1-alkyl-2-aryl-benzimidazole derivatives, their use for the production of pharmaceutical agents as well as pharmaceutical preparations that contain these derivatives

Benzimidazole derivatives with general formula I:

• in which
• R1 stands for an aryl group, whereby the aryl group can be substituted with up to three radicals, independently of one another, selected from the group consisting of:
• F, Cl, Br, C(NH)NH2, C(NH)NHR4, C(NH)NR4R4′, C(NR4)NH2, C(NR4)NHR4′,
• C(NR4)NR4R4′,
• X—OH, X—OR4, X—OCOR4, X—OCONHR4,X—COR4, X—C(NOH)R4,
• X—CN, X—COOH, X—COOR4, X—CONH2, X—CONR4R4′, X—CONHR4,
• X—CONHOH, X—SR4, X—SOR4, X—SO2R4, SO2NH2,
• SO2NHR4, SO2NR4R4′, NO2, X—NH2, X—NHR4, X—NR4R4′, X—NHSO2R4,
• X—NR4SO2R4′,
• X—NHCOR4, X—NHCOOR4, X—NHCONHR4 and
• R4,
• whereby X is a bond, CH2, (CH2)2 or CH(CH3), and radicals R4 and R4′ are selected independently of one another according to the meanings that are further indicated below,
• whereby two substituents at R1, if they are in ortho-position to one another, are linked to one another in such a way that they jointly form a methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl or butane-1,4-diyl group,
• R2 stands for a radical that is C1-6-alkyl or C3-6-alkenyl,
• whereby the alkyl and alkenyl radicals can be substituted with up to two radicals, selected from the group consisting of C0-2-alkanediyl-OH, C0-2-alkanediyl-OR7, C0-2-alkanediyl-NH2, C0-2-alkanediyl-NHR7, C0-2-alkanediyl-NR7R7′, C0-2-alkanediyl-NHCOR7, C0-2-alkanediyl-NR7COR7′, C0-2-alkanediyl-NHSO2R7, C0-2-alkanediyl-NR7SO2R7′, C0-2-alkanediyl-CO2H, C0-2-alkanediyl-CO2R7, C0-2-alkanediyl-CONH2, C0-2-alkanediyl-CONHR7, C0-2-alkanediyl-CONR7R7′, phenyl and five- and six-membered heteroaryl radicals, whereby the heteroaryl radical contains one or two heteroatoms, selected from the group consisting of N, S and O, and whereby R7 and R7′, independently of one another, in each case stand for R4 or R6, whereby R4 and R6 have the meanings that are indicated below,
• whereby also the phenyl radical and/or the heteroaryl radical can be substituted with up to two radicals, selected from the group consisting of F, Cl, Br, CH3, C2H5, OH, OCH3, OC2H5, NO2, N(CH3)2, CF3, C2F5 and SO2NH2 and/or can also carry an anellated methanediylbisoxy group or an ethane-1,2 diylbisoxy group,
• whereby also an H atom can be exchanged for a heterocyclic radical that is pyrrolidine, such that a bond to a first N atom of the heterocyclic radical is formed, whereby the piperazine radical can be substituted on a second N atom also with R7, COR7 or SO2R7, whereby R7 and R7′, independently of one another, in each case stand for R4 or R6, and whereby R4 and R6 have the meanings that are indicated below,
• R3 stands for one or two substituents, which can be selected independently of one another, selected from the group consisting of:
• hydrogen,
• F, Cl, Br,
• OH, OR4, OCOR4, OCONHR4,
• COR4,
• CN, COOH, COOR4, CONH2, CONHR4, CONR4R4′, CONHOH,
• CONHOR4,
• SR4, SOR4, SO2R4, SO2NH2, SO2NHR4, SO2NR4R4′,
• NO2, NH2, NHR4, NR4R4′,
• NHSO2R4, NR4SO2R4′, NHSO2R6, NR4SO2R6,
• NHCOR4, NHCOOR4, NHCONHR4 and R4,
• whereby R4, R4′ and R6, independently of one another, are selected according to the meanings that are further indicated below,
• A stands for a group that is selected from the group consisting of C1-10-alkanediyl, C2-10-alkenediyl, C2-10-alkinediyl and (C0-3-alkanediyl-C3-7-cycloalkanediyl-C0-3-alkanediyl),
• whereby if the cycloalkyl ring can be five-membered, a ring member in the cycloalkyl ring is a ring-N or a ring-O or if the cycloalkyl ring is six- or seven-membered, one or two ring members in the cycloalkyl ring can be ring-N and/or ring-O atoms in each case, whereby the ring-N atoms can be substituted with C1-3-alkyl or C1-3-alkanoyl,
• whereby also in the aliphatic chains of C1-10-alkanediyl, C2-10-alkenediyl, C2-10-alkinediyl and (C0-3-alkanediyl-C3-7-cycloalkanediyl-C0-3-alkanediyl) groups, a C atom can be exchanged for O, NH, N—C1-3-alkyl or N—C1-3-alkanoyl, whereby at least one of the alkyl groups and/or cycloalkyl groups can be substituted with a radical that is selected from the group consisting of ═O, OH, O—C1-3-alkyl, NH2, NH—C1-3-alkyl, NH—C1-3-alkanoyl, N(C1-3-alkyl)2 and N(C1-3-alkyl)(C1-3-alkanoyl),
• B stands for a radical that is selected from the group consisting of COOH, COOR5, CONH2, CONHNH2, CONHR5, CONR5R5′, CONHOH, CONHOR5 and tetrazolyl,
• whereby B is bonded to a C atom of group A, and
• whereby radicals R5 and R5′ are selected independently of one another and have the meanings that are further indicated below,
• Y stands for a group that is selected from the group consisting of O, NH, NR4, NCOR4, NSO2R4 and NSO2R6,
• whereby R4 and R6 have the meanings that are further indicated below,
• R4 and R4′ in each case stand for a radical that is selected from the consisting of CF3, C2F5, C1-4-alkyl, C2-4-alkenyl, C2-3-alkinyl and (C0-3-alkanediyl-C3-7-cycloalkyl),
• whereby the alkyl radicals can be substituted with a radical that is selected from the group consisting of OH, OCH3 and SCH3,
• and whereby if the cycloalkyl ring is five-membered, a ring member in the cycloalkyl ring can be a ring-N or a ring-O, and if the cycloalkyl ring is six- or seven-membered, one or two ring members in the cycloalkyl ring can be ring-N and/or ring-O atoms in each case, whereby the ring-N atoms can be substituted with C1-3-alkyl or C1-3-alkanoyl,
• R5 and R5′ in each case stand for a radical that is selected from the group consisting of C1-6-alkyl, C2-6-alkenyl and C2-6-alkinyl, whereby a C atom in at least one of the radicals can be exchanged for O, S, SO, SO2, NH, N—C1-3-alkyl or N—C1-3-alkanoyl, also for (C0-3-alkanediyl-C3-7-cycloalkyl), whereby if the cycloalkyl ring is five-membered, a ring member in the cycloalkyl ring can be a ring-N or a ring-O or if the cycloalkyl ring is six- or seven-membered, one or two ring members in the cycloalkyl ring in each case can be ring-N and/or ring-O atoms, whereby the ring-N atoms can be substituted with at least one radical that is selected from the group consisting of C1-3-alkyl and C1-3-alkanoyl, and also stand for (C0-3-alkanediyl-aryl) and (C0-3-alkanediyl-heteroaryl),
• whereby the heteroaryl group is five- or six-membered and can contain one or two heteroatoms, selected from the group consisting of N, S and O,
• whereby at least one of the above-mentioned alkyl and cycloalkyl radicals can be substituted with up to two radicals, selected from the group consisting of CF3, C2F5, OH, O—C1-3-alkyl, NH2, NH—C1-3-alkyl, NH—C1-3-alkanoyl, N(C1-3-alkyl)2, N(C1-3-alkyl)(C1-3-alkanoyl), COOH, CONH2 and COO—C1-3-alkyl, and at least one of the aryl and heteroaryl groups can be substituted with up to two radicals, selected from the group consisting of F, Cl, Br, CH3, C2H5, OH, OCH3, OC2H5, NO2, N(CH3)2, CF3, C2F5 and SO2NH2 and/or at least one of the alkyl, cycloalkyl, aryl and/or heteroaryl radicals can carry an anellated methanediylbisoxy group or ethane-1,2-diylbisoxy group,
• or R5 and R5′ together with the amide-N atom of B form a five- to seven-membered, saturated or unsaturated heterocyclic ring, whereby the heterocyclic ring can contain another N or O or S atom of B, and the heterocyclic ring can be substituted with C1-4-alkyl, (C0-2-alkanediyl-C1-4-alkoxy), C1-4-alkoxycarbonyl, aminocarbonyl and aryl,
• R6 stands for a radical that is selected from the group consisting of (C0-3-alkanediyl-aryl) and (C0-3-alkanediyl-heteroaryl), whereby the heteroaryl group is five- or six-membered and contains one or two heteroatoms, selected from the group consisting of N, S and O,
• whereby at least one of the aryl and heteroaryl groups can be substituted with up to two radicals in each case, selected from the group consisting of F, Cl, Br, CH3, C2H5, OH, OCH3, OC2H5, NO2, N(CH3)2, CF3, C2F5, and SO2NH2 and/or at least one of the aryl or heteroaryl groups can also carry an anellated methanediylbisoxy group or ethane-1,2-diylbisoxy group.