Compounds for treatment of metabolic syndrome

Abstract

Present invention refers to new compounds of formula I or II, its synthesis and its use in the treatment of metabolic syndrome, particularly for the treatment of type I or type II diabetes and/or metabolic syndrome or metabolic disease or metabolic disorders.

1 - 41 . (canceled) 
     
     
         42 . A method of treating or reducing the symptoms related to a metabolic disease or disorder in a subject in need thereof, comprising administering to the subject in need of said treating or symptom reducing a composition comprising a compound of formula I, 
       
         
           
           
               
               
           
         
         wherein, independently, 
         R 1  can selected from: linear or cycled mono or dialkylamines; aminoalkylalcohols; or aminoalkylethers; 
         R 2  can be selected from: benzene or heterocycle rings; 
         R 3  can be selected from: H; a hydrocarbon radical selected from straight or branched alkyl of from 1 to 5 carbons; or benzyl group; 
         R 4  can be selected from: H; a hydrocarbon radical selected from straight or branched alkyl of from 1 to 5 carbons; hydroxy or alkoxy radicals; or halogen, 
         or any pharmaceutically, cosmetically, or food grade acceptable salts, and combinations thereof, 
         wherein the administration of said composition to the subject treats or reduces the symptoms related to the metabolic disease or disorder. 
       
     
     
         43 . The method of  claim 42 , wherein the metabolic disease or disorder is selected from the group consisting of hypertension, obesity, overweight, hyperlipidemia, diabetes, and hyperglycemia. 
     
     
         44 . The method of  claim 43 , wherein said diabetes is type I diabetes or type II diabetes. 
     
     
         45 . The method of  claim 43 , wherein said hyperlipidemia is hypercholesterolemia or hypertriglyceridemia. 
     
     
         46 . The method of  claim 42 , wherein, independently
 R 1  can be selected from: linear or cycled mono or dialkylamines; aminoalkylalcohols; or aminoalkylethers;   R 2  is selected from:   
       
         
           
           
               
               
           
         
         or a heterocycle ring which is 
       
       
         
           
           
               
               
           
         
         R 3  can be selected from: H; a hydrocarbon radical selected from straight or branched alkyl of from 1 to 5 carbons; or benzyl group; 
         R 4  can be selected from: H; a hydrocarbon radical selected from straight or branched alkyl of from 1 to 5 carbons; hydroxy or alkoxy radicals; or halogen. 
         wherein, 
         when R 1  is a linear mono or dialkylamine, it is selected from: NH—(CH 2 ) n —NH 2  wherein the value of n is 1, 2, 3 or 4; NH—CH 2 CH 2 —N(CH 3 ) 2 ; or NH—N═CH-phenyl-R 7 ; and 
         when R 1  is a cycled mono or dialkylamine, it is selected from: 
       
       
         
           
           
               
               
           
         
       
       and
 when R 1  is an aminoalkylalcohol, it is selected from HNCH 2 CH 2 OH; and 
 when R 1  is an aminoalkylether group, it is selected from HNCH 2 CH 2 OCH 3 ; and 
 R 5  can be selected from: H; alkoxy; halogen; hydroxy; or halogen-alkyl; 
 R 7  can be selected from: H or NO 2 ; and 
 R 8  can be selected from: H; hydroxy; or alkoxy; 
 when R 1  is NH—CH 2 CH 2 —N(CH 3 ) 2 , R 2  is 
 
       
         
           
           
               
               
           
         
       
       R 3 , R 4 , and R 8  are H, R 5  is OCH 3 , and said compound of general formula I is a hydrochloride salt;
 or any pharmaceutically, cosmetically, or food grade acceptable salts, and combinations thereof. 
 
     
     
         47 . The method of  claim 46 , wherein the compound is of formula III 
       
         
           
           
               
               
           
         
         wherein formula III is selected from (i) compound 4a, wherein R 1  is NH(CH 2 ) 2 NH 2  and R 5  is p-OCH 3 ; or from (ii) formula 5a compound, wherein R 1  is NH(CH 2 ) 3 NH 2  and R 5  1 S p-OCH 3 . 
       
     
     
         48 . The method of  claim 46 , wherein the compound selected from the group consisting of: 4a, 5a, 7a, 17a, 17b, 17c, 21a, 21b, 21c, 21d, 21e, 21f, 23a, 23b, 23c, 23d, 23e, 23f, 26a, and 26b, as follows: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         or any pharmaceutically, cosmetically, or food grade acceptable salts, and combinations thereof. 
       
     
     
         49 . The method of  claim 48 , wherein the compound is selected from the group consisting of: 4a, 5a, 7a, 17a, 17b, 17c, 26a, and 26b. 
     
     
         50 . The method of  claim 48 , wherein the compound is selected from the group consisting of: 21a, 21b, 21c, 21d, 21e, 21f, 23a, 23b, 23c, 23d, 23e, and 23f. 
     
     
         51 . The method of  claim 42 , wherein the composition is
 (i) a pharmaceutical composition comprising a compound of formula I, or any pharmaceutically acceptable salts thereof, or combinations thereof; and optionally, at least an inert compound, carrier, or excipient; or,   (ii) a cosmetic composition comprising a compound of formula I, or any cosmetically acceptable salts thereof, or combinations thereof; and optionally, at least an inert compound, carrier, or excipient; or,   (iii) a functional food additive composition comprising a compound of formula I, or any food grade acceptable salts thereof, or combinations thereof; and optionally, at least an inert compound, carrier, or excipient; or,   (iv) a nutraceutic composition comprising a compound of formula I, or any food grade acceptable salts thereof, or combinations thereof; and optionally, at least an inert compound, carrier, or excipient; or,   (v) a combination thereof.   
     
     
         52 . The method of  claim 42 , wherein the metabolic disease or disorder is diabetes and the composition is a pharmaceutical or nutraceutical composition comprising a compound of formula I, or any pharmaceutically acceptable salts thereof, or combinations thereof, and optionally, at least an inert compound, carrier, or excipient. 
     
     
         53 . The method of  claim 52 , wherein the compound of formula I is selected from the group consisting of: 4a, 5a, 7a, 17a, 17b, 17c, 21a, 21b, 21c, 21d, 21e, 21f, 23a, 23b, 23c, 23d, 23e, 23f, 26a, and 26b. 
     
     
         54 . The method of  claim 42 , wherein the metabolic disease or disorder is obesity or overweight and the composition is a pharmaceutical, cosmetic, or nutraceutical composition comprising a compound of formula I, or any pharmaceutically, cosmetically, or food grade acceptable salts thereof, or combinations thereof, and optionally, at least an inert compound, carrier, or excipient. 
     
     
         55 . The method of  claim 54 , wherein the compound of formula I is selected from the group consisting of: 4a, 5a, 7a, 17a, 17b, 17c, 21a, 21b, 21c, 21d, 21e, 21f, 23a, 23b, 23c, 23d, 23e, 23f, 26a, and 26b. 
     
     
         56 . The method of  claim 42 , wherein the metabolic disease or disorder is hypertension and the composition is a pharmaceutical or nutraceutical composition comprising a compound of formula I, or any pharmaceutically, cosmetically, or food grade acceptable salts thereof, or combinations thereof, and optionally, at least an inert compound, carrier, or excipient. 
     
     
         57 . The method of  claim 56 , wherein compound of formula I is selected from the group consisting of: 4a, 5a, 7a, 17a, 17b, 17c, 21a, 21b, 21c, 21d, 21e, 21f, 23a, 23b, 23c, 23d, 23e, 23f, 26a, and 26b. 
     
     
         58 . The method of  claim 42 , wherein the metabolic disease or disorder is hyperlipidemia and the composition is a pharmaceutical or nutraceutical composition comprising a compound of formula I, or any pharmaceutically, cosmetically, or food grade acceptable salts thereof, or combinations thereof, and optionally, at least an inert compound, carrier, or excipient. 
     
     
         59 . The method of  claim 58 , wherein the compound of formula I is selected from the group consisting of: 4a, 5a, 7a, 17a, 17b, 17c, 21a, 21b, 21c, 21d, 21e, 21f, 23a, 23b, 23c, 23d, 23e, 23f, 26a, and 26b. 
     
     
         60 . A pharmaceutical, cosmetic, functional food additive, or nutraceutical composition comprising at least a compound of formula I, 
       
         
           
           
               
               
           
         
         wherein, independently, 
         R 1  can selected from: linear or cycled mono or dialkylamines; aminoalkylalcohols; or aminoalkylethers; 
         and R 1  when being a cycled amine is 
       
       
         
           
           
               
               
           
         
         R 2  can be selected from: benzene or heterocycle rings; 
         R 3  can be selected from: H; a hydrocarbon radical selected from straight or branched alkyl of from 1 to 5 carbons; or benzyl group; 
         R 4  can be selected from: H; a hydrocarbon radical selected from straight or branched alkyl of from 1 to 5 carbons; hydroxy or alkoxy radicals; or halogen, 
         or any pharmaceutically, cosmetically, or food grade acceptable salts thereof, or combinations thereof; and 
         optionally, at least an inert compound, carrier, or excipient. 
       
     
     
         61 . The method of  claim 52 , wherein the compound of formula I is selected from the group consisting of: 4a, 5a, and 7a.