Thiazolyl amide derivatives
The present invention relates to novel compounds, to a process for their preparation and to their use as medicaments, in particular as antiviral medicaments.
1. Compounds of the general formula (I):
in which
R 1 represents hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, amino-(C 1-C 6 )-alkyl or halogeno-(C 1 -C 6 )-alkyl,
R 2 and R 3 are identical or different and represent hydrogen, (C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkyl or biphenylaminocarbonyl, or
represent (C 1 -C 6 )-alkyl which is optionally substituted by 1 to 3 substituents selected from the group consisting of (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy, halogen, hydroxyl, amino, tri-(C 1 -C 6 )-alkylsilyloxy, radicals of the formula
in which R 2′ represents hydrogen or (C 1 -C 4 )-alkyl,
a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, where a nitrogen-containing heterocycle may also be attached via the nitrogen atom,
a 3- to 8-membered saturated or unsaturated nonaromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and
(C 6 -C 10 )-aryl which for its part may be substituted by hydroxyl or (C 1 -C 6 )-alkoxy, or
represent a group of the formula
in which R 8 and R 9 are identical to or different from one another and represent hydrogen and (C 1 -C 4 )-alkyl, or
represent a group of the formula
in which R 10 is the side-group of a naturally occurring α-amino acid, or
represent a group of the formula
in which R 11 represents (C 1 -C 4 )-alkyl and R 12 represents hydrogen, (C 1 -C 4 )-alkyl or represents a group of the formula
in which R 10′ is the side-group of a naturally occurring α-amino acid, or
R 2 and R 3 together with the nitrogen atom form a 5- or 6-membered saturated heterocycle which may optionally contain an oxygen atom,
R 4 represents hydrogen, (C 1 -C 6 )-acyl, (C 2 -C 6 )-alkenyl, (C 3 -C 8 )-cycloalkyl, or
R 4 represents (C 1 -C 6 )-alkyl which may optionally be substituted by 1 to 3 substituents selected from the group consisting of halogen, hydroxyl, (C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-acyl, (C 1 -C 6 )-alkoxy, carboxyl,
in which R 4′ represents hydrogen, —(OCH 2 CH 2 ) n OCH 2 CH 3 , in which n is 0 or 1, phenoxy, (C 6 -C 10 )-aryl and —NR 13 R 14 ,
in which R 13 and R 14 are identical or different and represent hydrogen, (C 1 -C 6 )-acyl, (C 1 -C 6 )-alkyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylamino-(C 1 -C 6 )-alkyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, (C 6 -C 10 )-aryl or (C 1 -C 6 )-alkoxycarbonyl, or
R 13 and R 14 together with the nitrogen atom form a 5- or 6-membered saturated heterocycle which may optionally contain a further heteroatom from the group consisting of S and O or a radical of the formula —NR 15 , and which may be substituted by oxo,
in which
R 15 represents hydrogen or (C 1 -C 4 )-alkyl, or
R 4 represents (C 1 -C 6 )-alkyl which is substituted by a 5- or 6-membered aromatic, optionally benzo-fused heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, where a nitrogen-containing heterocycle may also be attached via the nitrogen atom, or which is substituted by
radicals of the formulae
in which
R 16 represents hydrogen or (C 1 -C 6 )-alkyl,
R 17 and R 18 are identical or different and represent hydrogen, (C 1 -C 6 )alkyl or (C 6 -C 10 )-aryl, where abovementioned (C 1 -C 6 )-alkyl and (C 6 -C 10 )-aryl may optionally be substituted by 1 to 3 substituents selected from the group consisting of hydroxyl, (C 1 -C 6 )-alkoxy and halogen,
R 5 represents hydrogen, (C 1 -C 6 )-alkyl, halogen, amino, mono- or di-(C 1 -C 6 )-alkylamino or represents (C 1 -C 6 )-alkanoylamino,
R 6 represents phenyl which may optionally be substituted by one to three substituents selected from the group consisting of
halogen,
(C 6 -C 10 )-aryl which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogeno-(C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkoxy, amino, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsulphonyl, tri-(C 1 -C 6 )-alkylsilyloxy, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and/or cyano,
(C 1 -C 6 )-alkoxy,
(C 1 -C 6 )-alkoxycarbonyl,
(C 1 -C 6 )-alkylthio,
hydroxyl,
carboxyl,
partially fluorinated (C 1 -C 6 )-alkoxy having up to 6 fluorine atoms,
(C 1 -C 6 )-alkyl which is optionally substituted by a radical of the formula
a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O which may optionally be attached via a nitrogen atom and which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogeno-(C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkoxy, amino, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, carbamoyl, aminocarbonyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsuphonyl, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O which may optionally be attached via a nitrogen atom, and/or cyano,
a 3- to 8-membered saturated or unsaturated non-aromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom and which may optionally be substituted by 1 to 3 substituents selected from the group consisting of oxo, halogen, hydroxyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkyl and hydroxy-(C 1 -C 6 )-alkyl,
(C 2 -C 6 )-alkenyl
and groups of the formulae
—OR 19 ,
—NR 20 R 21 or —CO—NR 22 R 23 ,
carbazole, dibenzofuran or dibenzothiophene,
xanthene or 9,10-dihydroacridine,
in which R 19 is phenyl which for its part is optionally substituted by a group of the formula —NR 24 R 25
in which
R 24 and R 25 are identical or different and represent hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-acyl, or
R 19 represents (C 1 -C 6 )-alkyl which is optionally mono- to trisubstituted by hydroxyl and/or halogen,
R 20 and R 21 are identical or different and represent hydrogen, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, phenyl, (C 1 -C 6 )-acyl or (C 1 -C 6 )-alkyl,
where abovementioned (C 1 -C 6 )-alkyl is optionally substituted by (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-acyl, by phenyl or by a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O,
where abovementioned phenyl and abovementioned aromatic heterocycle are optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and hydroxyl, and
R 22 and R 23 are identical or different and represent hydrogen or (C 1 -C 6 )-alkyl,
and R 7 may have the meaning of R 5 and may be identical to or different from R 5 ,
and their salts.
2. Compounds of the general formula (I) according to claim 1 :
in which
R 1 represents hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, amino-(C 1 -C 6 )-alkyl or halogeno-(C 1 -C 6 )-alkyl,
R 2 and R 3 are identical or different and represent hydrogen, (C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkyl or biphenylaminocarbonyl, or
represent (C 1 -C 6 )-alkyl which is optionally substituted by 1 to 3 substituents selected from the group consisting of (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy, halogen, hydroxyl, amino, radicals of the formula
a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, where a nitrogen-containing heterocycle may also be attached via the nitrogen atom, a 3- to 8-membered saturated or unsaturated nonaromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and (C 6 -C 10 )-aryl, which for its part may be substituted by hydroxyl or (C 1 -C 6 )-alkoxy, or
represent a group of the formula
in which R 8 and R 9 are identical to or different from one another and represent hydrogen and (C 1 -C 4 )-alkyl, or
represent a group of the formula
in which R 10 is the side-group of a naturally occurring α-amino acid, or
represent a group of the formula
in which R 11 represents (C 1 -C 4 )-alkyl and R 12 represents hydrogen, (C 1 -C 4 )-alkyl or represents a group of the formula
in which R 10′ is the side-group of a naturally occurring α-amino acid, or
R 2 and R 3 together with the nitrogen atom form a 5- or 6-membered saturated heterocycle which may optionally contain an oxygen atom,
R 4 represents hydrogen, (C 1 -C 6 )-acyl, (C 2 -C 6 )-alkenyl, (C 3 -C 8 )-cycloalkyl, or
R 4 represents (C 1 -C 6 )-alkyl which may optionally be substituted by 1 to 3 substituents selected from the group consisting of halogen, hydroxyl, (C 1 -C 6 )-acyl, (C 1 -C 6 )alkoxy, —(OCH 2 CH 2 ) n OCH 2 CH 3 , in which n is 0 or 1, phenoxy, (C 6 -C 10 )-aryl and —NR 3 R 14 ,
in which R 13 and R 14 are identical or different and represent hydrogen, (C 1 -C 6 )-acyl, (C 1 -C 6 )-alkyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylamino-(C 1 -C 6 )-alkyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, (C 6 -C 10 )-aryl or (C 1 -C 6 )-alkoxycarbonyl, or
R 13 and R 14 together with the nitrogen atom form a 5- or 6-membered saturated heterocycle which may optionally contain a further heteroatom from the group consisting of S and O or a radical of the formula —NR 15 and which may be substituted by oxo,
in which R 15 represents hydrogen or (C 1 -C 4 )-alkyl, or
R 4 represents (C 1 -C 6 )-alkyl which is substituted by a 5- or 6-membered aromatic, optionally benzo-fused heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, where a nitrogen-containing heterocycle may also be attached via the nitrogen atom, or which is substituted by
radicals of the formulae
in which
R 16 represents hydrogen or (C 1 -C 6 )-alkyl,
R 17 and R 18 are identical or different and represent hydrogen, (C 1 -C 6 )-alkyl or (C 6 -C 10 )-aryl, where abovementioned (C 1 -C 6 )-alkyl and (C 6 -C 10 )-aryl may optionally be substituted by 1 to 3 substituents selected from the group consisting of hydroxyl, (C 1 -C 6 )-alkoxy and halogen,
R 5 represents hydrogen, (C 1 -C 6 )-alkyl, halogen, amino, mono- or di-(C 1 -C 6 )-alkylamino or represents (C 1 -C 6 )-alkanoylamino,
R 6 represents phenyl which may optionally be substituted by one to three substituents selected from the group consisting of
halogen,
(C 6 -C 10 )-aryl which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogeno-(C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkoxy, amino, (C 1 -C6)-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsulphonyl, tri-(C 1 -C 6 )-alkylsilyloxy, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and/or cyano,
(C 1 -C 6 )-alkoxy,
(C 1 -C 6 )-alkoxycarbonyl,
(C 1 -C 6 )-alkylthio,
hydroxyl,
carboxyl,
partially fluorinated (C 1 -C 6 )-alkoxy having up to 6 fluorine atoms,
(C 1 -C 6 )-alkyl which is optionally substituted by a radical of the formula
a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O which may optionally be attached via a nitrogen atom and which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogeno-(C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkoxy, amino, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsuphonyl, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O which may optionally be attached via a nitrogen atom, and/or cyano,
a 3- to 8-membered saturated- or unsaturated non-aromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom and which may optionally be substituted by 1 to 3 substituents selected from the group consisting of oxo, halogen, hydroxyl, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkyl and hydroxy-(C 1 -C 6 )-alkyl,
(C 2 -C 6 )-alkenyl
and groups of the formulae
—OR 19 ,
—NR 20 R 21 or —CO—NR 22 R 23 ,
in which R 19 is phenyl which for its part is optionally substituted by a group of the formula —NR 24 R 25 ,
in which
R 24 and R 25 are identical or different and represent hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-acyl,
or
R 19 represents (C 1 -C 6 )-alkyl which is optionally mono- to trisubstituted by hydroxyl and/or halogen,
R 20 and R 21 are identical or different and represent hydrogen, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, phenyl, (C 1 -C 6 )-acyl or (C 1 -C 6 )-alkyl, where abovementioned (C 1 -C 6 )-alkyl is optionally substituted by (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-acyl, by phenyl or by a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, where abovementioned phenyl and abovementioned aromatic heterocycle are optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and hydroxyl, and
R 22 and R 23 are identical or different and represent hydrogen or (C 1 -C 6 )-alkyl,
and R 7 may have the meaning of R 5 and may be identical to or different from R 5 ,
and their salts.
3. Compounds of the general formula (I) according to claim 1 or 2 , in which R 1 represents hydrogen or (C 1 -C 6 )-alkyl.
4. Compounds of the general formula (I) according to claim 1 , in which R 2 and R 3 each independently represent hydrogen or (C 1 -C 6 )-alkyl.
5. Compounds of the general formula (I) according to claim 1 ,in which R 4 represents hydrogen or (C 1 -C 6 )-alkyl.
6. Compounds of the general formula (I) according to claim 1 , in which R 5 represents hydrogen.
7. Compounds of the general formula (I) according to claim 1 , in which
R 6 represents phenyl which may optionally be substituted by one to three substituents selected from the group consisting of
halogen,
(C 6 -C 10 )-aryl which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogeno-(C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkoxy, amino, hydroxyl, mono- or di-(C 1 -C 6 )-alkylamino, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, and/or cyano, and
a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom.
8. Compounds according to claim 1 having the following formula:
in which R 1 , R 2 , R 3 , R 4 , R 5 and R 7 are each as defined in claim 1 ,
R 26 and R 27 are identical or different and represent hydrogen, halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, partially fluorinated (C 1 -C 6 )-alkoxy having up to 6 fluorine atoms, (C 1 -C 6 )-alkyl, a group of the formulae —OR 9 , —NR 20 R 21 or —CO—N R 22 R 23 , in which
R 19 represents phenyl which for its part is optionally substituted by a group of the formula —NR 24 R 25 , in which R 24 and R 25 are identical or different and represent hydrogen, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-acyl, or
R 19 represents (C 1 -C 6 )-alkyl which is optionally mono- to trisubstituted by hydroxyl and/or halogen,
R 20 and R 21 are identical or different and represent hydrogen, carbamoyl, mono- or d i-(C 1 -C 6 )-alkylaminocarbonyl, phenyl, (C 1 -C 6 )-acyl or (C 1 -C 6 )-alkyl,
where abovementioned (C 1 -C 6 )-alkyl is optionally substituted by (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-acyl, phenyl or by a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O,
where abovementioned phenyl and abovementioned aromatic heterocycle are optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and hydroxyl, and
R 22 and R 23 are identical or different and represent hydrogen or (C 1 -C 6 )-alkyl,
R 28 represents (C 6 -C 10 )-aryl, which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogen-(C 1 -C 6 )-alkyl, halogen-(C 1 -C 6 )-alkoxy, amino, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsulphonyl, tri-(C 1 -C 6 )-alkylsilyloxy, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and/or cyano, or
R 28 represents a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom and which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogeno-(C 1 -C 6 )-alkyl, halogeno-(C 1 -C 6 )-alkoxy, amino, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsulphonyl, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and/or cyano,
and their salts.
9. Compound according to claim 1 of the formula:
and pharmaceutically acceptable salts thereof.
10. Compound according to claim 1 of the formula:
and pharmaceutically acceptable salts thereof.
11. Compound according to claim 1 of the formula:
and pharmaceutically acceptable salts thereof.
12. Compound according to claim 1 of the formula:
13. Compound according to claim 1 of the formula:
14. Compounds of the general formula (IV)
in which R 1 , R 4 , R 5 , R 6 and R 7 are each as defined in claim 1 and D is a halogen atom.
15. Process for preparing the compounds of the general formula (I) according to claim 1 , characterized in that
[A] compounds of the general formula (II)
in which
R 1 , R 2 , R 3 and R 4 are each as defined in claim 1 ,
are reacted with compounds of the general formula (III)
in which
A represents a leaving group and
R 5 , R 6 and R 7 are each as defined in claim 1 ,
in inert solvents,
or
[B] compounds of the general formula (IV)
in which
R 1 , R 4 , R 5 , R 6 and R 7 are each as defined in claim 1 and D is a halogen atom,
are reacted with amines of the general formula (V),
HNR 2 R 3 (v)
in which R 2 and R 3 are each as defined in claim 1 ,
in inert solvents,
or
[C] compounds of the general formula (X)
in which R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are each as defined in claim 1 ,
R 26 and R 27 are identical or different and represent hydrogen, halogen, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, partially fluorinated (C 1 -C 6 )-alkoxy having up to 6 fluorine atoms, (C 1 -C 6 )-alkyl, a group of the formulae —OR 19 , —NR 20 R 21 or —CO—NR 22 R 23 , in which
R 19 represents phenyl which for its part is optionally substituted by a group of the formula —NR 24 R 25 , in which R 24 and R 25 are identical or different and represent hydrogen (C 1 -C 6 ) or (C 1 -C 6 )-acyl, or
R 19 represents (C 1 -C 6 )-alkyl which is optionally mono- to trisubstituted by hydroxyl and/or halogen,
R 20 and R 21 are identical or different and represent hydrogen, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, phenyl, (C 1 -C 6 )-acyl or (C 1 -C 6 )alkyl, where abovementioned (C 1 -C 6 )-alkyl is optionally substituted by (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-acyl, phenyl or by a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S. N and O,
where abovementioned phenyl and abovementioned aromatic heterocycle are optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and hydroxyl, and
R 22 and R 23 are identical or different and represent hydrogen or (C 1 -C 6 )-alkyl,
and E is trifluoromethanesulphonate or halogen,
are reacted with boronic acids or stannanes of the general formula (Xl):
R 28 M (Xl),
in which
R 28 represents (C 6 -C 10 )-aryl, which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogen-(C 1 -C 6 )-alkyl, halogen-(C 1 -C 6 )-alkoxy, amino, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsulphonyl. tri-(C 1 -C 6 )-alkylsilyloxy, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and/or cyano, or
R 28 represents a 5- or 6-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom and which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C 1 -C 6 )-alkanoyl (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl, halogen, (C 1 -C 6 )-alkoxycarbonyl, nitro, halogeno-(C 1 -C 6 )alkyl, halogeno-(C 1 -C 6 )-alkoxy, amino, (C 1 -C 6 )-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C 1 -C 6 )-alkylaminocarbonyl, mono- or di-(C 1 -C 6 )-alkanoylamino, (C 1 -C 6 )-alkoxycarbonylamino, (C 1 -C 6 )-alkylsulphoxy, (C 1 -C 6 )-alkylsulphonyl, a 3- to 8-membered saturated or unsaturated nonaromatic mono- or bicyclic heterocycle having up to 3 heteroatoms from the group consisting of S, N and O, which may optionally be attached via a nitrogen atom, and/or cyano,
and M is a tri-(C 1 -C 6 )-alkylstannyl group or a boronic acid group, in inert solvents in the presence of palladium catalysts at temperatures of 50-140° C.,
to give compounds of the formula (XIV)
or
[D] compounds of the general formula (XII)
in which R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 26 and R 27 are each as defined above
and M is as defined above,
are reacted with trifluoromethanesulphonates or halides of the general formula (XIII):
R 28 E (XIII),
in which R 28 is as defined above
and E is as defined above
in inert solvents in the presence of palladium catalysts at temperatures of 50-140° C.,
to give compounds of the formula (XIV).
16. Pharmaceutical composition, comprising a compound of the general formula (I) according to claim 1 in a mixture with a pharmaceutically acceptable carrier or excipient.
17. A method of treating viral infection, comprising administering to a human or animal an effective amount of a compound of the general formula (I) according to claim 1 .
18. The method of claim 17 , wherein said viral infection is caused by herpes viruses.
19. The method of claim 17 , wherein said viral infection is caused by Herpes simplex viruses.