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Discovery of AZD9833, a Potent and Orally Bioavailable Selective Estrogen Receptor Degrader and Antagonist.
Scott, James S; Moss, Thomas A; Balazs, Amber; Barlaam, Bernard; Breed, Jason; Carbajo, Rodrigo J; Chiarparin, Elisabetta; Davey, Paul R J; Delpuech, Oona; Fawell, Stephen; Fisher, David I; Gagrica, Sladjana; Gangl, Eric T; Grebe, Tyler; Greenwood, Ryan D; Hande, Sudhir; Hatoum-Mokdad, Holia; Herlihy, Kara; Hughes, Samantha; Hunt, Thomas A; Huynh, Hoan; Janbon, Sophie L M; Johnson, Tony; Kavanagh, Stefan; Klinowska, Teresa; Lawson, Mandy; Lister, Andrew S; Marden, Stacey; McGinnity, Dermot F; Morrow, Christopher J; Nissink, J Willem M; O'Donovan, Daniel H; Peng, Bo; Polanski, Radoslaw; Stead, Darren S; Stokes, Stephen; Thakur, Kumar; Throner, Scott R; Tucker, Michael J; Varnes, Jeffrey; Wang, Haixia; Wilson, David M; Wu, Dedong; Wu, Ye; Yang, Bin; Yang, Wenzhan.
Afiliación
  • Scott JS; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Moss TA; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Balazs A; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Barlaam B; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Breed J; Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Carbajo RJ; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Chiarparin E; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Davey PRJ; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Delpuech O; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Fawell S; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Fisher DI; Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Gagrica S; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Gangl ET; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Grebe T; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Greenwood RD; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Hande S; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Hatoum-Mokdad H; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Herlihy K; Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Hughes S; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Hunt TA; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Huynh H; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Janbon SLM; Early Chemical Development, Pharmaceutical Sciences, R&D, Macclesfield, United Kingdom.
  • Johnson T; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Kavanagh S; Oncology Safety, Clinical Pharmacology and Safety Sciences, R&D, AstraZeneca, Cambridge, United Kingdom.
  • Klinowska T; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Lawson M; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Lister AS; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Marden S; Advanced Drug Delivery, Pharmaceutical Sciences, R&D, Boston, Massachusetts, United States.
  • McGinnity DF; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Morrow CJ; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Nissink JWM; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • O'Donovan DH; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Peng B; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Polanski R; Discovery Sciences R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Stead DS; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Stokes S; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Thakur K; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Throner SR; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Tucker MJ; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Varnes J; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Wang H; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Wilson DM; Oncology R&D, AstraZeneca, Cambridge CB4 0WG, United Kingdom.
  • Wu D; Advanced Drug Delivery, Pharmaceutical Sciences, R&D, Boston, Massachusetts, United States.
  • Wu Y; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Yang B; Oncology R&D, AstraZeneca, R&D Boston, 35 Gatehouse Drive, Waltham, Massachusetts 02451, United States.
  • Yang W; Advanced Drug Delivery, Pharmaceutical Sciences, R&D, Boston, Massachusetts, United States.
J Med Chem ; 63(23): 14530-14559, 2020 12 10.
Article en En | MEDLINE | ID: mdl-32910656
Herein we report the optimization of a series of tricyclic indazoles as selective estrogen receptor degraders (SERD) and antagonists for the treatment of ER+ breast cancer. Structure based design together with systematic investigation of each region of the molecular architecture led to the identification of N-[1-(3-fluoropropyl)azetidin-3-yl]-6-[(6S,8R)-8-methyl-7-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-3H-pyrazolo[4,3-f]isoquinolin-6-yl]pyridin-3-amine (28). This compound was demonstrated to be a highly potent SERD that showed a pharmacological profile comparable to fulvestrant in its ability to degrade ERα in both MCF-7 and CAMA-1 cell lines. A stringent control of lipophilicity ensured that 28 had favorable physicochemical and preclinical pharmacokinetic properties for oral administration. This, combined with demonstration of potent in vivo activity in mouse xenograft models, resulted in progression of this compound, also known as AZD9833, into clinical trials.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Moduladores Selectivos de los Receptores de Estrógeno / Antineoplásicos Límite: Female / Humans Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Reino Unido Pais de publicación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Moduladores Selectivos de los Receptores de Estrógeno / Antineoplásicos Límite: Female / Humans Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Reino Unido Pais de publicación: Estados Unidos