65619-19-4

Upstream product

• 4746-97-8 cyclohexanedione monoethylene ketal 
• 65619-92-3 8-(dimethylamino)-1,4-dioxaspiro-[4.5]-decane-8-carbonitrile 
• 100-59-4 phenylmagnesium chloride 

Downstream Products

• 65619-20-7 4-dimethylamino-4-phenylcyclohexanone 
• 863513-91-1 (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine 
• 863513-93-3 (1s,4s)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine 
• 691880-04-3 cis-4',9'-dihydro-N,N-dimethyl-4-phenyl-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indol]-4-amine 
• 1357001-58-1 2',3',4',9'-tetrahydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1'-pyrido[3,4-b]indol]-4-amine 
• 1357001-57-0 2',3',4',9'-tetrahydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1'-pyrido[3,4-b]indol]-4-amine 
• 1357001-76-3 cis-(E)-2',3',4',9'-tetrahydro-N,N-dimethyl-6'-fluoro-4-phenyl-2'-(2-phenylvinyl)carbonylspiro[cyclohexane-1,1'(1'H)-pyrido[3,4-b]indole]-4-amine 
• 1357001-66-1 cis-(E)-2',3',4',9'-tetrahydro-N,N-dimethyl-4-phenyl-2'-(2-phenylvinyl)carbonylspiro[cyclohexane-1,1'(1'H)-pyrido[3,4-b]indole]-4-amine methanesulfonate 
• 1357001-62-7 cis-6'-fluoro-2',3',4',9'-tetrahydro-N,N-dimethyl-4-(phenyl)spiro[cyclohexane-1,1'(1'H)-pyrido[3,4-b]indole]-4-amine 

Relevant academic research and scientific papers

Discovery of a potent analgesic NOP and opioid receptor agonist: Cebranopadol

In a previous communication, our efforts leading from 1 to the identification of spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amine 2a as analgesic NOP and opioid receptor agonist were disclosed and their favorable in vitro and in vivo pharmacological properties revealed. We herein report our efforts to further optimize lead 2a, toward trans-6′-fluoro-4′, 9′-dihydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1′(3′H) -pyrano[3,4-b]indol]-4-amine (cebranopadol, 3a), which is currently in clinical development for the treatment of severe chronic nociceptive and neuropathic pain.

Spirocyclic Azaindole Derivatives

The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.

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.