66504-40-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane is used as a potential candidate for drug development in the pharmaceutical industry. Its unique structure and potential biological activities make it a promising candidate for the development of new drugs.
Used in Medicinal Chemistry Research:
1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane is used as a subject of study in medicinal chemistry research. Its potential pharmacological properties and unique structure make it an interesting compound for researchers to explore its potential use in various therapeutic applications.

Upstream product

• 67644-29-5 1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexane 
• 66504-42-5 (1R,2S)-1-(3,4-Dichloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 66504-43-6 (1R,2S)-1-(3,4-Dichloro-phenyl)-cyclopropane-1,2-dicarboxylic acid 
• 6725-45-7 ethyl 3,4-dichlorophenylacetate 
• 66504-44-7 (±)-1-(3,4 dichlorophenyl)-3-azabicyclo[3.1.0]-hexane-2,4-dione 
• 41204-08-4 ethyl α-bromo-3,4-dichlorophenylacetate 

Relevant academic research and scientific papers

Use of 1-(substitutedphenyl)-3-azabicyclo[3.1.0]hexanes for the treatment of chemical dependencies

The invention is a method of treatment for the relief of an addictive, compulsive disorder which comprises the administration to a human or animal suffering from such a disorder an effective amount of the compound of the formula: wherein R is hydrogen, alkyl (C1-C6); R1is hydrogen, mono or disubstituted halogen, alkoxy (C1-C3), CF3, alkyl (C1-C6); and R2is hydrogen, methyl or ethyl, or a pharmaceutically acceptable salt thereof.

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.

Azabicyclohexanes

Substituted 3-azabicyclo[3.1.0]hexanes, acid addition salts, method of use and method of preparation are described. The compounds have anxiolytic and analgesic activity.