2-thio-substituted imidazole derivatives and their use in pharmaceutics

A 2-thio-substituted imidazole derivative of the formula I

• in which
• R1 is H or C1-C6-alkyl;
• R2 is selected from the group consisting of:
• a) C1-C6-alkyl which is substituted by 2 or 3 hydroxyl groups, halogen atoms, NR5R6 or C1-C4-alkoxy groups, where R5 is H, C1-C6-alkyl, phenyl-C1-C4-alkyl or phenyl and R6 is H or C1-C6-alkyl,
• b) C1-C6-alkyl which is substituted by 1, 2 or 3 radicals of the formula —COOR5, where R5 is H, C1-C6-alkyl, phenyl-C1-C4-alkyl or phenyl,
• c) C1-C6-alkyl which is substituted by at least one radical of the formula —COOR5 and at least one hydroxyl group, where R5 is H, C1-C6-alkyl, phenyl-C1-C4-alkyl or phenyl,
• d) a radical of the formula II
• in which X is O or NR6, m is 1 or 2 and R6 is H or C1-C6-alkyl,
• e) a radical of the formula
• —(CH2)n—CO—R7
• in which R7 is C1-C3-alkyl, phenyl, benzyl or phenethyl and n is 1, 2 or 3,
• f) a radical of the formula
• —(CH2)n—CO—CH2—CO—R7
• in which R7 is C1-C3-alkyl, phenyl, benzyl or phenethyl and n is 1, 2 or 3,
• g) a radical of the formula
• in which the radicals R7, which are identical or different, are C1-C3-alkyl, phenyl, benzyl or phenethyl,
• h) a radical of the formulae
• —(CH2)n—CO—CHOH—R7
• —(CH2)n—CHOH—CO—R7
• —(CH2)n—CO—CH2—CHOH—R7
• —(CH2)n—CHOH—CH2—CO—R7
• in which R7 is C1-C3-alkyl, phenyl, benzyl or phenethyl and n is 1, 2 or 3,
• i) a radical of the formulae
• —(CH2)n—CO—CH2—COOR5
• —CH(COR7)—COOR5
• —(CH2)n—COCOOR5
• in which R5 is H, C1-C6-alkyl, phenyl-C1-C4-alkyl or phenyl, R7 is C1-C3-lkyl, phenyl, benzyl or phenethyl and n is 1, 2 or 3,
• j) a radical of the formula
• —(CH2)n—CONR8R9
• in which R8 and R9, which may be identical or different, are H, C1-C6-alkyl, C1-C6-alkyl, C1-C6-alkyl which is substituted by one, two or three hydroxyl groups, C1-C6-alkyl which is substituted by a COOH group, phenyl or benzyl, or R8 and R9 together with the nitrogen atom to which they are attached are a saturated heterocycle which has 5 or 6 ring atoms and one or two heteroatoms independently of one another selected from the group consisting of N, O and S and which may be substituted by one or two groups independently of one another selected from the group consisting of C1-C6-alkyl and hydroxyl, and n is 1, 2 or 3,
• k) a radical of the formula —(CH2)nCONR10—CONR8R9
• in which R8 and R9, which may be identical or different, are H, C1-C6-alkyl, C1-C6-alkyl which is substituted by one or two hydroxyl groups, C1-C6-alkyl which is substituted by a COOH group, phenyl or benzyl or R8 and R9 together with the nitrogen atom to which they are attached are saturated heterocycle which has 5 or 6 ring atoms and one or two heteroatoms independently of one another selected from the group consisting of N, O, and S, and n is 1, 2 or 3 and R10 is H or C1-C6-alkyl,
• l) C2-C6-alkenyl which is substituted by one or two groups of the formula —COOR5, where R5 is H, C1-C6-alkyl, phenyl or benzyl,
• m) C1-C6-alkyl which is substituted by a non-aromatic 3- to 6-memberedn heterocyclic radical which has one or two heteroatoms independently of one another selected from the group consisting of N and O,
• p is 0, 1 or 2;
• one of the radicals R3 and R4 represents 4-pyridyl, which may have 1 or 2 substituents independently of one another selected from the group consisting of amino, C1-C4-alkylamino, di-C1-C4-alkylamino, phenyl-C1-C4-alkylamino and —NR12COR11, where R11 is C1-C4-alkyl, phenyl which may have one or two substituents independently of one another selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen, and R12 is H, C1-C4-alkyl or benzyl,
• and the second of the radicals R3 and R4 is aryl,
• or an optical isomer or physiologically acceptable salt thereof.