I-pheny 1-3,4-dihydropyrimidin-2(1H)-one derivatives and their use

1. A compound of formula (I-B)

wherein

A represents a phenyl ring,

R 1 represents hydrogen, halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy and C 1 -C 4 -alkoxy,

R 2 represents para-substituted cyano,

R 3 represents hydrogen,

R 4 represents C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, C 6 -C 10 -arylaminocarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl, heterocyclyl or cyano, wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, mono- and di-C 1 -C 4 -alkyl-aminocarbonyl can be further substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, amino-carbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkylcarbonyl-amino, amino, mono- and di-C 1 -C 4 -alkylamino, heteroaryl, heterocyclyl, tri-(C 1 -C 6 -alkyl)-silyl and cyano,

R 5 represents C 1 -C 4 -alkyl

R 6A represents hydrogen, C 1 -C 6 -alkylcarbonyl, C 3 -C 8 -cycloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, mono- and di-C 1 -C 4 -alkylamino-carbonyl can be substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, amino, mono- and di-C 1 -C 4 -alkylamino,

R 6B represents C 1 -C 6 -alkyl, which can be substituted with one to three identical or different radicals selected from the group consisting of hydroxy, C 1 -C 4 -alkoxy, amino, mono- and di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- and di-C 1 -C 4 -alkylamino-carbonyl, C 1 -C 4 -alkylcarbonyloxy, aminocarbonyloxy, cyano, aryl, heteroaryl and heterocyclyl, wherein heteroaryl and heterocyclyl can be further substituted with one to two identical or different radicals selected from the group consisting of C 1 -C 4 -alkyl, hydroxy and oxo,

R 7 represents halogen, or C 1 -C 4 -alkyl substituted with one to three identical or different halogen radicals,

and

Y 1 , Y 2 , Y 3 and Y 4 each represent CH.

2. The compound of formula (I-B) according to claim 1 , wherein

A represents a phenyl ring,

R 1 represents hydrogen, halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy and C 1 -C 4 -alkoxy,

R 2 represents para-substituted cyano,

R 3 represents hydrogen,

R 4 represents C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, C 6 -C 10 -arylaminocarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl, heterocyclyl or cyano, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl can be further substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkylcarbonylamino, amino, mono- and di-C 1 -C 4 -alkylamino, heteroaryl, heterocyclyl and tri-(C 1 -C 6 -alkyl)-silyl,

R 5 represents C 1 -C 4 -alkyl

R 6A represents hydrogen, C 1 -C 6 -alkylcarbonyl, C 3 -C 8 -cycloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl can be substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, amino, mono- and di-C 1 -C 4 -alkylamino,

R 6B represents C 1 -C 6 -alkyl, which can be substituted with one to three identical or different radicals selected from the group consisting of hydroxy, C 1 -C 4 -alkoxy, amino, mono- and di-C 1 -C 4 -alkylamino, aryl, heteroaryl and heterocyclyl,

R 7 represents halogen or C 1 -C 4 -alkyl, substituted with one to three identical or different halogen radicals,

and

Y 1 , Y 2 , Y 3 and Y 4 each represent CH.

3. The compound of formula (I-B) according to claim 1 , wherein

A represents a phenyl ring,

R 1 represents hydrogen, fluoro, chloro, bromo, nitro, cyano, methyl, ethyl, trifluoromethyl or trifluoromethoxy,

R 2 represents para-substituted cyano,

R 3 represents hydrogen,

R 4 represents C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl or cyano, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl and mono-C 1 -C 4 -alkylaminocarbonyl can be substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 6 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, amino, mono- or di-C 1 -C 4 -alkylamino, heteroaryl and heterocyclyl,

R 5 represents methyl or ethyl,

R 6A represents hydrogen, C 1 -C 6 -alkylcarbonyl or C 3 -C 6 -cycloalkylcarbonyl, wherein C 1 -C 6 -alkylcarbonyl can be substituted with a radical selected from the group consisting of C 3 -C 6 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, amino, mono- and di-C 1 -C 4 -alkylamino,

R 6B represents C 1 -C 6 -alkyl, which can be substituted with a radical selected from the group consisting of hydroxy, C 1 -C 4 -alkoxy, amino, mono- and di-C 1 -C 4 -alkylamino, phenyl, heteroaryl and heterocyclyl,

R 7 represents halogen, trifluoromethyl, or trifluoromethoxy,

and

Y 1 , Y 2 , Y 3 and Y 4 each represent CH.

4. The compound of formula (I-B) according to claim 1 , wherein

A represents a phenyl ring,

R 1 and R 3 each represent hydrogen,

R 2 represents para-substituted cyano,

R 4 represents C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkoxycarbonyl, wherein C 1 -C 4 -alkoxycarbonyl can be substituted with a radical selected from the group consisting of hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, mono- and di-C 1 -C 4 -alkylamino, heteroaryl and heterocyclyl,

R 5 represents methyl,

R 6A represents hydrogen, C 1 -C 6 -alkylcarbonyl or C 3 -C 6 -cycloalkylcarbonyl,

R 6B represents C 1 -C 4 -alkyl, which can be substituted with a radical selected from the group consisting of hydroxy, C 1 -C 4 -alkoxy, amino, di-C 1 -C 4 -alkylamino, phenyl, pyridyl, imidazolyl, pyrrolidino and morpholino,

R 7 represents trifluoromethyl,

and

Y 1 , Y 2 , Y 3 and Y 4 each represent CH.

5. The compound of formula (I-B) according to claim 1 , where wherein R 1 is hydrogen.

6. The compound of formula (I-B) according to claim 1 , wherein R 5 is methyl.

7. The compound of formula (I-B) according to claim 1 , wherein R 7 is trifluoromethyl.

8. The compound of formula (I-B) according to claim 1 , wherein R 6B is methyl, (1H-imidazol-2-yl)methyl, 2-(diethylamino)ethyl, 2-hydroxyethyl, 3-hydroxypropyl and 2-(1-pyrrolidinyl)ethyl.

9. A compound of formula (I-E)

wherein

Z represents CH,

R 1 , R 3 and R 4 have the meaning indicated in claim 1 , and

R 6B represents C 1 -C 4 -alkyl, which can be substituted with a radical selected from the group consisting of hydroxy, di-C 1 -C 4 -alkylamino, phenyl, pyridyl, imidazolyl, pyrrolidino and morpholino.

10. A process for synthesizing a compound of formula (I-B) or (I-E), as defined in claim 1 , by condensing a compound of formula (II)

wherein A, R 1 and R 2 have the meaning indicated in claim 1 or 9 ,

with a compound of formula (III)

wherein R 4 and R 5 have the meaning indicated in claim 1 or 9 ,

and a compound of formula (IV)

wherein R 3 , R 7 , and Y 1 to Y 4 have the meaning indicated in claim 1 or 9 ,

in the presence of an acid either in a three-component/one-step reaction or sequentially to give a compound of formula (I-D)

wherein

A, R 1 to R 5 , R 7 , and Y 1 to Y 4 have the meaning indicated in claim 1 or 9 ,

followed by reaction of a compound of formula (I-D) in the presence of a base

with a compound of formula (VI)

R 6B—X B   (VI),

wherein R 6B has the meaning indicated in claim 1 or 9 , and X B represents a leaving group

to give a compound of formula (I-B) or (I-E).

11. A composition containing at least one compound of formula (I-B) or (I-E), as defined in claim 1 or 9 , and a pharmacologically acceptable diluent.

12. A process for the preparation of a composition according to claim 11 characterized in that the compounds of general formula (I-B) or (I-E), as defined in claim 1 or 9 , together with customary auxiliaries are brought into a suitable application form.