Substituted and unsubstituted benzooxathiazoles and compounds derived therefrom

Abstract

The invention relates to substituted and unsubstituted 3H-benzo[1,2,3]oxathiazole 2,2-dioxides, 1,3-dihydrobenzo[1,2,5]thiadiazole 2,2-dioxides and 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides, to their preparation and to their use in medicaments.

We claim:  
     
         1 . A compound of the formula I  
       
         
           
           
               
               
           
         
       
       in which 
 X is CH 2 , O, N;  
 Y is CH 2 , O, N;  
 R1, R2, R3 are each independently of one another 
 H, F, Cl, Br, I, NH 2 , OH, NO 2 , COOH;  
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-,3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl; or in each case two of the radicals R1 and R2 or R2 and R3 or R1 and R3 together form a fused aryl radical, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 or its physiologically acceptable salts or prodrugs.  
 
 
     
     
         2 . A compound of the formula I as claimed in  claim 1 , wherein 
 X is O, N;    Y is O, N;    R1 is H, F, Cl, Br, I, NH 2 , OH, NO 2 , COOH; 
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
   R2 is H, F, Cl, Br, I, NH 2 , OH, NO 2 , COOH; 
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
   R3 is H, F, Cl, Br, I, NH 2 , OH, NO 2 , COOH; 
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
 or its physiologically acceptable salts or prodrugs.  
   
     
     
         3 . A compound of the formula I as claimed in  claim 1 , wherein 
 X is O, N;    Y is N;    R1 is H, F, Cl, Br, I, NH 2 , OH, NO 2 , COOH; 
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -CO 0 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
   R2 is H, F, Cl, Br, I, NH 2 , OH, NO 2 , COOH; 
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, —COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
   R3 is COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ; 
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
 or its physiologically acceptable salts or prodrugs.  
   
     
     
         4 . A compound of the formula I as claimed in  claim 1 , wherein 
 X is O;    Y is N;    R1 is H, F, Cl, Br, I, NH 2 , OH, NO 2 , COOH; 
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
   R2 is F, Cl, Br, I, NH 2 , OH, NO 2 , COOH; 
 COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where the phenyl may be mono- to trisubstituted by O—(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CONH(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replace by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
   R3 is COO(C 1 -C 6 )alkyl, CONH 2 , CONH(C 1 -C 16 )alkyl, CONH(C 1 -C 16 )alkenyl, CONH(C 1 -C 6 )alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C 1 -C 10 )alkyl or O—(C 1 -C 10 )alkyl-phenyl, CON H(C 1 -C 6 )alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ; 
 O—(C 1 -C 6 )alkyl;  
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkyl-COOH, (C 1 -C 6 )alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 Phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl or 2- or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF 3 , NO 2 , CN, OCF 3 , O—(C 1 -C 10 )alkyl, NH 2 , NH(C 1 -C 6 )alkyl, COOH, COO(C 1 -C 6 )alkyl, CONH 2 ;  
 (C 3 -C 18 )cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C 1 -C 6 )alkyl-phenyl or O—(C 1 -C 6 )alkyl-phenyl,  
 NCO, NSO 3 —(C 1 -C 10 )alkyl;  
 or its physiologically acceptable salts or prodrugs.  
   
     
     
         5 . A pharmaceutical composition comprising an effective amount of at least one compound as claimed in  claim 1  and a pharmaceutically acceptable excipient.  
     
     
         6 . A method of inhibiting a PTPase comprising administering to a subject in need thereof an effective amount of one or more compounds of  claim 1 .  
     
     
         7 . The method of  claim 6 , wherein the PTPase is PTP1B, CD45, LAR, SHP-1, SHP-2, PTPa or HePTP.  
     
     
         8 . A method of treating type 1 diabetes comprising administering to a subject in need thereof an effective amount of one or more compounds of  claim 1 .  
     
     
         9 . A method of treating type 2 diabetes comprising administering to a subject in need thereof an effective amount of one or more compounds of  claim 1 .  
     
     
         10 . A method of treating insulin resistance comprising administering to a subject in need thereof an effective amount of one or more compounds of  claim 1 .  
     
     
         11 . A method of treating pathological obesity comprising administering to a subject in need thereof an effective amount of one or more compounds of  claim 1 .  
     
     
         12 . A method of preparing a pharmaceutical composition comprising the steps of mixing one or more compounds of  claim 1  with one or more pharmaceutically acceptable excipients and bringing this mixture into a form suitable for administration.