Literature DB >> 25893048

Novel benzamide-based histamine h3 receptor antagonists: the identification of two candidates for clinical development.

Michael A Letavic1, Leah Aluisio1, Richard Apodaca1, Manoj Bajpai1, Ann J Barbier1, Anne Bonneville1, Pascal Bonaventure1, Nicholas I Carruthers1, Christine Dugovic1, Ian C Fraser1, Michelle L Kramer1, Brian Lord1, Timothy W Lovenberg1, Lilian Y Li1, Kiev S Ly1, Heather Mcallister1, Neelakandha S Mani1, Kirsten L Morton1, Anthony Ndifor1, S Diane Nepomuceno1, Chennagiri R Pandit1, Steven B Sands1, Chandra R Shah1, Jonathan E Shelton1, Sandra S Snook1, Devin M Swanson1, Wei Xiao1.   

Abstract

The preclinical characterization of novel phenyl(piperazin-1-yl)methanones that are histamine H3 receptor antagonists is described. The compounds described are high affinity histamine H3 antagonists. Optimization of the physical properties of these histamine H3 antagonists led to the discovery of several promising lead compounds, and extensive preclinical profiling aided in the identification of compounds with optimal duration of action for wake promoting activity. This led to the discovery of two development candidates for Phase I and Phase II clinical trials.

Entities:  

Keywords:  Histamine H3 antagonists; histamine; phenyl(piperazin-1-yl)methanones

Year:  2015        PMID： 25893048      PMCID： PMC4394347          DOI： 10.1021/ml5005156

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  13 in total

Review 1.  The histamine H3 receptor: an attractive target for the treatment of cognitive disorders.

Authors:  T A Esbenshade; K E Browman; R S Bitner; M Strakhova; M D Cowart; J D Brioni
Journal:  Br J Pharmacol       Date:  2008-05-12       Impact factor: 8.739

2.  Discovery of two clinical histamine H(3) receptor antagonists: trans-N-ethyl-3-fluoro-3-[3-fluoro-4-(pyrrolidinylmethyl)phenyl]cyclobutanecarboxamide (PF-03654746) and trans-3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]-N-(2-methylpropyl)cyclobutanecarboxamide (PF-03654764).

Authors:  Travis T Wager; Betty A Pettersen; Anne W Schmidt; Douglas K Spracklin; Scot Mente; Todd W Butler; Harry Howard; Daniel J Lettiere; David M Rubitski; Diane F Wong; Frank M Nedza; Frederick R Nelson; Hans Rollema; Jeffrey W Raggon; Jiri Aubrecht; Jody K Freeman; John M Marcek; Julie Cianfrogna; Karen W Cook; Larry C James; Linda A Chatman; Philip A Iredale; Michael J Banker; Michael L Homiski; Jennifer B Munzner; Rama Y Chandrasekaran
Journal:  J Med Chem       Date:  2011-10-07       Impact factor: 7.446

Review 3.  Histamine H3 receptor function and ligands: recent developments.

Authors:  Mahaveer Singh; Hemant R Jadhav
Journal:  Mini Rev Med Chem       Date:  2013-01       Impact factor: 3.862

Review 4.  Selective targets for arousal-modifying drugs: implications for the treatment of sleep disorders.

Authors:  Elemer Szabadi
Journal:  Drug Discov Today       Date:  2014-01-09       Impact factor: 7.851

5.  Pre-clinical characterization of aryloxypyridine amides as histamine H3 receptor antagonists: identification of candidates for clinical development.

Authors:  Michael A Letavic; Leah Aluisio; John R Atack; Pascal Bonaventure; Nicholas I Carruthers; Christine Dugovic; Anita Everson; Mark A Feinstein; Ian C Fraser; Kenway Hoey; Xiaohui Jiang; John M Keith; Tatiana Koudriakova; Perry Leung; Brian Lord; Timothy W Lovenberg; Kiev S Ly; Kirsten L Morton; S Timothy Motley; Diane Nepomuceno; Michele Rizzolio; Raymond Rynberg; Kia Sepassi; Jonathan Shelton
Journal:  Bioorg Med Chem Lett       Date:  2010-05-16       Impact factor: 2.823

6.  Pharmacological characterization of JNJ-28583867, a histamine H(3) receptor antagonist and serotonin reuptake inhibitor.

Authors:  Ann J Barbier; Leah Aluisio; Brian Lord; Ying Qu; Sandy J Wilson; Jamin D Boggs; Pascal Bonaventure; Kirsten Miller; Ian Fraser; Lisa Dvorak; Cindy Pudiak; Christine Dugovic; Jonathan Shelton; Curt Mazur; Michael A Letavic; Nicholas I Carruthers; Timothy W Lovenberg
Journal:  Eur J Pharmacol       Date:  2007-08-14       Impact factor: 4.432

Review 7.  Histamine H3 receptor antagonists go to clinics.

Authors:  Kerstin Sander; Tim Kottke; Holger Stark
Journal:  Biol Pharm Bull       Date:  2008-12       Impact factor: 2.233

8.  1-alkyl-4-acylpiperazines as a new class of imidazole-free histamine H(3) receptor antagonists.

Authors:  Florencio Zaragoza; Henrik Stephensen; Sanne M Knudsen; Lone Pridal; Birgitte S Wulff; Karin Rimvall
Journal:  J Med Chem       Date:  2004-05-20       Impact factor: 7.446

9.  Pitolisant versus placebo or modafinil in patients with narcolepsy: a double-blind, randomised trial.

Authors:  Yves Dauvilliers; Claudio Bassetti; Gert Jan Lammers; Isabelle Arnulf; Geert Mayer; Andrea Rodenbeck; Philippe Lehert; Claire-Li Ding; Jeanne-Marie Lecomte; Jean-Charles Schwartz
Journal:  Lancet Neurol       Date:  2013-10-07       Impact factor: 44.182

10.  Selective naphthalene H(3) receptor inverse agonists with reduced potential to induce phospholipidosis and their quinoline analogs.

Authors:  Rosa María Rodríguez Sarmiento; Matthias H Nettekoven; Sven Taylor; Jean-Marc Plancher; Hans Richter; Olivier Roche
Journal:  Bioorg Med Chem Lett       Date:  2009-03-26       Impact factor: 2.823
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  3 in total

1.  Synthesis and biological evaluation of a new class of multi-target heterocycle piperazine derivatives as potential antipsychotics.

Authors:  Lanchang Gao; Chao Hao; Ru Ma; Jiali Chen; Guisen Zhang; Yin Chen
Journal:  RSC Adv       Date:  2021-05-07       Impact factor: 4.036

2.  Mechanochemical Nucleophilic Substitution of Alcohols via Isouronium Intermediates.

Authors:  Tatsiana Dalidovich; Jagadeesh Varma Nallaparaju; Tatsiana Shalima; Riina Aav; Dzmitry G Kananovich
Journal:  ChemSusChem       Date:  2022-01-20       Impact factor: 9.140

3.  Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups.

Authors:  Benjamin Jeffries; Zhong Wang; Robert I Troup; Anaïs Goupille; Jean-Yves Le Questel; Charlene Fallan; James S Scott; Elisabetta Chiarparin; Jérôme Graton; Bruno Linclau
Journal:  Beilstein J Org Chem       Date:  2020-09-02       Impact factor: 2.883
  3 in total

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