Discovery of the first potent and selective small molecule opioid receptor-like (ORL1) antagonist:: 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (J-113397)

被引：198
|
作者：
Kawamoto, H [1 ]
Ozaki, S [1 ]
Itoh, Y [1 ]
Miyaji, M [1 ]
Arai, S [1 ]
Nakashima, H [1 ]
Kato, T [1 ]
Ohta, H [1 ]
Iwasawa, Y [1 ]
机构：
[1] Banyu Pharmaceut Co Ltd, Merck Res Labs, Banyu Tsukuba Res Inst, Tsukuba, Ibaraki 3002611, Japan
来源：
JOURNAL OF MEDICINAL CHEMISTRY | 1999年 / 42卷 / 25期
关键词：
D O I：
10.1021/jm990517p
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
引用
收藏
页码：5061 / 5063
页数：3
相关论文
共 50 条
  • [1] Improved synthesis of the ORL antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-ethoxycarbonyl-4-piperidinyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (J-113397)
    Carroll, F. Ivy
    Brieaddy, Lawrence E.
    SYNTHETIC COMMUNICATIONS, 2008, 38 (12) : 1926 - 1930
  • [2] A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one (J-113397), the first non-peptide ORL-1 receptor antagonist
    De Risi, C
    Pollini, GP
    Trapella, C
    Peretto, I
    Ronzoni, S
    Giardina, GAM
    BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (07) : 1871 - 1877
  • [3] Synthesis and evaluation of 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-[11C]ethyl-1,3-dihydro-2H-benzimidazol-2-one as a brain ORL1 receptor imaging agent for positron emission tomography
    Ogawa, M
    Hatano, K
    Kawasumi, Y
    Ishiwata, K
    Kawamura, K
    Ozaki, S
    Ito, K
    NUCLEAR MEDICINE AND BIOLOGY, 2003, 30 (01) : 51 - 59
  • [4] A new synthesis of the ORL-1 antagonist 1-1(3R,4R)-1-cyclooctrlmethyl-3-hydroxymethyl-4-piperidinyl]3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (J-113397) and activity in a calcium mobilization assay
    Smith, Emilie D.
    Vinson, N. Ariane
    Zhong, Desong
    Berrang, Bertold D.
    Catanzaro, Jennifer L.
    Thomas, James B.
    Navarro, Hernan A.
    Gilmour, Brian P.
    Deschamps, Jeffrey
    Carrolla, F. Ivy
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (02) : 822 - 829
  • [5] Identification of an Orally Active Opioid Receptor-like 1 (ORL1) Receptor Antagonist 4-{3-[(2R)-2,3-Dihydroxypropyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-[(1S,3S,4R)-spiro[bicyclo[2.2.1]heptane-2,1′-cyclopropan]-3-ylmethyl]piperidine as Clinical Candidate
    Satoh, Atsushi
    Sagara, Takeshi
    Sakoh, Hiroki
    Hashimoto, Masaya
    Nakashima, Hiroshi
    Kato, Tetsuya
    Goto, Yasuhiro
    Mizutani, Sayaka
    Azuma-Kanoh, Tomoko
    Tani, Takeshi
    Okuda, Shoki
    Okamoto, Osamu
    Ozaki, Satoshi
    Iwasawa, Yoshikazu
    Ohta, Hisashi
    Kawamoto, Hiroshi
    JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (14) : 4091 - 4094
  • [6] Identification of (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide as a novel potent and selective opioid κ receptor antagonist
    Thomas, JB
    Atkinson, RN
    Vinson, NA
    Catanzaro, JL
    Perretta, CL
    Fix, SE
    Mascarella, SW
    Rothman, RB
    Xu, H
    Dersch, CM
    Cantrell, BE
    Zimmerman, DM
    Carroll, FI
    JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) : 3127 - 3137
  • [7] 1-(1-[4-(4-FLUOROPHENYL)-4-OXOBUTYL]-1,2,3,6-TETRAHYDRO-4-PYRIDYL)-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE DIHYDRATE (DEHYDROBENZPERIDOL)
    BLATON, NM
    PEETERS, OM
    DERANTER, CJ
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1980, 36 (NOV): : 2828 - 2830
  • [8] Pharmacological profile and antiparkinsonian properties of the novel nociceptin/orphanin FQ receptor antagonist 1-[1-cyclooctylmethyl-5-(1-hydroxy-1-methyl-ethyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-3-ethyl-1,3-dihydro-benzoimidazol-2-one (GF-4)
    Volta, Mattia
    Marti, Matteo
    McDonald, John
    Molinari, Stefano
    Camarda, Valeria
    Pela, Michela
    Trapella, Claudio
    Morari, Michele
    PEPTIDES, 2010, 31 (06) : 1194 - 1204
  • [9] Synthesis and in vitro opioid receptor functional antagonism of analogues of the selective kappa opioid receptor antagonist (3R)-7-Hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic)
    Cai, Tingwei Bill
    Zou, Zhou
    Thomas, James B.
    Brieaddy, Larry
    Navarro, Hernan A.
    Carroll, F. Ivy
    JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) : 1849 - 1860
  • [10] Analogues of (3R)-7-Hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in Vitro and in Vivo Opioid Receptor Antagonist Activity
    Runyon, Scott P.
    Brieaddy, Lawrence E.
    Mascarella, S. Wayne
    Thomas, James B.
    Navarro, Hernan A.
    Howard, James L.
    Pollard, Gerald T.
    Carroll, F. Ivy
    JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (14) : 5290 - 5301
12345