Novel compounds and their uses

Abstract

Use of a compound according to Formula [I]: or a salt thereof to produce a cooling sensation, wherein R 1 and R 2 are independently selected from hydrogen or halogen atoms; hydroxy, cyano, nitro, mercapto, carbonyl, sulfone and carboxy groups; or optionally substituted alkyl, alkenyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, amino, siloxy, ester and heterocyclic groups, with the proviso that when R 1 is 2-hydroxyphenyl, R 2 is other than 3-nitrophenyl.

1 . A method of imparting a cooling sensation to a human comprising administering to said human, a compound according to Formula [I]:  
     
       
         
         
             
             
         
       
     
     wherein R 1  and R 2  are independently selected from hydrogen or halogen atoms; hydroxy, cyano, nitro, mercapto, carbonyl, sulfone and carboxy groups; or optionally substituted alkyl, alkenyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, amino, siloxy, ester and heterocyclic groups, with the proviso that when R 1  is 2-hydroxyphenyl, R 2  is other than 3-nitrophenyl.  
   
   
       2 . The method of  claim 1 , wherein R 1  is an optionally substituted alkyl or aryl group.  
   
   
       3 . The method of  claim 2 , wherein R 1  is an optionally substituted aryl or cyclic hydrocarbon group.  
   
   
       4 . The method of  claim 1 , wherein R 2  is a hydrogen atom, or an optionally substituted alkyl or aryl.  
   
   
       5 . The method of  claim 4  wherein R 2  is an optionally substituted aryl or cyclic hydrocarbon group.  
   
   
       6 . The method of  claim 5  of a compound of formula [II]:  
     
       
         
         
             
             
         
       
     
     wherein the or each X and Y is independently a halogen atom or a alkyl, alkenyl, haloalkyl, alkoxy, hydroxy, thiol, carboxy, nitro, sulphonamide, sulphonato, sulphonyl, alkoxycarbonyl, carbonyl or amino group, and m and n are independently 0, 1, 2 or 3.  
   
   
       7 . The method of  claim 6 , wherein the or each X is independently a hydrogen or halogen atom, or a nitro, hydroxy, C 1-6  alkyl, C 1-6  haloalkyl or C 1-6  alkoxy group.  
   
   
       8 . The method of  claim 6 , wherein the or each Y is independently a hydroxy, C 1-6  alkyl or C 1-6  alkoxy group.  
   
   
       9 . The method of  claim 6 , wherein m is 1.  
   
   
       10 . The method of  claim 6 , wherein n is 1.  
   
   
       11 . The method of  claim 10 , wherein the compound has the formula [III]:  
     
       
         
         
             
             
         
       
     
     wherein the or each X and Y is independently a halogen atom or a alkyl, alkenyl, haloalkyl, alkoxy, hydroxy, thiol, carboxy, nitro, sulphonamide, sulphonato, sulphonyl, alkoxycarbonyl, carbonyl or amino group, and m and n are independently 0, 1, 2 or 3.  
   
   
       12 . A method of imparting a cooling sensation to a human, the method comprising administering to said human, a compound iselected from the group consisting of 1-(2′-methoxyphenyl)-4-(3″-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one, 1-phenyl-4-(3″-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one, 1-(2′-methoxyphenyl)-4-(3″-chlorophenyl)-1,2,3,6-tetrahydropyrimidine-2-one, 1-(2′-methylphenyl)-4-(3″-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one, 1-phenyl-4-(3″-chlorophenyl)-1,2,3,6-tetrahydropyrimidine-2-one, 1-(2′-methoxyphenyl-4-(3″-methoxyphenyl)-1,2,3,6-tetrahydropyrimidine-2-one 1-phenyl-4-(3″-methoxyphenyl)-1, 2,3,6-tetrahydropyrimidine-2-one 1-(2′-hydroxyphenyl)-4-(3″-methoxyphenyl)-1,2,3,6tetrahydropyrimidine-2-one, 1-(2′-trifluoromethylphenyl)-4-(3″-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one, 1-phenyl-4-(3″-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one or 1-(2′-hydroxyphenyl)-4-phenyl-1,2,3,6-tetrahydropyrimidine-2-one and mixtures thereof to produce a cooling sensation.  
   
   
       13 - 21 . (canceled)  
   
   
       22 . A toothpaste composition comprising a compound of formula [I]:  
     
       
         
         
             
             
         
       
     
     or a salt thereof to produce a cooling sensation, wherein R 1  and R 2  are independently selected from hydrogen or halogen atoms; hydroxy, cyano, nitro, mercapto, carbonyl, sulfone and carboxy groups; or optionally substituted alkyl, alkenyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, amino, siloxy, ester and heterocyclic groups.  
   
   
       23 . The toothpaste composition of  claim 22 , with the proviso that when R 1  is 2-hydroxyphenyl, R 2  is other than 3-nitrophenyl.  
   
   
       24 . (canceled)  
   
   
       25 . A mouthwash composition comprising a compound of formula [I]:  
     
       
         
         
             
             
         
       
     
     or a salt thereof to produce a cooling sensation, wherein R 1  and R 2  are independently selected from hydrogen or halogen atoms; hydroxy, cyano, nitro, mercapto, carbonyl, sulfone and carboxy groups; or optionally substituted alkyl, alkenyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, amino, siloxy, ester and heterocyclic groups.  
   
   
       26 . The mouthwash composition of  claim 25 , with the proviso that when R 1  is 2-hydroxyphenyl, R 2  is other than 3-nitrophenyl.  
   
   
       27 . (canceled)  
   
   
       28 . A food product composition comprising a compound of formula [I]:  
     
       
         
         
             
             
         
       
     
     or a salt thereof to produce a cooling sensation, wherein R 1  and R 2  are independently selected from hydrogen or halogen atoms; hydroxy, cyano, nitro, mercapto, carbonyl, sulfone and carboxy groups; or optionally substituted alkyl, alkenyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, amino, siloxy, ester and heterocyclic groups.  
   
   
       29 . The food product composition of  claim 28 , with the proviso that when R 1  is 2-hydroxyphenyl, R 2  is other than 3-nitrophenyl.  
   
   
       30 . The food product composition of  claim 28 , wherein the food product is a beverage.  
   
   
       31 . The food product composition of  claim 28 , wherein the food product is ice-cream.  
   
   
       32 . The food product composition of  claim 28 , wherein the food product is a spread.  
   
   
       33 . The food product composition of  claim 28 , wherein the food product is a confectionery product.