65618-76-0

Upstream product

• 65618-73-7 4-(p-fluorophenyl)-4-methylaminocyclohexanone, ethylene ketal 
• 65618-72-6 4-(p-fluorophenyl)-4-isocyanatocyclohexanone, ethylene ketal 
• 56327-03-8 8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid 

Downstream Products

• 1357001-64-9 trans-2',3',4',9'-tetrahydro-N,N-dimethyl-4-(4-fluorophenyl)-spiro[cyclohexane-1,1'(1'H)-pyrido[3,4-b]indole]-4-amine 
• 1357001-63-8 cis-2',3',4',9'-tetrahydro-N,N-dimethyl-4-(4-fluorophenyl)spiro[cyclohexane-1,1'(1'H)-pyrido[3,4-b]indole]-4-amine 
• 1357001-78-5 cis-(E)-2',3',4',9'-tetrahydro-N,N-dimethyl-4-(4-fluorophenyl)-2'-(2-phenylvinyl)carbonylspiro[cyclohexane-1,1'(1'H)-pyrido[3,4-b]indole]-4-amine 

Relevant academic research and scientific papers

Cis-tetrahydro-spiro(cyclohexane-1,1'-pyrido[3,4-b]indole)-4-amine Compounds

Cis-tetrahydro-spiro(cyclohexane-1,1′-pyrido[3,4-b]indole)-4-amine compounds which act on the nociceptin/ORL-1 receptor system as well as on the μ-opioid receptor system and which are distinguished in particular by selective effectiveness in the treatment of chronic pain, such as inflammatory pain, visceral pain, tumour pain, and neuropathic pain, without at the same time developing pronounced effectiveness against acute, nociceptive pain.

4-Amino-4-arylcyclohexanones and Their Derivatives, a Novel Class of Analgesics. 1. Modification of the Aryl Ring

Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues.Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated.Synthesis starts by double Michael reaction of acrylate on arylacetonitriles.Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3.Isocyanates were then converted to the title compounds.Analgesic activity is very sensitive to the nature and position of the substituent on the aromatic ring.The most potent compounds in this series (p-CH3, p-Br) showed 50percent the potency of morphine.Deletion of the ring oxygen abolishes activity.