863513-92-2

Basic information

• Product Name: Cebranopadol hemicitrate
• Synonyms: Cebranopadol hemicitrate;(1alpha,4beta)-6'-Fluoro-4',9'-dihydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1'(3'H)-pyrano[3,4-b]indol]-4-amine 2-hydroxy-1,2,3-propanetricarboxylate (2:1);Difelikefalin
• CAS NO: 863513-92-2
• Molecular Formula: C54H62F2N4O9
• Molecular Weight: 949.0882864
• EINECS: -0
• Mol File: 863513-92-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cebranopadol hemicitrate(CAS DataBase Reference)
• NIST Chemistry Reference: Cebranopadol hemicitrate(863513-92-2)
• EPA Substance Registry System: Cebranopadol hemicitrate(863513-92-2)

Safety Data

• Hazardous Substances Data: 863513-92-2(Hazardous Substances Data)

Upstream product

• 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 
• 77-92-9 citric acid 
• 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 

Relevant articles and documents

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.

SPIROCYCLIC CYCLOHEXANE DERIVATIVES

The invention relates to spirocyclic cyclohexane derivatives, to a method for the production thereof, to medicaments containing said compounds and to the utilization of spirocyclic cyclohexane derivatives for the production of medicaments.