65619-67-2

Upstream product

• 73324-17-1 8-(4-tert-Butyl-phenyl)-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid 
• 73312-14-8 5-(4-tert-Butyl-phenyl)-5-cyano-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 73312-17-1 8-(4-tert-Butyl-phenyl)-1,4-dioxa-spiro[4.5]decane-8-carbonitrile 
• 73312-16-0 1-(4-tert-Butyl-phenyl)-4-oxo-cyclohexanecarbonitrile 
• 65619-66-1 4-p-t-butylphenyl-4-isocyanatocyclohexanone ethylene ketal 

Downstream Products

• 65619-69-4 4-(p-t-butylphenyl)-4-dimethylaminocyclohexanone 
• 65619-68-3 4-(p-t-butylphenyl)-4-dimethylaminocyclohexanone ethylene ketal 

Relevant academic research and scientific papers

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.

4-Amino-4-phenylcyclohexanone ketal compositions and process of use

A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.