NO326408B1 - Benzimidazoles, pharmaceutical preparations and their use in the manufacture of a medicament for the treatment of diseases associated with microglia activation - Google Patents

Abstract

The invention relates to 1,2-diaryl benzimidazoles of general formula (I) and to the use of benzimidazole derivatives for producing medicaments utilized for the treatment and prophylaxis of illnesses that are associated with a microglia activation.

Description

The invention relates to new benzimidazole derivatives and the use of benzimidazole derivatives for the production of pharmaceuticals for the treatment and prophylaxis of diseases which are associated with microglial activation.

Almost all degenerative diseases of the central nervous system are associated with chronic inflammation. A central step in the development of inflammation is the activation of mononuclear phagocytic cells, the microglia. This takes place, for example, in Alzheimer's disease due to senile plaque, in Creutzfeldt-Jakob disease due to a prion protein and in ischemic stroke due to dead cells. The microglia can remain in an activated state for a long period of time during which they produce and secrete. various inflammatory factors, e.g. reactive oxygen/nitrogen intermediates, proteases, cytokines, complement factors and neurotoxins. These in turn cause neuronal dysfunction and degeneration.

For a possible treatment of neuroinflammation, non-steroidal anti-inflammatory drugs (COX II inhibitors) have been described heretofore (McGeer, P.L., Roger, Neurology 42, 447-449 (1992), Rogers, J., Kirby, L.C., Hempleman, S.R., Berry, D.L., McGeer, P.L., Kaszniak, A.W., Zalinski, J., Cofield, M., Mansukhani, L., Wilson, P., Kogan, F., Neurology 43, 1609-1611 (1993), Andersen, K ., Launer, L.J., Ott, A., Hoes, A.W., Breteler, M.M.B., Hofman, A., Neurology 45, 1441-1445 (1995), Breitner, J.C.S., Gau, B.A., Welsh, KA, Plassman, B.L., McDonald, W.M., Helms, M.J., Anthony, J.C., Neurology 44, 227-232 (1994), The Canadian Study of Health and Aging, Neurology 44, 2073-2079 (1994)), The Cytokine Modulator (McGeer, P.L., McGeer , E.G., Brain Res. Rev. 21:195-218 (1995), McGeer, E.G., McGeer, P.L., CNS Drugs 7, 214-228 (1997), Barone, F.C. and Feuerstein, G.Z., J. Cerebral Blood Flow and Metabolism 19, 819-834 (1999) and the Complement Cascade Inhibitor (Chen.,

S., Frederickson, R.C.A., and Brunden, K.R., Neurobiol. Aging

(1996), McGeer, E.G., McGeer, P.L., Drugs 55:739-746 (1998)). These substances inhibit the synthesis or action of certain inflammatory factors. However, it would have been desirable to have substances that inhibit an earlier step in the development of inflammation and thus prevent the formation or action of many inflammatory factors.

The invention relates to benzimidazoles which are characterized by the general formula:

in which

R<1> means a phenyl, naphthyl, fluorenyl, indanyl, pyridyl, thienyl, furyl, indolyl or benzothienyl group which may be substituted with up to three of the following substituents independently of each other: F, Cl, Br, I, XOH, XOR<4>, XCN, XSR<4>, N02, XNH2, XNHR<4>, XNR4R4', R4, whereby two substituents on R<1>, if they are in the ortho position to each other, can be so connected to each other that together they form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl,

R2 has the same meaning as R<1>,

R3 means one or two substituents which can independently be: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, N02, XNH2, XNHR<4>, XNR<4>R4', XNHS02R< 4> or R<4>,

R4 and R<4>' independently mean C1-4-perfluoroalkyl, C1-6-alkyl, phenyl or phenyl-C1-C4-alkyl, whereby the phenyl groups can be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3 or C2FS,

R5 and R<5>' independently mean C1-6-alkyl, whereby a carbon atom can be exchanged for 0, S, SO, SO2, NH, NCi_3-alkyl or NCi_3-alkanoyl, C3-7-cycloalkyl-C0-3- alkyl, whereby in a 5-membered cycloalkyl ring a ring member can be an N or an 0

and in a 6- or 7-membered cycloalkyl ring, one or two ring members may be N and/or 0, whereby ring nitrogens may optionally be substituted with Ci_3-alkyl or Ci-3-alkanoyl, phenyl, phenyl-Ci~C4-alkyl, pyridyl , pyridyl-Ci-C4-alkyl or imidazolyl-Ci-C4-alkyl,

whereby all previously mentioned alkyl residues can be substituted with up to two substituents of OH, 0Ci-3-alkyl, NH2, NHCi-3-alkyl, NHCi_3-alkanoyl, N (Ci-3-alkyl) 2, N (Ci-3-alkyl ) (Cx-3-alkanoyl), COOH, C0NH2, C00Ci_3-alkyl and all previously mentioned phenyl and pyridyl groups can be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2Hs, N02, 0CH3, OC2H5, CF3, C2F5,

or R<5> and R<5>' together with the nitrogen atom form a 7-pyrrolidine, morpholine, piperidine or piperazine ring and may be substituted with C1-4-alkyl, C1-4-alkyl-C0-2-alkyl, C1-4 -Alkoxycarbonyl or aminocarbonyl,

A means C1-10-alkanediyl or C2-10-alkenediyl,

B stands for COOH, COOR<5>, C0NH2, C0NHNH2, CONHR<5>, CONR<5>R5', CONHOH, CONHOR<5>, S02NH2, S02NHR<5>, S02NR<5>R<5>',

X means a bond,

Y means 0, NH, NR<4>, NS02R<4>,

whereby the following compounds are excluded: [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid methyl ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester, 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester , ■

6-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(4-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[[1-[4-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[[1-[4-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

6- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[[1-[3-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[[1-[3-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester.

The physiologically tolerable salts can be formed with inorganic and organic acids, such as e.g. oxalic acid, lactic acid, citric acid, fumaric acid, acetic acid, maleic acid, tartaric acid, phosphoric acid, HC1, HBr, sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid. For the formation of salts of acid groups, the inorganic or organic bases which are known for the formation of physiologically tolerable salts are also suitable, such as e.g. alkali hydroxides, sodium or potassium hydroxide, alkaline earth hydroxides such as calcium hydroxide, ammonia, amines such as ethanolamine, diethanolamine, triethanolamine, N-methylglucamine, tris-(hydroxymethyl)methylamine.

Particularly preferred are the following benzimidazoles: [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid isopropyl ester, 3- [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester, 2 -[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester, 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid isopropyl ester,

5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid isopropyl ester,

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester, 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester,

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide, N-methoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide, N- (phenylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide,

N-hydroxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide, 7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid methyl ester, 6- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester

6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-t[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester,

6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid isopropyl ester,

6-[[1-(3-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid,

6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[1-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl)oxy]hexane acid methyl ester,

6-[(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester,

6-[[5-[[(4-bromophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

6-t[5-[[(4Tchlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-t[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

6-[[1,2-diphenyl-5-[[(3-methylphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

6-[[1,2-diphenyl-5-[[(4-methylphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

6-[[1,2-diphenyl-5-[[(4-methoxyphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

6-[[1,2-diphenyl-5-[[[(4-trifluoromethyl)phenyl]sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[5-[[[4- (acetylamino)phenyl]sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[5-[[bis-(3-chlorophenyl)sulfonyl]amino]-1, 2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

6-[[1,2-diphenyl-5-[(propylsulfonyl)amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

6-[[5-[(benzylsulfonyl)amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

2-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid methyl ester,

3-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]propanoic acid methyl ester,

6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid ethyl ester,

6-[ [4-acetyl-1-(4-methylphenyl)-2-phenyl-1-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexane acid methyl ester,

6-[[2-phenyl-1-[4-(thiomethyl)phenyl]-1H-benzimidazol-5-yl]oxy]-hexanoic acid methyl ester,

6-[[2-phenyl-1-[(4-thiomethyl)phenyl]-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-5-yl]oxy]hexane acid methyl ester,

6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid methyl ester, N-(phenylmethoxy)-6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H- benzimidazol-6-yl]oxy]hexanamide,

N,N-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide,

N-isopropyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide,

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-pyrrolidin-1-ylhexan-1-one,

5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

6- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[4-(acetyloxy)-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[4-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[4-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[7-methyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester.

Particularly preferred are

6-[[2-phenyl-1-(3-pyridyl)-1H-benzimidazol-5-yl]oxy]hexane acid methyl ester,

6-[[2-phenyl-1-(3-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[2-phenyl-1-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[2-(4-fluorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-Methoxyphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-bromophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-[4-(trifluoromethyl)phenyl]-1-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid,

6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester benzimidazol-6-yl] oxy]hexanoic acid methyl ester,

6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[ 5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-(4-methoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

4- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester,

5- [[5-[h. (4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

6- [[5-[[(4-(trifluoromethyl)phenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-t[5 -[[(4-chlorophenyl)sulfonyl]methylamino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-(indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid, 6-[[1-(3-fluorophenyl)-2-phenyl-1H-benzimidazol- 6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-phenyl-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

N-(cyclopropylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)-. oxy]hexanamide,

N-isobutoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide,

N-(cyclopropylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide,

N-isobutoxy-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide,

N-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide,

N-(3-methoxypropyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide,

N-isobutyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide, 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-morpholine -1-yl-hexan-1-one, N,N-di-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)-oxy]hexanamide, N-isopentyl- 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide, N-(pyridin-2-yl)-6-[(1,2-diphenyl-1H-benzimidazol-6- yl)oxy]-hexanamide, N-(pyridin-3-yl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide, N-isopropyl-6-[[1- (3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N,N-dimethyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H- benzimidazol-6-yl]oxy]hexanamide, N,N-diethyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-isobutyl- 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-cyclopropyl-6-[[1-(3,4-dimethylphenyl)-2- phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-cyclobutyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N- tert-butyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]he xanamide,

(R)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-1-(2-methoxymethyl)pyrrolidin-1-ylhexan-1-one,

N-(3-imidazol-1-ylpropyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide,

N-(2-pyridin-2-ylethyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide,

N-(3-methoxypropyl)-6-[fl-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]heptanamide,

6-[[1-(4-methylphenyl)-2-(3-pyridyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-(2-thienyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[2-(3-indolyl)-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-(2-furyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-(3-furyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-(5-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[1-(4-methylphenyl)-2-(3-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

The benzimidazole derivatives according to the invention inhibit the activation of microglia and can therefore be used for the production of a drug for the treatment or prevention of diseases that are associated with a microglia. With microglia here the brain's

macrophages are understood.

This action is surprising as benzimidazole derivatives have so far only been described for the treatment of thrombosis and arterio-sclerosis (EP0531883, WO 95/07263, EP0104727, WO 97/12613), cystitis (WO 97/33873) and diseases associated with an amyloid peptide (US 5,552,426) and an enhanced activation of Ca channels (EP520200), but an effect on microglia is not known.

The invention also relates to the use of a benzimidazole with the general formula II

in which

R<1> means a phenyl, naphthyl, fluorenyl, indanyl, pyridyl, thienyl, furyl, indolyl or benzothienyl group which may be substituted with up to three of the following substituents

..independently of each other:

F, Cl, Br, I, XOH, XOR<4>, XCN, XSR<4>, N02, XNH2, XNHR<4>, XNR4R4', R4, whereby two substituents on R<1>, if they are in the ortho position to each other, can be so connected to each other that together they form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl,

R2 has the same meaning as R<1>,

R3 means one or two substituents which can independently be: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, NO2, XNH2, XNHR<4>, XNR<4>R<4>' , XNHS02R4 or R<4>,

R.<4>.,and R<4>' independently mean C1-4-perfluoro-alkyl, C1-6-alkyl, phenyl or phenyl-C1-C4-alkyl, whereby the phenyl groups can be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2H5, NO2, 0CH3, OC2H5, CF3 or C2F5,

R<5> and R<5>' independently mean C1-6-alkyl, whereby a carbon atom can be exchanged for 0, S, SO, SO2, NH, NC1-3-alkyl or NC1-3-alkanoyl, C3-7-cycloalkyl -C0-3-alkyl, whereby in a 5-membered cycloalkyl ring one ring member can be an N or an 0 and in a 6- or 7-membered cycloalkyl ring one or two ring members can be N and/or 0, whereby ring nitrogens can optionally be substituted with C1-3-alkyl or C1-3-alkanoyl, phenyl, phenyl-C1-C4-alkyl, pyridyl, pyridyl-C1-C4-alkyl or imidazolyl-C1-C4-alkyl,

whereby all previously mentioned alkyl residues can be substituted with up to two substituents of OH, 0Ci_3-alkyl, NH2, NHCi_3-alkyl, NHCi_3-alkanoyl, N (Ci-3-alkyl) 2, N (Ci-3-alkyl) (Ci-3- alkanoyl), COOH, C0NH2, C00Ci_3-alkyl and all previously mentioned phenyl and pyridyl groups may be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3, C2F5,

or R<5> and R<5>' together with the nitrogen atom form a 7-pyrrolidine, morpholine, piperidine or piperazine ring and may be substituted with C1-4-alkyl, C1-4- alkoxy-Co-2-alkyl, C1-4 -Alkoxycarbonyl or aminocarbonyl,

A means C1-10-alkanediyl or C2-10-alkenediyl,

B means COOH, COOR<5>, C0NH2, C0NHNH2, CONHR<5>, CONR<5>R5', CONHOH, CONHOR<5>, S02NH2, .S02NHR<5>, S02NR<5>R<5>',

X means a bond,

Y means 0, NH, ^NR4, NS02R<4>,

whereby the following compounds are excluded: [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid methyl ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester, 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester ,

6-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(4-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[ [1-[4-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[[1-[4-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

6- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[[1-[3-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

5-[[1-[3-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

for the manufacture of a medicament for the treatment or prevention of diseases associated with a microglial activation.

The compounds according to the invention with the general formula II inhibit the activation of microglial activation. This effect is new.

In example 307, it is described how the inhibition of microglial activation can be measured. The activation of microglia can thereby take place with the help of different stimuli, such as e.g. Aβ-peptide (β-amyloid, Araujo, D.M. and Cotman, C.M., Brain Res. 569, 141-145 (1992)), prion protein, cytokines or by cell fragments (Combs, C.K. et al. (1999), J . Neurosci., 19, 928-939, Wood, P. L. (1998) Neuroinflammation: Mechanisms and Management, Humana Press). For example, the compound according to example 49 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexaneisopropyl ester shows an inhibition of IC50 =. 0.75 µM.

The stimulation with the AØ peptide corresponds to the pathophysiological situation in Alzheimer's disease. In this test, the substances according to the invention, when stimulated with the A(i-peptide) showed an inhibition of microglial activation. The inhibition of microglial activation by means of the substances according to the invention leads to a strong reduction of cytokine production and secretion, e.g. from 111(3 and TN Fa (measured by ELISA and mRNA expression analysis) and to a reduced secretion of reactive oxygen/nitrogen intermediates At the same time, several inflammatory factors are also inhibited.

The in vivo activity of the substances according to the invention was demonstrated using an MCAO model in rats. This model simulates the condition of a stroke. The substances according to the invention reduce the microglial activation that occurs during acute brain damage in the animals' brains.

The invention also relates to the use of the compounds according to the invention with the general formula I and the general formula II for the preparation of a drug for the treatment or prevention of diseases that are associated with a microglial activation. Examples of such diseases are AIDS dementia, amyotrophic lateral sclerosis, Creutzfeldt-Jakob disease, Down's syndrome, diffuse Lewy Body disease, Huntington's disease, leukoencephalopathy, multiple sclerosis, Parkinson's disease, Pick's disease, Alzheimer's disease, stroke, temporal lobe epilepsy and tumors.

Furthermore, the invention relates to pharmaceutical agents containing one or more compounds according to the invention with the general formula I and one or more carrier substances. The pharmaceutical agents or preparations according to the invention are prepared in a manner known per se with the usual solid or liquid carriers or diluents and the usual pharmaceutical and technical auxiliaries in accordance with the desired mode of administration with a suitable dosage. The preferred preparations consist in an application form suitable for oral, enteral or parenteral administration. Such forms of supply are e.g. tablets, film-coated tablets, dragées, pills, capsules, powders or depot forms as well as suppositories. Corresponding tablets can be obtained, e.g. by mixing the active ingredient. with known excipients, e.g. inert diluents such as dextrose, sugar, sorbitol, mannitol, polyvinylpyrrolidone, disintegrants such as corn starch or alginic acid, binders such as starch or gelatins, lubricants such as carboxypolymethylene, carboxymethyl cellulose, cellulose acetate phthalate or polyvinyl acetate. The tablets can also consist of several layers.

Similarly, dragees can be produced by coating cores that have been prepared analogously to the tablets, with agents that are commonly used for dragee coating, e.g. polyvinylpyrrolidone or shellac, gum arabic, talc, titanium oxide or sugar. Thereby, the dragé coating can also consist of several layers, whereby the excipients mentioned above in connection with the tablets can be used. Capsules containing active ingredients can e.g. is produced by mixing the active ingredient with an inert carrier, such as milk sugar or sorbitol, and encapsulating in gelatin capsules.

The substances according to the invention can also be used in suitable solutions, such as e.g. physiological saline solution, find use as an infusion or injection solution.

For parenteral use, particularly oily solutions, such as e.g. solutions in sesame oil, castor oil and cottonseed oil, suitable. To increase solubility, solubilizers, such as e.g. benzyl benzoate or benzyl alcohol is added.

It is also possible to incorporate the substances according to the invention into a transdermal system and thus administer them transdermally. The dosage of the substances according to the invention with the general formula I and the general formula II is determined by the attending physician and depends, among other things, of the substance administered, the method of administration, the disease to be treated and how serious the disease is. The daily dose is no more than 1000 mg, preferably no more than 100 mg, whereby the dose can be given as a single dose to be given once, or divided into 2 or more daily doses.

The compounds of formula I can exist as tautomers, stereoisomers or geometric isomers. The invention also covers all possible isomers, such as E- and Z-isomers, S- and R-enantiomers, diastereomers, racemates and mixtures of these including the tautomeric compounds... The isomer mixtures can be separated into the enantiomers or The E/Z isomers according to common methods, such as e.g. crystallization, chromatography or salt formation.

The production of the compounds according to the invention takes place analogously to known methods such as e.g. is described in EP 531 883. If the preparation of the starting compounds is not described, the starting compounds are known and can be purchased or their preparation takes place analogously to the methods described so far. Below, the production of certain preliminary steps, intermediate products and products is described as examples.

In the production of the substances according to the invention, one uses e.g. of the following procedures:

General work instructions 1:

Reduction of nitro groups, hydrogenation of olefinic double bonds and hydrogenolytic cleavage of benzyl ethers

The compound to be reduced is dissolved in ethyl acetate, tetrahydrofuran, methanol or ethanol or mixtures of the solvents and hydrated to 2-5% (based on the nitro compound) of palladium-on-charcoal (10%) at normal pressure. After completion of hydrogen uptake, suction is carried out, and the residue is washed with ethyl acetate or methanol or ethanol, and the filtrate is concentrated in vacuo. The raw product is usually sold without further purification.

General work instructions 2:

Reduction of nitro groups

9.2 g of iron (II) sulphate are placed beforehand in 30 ml of water and 9 ml of ammonia solution. To this, a solution of 3.6 mmol of the nitro compound in 100 ml of ethanol is added dropwise and the suspension is intensively stirred for 1 h at 70 °C. Then sedimentation is carried out, filtration from the solid, extensive concentration of the filtrate, addition of water and extraction three times with ethyl acetate. The combined extracts are dried over sodium sulfate and concentrated in vacuo. The amino compound is further processed as a raw product.

General work instructions 3:

Cyclization.to benzimidazoles with orthoesters

10 mmol of a 1,2-diaminobenzene derivative are dissolved in 25 ml of ethanol. To this is added dropwise 47 ml of a 0.8 M ethereal HCl solution, stirred for 30 minutes and then concentrated in vacuo to dryness. The residue is taken up in 230 ml of methanol and supplied with 6 ml of trimethylorthobenzoate or the equivalent amount of another orthoester. It is heated for 2-8 h until reflux, poured into saturated sodium bicarbonate solution after cooling, extracted three times with ethyl acetate, the combined extracts are dried over sodium sulfate and concentrated in vacuo. The remainder is purified using crystallization or column chromatography on silica gel.

General work instructions 4:

Cyclization to benzimidazoles with iminoester hydrochlorides

1.2 mmol of a 1,2-diaminobenzene derivative is dissolved in 5 ml of tetrahydrofuran, supplied with 1.5 mmol of a benzimidate hydrochloride, and the mixture is stirred for 15 h. The batch is supplied with

saturated sodium bicarbonate solution, dilute with water and extract three times with ethyl acetate. The combined organic phases are washed three times with 1 N aqueous hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate, filtered over a silica gel frit and the solution concentrated to dryness. The product is crystallized from diisopropyl ether.

General work instructions 5:

Cyclization to benzimidazoles via carboxylic acid anilides

4.7 mmol of a 1,2-diaminobenzene derivative are dissolved in

20 ml of dichloromethane, are supplied with 14 mmol of triethylamine and slowly with 6 mmol of carboxylic acid chloride, and the mixture is stirred for 15 h. The charge is supplied with saturated sodium bicarbonate solution, diluted with water and extracted twice with dichloromethane. The combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The remaining crude carboxylic acid anilide is taken up in a 9:1 mixture of methanol and concentrated hydrochloric acid and heated for 1 h to reflux. The reaction mixture becomes

.after- cooling slowly introduced into saturated sodium bicarbonate-

solution, diluted with water and extracted three times with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. If necessary, the residue is purified by means of crystallization or column chromatography on silica gel.

General work instructions 6:

Ether cleavage with hydrobromic acid

5 g of arylmethyl ether are supplied with 160 ml of 48% aqueous HBr and heated for 1-5 h until reflux. After cooling, filtration is carried out. The residue is taken up in ethyl acetate and extracted three times with saturated sodium bicarbonate solution. After drying over sodium sulphate, concentration is carried out in vacuum. If necessary, the residue is purified using crystallization or column chromatography on silica gel.

General work instructions 7:

Ether cleavage with boron tribromide

1.86 mmol of arylmethyl ether is dissolved in 18 ml of dichloromethane and slowly supplied with 7.4 ml of a 1 M solution of boron tribromide in dichloromethane at -35 °C. The mixture is allowed to stand for 12-15 h at -30 °C and then supplied with saturated sodium bicarbonate solution, extracted three times with dichloromethane, the combined extracts are dried over sodium sulphate and concentrated in vacuo. If necessary, the residue is purified using a column chromatograph on silica gel.

General work instructions:

Alkylation of hydroxybenzimidazole derivatives and phenol derivatives with alkyl halides

A solution of 1.85 mmol of the hydroxybenzimidazole derivative in 12 ml of N,N-dimethylformamide is supplied with 1.85 mmol of cesium carbonate and 2.24 mmol of alkyl bromide or alkyl iodide. When using the alkyl bromides, 1.85 mmol of sodium iodide is optionally added. The mixture is stirred for 12-96 h, then poured into water, taken up with ethyl acetate, the organic phase is washed four times with water, dried over sodium sulphate and concentrated in vacuo.

As an alternative to this aqueous work-up, the reaction mixture can be supplied with dichloromethane, separated from the precipitated salts by means of filtration and the filtrate concentrated in a vacuum.

Regardless of the preparation method, the residue is purified using crystallization or column chromatography on silica gel.

General work instructions 9:

Saponification of carboxylic acid alkyl esters

0.77 mmol of the carboxylic acid alkyl ester is dissolved in 5 ml of methanol and 5 ml of tetrahydrofuran and supplied with 5 ml of a 0.5 N aqueous lithium or sodium hydroxide solution. After stirring for 2-12 h, as strong a concentration is carried out in vacuum as possible, and it is neutralized by the addition of aqueous hydrochloric acid and extracted with ethyl acetate. It is dried over sodium sulfate and concentrated in vacuo. If necessary, the residue is purified using column chromatography on silica gel.

General work instruction 10:

Esterification of carboxylic acids

Dissolve 0.2 mmol of carboxylic acid in 1 ml of primary or secondary alcohol, add two drops of concentrated sulfuric acid and stir for 12 h at 60 °C. The batch is then supplied with saturated potassium bicarbonate solution, diluted with water and extracted three times with ethyl acetate. After washing the combined extracts with saturated sodium chloride solution and drying over sodium sulfate, concentration is carried out in vacuo, and the residue is crystallized from diisopropyl ether.

General work instructions 11:

Reduction of carboxylic acid alkyl esters with lithium aluminum hydride

0.15 mmol of carboxylic acid ester is dissolved in tetrahydrofuran and supplied with 0.09 mmol of lithium aluminum hydride. Stir for 1-48 h, add water and extract three times with dichloromethane. After drying the combined organic phases over sodium sulphate, the mixture is concentrated in vacuo. The remainder is, if necessary, purified using crystallization or column chromatography on silica gel.

General work instruction 12:

Wittig reaction of benzimidazolecarbaldehydes with (u-carboxy-alkyl)triphenylphosphonium bromides and esterification with methanol 2 mmol of the (o-carboxyalkyl)triphenylphosphonium bromide are treated in 2.5 ml of dimethylsulfoxide and 2.5 ml of tetrahydrofuran with 4 mmol of potassium tert-butylate at 0 °C and stirred for 30 minutes at T>10 °C. A solution of 0.67 mmol of the aldehyde in 2 ml of tetrahydrofuran is then added and stirred for 3 h at 20 °C. The charge is then supplied with saturated ammonium chloride solution, diluted with water and extracted three times with ethyl acetate. After drying the combined organic phases over sodium sulphate, concentration is carried out in vacuo. The residue is dissolved in 15 ml of methanol, supplied with two drops of concentrated sulfuric acid and allowed to stand for 48-72 h. After concentration in vacuum, the residue is purified using column chromatography on silica gel.

General work instruction 13:

Reaction of aminobenzimidazoles with alkyl- and arylsulphonic acid halides 47 umol of aminobenzimidazole derivative is dissolved in 0.5 ml of dichloromethane, supplied with 51 umol of triethylamine and 51 umol of alkyl or arylsulphonic acid halide, and the reaction mixture is stirred for 2-15 h. For the work-up, saturated sodium bicarbonate is added bonate solution, extract three times with dichloromethane, wash the combined organic phases with water, dry over sodium sulfate and concentrate in vacuo. The residue is purified by means of crystallization or column chromatography on silica gel.

General work instructions 14:

Copper-mediated O- or N-arylation of benzimidazoles

5 mmol of an N-unsubstituted benzimidazole derivative or an N-aryl substituted hydroxybenzimidazole derivative are dissolved in

20 ml of dichloromethane. 10 mmol of an arylboric acid are added,

5 mmol anhydrous copper(II) acetate, 10 mmol pyridine or triethylamine and approx. 2.5 g of molecular sieve (4), stir for 48-72 h while excluding moisture, then add silica gel, concentrate in vacuo to dryness and purify the remaining powder by means of chromatography on silica gel. If necessary, regioisomeric N-arylation products are separated by HPLC.

General work instructions 15:

Base-catalyzed N-substitution of benzimidazoles

5 mmol of an N-unsubstituted benzimidazole derivative are dissolved in 20 ml of dimethylacetamide. 25 mmol of sodium hydride and 20 mmol of an electron-poor aryl or heteroaryl halide are added and heated for 48-72 h under the exclusion of moisture until reflux, silica gel is then added, concentrated to dryness in vacuo and the remaining powder is purified by chromatography on silica gel. If necessary, regioisomeric N-arylation products are separated by HPLC.

General work instructions 16:

Cyclization to benzimidazoles with aldehydes

1 mmol of a 1,2-diaminobenzene derivative is dissolved in 3 ml of nitrobenzene. To this is added 1 mmol of an aryl or heteroaryl aldehyde. It is heated for 2-6 h to 150 °C and the mixture is allowed to cool. The residue is purified directly without further processing using column chromatography on silica gel.

General work instructions 17:

Transfer of carboxylic acids to carboxylic acid amides

0.25 mmol of a carboxylic acid is dissolved in 3 ml of N,N-dimethylformamide, supplied with 0.38 mmol of a primary or secondary amine, 0.5 mmol of triethylamine and 0.25 mmol of diphenylphosphorylazide, and the mixture is stirred for 2 d For the work-up, water is added, extracted three times with ethyl acetate, the combined organic phases are washed with water, dried over sodium sulphate and concentrated in vacuo. The residue is purified using column chromatography on silica gel.

General work instructions 18:

Transfer of carboxylic acid esters to carboxylic acid amides

0.36 mmol of an amine is dissolved in 3 ml of toluene and supplied, while cooling in an ice bath, dropwise with 0.18 ml of a 2 M solution of trimethylaluminum in toluene. A solution of 0.33 mmol of the carboxylic acid methyl ester in 3 ml of toluene is added and stirred for 2-8 h at 95 °C. For the work-up, water is added after cooling, extracted three times with ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution.

ning, drying over sodium sulfate and concentrating in vacuo. The residue is purified using column chromatography on silica gel.

Example 1

[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid isopropyl ester was obtained by reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole (Benincori, T.; Sannicolo, F.; J. Heterocycl. Chem.; 25; 1988; 1029-1033) with bromoacetic acid isopropyl ester according to the general working instructions 8.

Temp. 137-138 °C.

Example 2

[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethan-1-ol was obtained by reacting [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid methyl ester (DE 4330959 ) in accordance with the general work instructions 11.

<X>H-NMR (D 6 -DMSO): δ = 3.72 ppm hr (J = 7.5 Hz, 2H); 4.02 h (J = 7.5 Hz, 2H); 6.72 d (J = 2 Hz, 1H); 7.10 dd (J = 8.2 Hz, 1H); 7.38-7.68m (10H); 7.76 d (J = 8 Hz, 1H).

Example 3

3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propan-1-ol

0.5 g of 1,2-diphenyl-6-hydroxy-1H-benzimidazole was reacted with 3-(bromopropoxy)-tert-butyldimethylsilane according to general work instructions 8. After chromatography on silica gel, 2.5 ml methanol, added 0.4 ml of concentrated hydrochloric acid and allowed to stir for 2 h at 20 °C. Poured into saturated aqueous sodium bicarbonate solution, extracted three times with ethyl acetate, washed the combined extracts with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo.

Temp. 191-193 °C.

Example 4

3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid

100 mg of 3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-propan-1-ol was previously placed in 2.5 ml of acetone and supplied at -15 °C with 0.15 ml of a solution of Jones reagent (prepared from 0.27 g of chromium(VI) oxide, 1 ml of water and 0.23 ml of concentrated

sulfuric acid). After stirring for 3.5 h at -15 °C, quenching was carried out by adding isopropanol. It was diluted with water, extracted three times with dichloromethane, the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel. <1>H-NMR (De-DMSO): δ = 2.60 ppm hr (J = 7.5 Hz, 2H); 4.15 h (J = 7.5 Hz, 2H); 6.64 d (J = 2 Hz, 1H); 6.95 dd (J = 8.2 Hz, 1H); 7.30-7.61 m (10H); 7.69 d (J = 8 Hz, 1H).

Example 5

3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester 45 mg of 3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-propanoic acid was dissolved in 0, 5 ml of N,N-dimethylformamide and supplemented with 41 mg of cesium carbonate and 10 µl of methyl iodide. It was allowed to stir for 2 d, diluted with dichloromethane, filtered, the filtrate concentrated in vacuo and the residue chromatographed on silica gel.

Temp. 120-121 °C.

Example 6

2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 2-bromopropanoic acid methyl ester according to the general working instructions 8 .

Temp. 132-135 °C.

Example 7

4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid isopropyl ester

was obtained by reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 4-bromobutanoic acid isopropyl ester according to the general work instructions 8.

Temp. 89-91 °C.

Example 8

4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butan-1-ol was obtained by reacting 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy] butanoic acid methyl ester according to the general work instructions 11. ...Smp.' 159-160 pc.

Example 9

Acetic acid [4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]but-1-yl]ester

50 mg of 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butan-1-ol was dissolved in 1 ml of dichloromethane, supplied with 0.34 ml of pyridine and 20 ul of acetyl chloride and stirred for 15 h Saturated sodium bicarbonate solution was added, diluted with water, extracted twice with dichloromethane, the combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was purified by means of thick-layer chromatography. n

Temp. 68-69 °C.

Example 10

Pivalic acid-[4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]but-1-yl]ester

was analogous to the instructions given in example 9, prepared from 50 mg of 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butan-1-ol,

0.34 ml of pyridine and 22 µl of trimethylacetic acid chloride. Temp. 104-106 °C.

Example 11

4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butyl-N-methylcarbamate

100 mg of 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butan-1-ol was dissolved in 4 ml of dichloromethane, supplied with 0.1 ml of triethylamine and 20 mg of methyl isocyanate and stirred for 15 h A further 0.1 ml of triethylamine and 20 mg of methyl isocyanate were added, allowed to stir for 20 h and then concentrated in vacuo. The residue was purified by chromatography on silica gel.

Temp. 124-126 °C. ,

Example 12

5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid isopropyl ester 994

was obtained by reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 5-bromopentanoic acid isopropyl ester according to the general work instructions 8.

Temp. 91-92 °C.

Example 13

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8 .

1H-NMR (CDCl 3 ).: δ = 1.44-1.56 m (2H); 1.64-1.85 m (4H); 2.33 h (J = 7.5 Hz, 2H); 3.66 s (3H); 3.93 h (J = 7.5 Hz, 2H); 6.70 d (J = 2 Hz, 1H); 6.96 dd (J = 8.2 Hz, 1H); 7.22-7.38 m (5H); 7.43-7.58m (5H); 7.76 d (J = 8 Hz, 1H).

Example 14

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester

was obtained by reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general work instructions 8.

<X>H-NMR (CDCl 3 ): δ = 1.22 ppm d (J = 7.5 Hz, 6H); 1.43-1.56 m (2H); 1.62-1.87 m (4H); 2.30 h (J = 7.5 Hz, 2H); 3.93 h (J = 7.5 Hz, 2H); 5.01 sp (J = 7.5 Hz, 1H); 6.69 d (J = 2 Hz, 1H);

6.96 dd (J = 8.2 Hz, 1H); 7.25-7.38m (5H); 7.43-7.55 m (5H);

7.75 d (J = 8 Hz, 1H).

Example 15

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid was obtained by reacting 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester according to the general work instructions 9.

<X>H-NMR (De-DMSO): δ = 1.35-1.49 ppm m (2H); 1.50-1.63 m (2H);

1.65-1.77 m (2H); 2.23 h (J = 7.5 Hz, 2H); 3.92 h (J = 7.5 Hz, 2H); 6.62 d (J = 2 Hz, 1H); 6.95 dd (J = 10, 2 Hz, 1H); 7.30-7.62 m (10H); 7.68 d (J = 10 Hz, 1H).

Example 16

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexan-1-ol was obtained by reacting 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy] hexanoic acid methyl ester according to the general work instructions 11.

<1>H-NMR_ (CDCl3): δ = 1.35-1.85 ppm m (8H); 3.67 h (J = 7.5 Hz, 2H); 3.98 h "(J = 7.5. Hz, 2H); 6.70 d (J = 2 Hz, 1H) ; 6.98 dd (J-

= 8.2 Hz, 1H); 7.24-7.38m (5H); 7.45-7.58m (5H); 7.75 d (J = 8 Hz, 1H).

Example 17

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

a) 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanenitrile was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 6-bromohexanenitrile according to the general work instructions 8.

Temp. 108-112 °C.

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

To a solution of 50 mg of 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanenitrile in 1 ml of methanol, 18 mg of potassium carbonate and 40 ul of 30% hydrogen superoxide solution were added and stirred for 24 h. Ice-cold, aqueous sodium thiosulphate solution was then stirred in and extracted three times with ethyl acetate. After drying over sodium sulphate, concentration was carried out in vacuo and the residue chromatographed on silica gel.

<X>H-NMR (CDCl 3 ): δ = 1.48-1.60 ppm m (2H); 1.65-1.87 m (4H); 2.25 h (J = 7.5 Hz, 2H); 3.94 h (J = 7.5 Hz, 2H); 5.30-5.53 wide (2H); 6.68 d (J = 2 Hz, 1H); 6.95 dd (J = 8.2 Hz, 1H); 7.23-7.38 m (5H); 7.42-7.58m (5H); 7.75 d (J = 8 Hz, 1H).

Example 18

N-methoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

100 mg of 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid was dissolved in 2 ml of tetrahydrofuran, treated with 39 mg of carbonyldiimidazole, stirred for 30 min at 20 °C and then heated for 30 min until reflux. At 20 °C, 21 mg of 0-methylhydroxylamine hydrochloride was then added and allowed to stir for 18 h. The reaction mixture was diluted with ethyl acetate and washed with 2 N aqueous hydrochloric acid and saturated potassium bicarbonate solution. After drying over sodium sulphate, it was concentrated in vacuo and the residue chromatographed on silica gel.

Temp. 144-145 °C.

Example 19

N-(phenylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

was obtained by reacting 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid with O-benzylhydroxylamine hydrochloride according to the working instructions given in example 18.

Temp. 144 °C.

Example 20

N-hydroxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide 23 mg N-(phenylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl) )oxy]hexanamide was dissolved in 4 ml of ethanol, provided with 15 mg of palladium-on-charcoal (10%) and stirred for 3 h under a hydrogen atmosphere. After separation from the catalyst, it was concentrated in vacuo and the residue crystallized from diethyl ether.

Temp. 83-85 °C.

Example 21

7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid methyl ester was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 7-bromoheptanoic acid methyl ester according to the general working instructions 8 .

Temp. 77-80 °C.

Example 22

7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid was obtained by reacting 7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid methyl ester according to the general work instructions 9.

Temp. 142-145 °C.

Example 23

7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid isopropyl ester

was obtained by reacting 7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid with isopropanol according to the general work instructions 10.

Temp. 98-100 °C.

Example 24

6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

was obtained by reaction of 6-hydroxy-1-(3-nitrophenyl)-2-phenyl-1H-benzimidazole (DE 4330959) with 6-bromohexanoic acid isopropyl ester according to the general work instructions 8.

Temp. 111-113 °C.

Example 25

6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

a) (5-Methoxy-2-nitrophenyl)[(3-trifluoromethyl)phenyl]amine

2 g of 3-fluoro-4-nitroanisole and 16 ml of 3-(trifluoromethyl)-aniline were stirred for 72 h at 140 °C. The batch was then diluted with ethyl acetate, washed ten times with 4 N aqueous hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo, and the residue was chromatographed on silica gel. <1>H-NMR (CDCl 3 ): δ = 3.78 ppm s (3H); 6.42 dd (J = 8.2 Hz, 1H); 6.60 d (J = 2 Hz, 1H); 7.45-7.60m (4H); 8.22 d (J = 8 Hz, 1H); 9.78s (wide)(1H). b) 6-Methoxy-2-phenyl-1-[(3-trifluoromethyl)phenyl]-1H-benzimidazole was obtained by hydrogenation of (5-methoxy-2-nitrophenyl) [(3-trifluoromethyl)phenyl]amine in according to the general work instructions 1 and subsequent cyclization with triethylorthobenzoate according to the general work instructions.

Temp. 135-137 °C. c) 6-hydroxy-2-phenyl-1-[(3-trifluoromethyl)phenyl]-1H-benzimidazole was obtained by reacting 6-methoxy-2-phenyl-1-[(3-trifluoromethyl)phenyl] - 1H-benzimidazole according to the general work instructions 6.

3-NMR (D 6 -DMSO): δ = 6.56 ppm d (J = 2 Hz, 1H); 6.82 dd (J = 8.2 Hz, 1H); 7.32-7.50 m (5H); 7.60 d (J = 8 Hz, 1H); 7.70-7.95 m (4H); 9.48 s (wide) (1H) .

6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

was obtained by reacting 6-hydroxy-2-phenyl-1-[(3-trifluoromethyl)phenyl]-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

Temp. 106-108 °C.

Example 26

6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester

was obtained by reaction of 6-hydroxy-2-phenyl-1-[(3-trifluoro-methyl)phenyl]-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8.

Temp. 113-115 °C.

Example 27

6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid

was obtained by reaction of 6-[[2-phenyl-1-[3-(trifluoromethyl)-phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 156-158 °C.

Example 28

6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexan-1-ol

was obtained by reacting 6-[[2-phenyl-1-[3-(trifluoromethyl)-phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 11.

Temp. 143-145 °C.

Example 29

6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 3-(5-Methoxy-2-nitrophenyl)aminobenzonitrile

2 g of 3-fluoro-4-nitroanisole and 15 ml of 3-aminobenzonitrile

was stirred at 140 °C for 65 h. The charge was then diluted with ethyl acetate, washed three times with water and once with saturated

sodium chloride solution, dried over sodium sulfate and concentrated in vacuo, and the residue was chromatographed on silica gel.

Temp. 157-158 °C. b) 6-methoxy-1-(3-cyanophenyl)-2-phenyl-1H-benzimidazole was obtained by hydrogenation of 3-(5-methoxy-2-nitrophenyl)aminobenzonitrile according to the general working instruction 1 and subsequent cyclization with triethylorthobenzoate in accordance with the general work instructions 3. During the cyclization, as a deviation from the general work instructions, tetrahydrofuran was used as solvent.-- . "

Temp. 185-191 °C (decomp.).

c) 6-hydroxy-1-(3-cyanophenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-1-(3-cyanophenyl)-2-phenyl-1H-benzimidazole according to the general work instructions 7. Smp. 216-218 °C.

The 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acids tyles

was obtained by reaction of 6-hydroxy-1-(3-cyanophenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

Temp. 115-118 °C.

Example 30

6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

was obtained by reaction of 6-hydroxy-1-(3-cyanophenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8.

Temp. 101-102 °C.

Example 31

6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[1-(3-cyanophenyl)-2-phenyl-1H- benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 99-101 °C.

Example 32

6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

1) 4-(5-Methoxy-2-nitrophenyl)aminobenzonitrile

2 g of 3-fluoro-4-nitroanisole and 15 ml of 4-aminobenzonitrile were stirred for 22 h at 140 °C. The batch was then diluted with ethyl acetate, washed three times with 2 N aqueous hydrochloric acid, three times with water and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo, and the residue was chromatographed on silica gel.

<X>H-NMR (CDCl 3 ): δ = 3.70 ppm s (3H); 6.38 dd (J = 8.2 Hz, 1H); 6.68 d (J = 2 Hz, 1H); 7.27 d (J = 8 Hz, 2H); 7.54 d (J = 8 Hz, 2H); 8.08 d (J = 8 Hz, 1H); 9.60 s (wide)(1H). b) 6-methoxy-1-(4-cyanophenyl)-2-phenyl-1H-benzimidazole was obtained by hydrogenation of 4-(5-methoxy-2-nitrophenyl)aminobenzonitrile according to the general working instruction 1 and subsequent cyclization with triethylorthobenzoate i. according to the general work instructions 3. During the cyclization, in contrast to the general work instructions, tetrahydrofuran was used as solvent.

<X>H-NMR (CDCl 3 ): δ = 3.82 ppm s (3H); 6.72 d (J = 2 Hz, 1H); 7.00 dd (J = 8, 2 Hz, 1H); 7.30-7.49 m (7H); 7.78 d (J = 8 Hz, 1H); 7.81 d (J = 8 Hz, 2H). c) 6-hydroxy-1-(4-cyanophenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-1-(4-cyanophenyl)-2-phenyl-1H-benzimidazole according to the general work instructions 7. Smp. 266-268 °C.

6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

was obtained by reaction of 6-hydroxy-1-(4-cyanophenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

Temp. 145-148 °C.

Example 33

6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

was obtained by reaction of 6-hydroxy-1-(4-cyanophenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8..

Temp. 102-103 °C.

Example 34

6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester a) 1-(3-chlorophenyl)-6-methoxy-2-phenyl-1H-benzimidazole was obtained by reduction of (3-chlorophenyl)-(5-methoxy-2-nitrophenyl)amine (Belton, Mc Inerney; Proe. R. Ir. Acad. Sect. B; 69; 1970; 21,27) according to the general work instructions 2 and subsequently. cyclization with triethylorthobenzoate according to the general work instructions 3.

Temp. 140-143 °C. b) 1-(3-chlorophenyl)-6-hydroxy-2-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-1-(3-chlorophenyl)-2-phenyl-1H-benzimidazole according to the general work instructions 6. Smp. 210-214 °C.

6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol^6-yl]oxy]hexane acid methyl ester

was obtained by reaction of 1-(3-chlorophenyl)-6-hydroxy-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

Temp. 101-105 °C.

Example 35

6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester

was obtained by reaction of 1-(3-chlorophenyl)-6-hydroxy-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8.

Temp. 107-112 °C.

Example 36

6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol -6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

<1>H-NMR (D6-DMSO): 6 = 1.36-1.78 ppm m (6H); 2.24 h (J = 7.5 Hz, 2H); 3.96 h (J 7.5 Hz, 2H); 6.68 d (J = 2 Hz, 1H); 6.97 dd (J 8 , 2 Hz, 1H); 7.32-7.65 m (9H); 7.69 d (J = 8 Hz, 1H).

Example 37

6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

was obtained by reacting 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 11.

<1>H-NMR (CDCl 3 ): δ = 1.38-1.88 ppm m (8H); 3.67 h (J = 7.5 Hz,

2H); 3.96 h (J = 7.5 Hz, 2H); 6.70 d (J = 2 Hz, 1H); 6.97 dd (J

= 8.2 Hz, 1H); 7.18 ddd (J = 8, 2, 2 Hz, 1H); 7.25-7.55 m (8H); 7.76 d (J = 8. Hz, 1H) .

Example 38

6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester a) 1-(4-chlorophenyl)-6-methoxy-2-phenyl-1H-benzimidazole was obtained by reduction of (4-chlorophenyl)-(5-methoxy-2-nitrophenyl)amine (Kottenhahn et al.; J. Org. Chem.; 28; 1963; 3114, 3118) according to the general working instructions 2 and with subsequent cyclization with triethylorthobenzoate according to the general work instructions 3.

<X>H-NMR (CDCl 3 ): δ = 3.82 ppm s (3H); 6.67 d (J = 2 Hz, 1H); 6.97 dd (J = 8.2 Hz, 1H); 7.22-7.40 m (5H); 7.46-7.55 m (4H); 7.77 d (J = 8 Hz, 1H) . b) 1-(4-chlorophenyl)-6-hydroxy-2-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-1-(4-chlorophenyl)-2-phenyl-1H-benzimidazole according to the general work instructions 6. ^•H-NMR (D6-DMSO) : 5 = 6.60 ppm d (J = 2 Hz, 1H) ; 6.87 dd (J = 8.2 Hz, 1H); 7.40-7.56 m (7H); 7.64 d (J = 8 Hz, 1H); 7.70 d (J = 8 Hz, 2H); 9.50 s (wide) (1H) .

6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

was obtained by reaction of 1-(4-chlorophenyl)-6-hydroxy-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

Temp. 100-104 °C.

Example 39

6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

was obtained by reaction of 1-(4-chlorophenyl)-6-hydroxy-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8.

Temp. 83-88 °C.

Example 40

6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[1-(4-chlorophenyl)-2-phenyl-1H- benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

<1>H-NMR (De-DMSO): 6 = 1.35-1.78 ppm m (6H); 2.25 h (J = 7.5 Hz, 2H); 3.94 h (J = 7.5 Hz, 2H); 6.68 d (J = 2 Hz, 1H); 6.95 dd (J = 8.2 Hz, 1H); 7.33-7.54 m (7H); 7.63 d (J = 8 Hz, 2H); 7.69 d (J = 8 Hz, 1H) .

Example 41

6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

was obtained by reacting 6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 11.

Temp. 115-120 °C.

Example 42

6-[[1-(2-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 5-chloro-2-nitrophenyl-o-tolylamine

To a solution of 10 g of l-chloro-3,4-dinitrobenzene i

81 ml of o-toluidine was added to 50 ml of ethanol and heated for 72 h until reflux. It was concentrated in vacuo and the residue was taken up in ethyl acetate and 2 N aqueous hydrochloric acid. The organic phase was extracted three more times with 2 N aqueous hydrochloric acid, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel.

<1>H-NMR (CDCl3) : δ = 2.28 ppm s (3H); 6.70 dd (J = 10, 2 Hz, 1HJ; 6.80 d (J = 2 Hz, 1H); 7.22-7.40 m (4H); 8.18 d (J = 10 Hz, 1H ) ; 9.40 s (wide)(1H).

b) 5-methoxy-2-nitrophenyl-o-tolylamine

To a solution of 1 g of sodium in 20 ml of methanol

1 g of 5-chloro-2-nitrophenyl-o-tolylamine was added and heated for 72 h until reflux. Cooling to 0 °C was then carried out and the crystalline product sucked off.

<1>H-NMR (CDCl3) : δ = 2.30 ppm s (3H); 3.72 s (3H); 6.19 d (J =

2Hz, 1H); 6.32 dd (J = 10, 2 Hz, 1H); 7.20-7.40m (4H); 8.20 d (J = 10 Hz, 1H); 9.62 s (wide)(1H). c) 6-methoxy-1-(2-methylphenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 5-methoxy-2-nitrophenyl-o-tolylamine 1 according to the general working instructions 1 and with subsequent cyclization with triethylorthobenzoate in accordance with the general work instructions 3.

<1>H-NMR (CDCl3) : δ = 1.93 ppm s (3H); 3.78 s (3H); 6.42 d (J =

2Hz, 1H); 6.97 dd (J = 8.2 Hz, 1H); 7.22-7.48 m (7H); 7.57 dd (J = 8, 1 Hz, 2H); 7.78 d (J = 8 Hz, 1H). 6-[[1-(2-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester 6-Methoxy-1-(2-methylphenyl)-2-phenyl-1H-benzimidazole was reacted according to general working instructions 6. The crude product was reacted with 6-bromohexanoic acid methyl ester according to general working instructions 8. <1>H-NMR (CDCl3) : δ = 1.43-1.58 ppm m (2H); 1.62-1.84 m (4H); 1.93 s (3H); 2.34 h (J = 7.5 Hz, 2H); 3.68 s (3H); 3.90 h (J = 7.5 Hz, 2H); 6.42 d (J = 2 Hz, 1H); 6.96 dd (J = 8.2 Hz, 1H); 7.22-7.48 m (7H); 7.56 dd (J = 8, 1.5 Hz, 2H); 7.76 d (J = 8 Hz, 1H) : Example 43

6-[[1-(2-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

was obtained by reacting 6-[[1-(2-methylphenyl)-2-phenyl-1H-benzimidazol-:6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 198-200 °C.

Example 44

6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 5-chloro-2-nitrophenyl-m-tolylamine

To a solution of 50 g of l-chloro-3,4-dinitrobenzene i

81 ml of m-toluidine was added to 250 ml of ethanol and the solution was allowed to stand for 72 h. The reaction mixture was filtered and the crystal lysate was washed with cold ethanol and 2 N aqueous hydrochloric acid. It was purified by means of chromatography on silica gel.

<1>H-NMR (CDCl 3 ): δ = 2.40 ppm s (3H); 6.72 dd (J = 10, 2 Hz, 1H); 7.04-7.13 m (3H); 7.14 d (J = 2 Hz, 1H); 7.32 h (J = 10 Hz, 1H); 8.18 d (J = 10 Hz, 1H); 9.52 s (wide)(lH).

b) 5-methoxy-2-nitrophenyl-m-tolylamine

To a solution of 9 g of sodium in 670 ml of methanol

39 g of 5-chloro-2-nitrophenyl-m-tolylamine were added and heated for 72 h until reflux. Cooling to 0 °C was then carried out and the crystalline product sucked off.

<2>H-NMR (CDCl3) : δ = 2.40 ppm s (3H); 3.73 s (3H); 6.33 dd (J = 10, 2 Hz, 1H); 6.58 d.(J = 2 Hz, 1H); 7.03-7.15 m (3H); 7.31 h (J = 10 Hz, 1H); 8.19 d (J = 10 Hz, 1H); 9.72s (wide)(1H).

c) 6-methoxy-1-(3-methylphenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 5-methoxy-2-nitrophenyl-m-tolylamine 1 according to the general working instructions 1 and with subsequent cyclization with triethylorthobenzoate in accordance with the general work instructions 3.

<1>H-NMR (CDCl 3 ): δ = 2.42 ppm .s (3H); 3.81 s (3H); 6.69 d (J =

2Hz, 1H); 7.03 dd (J - 8.2 Hz, 1H); 7.10-7.18m (2H); 7.30-7.48m (5H); 7.62 dd (J = 8, 1 Hz, 2H) 7.89 d (J = 8 Hz, 1H) . d) 6-hydroxy-1-(3-methylphenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-1-(3-methylphenyl)-2-phenyl-1H-benzimidazole according to the general working instructions 6. thaw-NMR (D6-DMSO): δ = 2.34 ppm s (3H); 6.52 d (J = 2 Hz, 1H); 6.80 dd (J = 8.2 Hz, 1H); 7.15 d (J = 8 Hz, 1H); 7.28 s (wide)(lH); 7.32-7.55 m (7H), 7.59 d (J = 8 Hz, 1H); 9.37 s (wide) 1H).

6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

was obtained by reaction of 6-hydroxy-1-(3-methylphenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

<1>H-NMR (CDCl 3 ): δ = 1.44-1.58 ppm m (2H); 1.64-1.85 m (4H); 2.35 h (J = 7.5 Hz, 2H); 2.40 s (3H); 3.68 s (3H); 3.95 h (J =

7.5 Hz, 2H); 6.70 d (J = 2 Hz, 1H); 6.96 dd (J = 8.2 Hz, 1H); 7.10 d (J = 8 Hz, 1H); 7.16 s (broad) (2H); 7.25-7.43m (4H); 7.55 dd (J = 8, 1 Hz, 2H); 7.77 d (J = 8 Hz, 1H).

Example 45

6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

was obtained by reaction of 6-hydroxy-1-(3-methylphenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8.

<X>H-NMR (CDCl 3 ): 6 = 1.22 ppm d (J= 8 Hz, 6H); 1.44-1.56 m (2H, CH2), 1.64-1.84 m (4H, CH2); 2.30 h (J = 7.5 Hz, 2H); 2.41 s (3H); 3.95 h (J = 7.5 Hz, 2H); 5.00 sp (J = 8 Hz, 1H); 6.68 d (J = 2 Hz, 1H); 6.96 dd (J = 8.2 Hz, 1H); 7.10 d (J = 8 Hz, 1H); 7.14 s (wide)(lH); 7.25-7.41 m (4H); 7.54 dd (J = 8, 1 Hz, 2H); 7.75 d (J = 8 Hz, 1H).

Example 46

6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

was obtained by reacting 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

1H-NMR (De-DMSO): δ = 1.38-1.80 ppm m.(6H); 2.23 h (J = 7.5 Hz, 2H); 3.84-3.93 m (2H); 6.60 d (J = 2 Hz, 1H); 6.87 d (broad)(J = 8 Hz, 1H); 7.15 d (J = 8 Hz, 2H); 7.20-7.32m (4H); 7.42-7.50 rn"

(2H); 7.59 d (J = 8 Hz, 1H); 7.77 d (J = 8 Hz, 1H).

Example 47

6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

was obtained by reacting 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 11.

<1>H-NMR (CDCl3): δ = 1.40-1.85 m (8H); 2.40 s (3H); 3.68 h (J = 7.5 Hz, 2H); 3.96 h (J = 7.5 Hz, 2H); 6.69 d (J = 1.5 Hz, 1H); 6.96 dd (J = 8, 1.5 Hz, 1H); 7.10 d (J = 8 Hz, 1H); 7.13 s (wide)(lH); 7.25-7.42m (5H); 7.54 dd (J = 8, 1 Hz, 2H); 7.76 d

(J = 8 Hz, 1H).

Example 48

6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 5-chloro-2-nitrophenyl-p-tolylamine

was analogously to 5-chloro-2-nitrophenyl-m-tolylamine prepared from 1-chloro-3,4-dinitrobenzene and p-toluidine. Purification was carried out by means of crystallization.

<1>H-NMR (CDCl3): δ = 2.40 ppm s (3H); 6.70 dd..(J = 10, 2 Hz, 1H) ; 7.08 d (J = 2 Hz, 1H); 7.16 d (J = 10 Hz, 2H); 7.28 d (J =

10Hz, 2H); 8.18 d (J = 10 Hz, 1H); 9.50s (wide)(1H).

b) 5-methoxy-2-nitrophenyl-p-tolylamine

was prepared analogously with 5-methoxy-2-nitrophenyl-m-tolylamine from

5-chloro-2-nitrophenyl-p-tolylamine and sodium methanolate.

<X>H-NMR (CDCl 3 ): δ = 2.39 ppm s (3H); 3.72 s (3H); 6.31 dd (J = 10, 2 Hz, 1H); 6.50 d (J = 2 Hz, 1H); 7.19 d (J = 10 Hz, 2H); 7.25 d (J = 10 Hz, 2H); 8.19 d (J = 10 Hz, 1H); 9.70s (wide)(1H).

c) 6-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 5-methoxy-2-nitrophenyl-p-tolylamine

in accordance with the general work instructions 1 and following

cyclization with triethylorthobenzoate according to the general work instructions 3.

<1>H-NMR (CDCl3) : δ = 2.49 ppm s (3H); 3.80 s (3H); 6.69 d (J =

2Hz, 1H); 6.97 dd (J = 8.2 Hz, 1H); 7.20 d (broad)(J = 8 Hz, 2H); 7.25-7.36 m (5H); 7.53 dd (J = 8, 1 Hz, 2H); 7.76 d (J =

8 Hz, 1H).

d) 6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole according to the general work instructions 6. <1>H-NMR-(D6-DMSO) : 6 = 2.40 ppm s (3H) ; 6.50 d (J = 2 Hz, 1H); 6.80 dd (J = 8.2 Hz, 1H); 7.28 d (J = 8 Hz, 2H); 7.32-7.43 m (5H); 7.46-7.52 m (2H); 7.56 d (J = 8 Hz, 1H); 9.28 s (wide)(1H). 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester was obtained by reaction of 6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8. 1H-NMR (CDCl 3 ): δ = 1.44-1.58 ppm m (2H); 1.62-1.86 m (4H); 2.34 h (J = 7.5 Hz, 2H); 2.48 s (3H); 3.68 s (3H); 3.94 h (J = 7.5 Hz, 2H); 6.69 d (J = 2 Hz, 1H); 6.96 dd (J = 8.2 Hz, 1H); 7.19 d (J = 8 Hz, 2H); 7.28-7.38m (5H); 7.55 dd (J = 8, 1 Hz, 2H); 7.75 d (J = 8 Hz, 1H). Example 49 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester was obtained by reacting 6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8. <X>H-NMR (CDCl3) : 5 = 1, 22 ppm d (J = 7.5 Hz, 6H); 1.44-1.56 m (2H); 1.62-1.85 m (4H); 2.30 h (J = 7.5 Hz, 2H); 2.47 s (3H); 3.93 h (J = 7.5 Hz, 2H); 5.01 sp (J = 7.5 Hz, 1H); 6.68 d (J = 2 Hz, 1H); 6.96 dd (J = 8.2 Hz, 1H); 7.20 d (J = 8 Hz, 2H)\-7.26-7.36 m (5H); 7.55 dd (J 8 , 1 Hz, 2H); 7.75 d (J = 8 Hz, 1H) .

Example 50

6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

was obtained by reacting 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 186-190 °C.

Example 51

6- [ [1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

was obtained by reacting 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 11.

3-NMR (CDCl 3 ): δ = 1.38-1.80 m (8H); 2.47 s (3H); 3.65 h (J = 7.5 Hz, 2H); 3.93 h (J = 7.5 Hz, 2H); 6.68 d (J = 2 Hz, 1H); 6.97 dd (J = 8.2 Hz, 1H); 7.18 d (J = 8 Hz, 2H); 7.24-7.37 m (5H); 7.54 dd (J =8, 1 Hz, 2H); 7.75 d (J = 8 Hz, 1H).

Example 52

6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

a) 3-(3,4-dimethylphenyl)amino-4-nitrophenol

3 g of 3-fluoro-4-nitrophenol and 6.9 g of 3,4-dimethylaniline were

mixed with each other and stirred for 2 h at 150 °C. After cooling, the mixture was dissolved in dichloromethane and extracted six times with 1 N aqueous hydrochloric acid. The organic phase was discarded and the combined aqueous phases were extracted three times with chloroform. The combined extracts were dried over sodium sulfate and concentrated in vacuo, and the residue was chromatographed on silica gel. <1>H-NMR (CDCl 3 /D 6 -DMSO): δ = 2.18 ppm s (6H); 6.13 dd (J = 8.2 Hz, 1H); 6.36 d (J = 2 Hz, 1H); 6.90-7.00 m (2H); 7.09 d (J =

8Hz, 1H); 7.93 d (J = 8 Hz, 1H); 9.50 s (wide)(lH).

b) 6-[3-(3,4-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

was obtained by reaction of 3-(3,4-dimethylphenyl)amino-4-nitro-phenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

<1>H-NMR (CDCl3): δ = 1.38-1.52 ppm m (2H); 1.59-1.80m (4H); 2.30 s (6H); 2.33 h (J = 7.5 Hz, 2H); 3.68 s (3H); 3.87 h (J =

7.5 Hz, 2H); 6.28 dd (J = 8.2 Hz, 1H); 6.48 d (J = 2 Hz, 1H); 7.04 d (J = 8 Hz, 1H); 7.06 s (wide)(1H); 7.18 d (J = 8 Hz, 1H); 8.17 d (J = 8 Hz, 1H); 9.71s (wide)(1H).

6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reacting 6-[3-(3,4-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to general working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to general working instructions 3.

<1>H-NMR (CDCl3): δ = 1.44-1.56 ppm m (2H); 1.62-1.84 m (4H); 2.30 s (3H); 2.33 h (J = 7.5 Hz, 2H); 2.34 s (3H); 3.68 s (3H); 3.93 h (J = 7.5 Hz, 2H); 6.67 d (J = 2 Hz, 1H); 6.94 dd (J = 8.2 Hz, 1H); 7.03 dd (J = 8, 1.5 Hz, 1H); 7.09 s (wide)(lH); 7.22-7.35 m (4H); 7.57 dd (J = 8, 1.5 Hz, 2H); 7.76 d (J = 8 Hz, 1H).

Example 53

6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

was obtained by reacting 6-[[1-(3, 4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 158-161 °C.

Example 54

6-[[1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

a) 3-(3,5-dimethylphenyl)amino-4-nitrophenol

5.4 g of 3-fluoro-4-nitrophenol and 4.3 ml of 3,5-dimethylaniline

were mixed together and stirred at 120 °C for 6 h. After cooling, the mixture was taken up in ethyl acetate and water and extracted three times with 1 N aqueous hydrochloric acid. The combined aqueous phases were extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo, and the residue was crystallized.

hi-NMR (D6-DMSO):• δ = 2.30 ppm s (6H); 6.28 dd (J = 8.2 Hz, 1H); 6.49 d (J = .2 Hz, .1H); 6.52 d (J 2 Hz, 1H); 6.90s (wide)(1H); 6.98 s (wide)(2H); 8.04 d (J = 8 Hz, 1H); 9.51 s (wide)(1H).

b) 6-[3-(3,5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

was obtained by reaction of 3-(3,5-dimethylphenyl)amino-4-nitro-phenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

<X>H-NMR (CDCl 3 ): δ = 1.40-1.52 ppm m (2H); 1.60-1.80 m (4H); 2.30 h (J = J.5Hz,.. 2H) ;. 2.32 s J6H) ;■ 3.68 s (3H) ; 3.88 h (J

7.5 Hz, 2H); 6.30 dd"(J = 8, 2 Hz, 1H); 6.52 d (J = 2 Hz, 1H); 6.88 s (broad)dH); 6.91 s (broad) (2H) ; 8.17 d (J = 8 Hz, 1H); 9.69 s (broad)(1H).

6-[3-(3,5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

was obtained by reacting 6-[3-(3,5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to general working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to general working instructions 3.

Temp. 124-126 °C.

Example 55

6-[[1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

was obtained by reacting 6-[3-(3, 5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to the general work instructions 9.

Temp. 162-164 °C. ,

Example 56

6-[[1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reacting 6-[3-(3,5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid with isopropanol according to the general work instructions 10.

Temp. 98-101 °C.

Example 57

6-[[1-(3-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 3-(3-Methoxyphenyl)amino-4-nitrophenol

4 g of 3-fluoro-4-nitrophenol and 9.4 g of m-anisidine were

mixed with each other and stirred at 150 °C for 2.5 h. After cooling, the mixture was dissolved in dichloromethane and extracted three times with 1 N aqueous hydrochloric acid. The organic phase was dried over sodium sulfate and concentrated in vacuo, and the residue was chromatographed on silica gel.

<1>H-NMR (CDCl 3 ): δ = 3.83 ppm s (3H); 6.30 dd (J = 10, 2 Hz, 1H); 6.57 d (J = 2 Hz, 1H); 6.70-6.84 m (2H); 6.89 d (broad)(J = 10 Hz, 1H); 7.32 h (J = 10 Hz, 1H); 8.19 d (J = 10 Hz, 1H); 9.68 s (wide)(lH); 9.69 s (wide).

b) 6-[3-(3-Methoxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

was obtained by reaction of 3-(3-methoxyphenyl)amino-4-nitro-phenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

<1>H-NMR (CDCl3) : δ = 1.42-1.58 ppm m (2H); 1.60-1.93 m (4H); 2.34

t (J = 7.5 Hz, 2H); 3.68 s (3H); 3.80 s (3H); 4.03 h (J =

7.5 Hz, 2H); 6.32 dd (J = 10, 2 Hz, 1H); 6.59 d (J = 2 Hz, 1H); 6.68-6.84 m (2H); 6.90 d (broad)(J = 8 Hz, 1H); 7.32 h (J = 8 Hz, 1H); 8.19 d (J = 10 Hz, 1H); 9.70 s (wide)(lH).

6-[[1-(3-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

was obtained by reacting 6-[3-(3-methoxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to general working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to general working instructions 3.

H1-NMR (CDCl3): δ = 1.44-1.58 ppm m (2H); 1.62-1.86 m (4H); 2.34

t (J = 7.5 Hz, 2H); 3.68 s (3H); 3.78 s (3H); 3.95 h (J =

7.5 Hz, 2H); 6.71 d (J = 1.5 Hz, 1H); 6.83 dd (J = 1.5, 1.5 Hz, 1H); 6.90 dd (J = 8, 1.5 Hz, 1H); 6.94 dd (J = 8, 1.5 Hz, 1H); 7.01 dd (J = .8, 1.5 Hz, 1H); 7.27-7.36 m (3H); 7.40 h (J = 8 Hz, 1H); 7.56 dd (J = 8, .2 Hz, 2H); 7.74 d (J = 8 Hz, 1H) .

Example 58

6-[[1-(3-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

was obtained by reacting 6-[[1-(3-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 14 9-152 °C.

Example 59

6-[[1-(4-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 3-(4-Methoxyphenyl)amino-4-nitrophenol

0.16 g of 3-fluoro-4-nitrophenol and 0.37 g of p-anisidine were

mixed with each other and stirred at 150 °C for 1.5 h. After cooling, the mixture was dissolved in dichloromethane and extracted twice, with 1 N aqueous hydrochloric acid and once with saturated sodium chloride solution. The organic phase was dried over sodium sulfate and concentrated in vacuo.

<1>H-NMR (CDCl3/D6-DMSO): δ = 3.57 ppm s (3H); 6.06 dd (J = 10,

2Hz, 1H); 6.18 d (J = 2 Hz, 1H); 6.77 d (J = 10 Hz, 2H); 7.03 d (J = 10 Hz, 2H); 7.89 d (J = 10 Hz, 1H); 9.40 s (wide) (1H) ; 9.80 s (wide) . b) 6-[3-(4-methoxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester was obtained by reaction of 3-(4-methoxyphenyl)amino-4-nitro-phenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8. <1>H-NMR (CDCl3): δ = 1.38-1.50 ppm m (2H); 1.60-1.80 m (4H); 2.33 h (J = 7.5 Hz, 2H); 3.67 s (3H); 3.85 h (J = 7.5 Hz, 2H); 3.88 s (3H); 6.29 dd (J = 10, 1.5 Hz, 1H); 6.30 d (J = 1.5 Hz, 1H); 6.98 d (J = 10 Hz, 2H); 7.20 d (J = 10 Hz, 2H); 8.18 d (J = 10 Hz, 1H); 9.63 s (wide)(1H).

6-[[1-(4-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

was obtained by reacting 6-[3-(4-methoxyphenyl)amino-4-nitrq-phenyl]oxyhexanoic acid methyl ester according to the general

work instructions 1 and with subsequent cyclization with triethylorthobenzoate according to general work instructions 3.

Temp. 98-102 °C.

Example 60

6-[[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

was obtained by reacting 6-[[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 160-165 °C.

Example 61

6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

a) 3-(3,4-dimethoxyphenyl)amino-4-nitrophenol

3 g of 3-fluoro-4-nitrophenol and 8.8 g of 3,4-dimethoxyaniline

were mixed together and stirred at 150 °C for 2 h. After cooling, the mixture was dissolved in dichloromethane and extracted twice with 1 N aqueous hydrochloric acid. The aqueous phase was extracted twice with chloroform, and the combined chloroform extracts were dried over sodium sulfate and concentrated in vacuo.

<1>H-NMR (D6-DMSO): δ = 3.75 ppm s (3H); 3.78 s (3H); 6.25 dd (J = 10, 2 Hz, 1H); 6.35 d (J = 2 Hz, 1H); 6.88 dd (J = 8, 1.5 Hz, 1H); 6.98 d (J = 1.5 Hz, 1H); 7.05 d (J = 8 Hz, 1H); 8.04 d (J = 10 Hz, 1H); 9.52 s (wide)(1H); 10.72 s (wide).

b) 6-[3-(3,4-dimethoxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

was obtained by reacting 3-(3,4-dimethoxyphenyl)amino-4-nitrophenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

1H-NMR (CDCl 3 ): δ = 1.40-1.52 ppm m (2H); 1.60-1.80 m (4H); 2.32 h (J = 7.5 Hz, 2H); 3.68 s (3H); 3.85 h (J = 7.5 Hz, 2H); 3.88 s (3H); 3.93 s (3H); 6.29 dd (J = 10, 1.5 Hz, 1H); 6.33 d (J = 1.5 Hz, 1H); 6.80 d (J = 1.5 Hz, 1H); 6.87 dd (J = 10, 1.5 Hz, 1H); 6.92 d (J = 10 Hz, 1H); 8.18 d (J = 10 Hz, 1H); 9.68 s (wide)(1H).

6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reacting 6-[3-(3,4-dimethoxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to general working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to general working instructions 3.

Temp. 116-118 °C.

Example 62

6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

was obtained by reacting 6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 158-161 °C.

Example 63

6-[[1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

a) 3-(3,4-methylenedioxyphenyl)amino-4-nitrophenol

0.86 g of 3-fluoro-4-nitrophenol and 2.25 g of 3,4-methylenedioxyaniline were mixed together and stirred at 120 °C for 5 h. The crude mixture was chromatographed on silica gel.

<1>H-NMR (D6-DMSO): δ = 6.02 ppm s (2H); 6.25 dd (J = 10, 2 Hz, 1H); 6.33 d (J = 2 Hz, 1H); 6.72 dd (J =8, 1.5 Hz, 1H); 6.87 d (J = 1.5 Hz, 1H); 7.05 d (J = 10 Hz, 1H); 8.18 d (J = 10 Hz, 1H); 9.52 s (wide)(1H).

b) 6-[3-(3,4-methylenedioxyphenyl)amino-4-nitrophenyl]oxyhexane acid methyl ester

was obtained by reacting 3-(3,4-methylenedioxyphenyl)amino-4-nitrophenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

Temp. 108-111 °C.

6-[[1-(3,4-methylenedioxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

was obtained by reaction of 6-[3-(3,4-methylenedioxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to the gen-

elle working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to the general working instructions 3. <1>H-NMR (CDCI3) : 5 = 1.43-1.55 ppm m (2H) ; 1.65-1.82 m (4H); 2.35 h (j = 7.5 Hz, 2H); 3.68 s (3H); 3.95 h (J = 7.5 Hz, 2H); 6.10 s (2H); 6.65 d (J = 1.5 Hz, 1H); 6.72-6.83 m (2H); 6.90 d (J = 10 Hz, 1H); 6.93 dd (J = 10, 1.5 Hz, 1H); 7.29-7.38 m (3H); 7.52-7.62 m (2H); 7.72 d (J = 10 Hz, 1H).

Example 64

6-[[1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid

was obtained by reacting 6-[[1-(3,4-methylenedioxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9.

Temp. 130 °C.

Example 65

6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

a) 3-(3,4,5-trimethoxyphenyl)amino-4-nitrophenol

3.7 g of 3-fluoro-4-nitrophenol and 4.76 g of 3,4,5-trimethoxy-aniline were mixed together and stirred at 100 °C for 10 h. After cooling, the mixture was taken up in ethyl acetate and water and extracted three times with ethyl acetate. The combined organic phases were extracted three times with 1 N aqueous hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated as far as possible in vacuo. The product was leached with diisopropyl ether.

<1>H-NMR (De-DMSO): δ = 3.70 ppm s (3H); 3.80 s (6H); 6.28 dd (J = 10, 2 Hz, 1H); 6.53 d (J = 2 Hz, 1H); 6.70 s (2H); 8.05 d (J = 10 Hz, 1H); 9.50s (wide)(lH); 10.71 s (wide).

b) 6-[4-nitro-3-[(3,4,5-trimethoxyphenyl)amino]phenyl]oxyhexane acid methyl ester

was obtained by reaction of 4-nitro-3-[(3,4,5-trimethoxyphenyl)-amino]phenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

<1>H-NMR (CDCl3): δ = 1.40-1.53 ppm m (2H); 1.60-1.82 m (4H); 2.32

t (J = 7.5 Hz, 2H) ; 3.67 s (3H}.*'3.85 s- (6H); 3.88 t (J = ;7.5 Hz, 2H); 3.90 s (3H); 6.30 dd (J = 10, 1.5 Hz, 1H); 6.50 d (J = 1.5 Hz, 1H); 6.52 s (2H); 8.18 d (J = 10 Hz, 1H); 9.68 .s (broad) (1H).. ;6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;was obtained by reaction of 6 -[4-nitro-3-[(3,4,5-trimethoxy-phenyl)amino]phenyl]oxyhexanoic acid methyl ester according to general working instructions 1 and with subsequent cyclization with triethyl orthobenzoate according to general working instructions 3. ;Mp. 128 -130 ° C. ; Example 66 ; 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid ; was obtained by reaction of 6-[ [2-phenyl-1-(3,4,5-trimethoxy-phenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general working instruction 9. ;M.P. 198-201 °C.;Example 67 ;6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester; was obtained by reacting 6-[[2-phenyl-1-( 3,4,5-trimethoxy-phenyl)-1H-benzimide azol-6-yl] oxy] hexanoic acid with isopropanol according to the general work instructions 10. ;Mp. 98-101 °C. ;Example 68 ;6-[[1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;a) N,N-dimethyl-N'- (5-Chloro-2-nitrophenyl)benzene-1,4-diamine was prepared analogously to 5-chloro-2-nitrophenyl-m-tolylamine from 1-chloro-3,4-dinitrobenzene and N,N-dimethyl-p- phenylenediamine. 3-NMR (CDCl 3 ): δ = 3.01 ppm s (6H); 6.63 dd (J = 10, 2 Hz, 1H); 6.80 d (broad)(J = 10 Hz, 2H); 6.97 d (J = 2 Hz, 1H); 7.14 d (J = 10 Hz, .2H); 8.14 d (J = 10 Hz, 1H); 9.42 s (wide) (1H) . b) N,N-dimethyl-N1 - <5-methoxy-2-nitrophenyl)benzene-1,4-diamine 24.9 g N,N-dimethyl-N'-(5-chloro-2-nitrophenyl)benzene- 1,4-diamine was added to a solution of 8 g sodium in 200 ml methanol and the mixture heated to 120 °C for 9 h in an autoclave. After cooling, suction was carried out from the crystalline product. <1>H-NMR (CDCl 3 ) : δ = 3.00 ppm s (6H); 3.70 s (3H); 6.25 dd (J = 10, 2 Hz, 1H); 6.34 d (J = 2 Hz, 1H); 6.78 d (J = 10 Hz, 2H); 7.14 d (J = 10 Hz, 2H); 8.16 d (J = 10 Hz, 1H); 9.67s (wide)(1H). c) 6-methoxy-1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazole was prepared by reaction of N,N-dimethyl-N'-(5-methoxy-2-nitrophenyl )benzene-1,4-diamine according to the general working instructions 1, subsequent reaction of the crude diamine with trimethylorthobenzoate according to the general working instructions 3 and subsequent heating of the crude product with 6 N aqueous hydrochloric acid for 1 h until reflux. After alkalinization of the reaction mixture with aqueous sodium hydroxide, it was extracted with ethyl acetate, dried over sodium sulfate and concentrated in vacuo. <1>H-NMR (CDCl3) : δ = 3.04 ppm s (6H); 3.80 s (3H); 6.68 d (J = 2 Hz, 1H); 6.78 d (J = 10 Hz, 2H); 6.95 dd (J = 10, 2 Hz, 1H); 7.17 d (J = 10 Hz, 2H); 7.25-7.33 m (3H); 7.56-7.64 m (2H); 7.74 d (J = 10 Hz, 1H). ;d) 6-hydroxy-1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazole ;was obtained by reacting 6-methoxy-1-[4-(N,N-dimethylamino) )-phenyl]-2-phenyl-1H-benzimidazole according to the general working instruction 6. ;<1>H-NMR (De-DMSO): δ = 2.98 ppm s (6H); 6.48 d (J = 2 Hz, 1H); 6.78 dd (J = 10, 2 Hz, 1H); 6.83 d (J = 10 Hz, 2H); 7.17 d (J = 10 Hz, 2H); 7.30-7.38 m (3H); 7.50-7.57 m (3H); 9.32 s (wide)(1H). ;6- [ [1- [4- (N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;was obtained by reacting 6-hydroxy-1-[4- (N,N-dimethylamino)-phenyl]-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instruction 8. ;<1>H-NMR (CDC13) : 6 = 1.43-1.57 ppm m (2H); 1.64-1.85 m (4H); 2.33 h (J = 7.5 Hz, 2H); 3.05 s (6H); 3.67 s (3H); 3.93 h (J = 7.5 Hz, 2H); 6.65 d (J = 2 Hz, 1H); 6.76 d (J = 10 Hz, 2H); 6.93 dd (J = 10, 2 Hz, 1H); 7.14 d (J = 10 Hz, 2H); 7.23-7.27 m (3H); 7.62 dd (J = 10, 1.5 Hz, 2H); 7.74 d (J = 10 Hz, 1H). ;Example 69 ;6-[[1-[4- (N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid ;was obtained by reaction of 6-[[1- [4-(N,N-Dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9. ;M.P. 210-213 °C. ;Example 70 ;6-[[1-(4-biphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;a) 5-chloro-2-nitrophenyl-4-biphenylamine ;became analogous with 5-chloro-2-nitrophenyl-m-tolylamine prepared from 1-chloro-3,4-dinitrobenzene and 4-biphenylamine. It was purified by means of chromatography on silica gel. ;<1>H-NMR (CDCl 3 ): δ = 6.76 dd (J = 10, 2 Hz, 1H); 7.26 d (J = 2 Hz, 1H); 7.35 d (J = 8 Hz, 1H); 7.32-7.52m (4H); 7.60-7.72m (4H); 8.19 d (J = 10 Hz, 1H); 9.60 s (wide)(1H). ;b) 5-methoxy-2-nitrophenyl-4-biphenylamine ;was prepared analogously to 5-methoxy-2-nitrophenyl-m-tolylamine from ;5-chloro-2-nitrophenyl-4-biphenylamine and sodium methanolate. ; 150-154 °C. ;b) 1-(4-biphenyl)-6-methoxy-2-phenyl-1H-benzimidazole was obtained by reaction of 5-methoxy-2-nitrophenyl-4-biphenylamine according to general working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to general working instructions 3. M.p. 140-144 °C. c) 1-(4-biphenyl)-6-hydroxy-2-phenyl-1H-benzimidazole was obtained by reacting 1-(4-biphenyl)-6-methoxy-2-phenyl-1H-benzimidazole according to the general work instructions 6. ;Smp. 312 °C. ;6-[[1-(4-biphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;was obtained by reacting 1-(4-biphenyl)-6-hydroxy-2- phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;Mp. 106-108 °C. Example 71 6-[[1-(4-biphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[1-(4-biphenyl)-2- phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general working instruction 9. ;<1>H-NMR (D6-DMSO): 6 = 1.35-1.78 ppm m (6H); 2.20 h (J = 7.5 Hz, 2H); 3.96m (2H); 6.72 d (J = 2 Hz, 1H); 6.97 dd (J = 10, 2 Hz, 1H); 7.32-7.58 m (10H), 7.69 d (J = 10 Hz, 1H); 7.80 d (J = ;8 Hz, 2H); 7.89 d (J = 10 Hz, 2H) . ;Example 72 ;6-[[1-(2-naphthyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;a) 3-(2-naphthylamino)-4-nitrophenol ;3 g 3-Fluoro-4-nitrophenol and 8.2 g of 2-naphthylamine were mixed together and stirred at 180 °C for 8 h. The crude mixture was taken up in chloroform and washed with 2 N aqueous hydrochloric acid. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. ;<1>H-NMR (D6-DMSO) : δ = 6.02 ppm s (2H) ; 6.25 dd (J = 10, 2 Hz, 1H); 6.33 d (J = 2 Hz, 1H); 6.72 dd (J = 8, 1.5 Hz, 1H); 6.87 d (J = 1.5 Hz, 1H); 7.05 d (J = 10 Hz, 1H); 8.18 d (J = 10 Hz, 1H); 9.52 s (wide) (1H). , ;b) 6-[3-(2-naphthyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester was obtained by reacting 3-(2-naphthylamino)-4-nitrophenol with ;6-bromohexanoic acid methyl ester according to the general work instructions 8. ;<1>H-NMR (CDCl 3 ) : δ = 1.35-1.49 ppm m (2H) ; 1.60-1.80 m (4H); 2.30 h (J = 7.5 Hz, 2H); 3.64 s (3H); 3.84 h (J = 7.5 Hz, 2H); 6.35 dd (J = 10, 2 Hz, 1H); 6.62 d (J = 2 Hz, 1H); 7.43 dd (J = 10, 2 Hz, 1H); 7.48-7.57 m (2H); 7.75 d (J = 2 Hz, 1H); 7.78-7.90 m (2H); 7.91 d (J = 10 Hz, 1H); 8.21 d (J = 10 Hz, 1H); 9.92 s (wide)(1H). ;6-[[1-(2-naphthyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;was obtained by reacting 6-[3-(2-naphthylamino)-4-nitrophenyl ]-oxyhexanoic acid methyl ester according to the general working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to the general working instructions 3. ;M.P. 111-114 °C. Example 73 6-[[1-(2-naphthyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[1-(2-naphthyl)-2- phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9. ;Mp. 170-175 °C. ;Example 74 ;6-[[1-(2-fluorenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;a) 3-(2-fluorenylamino)-4-nitrophenol ;2, 17 g of 3-fluoro-4-nitrophenol and 5 g of 2-aminofluorene were mixed together and stirred at 140 °C for 9 h. The crude mixture was taken up in ethyl acetate and water and washed with 1 N aqueous hydrochloric acid. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed three times with 2 N aqueous hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate and vacuum. The residue was chromatographed on silica gel. ;<1>H-NMR (De-DMSO) : 6 = 3.96 ppm s (2H) ; 6.30 dd (J = 10, 2 Hz, ;1H); 6.52 d (J = 2 Hz, 1H); 7.28-7.45 m (3H); 7.57s (wide)(1H); 7.60 d (J = 8 Hz, 1H); 7.92 d (J = 8 Hz, 1H); 7.98 d (J = 8 Hz, '1H); 8.10 d (J = 10 Hz, 1H); 9.70 s (1H); 10.80 s (wide)(1H). ;b) 6-[3-(2-fluorenylamino)-4-nitrophenyl]oxyhexanoic acid methyl ester was obtained by reacting 3-(2-fluorenylamino)-4-nitrophenol ;with 6-bromohexanoic acid methyl ester according to the general work instructions 8. ;< 1>H-NMR (CDCl 3 ): δ = 1.38-1.50 ppm m (2H); 1.58-1.80 m (4H); 2.30 ;t (J = 7.5 Hz, 2H); 3.65 s (3H); 3.84 h (J = 7.5 Hz, 2H); 3.95 s (2H); 6.31 dd (J = 10, 2 Hz, 1H); 6.53 d (J = 2 Hz, 1H); 7.33 h (J = 8 Hz, 2H); 7.42 h (J = 8 Hz, 1H); 7.47 s (1H); 7.58 d (J = 8 Hz, 1H); 7.80 d (J = 8 Hz, 1H); 7.83 d (J = 8 Hz, 1H); 8.21 d (J = 10 Hz, 1H); 9.87 s (wide) (1H) . ;6-[[1-(2-fluorenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;was obtained by reacting 6-[3-(2-fluorenylamino).-4 -nitrophenyl]oxyhexanoic acid methyl ester according to the general working instructions 1 and with subsequent cyclization with triethylorthobenzoate according to the general working instructions 3. ;Mp. 125-128 °C. ;Example 75 ;6-[[1-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;a) Ethyl-(3-trifluoromethyl)benzimidate hydrochloride ;9.7 ml of 3-(trifluoromethyl)benzonitrile was dissolved in 12 ml of ethanol and the solution saturated with HCl gas while cooling in an ice bath. After 72 h, suction was carried out from the precipitated product. The product was washed with diethyl ether. ; 131-133 °C (decomp.). ;b) 5-methoxy-2-nitrophenyldiphenylamine ;A solution of 2 g of 3-fluoro-4-nitroanisole in 16 ml ;aniline was stirred at 140 °C for 24 h. After cooling, it was taken up in ethyl acetate and extracted with 2 N aqueous hydrochloric acid. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. ;<X>H-NMR (CDCl 3 ) : 6 = 3.72 ppm s (3H) ; 6.36 dd (J = 10, 2 Hz, 1H); 6.57 d (J = 2 Hz, 1H); 7.22-7.33 m (3H); 7.44 dd (J = 8.8 Hz, 2H); 8.18 d (J = 10 Hz, 1H); 9.78s (wide)(1H). ;c) 4-methoxy-N<2->phenyl-o-phenylenediamine ;was obtained by reaction of 5-methoxy-2-nitrophenyldiphenylamine in ;according to the general working instructions 1. ;<X>H-NMR (CDCI3): δ = 3.42 ppm s (broad) (2H); 3.72 s (3H); 5.33 s (wide)(lH); 6.56 dd (J = 10, 2 Hz, 1H); 6.76 d (J = 10 Hz, 1H); 6.79 d (J = 2 Hz, 1H); 6.82-6.90 m (3H); 7.25 dd (J = 8.8 Hz, 2H) . ;d) 6-methoxy-1-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazole was obtained by reaction of 4-methoxy-N<2->phenyl-o-phenylenediamine; with ethyl-(3 -trifluoromethyl)benzimidate hydrochloride according to the general work instructions 4. ;Mp. 138-140? C. e) 6-hydroxy-1-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazole was obtained by reacting 6-methoxy-1-phenyl-2-[3-(trifluoromethyl)f enyl]-1H-benzimidazole according to the general working instructions 7. ;<X>H-NMR (D6-DMSO) : δ = 6.60 ppm d (J = 2 Hz, 1H); 6.99 dd (J = 10, 2 Hz, 1H); 7.50-7.89 m (10H). ;6-[[1-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester; was obtained by reacting 6-hydroxy-1-phenyl-2-[3 -(trifluoromethyl)phenyl]-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;Mp. 68-70 °C. Example 76 6-[[l-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester was obtained by reaction of 6-hydroxy-1-phenyl-2 -[3-(trifluoromethyl)phenyl]-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8. ;Mp. 96-98 °C. ;Example 77 ;6-[[l-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid ;was obtained by reaction of 6-[[1-phenyl-2 -[3-(trifluoromethyl)-phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to general working instructions 9. ;<1>H-NMR (D6-DMSO): 5 = 1.38-1 .80 ppm m (6H); 2.27 h (J = 7.5 Hz, 2H); 3.98 h (J = 7.5 Hz, 2H); 6.70 d (J = 2 Hz, 1H); 7.02 dd (J = 10, 2 Hz, 1H); 7.48-7.88m (9H); 7.77 d (J = 10 Hz, 1H); 11.94 s (wide)(1H). ;Example 78 ;6-[[l-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexan-l-ol ;was obtained by reaction of 6-[[l -phenyl-2-[3-(trifluoromethyl)-phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to general working instructions 11. ;<1>H-NMR (CDC13) : 5 = 1.38 -1.68 ppm m (6H); 1.75-1.87 m (2H); 3.60-3.72 m (2H); 3.94 h (J = 7.5 Hz, 2H); 6.69 d (J = 2 Hz, 1H); 6.99 dd (J = 10, 2 Hz, 1H); 7.25-7.35 m (2H); 7.40 dd (J = ;8.8 Hz, 1H); 7.50-7.61 m (4H); 7.68 d (broad)(J = 8 Hz, 1H); 7.78 d (J = 10 Hz, 1H); 7.83 s (wide)(1H). ;Example 79 ;6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;a) 2-(3-chlorophenyl)-6-methoxy-1- phenyl-1H-benzimidazole was obtained by reacting 4-methoxy-N<2->phenyl-o-phenylenediamine with ethyl 3-chlorobenzimidate hydrochloride (prepared according to: DeWolfe and Augustine; J. Org. Chem.; 30; 699) in accordance with the general work instructions 4. ;Smp. 149-151 °C. b) 2-(3-chlorophenyl)-6-hydroxy-1-phenyl-1H-benzimidazole was obtained by reacting 2-(3-chlorophenyl)-6-methoxy-1-phenyl-1H-benzimidazole according to the general work instructions 7. Smp. 199-202 °C. ;6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;was obtained by reaction of 2-(3-chlorophenyl)-6-hydroxy-1- phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;Mp. 69-72 °C. ;Example 80 ;6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester ;was obtained by reaction of 2-(3-chlorophenyl)-6-hydroxy -1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8. ;Mp. 98-100 °C. Example 81 6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[2-(3-chlorophenyl)-1- phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instructions 9. ;Mp. 137-140 °C. Example 82 6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol was obtained by reacting 6-[[2-(3- chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general working instructions 11. ;<1>H-NMR (CDC13) : δ = 1.40-1.70 ppm m (6H ); 1.75-1.86 m (2H); 3.67 h (J = 7.5 Hz, 2H); 3.93 h (J = .7.5 Hz, 2H); 6.69 d (J = 2 Hz, 1H); 6.99 dd (J = 10, 2 Hz, 1H); 7.20 dd (J = 8.8 Hz, 1H); 7.26- ;7.38 m (4H); 7.47-7.58 m.OH); 7.60 dd (J = 2.2 Hz, 1H); 7.76 d (J = 10 Hz, 1H) ; Example 83 ; 6-[[2-(4-Chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;a) Ethyl -4-chlorobenzimidate hydrochloride; 10 g of 4-chlorobenzonitrile were suspended in 12 ml of ethanol and dissolved by the addition of diethyl ether. During cooling in an ice bath, saturation with HCl gas was carried out. After 72 h, extraction was carried out from the precipitated product. The product was washed with diethyl ether. ; 173-174 °C (decomp.). ;a) 2-(4-chlorophenyl)-6-methoxy-1-phenyl-1H-benzimidazole was obtained by reaction of 4-methoxy-N<2->phenyl-o-phenylenediamine ;with ethyl 4-chlorobenzimidate hydrochloride according to the general work instructions 4. ;Smp. 162-164 °C. b) 2-(4-chlorophenyl)-6-hydroxy-1-phenyl-1H-benzimidazole was obtained by reacting 2-(4-chlorophenyl)-6-methoxy-1-phenyl-1H-benzimidazole according to the general work instructions 7. Smp. 24 6-250 °C. ;6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid methyl ester ;was obtained by reaction of 2-(4-chlorophenyl)-6-hydroxy-1- phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;Mp. 8 6-87 °C. ;Example 84 ;6-t[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester ;was obtained by reaction of 2-(4-chlorophenyl)-6-hydroxy -1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8. ;Mp. 124-126 °C.. Example 85 6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[2-(4-chlorophenyl)-1- phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general working instruction 9. ;<1>H-NMR (D6-DMSO): 6 = 1.35-1.48 ppm m (2H); 1.50-1.62 m (2H); 1.64-1.77 m (2H); 2.23 h (J = 7.5 Hz, 2H); 3.91 h (J = 7.5 Hz, 2H); 6.64 d (J = 2 Hz, 1H); 6.96 dd (J = 10, 2 Hz, 1H); 7.38-7.50 m (6H); 7.52-7.65 m (3H); 7.70 d (J = 10 Hz, 1H). ;Example 86 ;6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol ;was obtained by reacting 6-[[2-(4- chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general working instructions 11. ;<1>H-NMR (CDC13) : δ = 1.38-1.68 ppm m (6H ); 1.74-1.85 m (2H); 3.67 ;t (broad) (J = 7.5 Hz, 2H) ; 3.94 h (J = 7.5 Hz, 2H); 6.68 d (J = ;2 Hz, 1H); 6.98 dd (J = 10, 2 Hz, 1H); 7.22-7.35 m (5H); 7.47 d (J = 8 Hz, 2H); 7.49-7.59 m (2H); 7.73 d (J = 10 Hz, 1H). ;Example 87 ;6-[[2-(3-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;a) 6-methoxy-2-(3-methylphenyl)-1- phenyl-1H-benzimidazole was obtained by reacting 4-methoxy-N<2->phenyl-o-phenylenediamine with ethyl 3-methylbenzimidate hydrochloride (prepared according to: DeWolfe and Augustine; J. Org. Chem.; 30; 699) in accordance with the general work instructions 4. ;Smp. 156-158 °C. b) 6-hydroxy-2-(3-methylphenyl)-1-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-2-(3-methylphenyl)-1-phenyl-1H-benzimidazole according to the general work instructions 7. <1>H-NMR (D6-DMSO): 6 = 2.23 ppm s (3H); 6.52 d (J = 2 Hz, 1H); ;6.80 dd (J = 10, 2 Hz, 1H); 7.18 s (broad)(3H); 7.35-7.52 m (3H); 7.50-7-, 63m (4H); 9.28s (wide) (1H) . ;6-[[2-(3-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester was obtained by reaction of 6-hydroxy-2-(3-methylphenyl)"-1- phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;M.P. 82-84 °C.;Example 88 ;6-[[2-(3-methylphenyl)-1-phenyl-1H-benzimidazole- 6-yl]oxy]hexanoic acid isopropyl ester was obtained by reacting 6-hydroxy-2-(3-methylphenyl)-1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8. ;<X> H-NMR (CDCl 3 ) : δ = 1.22 ppm d (J = 7.5 Hz, 6H); 1.38-1.56 m (2H); 1.62-1.85 m (4H); 2 .30 h (J = 7.5 Hz, 2H); 2.30 s (3H); 3.93 h (J = 7.5 Hz, 2H); 5.00 sp (J = 7.5 Hz, 1H); 6.68 d (J = 2 Hz, 1H); 6.95 dd (J = 10, 2 Hz, 1H); 7.13 s (broad)(3H); 7.31 dd (J = 8 , 2 Hz, 2H); 7.42-7.57 m (4H); 7.76 d (J = 10 Hz, 1H). ;Example 89 ;6-[[2-(3-methylphenyl)-1- phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid; was obtained by reacting 6-[[2-(3-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]h Hexanoic acid methyl ester according to the general working instruction 9. ;<1>H-NMR (D6-DMS0): δ = 1.35-1.49 ppm m (2H); 1.50-1.63 m (2H); 1.64-1.78 m (2H); 2.22 h (J = 7.5 Hz, 2H); 2.24 s (3H); 3.92 h (J = 7.5 Hz, 2H); 6.62 d (J = 2 Hz, 1H); 6.95 dd (J = 10, 2 Hz, 1H); 7.18 s (broad)(3H); 7.37-7.42 m (3H); 7.51-7.65 m (3H); 7.67 d (J = 10 Hz, 1H); 11.90 s (wide)(1H). ;Example 90 ;6-[[2-(3-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane-1-61 ;was obtained by reaction of 6-[[2-(3- methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to general work instructions 9. ;Mp. 92-94 °C. ;Example 91 ;6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;a) 6-methoxy-2-(4-methylphenyl)-1- phenyl-1H-benzimidazole was obtained by reacting 4-methoxy-N<2->phenyl-o-phenylenediamine with ethyl 4-methylbenzimidate hydrochloride (prepared according to: DeWolfe and Augustine; J. Org. Chem.; 30; 699) in accordance with the general work instructions 4. ;Smp. 150-152 °C. b) 6-hydroxy-2-(4-methylphenyl)-1-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-2-(4-methylphenyl)-1-phenyl-1H-benzimidazole according to the general work instructions 7. Smp. 257-264 °C. ;6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;was obtained by reacting 6-hydroxy-2-(4-methylphenyl)-1- phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;Mp. 99-102 °C. Example 92 6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester was obtained by adding 6-hydroxy-2-(4-methylphenyl )-1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general work instructions 8. ;Mp. 107-109 °C. ;Example 93 ;6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid ;was obtained by reacting 6-[[2-(4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instruction 9. ;1H-NMR (D6-DMSO): δ = 1.33-1.49 ppm m (2H); 1.50-1.62 m (2H); 1.64-1.77 m (2H); 2.22 h (J = 7.5 Hz, 2H-); 2.30 s (3H); 3.90 h (J = 7.5 Hz; 2H); 6.62 d (J = 2 Hz, 1H); .6.94 dd (J = 10, -2 Hz, ;1H); 7.15 d (J = 8 Hz, 2H); 7.36 d (J = 8 Hz, 2H); 7.40 dd (J = 8, 1.5 Hz, 2H); 7.52-7.62 m (3H); 7.68 d (J = 10 Hz, 1H). Example 94 6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol was obtained by reaction of 6-[[2-(4- methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instruction 11. ;Mp. 150-152 °C. ;Example 95 ;6-[[l-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;a) 6-methoxy-1-phenyl-2-(4-pyridinyl) )-1H-benzimidazole; 0.4 g of 4-methoxy-N<2>.-phenyl-o-phenylenediamine was dissolved in ;8 ml of N,N-dimethylformamide, and the solution was supplied with 0.7 g of ethyl-2- ethoxy-1,2-dihydroquinoline-1-carboxylate and 0.34 g iso-nicotinic acid. The mixture was stirred for 16 h at 100 °C, water was added after cooling, extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. After chromatographic purification on silica gel, the amide was taken up in 5 ml of 6 N aqueous hydrochloric acid and heated for 3 h until reflux. After cooling, it was stirred in saturated sodium bicarbonate solution, extracted three times with ethyl acetate, the combined extracts washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. <1>H-NMR (CDCl 3 ): δ = 3.80 ppm s (3H); 6.66 ppm d (J = 2 Hz, 1H); 7.02 dd (J = 10, 2 Hz, 1H); 7.32-7.38m (2H); 7.42 dd (J = 8, 1.5 Hz, 2H); 7.54-7.62 m (3H); 7.79 d (J = 10 Hz, 1H); 8.53 d (broad)(J = 6 Hz, 2H). b) 6-hydroxy-1-phenyl-2-(4-pyridinyl)-1H-benzimidazole was prepared by reacting 6-methoxy-1-phenyl-2-(4-pyridinyl)-1H-benzimidazole according to the general working instructions 7. <1>H-NMR (CD3OD): δ = 6.52 ppm d (J = 2 Hz, 1H); 6.82 dd (J = 10, 2 Hz, 1H); 7.28-7.33 m (2H) ; 7.39 dd (J = 8, 1.5 Hz, 2H); 7th, 4 9-7.57 m (4H); 8.40 d (broad)(J = 6 Hz, 2H). 6-[[1-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane-acid methyl ester was prepared by reacting 6-hydroxy-1-phenyl-2-(4- pyridinyl)-1H-benzimidazole according to the general work instructions 8. ;Mp. 100-103 °C. Example 96 6-[[1-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid was prepared by reaction of 6-[[1-phenyl-2-(4-pyridinyl )-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instruction 9. ;Mp. 160-162 °C. ;Example 97 ;6-[(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester ;a) 1,2-diphenyl-6-hydroxy-5-nitro-1H- benzimidazole; b) 1,2-diphenyl-6-hydroxy-7-nitro-1H-benzimidazole; c) 1,2-diphenyl-6-hydroxy-5,7-dinitro-1H-benzimidazole; 5 g 1,2- diphenyl-6-hydroxy-1H-benzimidazole was dissolved in 45 ml of glacial acetic acid and supplied dropwise at 10-15 °C with a solution of 1.67 g of potassium nitrite in 15 ml of water. The solution was kept in an ice bath for 2 h and then at 20 °C for 2 h with stirring, the reaction mixture was concentrated in vacuo and purified by chromatography on silica gel. ;a) <X>H-NMR (CDCl3): δ = 6.83 ppm s (1H); 7.25-7.44 m (5H); 7.52-7.60 m (5H); 8.66 s (1H); 10.78 s (1H) . b) <1>H-NMR (D6-DMSO): δ = 7.05 ppm d (J = 10 Hz, 1H); 7.30-7.53 m (10H); 7.82 d (J = 10 Hz, 1H); 10.83 s (1H). c) <1>H-NMR (D6-DMS0): δ = 7.32-7.58 ppm m (10H); 8.67 s (1H). ;6-[(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester ;was obtained by reacting 1,2-diphenyl-6-hydroxy-5-nitro-1H- benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8. ;Mp. 123 °C. Example 98 6-[(1,2-diphenyl-5.-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester was obtained by reacting 1,2-diphenyl-6-hydroxy-5-nitro -1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general working instructions 8. ;M.P. 115-117 °C. ;Example 99 ;6-[(1,2-diphenyl-7-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester ;was obtained by reacting 1,2-diphenyl-6-hydroxy-7-nitro -1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;M.P. 110-112 °C. Example 100 6-[(1,2-diphenyl-7-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester was obtained by reacting 1,2-diphenyl-6-hydroxy-5- nitro-1H-benzimidazole with 6-brpmhexanoic acid isopropyl ester according to the general working instructions 8. ;Mp. 88 °C. ;Example 101 ;6-[(7-amino-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester ;340 mg 6-[(1,2-diphenyl-7-nitro-1H- Benzimidazol-6-yl)oxy]hexanoic acid methyl ester was hydrated in ethanol with Raney nickel in an autoclave at 50°C and at normal pressure. After completion of hydrogen absorption, filtration was carried out from the catalyst and concentration in vacuum. ; 113-115 °C. Example 102 6-[(7-amino-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester was obtained analogously to the instructions given in example 101 by reaction of .6-[( 1,2-Diphenyl-7-nitro-1H-benzimidazol-6-yl)-oxy]hexanoic acid isopropyl ester. ;<1>H-NMR (CDCl 3 ) : δ = 1.22 ppm d (J = 7.5 Hz, 6H); 1.43-1.88 m (6H); 2.30 h (J = 7.5 Hz, 2H); 4.04 h (J = 7.5 Hz, 2H); 5.00 sp (J = 7.5 Hz, 1H); 6.97 d (J = 7.5 Hz, 1H); 7.20-7.33 m (4H); 7.42-7.53 m (7H). Example 103 6-[(5,7-dinitro-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane acid methyl ester was obtained by reaction of 5,7-dinitro-1,2-diphenyl -6-Hydroxy-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8. ;Mp. 88-91 °C. Example 104 6-[(5,7-dinitro-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-acid isopropyl ester was obtained by reaction of 5,7-dinitro-1,2-diphenyl -6-Hydroxy-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to the general work instructions 8. ;Mp. 92-93 °C. ;Example 105 ;6-[[5-(acetylamino)-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester ;a) 5-fluoro-2,4-dinitrophenol ;0.41 g 1 ,3-difluoro-4,6-dinitrobenzene was dissolved in 8 ml of 0.5 N aqueous sodium hydroxide and heated for 2 h until reflux. After cooling, it was diluted with water and extracted three times with diethyl ether. The aqueous phase was made acidic by the addition of 1 N hydrochloric acid and extracted with diethyl ether. The organic phase was dried over sodium sulfate and concentrated in vacuo.. ;<1>H-NMR (CDCl3): δ = 7.10 ppm d (J = 12 Hz, 1H); 9.03 d (J = 8 Hz, 1H); 11.10 s (1H). ;b) 2,4-dinitro-5-hydroxydiphenylamine ;To the suspension of 50 mg of 5-fluoro-2,4-dinitrophenol in ;0.5 ml of ethanol, 100 ul of aniline was added, stirred for 30 min and the mixture allowed to stand for 15 h. Suction was carried out, the solid was washed with 1 N aqueous hydrochloric acid and dried in a vacuum. ;<X>H-NMR (CDCl 3 ): δ = 6.58 ppm s (1H); 7.31 d (J = 10 Hz, 2H); 7.39 dd (J = 10, 10 Hz, 1H); 7.51 dd (J = 10, 10 Hz, 2H); 9.20 s ;(1H); 9.90 s (wide)(lH); 10.97 s (wide)(1H). ;c) Acetic acid-(2,4-dinitro-5-phenylamino)phenyl ester ;To 275 mg of 2,4-dinitro-5-hydroxydiphenylamine in 1 ml of pyridine, 0.11 ml of acetic anhydride was added and stirring was carried out for 30 min in an ice bath and then for another 1 h at 20 °C. After dilution with ethyl acetate, it was washed three times with ice-cold 1 N aqueous hydrochloric acid, once with saturated potassium bicarbonate solution and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. ;<X>H-NMR (CDCl 3 ) : δ = 2.34 ppm s (3H) ; 6.80 s (1H); 7.32 d (J = ;10 Hz, 2H); 7.40 dd (J = 10, 10 Hz, 1H); 7.52 dd (J = 10, 10 Hz, 2H); 9.21 s (1H); 9.95s (wide)(1H). d) Acetic acid-(1,2-diphenyl-6-hydroxy-1H-benzimidazol-5-yl)amide was obtained by reacting acetic acid-(2,4-dinitro-5-phenyl-amino)phenyl ester according to the general work instructions 1 and with subsequent reaction with trimethylorthobenzoate according to the general work instructions 3. ;<1>H-NMR (CDCI3) : 6 = 2.26 ppm s (3H) ; 6.88 s (1H); 7.22-7.36 m (5H); 7.42-7.53 m (5H); 7.61 s (1H); 8.43 s (wide)(1H). ;6-[[5-(acetylamino)-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester ;was obtained by reacting acetic acid-(1,2-diphenyl-6-hydroxy-1H- benzimidazol-5-yl)amide with 6-bromohexanoic acid methyl ester according to the general working instructions 8. M.p. 128-130 °C-. Example 106 6-[(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester was obtained by reacting 6-[(1,2-diphenyl-5-nitro -1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester according to the general working instructions 1. ;<1>H-NMR (CDCl 3 ) : δ = 1.23 ppm d (J = 7.5 Hz, 6H); 1.47-1.90 m (6H); 2.32 h (J = 7.5 Hz, 2H); 3.95 h (J = 7.5 Hz, 2H); 5.02 sp (J = 7.5 Hz, 1H); 6.60 s (1H); 7.20 s (1H); 7.22-7.33 m (5H); 7.43-7.58m (5H). ;Example 107 ;6-[[5-[[(4-bromophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1, 2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 4-bromobenzenesulfonic acid chloride according to the general working instructions 13. ;M.P. 173-175 °C. Example 108 6-[(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was obtained by reacting 6-[(1,2-diphenyl-5-nitro -1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester according to the general working instructions 1. ;<1>H-NMR (CDCl3) : 6 = 1.48-1.88 ppm (6H); 2.36 h (J = 7.5 Hz, 2H, CH2 = CO); 3.67 s (3H); 3.94 h (J = 7.5 Hz, 2H); 6.60 s (1H); 7.21 s (1H); 7.22-7.35 m (5H); 7.43-7.59 m (5H). ;Example 109 ;6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;6-[(5-amino-1, 2-Diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general working instructions 13. ;M.P. 157-159 °C. ;Example 110 ;6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1, 2-Diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general working instructions 13. M.p. 158-159 °C. ;Example 111 ;6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid ;was obtained by reacting 6-[[5 -[[(4-chlorophenyl)sulfonyl]-amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general work instruction 9. ;M.p. 201-203 °C. ;Example 112 ;6-[[1,2-diphenyl-5-[[(3-methylphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1, 2-Diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 3-methylbenzenesulfonic acid chloride according to the general working instructions 13. M.p. 149-151 °C. ;Example 113 ;6-[[1,2-diphenyl-5-[[(4-methylphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1, 2-Diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 4-methylbenzenesulfonic acid chloride according to the general working instructions 13. M.p. 139-141 °C. ;Example 114 ;6-[[1,2-diphenyl-5-[[(4-methoxyphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1, 2-Diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 4-methoxybenzenesulfonic acid chloride according to the general working instructions 13.. ;<1>H-NMR (CDCl3) : 5 = 1.25 ppm d (J = 7.5 Hz, 6H); 1.35-1.45 m (2H); 1.59-1.73 m (4H); 2.30 h (J = 7.5 Hz, 2H); 3.72 h (J = 7.5 Hz, 2H); 3.80 s (3H); 5.02 sp (J = 7.5 Hz, 1H); 6.50 s (1H) ; 6.85 d (J = 10 Hz, 2H); 6.99 s (1H); 7.25-7.35 m (5H); 7.45-7.52 m (5H); 7.74 d (J = 10 Hz, 2H); 7.99s (1H). ;Example 115 ;6-[[1,2-diphenyl-5-[[[(4-trifluoromethyl)phenyl]sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino -1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 4-trifluoromethylbenzenesulfonic acid chloride according to general working instructions 13. M.p. 170-171 °C. ;Example 116 ;6-[[5-[[[4-(acetylamino)phenyl]sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino -1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 4-ac.ethylaminobenzenesulfonic acid chloride according to the general working instructions 13. M.p. 100-102 °C. ;Example 117 ;6-[[5-[[bis(3-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1 ,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with 3-chlorobenzenesulfonic acid chloride according to the general working instructions 13. ;M.P. 163-167 °C. ;Example 118 ;6-[[1,2-diphenyl-5-[(propylsulfonyl)amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1,2-diphenyl-1H -benzimidazol-6-yl)oxy]-hexanoic acid isopropyl ester was reacted with propanesulfonic acid chloride according to the general working instructions 13. ;M.P. 126-128 °C. ;Example 119 ;6-[[5-[(benzylsulfonyl)amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[(5-amino-1,2-diphenyl-1H -benzimidazol-6-yloxy]-hexanoic acid isopropyl ester was reacted with benzenemethanesulfonic acid chloride according to the general working instructions 13. M.p. 137-138° C.; Example 120; 4-[(1,2-diphenyl-1H-benzimidazol-6-yl )oxy]methylbenzoic acid methyl ester - ;was prepared by reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 4-(bromomethyl)benzoic acid methyl ester according to the general working instructions 8. ;M.P. 180-184 °C. Example 121 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]methylbenzoic acid was prepared by reacting 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy] methylbenzoic acid methyl ester according to the general working instructions 9. ;<1>H-NMR (D6-DMSO): 6 = 5.12 ppm s (2H); 6.76 d (J = 2 Hz, 1H); 7.04 dd (J = 10, 2 Hz, 1H); 7.30-7.63 m (12H); 7.70 d (J = ;10 Hz, 1H); 7.89 d (J = 8 Hz, 2H). ;Example 122 ;4-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy] methyl benzoic acid methyl ester ;was prepared by reaction of 6-hydroxy-1-(3-methylphenyl)-2-phenyl-1H-benzimidazole with 4-(bromomethyl)benzoic acid methyl ester according to the general working instructions 8. ;Mp. 138-142 °C. ;Example 123 ;4-t[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]methyl-benzoic acid methyl ester ;was prepared by reacting 6-hydroxy-1-(4-methylphenyl) -2-phenyl-1H-benzimidazole with 4-(bromomethyl)benzoic acid methyl ester according to the general work instructions 8. ;Mp. 145-148 °C. ;Example 124 ;2-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid tert-butyl ester ;0.2 g [(1,2-diphenyl-1H- benzimidazol-6-yl)oxy]ethan-1-ol was suspended in 1.7 ml of toluene and 0.7 ml of tetrahydrofuran. To this was added 0.1 ml bromoacetic acid tert-butyl ester and 13 mg tetrabutylammonium hydrogen sulfate and 1.45 ml 32% sodium hydroxide and allowed to stir for 48 h. A further 0.1 ml bromoacetic acid tert-butyl ester was added and 13 mg of tetrabutylammonium hydrogensulphate and left the mixture in an ultrasonic bath for 48 h. It was then diluted with water and extracted three times with toluene. The combined organic phases were washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. ;<1>H-NMR (CDCl 3 ): δ = 1.43 ppm s (9H); 3.91 h (J = 6 Hz, 2H); 4.10 s (2H); 4.17 h (J = 6 Hz, 2H); 6.75 d (J = 2 Hz, 1H); 7.00 dd (J = 10, 2 Hz, 1H); 7.24-7.36 m (5H); 7.45-7.56 m (5H); 7.76 d (J = 10 Hz, 1H). Example 125 2-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid 50 mg 2-[2-[(1,2-diphenyl-1H-benzimidazol-6 -yl)oxy]-ethoxy]acetic acid tert-butyl ester was dissolved in 0.5 ml of trifluoroacetic acid and stirred for 48 h. It was then diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. ; 134-136 °C. ;Example 126 ;2-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid methyl ester ;35 mg 2-[2-[(1,2-diphenyl-1H- Benzimidazol-6-yl)oxy]-ethoxy]acetic acid was dissolved in 0.4 ml of N,N-dimethylformamide and treated with 29 mg of cesium carbonate and 50 µl of methyl iodide. The mixture was stirred for 20 h and then concentrated in vacuo and chromatographed on silica gel. ;<X>H-NMR (CDCl3) : = 3.73 ppm s (3H) ; 3.93 h (J = 6 Hz, 2H); 4.18 h (J = 6 Hz, 2H); 4.25 s (2H); 6.73 d (J = 2 Hz, 1H); 7.00 dd (J = 10, 2 Hz, 1H); 7.25-7.42 m (5H) ; 7.46-7.58 m (5H); 7.77 d (J = 10 Hz, 1H). ;Example 127 ;3-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]propanoic acid tert-butyl ester ;0.2 g [(1,2-diphenyl-1H- benzimidazol-6-yl)oxy]ethan-1-ol was suspended in 1.7 ml of toluene and 0.7 ml of tetrahydrofuran. To this was added 60 ul acrylic acid tert-butyl ester, 13 mg tetrabutylammonium hydrogen sulfate and 1.45 ml 32% sodium hydroxide and allowed to stir for 48 h. A further 60 ul acrylic acid tert-butyl ester and 13 mg tetrabutylammonium hydrogen sulfate were added and left the mixture for 48 h in an ultrasonic bath. It was then diluted with water and extracted three times with toluene. The combined organic phases were washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. .sup.-NMR (CDCl 3 ): δ = 1.45 ppm s (9H); 2.52 h (J = 8 Hz, 2H); 3.73-3.84 m (4H); 4.10 h (J = 6 Hz, 2H); 6.72 d (J = 2 Hz, 1H); 6.99 dd (J = 10, 2 Hz, 1H); 7.22-7.38 m (5H); 7.45-7.57 m (5H); 7.75 d (J = 10 Hz, 1H). Example 128 3-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]propanoic acid 50 mg 3-[2-[(1,2-diphenyl-1H-benzimidazol-6 -yl)oxy]-ethoxy]propanoic acid tert-butyl ester was dissolved in 0.5 ml of trifluoroacetic acid and stirred for 15 h. It was then diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. ;<X>H-NMR (D6-DMSO) : δ = 2.26 ppm t (J = 8 Hz, 2H); 3.60-3.70 m (4H); 3.98-4.06 m (2H); 6.65 d (J = 2 Hz, 1H); 6.94 dd (J = 10,, 2 Hz, 1H); 7.30-7.62 m (10H); 7.68 d (J = 10 Hz, 1H). Example 129 3-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]propanoic acid methyl ester 35 mg 3-[2-[(1,2-diphenyl-1H-benzimidazol -6-yl)oxy]-ethoxy]propanoic acid was dissolved in 0.4 ml of N,N-dimethylformamide, treated with 28 mg of cesium carbonate and 50 µl of methyl iodide and stirred for 30 h. It was then diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. Temp. 91-93 °C. ;Example 130 ;3-[3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propoxy]propanoic acid tert.-butyl ester ;0.2 g 3-[(1,2- diphenyl-1H-benzimidazol-6-yl)oxy]propan-1-ol was suspended in 1.7 ml of toluene and 0.7 ml of tetrahydrofuran. To this was added 60 ul acrylic acid tert-butyl ester, 13 mg tetrabutylammonium hydrogen sulfate and 1.47 ml 32% sodium hydroxide solution and allowed to stir for 48 h. added 60 ul of acrylic acid tert-butyl ester and 13 mg of tetrabutylammonium hydrogensulphate and allowed the mixture to stand for 48 h in an ultrasonic bath. It was then diluted with water and extracted three times with toluene. The combined organic phases were washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. ; 95-98 °C. ;Example 131 ;(E/Z)-5-(1,2-diphenyl-1H-benzimidazol-6-yl)pent-4-enoic acid methyl ester ;a) 1,2-diphenyl-6-methyl-1H-benzimidazole ;5.1 g of 5-methyl-2-nitrodiphenylamine was hydrated in 55 ml of ethanol according to the general working instructions 1. The crude product was reacted with trimethylorthobenzoate according to the general working instructions 3. ;Mp. 134-136 °C. b) 1,2-diphenyl-1H-benzimidazole-6-carbaldehyde 1 g of 1,2-diphenyl-6-methyl-1H-benzimidazole was suspended in 31 ml of 40% sulfuric acid and supplied with 13.5 g cerium ammonium nitrate. Stirring was allowed for 2.5 h at 80 °C, cooled to 20 °C and saturated aqueous sodium bicarbonate solution was carefully stirred in. The mixture was extracted three times with ethyl acetate, the combined extracts were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated to dryness in vacuo. The residue was chromatographed on silica gel. ;<X>H-NMR (CDCl1): δ = 7.30-7.42 ppm m (5H); 7.50-7.66m (5H); 7.81 d (J = 2 Hz, 1H); 7.89 dd (J = 8.2 Hz, 1H); 8.00 d (J = 8 Hz, 1H); 10.05 s (1H). (E/Z)-5-(1,2-diphenyl-1H-benzimidazol-6-yl)pent-4-enoic acid methyl ester was obtained by reacting 1,2-diphenyl-1H-benzimidazol-6-carbaldehyde with 3-carboxypropyltriphenylphosphonium bromide according to the general working instructions 12. ;<X>H-NMR (CDC13) : δ = 2.40-2.71 ppm m (4H) ; 3, 68 (3, 66) each s (3H); 5.56-5.64 (6.12-6.22) each m (1H); 6.50 d (J = 18 Hz, 1H); 6.58 d (broad)(J = 12 Hz, 1H); 7.12 (7.15) each s (wide)(lH); 7.25-7.40 m (6H); 7.45-7.62 m (5H); 7.80 (7.83) every d (J = ;8 Hz, 1H). Example 132 E-5-(1,2-diphenyl-1H-benzimidazol-6-yl)pent-4-enoic acid was obtained by reaction of (E/Z)-5-(1,2-diphenyl-1H -benzimidazol-6-yl)pent-4-enoic acid methyl ester according to the general working instructions 9. ;<:>H-NMR (CD3OD): δ = 2.26-2.43 ppm m (4H); 6.10-6.21 m (1H); 6.45 d (J = 18 Hz, 1H); 7.08 s (1H); 7.22-7.52m (11H); 7.59 d (J = ;8 Hz, 1H). ;Example 133 ;5-(1,2-diphenyl-1H-benzimidazol-6-yl)pentanoic acid methyl ester was obtained by reaction of (E/Z)-5-(1,2-diphenyl-1H-benzimidazol-6-yl) pent-4-enoic acid methyl ester according to the general working instructions 1. ;<X>H-NMR (CDCl3) : 6 = 1.63-1.72 ppm m (4H); 2.30-2.39 m (2H); 2.68-2.77 m (2H);. 3.65 s (3H); 7.04 s (wide)(lH); 7.17 dd (J = 8.2 Hz, 1H); 7.25-7.38m (5H); 7.45-7.60 m (5H); 7.79 d (J = 8 Hz, 1H) . Example 134 5-(1,2-diphenyl-1H-benzimidazol-6-yl)pentanoic acid was obtained by reacting 5-(1,2-diphenyl-1H-benzimidazol-6-yl)pentanoic acid methyl ester according to the general work instructions 9. ;Smp. 192-193 °C. Example 135 (E/Z)-6-(1,2-diphenyl-1H-benzimidazol-6-yl)hex-5-enoic acid methyl ester was obtained by reacting 1,2-diphenyl-1H-benzimidazol- 6-carbaldehyde with 4-carboxybutyltriphenylphosphonium bromide according to the general working instructions 12. ;<X>H-NMR (CDCl3) : 6 = 1.72-1.88 ppm m (2H) ; 2.20-2.42 m (4H); 3.65 (3.67) each s (3H, CH3) ; 5.57-5.68 (6.10-6.20) each m (1H); 6.48 d (J = 18 Hz, 1H); 6.56 d (broad)(J = 12 Hz, 1H); 7.12 (7.16) each s (wide)(1H); 7.25-7.38m (6H); 7.45-7.60 m (5H); 7.80 (7.84) each d (J = 8 Hz, 1H). Example 136 (E/Z)-6-(1,2-diphenyl-1H-benzimidazol-6-yl)hex-5-enoic acid was obtained by reaction of (E/Z)-6-(1,2- diphenyl-1H-benzimidazol-6-yl)hex-5-enoic acid methyl ester according to the general working instructions 9. ;<X>H-NMR (CDCl3) : 6 = 1.74-1.89 ppm m (2H); 2.22-2.43 m (4H); 5.58-5.68 (6.10-6.22) each m (1H); 6.47 d (J = 18 Hz, 1H); 6.55 d (broad)(J = 12 Hz, 1H); 7.11 (7.14) each s (wide)(1H); 7.25-7.40m (6H); 7.48-7.59 m (5H); 7.80 (7.85) each d (J = 8 Hz, 1H). ;Example 137 ;6-(1,2-diphenyl-1H-benzimidazol-6-yl)hexanoic acid methyl ester was obtained by reaction of (E/Z)-6-(1,2-diphenyl-1H-benzimidazol-6-yl) hex-5-enoic acid methyl ester according to the general working instructions 1. ;<1>H-NMR (CDCl3): δ = 1.32-1.43 ppm m (2H)'; 1.62-1.74 m (4H); 2.31 h (J = 7.5 Hz, 2H); 2.72 h (J = 7.5 Hz, 2H); 3.56 s (3H); 7.02 s (wide)(1H); 7.18 dd (J = 8.2 Hz, 1H); 7.27-7.38 m (5H); 7.45 -. 7.60m (5H); 7.80 d (J = 8 Hz, 1H). Example 138 6-(1,2-diphenyl-1H-benzimidazol-6-yl)hexanoic acid was obtained by reacting 6-(1,2-diphenyl-1H-benzimidazol-6-yl)hexanoic acid methyl ester according to the general working instructions 9. ;<1>H-NMR JCDC1-3) : 6 = 1.30-1 .^5 ppm m (2H) ; 1.54-1.74 m (4H); 2.32 h (J = 7.5 Hz, 2H); 2.70 h (J = 7.5 Hz, 2H); 7.02 s (bredf(lH) ; 7.20 dd (J = 8, 2 Hz, 1H); 7.25-7.38 m (5H); 7.42-7.60 m (5H); 7 .81 d (J = 8 Hz, 1H). ;Example 139 ;(E/Z)-7-(1,2-diphenyl-1H-benzimidazol-6-yl)hept-6-enoic acid methyl ester ;was obtained by reaction of 1,2-diphenyl-1H-benzimidazole-6-carbaldehyde with 5-carboxypentyltriphenylphosphonium bromide according to the general working instructions 12. ;^-NMR (CDCl3) : δ = 1.43-1.55 ppm m (2H) ; 1.58-1.72 m (2H); 2.18-2.38 m (4H); 3.65 (3.66) each s (3H, CH3) ; 5.58-5.68 (6, 12-6.22) each m (1H); 6.45 d (J = 18 Hz, 1H); 6.54 d (wide) (J = 12 Hz, 1H); 7.12 (7.14) each s (wide)(lH); 7.26-7.40 m (6H); 7.48-7.60 m (5H); 7.80 (7.83) each d (J = 8 Hz, 1H) Example 140 (E/Z)-7-(1,2-diphenyl-1H-benzimidazol-6-yl)hept-6-enoic acid was obtained by reaction of (E/Z)-7-(1, 2-diphenyl-1H-benzimidazol-6-yl)hept-6-enoic acid methyl ester according to the general work instructions 9. ;<X>H-NMR (D6-DMSO) : 6 = 1.40-1.60 ppm m ( 4H) ; 2.14-2.28 m (4H); 6.18-6.30 m (1H); 6.50 d (J = 18 Hz, 1H); 7.07 (7.12) each s (broad)(lH); 7.32-7.64 m (11H); 7.70 (7.78) each d (J = 8 Hz, 1H); 12.00 s (wide)(1H). ;Example 141 ;7-(1,2-diphenyl-1H-benzimidazol-6-yl)heptanoic acid methyl ester was obtained by reaction of (E/Z)-7-(1,2-diphenyl-1H-benzimidazol-6-yl) hept-6-enoic acid methyl ester according to the general working instructions 1. ;<1>H-NMR (CDC13) : 6 = 1.30-1.42 ppm m (4H); 1.55-1.70 m (4H); 2.30 h (J = 7.5 Hz, 2H); 2.68 h (J = 7.5 Hz, 2H); 3.56 s (3H); 7.02 s (wide)(lH); 7.18 dd (J = 8.2 Hz, 1H); 7.28-7.35 m (5H); 7.45-7.58m (5H); 7.79 d (J = 8 Hz, 1H) . Example 142 7-(1,2-diphenyl-1H-benzimidazol-6-yl)heptanoic acid was obtained by reacting 7-(1,2-diphenyl-1H-benzimidazol-6-yl)heptanoic acid methyl ester according to the general work instructions 9. ;Smp. 99-103 °C. ;Example 143 ;N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide ;Example 144 ;N-(phenylsulfonyl)-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzene -sulfonamide ;a) 5-amino-1,2-diphenyl-1H-benzimidazole ;2, 4-diaminodiphenylamine is reacted with trimethylorthobenzoate according to the general work instructions 3. ;<1>H-NMR (CDCI3) : 5 = 6 .70 ppm dd (J =7.5, 2 Hz, 1H); 7.06 d (J = 7.5 Hz, 1H); 7.18 d (J = 2 Hz, 1H); 7.28-7.60 m (10H).. ;5-amino-1,2-diphenyl-1H-benzimidazole was reacted with benzenesulfonic acid chloride according to the general working instructions 13. ;143: mp. 196-205 °C. ;144: <1>H-NMR (CDCl 3 ) : δ = 6.94 ppm dd (J = 7.5, 2 Hz, 1H); 7.20 d (J = 2 Hz, 1H); 7.26-8.04m (21H). ;Example 145 ;3-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide ;Example 146 ;N- [(3-chlorophenyl)sulfonyl]-N-(1,2-diphenyl- 1H-benzimidazol-5-yl) - ;(3-chlorobenzene)sulfonamide ;5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 3-chlorobenzenesulfonic acid chloride according to the general working instructions 13. ;145: Mp. 160-162 °C. ;146: <1>H-NMR (CDCl 3 ) : δ = 6.93 ppm dd (J = 7.5, 2 Hz, 1H); 7.25 d (J = 2 Hz, 1H); 7.28-7.57 m (13H); 7.66 d (broad)(2H); 7.90 d (broad)(2H); 8.00 d (broad)(2H). Example 147 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide 5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13. ;<1>H-NMR (CDC13) : 6 = 6.86 ppm s (broad) (1H) ; 7.11 d (J = 7.5, 2 Hz, 1H); 7.17 d (J = 2 Hz, 1H); 7.25-7.55 m (12H); 7.70 d (J = ;10 Hz, 2H). ;Example 148 ;4-bromo-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide ;Example 149 ;N-(4-bromophenylsulfonyl)-N-(1,2-diphenyl-1H-benzimidazol -5-yl)-4-bromobenzenesulfonamide; 5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 4-bromobenzenesulfonic acid chloride according to the general working instructions 13. ;148: mp. 135-139 °C. ;149: <1>H-NMR (CDCl3) : δ = 6.90 ppm dd (J =7.5, 2 Hz, 1H); 7.23 d (J = 2 Hz, 1H); 7.28-7.43 m (11H); 7.72 d (J = 10 Hz, 2H); 7.86 d (J = 10 Hz, 2H). ;Example 150 ;4-(trifluoromethyl)-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide ;Example 151 ;N-(1,2-diphenyl-1H-benzimidazol-5- yl)-N-[(3-trifluoromethyl)phenylsulfonyl]-(3-trifluoromethyl)benzenesulfonamide; 5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 3-trifluoromethylbenzenesulfonic acid chloride according to the general working instructions 13. ;150 : Smp. 116-121 °C. ;151: Smp. 238-241 °C. ;Example 152 ;3- methyl-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide ;Example 153 ;N-(1,2-diphenyl-1H-benzimidazol-5-yl)-N- (3-methylphenylsulfonyl)-3-methylbenzenesulfonamide; 5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 3-methylbenzenesulfonic acid chloride according to the general work instructions 13. ;152: mp. 192-195 °C. ;153: Smp. 173-176 °C. ;Example 154 ;4-methyl-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide ;Example 155 ;N-(1,2-diphenyl-1H-benzimidazol-5-yl)-N- (4-methylphenylsulfonyl)-4-methylbenzenesulfonamide ;5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 4-methylbenzenesulfonic acid chloride according to general working instructions 13. ;154: <1>H-NMR (CDCl3) : δ = 2.38 ppm s (3H); 6.77 s (wide) (1H) ; 7.14-7.55 m (14H); 7.66 d (J = 10 Hz, 2H). ;155: Smp. 234-236 °C. ;Example 156 ;4-Methoxy-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide ;Example 157 ;N-(1,2-diphenyl-1H-benzimidazol-5-yl)-N- (4-Methoxyphenylsulfonyl)-4-methoxybenzenesulfonamide ;5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 4-methoxybenzenesulfonic acid chloride according to the general working instructions 13. ;156: <1>H-NMR (CDC13) : δ = 3.82 ppm s (3H); 6.78 s (broad) (1H, H-4); 6.88 d (J = 7.5 Hz, 1H); 7.14 d (J = 1.5 Hz, 1H); 7.28-7.55 m (12H); 7.72 d (J = 8 Hz, 2H). ;157: <1>H-NMR (CDCl3) : 6 = 3.90 ppm s (6H); 6.93 dd (J = 7.5, 2 Hz, 1H); 7.00 d (J = 10 Hz, 4H); 7.06 d (J = 2 Hz, 1H); 7.30-7.58 m (UH) ; 7.93 d (J = 10 Hz, 4H) . ;Example 158 ;N-(1,2-diphenyl-1H-benzimidazol-5-yl)propanesulfonamide ;Example 159 ;N-(1,2-diphenyl-1H-benzimidazol-5-yl)-N-(propylsulfonyl)- propanesulfonamide ;5-amino-1,2-diphenyl-1H-benzimidazole was reacted with propanebenzenesulfonic acid chloride according to the general working instruction 13. ;158: <1>H-NMR (CDC13/D6-DMS0) : 6 = 0.80 ppm t (J = 7.5 Hz, 3H) ; 1.65m (2H); 2.82m (2H); 6.95 d (J = 7.5 Hz, 1H); 7.08 dd (J = 7.5, 2 Hz, 1H); 7.10-7.40m (10H); 7.61 d (J = 2 Hz, 1H); 9.05 s (broad)(1H, NH). ;159: <1>H-NMR (CDCl 3 ) : δ = 1.08 ppm t (J = 7.5 Hz, 3H); 1.12 h (J = 7.5 Hz, 3H); 2.00m (4H); 3.60m (4H); 7.25-7.63m (13H). ;Example 160 ;N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenemethanesulfonamide ;5-amino-1,2-diphenyl-1H-benzimidazole was reacted with benzenemethanesulfonic acid chloride according to the general working instruction 13. ;Smp . 185-188 °C. ;Example 161 ;6-[[1,2-diphenyl-1H-benzimidazol-5-yl] amino]hexanoic acid methyl ester ;Example 162 ;6-[N-(1,2-diphenyl-1H-benzimidazol-5-yl)- N-[(5-methoxycarbonyl)-pentyl]amino]hexanoic acid methyl ester ; To a solution of 285 mg of 5-amino-1,2-diphenyl-1H-benzimidazole in 5 ml of methanol, 207 mg of 6-bromohexanoic acid methyl ester, 138 mg of potassium carbonate and 150 mg of sodium iodide and allowed to stir for 3 d at 20 °C. Water was added, extracted three times with ethyl acetate, the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. ;161: Smp. 109-113 °C. ;162: <1>H-NMR (CDCl 3 ): δ = 1.30-1.43 m (4H); 1.53-1.73 m (8H); 2.32 h (J = 7.5 Hz, 4H); 3.30 h (J = 7.5 Hz, 4H); 3.68 s (6H); 6.75 dd (J = 10, 2 Hz, 1H); 7.10 d (J = 10 Hz, 1H); 7.14 d (J = 2 Hz, 1H); 7.23-7.35 m (5H); 7.42-7.58m (5H) . Example 163 6-[[1,2-diphenyl-1H-benzimidazol-5-yl]amino]hexanoic acid was obtained by reacting 6-[[1,2-diphenyl-1H-benzimidazol-5-yl]amino] hexanoic acid methyl ester according to the general work instructions 9. ;<X>H-NMR (D6-DMSO) : δ = 1.35-1.50 ppm m (2H) ; 1.50-1.68 m (4H); 2.23 h (J = 7.5 Hz, 2H); 3.05 h (J = 7.5 Hz, 2H); 6.67 dd (J = 10, 2 Hz, 1H); 6.80 d (J = 2 Hz, 1H); 6.92 d (J = 10 Hz, 1H); 7.30-7.40m (4H); 7.45-7.62 m (6H). ;Example 164 ;6-[[2-phenyl-1-[4-(phenylmethoxy)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;a) (5-hydroxy-2-nitrophenyl)[(4 -(phenylmethoxy)phenyl]amine; 1 g of 3-fluoro-4-nitrophenol and 3.8 g of 4-benzyloxyaniline; was stirred for 6.5 h at 150 °C. The charge was then diluted with dichloromethane. After extraction twice with 1 N aqueous hydrochloric acid and washing with water, it was extracted twice with 2 N aqueous sodium hydroxide solution. The basic aqueous phase was treated with ethyl acetate and 1 N aqueous hydrochloric acid. After phase separation, the organic phase was extracted several times with 1 N aqueous hydrochloric acid. After washing the organic phase with saturated sodium chloride solution was dried over sodium sulfate, concentrated in vacuo and the residue chromatographed on silica gel.<1>H-NMR (D6-DMSO): δ = 5.14 ppm s (2H); 6.23 m (2H); 7.10 d (J =. ;8 Hz, 2H); 7.26 d (J = 8 Hz, 2H); 7.32-7.52 m (5H);'8 .03 d (J = 8 Hz, 1H); 9.-52 s (1H) ; 10.71 s (1H). b) 6-[[4-nitro-3-[[4-(phenylmethoxy)phenyl] amino]phen yl]oxy]-hexanoic acid methyl ester was obtained by reacting (5-hydroxy-2-nitrophenyl)[(4-(phenylmethoxy)phenyl]amine with 6-bromohexanoic acid methyl ester in accordance with the general working instructions 8. <1>H-NMR (CDCl 3 ) : 6 = 1.37-1.50 m (2H); 1.59-1.80m (4H); 2.33 h (J = 7.5 Hz, 2H); 3.67 s (3H); 3.83 h (J = 7.5 Hz, 2H); 5.12 s (2H); 6.24-6.33 m (2H); 7.04 d (J = 8 Hz, 2H); 7.21 d (J = 8 Hz, 2H); 7.32-7.50 m (5H); 8.17 d (J = 8 Hz, 1H); 9.66 s (1H). 6-[[2-phenyl-1-[4-(phenylmethoxy)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was obtained by reduction of 6-[[4-nitro-3-[[4-( phenylmethoxy)-phenyl]amino]phenyl]oxy]hexanoic acid methyl ester according to general working instructions 2 and with subsequent cyclization with trimethylorthobenzoate according to general working instructions 3. <1>H-NMR (CDCI3) : 6 = 1.43-1 .58m (2H) ; 1.65-1.86 m (4H); 2.35 h (J = 7.5 Hz, 2H); 3.67 s (3H); 3.94 h (J = 7.5 Hz, 2H); 5.14 s (2H); 6.64 d (J = 2 Hz, 1H); 6.95 dd (J = 8.2 Hz, 1H); 7.11 d (J = 8 Hz, 2H); 7.18-7.61 m (12H); 7.74 d (J = 8 Hz, 1H). Example 165 6-[[2-phenyl-1-[4r(phenylmethoxy)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid 6-[[2-phenyl-1-[4-(phenylmethoxy)phenyl] -1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was reacted according to the general working instruction 9. <1>H-NMR (D6-DMSO): δ = 1.36-1.62 m (4H); 1.65-1.78 m (2H); 2.22 h (J = 7.5 Hz, 2H); 3.92 h (J = 7.5 Hz, 2H); 5.18 s (2H); 6.59 d (J = 2 Hz, 1H); 6.92 dd (J = 8.2 Hz, 1H); 7.20 d (J = 8 Hz, 2H); 7.30-7.54 m (12H); 7.66 d (J = 8 Hz, 1H). Example 166 6-[[1-(4-hydroxyphenyl)-2-phenyl-1H-ben^imidazol-6-yl]oxy]-hexanoic acid 6-[[2-phenyl-1-[4-(phenylmethoxy)phenyl] -1H-benzimidazol-6-yl]oxy]hexanoic acid was reacted according to general working instructions 1. <X>H-NMR (D6-DMSO): δ = 1.37-1.79 m (6H); 2.22 h (J = 7.5 Hz, 2H); 3.92 h (J = 7.5 Hz, 2H); 6.60 d (J = 2 Hz, 1H); 6.91 dd (J = 8.2 Hz, 1H); 6.94 d (J = 8 Hz, 2H); 7.20 d (J = 8 Hz, 2H); 7.36m (3H); 7.52m (2H); 7.63 d (J = 8 Hz, 1H). ;Example 167 ;6-[[2-phenyl-1-[3-(phenylmethoxy)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;a) (5-hydroxy-2-nitrophenyl)[(3 -(phenylmethoxy)phenyl]amine; 1 g of 3-fluoro-4-nitrophenol and 3.81 g of 3-benzyloxyaniline; were stirred for 22 h at 150° C. The mixture was then taken up in a little dichloromethane and chromatographed directly on silica gel. ;<1>H-NMR (CDCl 3 ) : 6 = 5.10 ppm s (2H) ; 5.82 s (br) (1H) ; 6.27 dd (J = 8, 2 Hz, 1H); 6, 48 d (J = 2 Hz, 1H); 6.86 m (3H); 7.28-7.48 m (5H); 8.15 d (J = 8 Hz, 1H); 9.52 s (br ) (1H); 10.71 s (1H). ;b) 6-[[4-nitro-3-[[3-(phenylmethoxy)phenyl]amino]phenyl]oxy]-hexanoic acid methyl ester ;was obtained by reaction of ( 5-hydroxy-2-nitrophenyl)[(3-(phenylmethoxy)phenyl]amine with 6-bromohexanoic acid methyl ester according to general working instructions 8. ;^-NMR (CDCl3) : 5 = 1.40-1.53 m (2H ) ; 1.61-1.82 m (4H); -2.34 h (J = 7.5 Hz, 2H); 3.67 s (3H); 3.88 h (J = 7.5 Hz, 2H); 5.10 s (2H); 6.33 dd (J = 8, 2 Hz, 1H); 6.58 d (J = 2 Hz, 1H); 6.83-6.96 m (3H) ; 7.28-7.49 m (5H); 8, 17 d (J = 8 Hz, 1H); 9.74 s (br) . ;6-[[2-phenyl-1-[3-(phenylmethoxy)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;was obtained by reduction of 6-[[4-nitro-3-[[ 3-(Phenylmethoxy)-phenyl]amino]phenyl]oxy]hexanoic acid methyl ester according to general working instructions 2 and with subsequent cyclization with trimethylorthobenzoate according to general working instructions 3. <1>H-NMR (CDCI3) : 5 = 1 .45-1.60m (2H) ; 1.66-1.88 m (4H); 2.35 h (J = 7.5 Hz, 2H); 3.68 s (3H); 3.93 h (J = 7.5 Hz, 2H); 5.02 s ; (2H); 6.69 d (J = 2 Hz, 1H); 6.90m (2H); 6.97 dd (J = 8.2 Hz, 1H); 7.11 ddd (J = 8, 2, 2 Hz, 1H); 7.28-7.46 m (9H); 7.78 d (J ;= 8 Hz, 1H). ;Example 168 ;6-[[2-phenyl-1-[3-(phenylmethoxy)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid ;6-[[2-phenyl-1-[3-( phenylmethoxy)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was reacted according to the general working instruction 9. ;<1>H-NMR (CDCl3) : δ = 1.49-1.62 m (2H) ; 1.67-1.88 m (4H); 2.39 h (J = 7.5 Hz, 2H); 3.93 h (J = 7.5 Hz, 2H); 5.03 s (2H); 6.68 d (J = 2 Hz, 1H); 6.91m (3H); 6.98 dd (J = 8.2 Hz, 1H); 7.12 ddd (J = 8, 2, 2 Hz, 1H); 7.29-7.47 m (8H); 7.57 d (J = 8 Hz, 2H); 7.81 d (J = 8 Hz, 1H) . ;Example 169 ;6-[[1-(3-hydroxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid ;6-[[2-phenyl-1-[3-(phenylmethoxy)phenyl ]-1H-benzimidazol-6-yl]oxy]hexanoic acid was reacted according to the general working instruction 1. ;<1>H-NMR (D6-DMSO): δ = 1.39-1.80 m (6H); 2.23 h (J = 7.5 Hz, 2H); 3.94 h (J = 7.5 Hz, 2H); 6.57 d (J = 2 Hz, 1H); 6.74 dd (J = 2.2 Hz, 1H); 6.84 dd (J = 8.2 Hz, 1H); 6.94m (2H); 7.38m (4H); 7.53m (2H); 7.66 d (J = 8 Hz, 1H). ;Example 170 ;6-[[1-(3-hydroxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester ;6-[[2-phenyl-1-[3-(phenylmethoxy)phenyl ]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was reacted according to the general working instruction 1. <1>H-NMR (D6-DMSO)-: 6 = 1.38-1.80 m (6H); 2.32 h (J = 7.5 Hz, 2H); 3.59 s (3H); 3.94 h (j'= 7.5Hz, 2H); 6.66 d (J = 2 Hz, 1H); ;6.74 dd (J = 2.2 Hz, 1H); 6.83 dd (J = 8.2 Hz, 1H); 6.93 dd (J = 8, 2 Hz, 2H); 7.38m (4H); 7.54m (2H); 7.67 d (J = 8 Hz, 1H). ;Example 171 ;6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid ethyl ester ;was obtained by reacting 6-hydroxy-1-(3-nitrophenyl) -2-phenylbenzimidazole (DE 4330959) with 6-bromohexanoic acid ethyl ester according to the general work instructions 8. ;Mp. 104-106 °C. ;Example 172 ;6-[[4-bromo-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;a) 4-bromo-6-methoxy-2-phenyl -1H-benzimidazole; 36.6 g of 4-amino-3-bromo-5-nitroanisole (J. Chem. Soc.; 1966, 1769) were previously placed in 750 ml of ethanol and provided with 19.8 g of iron powder and 126 ml of acetic acid. After stirring for 2.5 h at 55 ? C, 350 ml of dichloromethane was added and the mixture made basic with 2 N sodium hydroxide solution. After filtration over Celite, it was washed with water and saturated sodium chloride solution and concentrated. The crude phenylenediamine thus obtained was reacted with trimethylorthobenzoate in accordance with the general work instructions 3. ;Smp. 203-205 °C. ;b) 4-bromo-6-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole 2.5 g 4-bromo-6-methoxy-2-phenyl-1H-benzimidazole and ;2.24 g of 4-(methylbenzene)boric acid was stirred with 1.5 g of anhydrous copper (II) acetate and approx. 3 g molecular sieve in 35 ml pyridine for 7 h at 100 °C. After addition of dichloromethane and Celite, concentration and chromatography on silica gel with a hexane/ethyl acetate mixture was carried out. ; 209-210 °C. ;c) 4-bromo-6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole 1.2 g 4-bromo-6-methoxy-1-(4-methylphenyl)-2-phenyl- 1H-benzimidazole, 6 ml of acetic acid and 6 ml of aqueous hydrobromic acid (62% strength) are boiled for 5.5 hours. The mixture is then precipitated with water, and the precipitate is suctioned off. This was then partitioned between ethyl acetate and 2 N sodium hydroxide solution. After washing the organic phase with water, concentration was carried out. ; 136-137 °C. ;6-[[4-bromo-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;was obtained by reacting 4-bromo-6-hydroxy-1-( 4-methylphenyl)-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to the general work instructions 8. ;Mp. 136 °C. ;Example 173 ;6-[[4-acetyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;0.5 g 4-bromo-6-hydroxy-1 -(4-methylphenyl)-2-phenyl-1H-benzimidazole, 0.37 ml of (α-ethoxyvinyl)tributyltin and 140 mg of dichlorobis(triphenylphosphine)palladium were stirred in 10 ml of toluene for 18 h at 100 °C. After cooling, it was stirred for 0.25 h with 2 N aqueous hydrochloric acid. After phase separation, the organic phase was washed with water and concentrated. The residue was chromatographed on silica gel with a hexane/ethyl acetate mixture. ; 114-115 °C. ;Example 174 ;6~[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexane acid methyl ester ;a) 5-methoxy-1-(4-methylphenyl)-2- phenyl-1H-benzimidazole; 16.8 g of 5-methoxy-2-phenyl-1H-benzimidazole (Bull. Sei.; Fac. Chim. Ind. Bologna, 11, 1953, 42) and 20.4 g of 4-(methyl -benzene)boric acid is reacted according to the general work instructions 14. ;<X>H-NMR (CDC13) : δ = 2.45 s (3H); 3.91 s (3H); 6.90 dd (J = 8, ;2 Hz, 1H); 7.12 d (J = 8 Hz, 1H); 7.18 d (J = 8 Hz, 2H); 7.25-7.38m (6H); 7.57m (2H). In addition, 6-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole was obtained. b) 5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole was obtained from 5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole according to the general work instruction 6 ;Smp. 270 °C. ;6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexane-acid methyl ester ;was obtained from 5-hydroxy-1-(4-methylphenyl)-2-phenyl- 1H-benzimidazole by reaction with 6-bromohexanoic acid methyl ester according to the general working instructions 8. ;<1>H-NMR (CDCCl3): δ = 1.48-1.92 m (6H); 2.38 h (J = 7.5 Hz, 2H); 2.46 s (3H); 3.69 s (3H); 4.06 h (J = 7.5 Hz, 2H); 6.89 dd (J = 8.2 Hz, 1H); 7.11 d (J = 8 Hz, 1H); 7.18 d (J = 8 Hz, 2H); 7.24-7.37 m (6H); 7.57m (2H). ;Example 175 ;6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid ;was obtained from 6-[[1-(4-methylphenyl)-2 -phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester according to general working instructions 9. ;<1>H-NMR (D6-DMSO): 6 = 1.41-1.67 m (4H); 1.70-1.83 m (2H); 2.26 h (J = 7.5 Hz, 2H); 2.43 s (3H); 4.05 h (J = 7.5 Hz, 2H); 6.90 dd (J = 8.2 Hz, 1H); 7.04 d (J = 8 Hz, 1H); 7.23-7.40 m (8H); 7.52m (2H); 11.92 s (br.)( 1H). Example 176 6-[[2-phenyl-1-[4-(thiomethyl)phenyl]-1H-benzimidazol-5-yl]oxy]-hexanoic acid methyl ester a) 6-[[2-phenyl]-1H-benzimidazol- 5-yl]oxy]hexanoic acid methyl ester 4.84 g of 2-phenyl-5-hydroxy-1H-benzimidazole (Izv. Akad.; Nauk. SSSR Ser. Chim. 8, 1990, 1888) was obtained by reaction with 6-bromohexanoic acid methyl ester in according to the general work instruction 8. ;<1>H-NMR (CDCI3) : δ = 1.43-1.58 m (2H); 1.64-1.87 m (4H); 2.37 h (J = 7.5 Hz, 2H); 3.69 s (3H); 3.94 h (J = 7.5 Hz, 2H); 6.87 dd (J = 8, 2 Hz, 1H); 7.02 s (br.); 7.40-7.57 m (4H); 8.05m (2H). 6-[[2-phenyl-1-[4-(thiomethyl)phenyl]-1H-benzimidazol-5-yl]oxy]-hexanoic acid methyl ester; was obtained by reaction of 6-[[2-phenyl]-1H-benzimidazole -5-yl]oxy]hexanoic acid methyl ester with 4-(thiomethylbenzene)boric acid according to the general working instructions 14. ;<X>H-NMR (CDC13) : 6 = 1.48-1.61 m (2H) ; 1.66-1.92 m (4H); 2.36 h (J = 7.5 Hz, 2H); 2.54 s (3H); 3.68 s (3H); 4.05 h (J = 7.5 Hz, 2H); 6.90 dd (J = 8.2 Hz, 1H); 7.11 d (J = 8 Hz, 1H); .7.22 d (J = 8 Hz, 2H); 7.27-7.49 m (6H); 7.57m (2H) . Example 177 6-[[2-phenyl-1-[(4-thiomethyl)phenyl]-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester ;was obtained by reacting 6-[[2-phenyl]-1H -benzimidazol-5-yl]oxy]hexanoic acid methyl ester with 4-(thiomethylbenzene)boric acid according to the general working instructions 14. ;<1>H-NMR (CDCl3) : δ = 1.45-1.57 m (2H) ; 1.62-1.86 m (4H); 2.44 h (J = 7.5 Hz, 2H); 2.56 s (3H.) ; 3.66 s (3H); 3.93 h (J = 7.5 Hz, 2H); 6.66 d (J = 2 Hz, 1H); 6.96 dd (J = 8.2 Hz, 1H); 7.18-7.39 m (7H); 7.54m (2H); 7.73 d (J = 8 Hz, 1H). Example 178 6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester was obtained by reaction of 6-[[2-phenyl]-1H- benzimidazol-5-yl]oxy]hexanoic acid methyl ester with thiophene-3-boric acid according to the general working instructions 14. ;<1>H-NMR (CDCI3) : 6 = 1.48-1.62 m (2H) ; 1.66-1.92 m (4H); 2.47 h (J = 7.5 Hz, 2H); 3.68 s (3H); 4.04 h (J = 7.5 Hz, 2H); 6.93 dd (J = 8.2 Hz, 1H); 6.98 dd (J = 5, 1 Hz, 1H); 7.18 d (J = 8 Hz, 1H); 7.28 dd (J = 3, 1 Hz, 1H); 7.30-7.40m (4H); 7.46 dd (J = 5.3 Hz, 1H); 7.60m (2H) . Example 179 6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was obtained by reacting 6-[[2-phenyl]-1H- benzimidazol-5-yl]oxy]hexanoic acid methyl ester with thiophene-3-boric acid according to the general work instructions 14. ; 1H-NMR (CDCl 3 ): δ = 1.45-1.58 m (2H); 1.64-1.87 m (4H); 2.35 h (J = 7.5 Hz, 2H); 3.67 s (3H); 3.97 h (J = 7.5 Hz, 2H); 6.74 d (J = 2 Hz, 1H); 6.95 dd (J = 8.2 Hz, 1H); 7.01 dd (J = 5, 1 Hz, 1H); 7.29 dd (J = 3, 1 Hz, 1H); 7.30-7.38m (4H); 7.47 dd (J = 5, ;3 Hz, 1H); 7.58m (2H) ; 7.73 d (J = 8 Hz, 1H) . Example 180 4-[3-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-phenoxy]butanoic acid methyl ester a) 6-(3-methoxyphenoxy)-1-(4- methylphenyl)-2-phenyl-1H-benzimidazole was obtained from 6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole and 3-methoxybenzeneboronic acid according to the general working instruction 14. ;M.P. 120-122 °C. b) 3-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol was obtained by reaction of 6-(3-methoxyphenoxy)-1-(4-methylphenyl) - 2-phenyl-1H-benzimidazole according to general working instructions 6 with the addition of 10 mol% hexadecyltri-butylphosphonium bromide. ; 252-253 °C. ;4-[3-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-phenoxy]butanoic acid methyl ester ;was obtained by reacting 3-[ [1-(4-methylphenyl )-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol with 4-bromobutyric acid methyl ester according to the general working instructions 8. ;<1>H-NMR (CDCl3) : 5 = 2.00-2.13 m (2H); 2.43 s (3H); 2.50. t (J = 7.5 Hz, 2H); 3.67 s (3H); 3.93 h (J = 7.5 Hz, 2H); 6.44-6.62 m (3H); 6.95 d (J = 2 Hz, 1H); 7.06 dd (J = 8.2 Hz, 1H); 7.12-7.22 m (3H); 7.25-7.39 m (5H); 7.59m (2H); 7.87 d (J = 8 Hz, 1H) . ;Example 181 ;4-[4-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-phenoxy]butanoic acid methyl ester ;a) 6-(4-methoxyphenoxy)-1- (4-Methylphenyl)-2-phenyl-1H-benzimidazole was obtained from 6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole and 4-methoxybenzeneboronic acid according to general work instruction 14. <1> H-NMR (CDCl 3 ): δ = 2.44 s (3H); 3.79 s (3H); 6.82-6.98 m (5H); 7.01 dd (J = 8.2 Hz, 1H); 7.17 d (J = 8 Hz, 2H); 7.25-7.41 m (5H); 7.57m (2H); 7.82 d (J = 8 Hz, 1H). b) 4-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol was obtained by reacting 6-(3-methoxyphenoxy)-1-(4-methylphenyl) - 2-phenyl-1H-benzimidazole according to general working instructions 6 with the addition of 10 mol% hexadecyltri-butylphosphonium bromide. ;<1>H-NMR (De-DMSO): δ = 2.38 s (3H); 6.61 d (J = 2 Hz, 1H); 6.74 d (J = 8 Hz, 2H); 6.86 d (J = 8 Hz, 2H); 6.91-7.01 m (2H); 7.22-7.41 m (6H); 7.49m (2H); 7.75 d (J = 8 Hz, 1H); 9.32 s (1H). ;4-[4-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-phenoxy]butanoic acid methyl ester ;was obtained by reacting 4-[[1-(4-methylphenyl )-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol with 4-bromobutyric acid methyl ester according to the general working instructions 8r. ;<1>H-NMR (CDCl3) : δ = 2.03-2.16 m (2H) ; 2.42 s (3H); 2.53 h (J = 7.5 Hz, 2H); 3.69 s (3H); 3.97 h (J = 7.5 Hz, 2H); 6.78-6.94 m (5H); 6.99 dd (J = 8.2 Hz, 1H); 7.16 d (J = 8, Hz, 2H).; 7.24-7.38m (5H); 7.57m (2H); 7.79 d (J = 8 Hz, 1H). ;Example 182 ;[4-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]phen-oxy] acetic acid methyl ester ;was obtained by reacting 4-[[l-(4 -methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol with bromoacetic acid methyl ester according to the general working instructions 8. ;<X>H-NMR (CDCl3) : δ = 2.43 s (3H) ; 3.82 s (3H); 4.61 s (2H); 6.78T 6.96m (5H); 7.00 dd (J = 8, 2 Hz, 1H); 7.14 d (J = 8, Hz, 2H); 7.23-7.38 m (5H); 7.56m (2H); 7.80 d (J = 8 Hz, 1H). Example 183 4-[(1,2-diphenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester was obtained by reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 4-bromobutanoic acid methyl ester according to the general working instruction 8. ;M.P. 107-110 °C. ;Example 184 ;6-[[2-phenyl-1-(3-pyridyl)-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester ;was obtained by reaction of 6-[[2-phenyl]-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester with pyridine-3-boronic acid according to the general working instruction 14. ;MS (EI): 415 (molecular ion peak). ;Example 185 ; 6-[[2-phenyl-1-(3-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester; was obtained by reacting 6-[[2-phenyl]-1H-benzimidazol- 5-yl]oxy]hexanoic acid methyl ester with pyridine-3-boronic acid according to the general working instruction 14. ;MS (EI): 415 (molecular ion peak). ;Example 186 ;6-[[2-phenyl-l-(2-pyridyl )-1H-benzimidazol-5-yl]oxy]hexanoic acid was obtained by reacting 6-[[2-phenyl]-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester with 2-fluoropyridine according to l the general work instruction 15. ;MS (EI): 401 (molecular ion peak). Example 187 6-[[2-phenyl-1-(2-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid was obtained by reacting 6-[[2-phenyl]-1H-benzimidazol-5 -yl]oxy]hexanoic acid methyl ester with 2-fluoropyridine according to the general working instruction 15. ;MS (EI): 401 (molecular ion peak). Example 188 6-t[2-phenyl-1-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was obtained by reaction of 6-[[2-phenyl]-1H- benzimidazol-5-yl]oxy]hexanoic acid methyl ester with pyridine-4-boronic acid according to the general working instruction 14. ;MS (EI): 415 (molecular ion peak). ;Example 189 ;6-[[2-(4-fluorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;was obtained by reaction of 6-[[4-amino-3-( phenylamino)phenyl]-oxy]hexanoic acid methyl ester with 4-fluorobenzoyl chloride according to the general working instruction 5. ;MS (EI): 432 (molecular ion peak). Example 190 6-[[2-(4-methoxyphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester was obtained by reaction of 6-[[4-amino-3 -(phenylamino)phenyl]-oxy]hexanoic acid methyl ester with 4-methoxybenzoyl chloride according to the general working instruction 5. ;MS (EI): 444 (molecular ion peak). ;Example 191 ;6-[[2-(3-fluorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;was obtained by reaction of 6-[[4-amino-3-( phenylamino)phenyl]-oxy]hexanoic acid methyl ester with 3-fluorobenzoyl chloride according to general working instructions 5. ;MS (EI): 432 (molecular ion peak). ;Example 192 ;6-[[2-(4-bromophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester ;was obtained by reacting 6-[[4-amino-3-( phenylamino)phenyl]-oxy]hexanoic acid methyl ester with 4-bromobenzoyl chloride according to the general working instruction 5. ;MS (EI): 492/494 (molecular ion peaks). Example 193 6-[[2-[4-(trifluoromethyl)phenyl]-1-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester ;was obtained by reacting 6-[[4-amino-3 -(phenylamino)phenyl]-oxy]hexanoic acid methyl ester with 4-(trifluoromethyl)benzoyl chloride according to general working instructions 5. ;MS (EI): 482 (molecular ion peak). ;Example 194 ;6-[[2-(4-fluorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid ;was obtained by reaction of 6-[[2-(4-fluorophenyl) -1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester according to the general working instruction 9. ;MS (EI): 418 (molecular ion peak). Example 195 6-[[l-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester ;was obtained by reacting 6-[[4-amino-3- (phenylamino)phenyl]-oxy]hexanoic acid methyl ester with benzothiophene-2-carbonic acid chloride according to the general work instructions 5. ;Mp. 129-130 °C. Example 196 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid was prepared according to the general working instruction 9. Smp. 340 °C (decomp.). ;Example 197 ;6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester ;Example 198 ;6-[[6-hydroxy-1- (4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid isopropyl ester; 4,5-dimethoxy-1,2-dinitrobenzene was hydrogenated to the diamino compound according to the general working instructions 1 to the general working instructions 3 was cyclized with trimethylorthobenzoate in 5,6-dimethoxy-2-phenyl-1H-benzimidazole (m.p. 131-133 °C). This benzimidazole derivative was, in accordance with the general working instructions 14, reacted with 4-methylphenylboric acid to 5,6-dimethoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole (m.p. 145-148 °C). After ether cleavage with hydrobromic acid according to the general working instructions 6 to 5,6-dihydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole (<1>H-NMR of the hydrobromide (D6-DMSO): 5 = 2.42 ppm s (3H); 6.68 s (1H); 7.22 s (1H); 7.40-7.62 m (10H)) according to the general work instructions 8 alkylation was carried out with 6-bromohexanoic acid isopropyl ester. 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester was obtained; m.p. 137-139 °C; and 6-[[6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid isopropyl ester; m.p. 177-178 °C. Example 199 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was prepared according to the general work instruction 9. Smp. 245-248 °C. ;Example 200 ;6-[[6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid ;was prepared according to the general work instruction 9. Smp. 182-184 °C. ;Example 201 ;6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester ;6-[[5-hydroxy-1-(4-methylphenyl )-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester was methylated with methyl iodide according to general working instructions 8. ;Mp. 89-91 °C. ;Example 202 ;6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid ;was prepared according to the general working instruction 9. Smp. 184-186 °C. ;Example 203 ;6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester ;Example 204 ;6-[[6-hydroxy-1-( 4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester; was prepared analogously to the isopropyl esters by alkylation of 5,6-dihydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole according to the general working instructions 8 with 6-bromohexanoic acid methyl ester. 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was obtained.<*>H-NMR (CDCl 3 ): δ = 1.45 -1.58 ppm m (2H); 1.65-1.90 m (4H); 2.37 h (J = 7.5 Hz, 2H); 2.48 s (3H); 3.68 s (3H); 3.98 h (J =

7.5 Hz, 2H); 5.68 s (broad) (1H, OH); 6.62 s (1H); 7.18 d (J =

8Hz, 2H); 7.22-7.38 m (5H); 7.40 s (1H); 7.53 dd (J = 8, 1 Hz, 2H)

and 6-[[6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester.

Temp. 141-143 °C.

Example 205

6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester 40 mg 6-[[5-methoxy-1-(4-methylphenyl)- 2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was dissolved in 2 ml of methanol, supplied with 1 drop of concentrated sulfuric acid and the mixture stirred for 2 h. Saturated potassium hydrogen carbonate solution was added, diluted with water, extracted with ethyl acetate, the extracts were dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from diisopropyl ether.

Temp. 81-82 °C.

Example 206

6-[[6-Methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]-oxy]hexanoic acid methyl ester

6-[[6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester was methylated with methyl iodide according to the general work instructions 8.

Temp. 108-110 °C.

Example 207

6-[[6-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid

was produced in accordance with the general work instructions 9. Smp. 182-184 °C.

Example 208

6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

«0 3-[(3,4-dimethylphenyl)amino]-4,6-dinitrophenol

To a suspension of 4 g of 4,6-dinitro-3-fluprphenol (J. Org. Chem. 1991, 5958) in 100 ml of ethanol, 6.6 g of 3,4-dimethylaniline was added and stirred for 7 d at 40 °C . After cooling, suction was carried out and the residue recrystallized from ethanol.

<1>H-NMR (CDCl 3 ): δ = 2.20 ppm s (6H); 6.43 s (1H); 6.90-7.0 m (2H); 7.14 d (J = 8 Hz, 1H); 9.08 s (1H); 9.70 s (wide) (1H); 10.2-10.6 (1H).

b) 6-[[3-[(3,4-dimethylphenyl)amino]-4,6-dinitrophenyl]oxy]hexanoic acid methyl ester 5 g 3-[(3,4-dimethylphenyl)amino]-4,6-dinitrophenol was 0-alkylated with 6-bromohexanoic acid methyl ester at 70 °C analogously to the general work instructions 8.

<1>H-NMR (CDCl 3 ): δ = 1.45-1.88 ppm m (6H); 2.30 s (6H); 2.33 h (J = 7.5 Hz, 2H); 3.68 s (3H); 3.88 h (J = 7.5 Hz, 2H); 6.45 s (1H); 7.00-7.08m (2H); 7.25 d (J = 8 Hz, 1H); 9.03 s (1H); 9.89 s (wide) (1H).

c) 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

2.45 g of 6-[[3-[(3,4-dimethylphenyl)amino]-4,6-dinitro-phenyl]oxy]hexanoic acid methyl ester was hydrogenated in methanol according to the general working instruction 1. 500 mg of the crude product was reacted with benzimidate hydrochloride according to the general working instruction 4. In contrast to the general working instruction 4, the crude product was not washed with aqueous hydrochloric acid after it had been taken up in the solvent.

<1>H-NMR (CDCl 3 ) : δ = 1.48-1.58 ppm m "(2H) ; 1.62-1.78 m (2H) ; 1.78-1.90 m (2H); 2.30 s (3H); 2.38 s (3H); 2.38 h (J = 7.5 Hz, 2H); 3.67 s (3H); 3.93 h (J = 7.5 Hz , 2H); 6.56 s (1H); 6.98-7.08 m (2H); 7.18 s (1H); 7.20-7.32 m (4H); 7.52 dd (J = 8 Hz and 2 Hz, 2H) .

Example 209

6-[[5-t[(4-chlorophenyl)sulfonyl]amino]-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6-[(-5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

Temp. 186-191 °C.

Example 210

6-[(5-amino-2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

was prepared with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

MS (EI): 477 (molecular ion peak).

Example 211

6-[(5-amino-1-(4-methoxyphenyl)-2-(4-methoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

MS (EI): 489 (molecular ion peak).

Example 212

6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6-[(5-amino-2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

Temp. 180-182 °C.

Example 213

6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-(4-methoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6-[(5-amino-1-(4-methoxyphenyl)-2-(4-methoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

Temp. 169-171 °C.

Example 214

4-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]butanoic acid methyl ester

was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

<1>H-NMR (CDCl 3 ): δ = 2.17 ppm tt (J = 8 and 8 Hz, 2H); 2.52 h (J = 8 Hz, 2H); 3.68 s (3H); 3.90 s (3H); 3.98 h (J = 7.5 Hz, 2H); 6.54 s (1H); 7.0 d (J = 12 Hz, 2H); 7.18-7.35 m (6H); 7.50-7.58 m (2H).

Example 215

4-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester

4-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]butanoic acid methyl ester was reacted with chlorobenzenesulfonic acid chloride according to the general work instructions 13.

MS (EI): 605 (molecular ion peak).

Example 216

5-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester

was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

<X>H-NMR (CDCl 3 ): δ = 1.78-1.89 ppm m (4H); 2.32 h (J = 8 Hz, 2H); 3.68 s (3H); 3.88 s (3H); 3.92 h (J = 7.5 Hz, 2H); 6.53 s (1H); 7.0 d (J = 12 Hz, 2H); 7.18-7.36 m (6H); 7.48-7.58m (2H) .

Example 217

5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester

5-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

MS (EI): 619 (molecular ion peak).

Example 218

6-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)-oxy]hexanoic acid methyl ester

was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

Temp. 129-131 °C.

Example 219

6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general working instructions 13. M.p. 168-170 °C.

Example 220

6-[ [5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

was produced in accordance with the general work instructions 9. Smp. 181-182 °C.

Example 221

6-[(5-amino-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl)-oxy]hexanoic acid methyl ester

was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

Temp. 105-107 °C.

Example 222

6"[[5-[t(4-chlorophenyl)sulfonyl]amino]-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6-[(5-amino-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general working instructions 13-.

Temp. 189-191 °C.

Example 223

6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

was produced in accordance with the general work instructions 9. Smp. 102-105 °C.

Example 224

5-[(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester

was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

<1>H-NMR (CDCl3): 6 = 1.82-1.95 ppm m (4H); 2.39 h (J = 8 Hz, 2H); 3.69 s (3H); 3.92-4.00 m (2H); 6.60 s (1H); 7.26-7.34 m (6H); 7.43-7.58m (5H).

Example 225

5-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester . 5-[(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-pentanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

Temp. 157-161 °C,

Example 226

5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid

was produced in accordance with the general work instructions 9. Smp. 236-242 _°C.

Example 227

6- t[5-[[(4-fluorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6- [. (5-Amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was reacted with 4-fluorobenzenesulfonic acid chloride according to the general working instruction 13. MS (EI): 617 (molecular ion peak).

Example 228

6-[[5-[[(4-(trifluoromethylphenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was reacted with 4-(trifluoromethyl)-benzenesulfonic acid chloride according to the general work instructions 13.

MS (EI): 668 (molecular ion peak).

Example 229

6-[[5-[[(4-trifluorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1B-benzimidazol-6-yl]oxy]hexanoic acid

was produced in accordance with the general work instructions 9. Smp. 190-192 °C.

Example 230

6-[[5-[[(4-chlorophenyl)sulfonyl]methylamino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

100 mg of 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was dissolved in 3 ml tetrahydrofuran. To this was added 10 mg of sodium hydride at 0 °C, allowed to stir for 30 min, then 50 ul of methyl iodide was added dropwise and allowed to stir for a further 60 min at 0 °C. Saturated ammonium chloride solution was added, extracted three times with ethyl acetate, washed

organic phases with water, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. Temp. 178-180 °C.

Example 231

[[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]amino]acetic acid methyl ester

100 mg of 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)-benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, treated with 8 mg of sodium hydride and stirred for 30 min at 20 °C. 50 mg of bromoacetic acid methyl ester was added, allowed to stir for 15 h, water was added, extracted three times with ethyl acetate, the extracts were dried over sodium sulfate, concentrated in vacuo and the residue was chromatographed on silica gel.

<1>H-NMR (CDCl3) : δ = 3.70 ppm s (3H); 4.52 s (2H); 7.20 d (J =

8Hz, 1H); 7.26-7.58m (14H); 7.70 d (J = 10 Hz, 2H).

Example 232

[[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]acetic acid

was produced in accordance with the general work instructions 9. Smp. 248 °C.

Example 233

4-[[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]butanoic acid methyl ester

100 mg of 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)-benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, treated with 6 mg of sodium hydride and stirred for 30 min at 20 °C. 56 mg of 4-bromobutyric methyl ester was added, allowed to stir for 15 h, water was added, extracted three times with ethyl acetate, the extracts were dried over sodium sulfate, concentrated in vacuo and the residue leached with diisopropyl ether.

Temp. 54-58 °C.

Example 234

4-[[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]butanoic acid

was produced in accordance with the general work instructions 9.

Temp. 24 9-254 °C.

Example 235

5-[[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]pentanoic acid methyl ester

100 mg of 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)-benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, treated with 8 mg of sodium hydride and stirred for 30 min at 20 °C. 60 mg of 5-bromopentanoic acid methyl ester was added, allowed to stir for 15 h, water was added, extracted three times with ethyl acetate, the extracts were dried over sodium sulfate, concentrated in vacuo and the residue chromatographed on silica gel.

3-NMR (CDCl 3 ): δ = 1.46-1.54 ppm m (2H); 1.62-1.78 m (2H); 2.30 h (J = 8 Hz, 2H); 3.62 s (3H); 3.62 h (J = 8 Hz, 2H); 7.12-7.53m (17H) .

Example 236

5- [[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-y1]amino]pentanoic acid

was produced in accordance with the general work instructions 9. Smp. 123-127 °C.

Example 237

6- 11(4-Chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]hexanoic acid methyl ester

6-[[1,2-diphenyl-1H-benzimidazol-5-yl]amino]hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

MS (EI): 588 (molecular ion peak).

Example 238

7- [[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]heptanoic acid methyl ester

100 mg of 4-chloro-N-(1,2-diphenyl-1H-benzimidazol-5-yl)-benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, treated with 8 mg of sodium hydride and stirred for 30 min at 20 °C. 70 mg of 7-bromoheptanoic acid methyl ester was added, allowed to stir for 15 h, supplied with water, extracted three times with ethyl acetate, dried

the extracts over sodium sulfate, concentrated in vacuo and chromatographed the residue on silica gel.

<1>H-NMR (CDCl3) : δ = 1.26-1.64 ppm m (8H); 2.27 h (J = 8 Hz, 2H); 3.60 h (J = 8 Hz, 2H); 3.68 s (3H); 7.12 dd (J = 10, 2 Hz, 1H); 7.22 d (J = 10 Hz, 1H); 7.30-7.61m (15H).

Example 239

7-[[(4-chlorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]heptanoic acid

was produced in accordance with the general work instructions 9. Smp. 172-178 °C.

Example 240

N-(1,2-diphenyl-1H-benzimidazol-5-yl)-4-fluorobenzenesulfonamide

5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 4-fluorobenzenesulfonic acid chloride according to the general work instructions 13.

Temp. 209-214 °C.

Example 241

6-[[(4-fluorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]hexanoic acid methyl ester

150 mg of N-(1,2-diphenyl-1H-benzimidazol-5-yl)-4-fluoro-benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, treated with 12 mg of sodium hydride and stirred for 30 min at 20 °C. 98 mg of 6-bromohexanoic acid methyl ester was added, allowed to stir for 15 h, supplied with water, extracted three times with ethyl acetate, the extracts were dried over sodium sulfate, concentrated in vacuo and the residue was chromatographed on silica gel.

Temp. 128-134 °C.

Example 242

6-[[(4-fluorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]-amino]hexanoic acid

was produced in accordance with the general work instructions. 9. Smp. 200-210 °C.

Example 243

6-[[[4-(trifluoromethyl)phenyl]sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]amino]hexanoic acid methyl ester

150 mg of 4-(trifluoromethyl)-N-(1,2-diphenyl-1H-benzimidazol-5-yl)benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, was treated with 11 mg of sodium hydride and stirred in 30 min at 20 °C. 88 mg of 6-bromohexanoic acid methyl ester was added, allowed to stir for 15 h, supplied with water, extracted three times with ethyl acetate, the extracts dried over sodium sulfate, concentrated in vacuo and the residue leached with diisopropyl ether.

Temp. 159-161 °C.

Example 244

6-[[[4-(trifluoromethyl)phenyl]sulfonyl][1,2-phenyl-1H-benzimidazol-5-yl]amino]hexanoic acid

was produced in accordance with the general work instructions 9. Smp. 224-230 °C.

Example 245

4-chloro-N-[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-5-yl]-benzenesulfonamide

a) (2,4-dinitrophenyl)(4-methoxyphenyl)amine

1.43 g of 4-(2,4-dinitroanilino)phenol, 500 mg of potassium carbonate and 0.32 ml of methyl iodide were stirred for 2 d at 20 °C in 5 ml of N,N-dimethylformamide. The mixture was poured onto water, extracted three times with ethyl acetate, the extracts were dried over sodium sulphate, concentrated in vacuo and the residue chromatographed on silica gel.

Temp. 117-127 °C.

b) 5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazole (2,4-dinitrophenyl)-4-methoxyphenylamine was hydrogenated in

according to the general work instruction 1. The crude product was cyclized with trimethylorthobenzoate to the benzimidazole derivative according to the general work instruction 3.

<X>H-NMR (CDCl 3 ): δ = 3.88 ppm s (3H); 6.70 dd (J = 12, 2 Hz, 1H); 6.95-7.06 m (4H); 7.18-7.38m (7H); 7.53-7.65 m (2H).

c) 4-chloro-N-[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-5-yl]-benzenesulfonamide

5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazole was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

Temp. 238-24 °C.

Example 246

6-[[(4-chlorophenyl)sulfonyl][1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-5-yl]amino]hexanoic acid methyl ester 75 mg 4-chloro-N-[1-(4-methoxyphenyl) )-2-phenyl-1H-benzimidazol-5-yl]benzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, treated with 6 mg of sodium hydride and stirred for 30 min at 20°C. 44 mg of 6-bromohexanoic acid methyl ester was added, allowed to stir for 15 h, supplied with water, extracted three times with ethyl acetate, the extracts were dried over sodium sulfate, concentrated in vacuo and the residue chromatographed on silica gel.

MS (EI): 617 (molecular ion peak).

Example 247

6-[[(4-chlorophenyl)sulfonyl][1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-5-yl]amino]hexanoic acid

was produced in accordance with the general work instructions 9. Smp. 205-208 °C.

Example 248

2,2-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

a) 2,2-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-nitrile

was obtained by reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 6-bromo-1,1-dimethylhexanenitrile according to the general work instructions 8.

Temp. 115-118 °C.

b) 2,2-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide

500 mg of 2,2-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanenitrile was heated for 2 h in 5 ml of 80% sulfuric acid until reflux. After cooling, the solution was

visible all the way over. on ice water, pH adjusted to pH 8 with sodium hydroxide solution, extracted three times with ethyl acetate, the extracts dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel.

Temp. 115-118°C.

Example 249

8-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]octanoic acid methyl ester was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 8-bromooctanoic acid methyl ester according to the general working instructions 8 .

Temp. 92-95 °C.

Example 250

8-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]octanoic acid was prepared according to general work instructions 9. M.p. 136-140 °C.

Example 251

6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

was prepared analogously with 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Temp. 81-85 °C.

Example 252

6- t[I-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid was prepared according to the general working instruction 9. M.p. 17 6-180 °C.

Example 253

7- t[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]heptanoic acid methyl ester

was prepared analogously with 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Temp. 92-98 °C.

Example 254

7-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]heptanoic acid was prepared according to the general work instructions 9.

Temp. 175-178 °C.

Example 255

6-[ [1-(3-fluorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

was prepared analogously with 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Temp. 104-106 °C.

Example 256

6-[[1-(3-fluorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

was produced in accordance with the general work instructions 9.

Temp. 149-151 °C.

Example 257

6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 6-Methoxy-2-(4-nitrophenyl)-1-phenyl-1H-benzimidazole

200 mg of 4-methoxy-N<2->phenyl-o-phenylenediamine was dissolved in 5 ml of N,N-dimethylformamide, supplied with 34 6 mg of EEDQ and 234 mg of 4-nitrobenzoic acid and the mixture stirred for 5 h at 100 °C. After cooling, water was added. The precipitate was sucked off and purified using column chromatography, taken up in 6 N hydrochloric acid and heated for 2 h under reflux. After cooling, the solution was dropped into potassium bicarbonate solution. The precipitate was sucked off and dried.

Temp. 189-191 °C. b) 6-hydroxy-2-(4-nitrophenyl)-1-phenyl-1H-benzimidazole was obtained by conversion according to the general work instructions 6.

<1>H-NMR (D6-DMSO): δ = 6.56 ppm d (J = 2 Hz, 1H); 6.87 dd (J = 10, 2 Hz, 1H); 7.46 dd (J = 10, 2 Hz, 2H); 7.53-7.70 m (4H); 7.75 d (J = 10 Hz, 2H); 8.20 d (J = 10 Hz, 2H); 9.55s (wide)(1H).

c) 6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by turnover in accordance with the general work instructions 8.

<1>H-NMR (CDCl 3 ): δ = 1.45-1.55 ppm m (2H); 1.62-1.84 m (4H); 2.33 h (J = 8 Hz, 2H); 3.68 s (3H); 3.95 h (J = 8 Hz, 2H); 6.67 d (J = 2 Hz, 1H); 7.00 dd (J = 10, 2 Hz, 1H); 7.28-7.38 m (2H); 7.52-7.60 m (3H); 7.71 d (J = 10 Hz, 2H); 7.77 d (J = 10 Hz, 1H); 8.13 d (J = 10 Hz, 2H).

Example 258

6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

was produced in accordance with the general work instructions 9. Smp. 181-186 °C.

Example 259

6-[[1-phenyl-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

was prepared analogously with 6-[[l-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Temp. 159-160 °C.

Example 260

N-(cyclopropylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)-oxy]hexanamide

was produced in accordance with the general work instructions 18.

MS (EI): 469 (molecular ion peak).

Example 261

N-isobutoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide

was produced in accordance with the general work instructions 18.

MS (EI): 471 (molecular ion peak).

Example 262

N-(phenylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide

To a solution of 17 mg of carbonyldiimidazole in 1 ml of tetrahydrofuran was added a solution of 50 mg of 6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanoic acid in 1 ml of tetrahydrofuran, stirred for 30 minutes at 20 °C and heated for 30 minutes until reflux. At 20 °C, 16 mg of O-benzylhydroxylamine hydrochloride was added and allowed to stir for 20 h. For work-up, ethyl acetate was added, extracted with 2 N hydrochloric acid and saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated in vacuo. The residue was purified by means of column chromatography on silica gel.

Temp. 145-148 °C.

Example 263

N-(cyclopropylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide

was prepared, analogously to N-(phenylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide.

MS (EI): 559 (molecular ion peak).

Example 264

N-isobutoxy-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide

was prepared analogously with N-(phenylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide.

<1>H-NMR (CDCl 3 ): δ = 0.94 ppm d (J = 8 Hz, 6H); 1.48-2.03 m (7H); 2.05-2.18 m (2H); 3.60-3.72 m (2H); 3.76 s (6H); 3.90-4.00 m (2H); 3.96 s (3H); 6.50 s (2H); 6.72 d (J = 2 Hz, 1H); 6.95 dd (J = 10, 2 Hz, 1H); 7.28-7.38 m (3H); 7.55-7.62 m (2H); 7.74 d (J = 10 Hz, 1H); 8.20 s (wide)(1H).

Example 265

N-isopropyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide was prepared according to the general working instruction 17. M.p. 107-112 °C.

Example 266

N,N-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide was prepared according to the general working instruction 17. M.p. 83-88 °C.

Example 267

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-pyrrolidin-1-ylhexan-1-one

was produced in accordance with the general work instructions 17. Smp. 84-88 °C.

Example 268

N-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

was produced in accordance with the general work instructions 17. Smp. 63-68 °C.

Example 269

N-(3-methoxypropyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

was prepared in accordance with the general work instructions 18. Smp. 84-91 °C.

Example 270

N-isobutyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide was prepared according to the general working instruction 17. <X>H-NMR (CDC13) : δ = 0.90 ppm d (J = 8 Hz, 6H) ; 1.44-1.57 m (2H); 1.65-1.85 m (5H); 2.20 h (J = 8 Hz, 2H); 3.08 h (J = 8 Hz, 2H); 3.94 h (J = 8 Hz, 2H); 6.68 d (J = 2 Hz, 1H); 6.96 dd (J = 10, 2 Hz, 1H); 7.25-7.38m (5H); 7.45-7.58m (5H); 7.75 d (J =

10 Hz, 1H).

Example 271

N-[(2,2-dimethylamino)ethyl]-N-methyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

was prepared according to the general working instructions 17. <1>H-NMR (CDCl3) (signals from the main rotamer): δ = 1.44-1.57 ppm m (2H); 1.64-1.84 m (4H); 2.30 s (6H); 2.34 h (J = 8 Hz, 2H);

2.47 h (J = 8 Hz, 2H); 3.00 s (3H); 3.50 h (J = 8 Hz, 2H); 3.94

t (J = 8 Hz, 2H); 6.69 d (J = 2 Hz, 1H); 6.96 dd (J = 10, 2 Hz, 1H); 7.25-7.36 m (5H); 7.45-7.56 m (5H); 7.73 d (J = 10 Hz, 1H).

Example 272

N-(2-methoxyethyl)-N-methyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

was prepared according to the general working instructions 17. <1>H-NMR (CDC13) (signals from the main rotamer): δ = 1.43-1.58 ppm m (2H); 1.63-1.84 m (4H); 2.33 h (J = 8 Hz, 2H); 3.07 s (3H); 3.32 s (3H); 3.47-3.58 m (4H) ; 3.95 h (J = 8 Hz, 2H); 6.70 d (J = 2 Hz, 1H); 6.96 dd (J = 10, 2 Hz, 1H); 7.25-7.35 m (5H); 7.45-7.55 m (5H); 7.75 d (J = 10 Hz, 1H).

Example 273

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-morpholin-1-yl-hexan-1-one

was prepared according to the general work instructions 17. <1>H-NMR (CDCI3): 6 = 1.47-1.59 ppm m (2H); 1.63-1.88 m (4H);

2.34 h (J = 8 Hz, 2H); 3.42-3.49 m (2H); 3.57-3.70 m (6H); 3.94 h (J = 8 Hz, 2H); 6.68 d (J = 2 Hz, 1H); 6.96 dd (J = 10, 2 Hz, 1H); 7.23-7.38 m (5H); 7.45-7.56 m (5H); 7.75 d (J = 10 Hz, 1H).

Example 274

N,N-di-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)-oxy]hexanamide

was prepared in accordance with the general work instructions 18. Smp. 88-98 °C.

Example 275

N-isopentyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide was prepared according to the general working instruction 18. M.p. 127-129 °C.

Example 276

N-(pyridin-2-yl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

was prepared according to the general work instructions 18. Mp, 120-124 °C. '

Example 277

N-(pyridin-3-yl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

was prepared in accordance with the general work instructions 18. Smp. 154 °C.

Example 278

6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-piperidin-1-ylhexan-1-one

was prepared in accordance with the general work instructions 18. Smp. 93-98. °C.

Example 279

[6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-hexanoyl]piperidine-4-carbonamide

was produced in accordance with the general work instructions 17. Smp. 177-178 °C.

Example 280

[[6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-hexanoyl]methyl-amino] acetic acid ethyl ester

was prepared according to the general working instruction 17. <X>H-NMR (CDCl 3 ) (signals from the main rotamer): δ = 1.23 ppm t (J = 8 Hz, 3H); 1.45-1.88 m (6H); 2.40 h (J = 8 Hz, 2H); 3.08 s (3H); 3.93 h (J = 8 Hz, 2H); 4.12 s (2H); 4.18 q (J = 8 Hz, 2H); 6.70 d (J = 2 Hz, 1H); 6.97 dd (J = 10, 2 Hz, 1H); 7.23-7.35 m (5H); 7.45-7.58m (5H); 7.75 d (J = 10 Hz, 1H).

Example 281

4-[[6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-hexanoyl]]-piperazine-1-carboxylic acid ethyl ester

was prepared according to the general working instructions 17. <X>H-NMR (CDCl3) : δ = 1.27 ppm t (J = 8 Hz, 3H); 1.45-1.60m (2H); 1.63-1.88 m (4H); 2.36 h (J = 8 Hz, 2H); 3.40-3.53 m (6H); 3.56-3.64 m (2H) ; 3.93 h (J = 8 Hz, 2H); 4.15 q (J = 8 Hz, 2H); 6.6.9 d (J = 2 Hz, 1H); 6.96 dd (J = 10, 2 Hz, 1H); 7.23-7.38 m (5H); 7.45-7.56 m (5H) ;' 7.76 d (J = 10 Hz, 1H) .

Example 282

N-isopropyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was produced in accordance with the general work instructions 18.

MS (EI): 4 69 (molecular ion peak).

Example 283

N,N-dimethyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was produced in accordance with the general work instructions 18.

MS (EI): 455 (molecular ion peak).

Example 284

N,N-diethyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was produced in accordance with the general work instructions 18.

MS (EI): 483 (molecular ion peak).

Example 285

N-isobutyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was prepared according to the general working instructions 18. <1>H-NMR (CDC13): δ = 0.90 ppm d (J = 8 Hz, 6H); 1.44-1.55 m (2H); 1.58-1.83 m (5H); 2.20 h (J = 8 Hz, 2H); 2.30 s (3H); 2.35 s (3H); 3.09 h (J = 8 Hz, 2H); 3.94 h (J = 8 Hz, 2H); 6.63 d (J = 2 Hz, 1H); 6.94 dd (J = 10, 2 Hz, 1H); 7.02 dd (J = 10, 2 Hz, 1H); 7.10 d (J = 2 Hz, 1H); 7.22-7.35 m (4H); 7.56 dd (J = 8 Hz and 2 Hz, 2H); 7.73 d (J = 10 Hz, 1H).

Example 286

N-cyclopropyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was produced in accordance with the general work instructions 18.

MS (EI): 467 (molecular ion peak).

Example 287

N-cyclobutyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was produced in accordance with dé-n' general work instructions 18.

1H-NMR (CDCl 3 ): δ = 1.42-1.55 ppm m (2H); 1.60-1.88 m (8H); 2.15 h (J = 8 Hz, 2H); 2.28-2.40 m (2H); 2.30 s (3H); 2.35 s (3H); 3.93 h (J = 8 Hz, 2H); 4.40 quintet (J = 8 Hz, 2H); 5.55 s (wide) (1H); 6.63 d (J = 2 Hz, 1H); 6.92 dd (J = 10, 2 Hz, 1H); 7.03 dd (J = 10 Hz and 2 Hz, 1H); 7.08 d (J = 2 Hz, 1H); 7.20-7.36 m (4H); 7.57 dd (J = 8, 2 Hz, 2H); 7.72 d (J = 10 Hz, 1H) .

Example 288

N-tert-butyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was prepared according to the general working instructions 18. <1>H-NMR (CDCl3): 6 = 1.32 ppm s (9H); 1.42-1.55 m (2H); 1.62-1.82 m (4H); 2.10 h (J = 8 Hz, 2H); 2.30 s (3H); 2.36 s (3H); 3.92 t.

(J = 8 Hz, 2H); 5.23 s (broad) (1H); 6.66 d (J = 2 Hz, 1H); 6.93 dd (J = 10, 2 Hz, 1H); 7.02 dd (J = 10 Hz and 2 Hz, 1H); 7.09 s (wide)(lH); 7.22-7.36 m (4H); 7.56 dd (J = 8, 2 Hz, 2H); 7.73 d (J = 10 Hz, 1H).

Example 289

(R)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-1-(2-methoxymethyl)pyrrolidin-1-ylhexan-1-one

was produced in accordance with the general work instructions 18.

MS (EI): 467 (molecular ion peak).

Example 290

N-(3-imidazol-1-yl-propyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was prepared according to the general work instructions 18. <1>H-NMR (CDCl3): δ = 1.42-1.53 ppm m (2H); 1.62-2.02 m (6H); 2.17 h (J = 8 Hz, 2H); 2.27 s (3H); 2.34 s (3H); 3.24 q (J = 8 Hz, 2H); 3.92 h (J = 8 Hz, 2H); 3.96 h (J = 8 Hz, 2H); 5.68 s (wide)(lH); 6.63 d (J = 2 Hz, 1H); 6.88-6.95 m (2H); 7.00 dd (J = 10 Hz and 2 Hz, 1H); 7.04-7.10 m (2H); 7.20-7.36 m (4H); 7.50s (wide)(lH); 7.53 dd (J = 8, 2 Hz, 2H); 7.72 d (J = 10 Hz, 1H).

Example 291

N-(2-pyridin-2-ylethyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

became. produced in accordance with the general work instructions 18. •

<X>H-NMR (CDCl 3 ): δ = 1.38-1.52 ppm m (2H); 1.62-1.82 m (4H); 2.15 h (J = 8 Hz, 2H); 2.30 s (3H); 2.35 s (3H); 2.96 h (J = 8 Hz, 2H); 3.66 q (J = 8 Hz, 2H); 3.90 h (J = 8 Hz, 2H); 6.48 s (wide)(1H); 6.65 d (J = 2 Hz, 1H); 6.92 dd (J = 10, 2 Hz, 1H); 7.00 dd (J = 10 Hz and 2 Hz, 1H); 7.06-7.38 m (7H); 7.53-7.62 m (3H); 7.72 d (J = 10 Hz, 1H); 8.50 d (broad)(J = 6 Hz, 1H).

Example 292

N,N-dimethyl-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was prepared according to the general work instructions 18. <1>H-NMR (CDCI3): 6 = 1.46-1.58 ppm m (2H); 1.64-1.88 m (4H); 2.32 h (J = 8 Hz, 2H); 2.93 s (3H); 3.00 s (3H); 3.96 h (J = 8 Hz, 2H); 6.65 d (J = 2 Hz, 1H); 7.00 dd (J = 10, 2 Hz, 1H); 7.28-7.36 m (2H); 7.53-7.61 m (3H); 7.70 d (J = 10 Hz, 2H); 7.76 d (J = 8 Hz, 1H); 8.13 d (J = 8 Hz, 2.H) .

Example 293

N-isopropyl-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was prepared in accordance with the general work instructions 18. Smp. 162-165 °C.

Example 294

N-isopentyl-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was prepared in accordance with the general work instructions 18. Smp. 148-154 °C.

Example 295

N-(3-methoxypropyl)-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was prepared in accordance with the general work instructions 18. Smp. 104-110 °C.

Example 296

N-(3-methoxypropyl)-6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

was produced in accordance with the general work instructions.18.

3-NMR (CDCl 3 ): δ = 1.43-1.56 ppm m (2H); 1.62-1.85 m (6H); 2.10-2.23 m (4H); 2.95 h (J = 10 Hz, 2H); 3.00 h (J = 10 Hz, 2H) ; 3.32 s (3H); 3.32-3.40 m (2H); 3.48 h (J = 8 Hz, 2H); 3.93 h (J = 8 Hz, 2H); 6.03 s (wide)(lH); 6.67 d (J = 2 Hz, 1H); 6.93 dd (J = 10, 2 Hz, 1H); 7.03 dd (J = 10, 2 Hz, 1H); 7.12 s (wide)(1H); 7.26-7.35 m (4H); 7.55 dd (J = 10 Hz, 2H); 7.72 d (J = 8 Hz, 1H).

Example 297

6-[[1-(4-methylphenyl)-2-(3-pyridyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reacting 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 3-pyridylcarbaldehyde according to the general work instructions 16.

MS (EI): 429 (molecular ion peak).

Example 298

6-[[1-(4-methylphenyl)-2-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid ethyl ester

was obtained by reacting 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 4-pyridylcarbaldehyde according to the general work instructions 16.

MS (EI): 429 (molecular ion peak).

Example 299

6-[[1-(4-methylphenyl)-2-(2-thienyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reaction of 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 2-thienylcarbaldehyde according to the general work instructions 16.

MS (EI): 434 (molecular ion peak).

Example 300

6-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reaction of 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 3-thienylcarbaldehyde according to the general work instructions 16.

MS (EI): 434 (molecular ion peak).

Example 301

6-[[2-(3-indolyl)-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reacting 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 3-indolylcarbaldehyde according to the general work instructions 16.

MS (EI): 4 67 (molecular ion peak).

Example 302

6-[[1-(4-methylphenyl)-2-(2-furyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reacting 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 2-furylcarbaldehyde according to the general work instructions 16.

MS (EI): 418 (molecular ion peak).

Example 303

6-[[1-(4-methylphenyl)-2-(3-furyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

was obtained by reacting 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 3-furylcarbaldehyde according to the general work instructions 16.

MS (EI): 418 (molecular ion peak).

Example 304

6-[[1-(4-methylphenyl)-2-(5-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

was obtained by reacting 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 5-methyl-2-thienylcarbaldehyde according to the general work instructions 16.

MS (EI): 448 (molecular ion peak).

Example 305

6-[[1-(4-methylphenyl)-2-(4-bromo-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

was obtained by reacting 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 4-bromo-2-thienylcarbaldehyde according to the general work instructions 16.

MS' (ÉI):•512/514 (molecular peaks).

Example 306

6-[[1-(4-methylphenyl)-2-(3-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

was obtained by reaction of 6-[[4-amino-3-((4-methylphenyl)-amino)phenyl]oxy]hexanoic acid methyl ester with 3-methyl-2-thienylcarbaldehyde according to the general work instructions 16.

MS (EI): 448 (molecular ion peak).

Example 307

Inhibition of microglial activation

For the in vitro production of A(5-activated microglia, primary rat microglia are incubated with synthetic A(3-peptid: To simulate A(J deposits), synthetic A(3-peptide is dried onto 96-well tissue culture plates. For this, a peptide stock solution of 2 mg/ml H 2 O 1:50 diluted in H 2 O. For coating the 96-well plates, 30 µl of this diluted peptide solution is used per well and dried overnight at room temperature.

Primary rat microglia are harvested from mixed glial cultures that were recovered from P3 rat brains. For the preparation of mixed glial cultures, the brains of 3-day-old rats are removed and freed of brain skin. Single cells were obtained by trypsinization (0.25% trypsin solution, 15 min 37 °C). After separation of undigested tissue fragments using a 40 µm nylon mesh, the isolated cells are centrifuged (800 rpm/10 minutes). The cell pellet was resuspended in culture medium and transferred to 100 ml tissue culture flasks.

(1 brain/tissue culture bottle). The cultivation of the cells took place over a period of 5-7 days in Dulbecco's modified Eagle's medium (DMEM, with glutamine), supplemented with penicillin (50 U/ml), streptomycin (40 µg/ml), and 10% (v/v ) fetal calf serum (FCS) at 37 °C and 5% CO2. During this incubation, an adhesive cell lawn is formed which mainly consists of astrocytes. Microglia propagate as non- or weakly-adhesive cells on this and are harvested via shaking incubation (420 revolutions/minute,

1 hour).

For activation of the microglia by means of A(5-peptide, 2.5 times 104 microglia/well are seeded on Aβ-coated tissue culture plates and over a period of 7 days incubated in DMEM (with glutamine), supplemented with penicillin (50 U /ml), streptomycin (40 µg/ml) and 10% (v/v) fetal calf serum (FCS) at 37 °C and 5% CO 2 . On day 5, administration of a compound according to the invention in different concentrations (0.1 , 0.3, 1.3 and 10 uM) place.

For quantification of microglial reactivity, on culture day 7 the metabolic activity is measured via the reduction of MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(sulfophenyl)-2H-tetrazolium), Owen's Reagent, Baltrop, J.A. et al., Bioorg. & Med. Chem. Easy. 1, 6111 (1991)). The percent inhibition relates to only one control treated with DMSO. The compounds according to the invention inhibit microglial activation.

Example 308

Cerebral infarction in rats (MCAO model)

The compounds according to the invention were tested in an animal experiment for cerebral ischemia (stroke), the MCAO model ("permanent middle cerebral artery occlusion"), for in vivo activity. ■ When the middle cerebral artery (MCA) is unilaterally closed, a cerebral infarction is triggered, which is due to undersupply of the corresponding brain area with oxygen and nutrients. The consequences of this undersupply are a pronounced cell death as well as, subsequently, a strong microglial activation. However, this microglial activation only reaches its maximum after several days and can last for several weeks. For testing the substances, the compounds according to the invention were administered intraperitoneally 1-6 days after occlusion. The animals were perfused on day 7 and sacrificed. The extent of microglial activation was measured using a modified immunohistochemical method. For this, vibratome sections of fixed brains were incubated with antibodies that recognize the CR3 complement receptor or The MHCII complex on activated microglia. The quantification of the primary antibody binding took place using an enzyme-linked detection system. The treatment with the compounds according to the invention led to a significant reduction of microglial activation in the cerebral hemisphere that was exposed to cerebral infarction. The reduction amounted to at least 20%.

Example 309

Activation of macrophages

To test the substances on macrophages/monocytes, LPS-activated THP-1 cells were used. For this, 2.5 x 10 6 cells/ml were seeded in RPMI medium (RPMI 1640 + 10% FCS). The compounds according to the invention were added at a concentration of 5 µM and pre-incubated for 30 minutes. Stimulation of the cells took place overnight at 37°C with 1 µg/ml LPS. The medium was then harvested and the amount of TNFα determined quantitatively. The treatment of the cells with the substances according to the invention led to a reduction of the amount of TNFα of at least 30%.

Claims (6)

1. Benzimidazoles, characterized by general formula: in which R<1> means a phenyl, naphthyl, fluorenyl, indanyl, pyridyl, thienyl, furyl, indolyl or benzothienyl group which may be substituted with up to three of the following substituents independently of each other: F, Cl, Br, I, XOH, XOR4, XCN, XSR4, N02, XNH2, XNHR<4>, XNR<4>R4', R<4>, whereby two substituents on R<1>, if they are in ortho to each other, can be connected to each other in such a way that together they form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R2 has the same meaning as R<1>, R3 means one or two substituents which can independently be: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, NO2, XNH2, XNHR4, XNR<4>R<4>', XNHS02R<4> or R<4>, R4 and R<4>' independently mean C1-4-perfluoro-alkyl,' C1-6-alkyl, phenyl or phenyl-C1-C4-alkyl, whereby the phenyl groups can be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3 or C2F5, R5 and R<5>' independently mean C1-6-alkyl, whereby a carbon atom can be exchanged for Q, S, SO, SO2, NH, NCi-3--alkyl or • NCi-3-alkanoyl, C3-7- cycloalkyl-Co-3Talkyl, whereby in a 5-membered cycloalkyl ring one ring member can be an N or an 0 and in a 6- or 7-membered cycloalkyl ring one or two ring members can be N and/or 0, whereby ring nitrogens can optionally be substituted with C1-3-alkyl or C1-3-alkanoyl, phenyl, phenyl-C1-C4-alkyl, pyridyl, pyridyl-C1-C4-alkyl or imidazolyl-C1-C4-alkyl, whereby all previously mentioned alkyl residues can be substituted with up to two substituents of 0H, 0Ci_3-alkyl, NH2, NHCi-3-alkyl, NHCi-3-alkanoyl, N (Ci-3-alkyl) 2, N (Ci-3-alkyl ) (C1-3-alkanoyl), COOH, C0NH2, C00Ci_3-alkyl and all previously mentioned phenyl and pyridyl groups can be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2H5, N02, OCH3, 0C2H5, CF3, C2F5, or R<5> and R<5>' together with the nitrogen atom form a 7-pyrrolidine, morpholine, piperidine or piperazine ring and may be substituted with C1-4-alkyl, C1-4-alkyl-Co-2-alkyl , C 1-4 -Alkoxycarbonyl or aminocarbonyl, A means C1-10-alkanediyl or C2-10-alkenediyl, B stands for COOH, COOR<5>, C0NH2, C0NHNH2, CONHR<5>, CONR<5>R<5>', CONHOH, CONHOR<5>, S02NH2, S02NHR<5>, S02NR<5>R<5> ', X means a bond, Y means 0, NH, NR<4>, NS02R<4>, whereby the following compounds are excluded: [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid methyl ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester, 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5- [[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy].hexane-acid methyl ester, 5-[[1-(4-aminophenyl)-2-phenyl-1H-benzimidazol -6-yl]oxy]pentanoic acid methyl ester, 5- [ [1-[4-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[4-[( acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[3-[[(4-chlorophenyl)sulfonyl]amino] phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[3-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy ]pentanoic acid methyl ester. 2. Benzimidazoles according to claim 1, characterized in that they are selected from: [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid isopropyl ester, 3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester, 2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester, 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid isopropyl ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid isopropyl ester, 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester, 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester, 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide, N-methoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide, N- (phenylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide, N-hydroxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy ]hexanamide, 7- [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid methyl ester, 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane- acid isopropyl ester, 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester, 6-[[2-phenyl-1-[3-(trifluoromethyl) phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester, 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[ 1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester, 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl] oxy]hexanoic acid, ■ 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane- -acid methyl ester, 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester, 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol- 6-yl]oxy]hexane acid methyl ester, 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester 6-[[1-(4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[ [1-p-methylphenyl)-2-phenyl-1H-.benzimidazol-6-yl]oxy]hexane-acid methyl ester, 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol- 6-yl]oxy]hexane acid isopropyl ester, 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 6-[[1-(4-methylphenyl )-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester , 6-[[1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester, 6-[[1-(3,5-dimethylphenyl)-2-phenyl- 1H-benzimidazol-6-yl]oxy]-hexanoic acid isopropyl ester, 6-[[1-(3-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-( 4-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy ]-hexanoic acid methyl ester, 6-[[1-[3, 4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-[3,4-(methylenedioxy)phenyl]- 2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid, 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester, 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid, 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester, 6-[[1-[4-(N,N-dimethylamino)phenyl ]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy ]hexanoic acid, 6-[[l-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester, 6-[[2-(3-chlorophenyl)-1-phenyl -1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester, 6-[[2 -(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy ]hexane acid isopropyl ester, 6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 6-[[2-(4-methylphenyl)-1-phenyl -1H-benzimidazol-6-yl]oxy]hexane-■ acid isopropyl ester, 6-[[1-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 6-[( 1,2-Diphenyl-5-nitro-1H-benzimidazol-6-yl)oxy]hexane acid methyl ester, 6-[(1,2-diphenyl-5-n itro-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester, 6-[[5-[[(4-bromophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy] hexanoic acid isopropyl ester, 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1, 2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[5-[[(4-chlorophenyl )sulfonyl]amino]-1, 2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[1,2-diphenyl-5-[[(3-methylphenyl)sulfonyl]amino]-1H- benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[1,2-diphenyl-5-[[(4-methylphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[1,2-diphenyl-5-[[(4-methoxyphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6- [ [1,2-diphenyl-5-[[[(4-trifluoromethyl)phenyl]sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[5-[[[4- (acetylamino)phenyl]sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[5-[[bis-(3-chlorophenyl)sulfonyl]amino]-1, 2-Diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[[1,2-diphenyl-5-[(propylsulfonyl)amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6-[ [5-[(benzylsulfonyl)amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 2-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid methyl ester, 3- [2-[(1, 2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]propanoic acid methyl ester, 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6 -yl]oxy]hexanoic acid ethyl ester, 6-[[4-acetyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-(4- methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester, 6-[[2-phenyl-1-[4-(thiomethyl)phenyl]-1H-benzimidazol-5-yl]oxy] -hexanoic acid methyl ester, 6-[[2-phenyl-1-[(4-thiomethyl)phenyl]-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester, 6-[[2-phenyl-1-(3-thienyl) -1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester, 6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid methyl ester, N-(phenylmethoxy)-6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H- benzimidazol-6-yl]oxy]hexanamide, N,N-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide, N-isopropyl-6-[(1, 2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide, 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-pyrrolidin-1-ylhexan-1-one , 5- [.[5- [ [ (4-chlorophenyl) sulfonyl] amino] -1, 2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6-[[5-[[(4-chlorophenyl) sulfonyl]amino]-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-( 4-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[4-(acetyloxy)-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl ]oxy]hexanoic acid methyl ester, 6-[[4-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[4-hydroxy-1-(4- methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid, 6-[[7--methyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester. 3. Benzimidazoles according to claim 1, characterized in that they are selected from: 6-[[2-phenyl-1-(3-pyridyl)-1H-ben.zimidazol-5-yl]oxy]hexane acid methyl ester, 6-[[2-phenyl-1-(3-pyridyl)-1H- benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[2-phenyl-1-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[2-(4 -fluorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 6-[[2-(4-methoxyphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane- acid methyl ester, 6-[[2-(4-bromophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, 6-[[2-[4-(trifluoromethyl)phenyl]-1-phenyl -1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester, 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[ 1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid, 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H- benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester, 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid, 6-[[5- methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester, 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester, 6-[[5-methoxy-1-(4-methylphenyl)-2 -phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester, 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(3,4-dimethylphenyl)-2-phenyl-1H- benzimidazol-6-yl]oxy]hexanoic acid methyl ester-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-2-(4-fluorophenyl)-1-(4 -methoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-(4-methoxyphenyl)- 1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 4- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester, 5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [[5-[[(4-(trifluoromethyl)phenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[5 -[[(4-chlorophenyl)sulfonyl]methylamino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-(indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid, 6 -[[1-(3-fluorophenyl)-2^phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester , 6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6 -yl]oxy]hexane acid methyl ester, 6-[[l-phenyl-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester, N-(cyclopropylmethoxy)-6-[(1 ,2-diphenyl-1H-benzimidazol-6-yl)-oxy]hexanamide, N-isobutoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide, N-(cyclopropylmethoxy )-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide, N-isobutoxy-6-[2-phenyl-1-(3,4 ((5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide, N-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide, N-(3-methoxypropyl)-6-[(1,2-diphenyl-1H -benzimidazol-6-yl)oxy]-hexanamide, N-isobutyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide, 6-[(1,2-diphenyl-1H- benzimidazol-6-yl)oxy]-1-morpholin-1-yl-hexan-1-one, N,N-di-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6 -yl)-oxy]hexanamide, N-isopentyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide, N-(pyridin-2-yl)-6-[( 1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide, N-(pyridin-3-yl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]- hexanamide, N-isopropyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N,N-dimethyl-6-[[1-(3 ,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N,N-diethyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol- 6-yl]oxy]hexanamide, N-isobutyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-cyclopropyl-6-[[ 1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-cyclobuty 1-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-tert-butyl-6-[[1-(3,4- dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, (R)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-1-(2-methoxymethyl)pyrrolidin-1-ylhexan-1-one, N-(3-imidazol-1-ylpropyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-(2-pyridine-2 -ylethyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide, N-(3-methoxypropyl)-6-[[1-(indan -5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]heptanamide, 6-[[1-(4-methylphenyl)-2-(3-pyridyl)-1H-benzimidazol-6-yl] oxy]-hexanoic acid methyl ester, 6-[[1-(4-methylphenyl)-2-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester, 6- [ [1-(4-methylphenyl)-2-(2-thienyl)-1H-benzimidazol-6-yl].oxy]-hexanoic acid methyl ester, 6-[[1-(4-methylphenyl)-2-(3 -thienyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester, 6-[[2-(3-indolyl)-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester, 6-[[1-(4-methylphenyl)-2-(2-furyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester, 6-[[1-(4-methylphenyl)-2-(3- furyl^-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester, 6-[[1-(4-methylphenyl)-2-(5-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy] hexanoic acid methyl ester, 6-[[1-(4-methylphenyl)-2-(3-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester. 4. Use of a compound according to one of claims 1-3 for the preparation of a drug for the treatment or prevention of diseases that are associated with a microglial activation. 5. Pharmaceutical agent, characterized in that it contains one or more compounds according to one of claims 1-3 and one or more carrier substances. 6. Use of a benzimidazole of the general formula II wherein R<1> means a phenyl, naphthyl, fluorenyl, indanyl, pyridyl, thienyl, furyl, indolyl or benzothienyl group which may be substituted with up to three of the following substituents independently of each other: F, Cl, Br, I, XOH, XOR4, XCN, XSR<4>, N02, XNH2, XNHR<4>, XNR<4>R<4>', R<4>, whereby two substituents on R<1>, if they are ortho to each other, can be connected to each other in such a way that together they form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R<2> has the same meaning as R<1>, R3 means one or two substituents which can independently be: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, N02, XNH2, XNHR<4>, XNR<4>R4', XNHS02R< 4> or R<4>, R<4> and R<4>' independently mean C1-4-perfluoroalkyl, C1-6-alkyl, phenyl or phenyl-C1-C4-alkyl, whereby the phenyl groups can be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3 or C2F5/ R<5> and R<5>' independently mean C1-6-alkyl, whereby a carbon atom can be exchanged for 0, S, SO, SO2, NH, NCi-3-alkyl or NCi-3-alkanoyl, C3-7-cycloalkyl -C0-3-alkyl, whereby in a 5-membered cycloalkyl ring one ring member can be an N or an 0 and in a 6- or 7-membered cycloalkyl ring one or two ring members can be N and/or 0, whereby ring nitrogens can possibly be substituted with C1-3-alkyl or C1-3-alkanoyl, phenyl, phenyl-C1-C4-alkyl, pyridyl, pyridyl-C1-C4-alkyl or imidazolyl-C1-C4-alkyl, whereby all previously mentioned alkyl residues can be substituted with up to two substituents of OH, 0Ci-3-alkyl, NH2, NHCi-3-alkyl, NHCi-3-alkanoyl, N (Ci_3-alkyl) 2, N (Ci_3-alkyl) (Ci_3-alkanoyl), COOH, C0NH2, C00Ci-3-alkyl and all previously mentioned phenyl and pyridyl groups can be substituted with one or two substituents from the group consisting of F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5 , CF3, C2F5, or R<5> and R<5>' together with the nitrogen atom form a 7-pyrrolidine, morpholine, piperidine or piperazine ring and may be substituted with C1_4-alkyl, C1-4-alkyl-C0-2-alkyl, Ci -4-Alkoxycarbonyl or aminocarbonyl, A means C1-10-alkanediyl or C2-10-alkenediyl, B stands for COOH, COOR<5>, CONH2, CONHNH2, CONHR<5>, CONR<5>R<5>', CONHOH, CONHOR<5>, S02NH2, S02NHR<5>, S02NR<5>R<5> ', X means a bond, Y means 0, NH, NR<4>, NS02R<4>, whereby the following compounds are excluded: [ (1,2-diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid methyl ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester, 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5- [[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [ [1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid methyl ester, 5-[[1-(4-aminophenyl)-2-phenyl-1H-benzimidazol- 6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[4-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5 -[[1-[4-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [ [1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid methyl ester, 5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol- 6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[3-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5 -[[1-[3-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, for the manufacture of a medicament for the treatment or prevention of diseases associated with a microglial activation.