AN EFFICIENT SYNTHESIS OF THE BENZHYDRYLPIPERAZINE DELTA-OPIOID AGONIST (+)-BW373U86

被引:66
|
作者
BISHOP, MJ
MCNUTT, RW
机构
[1] Division of Organic Chemistry, Burroughs Wellcome Co., Research Triangle Park
关键词
D O I
10.1016/0960-894X(95)00213-D
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A diastereoselective version of Katritzky's method for tertiary amine formation provides an efficient route to the highly selective, non-peptidal, delta opioid agonist (+)-4-[(alpha R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl]-N,N-diethylbenzamide[(+)-BW373U86], 1.
引用
收藏
页码:1311 / 1314
页数:4
相关论文
共 50 条
  • [31] A RAPID AND EFFICIENT SYNTHESIS OF THE DELTA-OPIOID AGONIST, DELTORPHIN
    SIVANANDAIAH, KM
    BABU, VVS
    RENUKESHWAR, HC
    GANGADHAR, BP
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1993, 32 (04): : 465 - 467
  • [32] Buproprion-induced convulsions differ from delta opioid induced seizures of BW373U86:: antagonist studies of neurotransmitter mechanism
    O'Neill, S
    Holt, JDS
    Millard, DB
    Gengo, PJ
    Chang, KJ
    FASEB JOURNAL, 2003, 17 (05): : A1024 - A1024
  • [33] BW373U86, ITS ENANTIOMERS, AND RELATED-COMPOUNDS - INTERACTIONS OF NONPEPTIDE DELTA-AGONISTS AT MULTIPLE DELTA(CX) BINDING-SITES IN RAT-BRAIN
    CHA, XY
    XU, H
    CALDERON, SN
    SMITH, LE
    RICE, KC
    PORRECA, F
    ROTHMAN, RB
    REGULATORY PEPTIDES, 1994, 54 (01) : 45 - 46
  • [34] PROGLUMIDE EXHIBITS DELTA-OPIOID AGONIST PROPERTIES
    REZVANI, A
    STOKES, KB
    RHOADS, DL
    WAY, EL
    ALCOHOL AND DRUG RESEARCH, 1987, 7 (03): : 135 - 146
  • [35] Rapid in vivo metabolism of a methylether derivative of (+/-)-BW373U86: The metabolic fate of [H-3]SNC121 in rats
    Schetz, JA
    Calderon, SN
    Bertha, CM
    Rice, K
    Porreca, F
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 1996, 279 (03): : 1069 - 1076
  • [36] SYNTHESIS OF A C-14 LABELED DELTA-OPIOID RECEPTOR AGONIST BY CARBONYLATION
    Elmore, Charles S.
    Frietze, William E.
    Andisik, Donald W.
    Ernst, Glen E.
    Heys, J. Richard
    Dantzman, Cathy L.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2010, 53 (5-6): : 394 - 397
  • [37] Dopamine-dependent behavioural stimulation by non-peptide delta opioids BW373U86 and SNC 80: 1. Locomotion, rearing and stereotypies in intact rats
    Spina, L
    Longoni, R
    Mulas, A
    Chang, KJ
    Di Chiara, G
    BEHAVIOURAL PHARMACOLOGY, 1998, 9 (01): : 1 - 8
  • [38] Synthesis of delta-opioid agonists.
    Craft, L
    DiCesare, JC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U129 - U129
  • [39] PROPERTIES OF TAN-67, A NONPEPTIDIC DELTA-OPIOID RECEPTOR AGONIST, AT CLONED HUMAN DELTA-OPIOID AND MU-OPIOID RECEPTORS
    KNAPP, RJ
    LANDSMAN, R
    WAITE, S
    MALATYNSKA, E
    VARGA, E
    HAQ, W
    HRUBY, VJ
    ROESKE, WR
    NAGASE, H
    YAMAMURA, HI
    EUROPEAN JOURNAL OF PHARMACOLOGY-MOLECULAR PHARMACOLOGY SECTION, 1995, 291 (02): : 129 - 134
  • [40] BIPHASIC RESPIRATORY EFFECTS OF A CENTRAL DELTA-OPIOID RECEPTOR AGONIST
    WOOD, DL
    WEINGER, MB
    FURST, SR
    COLEMAN, MJ
    ANESTHESIOLOGY, 1994, 81 (3A) : A1409 - A1409