Reverse hydroxamate-based selective TACE inhibitors

被引:30
作者
Kamei, N [1 ]
Tanaka, T [1 ]
Kawai, K [1 ]
Miyawaki, K [1 ]
Okuyama, A [1 ]
Murakami, Y [1 ]
Arakawa, Y [1 ]
Haino, M [1 ]
Harada, T [1 ]
Shimano, M [1 ]
机构
[1] Kaken Pharmaceut Co Ltd, Yamashina Ku, Kyoto 6078042, Japan
关键词
D O I
10.1016/j.bmcl.2004.03.048
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Reverse hydroxamate-based selective TACE inhibitors are described. They have potent TACE inhibitory activities and excellent selectivities against MMP-1, 2, 3, 8, 9, 13, 14, and 17. One representative compound, 18 has demonstrated an excellent oral inhibitory activity of the lipopolysaccharide (LPS)-stimulated TNF-alpha production in rats. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2897 / 2900
页数:4
相关论文
共 37 条
[1]   A metalloproteinase disintegrin that releases tumour-necrosis factor-alpha from cells [J].
Black, RA ;
Rauch, CT ;
Kozlosky, CJ ;
Peschon, JJ ;
Slack, JL ;
Wolfson, MF ;
Castner, BJ ;
Stocking, KL ;
Reddy, P ;
Srinivasan, S ;
Nelson, N ;
Boiani, N ;
Schooley, KA ;
Gerhart, M ;
Davis, R ;
Fitzner, JN ;
Johnson, RS ;
Paxton, RJ ;
March, CJ ;
Cerretti, DP .
NATURE, 1997, 385 (6618) :729-733
[2]   NOVEL INDOLACTAM-BASED INHIBITORS OF MATRIX METALLOPROTEINASES [J].
CASTELHANO, AL ;
BILLEDEAU, R ;
DEWDNEY, N ;
DONNELLY, S ;
HORNE, S ;
KURZ, LJ ;
LIAK, TJ ;
MARTIN, R ;
UPPINGTON, R ;
YUAN, ZY ;
KRANTZ, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (13) :1415-1420
[3]   Efficacy and safety of infliximab monotherapy for plaque-type psoriasis: a randomised trial [J].
Chaudhari, U ;
Romano, P ;
Mulcahy, LD ;
Dooley, LT ;
Baker, DG ;
Gottlieb, AB .
LANCET, 2001, 357 (9271) :1842-1847
[4]   Design, synthesis, and evaluation of benzothiadiazepine hydroxamates as selective tumor necrosis factor-α converting enzyme inhibitors [J].
Cherney, RJ ;
Duan, JJW ;
Voss, ME ;
Chen, LH ;
Wang, L ;
Meyer, DT ;
Wasserman, ZR ;
Hardman, KD ;
Liu, RQ ;
Covington, MB ;
Qian, MX ;
Mandlekar, S ;
Christ, DD ;
Trzaskos, JM ;
Newton, RC ;
Magolda, RL ;
Wexler, RR ;
Decicco, CP .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (10) :1811-1823
[5]   Discovery of N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE) [J].
Duan, JJW ;
Lu, ZH ;
Xue, CB ;
He, XH ;
Seng, JL ;
Roderick, JJ ;
Wasserman, ZR ;
Liu, RQ ;
Covington, MB ;
Magolda, RL ;
Newton, RC ;
Trzaskos, JM ;
Decicco, CP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (12) :2035-2040
[6]   Anti-TNFα therapy of rheumatoid arthritis:: what have we learned? [J].
Feldmann, M ;
Maini, RN .
ANNUAL REVIEW OF IMMUNOLOGY, 2001, 19 :163-196
[7]   Pharmacodynamic and pharmacokinetic response to anti-tumor necrosis factor-α monoclonal antibody (infliximab) treatment of moderate to severe psoriasis vulgaris [J].
Gottlieb, AB ;
Masud, S ;
Ramamurthi, R ;
Abdulghani, A ;
Romano, P ;
Chaudhari, U ;
Dooley, LT ;
Fasanmade, AA ;
Wagner, CL .
JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, 2003, 48 (01) :68-75
[8]   MT1-MMP-deficient mice develop dwarfism, osteopenia, arthritis, and connective tissue disease due to inadequate collagen turnover [J].
Holmbeck, K ;
Bianco, P ;
Caterina, J ;
Yamada, S ;
Kromer, M ;
Kuznetsov, SA ;
Mankani, M ;
Robey, PG ;
Poole, AR ;
Pidoux, I ;
Ward, JM ;
Birkedal-Hansen, H .
CELL, 1999, 99 (01) :81-92
[9]   Tumor necrosis factor-α monoclonal antibody, infliximab, used to manage severe sciatica [J].
Karppinen, J ;
Korhonen, T ;
Malmivaara, A ;
Paimela, L ;
Kyllönen, E ;
Lindgren, KA ;
Rantanen, P ;
Tervonen, O ;
Niinimäki, J ;
Seitsalo, S ;
Hurri, H .
SPINE, 2003, 28 (08) :750-753
[10]   Etanercept as monotherapy in patients with psoriasis [J].
Leonardi, CL ;
Powers, JL ;
Matheson, RT ;
Goffe, BS ;
Zitnik, R ;
Wang, A ;
Gottlieb, AB ;
Bagel, J ;
Camisa, C ;
Caro, I ;
DiGiovanna, JJ ;
Dunlap, FF ;
Elewski, BE ;
Gribetz, CE ;
Farber, HF ;
Feldman, SR ;
Frankel, EH ;
Gaspari, AA ;
Goodman, JJ ;
Gordon, KB ;
Hampel, FC ;
Herdener, RS ;
Hoffman, MD ;
Humeniuk, JM ;
Johnson, SM ;
Kang, S ;
Kimball, AB ;
Kirsner, RS ;
Korman, NJ ;
Krueger, GG ;
Kuwahara, RT ;
Lebwohl, M ;
Ling, MR ;
Liu, DC ;
Lowe, N ;
McCall, CO ;
Menter, A ;
Miller, BH ;
Moore, JK ;
Nayak, AS ;
Ratner, PH ;
Savin, RC ;
Shupack, JL ;
Smith, SL ;
Stone, SP ;
Swinehart, JM ;
Taborn, J ;
Tschen, EH ;
Weinstein, GD ;
Werth, VP .
NEW ENGLAND JOURNAL OF MEDICINE, 2003, 349 (21) :2014-2022