633303-33-0

Upstream product

• 633303-36-3 17-(cyclopropylmethyl)-4,5α-epoxy-14β-hydroxy-3-(triphenylmethoxy)morphinan-6-one ethane-1,2-diyl acetal 
• 16676-32-7 (4'R,4a'S,7a'R,12b'S)-3'-(cyclopropylmethyl)-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-4a',9'-diol 
• 646032-66-8 17-(cyclopropylmethyl)-4,5α-epoxy-14β-[(2-methylbenzyl)oxy]-3-(triphenylmethoxy)morphinan-6-one ethane-1,2-diyl acetal 

Relevant academic research and scientific papers

MORPHINAN DERIVATIVES THE QUATERNARY AMMONIUM SALTS THEREOF SUBSTITUTED IN POSITION 14, METHOD FOR PRODUCTION AND USE THEREOF

The invention relates to a class of morphinan compounds and the quaternary ammonium salts thereof, substituted in position 14, which may be used as highly-active analgesics or also as opioid antagonists. The invention further relates to the pharmaceutically-acceptable salts and easily-produced derivatives thereof, a process for production thereof and use thereof in the production of pharmaceutical specialities.

Synthesis and biological evaluation of 14-alkoxymorphinans. Part 19: Effect of 14-O-benzylation on the opioid receptor affinity and antagonist potency of naltrexone

The 14-O-benzylnaltrexones 3-6 were prepared from naltrexone (2) in several steps. The novel compounds were biologically evaluated in radioligand binding and in [35S]GTPγS functional assays in comparison to the reference compound naltrexone. In the binding assay, compounds 3-6 exhibited preference for κ opioid receptors, while the parent compound naltrexone shows preference for μ receptors. In the functional assay, μ antagonist potency of compounds 3-6 was in the range of naltrexone, while K antagonist potency was considerably higher for most novel compounds in comparison to naltrexone.