Discovery of a structurally novel opioid κ-agonist derived from 4,5- epoxymorphinan

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 2, 1998, Pages 366-369

  Nagase, Hiroshi ^a   Hayakawa, Jun ^a   Kawamura, Kuniaki ^a   Kawai, Kouji ^a   Takezawa, Yuko ^a   Matsuura, Hirotoshi ^a   Tajima, Chiko ^a   Endo, Takashi ^a  

^a TORAY INDUSTRIES INC   (Japan)

Author keywords

Accessory site; Message address concept; Opioid; TRK 820; agonist

Indexed keywords

17 CYCLOPROPYLMETHYL 3,14BETA DIHYDROXY 4,5ALPHA EPOXY 6BETA [N METHYL 3 (3 FURYL)ACRYLAMIDO]MORPHINAN HYDROCHLORIDE; 3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZAMIDE; 4,5 EPOXYMORPHINAN DERIVATIVE; KAPPA OPIATE RECEPTOR AGONIST; OPIATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; DRUG STRUCTURE; GUINEA PIG; HYPOTHESIS; LIGAND BINDING; MOUSE; NONHUMAN; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; TAIL FLICK TEST;

EID: 0031915119     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.366     Document Type: Article

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12. A solution of 3-(3-furyl)acryloyl chloride in anhydrous THF was added to a two-phase solution of compounds in THF and distilled water containing sodium carbonate, and stirred for 1 hour. The sodium hydroxide solution was then added to the reaction solution to hydrolyze the phenol ester. The obtained free base of TRK-820 by extraction and concentration of the solvent was purified by recrystallization from ethyl acetate/methanol. The purified compound was converted to hydrochloride salt using HCl to give TRK-820 in 75% yield. (Equation Presented)
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