Benzamide derivatives

Abstract

Disclosed are benzamide derivatives useful in slowing the expansion of cancer cells.

We claim: 
     
         1 . A compound of formula: 
       
         
           
           
               
               
           
         
         wherein X is selected from the group consisting of H, halo, —C 1 -C 6  alkyl, aryl, —C 3 -C 7  cycloalkyl, and -3- to 10-membered heterocycle; 
         wherein Y is selected from the group consisting of H, —C 1 -C 6  alkyl, and —C 3 -C 7  cycloalkyl; 
         wherein Z is selected from the group consisting of methyl, —NH2, —NHOH, and phenylene diamine group (II) of structure 
       
       
         
           
           
               
               
           
         
         and wherein Q is selected from the group consisting of H, F and Cl; 
         and all pharmaceutically acceptable salts, solvates, and chemically protected forms thereof. 
       
     
     
         2 . The compound of  claim 1  wherein the compound is selected from the group consisting of:
 N-(2-aminophenyl)-4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzamide, N-hydroxy-4-(1-methyl-1H-benzo[d]imidazol-2-ylamino)benzamide, 4-(1-cyclobutyl-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, N-hydroxy-4-(1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzamide, 4-(1-cyclopentyl-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, 4-(5-bromo-1-isopropyl-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, 4-(6-bromo-1-isopropyl-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, N-hydroxy-4-(1-(2-methoxyethyl)-5-phenyl-1H-benzo[d]imidazol-2-ylamino)benzamide, N-hydroxy-4-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-ylamino)benzamide, 4-(5-bromo-1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, N-hydroxy-4-(1-(2-hydroxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzamide, 4-(5-fluoro-1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, N-hydroxy-4-(1-(2-isopropoxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzamide, 4-(5-(3-fluorophenyl)-1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, N-hydroxy-4-(1-(2-methoxyethyl)-5-(pyrimidin-5-yl)-1H-benzo[d]imidazol-2-ylamino)benzamide, 4-(5-cyclopropyl-1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, 4-(5-bromo-1-(2-(dimethylamino)ethyl)-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, N-hydroxy-4-(1-isopropyl-5-(pyrimidin-5-yl)-1H-benzo[d]imidazol-2-ylamino)benzamide, N-hydroxy-4-(1-isopropyl-5-(pyridin-3-yl)-1H-benzo[d]imidazol-2-ylamino)benzamide, N-(2-aminophenyl)-4-(1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)benzamide, 4-(6-fluoro-1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, 4-(4-fluoro-1-(2-methoxyethyl)-1H-benzo[d]imidazol-2-ylamino)-N-hydroxybenzamide, and N-hydroxy-4-(1-isopropyl-5-(methoxymethyl)-1H-benzo[d]imidazol-2-ylamino)benzamide. 
 
     
     
         3 . A method of synthesizing a pharmaceutical compound comprising: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The method of  claim 3  wherein compound 1 is 1-fluoro-2-nitrobenzene. 
     
     
         5 . The method of  claim 3  wherein compound 1 is 4-bromo-1-fluoro-2-nitrobenzene. 
     
     
         6 . The method of  claim 3  wherein compound 1 is 2,4-difluoro-1-nitrobenzene. 
     
     
         7 . The method of  claim 3  wherein compound 1 is 1,3-difluoro-2-nitrobenzene. 
     
     
         8 . The method of  claim 3  wherein compound 1 is 1-fluoro-4-(methoxymethyl)-2-nitrobenzene. 
     
     
         9 . The method of  claim 3  wherein compound 8 is 4-bromo-1-fluoro-2-nitrobenzene. 
     
     
         10 . The method of  claim 3  wherein compound 8 is 4-bromo-2-fluoro-1-nitrobenzene. 
     
     
         11 . The method of  claim 4  wherein compound 9 is 2-methoxyethaneamine. 
     
     
         12 . The method of  claim 4  wherein compound 9 is methylamine. 
     
     
         13 . The method of  claim 4  wherein compound 9 is cyclobutylamine. 
     
     
         14 . The method of  claim 4  wherein compound 9 is cyclopentylamine. 
     
     
         15 . The method of  claim 4  wherein compound 9 is 3-methoxypropan-1-amine. 
     
     
         16 . The method of  claim 4  wherein compound 9 is 2-aminoethanol. 
     
     
         17 . The method of  claim 4  wherein compound 9 is 2-isopropoxyethanamine. 
     
     
         18 . The method of  claim 4  wherein compound 9 is N1,N1-dimethylethane-1,2-diamine. 
     
     
         19 . The method of  claim 5  wherein compound 9 is isopropylamine. 
     
     
         20 . The method of  claim 5  wherein compound 9 is 2-methoxyethaneamine. 
     
     
         21 . The method of  claim 9  wherein compound 10 is benzeneboronic acid. 
     
     
         22 . The method of  claim 9  wherein compound 10 is 5-pyrimidineboronic acid. 
     
     
         23 . The method of  claim 9  wherein compound 10 is cyclopropylboronic acid. 
     
     
         24 . The method of  claim 9  wherein compound 10 is 3-pyridineboronic acid.