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Identification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)

The design of a new clinical candidate histamine-H receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl- -2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with a sulfone. One... Full description

Journal Title: Bioorganic & Medicinal Chemistry Letters 01 January 2012, Vol.22(1), pp.71-75
Main Author: Semple, Graeme
Other Authors: Santora, Vincent J , Smith, Jeffrey M , Covel, Jonathan A , Hayashi, Rena , Gallardo, Charlemagne , Ibarra, Jason B , Schultz, Jeffrey A , Park, Douglas M , Estrada, Scott A , Hofilena, Brian J , Smith, Brian M , Ren, Albert , Suarez, Marissa , Frazer, John , Edwards, Jeffrey E , Hart, Ryan , Hauser, Erin K , Lorea, Jodie , Grottick, Andrew J
Format: Electronic Article Electronic Article
Language: English
Subjects:
CNS
ID: ISSN: 0960-894X ; E-ISSN: 1464-3405 ; DOI: 10.1016/j.bmcl.2011.11.075
Link: https://www.sciencedirect.com/science/article/pii/S0960894X11016192
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recordid: elsevier_sdoi_10_1016_j_bmcl_2011_11_075
title: Identification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)
format: Article
creator:
  • Semple, Graeme
  • Santora, Vincent J
  • Smith, Jeffrey M
  • Covel, Jonathan A
  • Hayashi, Rena
  • Gallardo, Charlemagne
  • Ibarra, Jason B
  • Schultz, Jeffrey A
  • Park, Douglas M
  • Estrada, Scott A
  • Hofilena, Brian J
  • Smith, Brian M
  • Ren, Albert
  • Suarez, Marissa
  • Frazer, John
  • Edwards, Jeffrey E
  • Hart, Ryan
  • Hauser, Erin K
  • Lorea, Jodie
  • Grottick, Andrew J
subjects:
  • Histamine-H3 Antagonist
  • Sleep
  • Wakefulness
  • CNS
  • Herg
  • Clinical Candidate
  • Medicine
  • Chemistry
  • Anatomy & Physiology
ispartof: Bioorganic & Medicinal Chemistry Letters, 01 January 2012, Vol.22(1), pp.71-75
description: The design of a new clinical candidate histamine-H receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl- -2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with a sulfone. One compound from this series, (APD916) increased wakefulness in rodents as measured by polysomnography with a duration of effect consistent with its pharmacokinetic properties. The identification of a suitable salt form of allowed it to be selected for further development. The design of a new clinical candidate histamine-H receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl- -2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with...
language: eng
source:
identifier: ISSN: 0960-894X ; E-ISSN: 1464-3405 ; DOI: 10.1016/j.bmcl.2011.11.075
fulltext: fulltext
issn:
  • 0960-894X
  • 0960894X
  • 1464-3405
  • 14643405
url: Link


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titleIdentification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)
creatorSemple, Graeme ; Santora, Vincent J ; Smith, Jeffrey M ; Covel, Jonathan A ; Hayashi, Rena ; Gallardo, Charlemagne ; Ibarra, Jason B ; Schultz, Jeffrey A ; Park, Douglas M ; Estrada, Scott A ; Hofilena, Brian J ; Smith, Brian M ; Ren, Albert ; Suarez, Marissa ; Frazer, John ; Edwards, Jeffrey E ; Hart, Ryan ; Hauser, Erin K ; Lorea, Jodie ; Grottick, Andrew J
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subjectHistamine-H3 Antagonist ; Sleep ; Wakefulness ; CNS ; Herg ; Clinical Candidate ; Medicine ; Chemistry ; Anatomy & Physiology
descriptionThe design of a new clinical candidate histamine-H receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl- -2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with a sulfone. One compound from this series, (APD916) increased wakefulness in rodents as measured by polysomnography with a duration of effect consistent with its pharmacokinetic properties. The identification of a suitable salt form of allowed it to be selected for further development. The design of a new clinical candidate histamine-H receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl- -2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with...
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atitleIdentification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)
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