Hetrocyclic aryl sulphonamides

1. A compound of the general formula (I)

in which

R 2 and R 3 are identical or different and represent hydrogen, hydroxyl, halogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, (C 1 –C 6 )-alkyl, (C 1 –C 6 )-alkoxy or a group of the formula

 in which

R 5 , R 6 and R 7 are identical or different and in each case represent hydrogen or (C 1 –C 6 )-alkyl, which for its part can be substituted by one or two substituents selected from the group consisting of hydroxyl, halogen, cyano, trifluoromethyl and trifluoromethoxy,

A represents a five- or six-membered heteroaryl linked via a C atom to the adjacent phenyl ring,

R 1 represents the radical

 in which

R 11 represents the side group of an amino acid, and the amino group in R 1 can optionally be mono- or polysubstituted by (C 1 –C 6 )alkyl, alkylcarbonyl, or phenyl,

or

R 1 represents a straight-chain or branched (C 1 –C 5 )-alkyl radical, which for its part can be substituted by one or more groups selected from phenyl, piperidinyl, pyridinyl, thiazolyl, thienyl,

 or a group

 in which

R 12 and R 13 are identical or different and can represent hydrogen, (C 1 –C 6 )alkyl, alkylcarbonyl, an amino protective group, or phenyl,

or

R 1 represents a radical

 or

R 1 represents a straight-chain or branched (C 1 –C 5 )-alkyl radical, which for its part is substituted by a group

 in which

R 14 , R 15 , R 16 are identical or different and represent hydrogen or (C 1 –C 6 )alkyl

 and

n can assume the values 2 or 3,

or

R 1 represents piperidinyl or the radical

 in which

R 12 and R 13 have the meaning indicated above,

n represents a number from 1 to 4 and the ring can be up to trisubstituted in an identical or different manner by halogen, (C 1 –C 6 )-alkyl, halogeno-(C 1 –C 6 )-alkyl, amino, or hydroxyl,

R 4 represents tert-butyl, which is optionally up to trisubstituted, in an identical or different manner, by hydroxyl, fluorine or chlorine, or

 represents cyclopropyl or cyclobutyl, which are mono- to trisubstituted in an identical or independent manner by halogen or (C 1 –C 6 )-alkyl, (C 1 –C 6 )-alkyl optionally being substituted by hydroxyl, fluorine or chlorine,

and in which

X represents oxygen or sulphur,

and in which nitrogen-containing heterocycles can also be present as N-oxides,

or a tautomer, stereoisomer, or mixture of stereoisomers of said compound, or a pharmacologically tolerable salt of said compound, tautomer, stereoisomer, or mixture of stereoisomers.

2. The compound of the general formula (I) according to claim 1 ,

in which

R 2 and R 3 are identical or different and represent hydrogen or halogen,

A represents the radical (A-I)

which is linked via one of the carbon atoms of positions 3 or 5 to the adjacent phenyl ring,

and in which

Y represents oxygen,

or

A represents the radical (A-II)

 which is linked via one of the carbon atoms of positions 2 or 5 to the adjacent phenyl ring,

 and in which

Y represents oxygen,

R 1 represents the radical

 in which

R 11 represents the side group of an amino acid, and the amino group in R 1 can optionally be mono- or polysubstituted by (C 1 –C 6 )-alkyl, alkylcarbonyl, an amino protective group, or phenyl,

or

R 1 represents a straight-chain or branched (C 1 –C 5 )-alkyl radical, which for its part can be substituted by one or more groups selected from phenyl, piperidinyl, pyridinyl, thiazolyl, thienyl,

 a group

 in which

R 12 and R 13 are identical or different and can represent hydrogen, (C 1 –C 6 )-alkyl, alkylcarbonyl, an amino protective group, or phenyl,

or

R 1 represents a straight-chain or branched (C 1 –C 5 )-alkyl radical, which for its part is substituted by a group

 in which

R 14 , R 15 , R 16 are identical or different and represent hydrogen or methyl

and

n can assume the values 2 or 3,

or

R 1 represents piperidin-3-yl or the radical

R 4 represents tert-butyl, which is optionally up to trisubstituted, in an identical or different manner, by hydroxyl, fluorine or chlorine, or

 represents cyclopropyl or cyclobutyl, which is substituted in the α-position to the carbonyl group or thiocarbonyl group by methyl, which for its part is optionally substituted by hydroxyl, fluorine or chlorine,

and in which

X represents oxygen,

and in which nitrogen-containing heterocycles can also be present as N-oxides,

or a tautomer, stereoisomer or mixture of stereoisomers of said compound, or a pharmacologically tolerable salt of said compound tautomer, stereoisomer, or mixture of stereoisomers.

3. The compound of the general formula (I) according to claim 1 ,

in which

R 2 and R 3 represent hydrogen,

A represents one of the radicals

R 1 represents the radical

 in which

R 11 represents the side group of an amino acid, and the amino group in R 1 can optionally be mono- or polysubstituted by methyl, alkylcarbonyl, an amino protective group, or phenyl,

or

R 1 represents a straight-chain or branched (C 1 –C 5 )-alkyl radical, which for its part can be substituted by one or more groups selected from phenyl, piperidinyl, pyridinyl, thiazolyl, thienyl,

 or a group

 in which

R 12 and R 13 are identical or different and can represent hydrogen, methyl, alkylcarbonyl, an amino protective group, or phenyl,

or

R 1 represents a straight-chain or branched (C 1 –C 5 ) alkyl radical, which for its part is substituted by a group

 in which

R 14 , R 15 , R 16 are identical or different and represent hydrogen or methyl

and

n can assume the values 2 or 3,

or

R 1 represents piperidin-3-yl or the radical

R 4 represents tert-butyl, which is optionally up to trisubstituted, in an identical or different manner, by hydroxyl, fluorine or chlorine, or

 represents cyclopropyl or cyclobutyl, which is substituted in the α-position to the carbonyl group or thiocarbonyl group by methyl, which for its part is optionally substituted by hydroxyl, fluorine or chlorine,

and in which

X represents oxygen,

and in which nitrogen-containing heterocycles can also be present as N-oxides,

or a tautomer, stereoisomer, or mixture of stereoisomers of said compound or a pharmacologically tolerable salt of said compound, tautomer, stereoisomer, or mixture of stereoisomers.

4. The compound of the general formula (I) according to claim 1 ,

in which

R 4 represents one of the radicals

5. A compound of the general formula (Ia)

in which

R 1 , R 2 , R 3 , R 4 , A and X have the meanings indicated above in claim 1 .

6. The compound of the general formula (I) according to claim 1 ,

in which

A represents a 3-linked 1,2,4-oxadiazole.

7. The compound of the general formula (I) according to claim 1 , which is selected from the group consisting of the following compounds:

8. A process for the preparation of compounds of the general formula (I) according to claim 1 , in which a compound of the general formula (D-1)

in which

X, R 2 , R 3 and R 4 have one of the meanings indicated above in claim 1 ,

is acylated with a carboxylic acid of the general formula (E-1)

R 1 —COOH  (E-1)

in which

R 1 has the meaning indicated above in claim 1 and free amino groups contained in R 1 are present protected by amino protective groups,

in the presence of a condensing agent and of a base, and the acylated amidoxime is cyclized to the 1,2,4-oxadiazole.

9. A process for the preparation of compounds of the general formula (I) according to claim 1 ,

in which a compound of the general formula (G-2)

in which

R 1 , R 2 , R 3 , R 4 and X have the meaning indicated above in claim 1 ,

are cyclized.

10. A compound of the general formula (D-1)

in which R 2 , R 3 , R 4 and X have the meanings indicated in claim 1 .

11. A compound of the general formula (G-2)

in which R 1 , R 2 , R 3 , R 4 and X have the meanings indicated in claim 1 .

12. A pharmaceutical composition comprising a compound of the general formula (I) according to any one of claims 1 to 7 .

13. A method for the treatment of cytomegalovirus infection, comprising administering an effective amount of a compound of claim 1 .