N-methyl-2-[4-(2-methylpropyl)phenyl]-3-(3-methoxy-5-methylpyrazin-2-ylsulfamoyl)benzamide; One of a class of novel benzenesulphonamides which are orally-active, ETA-selective endothelin antagonists

被引:4
|
作者
Mortlock, AA
Bath, C
Butlin, RJ
Heys, C
Hunt, SJ
Reid, AC
Sumner, NF
Tang, EK
Whiting, E
Wilson, C
Wright, ND
机构
[1] ZENECA Pharmaceuticals, Macclesfield, Cheshire, SK10 4TG, Alderley Park
关键词
D O I
10.1016/S0960-894X(97)00228-X
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of novel sulphonamides have been discovered which show high affinity and selectivity for the endothelin ETA receptor. N-Methyl-2-[4-(2-methylpropyl)phenyl]-3-(3-methoxy-5-methylpyrazin-2-yl-sulfamoyl)benzamide (18) is the most widely investigated compound and is a potent antagonist in vivo when dosed either i.v. or orally, and has prolonged oral duration of action. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1399 / 1402
页数:4
相关论文
共 50 条
  • [21] Discovery of 4-{4-[3-(pyridin-2-yl)-1H-pyrazol-4-yl]pyridin-2-yl}-N-(tetrahydro-2H-pyran-4-yl)benzamide (GW788388):: A potent, selective, and orally active transforming growth factor-β type I receptor inhibitor
    Gellibert, F
    de Gouville, AC
    Woolven, J
    Mathews, N
    Nguyen, VL
    Bertho-Ruault, C
    Patikis, A
    Grygielko, ET
    Laping, NJ
    Huet, S
    JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (07) : 2210 - 2221
  • [22] Synthesis and pharmacological evaluation of 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human vasopressin V1A receptor
    Kakefuda, A
    Suzuki, T
    Tobe, T
    Tsukada, J
    Tahara, A
    Sakamoto, S
    Tsukamoto, S
    JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (12) : 2589 - 2598
  • [23] N-[3-(2-dimethylaminoethyl)-2-methyl-1H-indol-5-yl]-4-fluorobenzamide:: A potent, selective, and orally active 5-HT1F receptor agonist potentially useful for migraine therapy
    Xu, YC
    Johnson, KW
    Phebus, LA
    Cohen, M
    Nelson, DL
    Schenck, K
    Walker, CD
    Fritz, JE
    Kaldor, SW
    LeTourneau, ME
    Murff, RE
    Zgombick, JM
    Calligaro, DO
    Audia, JE
    Schaus, JM
    JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (24) : 4031 - 4034
  • [24] SSR240612 [(2R)-2-[((3R)-3-(1,3-benzodioxol-5-yl)-3-{[(6-methoxy-2-naphthyl)sulfonyl]amino}propanoyl)amino]-3-(4-{[2R,6S)-2,6-dimethylpiperidinyl]methyl}phenyl)-N-isopropyl-N-methylpropanamide hydrochloride], a new nonpeptide antagonist of the bradykinin B1 receptor:: Biochemical and pharmacological characterization
    Gougat, J
    Ferrari, B
    Sarran, L
    Planchenault, C
    Poncelet, M
    Maruani, J
    Alonso, R
    Cudennec, A
    Croci, T
    Guagnini, F
    Urban-Szabo, K
    Martinolle, JP
    Soubrié, P
    Finance, O
    Le Fur, G
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2004, 309 (02): : 661 - 669
  • [25] Discovery of a potent, selective, and orally bioavailable c-Met inhibitor:: 1-(2-Hydroxy-2-methylpropyl)-N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (AMG 458)
    Liu, Longbin
    Siegmund, Aaron
    Xi, Ning
    Kaplan-Lefko, Paula
    Rex, Karen
    Cheti, April
    Lin, Jasmine
    Moriguchi, Jodi
    Berry, Loren
    Huang, Liyue
    Teffera, Yohannes
    Yang, Yajing
    Zhang, Yihong
    Bellon, Steven F.
    Lee, Matthew
    Shimanovich, Roman
    Bak, Annette
    Dominguez, Celia
    Norman, Mark H.
    Harmange, Jean-Christophe
    Dussault, Isabelle
    Kimt, Tae-Seong
    JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (13) : 3688 - 3691
  • [26] 5-fluoro-2-methyl-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)-3-chlorophenyl]benzamide (VPA-985):: An orally active arginine vasopressin antagonist with selectivity for V2 receptors
    Albright, JD
    Reich, MF
    Delos Santos, EG
    Dusza, JP
    Sum, FW
    Venkatesan, AM
    Coupet, J
    Chan, PS
    Ru, X
    Mazandarani, H
    Bailey, T
    JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (14) : 2442 - 2444
  • [27] Discovery of 2-((3-Amino-4-methylphenyl)amino)-N-(2-methyl-5-(3-(trifluoromethyl)benzamido)phenyl)-4-(methylamino)pyrimidine-5-carboxamide (CHMFL-ABL-053) as a Potent, Selective, and Orally Available BCR-ABL/SRC/p38 Kinase Inhibitor for Chronic Myeloid Leukemia
    Liang, Xiaofei
    Liu, Xiaochuan
    Wang, Beilei
    Zou, Fengming
    Wang, Aoli
    Qi, Shuan
    Chen, Cheng
    Zhao, Zheng
    Wang, Wenchao
    Qi, Ziping
    Lv, Fengchao
    Hu, Zhenquan
    Wang, Li
    Zhang, Shanchun
    Liu, Qingsong
    Liu, Jing
    JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (05) : 1984 - 2004
  • [28] Discovery of N-{(1S,2S)-2-(3-Cyanophenyl)-3-[4-(2-[18F]fluoroethoxy)phenyl]-1-methylpropyl}-2-methyl-2-[(5-methylpyridin-2-yl)oxy]propanamide, a cannabinoid-1 receptor positron emission tomography tracer suitable for clinical use
    Liu, Ping
    Lin, Linus S.
    Hamill, Terence G.
    Jewell, James P.
    Lanza, Thomas J., Jr.
    Gibson, Raymond E.
    Krause, Stephen M.
    Ryan, Christine
    Eng, Waisi
    Sanabria, Sandra
    Tong, Xinchun
    Wang, Junying
    Levorse, Dorothy A.
    Owens, Karen A.
    Fong, Tung M.
    Shen, Chun-Pyn
    Lao, Julie
    Kumar, Sanjeev
    Yin, Wenji
    Payack, Joseph F.
    Springfield, Shawn A.
    Hargreaves, Richard
    Burns, H. Donald
    Goulet, Mark T.
    Hagmann, William K.
    JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (15) : 3427 - 3430
  • [29] Optimization of a Novel Binding Motif to (E)-3-(3,5-Difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenyl)acrylic Acid (AZD9496), a Potent and Orally Bioavailable Selective Estrogen Receptor Downregulator and Antagonist
    De Savi, Chris
    Bradbury, Robert H.
    Rabow, Alfred A.
    Norman, Richard A.
    de Almeida, Camila
    Andrews, David M.
    Ballard, Peter
    Buttar, David
    Callis, Rowena J.
    Currie, Gordon S.
    Curwen, Jon O.
    Davies, Chris D.
    Donald, Craig S.
    Feron, Lyman J. L.
    Gingell, Helen
    Glossop, Steven C.
    Hayter, Barry R.
    Hussain, Syeed
    Karoutchi, Galith
    Lamont, Scott G.
    MacFaul, Philip
    Moss, Thomas A.
    Pearson, Stuart E.
    Tonge, Michael
    Walker, Graeme E.
    Weir, Hazel M.
    Wilson, Zena
    JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (20) : 8128 - 8140
  • [30] Characterization of (2S,4R)-1-[5-chloro-1-[(2,4-dimethoxyphenyl)sulfonyl]-3-(2-methoxy-phenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-hydroxy-N,N-dimethyl-2-pyrrolidine carboxamide (SSR149415), a selective and orally active vasopressin V1b receptor antagonist
    Serradeil-Le Gal, C
    Wagnon, J
    Simiand, J
    Griebel, G
    Lacour, C
    Guillon, G
    Barberis, C
    Brossard, G
    Soubrié, P
    Nisato, D
    Pascal, M
    Pruss, R
    Scatton, B
    Maffrand, JP
    Le Fur, G
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2002, 300 (03): : 1122 - 1130