Inverse thiazolylamide derivatives
OwnerMartin Hendrix, Gerald Kleymann +11inventors
InventorsMartin Hendrix, Gerald Kleymann, Ulrich Betz, Judith Baumeister, Wolfgang Bender, Peter Eckenberg, Rudiger Fischer, Gabriele Handke, Kerstin Henninger, Axel Jensen, Jorg Keldenich, Udo Schneider, Olaf Weber
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Abstract
The present invention relates to novel compounds, i.e. inverse thiazolylamide derivatives, to processes for their preparation and to their use as medicaments, in particular as antiviral medicaments.
Claims23
Compounds of the general formula (I):
- 30
- in which
- R1 represents hydrogen, halogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, amino-(C1-C6)-alkyl or halogeno-(C1-C6)-alkyl,
- R2 and R3 are identical or different and represent hydrogen or represent (C1-C6)-alkyl which is optionally substituted by 1 to 3 substituents selected from the group consisting of (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, halogen, hydroxyl, amino and (C6-C10)-aryl which for its part may be substituted by hydroxyl or (C1-C6)-alkoxy, or
- R2 and R3 together with the nitrogen atom form a 5- or 6-membered saturated heterocycle which may optionally also contain an oxygen atom,
- R4 represents hydrogen, (C1-C6)-acyl, (C2-C6)-alkenyl, (C3-C8)-cycloalkyl or (C1-C6)-alkoxycarbonyl, or
- R4 represents (C1-C6)-alkyl which may optionally be substituted by 1 to 3 substituents selected from the group consisting of halogen, hydroxyl, (C1-C6)-acyl, (C1-C6)-alkoxy, —(OCH2CH2)nOCH2CH3, where n is 0 or 1, phenoxy, (C6-C10)-aryl and —NR13R14,
- where
- R13 and R14 are identical or different and represent hydrogen, (C1-C6)-acyl, (C1-C6)-alkyl, carbamoyl, mono- or di-(C1-C6)-alkylamino-(C1-C6)alkyl, mono- or di-(C1-C6)-alkyl-aminocarbonyl, (C6-C10)-aryl or (C1-C6)-alkoxycarbonyl, or
- R13 and R14 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 —NR15 and which may be substituted by oxo,
- where
- R15 represents hydrogen or (C1-C4)-alkyl,
- R5 represents no substituent, hydrogen, (C1-C6)-alkyl or (C1-C6)-alkanoyl,
- R6 represents phenyl which may optionally be substituted by one to three substituents selected from the group consisting of
- halogen,
- (C6-C10)-aryl which may optionally be substituted by 1 to 3 substituents selected from the group consisting of (C1-C6)-alkanoyl, (C1-C6)-alkoxy, (C -C6)-alkyl, halogen, (C -C6)-alkoxycarbonyl, nitro, halogeno-(C1-C6)-alkyl, halogeno-(C1-C6)-alkoxy, amino, (C1-C6)-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C1-C6)-alkylaminocarbonyl, mono- or di-(C1-C6)-alkanoylamino, (C1-C6)-alkoxycarbonylamino, (C1-C6)-alkylsulphoxy, (C1-C6)-alkylsulphonyl, tri-(C1-C6)-alkylsilyloxy, 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 is optionally attached via a nitrogen atom, and cyano,
- (C1-C6)-alkoxycarbonyl,
- (C1-C6)-alkylthio,
- hydroxyl,
- carboxyl,
- partially fluorinated (C1-C6)-alkoxy having up to 6 fluorine atoms,
- (C1-C6)-alkyl which may optionally be substituted by a radical of the formula
- 31
- an aromatic heterocycle having up to 3 hetero atoms from the group consisting of S, N and O, which is optionally attached via a nitrogen atom and may optionally be substituted by 1to 3 substituents selected from the group consisting of (C1-C6)-alkanoyl, (C1-C6)-alkoxy, (C1-C6)-alkyl, halogen, (C1-C6)-alkoxycarbonyl, nitro, halogeno-(C1-C6)-alkyl, halogeno-(C1-C6)-alkoxy, amino, (C1-C6)-alkylthio, hydroxyl, carboxyl, carbamoyl, mono- or di-(C1-C6)-alkylaminocarbonyl, mono-or di-(C1-C6)-alkanoylamino, (C1-C6)-alkoxycarbonyl amino, (C1-C6)-alkylsulphoxy, (C1-C6)-alkylsulphonyl, 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 is optionally attached via a nitrogen atom, and 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 is optionally 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, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkoxycarbonylamino, (C1-C6)-alkyl, halogeno-(C1-C6)-alkyl and hydroxy-(C1-C6)-alkyl,
- and groups of the formulae
- —OR19,
- —NR20R21 or —CO—NR22R23,
- in which
- R19 is phenyl which for its part is optionally substituted by a group of the formula —NR24R25,
- in which
- R24 and R25 are identical or different and represent hydrogen, (C1-C6)-alkyl or (C1-C6)-acyl,
- or
- R19 represents (C1-C6)-alkyl which is optionally mono- to trisubstituted by hydroxyl and/or halogen,
- R20 and R 21 are identical or different and hydrogen, carbamoyl, mono- or di-(C1-C6)-alkylaminocarbonyl, phenyl, (C1-C6)-acyl or (C1-C6)-alkyl, where the (C1-C6)-alkyl mentioned above is optionally substituted by (C1-C6)-alkoxy, (C1-C6)-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 the phenyl mentioned above and the aromatic heterocycle mentioned above are optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and hydroxyl, and
- R22 and R23 are identical or different and represent hydrogen or (C1-C6)-alkyl,
- R7 represents hydrogen, (C1-C6)-alkyl or (C1-C6)-alkanoyl,
- R8 represents no substituent, hydrogen or (C1-C6)-alkyl, and
- represents a single or double bond,
- and their salts.
Use of [5-(aminosulphonyl)-1,3-thiazol-2-yl]propanamide derivatives for preparing medicaments.
Use of [5-(aminosulphonyl)-1,3-thiazol-2-yl]acetamide derivatives for preparing medicaments.
Compounds of the general formula (X)
- 43
- in which
- R1, R2, R3 and R26 are as defined above.
Dependencies are inferred from the claim text.