A. H. Robins Company, Incorporated

Charles A Leonard

Albert D Cale, Jr

John Wesley Ward

Bernard V Franko

A method of counteracting the effects of histamine with aromatic azepinones and diazepinones and thiones thereof having the formula ##STR1## wherein: A is benzene, naphthalene, quinoline or pyridine;

Fused aromatic oxazepinones, thiazepinones, diazepinones and sulfur

The resolution of racemic 4-amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide into the optically active (+) and (-) isomers is disclosed.

Optical isomers of

N-(1-Substituted-3-pyrrolidinyl)benzamides of the formula ##STR1## wherein R is cycloalkyl or phenyllower-alkyl; R.sup.1 is hydrogen or lower alkyl of 1 to 8 carbon atoms; R.sup.2 is acetamido, amino, methylamino, dimethylamino, benzyloxy, halogen, lower alkoxy, methylmercapto, nitro, cyano, hydroxy, sulfamoyl, bis(methylsulfonyl)amino, methylsulfonylamino, aminomethyl or acetylaminomethyl and can be the same or different; n is an integer from one to three inclusive with the proviso that when R.sup.2 is amino, nitro, halogen or lower alkoxy, n is greater than one, and pharmaceutically acceptable acid addition salts thereof are disclosed.

N-(1-Substituted-3-pyrrolidinyl)benzamides

1,4-(3-)Disubstituted piperidines are disclosed which have useful antiemetic properties. The compounds have the general formula: ##STR1## wherein R is halogen, R.sup.1 is hydrogen and halogen, n is a positive integer from 2-4 and A is --C(O)-- and --CHOH--. The pharmaceutically acceptable acid addition salts of the basic compounds are particularly useful as antiemetics.

Method for inhibiting emesis and compositions therefor

A method is disclosed for controlling emesis utilizing N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides of the formula: ##SPC1## Wherein R is cycloalkyl, phenyl and phenyllower-alkyl; R.sup.1 is hydrogen, lower alkyl of 1 to 8 carbon atoms and phenyl; R.sup.2 is halogen, lower-alkyl, lower-alkoxy, amino, nitro, monoalkylamino, dialkylamino, mercaptomethyl, acetamido, sulfamoyl, cyano, hydroxy, benzyloxy, and trifluoromethyl; X is oxygen and sulfur; n is an integer from zero to three inclusive and pharmaceutically acceptable acid addition salts thereof. The benzamide compounds wherein R is cyclohexyl and R.sup.1 is lower-alkyl are particularly effective as antiemetics and have minimal side effects.

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Richmond, VA, United States of America

Charles A Leonard