Benzothiazole-and benzoxazole-4, 7-dione derivatives and their use as dcd25 phosphatase inhibitors
View Patent ↗The invention concerns the use as cdc25 phosphatase inhibitors, in particular cdc25-C phosphatase, and CD45 phosphatase, of compounds of general formula (I), wherein: W represents O or S. In accordance with the invention, the compounds of general formula (I) can in particular be used for preparing a medicine for cancer treatment
1. A method of treating human prostate cancer or human pancreas cancer in a warm-blooded animal comprising administering to a warm-blooded animal in need thereof an inhibiting amount of a compound of the formula
wherein
R 1 is —(CH 2 )—Z—NR 5 R 6 ,
Z is a bond or alkylene of 1 to 5 carbon atoms,
R 5 is hydrogen, alkyl, aralkyl, —(CH 2 ) n —OH, wherein
n is an integer of 1 to 6 , alkoxycarbonyl, haloalkylcarbonyl or aralkoxycarbonyl, and
R 6 is hydrogen, alkyl, aralkyl or —(CH 2 ) n —HO,
R 2 is hydrogen, alkyl or aralkyl;
R 3 is hydrogen, alkyl, haloalkyl, alkoxy or alkylthio;
R 4 is alkyl, cycloalkyl, cycloalkylalkyl, cyano or amino,
W is S;
or a pharmaceutically acceptable salt thereof.
2. The method of claim 1 wherein:
R 2 is hydrogen, methyl, ethyl, or benzyl
R 3 is hydrogen, alkyl, alkoxy, or alkylthio;
R 4 is alkyl or a carbocyclic.
3. A method of treating human prostate cancer or human pancreas cancer in a warm-blooded animal comprising administering to a warm-blooded animal in need thereof an inhibiting amount of:
-5 {[2-(dimethylamino)ethyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-5 {[6-(dimethylamino)hexyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-5[(1-ethylhexyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione;
-2-methyl-5-(propylamino)-1,3-benzothiazole-4,7-dione;
-5-[(2-methoxyethyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione;
-5-{[2-(diisopropylamino)ethyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-5-{[3-(dimethylamino)propyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-5-{[4-(dimethylamino)butyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-5-{[5-(dimethylamino)pentyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-5-{benzy[2-(dimethylamino)ethyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-2-methyl-5-{[3-(methylamino)propyl]amino}-1,3-benzothiazole-4,7-dione;
-5-[(3-aminopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione;
-6-(butylthio)-5-{[2-(dimethylamino)ethyl]amino}-2-methyl-1,3-benzothiazole-4,7-dione;
-2-cyciohexyl-5-[(2-pyrrolidin-1-ylethyl)amino]-1,3-benzothiazole-4,7-dione;
-2-cyclohexyl-6-[(2-pyrrolidin-1-ylethyl)amino]-1,3-benzothiazole-4,7-dione;
-5-[[2-(dimethylamino)ethyl](ethyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione;
-5-[[2-(dimethylamino)ethyl](methyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione;
or a pharmaceutically acceptable salt thereof.