Patent EP-0292305-A1 (EP)
Inventor: ENOMOTO MASAO
IPC: C07D417/04
Filed: 1988-05-20
Abstract: Thiazolidin-4-one derivatives are represented by the following general formula (I)
     wherein.
       
R 1  and R 2  are the same or different and denote each
   (i) a residue represented by the general formula -A- R4     wherein, A denotes a single bond, C 1 -C 8  alkylene, C 2 -C 8  alkenylene, or C 2 -C 8  alkynylene and R 4  denotes hydrogen, C 1 -C 12  alkyl, C 2 -C 8  alkenyl, C 3 -C 8  cycloalkyl, or C 1 -C 6  haloalkyl, or   (ii) a residue represented by the general formula
     wherein, B denotes a single bond or C 1 -C 6  alkylene, R 5  denotes hydrogen, C 1 -C 6  alkyl, C 2 -Cs alkenyl, C 3 -C 8  cycloalkyl, substituted silyl, or substituted or unsubstituted aryl, n and n' denote each an integer of 2 to 4, m denotes an integer of 1 to 3, and m' denotes an integer of 0 to 2; and       R 3  denotes hydrogen, C 1 -C 2  alkyl, allyl, 2-propynyl, or a residue represented by
   (a) the general formula
     wherein, R 6  denotes halogen, an aryl group substituted or unsubstituted by one or more hydroxy or C 1 -C 4  alkoxy groups, or a residue represented by the general formula -D-R 7  (D denotes oxygen or sulfur and R 7  denotes hydrogen, C 1 -C 4  alkyl, or Ci-C 4  alkanol) and ℓ denotes an integer of 2 to 4,   (b) the general formula
     wherein, E denotes oxygen, sulfur, imino, or C 1 -C 4  alkylimino, R a  denotes hydrogen or C 1 -C 4  alkyl, or -(E-R 8 ) denotes a 5- to 7-membered cyclic amino group which optionally contains other hetero atoms, and k denotes an integer of 1 to 3, or   (c) the general formula -F- R9   
wherein, F denotes C 2 -C 6  alkylene and R 9  denotes a nitrogen-containing heterocyclic aromatic residue or an amino group represented by the general formula
     (R 10  denotes hydrogen, C 1 -C 4  alkyl, or C 1 -C 4  alkyl or R 10  in combination with R 11  denotes a 5- to 7-membered cyclic amino group which optionally contains other hetero atoms), with the proviso that, when R 1  is hydrogen and       R 2  is methyl, R 3  denotes hydrogen, Ci-C 2  alkyl, 2-propynyl, or a residue represented by
   (a) the general formula
       
wherein, R 6  denotes halogen, an aryl group substituted or unsubstituted by one or more hydroxy or C 1 -C 4  alkoxy groups, or a residue represented by the general formula -D-R 7  (D denotes oxygen or sulfur and R 7  denotes hydrogen, C 1 -C 4  alkyl, or C 1 -C 4  alkanoyl) and ℓ denotes an integer of 2 to 4,   (b) the general formula
       
wherein, E denotes oxygen, sulfur, imino, or C 1 -C 4  alkylimino, denotes hydrogen or C 1 -C 4  alkyl, or -(E-R 8 ) denotes a 5- to 7-membered cyclic amino group which optionally contains other hetero atoms, and k denotes an integer of 1 to 3, or   (c) the general formula -F- R 9  
wherein, F denotes C 2 -C 6  alkylene and R 9  denotes a nitrogen-containing heterocyclic aromatic residue or an amino group represented by the general formula
     (R 10  denotes hydrogen, C 2 -C 4  alkyl or C 1 -C 4  alkanoyl and R 11  denotes hydrogen or C 1 -C 4  alkyl or R 10  in combination with R 11  denotes a 5- to 7-membered cyclic amino group which optionally contains other hetero atoms.  
Since these derivatives, and acid addition salts thereof have selective PAF-antagonistic activities, these compounds are very useful as preventive and curative agents for PAF-induced diseases, for example, various kinds of inflamation, allergic diseases, circulatory diseases, and gastro-intestinal diseases.