N-alkylcarbonyl-amino acid ester and N-alkylcarbonyl-amino lactone compounds and their use

Abstract

The present invention generally relates to refreshing, soothing, and cooling compounds that affect sensory processes. More particularly, the present invention pertains to certain N-alkylcarbonyl-amino acid ester as described herein; compositions and articles comprising such compounds; and methods of treatment, for example, methods of increasing alertness, and decreasing fatigue or sleepiness, and alleviating ocular discomforts of irritation, itch, and pain.

1 . A towelette containing a compound of Formula (1): 
       
         
           
           
               
               
           
         
         wherein:
 R 1  is hydrogen, or a methyl group such that the carbon atom to which it is attached is in the  D -configuration, and 
 when R 1  is hydrogen, R 2  is isopropyl, and 
 when R 1  is a methyl group such that the carbon atom to which it is attached is in the  D -configuration, R 2  is a C 1  to C 3  alkyl group. 
 
       
     
     
         2 . A compound according to  claim 1 , which is (R)-2-[((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-propionic acid methyl ester. 
     
     
         3 . A compound according to  claim 1 , which is (R)-2-R(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-propionic acid ethyl ester. 
     
     
         4 . A compound according to  claim 1 , which is (R)-2-[((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-propionic acid isopropyl ester. 
     
     
         5 . A compound according to  claim 1 , which is (R)-2-[((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-acetic acid isopropyl ester. 
     
     
         6 . The towelette as in  claim 1  wherein the compound is present in the towelette at a liquid concentration of 0.2 to 2 mg/ml. 
     
     
         7 . A method of preparing a therapeutic article of manufacture, comprising:
 providing a towelette;   contacting the towelette with a compound of Formula (1):   
       
         
           
           
               
               
           
         
         wherein:
 R 1  is hydrogen, or a methyl group such that the carbon atom to which it is attached is in the  D -configuration, and 
 when R 1  is hydrogen, R 2  is isopropyl, and 
 when R 1  is a methyl group such that the carbon atom to which it is attached is in the  D -configuration, R 2  is a C 1  to C 3  alkyl group. 
 
       
     
     
         8 . Use of towelette according to  claim 7  to alleviate ocular skin irritation, itch, and/or pain, and/or to increase alertness and to reduce sleepiness and fatigue. 
     
     
         9 . A therapeutic method comprising:
 contacting a towelette carrying a compound of Formula (1):   
       
         
           
           
               
               
           
         
         wherein:
 R 1  is hydrogen, or a methyl group such that the carbon atom to which it is attached is in the  D -configuration, and 
 when R 1  is hydrogen, R 2  is isopropyl, and 
 when R 1  is a methyl group such that the carbon atom to which it is attached is in the  D -configuration, R 2  is a C 1  to C 3  alkyl group. 
 
         with the facial skin of a mammal, the contacting sufficient to deliver a therapeutically effective amount of the formula 1 compound. 
       
     
     
         10 . The method as in  claim 9  wherein the therapeutically effective amount is sufficient to alleviate ocular skin irritation, itch, and/or pain, and/or to increase alertness and to reduce sleepiness and fatigue.