Medicinal composition

Abstract

The present invention relates to an ameliorant for improving the movement of the digestive tract comprising, as an active ingredient, 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-2-hydroxymethyl-4-pyrrolidinyl]benzamide or an acid addition salt thereof which is a metabolite of 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-1-ethyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide or an acid addition salt thereof, having high biding affinity for a serotonin receptor 4 (5HT 4 ) and causing no arteritis and thrombus formation; a medicinal composition for improving the movement of the digestive tract comprising the said ameliorant and a pharmaceutically acceptable carrier; and a treating method for promoting the movement of the digestive tract, which comprises using the said medicinal composition for improving the movement of the digestive tract.

1 . (canceled) 
   
   
       2 . A medicinal composition for improving the movement of the digestive tract, comprising as an active ingredient 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-2-hydroxymethyl-4-pyrrolidinyl]benzamide or an acid addition salt thereof which has high binding affinity for a serotonin receptor 4 (5HT 4 ) and does not cause arteritis and thrombus formation, and a pharmaceutically acceptable carrier. 
   
   
       3 - 4 . (canceled) 
   
   
       5 . 4-Amino-5-chloro-2-methoxy-N-[(2S,4S)-2-hydroxymethyl-4-pyrrolidinyl]benzamide or an acid addition salt thereof. 
   
   
       6 . 4-Amino-5-chloro-2-methoxy-N-[(2S,4S)-2-hydroxymethyl-4-pyrrolidinyl]benzamide in which an amino group at position 4 or/and an amino group of the pyrrolidinyl group is optionally protected, or an acid addition salt thereof. 
   
   
       7 . A process for preparing 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-2-hydroxymethyl-4-pyrrolidinyl]benzamide or an acid addition salt thereof, which comprises reacting 4-amino-5-chloro-2-methoxybenzoic acid having an optionally protected amino group, or a reactive derivative thereof with (2S,4S)-4-amino-N-acyl-2-hydroxymethylpyrrolidine to obtain 4-amino-5-chloro-2-methoxy-N-[(2S,4S)-1-acyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide or an acid addition salt thereof, and eliminating a protecting group and the acyl group, when a protecting group is used in the acyl group. 
   
   
       8 . (2S,4S)-4-amino-N-acyl-2-hydroxymethylpyrrolidine having an optionally protected amino group. 
   
   
       9 . The compound according to  claim 8 , wherein a protecting group for an amino group is an acyl group, and the said acyl group and an acyl group of N-acyl are selected from formyl, acetyl, propionyl and benzoyl. 
   
   
       10 . The compound according to  claim 8 , wherein the acyl group is acetyl.