Novel sulphur containing lipids for use as food supplement or as medicament

Abstract

The present disclosure relates to lipid compounds of general formula (I) wherein R 1 is chosen from a C 10 -C 22 alkyl group, a C 10 -C 22 alkenyl group having 1-6 double bonds, and a C 10 -C 22 alkynyl group having 1-6 triple bonds; R 2 and R 3 are the same or different and may be selected from different substituents; Y is chosen from sulphur, sulfoxide, and sulfone; and X is a carboxylic acid or a derivative thereof, a carboxylic ester, a carboxylic anhydride, or a carboxamide; or a pharmaceutically acceptable salt, complex, or solvate thereof. The present disclosure also relates to pharmaceutical compositions and lipid compositions comprising such compounds, and methods of using such compounds such as for treating diseases related to cardiovascular, metabolic, and/or inflammatory diseases.

1 - 86 . (canceled) 
     
     
         87 . A method for the treatment of a disease or condition chosen from a dyslipidemic condition; elevated triglyceride levels, LDL cholesterol levels, and/or VLDL cholesterol levels; peripheral insulin resistance; and/or a diabetic condition in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of 
       
         
           
           
               
               
           
         
         2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenylthio)butanoic acid. 
       
     
     
         88 . The method according to  claim 87 , wherein the dyslipidemic condition is hypertriglyceridemia (HTG). 
     
     
         89 . The method according to  claim 87 , where the diabetic condition is type 2 diabetes. 
     
     
         90 . A method for the reduction of at least one of plasma insulin, blood glucose, or serum triglycerides in a subject in need thereof, comprising administering to the subject a pharmaceutically active amount of 
       
         
           
           
               
               
           
         
         2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenylthio)butanoic acid. 
       
     
     
         91 . A method for the treatment of atherosclerosis in a subject in need thereof, comprising administering to the subject a pharmaceutically effective amount of a compound of formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is chosen from a C 10 -C 22  alkenyl group having 3-6 methylene interrupted double bonds in Z configuration and a C 10 -C 22  alkynyl group having 1-6 triple bonds; 
         R 2  and R 3  are the same or different and each are independently chosen from a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, or an alkylamino group, provided that R 2  and R 3  are not both a hydrogen atom; or 
         R 2  and R 3  are connected in order to form a cycloalkane; 
         Y is chosen from sulphur, sulfoxide, and sulfone; and 
         X is a carboxylic acid or a derivative thereof, wherein the derivative is a carboxylic ester, a carboxamide, a monoglyceride, a diglyceride, a triglyceride, or a phospholipid; 
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         92 . The method of  claim 91 , wherein the compound of formula (I) is 
       
         
           
           
               
               
           
         
         2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenylthio)butanoic acid. 
       
     
     
         93 . A method for the treatment myocardial infarction and/or an inflammatory disease or condition in a subject in need thereof, comprising administering to the subject a pharmaceutically effective amount of a compound of formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is chosen from a C 10 -C 22  alkenyl group having 3-6 methylene interrupted double bonds in Z configuration and a C 10 -C 22  alkynyl group having 1-6 triple bonds; 
         R 2  and R 3  are the same or different and each are independently chosen from a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, or an alkylamino group, provided that R 2  and R 3  are not both a hydrogen atom; or 
         R 2  and R 3  are connected in order to form a cycloalkane; 
         Y is chosen from sulphur, sulfoxide, and sulfone; and 
         X is a carboxylic acid or a derivative thereof, wherein the derivative is a carboxylic ester, a carboxamide, a monoglyceride, a diglyceride, a triglyceride, or a phospholipid; 
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         94 . The method according to  claim 93 , for the treatment of myocardial infarction. 
     
     
         95 . The method according to  claim 93 , for the treatment of an inflammatory disease or condition. 
     
     
         96 . The method of  claim 94 , wherein the compound of formula (I) is 
       
         
           
           
               
               
           
         
         2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenylthio)butanoic acid. 
       
     
     
         97 . The method of  claim 95 , wherein the compound of formula (I) is 
       
         
           
           
               
               
           
         
         2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenylthio)butanoic acid. 
       
     
     
         98 . A pharmaceutical composition comprising the lipid compound 
       
         
           
           
               
               
           
         
         2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenylthio)butanoic acid.