Synthesis and biological activity of piperazine and diazepane amides that are histamine H3 antagonists and serotonin reuptake inhibitors

被引:28
作者
Ly, Kiev S.
Letavic, Michael A. [1 ]
Keith, John M. [1 ]
Miller, Jennifer M. [1 ]
Stocking, Emily M. [1 ]
Barbier, Ann J. [1 ]
Bonaventure, Pascal [1 ]
Lord, Brian [1 ]
Jiang, Xiaohui [1 ]
Boggs, Jamin D. [1 ]
Dvorak, Lisa [1 ]
Miller, Kirsten L. [1 ]
Nepomuceno, Diane [1 ]
Wilson, Sandy J. [1 ]
Carruthers, Nicholas I. [1 ]
机构
[1] Johnson & Johnson Pharmaceut Res & Dev LLC, San Diego, CA 92121 USA
关键词
histamine H3 antagonist; serotonin reuptake inhibitor; histamine; serotonin;
D O I
10.1016/j.bmcl.2007.11.016
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis and biological activity of a new series of piperazine and diazepane amides is described. The new compounds are high affinity histamine H-3 ligands and serotonin reuptake inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:39 / 48
页数:10
相关论文
共 7 条
[1]   Non-hydroxamate 5-phenylpyrimidine-2,4,6-trione derivatives as selective inhibitors of tumor necrosis factor-α converting enzyme [J].
Duan, JJW ;
Lu, ZH ;
Wasserman, ZR ;
Liu, RQ ;
Covington, MB ;
Decicco, CP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :2970-2973
[2]   Discovery of γ-lactam hydroxamic acids as selective inhibitors of tumor necrosis factor α converting enzyme:: Design, synthesis, and structure-activity relationships [J].
Duan, JJW ;
Chen, LH ;
Wasserman, ZR ;
Lu, ZH ;
Liu, RQ ;
Covington, MB ;
Qian, MX ;
Hardman, KD ;
Magolda, RL ;
Newton, RC ;
Christ, DD ;
Wexler, RR ;
Decicco, CP .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (23) :4954-4957
[3]  
FELDMANN M, 1994, CIRC SHOCK, V43, P179
[4]   Discovery of a novel series of selective MMP inhibitors:: Identification of the γ-sulfone-thiols [J].
Freskos, JN ;
Mischke, BV ;
DeCrescenzo, GA ;
Heintz, R ;
Getman, DP ;
Howard, SC ;
Kishore, NN ;
McDonald, JJ ;
Munie, GE ;
Rangwala, S ;
Swearingen, CA ;
Voliva, C ;
Welsch, DJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :943-948
[5]   The design and synthesis of aryl hydroxamic acid inhibitors of MMPs and TACE [J].
Levin, JI .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2004, 4 (12) :1289-1310
[6]   Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib) [J].
Penning, TD ;
Talley, JJ ;
Bertenshaw, SR ;
Carter, JS ;
Collins, PW ;
Docter, S ;
Graneto, MJ ;
Lee, LF ;
Malecha, JW ;
Miyashiro, JM ;
Rogers, RS ;
Rogier, DJ ;
Yu, SS ;
Anderson, GD ;
Burton, EG ;
Cogburn, JN ;
Gregory, SA ;
Koboldt, CM ;
Perkins, WE ;
Seibert, K ;
Veenhuizen, AW ;
Zhang, YY ;
Isakson, PC .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (09) :1347-1365
[7]   Novel thiol-based TACE inhibitors: Rational design, synthesis, and SAR of thiol-containing aryl sulfonamides [J].
Rao, B. Govinda ;
Bandarage, Upul K. ;
Wang, Tiansheng ;
Come, Jon H. ;
Perola, Emanuele ;
Wei, Yunyi ;
Tian, Shi-Kai ;
Saunders, Jeffrey O. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (08) :2250-2253