1029691-07-3Relevant academic research and scientific papers
Origins of Regioselectivity in the Fischer Indole Synthesis of a Selective Androgen Receptor Modulator
Noey, Elizabeth L.,Yang, Zhongyue,Li, Yanwei,Yu, Hannah,Richey, Rachel N.,Merritt, Jeremy M.,Kjell, Douglas P.,Houk
, p. 5904 - 5909 (2017)
The selective androgen receptor modulator, (S)-(7-cyano-4-(pyridin-2-ylmethyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamic acid isopropyl ester, LY2452473, is a promising treatment of side effects of prostate cancer therapies. An acid-catalyzed Fischer indolization is a central step in its synthesis. The reaction leads to only one of the two possible indole regioisomers, along with minor decomposition products. Computations show that the formation of the observed indole is most favored energetically, while the potential pathway to the minor isomer leads instead to decomposition products. The disfavored [3,3]-sigmatropic rearrangement, which would produce the unobserved indole product, is destabilized by the electron-withdrawing phthalimide substituent. The most favored [3,3]-sigmatropic rearrangement transition state is bimodal, leading to two reaction intermediates from one transition state, which is confirmed by molecular dynamics simulations. Both intermediates can lead to the observed indole product, albeit through different mechanisms.
TREATMENT OF ANDROGEN DEPRIVATION THERAPY ASSOCIATED SYMPTOMS
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Paragraph 0037, (2017/07/14)
The present invention provides a method of treating symptoms associated with Androgen Deprivation Therapy comprising administering to a patient in need of such treatment an effective amount of a compound of Formula I: [Formula should be inserted here] or a pharmaceutically acceptable salt thereof.
TETRAHYDROCYCLOPENTA[b] INDOLE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS
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Page/Page column 12, (2010/04/23)
The present invention provides a compound of the formula: Formula (I) or a pharmaceutically acceptable salt thereof; pharmaceutical compositions comprising a compound of Formula (I) in combination with a suitable carrier, diluent, or excipient; and methods for treating physiological disorders, particularly reduced bones mass, osteoporosis, osteopenia, or reduced muscle mass or strength, comprising administering a compound of Formula (I), or a pharmaceutically acceptable salt thereof. X-17142.
