New thiazolidinones without basic nitrogen, their production and use as pharmaceutical agents
The invention relates to thiazolidones of general formula (I): to their production and to their use as inhibitors of the polo-like kinase (Plk) for treating various diseases.
1 . A compound of general formula I:
in which:
Q stands for aryl,
A and B, independently of one another, stand for hydrogen, halogen, hydroxy, —NR 3 R 4 , cyano or nitro,
or
for C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy or C 3 -C 6 -heterocycloalkyl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, C 3 -C 6 -heterocycloalkyl or with the group —NR 3 R 4 or —CO(NR 3 )-M, whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring and/or the ring itself optionally can be substituted in one or more places, in the same way or differently, with C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl or with the group —NR 3 R 4 ,
or
for —NR 3 C(O)-L, —NR 3 C(O)-NR 3 -L, —COR 6 , —O—(CH 2 ) p R 6 , —CO(NR 3 )-M, —NR 3 (CS)NR 3 R 4 , —NR 3 SO 2 -M, —SO 2 —NR 3 R 4 , —SO 2 (NR 3 )-M or —O—(CH 2 ) p aryl,
P stands for an integer of 0, 1, 2, 3, or 4,
L stands for C 1 -C 6 -alkyl or C 3 -C 6 -heterocycloalkyl that optionally is substituted in one or more places, in the same way or differently, with C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxyalkoxy, C 3 -C 6 -heterocycloalkyl or with the group —NR 3 R 4 , whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring, and/or the ring itself optionally can be substituted in one or more places, in the same way or differently, with C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl or with the group —NR 3 R 4 ,
M stands for C 1 -C 6 -alkyl that optionally is substituted in one or more places, in the same way or differently, with the group —NR 3 R 4 or C 3 -C 6 -heterocycloalkyl, x stands for —NH— or —NR 5 —,
R 1 stands for C 1 -C 4 -alkyl, C 3 -cycloalkyl, allyl or propargyl that optionally is substituted in one or more places, in the same way or differently, with halogen,
R 2 stands for hydrogen or for C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkenyl, C 1 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl, aryl or heteroaryl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -hydroxyalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl, C 1 -C 6 -alkynyl, aryl, aryloxy, heteroaryl or with the group-S—C 1 -C 6 -alkyl, —COR 6 , —NR 3 R 4 , —NR 3 C(O)-L or —NR 3 COOR 7 ,
whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 groups in the ring and/or optionally one or more double bonds can be contained in the ring,
and whereby aryl, heteroaryl, C 3 -C 6 -cycloalkyl- and/or the C 3 -C 6 -heterocycloalkyl ring in each case itself optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, or C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl, aryl, benzyl or heteroaryl that optionally is substituted in one or more places, in the same way or differently, with halogen,
or
for the group —NR 3 R 4 , —NR 3 C(O)-L, or —NR 3 (CS)NR 3 R 4 ,
or
R 2 and R 5 together form a C 3 -C 6 -heterocycloalkyl ring, which is interrupted at least once by nitrogen and optionally can be interrupted in one or more places by oxygen or sulfur and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring,
and/or the ring itself optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, hydroxy, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxyalkyl or with the group —NR 3 R 4 or —COR 6 ,
and/or can be substituted with aryl or heteroaryl that optionally is substituted in one or more places, in the same way or differently, with halogen, C 1 -C 6 -alkoxy or with the group —COR 6 ,
R 3 and R 4 , independently of one another, stand for hydrogen or for C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, —CO—C 1 -C 6 -alkyl or aryl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, C 3 -C 6 -heterocycloalkyl, C 1 -C 6 -hydroxyalkoxy or with the group —NR 3 R 4 , whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring, and
whereby the C 3 -C 6 -heterocycloalkyl ring itself optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, or with the group —NR 3 R 4 or —CO—NR 3 R 4 ,
or
R 3 and R 4 together form a C 3 -C 6 -heterocycloalkyl ring, which is interrupted at least once by nitrogen and optionally can be interrupted in one or more places by oxygen or sulfur and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring, and/or the heterocycloalkyl ring itself optionally can be substituted in one or more places, in the same way or differently, with C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxyalkyl, cyano, hydroxy or with the group —NR 3 R 4 ,
R 5 stands for C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, or C 1 -C 6 -alkynyl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, cyano, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl, or with the group —NR 3 R 4 ,
whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 groups in the ring and/or optionally one or more double bonds can be contained in the ring, and
whereby the C 3 -C 6 -heterocycloalkyl ring itself in each case optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, or with the group —NR 3 R 4 or —CO—NR 3 R 4 ,
R 6 stands for hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or the group —NR 3 R 4 ,
R 7 stands for —CH 2 ) n -aryl or —CH 2 )n-heteroaryl, and
n stands for an integer of 1, 2, 3, 4, 5 or 6,
as well as the solvates, hydrates, stereoisomers, diastereomers, enantiomers and salts thereof.
2 . The compound of general formula I according to claim 1 , in which:
Q stands for phenyl,
A and B, independently of one another, stand for hydrogen, halogen, hydroxy, —NR 3 R 4 , cyano or nitro,
or
for C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy or C 3 -C 6 -heterocycloalkyl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, C 3 -C 6 -heterocycloalkyl or with the group —NR 3 R 4 or —CO(NR 3 )-M,
whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms, and/or optionally can be interrupted by one or more —C(O)— or —SO 2 groups in the ring and/or optionally one or more double bonds can be contained in the ring and/or the ring itself optionally can be substituted in one or more places, in the same way or differently, with C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl or with the group —NR 3 R 4 ,
or
for —NR 3 C(O)-L, —NR 3 C(O)-NR 3 -L, —COR 6 , —O—(CH 2 ) p R 6 , —CO(NR 3 )-M,
—NR 3 (CS)NR 3 R 4 , —NR 3 SO 2 -M, —SO 2 —NR 3 R 4 , —SO 2 (NR 3 )-M or —O—(CH 2 ) p aryl,
p stands for an integer of 0, 1, 2, 3, or 4,
L stands for C 1 -C 6 -alkyl or C 3 -C 6 -heterocycloalkyl that optionally is substituted in one or more places, in the same way or differently, with C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxyalkoxy, C 3 -C 6 -heterocycloalkyl or with the group —NR 3 R 4 ,
whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 groups in the ring and/or optionally one or more double bonds can be contained in the ring and/or the ring itself optionally can be substituted in one or more places, in the same way or differently, with C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl or with the group —NR 3 R 4 ,
M stands for C 1 -C 6 -alkyl that optionally is substituted in one or more places, in the same way or differently, with the group —NR 3 R 4 or C 3 -C 6 -heterocycloalkyl,
X stands for —NH— or —NR 5 —,
R 1 stands for C 1 -C 4 -alkyl, C 3 -cycloalkyl, allyl or propargyl that optionally is substituted in one or more places, in the same way or differently, with halogen,
R 2 stands for hydrogen or for C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkenyl, C 1 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl, aryl or heteroaryl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -hydroxyalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl, C 1 -C 6 -alkynyl, aryl, aryloxy, heteroaryl or with the group —S—C 1 -C 6 -alkyl, —COR 6 , —NR 3 R 4 , —NR 3 C(O)-L or —NR 3 COOR 7 ,
whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 groups in the ring and/or optionally one or more double bonds can be contained in the ring,
and whereby aryl, heteroaryl, C 3 -C 6 -cycloalkyl and/or the C 3 -C 6 -heterocycloalkyl ring in each case itself optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl; C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl, aryl, benzyl or heteroaryl that optionally is substituted in one or more places, in the same way or differently, with halogen,
or
for the group —NR 3 R 4 , —NR 3 C(O)-L, —NR 3 (CS)NR 3 R 4 ,
or
R 2 and R 5 together form a C 3 -C 6 -heterocycloalkyl ring, which is interrupted at least once by nitrogen and optionally can be interrupted in one or more places by oxygen or sulfur and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring,
and/or the ring itself optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, hydroxy, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxyalkyl or with the group —NR 3 R 4 or —COR 6 and/or can be substituted with aryl or heteroaryl that optionally is substituted in one or more places, in the same way or differently, with halogen, C 1 -C 6 -alkoxy or with the group —COR 6 ,
R 3 and R 4 , independently of one another, stand for hydrogen or for C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, —CO—C 1 -C 6 -alkyl or aryl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, C 3 -C 6 -heterocycloalkyl, C 1 -C 6 -hydroxyalkoxy or with the group —NR 3 R 4 , whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring, and
whereby the C 3 -C 6 -heterocycloalkyl ring itself in each case optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl or with the group —NR 3 R 4 or —CO—NR 3 R 4 ,
or
R 3 and R 4 together form a C 3 -C 6 -heterocycloalkyl ring, which is interrupted at least once by nitrogen and optionally can be interrupted in one or more places by oxygen or sulfur and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring
and/or the heterocycloalkyl ring itself optionally can be substituted in one or more places, in the same way or differently, with C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxyalkyl, cyano, hydroxy or with the group —NR 3 R 4 ,
R 5 stands for C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl or C 1 -C 6 -alkynyl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, cyano, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -heterocycloalkyl or with the group —NR 3 R 4 , whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring and
whereby the C 3 -C 6 -heterocycloalkyl ring itself in each case optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, or with the group —NR 3 R 4 or —CO—NR 3 R 4 ,
R 6 stands for hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or the group —NR 3 R 4 ,
R 7 stands for —(CH 2 ) n -aryl or —(CH 2 ) n -heteroaryl and
n stands for an integer of 1, 2, 3, 4, 5 or 6,
as well as the stereoisomers, diastereomers, enantiomers and salts thereof.
3 . The compound of general formula I according to claim 1 , in which:
Q stands for phenyl,
A and B, independently of one another, stand for hydrogen, halogen, or for C 1 -C 4 -alkyl or pyrrolidinyl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy or with the group —NR 3 R 4 or —CO(NR 3 )-M,
M stands for C 1 -C 6 -alkyl that optionally is substituted in one or more places, in the same way or differently, with the group —NR 3 R 4 or C 3 -C 6 -heterocycloalkyl,
X stands for —NH—,
R 1 stands for C 1 -C 4 -alkyl that optionally is substituted in one or more places, in the same way or differently, with halogen,
R 2 stands for hydrogen or for C 1 -C 6 -alkyl or C 1 -C 6 -alkynyl that optionally is substituted in one or more places, in the same way or differently, with halogen, cyano, or C 1 -C 6 -alkoxy,
R 3 and R 4 , independently of one another, stand for hydrogen or for C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, —CO—C 1 -C 6 -alkyl or aryl that optionally is substituted in one or more places, in the same way or differently, with halogen, hydroxy, C 3 -C 6 -heterocycloalkyl, C 1 -C 6 -hydroxyalkoxy or with the group —NR 3 R 4 , whereby the heterocycloalkyl itself optionally can be interrupted by one or more nitrogen, oxygen and/or sulfur atoms, and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring, and
whereby the C 3 -C 6 -heterocycloalkyl ring itself optionally can be substituted in one or more places, in the same way or differently, with cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, or with the group —NR 3 R 4 or —NR 3 R 4 ,
or
R 3 and R 4 together form a C 3 -C 6 -heterocycloalkyl ring, which is interrupted at least once by nitrogen and optionally is interrupted in one or more places by oxygen or sulfur and/or optionally can be interrupted by one or more —C(O)— or —SO 2 — groups in the ring and/or optionally one or more double bonds can be contained in the ring, and/or the heterocycloalkyl ring itself optionally can be substituted in one or more places, in the same way or differently, with C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxyalkyl, cyano, hydroxy or with the group —NR 3 R 4 , and
R 6 stands for hydroxy or C 1 -C 6 -alkoxy,
as well as the solvates, hydrates, stereoisomers, diastereomers, enantiomers and salts thereof.
4 . The compound of general formula I according to claim 1 , in which:
Q stands for phenyl,
A and B, independently of one another, stand for hydrogen, halogen, hydroxy, methoxy or pyrrolidinyl,
X stands for —NH—,
R 1 stands for ethyl,
R 2 stands for ethyl or propynyl,
as well as the solvates, hydrates, stereoisomers, diastereomers, enantiomers and salts thereof
5 . The compound of general formula I according to claim 1 , which is selected from the group consisting of:
2-Cyano-N-ethyl-2-[3-ethyl-4-oxo-5-[1-(4-pyrrolidin-1-yl-phenyl)-meth-(Z)-ylidene]-thiazolidin-(2Z)-ylidene]-acetamide; 2-Cyano-N-ethyl-2-[3-ethyl-5-[1-(3-hydroxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-acetamide; 2-Cyano-N-ethyl-2-[3-ethyl-5-[1-(4-hydroxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-acetamide; 2-[5-[1-(4-Bromo-phenyl)-meth-(Z)-ylidene]-3-ethyl-4-oxo-thiazolidin-(2Z)-ylidene]-2-cyano-N-ethyl-acetamide; 2-Cyano-N-ethyl-2-[3-ethyl-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-acetamide; 2-Cyano-N-ethyl-2-[3-ethyl-5-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-acetamide; 2-Cyano-2-[3-ethyl-5-[1-(3-hydroxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-N-prop-2-ynyl-acetamide; 2-Cyano-2-[3-ethyl-5-[1-(4-hydroxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-N-prop-2-ynyl-acetamide; 2-Cyano-2-[3-ethyl-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-N-prop-2-ynyl-acetamide; 2-Cyano-2-[3-ethyl-4-oxo-5-[1-(4-pyrrolidin-1-yl-phenyl)-meth-(Z)-ylidene]-thiazolidin-(2Z)-ylidene]-N-prop-2-ynyl-acetamide; 2-Cyano-2-[3-ethyl-5-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-N-prop-2-ynyl-acetamide; 2-Cyano-2-[3-ethyl-5-[1-(3-hydroxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-N-(2-hydroxy-1,1-dimethyl-ethyl)-acetamide; 2-Cyano-2-[3-ethyl-5-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-4-oxo-thiaz-olidin-(2Z)-ylidene]-N-(2-hydroxy-1,1-dimethyl-ethyl)-acetamide; and 2-Cyano-2-[3-ethyl-5-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidene]-N-(2-hydroxy-1,1-dimethyl-ethyl)-acetamide.
6 . A method of preparing a compound of general formula (I) according to claim 1 , wherein a carboxylic acid of general formula (3):
(3)
is allowed to react with a compound of general formula (3′):
R 2 —XH (3′);
thus providing a compound of general formula (I):
in which formulae (3), (3′) and (I), the definitions of substituents R 1 , R 2 , A, B, Q, and X being according to claim 1 .
7 . The method according to claim 6 , wherein said carboxylic acid of general formula (3) is prepared by allowing an allyl ester of general formula (2):
(2)
to be saponified in the presence of Pd-tetrakis-triphenylphosphine and barbituric acid, in which formula (2) the definitions of substituents R 1 , A, B, and Q being according to above.
8 . The method according to claim 7 , wherein said allyl ester of general formula (2) is prepared by allowing a thiazolidinone of general formula (1):
to be condensed with an aldehyde of general formula (1′):
in which formulae (1) and (1′), the definitions of substituents R 1 , A, B, and Q being according to above.
9 . A method of preparing a compound of general formula (I) according to claim 1 , wherein a thiazolidinone of general formula (5):
is allowed to be condensed with an aldehyde of general formula (1′):
thus providing a compound of general formula (I):
in which formulae (5), (1′) and (I), the definitions of substituents R 1 , R 2 , A, B, Q, and X being according to claim 1 .
10 . The method according to claim 9 , wherein said thiazolidinone of general formula (5) is prepared by allowing a carboxylic acid of general formula (4):
to react with a compound of general formula (3′):
R 2 —XH (3′);
in which formulae (4) and (3′), the definitions of substituents R 1 , R 2 and X being according to above.
11 . The method according to claim 10 , wherein said carboxylic acid of general formula (4) is prepared by allowing a thiazolidinone of general formula (1):
to be saponified in the presence of Pd-tetrakis-triphenylphosphine and barbituric acid, in which formula (1) the definition of the substituent R 1 being according to above.
12 . Use of a compound of general formula I, or of a compound as obtained according to claim 6 , for the production of a pharmaceutical agent for treating cancer, auto-immune diseases, chemotherapy agent-induced alopecia and mucositis, cardiovascular diseases, infectious diseases, nephrological diseases, chronic and acute neurodegenerative diseases and viral infections.
13 . Use according to claim 12 , wherein cancer is defined as solid tumours and leukemia; auto-immune diseases are defined as psoriasis, alopecia and multiple sclerosis; cardiovascular diseases are defined as stenoses, arterioscleroses, and restenoses; infectious diseases are defined as diseases that are caused by unicellular parasites; nephrological diseases are defined as glomerulonephritis; chronic neurodegenerative diseases are defined as Huntington's disease, amyotrophic lateral sclerosis, Parkinson's disease, AIDS dementia and Alzheimer's disease; acute neurodegenerative diseases are defined as ischemias of the brain and neurotraumas; and viral infections are defined as cytomegalic infections, herpes, hepatitis B and C, and HIV diseases.
14 . A pharmaceutical agent, characterized in that it contains at least one compound according to Formula I, or as obtained by a method according to claim 6 .
15 . The pharmaceutical agent according to claim 14 for treating cancer, autoimmune diseases, cardiovascular diseases, infectious diseases, nephrological diseases, neurodegenerative diseases and viral infections.
16 . A compound according to Formula I, or as obtained according to claim 6 , or a pharmaceutical agent containing it, together with a suitable formulation substance and/or vehicle.
17 . Use of a compound of general formula I according to Formula I, or as obtained by a method according to claim 6 , or of a pharmaceutical agent containing it, as an inhibitor of a polo-like kinase.
18 . Use according to claim 17 , wherein said kinase is Plk1, Plk2, Plk3 or Plk4.
19 . Use of a compound of general formula I according to Formula I, or as obtained according to claim 6 , in the form of a pharmaceutical preparation for enteral, parenteral and oral administration.