Tetra- and pentasubstituted benzimidazolium compounds useful in the treatment of respiratory diseases

A compound of formula (I), or a tautomers thereof or a pharmacologically acceptable acid addition salt of the compound or the tautomer,

• wherein
• R1 and R2 are independently selected from a substituent of formula —CH2—C(O)—R5,
• wherein R6 is selected from di(C1-C2-alkyl)amino or from a 5- to 7-membered heterocycle containing 1 or 2 heteroatoms selected from O and N, wherein the 5- to 7-membered heterocycle may carry one substituent selected from C1-C2-alkyl;
• and/or wherein R1 and R2 are independently selected from a group of formula (A),
• wherein Ra is selected from C1-C3-alkyl, C1-C2-alkoxy-C2-C3-alkyl-, hydroxy-C2-C3-alkyl-, and amino-C2-C3-alkyl-, and wherein * denotes the point of attachment;
• and/or R1 and R2 are independently selected from C1-C4-alkyl, 2-(2-hydroxyethyloxy)-ethyl, tetrahydrofur-2-ylmethyl, tetrahydropyran-4-ylmethyl, pyridine-3-ylmethyl,
• wherein
• denotes the point of attachment;
• R3 and R4 are independently selected from H, OH, Cl, —O—CH2—COOH,
• wherein
• denotes the point of attachment,
• and/or wherein R3 and R4 are independently selected from a substituent of formula —O—CH2—C(O)NRbRc, wherein
• Rb is H, methyl, ethyl, benzyl, hydroxyethyl, or hydroxypropyl, and
• Rc is selected from methyl, piperidin-4-yl, pyrid-2-ylmethyl, 1-(C1-C6-alkyl)-piperidin-4-yl, 3-hydroxy-pyridin-5-yl, 3-hydroxy-6-methylpyridin-2-ylmethyl and 3-hydroxy-pyridin-2-ylmethyl, or wherein
• Rb and Rc together with the nitrogen atom they are attached to form a group selected from 3,4-dihydroxypyrrolidin-1-yl, thiomorpholin-4-yl-S-oxide, 1-(3-hydroxy-6-methylpyridin-2-ylmethyl)piperazin-4-yl and 1-(benzyloxycarbonyl)piperazin-4-yl;
• X is Cl or Br;
• and
• Z− is chloride, bromide, iodide, hydroxide, hydrogensulfate, sulfate, nitrate, phosphate, formate, acetate, trifluoroacetate, fumarate, citrate, tartrate, oxalate, succinate, mandelate, methanesulfonate or p-toluenesulfonate;
• or
• Z− may be absent if the remaining compound of formula (I) carries at least one negatively charged substituent R3 or R4;
• provided that at least one of R1 and R2 is different from C1-C4-alkyl and 2-(2-hydroxyethyloxy)ethyl, and
• provided that at least one of R3 and R4 is different from H and Cl, and
• provided that if both substituents R3 and R4 are selected from H, OH, Cl, —O—CH2—CH2OH, —O—CH2—P(O)(CH3)2, —O—CH2—C(O)—NH(C1-C2-alkyl), —O—CH2—C(O)—N(C1-C2-alkyl)2, and
• at least one of the substituents R1 and R2 is different from C1-C4-alkyl and tetrahydropyran-4-ylmethyl.