MX PA06013329A MX PA06013329 A MXPA06013329 A MX PA06013329A
- Authority
- MX
- Mexico
- Prior art keywords
- carbonitrile
- azabicyclo
- oct
- naphthalene
- endo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 248
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 22
- 201000010099 disease Diseases 0.000 title claims abstract description 9
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- 150000001875 compounds Chemical class 0.000 claims abstract description 306
- 102000001307 androgen receptors Human genes 0.000 claims abstract description 39
- 108010080146 androgen receptors Proteins 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 25
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- -1 nitro, cyano, hydroxy, amino Chemical group 0.000 claims description 299
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- MENILFUADYEXNU-DTORHVGOSA-N tert-butyl (1r,5s)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C(=O)OC(C)(C)C MENILFUADYEXNU-DTORHVGOSA-N 0.000 description 1
- KHPQHXGYYXYTDN-UHFFFAOYSA-N tert-butyl n-(piperidin-3-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCCNC1 KHPQHXGYYXYTDN-UHFFFAOYSA-N 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
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- 230000001052 transient effect Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
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- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- Gynecology & Obstetrics (AREA)
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| US57196104P | 2004-05-17 | 2004-05-17 | |
| PCT/US2005/017143 WO2005115361A2 (en) | 2004-05-17 | 2005-05-16 | Androgen receptor modulators and method of treating disease using the same |
Publications (1)
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| MXPA06013329A true MXPA06013329A (es) | 2007-02-22 |
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| EP (1) | EP1756101A2 (enExample) |
| JP (1) | JP2007538085A (enExample) |
| CN (1) | CN101248069A (enExample) |
| AU (1) | AU2005247405A1 (enExample) |
| CA (1) | CA2566942A1 (enExample) |
| MX (1) | MXPA06013329A (enExample) |
| RU (1) | RU2006144863A (enExample) |
| WO (1) | WO2005115361A2 (enExample) |
| ZA (1) | ZA200610270B (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1636167A2 (en) * | 2003-06-10 | 2006-03-22 | SmithKline Beecham Corporation | 1-aminonaphthalenes as modulators of androgen, glucocorticoid, mineralocorticoid and progesterone receptors |
| US20070004679A1 (en) * | 2004-05-17 | 2007-01-04 | Nathalie Schlienger | Androgen receptor modulators and methods of treating disease using the same |
| CN101248069A (zh) * | 2004-05-17 | 2008-08-20 | 阿卡蒂亚药品公司 | 雄激素受体调节剂及用其治疗疾病的方法 |
| US20060173037A1 (en) * | 2005-01-10 | 2006-08-03 | Nathalie Schlienger | Aminophenyl derivatives as selective androgen receptor modulators |
| KR20070112775A (ko) * | 2005-01-10 | 2007-11-27 | 아카디아 파마슈티칼스 인코포레이티드 | 선택적인 안드로겐 수용체 조절자로서의 아미노페닐 유도체 |
| US7709516B2 (en) * | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
| US20070014739A1 (en) * | 2005-07-14 | 2007-01-18 | Eldridge Gary R | Compositions and methods for controlling biofilms and bacterial infections |
| WO2008066117A1 (en) | 2006-11-30 | 2008-06-05 | Takeda Pharmaceutical Company Limited | Cyclic amine compound |
| US9284345B2 (en) | 2007-04-12 | 2016-03-15 | Endorecherche, Inc. | 17alpha-substituted steroids as systemic antiandrogens and selective androgen receptor modulators |
| EA017429B1 (ru) | 2007-08-07 | 2012-12-28 | Такеда Фармасьютикал Компани Лимитед | Циклические аминные соединения |
| MX2010006972A (es) | 2007-12-21 | 2010-08-26 | Ligand Pharm Inc | Moduladores selectivos de receptores de andrógenos (sarm) y usos de los mismos. |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| MX2010009162A (es) | 2008-02-22 | 2010-12-21 | Radius Health Inc | Moduladores selectivos del receptor de androgeno. |
| US7804063B2 (en) | 2008-10-06 | 2010-09-28 | Quest Diagnostics Investments Incorporated | Methods for detecting dihydrotestosterone by mass spectrometry |
| WO2010054183A2 (en) * | 2008-11-07 | 2010-05-14 | President And Fellows Of Harvard College | Dyes, compositions and related methods of use |
| EP2531029B1 (en) | 2010-02-04 | 2016-10-19 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2011143469A1 (en) | 2010-05-12 | 2011-11-17 | Radius Health,Inc | Therapeutic regimens |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| BR112013007685B1 (pt) | 2010-09-28 | 2021-11-09 | Radius Pharmaceuticals, Inc | Compostos moduladores de receptor andrógeno seletivos, composição farmacêutica compreendendo os referidos compostos, método de identificação de um composto capaz de modular um receptor andrógeno, usos de um composto ou da composição e processo para a preparação de um composto |
| US9175291B2 (en) | 2012-10-11 | 2015-11-03 | Isis Pharmaceuticals Inc. | Modulation of androgen receptor expression |
| MY176727A (en) * | 2012-12-03 | 2020-08-20 | Pfizer | Selective androgen receptor modulators |
| JP6483666B2 (ja) | 2013-10-14 | 2019-03-13 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 選択的に置換されたキノリン化合物 |
| WO2015057659A1 (en) | 2013-10-14 | 2015-04-23 | Eisai R&D Management Co., Ltd. | Selectively substituted quinoline compounds |
| US9682960B2 (en) | 2013-12-19 | 2017-06-20 | Endorecherche, Inc. | Non-steroidal antiandrogens and selective androgen receptor modulators with a pyridyl moiety |
| EP3094323A4 (en) | 2014-01-17 | 2017-10-11 | Ligand Pharmaceuticals Incorporated | Methods and compositions for modulating hormone levels |
| CA2950390C (en) * | 2014-05-30 | 2020-09-22 | Pfizer Inc. | Carbonitrile derivatives as selective androgen receptor modulators |
| RU2604681C1 (ru) * | 2015-06-29 | 2016-12-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Ивановская государственная медицинская академия" Министерства здравоохранения Российской Федерации | Способ прогнозирования эффективности лечения хорионическим гонадотропином у мужчин с гипогонадизмом |
| US10568882B2 (en) | 2015-08-21 | 2020-02-25 | Srx Cardio, Llc | Phenylpiperazine proprotein convertase subtilisin/kexin type 9 (PCSK9) modulators and their use |
| WO2017034994A1 (en) | 2015-08-21 | 2017-03-02 | Portola Pharmaceuticals, Inc. | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate pcsk9 protein activity |
| US10865185B2 (en) | 2015-08-21 | 2020-12-15 | Srx Cardio, Llc | Composition and methods of use of tetrahydroisoquinoline small molecules to bind and modulate PCSK9 protein activity |
| EP3889145B1 (en) | 2015-12-17 | 2024-02-21 | Merck Patent GmbH | 8-cyano-5-piperidino-quinolines as tlr7/8 antagonists and their uses for treating immune disorders |
| US20190119236A1 (en) | 2016-02-23 | 2019-04-25 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| JP7221699B2 (ja) | 2016-06-22 | 2023-02-14 | エリプセス ファーマ エルティーディー | Ar+乳癌の治療方法 |
| WO2018031434A1 (en) | 2016-08-08 | 2018-02-15 | Merck Patent Gmbh | Tlr7/8 antagonists and uses thereof |
| JP7239554B2 (ja) * | 2017-07-18 | 2023-03-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Tlr7/8アンタゴニストおよびそれらの使用 |
| EA202092436A1 (ru) | 2018-05-14 | 2021-05-04 | Нувейшн Био Инк. | Противораковые соединения, нацеливающие на ядерные гормональные рецепторы |
| US20210323977A1 (en) * | 2018-08-28 | 2021-10-21 | Hoffmann-La Roche Inc. | Pyrrolidinyl amide compounds for the treatment of autoimmune disease |
| EP3956309A4 (en) | 2019-04-19 | 2023-06-07 | Ligand Pharmaceuticals Inc. | CRYSTALLINE FORMS AND METHODS FOR PRODUCING CRYSTALLINE FORMS OF A COMPOUND |
| CA3138197A1 (en) | 2019-05-14 | 2020-11-19 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| US11952349B2 (en) | 2019-11-13 | 2024-04-09 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| IL306010A (en) | 2021-03-23 | 2023-11-01 | Nuvation Bio Inc | Anticancer compounds against the nuclear hormone receptor |
| JP2024516024A (ja) | 2021-05-03 | 2024-04-11 | ニューベイション・バイオ・インコーポレイテッド | 抗がん核内ホルモン受容体標的化化合物 |
| CN116554067A (zh) * | 2023-05-08 | 2023-08-08 | 瑞博(杭州)医药科技有限公司 | 一种取代磺酸类化合物的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL140992B (nl) * | 1963-07-06 | 1974-01-15 | Kalle Ag | Kopieermateriaal, dat een lichtgevoelig diazoniumzout bevat en werkwijze voor het bereiden van dat zout. |
| US4933447A (en) * | 1987-09-24 | 1990-06-12 | Ss Pharmaceutical Co., Ltd. | Quinoline derivatives |
| JPH01156960A (ja) * | 1987-09-24 | 1989-06-20 | Ss Pharmaceut Co Ltd | キノリン誘導体 |
| US5707798A (en) * | 1993-07-13 | 1998-01-13 | Novo Nordisk A/S | Identification of ligands by selective amplification of cells transfected with receptors |
| KR100392216B1 (ko) * | 1994-11-15 | 2003-10-17 | 파마시아 앤드 업존 캄파니 | 이환상옥사진및티아진옥사졸리디논항세균물질 |
| AT403803B (de) * | 1996-04-19 | 1998-05-25 | Sanochemia Ltd | Neue benzazepinderivate, diese enthaltende arzneimittel und verwendung derselben zum herstellen von arzneimitteln |
| CA2333332A1 (en) * | 1998-06-05 | 1999-12-16 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| AU754529B2 (en) * | 1998-09-22 | 2002-11-21 | Yamanouchi Pharmaceutical Co., Ltd. | Cyanophenyl derivatives |
| DE10134785A1 (de) | 2001-07-17 | 2003-02-06 | Diehl Munitionssysteme Gmbh | Verfahren zur Flugbahnkorrektur ballistisch verschossener drallstabilisierter Artilleriemunition |
| US6670386B2 (en) * | 2001-07-31 | 2003-12-30 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| TW200407324A (en) * | 2002-05-17 | 2004-05-16 | Bristol Myers Squibb Co | Bicyclic modulators of androgen receptor function |
| US7405234B2 (en) * | 2002-05-17 | 2008-07-29 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| KR20050044902A (ko) | 2002-08-12 | 2005-05-13 | 다케다 야쿠힌 고교 가부시키가이샤 | 축합 벤젠 유도체 및 용도 |
| US6933311B2 (en) * | 2003-02-11 | 2005-08-23 | Abbott Laboratories | Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor |
| US20050113576A1 (en) * | 2003-08-05 | 2005-05-26 | Chih-Hung Lee | Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor |
| US8519158B2 (en) * | 2004-03-12 | 2013-08-27 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
| CN101248069A (zh) * | 2004-05-17 | 2008-08-20 | 阿卡蒂亚药品公司 | 雄激素受体调节剂及用其治疗疾病的方法 |
-
2005
- 2005-05-16 CN CNA2005800238644A patent/CN101248069A/zh active Pending
- 2005-05-16 US US11/130,669 patent/US7268232B2/en not_active Expired - Fee Related
- 2005-05-16 JP JP2007527347A patent/JP2007538085A/ja active Pending
- 2005-05-16 CA CA002566942A patent/CA2566942A1/en not_active Abandoned
- 2005-05-16 AU AU2005247405A patent/AU2005247405A1/en not_active Abandoned
- 2005-05-16 WO PCT/US2005/017143 patent/WO2005115361A2/en not_active Ceased
- 2005-05-16 EP EP05749623A patent/EP1756101A2/en not_active Withdrawn
- 2005-05-16 ZA ZA200610270A patent/ZA200610270B/en unknown
- 2005-05-16 RU RU2006144863/04A patent/RU2006144863A/ru not_active Application Discontinuation
- 2005-05-16 MX MXPA06013329A patent/MXPA06013329A/es not_active Application Discontinuation
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2007
- 2007-06-28 US US11/770,586 patent/US20080009489A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7268232B2 (en) | 2007-09-11 |
| ZA200610270B (en) | 2008-06-25 |
| CN101248069A (zh) | 2008-08-20 |
| WO2005115361A3 (en) | 2006-03-16 |
| JP2007538085A (ja) | 2007-12-27 |
| CA2566942A1 (en) | 2005-12-08 |
| EP1756101A2 (en) | 2007-02-28 |
| RU2006144863A (ru) | 2008-06-27 |
| US20080009489A1 (en) | 2008-01-10 |
| US20060014739A1 (en) | 2006-01-19 |
| AU2005247405A1 (en) | 2005-12-08 |
| WO2005115361A2 (en) | 2005-12-08 |
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| FA | Abandonment or withdrawal |