American Cyanamid Company

Thomas C McKenzie

William J Fanshawe

Joseph William Epstein

Lantz S Crawley

John J Brown

This invention concerns 1-aryl-3-azabicyclo[3.2.0]heptanes and their acid-addition salts. More particularly, this invention pertains to compositions useful for treatment of depression in warm-blooded animals.

1-Aryl-3-azabicyclo[3.2.0]heptanes

This disclosure describes 3a-(substituted-phenyl)-2,3,3a,4,7,7a-hexahydro[or 3a-(substituted-phenyl) octahydro]-4,7-alkano-1H-isoindoles which possess activity as antidepressants and as antistress agents in mammals.

3a-(substituted phenyl)-2,3,3a,4,7,7a-hexahydro[or

Novel compounds are disclosed having the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each individually selected from the class consisting essentially of hydrogen, hydroxy, chloro, bromo, an alkyl radical having up to 3 carbon atoms, an alkoxy radical having up to 3 carbon atoms, and trifluoromethyl, and any two or more of R.sub.1, R.sub.2 and R.sub.3 may be the same; R.sub.4 is selected from the class consisting essentially of hydrogen, an alkyl radical having up to 3 carbon atoms, an allyl radical having up to 4 carbon atoms, the cyclopropylmethyl radical or the phenethyl radical; and W and W' each represent a monovalent alkyl moiety having up to 3 carbon atoms or W-W' jointly represent a divalent moiety of the formula ##STR2## where n is an integer of 2 or 3, including individual optically active isomers, racemic mixtures thereof, and non-toxic pharmacologically-acceptable acid-addition salts thereof. Such compounds are useful as analgesics in mammals. They can be prepared by irradiating with ultra-violet light a mixture of a dialkoxyethylene and a maleimide of the formula ##STR3## to produce a 4,4-dialkoxy-N-alkyl-1-phenyl-1,2-cyclobutanedicarboximide, and chemically reducing the same. Three other processes of preparation are also described.

5-Aryl-3-azabicyclo[3.2.0]heptan-6-one acetals, and analgesic use

Novel substituted 3-[2-(4-phenyl or pyridyl-1-piperazinyl or piperidino)ethyl]indolines useful as antipsychotic agents in mammals as well as substituted 3-[2-(4-phenylpiperidino)ethyl]indole intermediates for their preparation.

Cis-mono and disubstituted-2-methyl-3-[(piperazinyl) and

Unsubstituted, mono-, di- or trisubstituted-11-(1,2,3,6-tetrahydro-substituted-4-pyridyl)-dibenz[b,f][1 ,4]oxazepines, useful as anti-psychotic agents..

11-(1,2,3,6-Tetrahydro-substituted-4-pyridyl)-dibenz[b,f][1,4]oxazepines

Substituted Dibenz[b,f][1,4]oxazepin-11-yl pyridinium salts and derivatives thereof useful as intermediates in the preparation of anti-psychotic agents.

Growing community of inventors

Pearl River, NY, United States of America

Thomas C McKenzie