863513-93-3

Upstream product

• 65619-19-4 4-dimethylamino-4-phenylcyclohexanone, ethylene ketal hydrochloride 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 65619-20-7 4-dimethylamino-4-phenylcyclohexanone 
• 101349-12-6 2-(5-fluoro-1H-indol-3-yl)ethanol 

Downstream Products

• 863513-92-2 C₂₄H₂₇FN₂O*0.5C₆H₈O₇ 

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.

PROCESS FOR THE PREPARATION OF (1R,4R)-6'-FLUORO-(N,N-DIMETHYL- AND N-METHYL)-4-PHENYL-4',9'-DIHYDRO-3'H-SPIRO[CYCLOHEXANE-1,1'-PYRANO-[3,4,B]INDOL]-4-AMINE

The present invention relates to a process for the preparation of (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4b]indol]-4-amine and (1r,4r)-6'-fluoro-N-methyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4b]- indol]-4-amine or physiologically acceptable acid addition salts thereof.