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Journal of Medicinal Chemistry | 1982

Additions and Corrections- 1-Aryl-3-azabicyclo-[3.1.0]hexanes, a New Series of Nonnarcotic Analgesic Agents

Joseph W. Epstein; Herbert J. Brabander; William J. Fanshawe; Corris M. Hofmann; Thomas C. McKenzie; Sidney R. Safir; Arnold C. Osterberg; D. B. Cosulich; F. M. Lovell

A series of 1-aryl-3-azabicyclo[3.1.0]hexanes 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 intermediate 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-azabicyclo[3.1.0]hexane (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.


Journal of Medicinal Chemistry | 1981

1-Aryl-3-azabicyclo[3.1.0]hexanes, a new series of nonnarcotic analgesic agents

Joseph W. Epstein; Herbert J. Brabander; William J. Fanshawe; Corris M. Hofmann; Thomas C. McKenzie; Arnold C. Osterberg; Cosulich Db; Lovell Fm


Journal of Organic Chemistry | 1979

Thiophene systems. 2. Synthesis and chemistry of some 4-alkoxy-3-substituted thiophene derivatives

Jeffery B. Press; Corris M. Hofmann; Sidney R. Safir


Journal of Medicinal Chemistry | 1979

10-(Alkylamino)-4H-thieno[3,4-b][1,5]benzodiazepines. A novel class of potential neuroleptic agents.

Jeffery B. Press; Corris M. Hofmann; Eudy Nh; Fanshawe Wj; Day Ip; Greenblatt En


Archive | 1978

1-Phenyl-3-azabicyclo[3.1.0]hexanes

William J. Fanshawe; Joseph W. Epstein; Lantz S. Crawley; Corris M. Hofmann; Sidney R. Safir


Journal of Medicinal Chemistry | 1981

Thiophene systems. 5. Thieno[3,4-b][1,5]benzoxazepines, thieno[3,4-b][1,5]benzothiazepines, and thieno[3,4-b][1,4]benzodiazepines as potential central nervous system agents

Jeffery B. Press; Corris M. Hofmann; Eudy Nh; Day Ip; Greenblatt En


Archive | 1978

Azabicyclohexanes, method of use and preparation of the same

William J. Fanshawe; Joseph W. Epstein; Lantz S. Crawley; Corris M. Hofmann; Sidney R. Safir


ChemInform | 1981

1‐ARYL‐3‐AZABICYCLO(3.1.0)HEXANES, A NEW SERIES OF NONNARCOTIC ANALGESIC AGENTS

Joseph W. Epstein; Herbert J. Brabander; William J. Fanshawe; Corris M. Hofmann; Thomas C. McKenzie; Sidney R. Safir; Arnold C. Osterberg; D. B. Cosulich; F. M. Lovell


ChemInform | 1981

THIOPHENE SYSTEMS. 5. THIENO(3,4-B)(1,5)BENZOXAZEPINES, THIENO(3,4-B)(1,5)BENZOTHIAZEPINES, AND THIENO(3,4-B)(1,4)BENZODIAZEPINES AS POTENTIAL CENTRAL NERVOUS SYSTEM AGENTS

Jeffery B. Press; Corris M. Hofmann; N. H. Eudy; I. P. Day; E. N. Greenblatt; Sidney R. Safir


Archive | 1975

Para-fluorophenyl-N-heterocyclic substituted butanes

Corris M. Hofmann; Sidney R. Safir

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