547767-36-2

Upstream product

• 100-39-0 benzyl bromide 
• 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 
• 16590-41-3 Naltrexone 
• 107-21-1 ethylene glycol 
• 153567-11-4 2,2,2-trichloroethyl (4'R,7a'R,12b'S)-9'-(benzyloxy)-1',2',4',6'-tetrahydro-3'H,7a'Hspiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-3'-carboxylate 
• 16676-29-2 naltrexone Hydrochloride 

Downstream Products

• 633303-37-4 3-(benzyloxy)-14β-[(2-chlorobenzyl)oxy]-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-6-one ethane-1,2-diyl acetal 
• 780036-92-2 3-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-14β-[(2-phenylbenzyl)oxy]-morphinane-6-spiro-2'-(1,3-dioxolan) 
• 785047-07-6 3-benzyloxy-14β-[(3-methyl-but-2-enyl)oxy]-17-cyclopropylmethyl-4,5α-epoxy-morphinane-6-spiro-2'-(1,3-dioxolan) 
• 646033-30-9 3-benzyloxy-17-cyclopropylmethyl-14β-[(E)-3-phenyl-prop-2-enyloxy]-4,5α-epoxy-morphinane-6-spiro-2'-(1,3-dioxolan) 
• 646033-16-1 3-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-14β-[(4-chloro-benzyl)oxy]-morphinane-6-spiro-2'-(1,3-dioxolan) 
• 646032-70-4 3-benzyloxy-14β-[(E)-(but-2-enyl)oxy]-17-cyclopropylmethyl-4,5α-epoxy-morphinane-6-spiro-2'-(1,3-dioxolan) 
• 1192542-96-3 17-cyclopropylmethyl-3-benzyloxy-14-carboxymethoxy-6-(1',3'-dioxolan-2'-yl)-4,5α-epoxymorphinan-N-oxide 
• 1192542-95-2 17-cyclopropylmethyl-3-benzyloxy-14-(2',3'-dihydroxypropyloxy)-6-(1',3'-dioxolan-2'-yl)-4,5α-epoxymorphinan 
• 1192542-97-4 C₃₃H₄₀N₂O₈S 
• 1192542-71-4 3-benzyIoxy-17-cyclopropylmethyl-6-(1',3'-dioxolan-2'yl)-14-propoxy-4,5α-epoxymorphinan 

Relevant academic research and scientific papers

Design, synthesis, and preliminary evaluation of a potential synthetic opioid rescue agent

Background: One of the most prominent opioid analgesics in the United States is the high potency agonist fentanyl. It is used in the treatment of acute and chronic pain and as an anesthetic adjuvant. When used inappropriately, however, ingestion of just a

Discovery of novel delta opioid receptor (Dor) inverse agonist and irreversible (non-competitive) antagonists

The delta opioid receptor (DOR) is a crucial receptor system that regulates pain, mood, anxiety, and similar mental states. DOR agonists, such as SNC80, and DOR-neutral antagonists, such as naltrindole, have been developed to investigate the DOR in vivo and as potential therapeutics for pain and depression. However, few inverse agonists and non-competitive/irreversible antagonists have been developed, and none are widely available. This leaves a gap in our pharmacological toolbox and limits our ability to investigate the biology of this receptor. Thus, we designed and synthesized the novel compounds SRI-9342 as an irreversible antagonist and SRI-45127/SRI-45128 as inverse agonists. Then, these compounds were evaluated in vitro for their binding affinity by radioligand binding and functional activity by35 S-GTPγS coupling and cAMP accumulation in cells expressing the human DOR. All three compounds demonstrated high binding affinity and selectivity at the DOR, and all three displayed their hypothesized molecular pharmacology of irreversible antagonism (SRI-9342) or inverse agonism (SRI-45127/SRI-45128). Together, these results demonstrate that we have designed new inverse agonists and irreversible antagonists of the DOR based on a novel chemical scaffold. These new compounds will provide new tools to investigate the biology of the DOR or even new potential therapeutics.

MORPHINAN DERIVATIVES OF ORGANIC AND INORGANIC ACIDS

Novel 4,5-epoxy-14-substituted morphinan derivatives of organic and inorganic acids are disclosed. Pharmaceutical compositions containing the compounds and methods of their pharmaceutical uses and syntheses are also disclosed. The compounds disclosed are useful, inter alia, as modulators of opioid receptors.

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.