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US 7,582,660 B2Granted
2-thio-substituted imidazole derivatives and their use in pharmaceutics
Assigneec-a-i-r biosciences GmbH
InventorsStefan Laufer, Hans-Günter Striegel, Karola Tollmann, Wolfgang Albrecht
Life of this patent
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Abstract
The invention relates to 2-thio-substituted imidazole derivatives of the formula I in which the radicals R1, R2, R3 and m are as defined in the description. The compounds according to the invention have immunomodulating and/or cytokine-release-inhibiting action and are therefore suitable for treating disorders associated with a disturbed immune system.
Claims23
A 2-thio-substituted imidazole derivative compound of the formula I
- wherein
- R1 is aryl which may or may not be substituted by a halogen atom;
- R2 is selected from the group consisting of
- a) aryl-C1-C4-alkyl, and
- b) C1-C6-alkyl;
- R3 is selected from the group consisting of
- a) NR4R10
- b) NR7COR10, and
- c) C1-C6-alkoxy;
- R4 is H;
- R10 is
- or, if R3 is NR7COR10, R10 is R8,
- R5 and R6, which may be identical or different, are H, halogen, C1-C6-alkoxy or C1-C6-alkyl;
- R7 is H, C1-C6-alkyl or benzyl;
- R8 is C1-C4-alkyl, C3-C6-cycloalkyl or phenyl, where the phenyl group may have one or two substituents independently of one another selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen;
- A is straight-chain or branched C1-C6-alkylene or C2-C6-alkenylene and
- m is 0, 1 or 2;
- or a tautomer, an optical isomer or a physiologically acceptable salt thereof.
15 more elements
A 2-thio-substituted imidazole derivative compound of the formula I
- wherein
- R1 is aryl which is substituted by a halogen atom or by halo-C1-C6-alkyl;
- R2 is selected from the group consisting of
- a) aryl-C1-C4-alkyl, and
- b) C1-C6-alkyl;
- R3 selected from the group consisting of
- a) NR4R10,
- b) NR7COR10,
- c) OR10, and
- d) NH2;
- R4 is H, —COR14, —CO2R14, —CONH2, —CONHR14, —CHR16—OR14, —CHR16—O—COR14, —COC(R16)2—OH, —COR15, SO2R15 or —SO2R14, R14 is C1-C6-alkyl or CF3, R15 is phenyl or tolyl, and R16 is H or C1-C6-alkyl;
- R5 and R6, which may be identical or different, are H, halogen, C1-C6-alkoxy, C1-C6-alkyl or halo-C1-C6-alkyl;
- R7 is H;
- R10 has one of the meanings below:
- f) C1-C6-alkyl which is substituted by 2 phenyl groups, or
- g) trifluoromethyl;
- A is straight-chain or branched C1-C6-alkylene or C2-C6-alkenylene;
- B is selected from the group consisting of
- e) OC1-C6-alkyl, and
- f) OH;
- Hy is a 3- to 10-membered non-aromatic mono-, bi- or tricyclic carbocycle which may or may not be fused with a benzene ring;
- Ar is a 5- or 6-membered aromatic heterocycle which has 1, 2 or 3 heteroatoms independently of one another selected from the group consisting of O, S and N and which may or may not be fused with a benzene ring;
- Het is a 5- or 6-membered non-aromatic heterocycle which has 1, 2 or 3 heteroatoms independently of one another selected from the group consisting of O, S and N which may or may not be fused with a benzene ring and which may or may not be bridged bicyclically or tricyclically;
- m is 0, 1 or 2;
- or a tautomer, an optical isomer or a physiologically acceptable salt thereof.
22 more elements
Dependencies are inferred from the claim text.