Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides

• US 3,963,745 A
• Filed: 10/25/1974
• Issued: 06/15/1976
• Est. Priority Date: 04/03/1972
• Status: Expired due to Term

• Current Assignee: A.H. Robins Co., Inc. (Pfizer Inc.)
• Original Assignee: A. H. Robins Company, Incorporated
• Inventors: Cale, Albert Duncan Jr., Leonard, Charles Arthur
• Primary Examiner(s): Moyer, Donald B.
• Application Number:
  US05/518,124
• Time in Patent Office: 599 Days
• Field of Search: 260/326.83, 260/326.55, 260/326.47, 424/274
• US Class Current: 548/557
• CPC Class Codes: C07D 207/14 Nitrogen atoms not forming part of a nitro radical

Abstract

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; R¹ is hydrogen, lower alkyl of 1 to 8 carbon atoms and phenyl; R² 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 R¹ is lower-alkyl are particularly effective as antiemetics and have minimal side effects.

Claims

1. A compound of the formula:

##SPC6##

wherein;

R is cycloalkyl of four to 12 carbon atoms,

R¹ is hydrogen and lower alkyl of 1-8 carbon atoms,

R² is nitro, amino, halogen, sulfamoyl, methoxy and ethoxy,

n is an integer from zero to three inclusive, and the pharmaceutically acceptable acid addition salts thereof.

2. The compound of claim 1 which is 4-amino-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylthiobenzamide.

3. The compound of claim 1 which is 4-nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylthiobenzamide.