- Use of 1-(substitutedphenyl)-3-azabicyclo[3.1.0]hexanes for the treatment of chemical dependencies
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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.
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- Method of treating depression using azabicyclohexanes
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The present invention concerns certain novel substituted 3-azabicyclo[3.1.0]hexanes and a method of treating depression and stress in a warm-blooded animal, comprising the administration of substituted 3-azabicyclo[3.1.0]hexanes.
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- 1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents
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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.
- Epstein, Joseph W.,Brabander, Herbert J.,Fanshawe, William J.,Hofmann, Corris M.,McKenzie, Thomas C.,et al.
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p. 481 - 490
(2007/10/02)
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- Azabicyclohexanes
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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.
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- Acylazabicyclohexanes
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Phenyl and substituted phenyl 3-azabicyclo[3.1.0]-hexanes and method of preparing the same are described. They are useful as intermediates in preparing other physiologically active compounds.
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