Pyrrolidine carboxamido derivatives and methods for preparing and using the same

Abstract

Pyrrolidine carboxamido derivatives, optical isomers thereof, and salts thereof that are able to prevent, improve, and/or treat inflammatory conditions, including inflammatory bowel disease, and methods for preparing and using the same are provided.

1 - 26 . (canceled) 
     
     
         27 . A compound of the following Formula: 
       
         
           
           
               
               
           
         
         an optical isomer thereof, or a pharmaceutically acceptable salt thereof. 
       
     
     
         28 . A pharmaceutical composition comprising the compound, the optical isomer, or the salt of claim  1 , and a pharmaceutically acceptable carrier. 
     
     
         29 . The pharmaceutical composition of  claim 28 , which is a formulation for oral administration. 
     
     
         30 . A method for preparing a compound of Formula 1, an optical isomer thereof, or a pharmaceutically acceptable salt thereof, which comprises:
 reacting a compound 2 with a compound 3 to prepare a compound 4;   hydrolyzing the compound 4 in the presence of a base to prepare a compound 5;   reacting the compound 5 with a compound 6 to prepare a compound 7;   hydrolyzing the compound 7 in the presence of a base to prepare a compound 8;   reacting the compound 8 with a compound 9 to prepare a compound 10;   hydrolyzing the compound 10 in the presence of a base to prepare the compound of Formula 1:   
       
         
           
           
               
               
           
         
         wherein 
         n is 0, 1, or 2; 
         A is -a 1 -, which is an amino acid independently selected from the group consisting of alanine, (Ala, A), arginine (Arg, R), asparagine (Asn, N), aspartic acid (Asp, D), cysteine (Cys, C), glutamic acid (Glu, E), glutamine (Gln, Q), glycine (Gly, G), histidine (His, H), isoleucine (Ile, I), leucine (Leu, L), lysine (Lys, K), methionine (Met, M), phenylalanine (Phe, F), proline (Pro, P), serine (Ser, S), threonine (Thr, T), tryptophan (Trp, W), tyrosine (Tyr, Y), and valine (Val, V), both terminal ends of the amino acid being coupled to a carbonyl group or an amine group by an amide bond; and 
         R 1  is a straight chain or branched chain C 1-36  alkyl, a straight chain or branched chain C 2-36  alkenyl including at least one double bond, or a straight chain or branched chain C 2-36  alkynyl including at least one triple bond. 
       
     
     
         31 . The method of  claim 30 , wherein
 n is 0, 1, or 2;   a 1  is   
       
         
           
           
               
               
           
         
          both terminal ends of which is coupled to a carbonyl group or amide group thereof by an amide bond; and 
         R 1  is a straight chain or branched chain C 1-36  alkyl.