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

Benzimidazoles, pharmaceutical preparations and their use in the manufacture of a medicament for the treatment of diseases associated with microglia activation Download PDF

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NO326408B1
NO326408B1 NO20023362A NO20023362A NO326408B1 NO 326408 B1 NO326408 B1 NO 326408B1 NO 20023362 A NO20023362 A NO 20023362A NO 20023362 A NO20023362 A NO 20023362A NO 326408 B1 NO326408 B1 NO 326408B1
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benzimidazol
oxy
phenyl
methyl ester
acid methyl
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Wolfgang Halfbrodt
Joachim Kuhnke
Ursula Monning
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Bayer Ip Gmbh
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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

Oppfinnelsen angår nye benzimidazolderivater og anvendelse av benzimidazolderivater for fremstilling av legemidler for behandling og profylakse av sykdommer som er til-knyttet en mikrogliaaktivering. 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.

Nesten alle degenerative sykdommer i det sentrale nervesystem er forbundet med en kronisk betennelse. Et sentralt skritt ved betennelsesutviklingen er aktiveringen av mono-nukleære fagocytære celler, mikrogliaene. Dette finner sted f.eks.„ved.Alzheimers sykdom på grunn av senil plaque, ved Creutzfeldt-Jakobs på grunn av et prionprotein og ved iskemisk slaganfall på grunn av døde celler. Mikrogliaene kan holde seg i aktivert tilstand over et lengre tidsrom i løpet av hvilket de produserer og skiller ut. forskjellige betennelsesfaktorer, f.eks. reaktive oksygen/nitrogenmellomprodukter, proteaser, cytokiner, komplementfaktorer og neurotoksiner. Disse bevirker på sin side neuronal dysfunksjon og degenerering. 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 en mulig behandling av neuroinflammasjon er hittil ikke-steroidale betennelseshemmere (COX II-inhibitorer) blitt beskrevet (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)), Cytokin-Modulatoren (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. og Feuerstein, G.Z., J. Cerebral Blood Flow and Metabolism 19, 819-834 (1999) og Komplement-Kaskaden-Inhibitoren (Chen., 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., og Brunden, K.R., Neurobiol. Aging S., Frederickson, R.C.A., and Brunden, K.R., Neurobiol. Aging

(1996), McGeer, E.G., McGeer, P.L., Drugs 55:739-746 (1998)). Disse stoffer hemmer syntesen eller virkningen av enkelte betennelsesfaktorer. Det hadde imidlertid vært ønskelig å ha stoffer som hemmer et tidligere trinn ved betennelsesutviklingen og dermed hindrer dannelsen eller virkningen av mange betennelsesfaktorer. (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.

Oppfinnelsen angår benzimidazoler som er kjennetegnet ved generell formel: The invention relates to benzimidazoles which are characterized by the general formula:

hvori in which

R<1> betyr en fenyl-, naftyl-, fluorenyl-, indanyl-, pyridyl-, tienyl-, furyl-, indolyl- eller benzotienylgruppe som kan være substituert med inntil tre av de følgende substituenter uavhengig av hverandre: F, Cl, Br, I, XOH, XOR<4>, XCN, XSR<4>, N02, XNH2, XNHR<4>, XNR4R4', R4, hvorved to substituenter på R<1>, dersom de står i ortostilling til hverandre, kan være slik forbundet med hverandre at de sammen danner metandiylbisoksy, etan-1,2-diylbisoksy, propan-1,3-diyl, butan-1,4-diyl, 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 har samme betydning som R<1>, R2 has the same meaning as R<1>,

R3 betyr én eller to substituenter som uavhengig av hverandre kan være: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, N02, XNH2, XNHR<4>, XNR<4>R4', XNHS02R<4> eller R<4>, 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 og R<4>' betyr uavhengig av hverandre Ci-4-perf luor-alkyl, Ci^6-alkyl, fenyl eller fenyl-Ci-C4-alkyl, hvorved fenyl-gruppene kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3 eller C2FS, 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 og R<5>' betyr uavhengig av hverandre Ci-6-alkyl, hvorved et karbonatom kan være utvekslet mot 0, S, SO, S02, NH, NCi_3-alkyl eller NCi_3-alkanoyl, C3_7-sykloalkyl-C0-3-alkyl, hvorved i en 5-leddet sykloalkylring et ringledd kan være et N eller et 0 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

og i en 6- eller 7-leddet sykloalkylring ett eller to ringledd kan være N og/eller 0, hvorved ringnitrogener eventuelt kari være substituert med Ci_3-alkyl eller Ci-3-alkanoyl, fenyl, fenyl-Ci~C4-alkyl, pyridyl, pyridyl-Ci-C4-alkyl eller imidazolyl-Ci-C4-alkyl, 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,

hvorved alle tidligere nevnte alkylrester kan være substituert med inntil to substituenter av 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 og alle tidligere nevnte fenyl- og pyridylgrupper kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2Hs, N02, 0CH3, OC2H5, CF3, C2F5, 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,

eller R<5> og R<5>' danner sammen med nitrogenatomet en 7-pyrrolidin-, morfolin-, piperidin- eller piperazinring og kan være substituert med Ci_4-alkyl, Ci-4-alkoksy-C0-2-alkyl, Ci_4-alkoksykarbonyl eller aminokarbonyl, 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 betyr Ci-io-alkandiyl eller C2_i0-alkendiyl, A means C1-10-alkanediyl or C2-10-alkenediyl,

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

X betyr en binding, X means a bond,

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

hvorved de følgende forbindelser er utelukket: [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyremetylester, 5-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]pentansyremetylester, 4- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butansyreetylester, 5- [[1-(4-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, ■ 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-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(4-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5-[[1-(4-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

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

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

5- [[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

6- [[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(3-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

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

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

De fysiologisk tolererbare salter kan dannes med uorganiske og organiske syrer, som f.eks. oksalsyre, melkesyre, sitronsyre, fumarsyre, eddiksyre, maleinsyre, vinsyre, fosfor-syre, HC1, HBr, svovelsyre, p-toluensulfonsyre, metansulfonsyre. For dannelse av salter av syregrupper er også de uorganiske eller organiske baser egnet som er kjent for dannelse av fysiologisk tolererbare salter, som f.eks. alkalihydroksider, natrium- eller kaliumhydroksid, jordalkalihydroksider som kalsiumhydroksid, ammoniakk, aminer som etanolamin, dietanol-amin, trietanolamin, N-metylglukamin, tris-(hydroksymetyl)-metylamin. 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.

Spesielt foretrukne er de følgende benzimidazoler: [(1, 2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyreisopropylester, 3- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]propansyremetylester, 2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]propansyremetylester, 4- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butansyreisopropyl-ester, 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-difenyl-lH-benzimidazol-6-yl)oksy]pentansyreisopropyl-ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid isopropyl ester,

6- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester, 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyreisopropyl-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-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid, N-metoksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid, N-(fenylmetoksy)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, 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-hydroksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid, 7-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heptansyremetylester, 6-[[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 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-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[2-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6- [ [1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre, 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[1-(4-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(4-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester

6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-t[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-t[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester,

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

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

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

6-[[1-(3-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(3-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

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

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

6-[[1-[3,4-(metylendioksy)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre, 6-[[1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6- [ [2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyre, 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid,

6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

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

6-[[1-[4-(N,N-dimetylamino)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre, 6-[[1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl] - oksy]heksansyreisopropylester, 6-[[1-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[2-(4-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester,

6-[[l-fenyl-2-(4-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

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

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

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

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

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

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

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

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

6-[[1,2-difenyl-5-[[[(4-trifluormetyl)fenyl]sulfonyl]amino]-1H-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[5-[[[4-(acetylamino)fenyl]sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[5-[[bis-(3-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 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-difenyl-5-[(propylsulfonyl)amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[1,2-diphenyl-5-[(propylsulfonyl)amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester,

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

2- [2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]eddiksyre-metylester, 2-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid methyl ester,

3- [2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]propan-syremetylester, 3-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]propanoic acid methyl ester,

6-[[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreetylester, 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid ethyl ester,

6- [ [4-acetyl-l- (4-metylfenyl) -2-f eny'l-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[ [4-acetyl-1-(4-methylphenyl)-2-phenyl-1-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksan-syremetylester, 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexane acid methyl ester,

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

6-[[2-fenyl-l-[(4-tiometyl)fenyl]-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[2-phenyl-1-[(4-thiomethyl)phenyl]-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester,

6- [ [2-fenyl-l-(3-tienyl)-lH-benzimidazol-5-yl]oksy]heksan-syremetylester, 6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-5-yl]oxy]hexane acid methyl ester,

6-[[2-fenyl-l-(3-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester, 6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

4- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butansyremetylester, N-(fenylmetoksy)-6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-1H-benzimidazol-6-yl]oksy]heksanamid, 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-dimetyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, N,N-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide,

N-isopropyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, N-isopropyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide,

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-pyrrolidin-l-ylheksan-l-on, 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-pyrrolidin-1-ylhexan-1-one,

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

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

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

6-[[4-(acetyloksy)-1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[4-(acetyloxy)-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[4-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[4-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[4-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre, 6-[[4-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[7-metyl-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester. 6-[[7-methyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester.

Særlig foretrukne er Particularly preferred are

6-[[2-fenyl-l-(3-pyridyl)-lH-benzimidazol-5-yl]oksy]heksan-syremetylester, 6-[[2-phenyl-1-(3-pyridyl)-1H-benzimidazol-5-yl]oxy]hexane acid methyl ester,

6-[[2-fenyl-l-(3-pyridyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester, 6-[[2-phenyl-1-(3-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[2-fenyl-l-(4-pyridyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester, 6-[[2-phenyl-1-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[2-(4-fluorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-fluorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-metoksyfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-Methoxyphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[2-(4-bromfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-bromophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

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

6-[[1-fenyl-2-(benzotien-2-yl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[l-fenyl-2-(benzotien-2-yl)-lH-benzimidazol-6-yl]oksy]heksan-syre, 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid,

6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyre, 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid,

6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid isopropyl ester,

6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester,

6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester-benzimidazol-6-yl]oksy]heksansyremetylester, 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-klorfenyl)sulfonyl]amino]-2-(4-fluorfenyl)-1-(4-metoksyfenyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-(4-metoksyfenyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 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-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]butansyremetylester, 4- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester,

5- [[5-[t. (4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester, 5- [[5-[h. (4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

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

6- [[5-[[(4-(trifluormetyl)fenyl)sulfonyl]amino]-1-(4-metoksyfenyl) -2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-t[5-[[(4-klorfenyl)sulfonyl]metylamino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[1-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 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-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre, 6-[[1-(3-fluorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 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-nitrofenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

6-[[l-fenyl-2-(3-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-phenyl-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

N-(syklopropylmetoksy)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)-. oksy]heksanamid, N-(cyclopropylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)-. oxy]hexanamide,

N-isobutoksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, N-isobutoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide,

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

N-isobutoksy-6-[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl)oksy]heksanamid, N-isobutoxy-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide,

N-(2-metoksyetyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide,

N-(3-metoksypropyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-(3-methoxypropyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide,

N-isobutyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid, 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-morfolin-l-yl-heksan-l-on, N,N-di-(2-metoksyetyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)-oksy]heksanamid, N-isopentyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, N-(pyridin-2-yl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-(pyridin-3-yl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-isopropyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N,N-dimetyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N,N-dietyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-isobutyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-syklopropyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-syklobutyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-tert.-butyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, 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-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-1-(2-metoksymetyl)pyrrolidin-l-ylheksan-l-on, (R)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-1-(2-methoxymethyl)pyrrolidin-1-ylhexan-1-one,

N-(3-imidazol-l-ylpropyl)-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-(3-imidazol-1-ylpropyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide,

N-(2-pyridin-2-yletyl)-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-(2-pyridin-2-ylethyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide,

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

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

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

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

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

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

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

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

6-[[1-(4-metylfenyl)-2-(5-metyl-2-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[1-(4-methylphenyl)-2-(5-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester,

6-[[1-(4-metylfenyl)-2-(3-metyl-2-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester. 6-[[1-(4-methylphenyl)-2-(3-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Benzimidazolderivatene ifølge oppfinnelsen hemmer aktiveringen av mikroglia og kan derfor anvendes for fremstilling av et legemiddel for behandling eller forebyggelse av sykdommer som er assosiert med en mikroglia. Med mikroglia skal her hjernens 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

makrofager forstås. macrophages are understood.

Denne virkning er overraskende da benzimidazolderivater hittil bare er blitt beskrevet for behandling av tromboser og arterio-sklerose (EP0531883, WO 95/07263, EP0104727, WO 97/12613), zystitis (WO 97/33873) og sykdommer som er assosiert med et amyloidpeptid (US 5 552 426) og en forsterket aktivering av Ca-kanaler (EP520200), men en virkning på mikroglia er ikke kjent. 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.

Oppfinnelsen angår også anvendelse av en benzimidazol med den generelle formel II The invention also relates to the use of a benzimidazole with the general formula II

hvori in which

R<1> betyr en fenyl-, naftyl-, fluorenyl-, indanyl-, pyridyl-, tienyl-, furyl-, indolyl- eller benzotienylgruppe som kan være substituert med inntil tre av de følgende substituenter 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

..uavhengig av hverandre: ..independently of each other:

F, Cl, Br, I, XOH, XOR<4>, XCN, XSR<4>, N02, XNH2, XNHR<4>, XNR4R4', R4, hvorved to substituenter på R<1>, dersom de står i ortostilling til hverandre, kan være slik forbundet med hverandre at de sammen danner metandiylbisoksy, etan-1,2-diylbisoksy, propån-1,3-diyl, butan-1,4-diyl, 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 har samme betydning som R<1>, R2 has the same meaning as R<1>,

R3 betyr én eller to substituenter som uavhengig av hverandre kan være: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, N02, XNH2, XNHR<4>, XNR<4>R<4>', XNHS02R4 eller R<4>, 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>.,og R<4>' betyr uavhengig av hverandre Ci_4-perfluor-alkyl, Ci-6-alkyl, fenyl eller f enyl-Ci-C4-alkyl, hvorved fenyl-gruppene kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3 eller C2F5, 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> og R<5>' betyr uavhengig av hverandre Ci_6-alkyl, hvorved et karbonatom kan være utvekslet mot 0, S, SO, S02, NH, NCi_3-alkyl eller NC!_3-alkanoyl, C3-7-sykloalkyl-C0-3-alkyl, hvorved i en 5-leddet sykloalkylring et ringledd kan være et N eller et 0 og i en 6- eller 7-leddet sykloalkylring ett eller to ringledd kan være N og/eller 0, hvorved ringnitrogener eventuelt kan være substituert med Ci_3-alkyl eller Ci_3-alkanoyl, fenyl, fenyl-Ci-C4-alkyl, pyridyl, pyridyl-Ci-C4-alkyl eller imidazolyl-Ci-C4-alkyl, 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,

hvorved alle tidligere nevnte alkylrester kan være substituert med inntil to substituenter av 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 og alle tidligere nevnte fenyl- og pyridylgrupper kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3, C2F5, 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,

eller R<5> og R<5>' danner sammen med nitrogenatomet en 7-pyrrolidin-, morfolin-, piperidin- eller piperazinring og kan være substituert med Ci_4-alkyl, Ci-4-alkoksy-Co-2-alkyl, Ci_4-alkoksykarbonyl eller aminokarbonyl, 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 betyr Ci_i0-alkandiyl eller C2_i0-alkendiyl, A means C1-10-alkanediyl or C2-10-alkenediyl,

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

X betyr en binding, X means a bond,

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

hvorved de følgende forbindelser er utelukket: [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyremetylester, 5-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]pentansyremetylester, 4- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butansyreetylester, 5- [[1-(4-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 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-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(4-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5-[[1-(4-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

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

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

5- [[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

6- [[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester,

5-[[1-(3-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester,

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

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

for fremstilling av et legemiddel for behandling eller hindring av sykdommer som er assosiert med en mikrogliaaktivering. for the manufacture of a medicament for the treatment or prevention of diseases associated with a microglial activation.

Forbindelsene ifølge oppfinnelsen med den generelle formel II hemmer aktiveringen av mikrogliaaktiveringen. Denne virkning er ny. The compounds according to the invention with the general formula II inhibit the activation of microglial activation. This effect is new.

I eksempel 307 er det beskrevet hvorledes hemmingen av mikrogliaaktivering kan måles. Aktiveringen av mikroglia kan derved finne sted ved hjelp av forskjellige stimuli, som f.eks. A^-peptid (p-amyloid, Araujo, D.M. og Cotman, C.M., Brain Res. 569, 141-145 (1992)), prion-protein, cytokiner eller ved cellefragmenter (Combs, C.K. et al. (1999), J. Neurosci., 19, 928-939, Wood, P.L. (1998) Neuroinflammation: Mechanisms and Management, Humana Press). For eksempel viser forbindelsen i henhold til eksempel 49 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanisopropylester en hemming på IC50 =. 0,75 uM. 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.

Stimuleringen med AØ-peptidet svarer til den patofysio-logiske situasjon ved Alzheimers sykdom. Ved denne test viste stoffene ifølge oppfinnelsen ved stimulering med A(i-peptidet en hemming av mikrogliaaktiveringen. Hemmingen av mikrogliaaktiveringen ved hjelp av stoffene ifølge oppfinnelsen fører til en sterk reduksjon av cytokinproduksjonen og -sekresjonen, f.eks. fra 111(3 og TN Fa (målt ved hjelp av ELISA og mRNA-ekspresjons-analyse) og til en redusert sekresjon av reaktivt oksygen/nitro-gen-mellomprodukter. Samtidig blir også flere betennelsesfaktorer hemmet. 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.

In vivo-virksomheten til stoffene ifølge oppfinnelsen ble påvist ved hjelp av en MCAO-modell i rotter. Denne modell simulerer tilstanden ved et slaganfall. Stoffene ifølge oppfinnelsen reduserer mikrogliaaktiveringen som opptrer ved akutte hjerneskader i dyrenes hjerner. 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.

Oppfinnelsen angår også anvendelsen av forbindelsene ifølge oppfinnelsen med den generelle formel I og den generelle formel II for fremstilling av et legemiddel for behandling eller hindring av sykdommer som er assosiert med en mikrogliaaktivering. Eksempler på slike sykdommer er AIDS-demens, amyotrof lateralsklerose, Creutzfeldt-Jakobs-sykdom, Downs syndrom, diffus Lewy Body-sykdom, Huntingtons sykdom, leukencefalopati, multippel sklerose, Parkinsons sykdom, Picks sykdom, Alzheimers sykdom, slaganfall, temporær lobe-epilepsi og tumorer. 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.

Dessuten angår oppfinnelsen farmasøytiske midler som inneholder én eller flere forbindelser ifølge oppfinnelsen med den generelle formel I og ett eller flere bærerstoffer. De farmasøytiske midler hhv. preparater ifølge oppfinnelsen blir på i og for seg kjent måte fremstilt med de vanlige faste eller flytende bærerstoffer eller fortynningsmidler og de vanlige farmasøytiske og tekniske hjelpestoffer i overensstemmelse med den ønskede tilførselsart med en egnet dosering. De foretrukne preparater består i en anvendelsesform som er egnet for oral, enteral eller parenteral administrering. Slike tilførselsformer er f.eks. tabletter, filmtabletter, dragéer, piller, kapsler, pulver eller depotformer så vel som suppositorier. Tilsvarende tabletter kan fås f.eks. ved- å blande virkestoffet. med kjente hjelpestoffer, f.eks. inerte fortynningsmidler så som dekstrose, sukker, sorbitt, mannitt, polyvinylpyrrolidon, sprengmidler så som maisstivelse eller alginsyre, bindemidler så som stivelse eller gelatiner, glidemidler så som karboksypolymetylen, kar-boksymetylcellulose, celluloseacetatftalat eller polyvinyl-acetat. Tablettene kan også bestå av flere sjikt. 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.

Tilsvarende kan dragéer fremstilles ved overtrekking av kjerner som er blitt fremstilt analogt med tablettene, med midler som er vanlig anvendt for dragéovertrekking, f.eks. polyvinylpyrrolidon eller skjellakk, gummi arabicum, talkum, titan-oksid eller sukker. Derved kan også dragéomhyllingen bestå av flere sjikt, hvorved de hjelpestoffer som er nevnt ovenfor i forbindelse med tablettene, kan anvendes. Kapsler som inneholder virkestoffer, kan f.eks. fremstilles idet man blander virkestoffet med en inert bærer, så som melkesukker eller sorbitt, og innkapsler i gelatinkapsler. 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.

Stoffene ifølge oppfinnelsen kan også i egnede oppløsninger, så som f.eks. fysiologisk koksaltoppløsning, finne anvendelse som infusjons- eller injeksjonsoppløsning. 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 anvendelse er spesielt oljeaktige oppløsninger, som f.eks. oppløsninger i sesamolje, ricinusolje og bomullsfrø-olje, egnet. For å øke oppløseligheten kan oppløsningsfor-midlere, som f.eks. benzylbenzoat eller benzylalkohol, til-settes . 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.

Det er også mulig å innarbeide stoffene ifølge oppfinnelsen i et transdermalt system og dermed tilføre disse transdermalt. Doseringen av stoffene ifølge oppfinnelsen med den generelle formel I og den generelle formel II bestemmes av den behandlende lege og er avhengig bl.a. av det administrerte stoff, adminis-treringsmåten, sykdommen som skal behandles, og hvor alvorlig sykdommen er. Den daglige dose utgjør ikke mer enn 1000 mg, fortrinnsvis ikke mer enn 100 mg, hvorved dosen kan gis som enkeltdose som skal gis én gang, eller som er oppdelt i 2 eller flere dagsdoser. 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.

Forbindelsene med formel I kan foreligge som tauto-merer, stereoisomerer eller geometriske isomerer. Oppfinnelsen omfatter også alle mulige isomerer, så som E- og Z-isomerer, S-og R-enantiomerer, diastereomerer, racemater og blandinger av disse innbefattende de tautomere forbindelser... Isomerblandingene kan separeres i enantiomerene hhv. E/Z-isomerene i henhold til vanlige metoder, som f.eks. krystallisasjon, kromatografi eller saltdannelse. 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.

Fremstillingen av forbindelsene ifølge oppfinnelsen finner sted analogt med kjente fremgangsmåter som f.eks. er beskrevet i EP 531 883. Dersom fremstillingen av utgangsforbindelsene ikke er beskrevet, er utgangsforbindelsene kjente og kan kjøpes eller fremstillingen av disse finner sted analogt med de hittil beskrevne fremgangsmåter. Nedenfor blir fremstillingen av enkelte forhåndstrinn, mellomprodukter og produkter beskrevet som eksempler. 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.

Ved fremstillingen av stoffene ifølge oppfinnelsen betjener man seg f.eks. av de følgende fremgangsmåter: In the production of the substances according to the invention, one uses e.g. of the following procedures:

Generell arbeidsinstruks 1: General work instructions 1:

Reduksjon av nitrogrupper, hydrering av olefiniske dobbelt-bindinger og hydrogenolytisk spaltning av benzyletere Reduction of nitro groups, hydrogenation of olefinic double bonds and hydrogenolytic cleavage of benzyl ethers

Forbindelsen som skal reduseres, blir oppløst i etylacetat, tetrahydrofuran, metanol eller etanol eller blandinger av løsningsmidlene og hydrert på 2-5% (basert på nitroforbindelsen) av palladium-på-kull (10%) ved normalt trykk. Etter avsluttet hydrogenopptak foretas avsugning, og resten vaskes med etylacetat eller metanol eller etanol, og filtratet konsentreres i vakuum. Råproduktet blir som regel omsatt uten ytterligere rensing. 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.

Generell arbeidsinstruks 2: General work instructions 2:

Reduksjon av nitrogrupper Reduction of nitro groups

9,2 g jern (II)sulfat forelegges på forhånd i 30 ml vann og 9 ml ammoniakkoppløsning. Til dette blir en oppløsning av 3,6 mmol av nitroforbindelsen i 100 ml etanol dråpevis tilsatt og suspensjonen intensivt omrørt i 1 h ved 70 °C. Deretter foretas bunnavsetning, frafiltrering fra det faste stoff, vidtgående konsentrering av filtratet, tilsetning av vann og ekstraksjon tre ganger med etylacetat. De kombinerte ekstrakter tørkes over natriumsulfat og konsentreres i vakuum. Aminoforbindelsen blir videre bearbeidet som råprodukt. 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.

Generell arbeidsinstruks 3: General work instructions 3:

Syklisering.til benzimidazoler med ortoestere Cyclization.to benzimidazoles with orthoesters

10 mmol av et 1,2-diaminobenzenderivat oppløses i 25 ml etanol. Til dette tilsetter man dråpevis 47 ml av en 0,8 M eterisk HCl-oppløsning, omrører i 30 minutter og konsentrerer deretter i vakuum inntil tørrhet. Resten tas opp i 230 ml metanol og forsynes med 6 ml trimetylortobenzoat eller den tilsvarende mengde av en annen ortoester. Man oppvarmer i 2-8 h inntil tilbakeløp, heller over på mettet natriumhydrogenkar-bonatoppløsning etter avkjølingen, ekstraherer tre ganger med etylacetat, tørker de kombinerte ekstrakter over natriumsulfat og konsentrerer i vakuum. Resten blir renset ved hjelp av krystallisasjon eller søylekromatografi på kiselgel. 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.

Generell arbeidsinstruks 4: General work instructions 4:

Syklisering til benzimidazoler med iminoesterhydroklorider Cyclization to benzimidazoles with iminoester hydrochlorides

1,2 mmol av et 1,2-diaminobenzenderivat oppløses i 5 ml tetrahydrofuran, forsynes med 1,5 mmol av et benzimidathydroklorid, og blandingen omrøres i 15 h. Chargen forsynes med 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

mettet natriumhydrogenkarbonatoppløsning, fortynnes med vann og ekstraheres tre ganger med etylacetat. De kombinerte, organiske faser blir vasket tre ganger med 1 N vandig saltsyre og én gang med mettet natriumkloridoppløsning, tørket over natriumsulfat, filtrert over en fritte med kiselgel og oppløsningen konsentrert til tørrhet. Produktet krystalliseres fra diisopropyleter. 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.

Generell arbeidsinstruks 5: General work instructions 5:

Syklisering til benzimidazoler via karboksylsyreanilider Cyclization to benzimidazoles via carboxylic acid anilides

4,7 mmol av et 1,2-diaminobenzenderivat oppløses i 4.7 mmol of a 1,2-diaminobenzene derivative are dissolved in

20 ml diklormetan, forsynes med 14 mmol trietylamin og langsomt med 6 mmol karboksylsyreklorid, og blandingen omrøres i 15 h. Chargen forsynes med mettet natriumbikarbonatoppløsning, fortynnes med vann og ekstraheres to ganger med diklormetan. De kombinerte, organiske faser vaskes med vann og med mettet natriumkloridoppløsning, tørkes over natriumsulfat og konsentreres i vakuum. Det gjenværende rå karboksylsyreanilid blir tatt opp i en 9:1-blanding av metanol og konsentrert saltsyre og oppvarmet i 1 h'inntil tilbakeløp. Reaksjonsblandingen blir 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

.etter- avkjøling langsomt innført i mettet natriumbikarbonat- .after- cooling slowly introduced into saturated sodium bicarbonate-

oppløsning, fortynnet med vann og ekstrahert tre ganger med diklormetan. De kombinerte, organiske faser vaskes med mettet natriumkloridoppløsning, tørkes over natriumsulfat og konsentreres i vakuum. Resten blir om nødvendig renset ved hjelp av krystallisasjon eller søylekromatografi på kiselgel. 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.

Generell arbeidsinstruks 6: General work instructions 6:

Eterspaltning med hydrobromsyre Ether cleavage with hydrobromic acid

5 g arylmetyleter forsynes med 160 ml 48%-ig vandig HBr og oppvarmes i 1-5 h inntil tilbakeløp. Etter avkjølingen foretas filtrering. Resten tas^ppp i etylacetat og ekstraheres tre ganger med mettet natriumbikarbonatoppløsning. Etter tørking over natriumsulfat foretas konsentrering i vakuum. Resten blir om nødvendig renset ved hjelp av krystallisasjon eller søyle-kromatografi på kiselgel,. 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.

Generell arbeidsinstruks 7: General work instructions 7:

Eterspaltning med bortribromid Ether cleavage with boron tribromide

1,86 mmol arylmetyleter oppløses i 18 ml diklormetan og forsynes langsomt med 7,4 ml av en 1 M oppløsning av bortribromid i diklormetan ved -35 °C. Man lar blandingen henstå i 12-15 h ved -30 °C og forsyner deretter med mettet natriumbikar-bonatoppløsning, ekstraherer tre ganger med diklormetan, tørker de kombinerte ekstrakter over natriumsulfat og konsentrerer i vakuum. Resten blir om nødvendig renset ved hjelp av søylekroma-tograf i på silikagel. 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.

Generell arbeidsinstruks: General work instructions:

Alkylering av hydroksybenzimidazolderivater og fenolderivater med alkylhalogenider Alkylation of hydroxybenzimidazole derivatives and phenol derivatives with alkyl halides

En oppløsning av 1,85 mmol av hydroksybenzimidazol-derivatet i 12 ml N,N-dimetylformamid forsynes med 1,85 mmol cesiumkarbonat, og 2,24 mmol alkylbromid eller alkyljodid. Ved anvendelse av alkylbromidene blir valgfritt 1,85 mmol natriumjodid tilsatt. Man omrører i 12-96 h, heller deretter ut på vann, tar opp med etylacetat, vasker den organiske fase fire ganger med vann, tørker denne over natriumsulfat og konsentrerer i vakuum. 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.

Alternativt til denne vandige opparbeidelse kan man forsyne reaksjonsblandingen med diklormetan, foreta separering fra de utfallende salter ved hjelp av filtrering og konsentrere filtratet i vakuum. 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.

Uavhengig av opparbeidelsesmetoden blir resten renset ved hjelp av krystallisasjon eller søylekromatografi på silikagel. Regardless of the preparation method, the residue is purified using crystallization or column chromatography on silica gel.

Generell arbeidsinstruks 9: General work instructions 9:

Forsåpning av karboksylsyrealkylestere Saponification of carboxylic acid alkyl esters

0,77 mmol av karboksylsyrealkylesteren oppløses i 5 ml metanol og 5 ml tetrahydrofuran og forsynes med 5 ml av en 0,5 N vandig litium- eller natriumhydroksidoppløsning. Etter omrøring i 2-12 h foretas en så sterk konsentrering i vakuum som mulig, og det nøytraliseres ved tilsetning av vandig saltsyre og ekstraheres med etylacetat. Man tørker over natriumsulfat og konsentrerer i vakuum. Resten blir om nødvendig renset ved hjelp av søylekromatografi på silikagel. 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.

Generell arbeidsinstruks 10: General work instruction 10:

Forestring av karboksylsyrer Esterification of carboxylic acids

0,2 mmol karboksylsyre oppløses i 1 ml primær eller sekundær alkohol, forsynes med to dråper konsentrert svovelsyre og omrøres i 12 h ved 60 °C. Chargen blir deretter forsynt med mettet kaliumbikarbonatoppløsning, fortynnet med vann og ekstrahert tre ganger med etylacetat. Etter vasking av de kombinerte ekstrakter med mettet natriumkloridoppløsning og tørking over natriumsulfat foretas konsentrering i vakuum, og resten krystalliseres fra diisopropyleter. 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.

Generell arbeidsinstruks 11: General work instructions 11:

Reduksjon av karboksylsyrealkylestere med litiumaluminiumhydrid Reduction of carboxylic acid alkyl esters with lithium aluminum hydride

0,15 mmol karboksylsyreester oppløses i tetrahydrofuran og forsynes med 0,09 mmol litiumaluminiumhydrid. Man omrører i 1-48 h, tilsetter vann og ekstraherer tre ganger med diklormetan. Etter tørking av de kombinerte, organiske faser over natriumsulfat konsentrerer mari i vakuum. Resten blir om nød-vendig renset ved hjelp av krystallisasjon eller søylekromato-graf i på silikagel.. 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.

Generell arbeidsinstruks 12: General work instruction 12:

Wittig-reaksjon av benzimidazolkarbaldehyder med (u-karboksy-alkyl)trifenylfosfoniumbromider og forestring med metanol 2 mmol av (o-karboksyalkyl)trifenylfosfoniumbromidet blir i 2,5 ml dimetylsulfoksid og 2,5 ml tetrahydrofuran forsynt med 4 mmol kalium-tert.-butylat ved 0 °C og omrørt i 30. minutter ved T>10 °C. Deretter tilsetter man en oppløsning av 0,67 mmol av aldehydet i 2 ml tetrahydrofuran og omrører i 3 h ved 20 °C. Chargen blir deretter forsynt med mettet ammoniumkloridoppløs-ning, fortynnet med vann og ekstrahert tre ganger med etylacetat. Etter tørking av de kombinerte, organiske faser over natriumsulfat foretas konsentrering i vakuum. Resten blir opp-løst i 15 ml metanol, forsynt med to dråper konsentrert svovelsyre og får henstå i 48-72 h. Etter konsentrering i vakuum blir resten renset ved hjelp av søylekromatografi på silikagel. 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.

Generell arbeidsinstruks 13: General work instruction 13:

Omsetning av aminobenzimidazoler med alkyl- og arylsulfonsyre-halogenider 47 umol aminobenzimidazolderivat oppløses i 0,5 ml diklormetan, forsynes med 51 umol trietylamin og 51 umol alkyl-eller arylsulfonsyrehalogenid, og reaksjonsblandingen omrøres i 2-15 h. For opparbeidelsen tilsetter man mettet natriumbikar-bonatoppløsning, ekstraherer tre ganger med diklormetan, vasker de kombinerte, organiske faser med vann, tørker over natriumsulfat og konsentrerer i vakuum. Resten renses ved hjelp av krystallisasjon eller søylekromatografi på silikagel. 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.

Generell arbeidsinstruks 14: General work instructions 14:

Kobberformidlet O- eller N-arylering av benzimidazoler Copper-mediated O- or N-arylation of benzimidazoles

5 mmol av et N-usubstituert benzimidazolderivat eller et N-arylsubstituert hydroksybenzimidazolderivat oppløses i 5 mmol of an N-unsubstituted benzimidazole derivative or an N-aryl substituted hydroxybenzimidazole derivative are dissolved in

20 ml diklormetan. Man tilsetter 10 mmol av en arylborsyre, 20 ml of dichloromethane. 10 mmol of an arylboric acid are added,

5 mmol vannfritt kobber(II)acetat, 10 mmol pyridin eller trietylamin og ca. 2,5 g molekylsil (4), omrører i 48-72 h under utelukkelse av fuktighet, tilsetter deretter silikagel, konsentrerer i vakuum inntil tørrhet og renser det gjenværende pulver ved hjelp av kromatografi på silikagel. Regioisomere N-aryleringsprodukter blir om nødvendig separert ved hjelp av HPLC. 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.

Generell arbeidsinstruks 15: General work instructions 15:

Basekatalysert N-substitusjon av benzimidazoler Base-catalyzed N-substitution of benzimidazoles

5 mmol av et N-usubstituert benzimidazolderivat opp-løses i 20 ml dimetylacetamid. Man tilsetter 25 mmol natriumhydrid og 20 mmol av et elektronfattig aryl- eller heteroaryl-halogenid og oppvarmer i 48-72 h under utelukkelse av fuktighet inntil tilbakeløp, tilsetter deretter silikagel, konsentrerer til tørrhet i vakuum og renser det gjenværende pulver ved hjelp av kromatografi på silikagel. Regioisomere N-aryleringsprodukter blir om nødvendig separert ved hjelp av HPLC. 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.

Generell arbeidsinstruks 16: General work instructions 16:

Syklisering til benzimidazoler med aldehyder Cyclization to benzimidazoles with aldehydes

1 mmol av et 1,2-diaminobenzenderivat oppløses i 3 ml nitrobenzen. Til dette tilsetter man 1 mmol av et aryl- hhv. heteroarylaldehyd. Man oppvarmer i 2-6 h til 150 °C og lar blandingen avkjøle. Resten blir uten videre opparbeidelse renset direkte ved hjelp av søylekromatografi på silikagel. 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.

Generell arbeidsinstruks 17: General work instructions 17:

Overføring av karboksylsyrer til karboksylsyreamider Transfer of carboxylic acids to carboxylic acid amides

0,25 mmol av en karboksylsyre oppløses i 3 ml N,N-dimetylformamid, forsynes med 0,38 mmol av et primært eller sekundært amin, 0,5 mmol trietylamin og 0,25 mmol difenylfos-forylazid, og blandingen omrøres i 2 d. For opparbeidelsen tilsetter man vann, ekstraherer tre ganger med etylacetat, vasker de kombinerte, organiske faser med vann, tørker over natriumsulfat og konsentrerer i vakuum. Resten renses ved hjelp av søylekromatografi på silikagel. 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.

Generell arbeidsinstruks 18: General work instructions 18:

Overføring av karboksylsyreestere til karboksylsyreamider Transfer of carboxylic acid esters to carboxylic acid amides

0,36 mmol av et amin oppløses i 3 ml toluen og forsynes under avkjøling i isbad dråpevis med 0,18 ml av en 2 M oppløs-ning av trimetylaluminium i toluen. Man tilsetter en oppløsning av 0,33 mmol av karboksylsyremetylesteren i 3 ml toluen og omrører i 2-8 h ved 95 °C. For opparbeidelsen tilsetter man vann etter avkjølingen, ekstraherer tre ganger med etylacetat, vasker ' de kombinerte, organiske faser med mettet natriumkloridoppløs- 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, tørker over natriumsulfat og konsentrerer i vakuum. Resten renses ved'hjelp av søylekromatografi på silikagel. ning, drying over sodium sulfate and concentrating in vacuo. The residue is purified using column chromatography on silica gel.

Eksempel 1 Example 1

[ (1,2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyreisopropylester ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol (Benincori, T.; Sannicolo, F.; J. Heterocycl. Chem.; 25; 1988; 1029-1033) med bromeddiksyreisopropylester i henhold til den generelle arbeidsinstruks 8. [(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.

Smp. 137-138 °C. Temp. 137-138 °C.

Eksempel 2 Example 2

[ (1,2-difenyl-lH-benzimidazol-6-yl)oksy]etan-1-ol ble erholdt ved omsetning av [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyremetylester (DE 4330959) i henhold til den generelle arbeidsinstruks 11. [(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 (D6-DMSO): 5 = 3,72 ppm t (J = 7,5 Hz, 2H); 4,02 t (J = 7,5 Hz, 2H); 6,72 d (J = 2 Hz, 1H); 7,10 dd (J = 8, 2 Hz, 1H) ; 7,38-7,68 m (10H); 7,76 d (J = 8 Hz, 1H). <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).

Eksempel 3 Example 3

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

0,5 g 1,2-difenyl-6-hydroksy-lH-benzimidazol ble omsatt med 3-(brompropoksy)-tert.-butyldimetylsilan i henhold til den generelle arbeidsinstruks 8. Etter kromatografi på silikagel tok man opp i 2,5 ml metanol, tilsatte 0,4 ml konsentrert saltsyre og lot omrøre i 2 h ved 20 °C. Man helte ut på mettet, vandig natriumbikarbonatoppløsning, ekstraherte tre ganger med etylacetat, vasket de kombinerte ekstrakter med mettet, vandig natriumkloridoppløsning, tørket over natriumsulfat og konsentrerte i vakuum. 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.

Smp. 191-193 °C. Temp. 191-193 °C.

Eksempel 4 Example 4

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

100 mg 3-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-propan-l-ol ble forelagt på forhånd i 2,5 ml aceton og forsynt ved -15 °C med 0,15 ml av en oppløsning av Jones-reagens (fremstilt av 0,27 g krom(VI)oksid, 1 ml vann og 0,23 ml konsentrert 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

svovelsyre). Etter omrøring i 3,5 h ved -15 °C ble bråkjøling foretatt ved tilsetning av isopropanol. Man fortynnet med vann, ekstraherte tre ganger med diklormetan, tørket de kombinerte, organiske faser over natriumsulfat og konsentrerte i vakuum. Resten ble renset ved hjelp av kromatografi på silikagel. <1>H-NMR (De-DMSO): 5 = 2,60 ppm t (J = 7,5 Hz, 2H); 4,15 t (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). 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).

Eksempel 5 Example 5

3- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]propansyremetylester 45 mg 3- [ (1,2-difenyl-lH-benzimidazol-6-yl)oksy]-propansyre ble oppløst i 0,5 ml N,N-dimetylformamid og forsynt med 41 mg cesiumkarbonat og 10 ul metyljodid. Man lot omrøre i 2 d, fortynnet med diklormetan, filtrerte, konsentrerte filtratet i vakuum og kromatograferte resten på silikagel. 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.

Smp. 120-121 °C. Temp. 120-121 °C.

Eksempel 6 Example 6

2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]propansyremetylester ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 2-brompropansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 .

Smp. 132-135 °C. Temp. 132-135 °C.

Eksempel 7 Example 7

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

ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 4-brombutansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 89-91 °C. Temp. 89-91 °C.

Eksempel 8 Example 8

4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butan-l-ol ble erholdt ved omsetning av 4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butansyremetylester i henhold til den generelle arbeidsinstruks 11. ...Smp.' 159-160 PC. 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.

Eksempel 9 Example 9

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

50 mg 4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butan-l-ol ble oppløst i 1 ml diklormetan, forsynt med 0,34 ml pyridin og 20 ul acetylklorid og omrørt i 15 h. Man tilsatte mettet ' natriumbikarbonatoppløsning, fortynnet med vann, ekstraherte to ganger med diklormetan, vasket de kombinerte, organiske faser med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrerte i vakuum. Resten ble renset ved hjelp av tykk-sjiktskromatografi. n 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

Smp. 68-69 °C. Temp. 68-69 °C.

Eksempel 10 Example 10

Pivalinsyre-[4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]but-l-yl]ester Pivalic acid-[4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]but-1-yl]ester

ble analogt med instruksen angitt i eksempel 9, fremstilt fra 50 mg 4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butan-l-ol, 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 pyridin og 22 pl trimetyleddiksyreklorid. Smp. 104-106 °C. 0.34 ml of pyridine and 22 µl of trimethylacetic acid chloride. Temp. 104-106 °C.

Eksempel 11 Example 11

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

100 mg 4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]butan-l-ol ble oppløst i 4 ml diklormetan, forsynt med 0,1 ml trietylamin og 20 mg metylisocyanat og omrørt i 15 h. Man tilsatte ytterligere 0,1 ml trietylamin og 20 mg metylisocyanat, lot omrøre i 20 h og konsentrerte deretter i vakuum. Resten ble renset ved hjelp av kromatografi på silikagel. 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.

Smp. 124-126 °C. , Temp. 124-126 °C. ,

Eksempel 12 Example 12

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

ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 5-brompentansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 91-92 °C. Temp. 91-92 °C.

Eksempel 13 Example 13

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3).: 8 = 1,44-1,56 m (2H) ; 1,64-1,85 m (4H) ; 2,33 t (J = 7,5 Hz, 2H); 3,66 s (3H); 3,93 t (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); 7,43-7,58 m (5H); 7,76 d (J = 8 Hz, 1H). 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).

Eksempel 14 Example 14

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

ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3) : 6 = 1,22 ppm d (J = 7,5 Hz, 6H) ; 1, 43-1,56 m (2H); 1,62-1,87 m (4H); 2,30 t (J = 7,5 Hz, 2H); 3,93 t (J = 7,5 Hz, 2H); 5,01 sp (J = 7,5 Hz, 1H); 6,69 d (J = 2 Hz, 1H); <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); 7,25-7,38 m (5H); 7,43-7,55 m (5H); 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). 7.75 d (J = 8 Hz, 1H).

Eksempel 15 Example 15

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyre ble erholdt ved omsetning av 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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): 5 = 1,35-1,49 ppm m (2H); 1,50-1,63 m (2H); <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 t (J = 7,5 Hz, 2H); 3,92 t (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). 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).

Eksempel 16 Example 16

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-l-ol ble erholdt ved omsetning av 6-[(1, 2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. 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_ (CDCI3) : 5 = 1,35-1, 85 ppm m (8H) ; 3,67 t (J = 7,5 Hz, 2H); 3,98 t "(J = 7,5. Hz, 2H); 6,70 d (J = 2 Hz, 1H) ; 6,98 dd (J- <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); 7,24-7,38 m (5H); 7,45-7,58 m (5H); 7,75 d (J = 8 Hz, 1H). = 8.2 Hz, 1H); 7.24-7.38m (5H); 7.45-7.58m (5H); 7.75 d (J = 8 Hz, 1H).

Eksempel 17 Example 17

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

a) 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksannitril ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 6-bromheksannitril i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 108-112 °C. Temp. 108-112 °C.

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

Til en oppløsning av 50 mg 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksannitril i 1 ml metanol tilsatte man 18 mg kaliumkarbonat og 40 ul 30%-ig hydrogensuperoksidoppløs-ning og omrørte i 24 h. Man rørte deretter iskald, vandig natriumtiosulfatoppløsning inn og ekstraherte tre ganger med etylacetat. Etter tørking over natriumsulfat ble konsentrering foretatt i vakuum og resten kromatografert på silikagel. 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 (CDC13) : 5 = 1,48-1, 60 ppm m (2H) ; 1, 65-1, 87 m (4H); 2,25 t (J = 7,5 Hz, 2H); 3,94 t (J = 7,5 Hz, 2H); 5,30-5,53 bred (2H); 6,68 d (J = 2 Hz, 1H); 6,95 dd (J = 8, 2 Hz, 1H); 7,23-7,38 m (5H); 7,42-7,58 m (5H); 7,75 d (J = 8 Hz, 1H). <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).

Eksempel 18 Example 18

N-metoksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid N-methoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

100 mg 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyre ble oppløst i 2 ml tetrahydrofuran, forsynt med 39 mg karbonyldiimidazol, omrørt i 30 min ved 20 °C og deretter oppvarmet i 30 min inntil tilbakeløp. Ved 20 °C tilsatte man så 21 mg 0-metylhydroksylaminhydroklorid og lot omrøre i 18 h. Reaksjonsblandingen ble fortynnet med etylacetat og vasket med 2 N vandig saltsyre og mettet kaliumbikarbonatoppløsning. Etter tørking over natriumsulfat ble det konsentrert i vakuum og resten kromatografert på silikagel. 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.

Smp. 144-145 °C. Temp. 144-145 °C.

Eksempel 19 Example 19

N-(fenylmetoksy)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid N-(phenylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

ble erholdt ved omsetning av 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyre med O-benzylhydroksylaminhydroklorid i henhold til den angitte arbeidsinstruks i eksempel 18. 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.

Smp. 144 °C. Temp. 144 °C.

Eksempel 20 Example 20

N-hydroksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid 23 mg N-(fenylmetoksy)-6-[(1,2-difenyl-lH-benzimidazol-6- yl)oksy]heksanamid ble oppløst i 4 ml etanol, forsynt med 15 mg palladium-på-kull (10%) og omrørt i 3 h under en hydrogen-atmosfære. Etter fraskillelse fra katalysatoren ble det konsentrert i vakuum og resten krystallisert fra dietyleter. 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.

Smp. 83-85 °C. Temp. 83-85 °C.

Eksempel 21 Example 21

7- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heptansyremetylester ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 7-bromheptansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 .

Smp. 77-80 °C. Temp. 77-80 °C.

Eksempel 22 Example 22

7-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heptansyre ble erholdt ved omsetning av 7-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heptansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 142-145 °C. Temp. 142-145 °C.

Eksempel 23 Example 23

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

ble erholdt ved omsetning av 7-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heptansyre med isopropanol i henhold til den generelle arbeidsinstruks 10. was obtained by reacting 7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid with isopropanol according to the general work instructions 10.

Smp. 98-100 °C. Temp. 98-100 °C.

Eksempel 24 Example 24

6-[[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

ble erholdt ved omsetning av 6-hydroksy-l-(3-nitrofenyl)-2-fenyl-lH-benzimidazol (DE 4330959) med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 111-113 °C. Temp. 111-113 °C.

Eksempel 25 Example 25

6-[[2-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

a) (5-metoksy-2-nitrofenyl)[(3-trifluormetyl)fenyl]amin a) (5-Methoxy-2-nitrophenyl)[(3-trifluoromethyl)phenyl]amine

2 g 3-fluor-4-nitroanisol og 16 ml 3-(trifluormetyl)-anilin ble omrørt i 72 h ved 140 °C. Chargen ble deretter fortynnet med etylacetat, vasket ti ganger med 4 N vandig saltsyre og én gang med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum, og resten ble kromato-graf ert på silikagel. <1>H-NMR (CDC13) : 5 = 3,78 ppm s (3H); 6,42 dd (J = 8, 2 Hz, 1H); 6,60 d (J = 2 Hz, 1H); 7,45-7,60 m (4H); 8,22 d (J = 8 Hz, 1H); 9,78 s (bred)(1H). b) 6-metoksy-2-fenyl-l-[(3-trifluormetyl)fenyl]-lH-benzimidazol ble erholdt ved hydrering av (5-metoksy-2-nitrofenyl) [ (3-tri-fluormetyl)fenyl]amin i henhold til den generelle arbeidsinstruks 1 og påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks. 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.

Smp. 135-137 °C. c) 6-hydroksy-2-fenyl-1-[(3-trifluormetyl)fenyl]-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-2-fenyl-1-[(3-trifluor-metyl) fenyl] -lH-benzimidazol i henhold til den generelle arbeidsinstruks 6. 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.

^-NMR (D6-DMSO) : 5 = 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 (bred) (1H) . 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-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

ble erholdt ved omsetning av 6-hydroksy-2-fenyl-1-[(3-trifluor-metyl) fenyl] -lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 106-108 °C. Temp. 106-108 °C.

Eksempel 26 Example 26

6-[[2-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester

ble erholdt ved omsetning av 6-hydroksy-2-fenyl-1-[(3-trifluor-metyl) f enyl] -lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 113-115 °C. Temp. 113-115 °C.

Eksempel 27 Example 27

6-[[2-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyre 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble erholdt ved omsetning av 6-[[2-fenyl-1-[3-(trifluormetyl)-fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 156-158 °C. Temp. 156-158 °C.

Eksempel 28 Example 28

6-[[2-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksan-l-ol 6-[[2-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]-oxy]hexan-1-ol

ble erholdt ved omsetning av 6-[[2-fenyl-l-[3-(trifluormetyl)-fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. 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.

Smp. 143-145 °C. Temp. 143-145 °C.

Eksempel 29 Example 29

6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 3-(5-metoksy-2-nitrofenyl)aminobenzonitril a) 3-(5-Methoxy-2-nitrophenyl)aminobenzonitrile

2 g 3-fluor-4-nitroanisol og 15 ml 3-aminobenzonitril 2 g of 3-fluoro-4-nitroanisole and 15 ml of 3-aminobenzonitrile

ble omrørt ved 140 °C i 65 h. Chargen ble deretter fortynnet med etylacetat, vasket tre ganger med vann og én gang med mettet 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

natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum, og resten ble kromatografert på silikagel. sodium chloride solution, dried over sodium sulfate and concentrated in vacuo, and the residue was chromatographed on silica gel.

Smp. 157-158 °C. b) 6-metoksy-l-(3-cyanfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved hydrering av 3-(5-metoksy-2-nitrofenyl)aminobenzonitril i henhold til den generelle arbeidsinstruks 1 og påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. Ved sykliseringen ble som avvik fra den generelle arbeidsinstruks tetrahydrofuran anvendt som løs-ningsmiddel .-- . „ 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.-- . "

Smp. 185-191 °C (dekomp.). Temp. 185-191 °C (decomp.).

c) 6-hydroksy-l-(3-cyanfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-l-(3-cyanfenyl)-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 7. Smp. 216-218 °C. 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.

6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syrerne tyle s ter The 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acids tyles

ble erholdt ved omsetning av 6-hydroksy-l-(3-cyanfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 115-118 °C. Temp. 115-118 °C.

Eksempel 30 Example 30

6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

ble erholdt ved omsetning av 6-hydroksy-l-(3-cyanfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 101-102 °C. Temp. 101-102 °C.

Eksempel 31 Example 31

6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 99-101 °C. Temp. 99-101 °C.

Eksempel 32 Example 32

6-[ [1-(4-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

1) 4-(5-metoksy-2-nitrofenyl)aminobenzonitril 1) 4-(5-Methoxy-2-nitrophenyl)aminobenzonitrile

2 g 3-fluor-4-nitroanisol og 15 ml 4-aminobenzonitril ble omrørt i 22 h ved 140 °C. Chargen ble deretter fortynnet med etylacetat, vasket tre ganger med 2 N vandig saltsyre, tre ganger med vann og én gang med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum, og resten ble kromatografert på silikagel. 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 (CDC13) : 6 = 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 (bred)(1H). b) 6-metoksy-l-(4-cyanfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved hydrering av 4-(5-metoksy-2-nitrofenyl)aminobenzonitril i henhold til den generelle arbeidsinstruks 1 og påfølgende syklisering med trietylortobenzoat i. henhold til den generelle arbeidsinstruks 3. Ved sykliseringen ble til forskjell fra den generelle arbeidsinstruks tetrahydrofuran anvendt som løsningsmiddel. <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 (CDCI3) : 5 = 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-hydroksy-l-(4-cyanfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-l-(4-cyanfenyl)-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 7. Smp. 266-268 °C. <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-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

ble erholdt ved omsetning av 6-hydroksy-l-(4-cyanfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 145-148 °C. Temp. 145-148 °C.

Eksempel 33 Example 33

6-[[1-(4-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

ble erholdt ved omsetning av 6-hydroksy-l-(4-cyanfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8.. 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..

Smp. 102-103 °C. Temp. 102-103 °C.

Eksempel 34 Example 34

6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester a) 1-(3-klorfenyl)-6-metoksy-2-fenyl-lH-benzimidazol ble erholdt ved reduksjon av (3-klorfenyl)-(5-metoksy-2-nitrofenyl)amin (Belton, Mc Inerney; Proe. R. Ir. Acad. Sect. B; 69; 1970; 21,27) i henhold til den generelle arbeidsinstruks 2 og med påfølgende.syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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.

Smp. 140-143 °C. b) 1-(3-klorfenyl)-6-hydroksy-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-l-(3-klorfenyl)-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 6. Smp. 210-214 °C. 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-klorfenyl)-2-fenyl-lH-benzimidazol^6-yl]oksy]heksan-syremetylester 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol^6-yl]oxy]hexane acid methyl ester

ble erholdt ved omsetning av 1-(3-klorfenyl)-6-hydroksy-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 101-105 °C. Temp. 101-105 °C.

Eksempel 35 Example 35

6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid isopropyl ester

ble erholdt ved omsetning av 1-(3-klorfenyl)-6-hydroksy-2-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 107-112 °C. Temp. 107-112 °C.

Eksempel 36 Example 36

6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning 6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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 t (J = 7,5 Hz, 2H); 3,96 t (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). <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).

Eksempel 37 Example 37

6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-l-ol 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

ble erholdt ved omsetning av 6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. 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 (CDC13) : 5 = 1,38-1, 88 ppm m (8H); 3,67 t (J = 7,5 Hz, <1>H-NMR (CDCl 3 ): δ = 1.38-1.88 ppm m (8H); 3.67 h (J = 7.5 Hz,

2H); 3,96 t (J = 7,5 Hz, 2H); 6,70 d (J = 2 Hz, 1H); 6,97 dd (J 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) . = 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) .

Eksempel 38 Example 38

6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester a) 1-(4-klorfenyl)-6-metoksy-2-fenyl-lH-benzimidazol ble erholdt ved reduksjon av (4-klorfenyl)-(5-metoksy-2-nitrofenyl)amin (Kottenhahn et al.; J. Org. Chem.; 28; 1963; 3114, 3118) i henhold til den generelle arbeidsinstruks 2 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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 (CDCI3) : 5 = 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-klorfenyl)-6-hydroksy-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-l-(4-klorfenyl)-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 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 (bred) (1H) . <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-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

ble erholdt ved omsetning av 1-(4-klorfenyl)-6-hydroksy-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 100-104 °C. Temp. 100-104 °C.

Eksempel 39 Example 39

6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

ble erholdt ved omsetning av 1-(4-klorfenyl)-6-hydroksy-2-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 83-88 °C. Temp. 83-88 °C.

Eksempel 40 Example 40

6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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 t (J = 7,5 Hz, 2H); 3,94 t (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) . <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) .

Eksempel 41 Example 41

6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-l-ol 6-[[1-(4-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

ble erholdt ved omsetning av 6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. 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.

Smp. 115-120 °C. Temp. 115-120 °C.

Eksempel 42 Example 42

6-[[1-(2-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(2-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 5-klor-2-nitrofenyl-o-tolylamin a) 5-chloro-2-nitrophenyl-o-tolylamine

Til en oppløsning av 10 g l-klor-3,4-dinitrobenzen i To a solution of 10 g of l-chloro-3,4-dinitrobenzene i

50 ml etanol tilsatte man 81 ml o-toluidin og oppvarmet i 72 h inntil tilbakeløp. Man konsentrerte i vakuum og tok resten opp i etylacetat og 2 N vandig saltsyre. Den organiske fase ble ekstrahert enda tre ganger med 2 N vandig saltsyre, tørket over natriumsulfat og konsentrert i vakuum. Man renset resten ved hjelp av kromatografi på silikagel. 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 (CDCI3) : 5 = 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 (bred)(1H). <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-metoksy-2-nitrofenyl-o-tolylamin b) 5-methoxy-2-nitrophenyl-o-tolylamine

Til en oppløsning av 1 g natrium i 20 ml metanol To a solution of 1 g of sodium in 20 ml of methanol

tilsatte man 1 g 5-klor-2-nitrofenyl-o-tolylamin og oppvarmet i 72 h inntil tilbakeløp. Derpå ble avkjøling til 0 °C foretatt og det krystallinske produkt suget av. 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 (CDCI3) : 5 = 2,30 ppm s (3H); 3,72 s (3H); 6,19 d (J = <1>H-NMR (CDCl3) : δ = 2.30 ppm s (3H); 3.72 s (3H); 6.19 d (J =

2 Hz, 1H); 6,32 dd (J = 10, 2 Hz, 1H); 7,20-7,40 m (4H); 8,20 d (J = 10 Hz, 1H); 9,62 s (bred)(1H). c) 6-metoksy-l-(2-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 5-metoksy-2-nitrofenyl-o-tolylamin 1 henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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 (CDCI3) : 6 = 1,93 ppm s (3H) ; 3,78 s (3H) ; 6,42 d (J = <1>H-NMR (CDCl3) : δ = 1.93 ppm s (3H); 3.78 s (3H); 6.42 d (J =

2 Hz, 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-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-metoksy-l-(2-metylfenyl)-2-fenyl-lH-benzimidazol ble omsatt i henhold til den generelle arbeidsinstruks 6. Råproduktet ble omsatt med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. <1>H-NMR (CDCI3) : 6 = 1,43-1,58 ppm m (2H); 1, 62-1,84 m (4H); 1,93 s (3H); 2,34 t (J = 7,5 Hz, 2H); 3,68 s (3H); 3,90 t (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) : Eksempel 43 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-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre 6-[[1-(2-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble erholdt ved omsetning av 6-[[1-(2-metylfenyl)-2-fenyl-lH-benzimidazol-:6-yl] oksy] heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 198-200 °C. Temp. 198-200 °C.

Eksempel 44 Example 44

6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 5-klor-2-nitrofenyl-m-tolylamin a) 5-chloro-2-nitrophenyl-m-tolylamine

Til en oppløsning av 50 g l-klor-3,4-dinitrobenzen i To a solution of 50 g of l-chloro-3,4-dinitrobenzene i

250 ml etanol tilsatte man 81 ml m-toluidin og lot oppløsningen få henstå i 72 h. Reaksjonsblandingen ble filtrert og krystal-lisatet vasket med kald etanol og 2 N vandig saltsyre. Man renset ved hjelp av kromatografi på silikagel. 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 (CDC13) : 5 = 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 t (J = 10 Hz, 1H) ; 8,18 d (J = 10 Hz, 1H); 9,52 s (bred)(lH). <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-metoksy-2-nitrofenyl-m-tolylamin b) 5-methoxy-2-nitrophenyl-m-tolylamine

Til en oppløsning av 9 g natrium i 670 ml metanol To a solution of 9 g of sodium in 670 ml of methanol

tilsatte man 39 g 5-klor-2-nitrofenyl-m-tolylamin og oppvarmet i 72 h inntil tilbakeløp. Deretter ble avkjøling til 0 °C foretatt og det krystallinske produkt suget av. 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 (CDCI3) : 5 = 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 t (J = 10 Hz, 1H); 8,19 d (J = 10 Hz, 1H); 9,72 s (bred)(1H). <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-metoksy-l-(3-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 5-metoksy-2-nitrofenyl-m-tolylamin 1 henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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 (CDC13) : 5 = 2,42 ppm .s (3H) ; 3,81 s (3H) ; 6,69 d (J = <1>H-NMR (CDCl 3 ): δ = 2.42 ppm .s (3H); 3.81 s (3H); 6.69 d (J =

2 Hz, 1H); 7,03 dd (J - 8, 2 Hz, 1H); 7,10-7,18 m (2H); 7,30-7,48 m (5H); 7,62 dd (J = 8, 1 Hz, 2H) 7,89 d (J = 8 Hz, 1H) . d) 6-hydroksy-l-(3-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-l-(3-metylfenyl)-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 6. tø-NMR (D6-DMSO): 5 = 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 (bred)(lH); 7,32-7,55 m (7H), 7,59 d (J = 8 Hz, 1H); 9,37 s (bred) 1H). 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-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

ble erholdt ved omsetning av 6-hydroksy-l-(3-metylfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 (CDC13) : 5 = 1,44-1,58 ppm m (2H); 1, 64-1, 85 m (4H); 2,35 t (J = 7,5 Hz, 2H); 2,40 s (3H); 3,68 s (3H); 3,95 t (J = <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 (bred) (2H); 7,25-7, 43 m (4H); 7,55 dd (J = 8, 1 Hz, 2H); 7,77 d (J = 8 Hz, 1H). 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).

Eksempel 45 Example 45

6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane-acid isopropyl ester

ble erholdt ved omsetning av 6-hydroksy-l-(3-metylfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3) : 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 t (J = 7,5 Hz, 2H) ; 2,41 s (3H); 3,95 t (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 (bred)(lH); 7,25-7,41 m (4H); 7,54 dd (J = 8, 1 Hz, 2H); 7,75 d (J = 8 Hz, 1H). <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).

Eksempel 46 Example 46

6- [ [1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble erholdt ved omsetning av 6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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): 5 = 1,38-1,80 ppm m.(6H); 2,23 t (J = 7,5 Hz, 2H); 3,84-3,93 m (2H); 6,60 d (J = 2 Hz, 1H); 6,87 d (bred)(J = 8 Hz, 1H); 7,15 d (J = 8 Hz, 2H); 7,20-7,32 m (4H); 7,42-7,50 rn" 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). (2H); 7.59 d (J = 8 Hz, 1H); 7.77 d (J = 8 Hz, 1H).

Eksempel 47 Example 47

6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-l-ol 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

ble erholdt ved omsetning av 6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. 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 (CDCI3) : 6 = 1, 40-1,85 m (8H) ; 2,40 s (3H) ; 3,68 t (J = 7,5 Hz, 2H); 3,96 t (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 (bred)(lH); 7,25-7,42 m (5H); 7,54 dd (J = 8, 1 Hz, 2H); 7,76 d <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) . (J = 8 Hz, 1H).

Eksempel 48 Example 48

6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 5-klor-2-nitrofenyl-p-tolylamin a) 5-chloro-2-nitrophenyl-p-tolylamine

ble analogt med 5-klor-2-nitrofenyl-m-tolylamin fremstilt fra 1-klor-3,4-dinitrobenzen og p-toluidin. Man foretok rensing ved hjelp av krystallisasjon. 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 (CDCI3) : 5 = 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 = <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 =

10 Hz, 2H); 8,18 d (J = 10 Hz, 1H); 9,50 s (bred)(1H). 10Hz, 2H); 8.18 d (J = 10 Hz, 1H); 9.50s (wide)(1H).

b) 5-metoksy-2-nitrofenyl-p-tolylamin b) 5-methoxy-2-nitrophenyl-p-tolylamine

ble fremstilt analogt med 5-metoksy-2-nitrofenyl-m-tolylamin fra was prepared analogously with 5-methoxy-2-nitrophenyl-m-tolylamine from

5-klor-2-nitrofenyl-p-tolylamin og natriummetanolat. 5-chloro-2-nitrophenyl-p-tolylamine and sodium methanolate.

<X>H-NMR (CDCI3) : 6 = 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); 9,70 s (bred)(1H). <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-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 5-metoksy-2-nitrofenyl-p-tolylamin c) 6-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole was obtained by reacting 5-methoxy-2-nitrophenyl-p-tolylamine

i henhold til den generelle arbeidsinstruks 1 og med påfølgende in accordance with the general work instructions 1 and following

syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. cyclization with triethylorthobenzoate according to the general work instructions 3.

<1>H-NMR (CDC13) : 6 = 2,49 ppm s (3H) ; 3,80 s (3H) ; 6,69 d (J = <1>H-NMR (CDCl3) : δ = 2.49 ppm s (3H); 3.80 s (3H); 6.69 d (J =

2 Hz, 1H); 6,97 dd (J = 8, 2 Hz, 1H); 7,20 d (bred)(J = 8 Hz, 2H); 7,25-7,36 m (5H); 7,53 dd (J = 8, 1 Hz, 2H); 7,76 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). 8 Hz, 1H).

d) 6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol i henhold til den génerelle arbeidsinstruks 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 (bred)(1H). 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ble erholdt ved omsetning av 6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 1H-NMR (CDCI3) : 5 = 1, 44-1,58 ppm m (2H) ; 1, 62-1, 86 m (4H) ; 2,34 t (J = 7,5 Hz, 2H); 2,48 s (3H); 3,68 s (3H); 3,94 t (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); 7,28-7,38 m (5H); 7,55 dd (J = 8, 1 Hz, 2H); 7,75 d (J = 8 Hz, 1H). Eksempel 49 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropyles ter ble erholdt ved omsetning av 6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. <X>H-NMR (CDCI3) : 5 = 1,22 ppm d (J = 7,5 Hz, 6H); 1,44-1,56 m (2H); 1,62-1,85 m (4H); 2,30 t (J = 7,5 Hz, 2H); 2,47 s (3H); 3,93 t (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) . 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) .

Eksempel 50 Example 50

6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyre 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

ble erholdt ved omsetning av 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 186-190 °C. Temp. 186-190 °C.

Eksempel 51 Example 51

6- [ [1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-1-ol 6- [ [1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexan-1-ol

ble erholdt ved omsetning av 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. 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.

^-NMR (CDC13) : 5 = 1,38-1, 80 m (8H); 2,47 s (3H) ; 3,65 t (J = 7,5 Hz, 2H); 3,93 t (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). 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).

Eksempel 52 Example 52

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

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

3 g 3-fluor-4-nitrofenol og 6,9 g 3,4-dimetylanilin ble 3 g of 3-fluoro-4-nitrophenol and 6.9 g of 3,4-dimethylaniline were

blandet med hverandre og omrørt i 2 h ved 150 °C. Etter avkjøling ble blandingen oppløst i diklormetan og ekstrahert seks ganger med 1 N vandig saltsyre. Den organiske fase ble kastet, og de kombinerte, vandige faser ble ekstrahert tre ganger med kloroform. De kombinerte ekstrakter ble tørket over natriumsulfat og konsentrert i vakuum, og resten ble kromatografert på silikagel. <1>H-NMR (CDC13/D6-DMS0) : 5 = 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 = 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 =

8 Hz, 1H); 7,93 d (J = 8 Hz, 1H); 9,50 s (bred)(lH). 8Hz, 1H); 7.93 d (J = 8 Hz, 1H); 9.50 s (wide)(lH).

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

ble erholdt ved omsetning av 3-(3,4-dimetylfenyl)amino-4-nitro-fenol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3) : 5 = 1,38-1,52 ppm m (2H); 1,59-1,80 m (4H); 2,30 s (6H); 2,33 t (J = 7,5 Hz, 2H); 3,68 s (3H); 3,87 t (J = <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 (bred)(1H); 7,18 d (J = 8 Hz, 1H); 8,17 d (J = 8 Hz, 1H); 9,71 s (bred)(1H). 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-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetyles ter 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

ble erholdt ved omsetning av 6-[3-(3,4-dimetylfenyl)amino-4-nitrofenyl]oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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 (CDCI3) : 5 = 1, 44-1,56 ppm m (2H) ; 1, 62-1, 84 m (4H); 2,30 s (3H); 2,33 t (J = 7,5 Hz, 2H); 2,34 s (3H); 3,68 s (3H); 3,93 t (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 (bred)(lH); 7,22-7,35 m (4H); 7,57 dd (J = 8, 1,5 Hz, 2H); 7,76 d (J = 8 Hz, 1H). <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).

Eksempel 53 Example 53

6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyre 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

ble erholdt ved omsetning av 6-[[1-(3, 4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 158-161 °C. Temp. 158-161 °C.

Eksempel 54 Example 54

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

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

5,4 g 3-fluor-4-nitrofenol og 4,3 ml 3,5-dimetylanilin 5.4 g of 3-fluoro-4-nitrophenol and 4.3 ml of 3,5-dimethylaniline

ble blandet med hverandre og omrørt ved 120 °C i 6 h. Etter avkjøling ble blandingen tatt opp i etylacetat og vann og ekstrahert tre ganger med 1 N vandig saltsyre. De kombinerte, vandige faser ble ekstrahert tre ganger med etylacetat. De kombinerte, organiske faser ble tørket over natriumsulfat og konsentrert i vakuum, og resten ble krystallisert. 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) :• 5 = 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) ; 6,90 s (bred)(1H); 6,98 s (bred)(2H); 8,04 d (J = 8 Hz, 1H); 9,51 s (bred)(1H). 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-dimetylfenyl)amino-4-nitrofenyl]oksyheksansyre-metylester b) 6-[3-(3,5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

ble erholdt ved omsetning av 3-(3,5-dimetylfenyl)amino-4-nitro-fenol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3) : 5 = 1, 40-1,52 ppm m (2H); 1, 60-1, 80 m (4H); 2,30 t (J = J,5Hz,.. 2H) ;. 2,32 s J6H) ;■ 3,68 s (3H) ; 3,88 t (J <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 (bred)dH); 6,91 s (bred) (2H) ; 8,17 d (J = 8 Hz, 1H) ; 9,69 s (bred)(1H). 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-dimetylfenyl)amino-4-nitrofenyl]oksyheksansyremetyl-ester 6-[3-(3,5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

ble erholdt ved omsetning av 6-[3-(3,5-dimetylfenyl)amino-4-nitrofenyl]oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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.

Smp. 124-126 °C. Temp. 124-126 °C.

Eksempel 55 Example 55

6-[[1-(3,5-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyre 6-[[1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

ble erholdt ved omsetning av 6-[3-(3, 5-dimetylfenyl)amino-4-nitrofenyl]oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 9. was obtained by reacting 6-[3-(3, 5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to the general work instructions 9.

Smp. 162-164 °C. , Temp. 162-164 °C. ,

Eksempel 56 Example 56

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

ble erholdt ved omsetning av 6-[3-(3,5-dimetylfenyl)amino-4-nitrofenyl]oksyheksansyre med isopropanol i henhold til den generelle arbeidsinstruks 10. was obtained by reacting 6-[3-(3,5-dimethylphenyl)amino-4-nitrophenyl]oxyhexanoic acid with isopropanol according to the general work instructions 10.

Smp. 98-101 °C. Temp. 98-101 °C.

Eksempel 57 Example 57

6-[[1-(3-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(3-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

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

4 g 3-fluor-4-nitrofenol og 9,4 g m-anisidin ble 4 g of 3-fluoro-4-nitrophenol and 9.4 g of m-anisidine were

blandet med hverandre og omrørt ved 150 °C i 2,5 h. Etter avkjøl-ing ble blandingen oppløst i diklormetan og ekstrahert tre ganger med 1 N vandig saltsyre. Den organiske fase ble tørket over natriumsulfat og konsentrert i vakuum, og resten ble kroma-tograf ert på silikagel. 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 (CDC13) : 6 = 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 (bred)(J = 10 Hz, 1H); 7,32 t (J = 10 Hz, 1H); 8,19 d (J = 10 Hz, 1H); 9,68 s (bred)(lH); 9,69 s (bred). <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-metoksyfenyl)amino-4-nitrofenyl]oksyheksansyremetyl-ester b) 6-[3-(3-Methoxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

ble erholdt ved omsetning av 3-(3-metoksyfenyl)amino-4-nitro-fenol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3) : 5 = 1,42-1,58 ppm m (2H); 1, 60-1, 93 m (4H); 2,34 <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 t (J = 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 (bred)(J = 8 Hz, 1H); 7,32 t (J = 8 Hz, 1H); 8,19 d (J = 10 Hz, 1H); 9,70 s (bred)(lH). 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-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(3-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

ble erholdt ved omsetning av 6-[3-(3-metoksyfenyl)amino-4-nitrofenyl]oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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.

Hl-NMR (CDCI3) : 8 = 1, 44-1,58 ppm m (2H) ; 1, 62-1,86 m (4H) ; 2,34 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 t (J = 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 t (J = 8 Hz, 1H); 7,56 dd (J = 8, .2 Hz, 2H) ; 7,74 d (J = 8 Hz, 1H) . 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) .

Eksempel 58 Example 58

6-[[1-(3-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyre 6-[[1-(3-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

ble erholdt ved omsetning av 6-[[1-(3-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 14 9-152 °C. Temp. 14 9-152 °C.

Eksempel 59 Example 59

6-[[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetyles ter 6-[[1-(4-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

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

0,16 g 3-fluor-4-nitrofenol og 0,37 g p-anisidin ble 0.16 g of 3-fluoro-4-nitrophenol and 0.37 g of p-anisidine were

blandet med hverandre og omrørt ved 150 °C i 1,5 h. Etter avkjøl-ing ble blandingen oppløst i diklormetan og ekstrahert to ganger, med 1 N vandig saltsyre og én gang med mettet natriumkloridopp-løsning. Den organiske fase ble tørket over natriumsulfat og konsentrert i vakuum. 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 (CDC13/D6-DMS0) : 6 = 3,57 ppm s (3H) ; 6,06 dd (J = 10, <1>H-NMR (CDCl3/D6-DMSO): δ = 3.57 ppm s (3H); 6.06 dd (J = 10,

2 Hz, 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 (bred) (1H) ; 9,80 s (bred) . b) 6-[3-(4-metoksyfenyl)amino-4-nitrofenyl]oksyheksansyremetyl-ester ble erholdt ved omsetning av 3-(4-metoksyfenyl)amino-4-nitro-fenol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. <1>H-NMR (CDCI3) : 5 = 1,38-1,50 ppm m (2H) ; 1,60-1, 80 m (4H) ; 2,33 t (J = 7,5 Hz, 2H); 3,67 s (3H); 3,85 t (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 (bred)(1H). 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-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(4-Methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

ble erholdt ved omsetning av 6-[3-(4-metoksyfenyl)amino-4-nitrq-fenyl]oksyheksansyremetylester i henhold til den generelle was obtained by reacting 6-[3-(4-methoxyphenyl)amino-4-nitrq-phenyl]oxyhexanoic acid methyl ester according to the general

arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. work instructions 1 and with subsequent cyclization with triethylorthobenzoate according to general work instructions 3.

Smp. 98-102 °C. Temp. 98-102 °C.

Eksempel 60 Example 60

6-[[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre 6-[[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble erholdt ved omsetning av 6-[[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 160-165 °C. Temp. 160-165 °C.

Eksempel 61 Example 61

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

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

3 g 3-fluor-4-nitrofenol og 8,8 g 3,4-dimetoksyanilin 3 g of 3-fluoro-4-nitrophenol and 8.8 g of 3,4-dimethoxyaniline

ble blandet med hverandre og omrørt ved 150 °C i 2 h. Etter avkjøling ble-blandingen oppløst i diklormetan og ekstrahert to ganger med 1 N vandig saltsyre. Den vandige fase ble ekstrahert to ganger med kloroform, og de kombinerte kloroformekstrakter ble tørket over natriumsulfat og konsentrert i vakuum. 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): 5 = 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 (bred)(1H); 10,72 s (bred). <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-dimetoksyfenyl)amino-4-nitrofenyl]oksyheksansyre-metylester b) 6-[3-(3,4-dimethoxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester

ble erholdt ved omsetning av 3-(3,4-dimetoksyfenyl)amino-4-nitrofenol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3) : 5 = 1, 40-1,52 ppm m (2H) ; 1, 60-1, 80 m (4H) ; 2,32 t (J = 7,5 Hz, 2H); 3,68 s (3H); 3,85 t (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 (bred)(1H). 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-dimetoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester 6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

ble erholdt ved omsetning av 6-[3-(3,4-dimetoksyfenyl)amino-4-nitrofenyl]oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. 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.

Smp. 116-118 °C. Temp. 116-118 °C.

Eksempel 62 Example 62

6-[[1-(3,4-dimetoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyre 6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid

ble erholdt ved omsetning av 6-[[1-(3,4-dimetoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 158-161 °C. Temp. 158-161 °C.

Eksempel 63 Example 63

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

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

0,86 g 3-fluor-4-nitrofenol og 2,25 g 3,4-metylen-dioksyanilin ble blandet med hverandre og omrørt ved 120 °C i 5 h. Råblandingen ble kromatografert på silikagel. 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): 5 = 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 (bred)(1H). <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-metylendioksyfenyl)amino-4-nitrofenyl]oksyheksan-syremetyles ter b) 6-[3-(3,4-methylenedioxyphenyl)amino-4-nitrophenyl]oxyhexane acid methyl ester

ble erholdt ved omsetning av 3-(3,4-metylendioksyfenyl)amino-4-nitrofenol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. was obtained by reacting 3-(3,4-methylenedioxyphenyl)amino-4-nitrophenol with 6-bromohexanoic acid methyl ester according to the general work instructions 8.

Smp. 108-111 °C. Temp. 108-111 °C.

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

ble erholdt ved omsetning av 6-[3-(3,4-metylendioksyfenyl)amino-4-nitrofenyl]oksyheksansyremetylester i henhold til den gener- was obtained by reaction of 6-[3-(3,4-methylenedioxyphenyl)amino-4-nitrophenyl]oxyhexanoic acid methyl ester according to the gen-

elle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. <1>H-NMR (CDCI3) : 5 = 1,43-1,55 ppm m (2H) ; 1, 65-1, 82 m (4H) ; 2,35 t (j =7,5 Hz, 2H); 3,68 s (3H); 3,95 t (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). 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).

Eksempel 64 Example 64

6-[[l-[3,4 - (metylendioksy)fenyl]-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyre 6-[[1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]-oxy]hexanoic acid

ble erholdt ved omsetning av 6-[[1-(3,4-metylendioksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. 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.

Smp. 130 °C. Temp. 130 °C.

Eksempel 65 Example 65

6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyremetylester 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester

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

3,7 g 3-fluor-4-nitrofenol og 4,76 g 3,4,5-trimetoksy-anilin ble blandet med hverandre og omrørt ved 100 °C i 10 h. Etter avkjøling ble blandingen tatt opp i etylacetat og vann og ekstrahert tre ganger med etylacetat. De kombinerte, organiske faser ble ekstrahert tre ganger med 1 N vandig saltsyre og én gang med mettet natriumkloridoppløsning, tørket over natriumsulfat og så langt som mulig konsentrert i vakuum. Produktet ble utlutet med diisopropyleter. 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.

<l>H-NMR (De-DMSO): 5 = 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); 9,50 s (bred)(lH); 10,71 s (bred). <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-trimetoksyfenyl) amino]fenyl]oksyheksan-syremetylester b) 6-[4-nitro-3-[(3,4,5-trimethoxyphenyl)amino]phenyl]oxyhexane acid methyl ester

ble erholdt ved omsetning av 4-nitro-3-[(3,4,5-trimetoksyfenyl)-amino]fenol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 (CDCI3) : 6 = 1, 40-1,53 ppm m (2H) ; 1, 60-1,82 m (4H) ; 2,32 <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 (bred) (1H).. ;6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;ble erholdt ved omsetning av 6-[4-nitro-3-[(3,4,5-trimetoksy-fenyl) amino]fenyl]oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. ;Smp. 128-130 °C. ;Eksempel 66 ;6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyre ;ble erholdt ved omsetning av 6-[[2-fenyl-l-(3,4,5-trimetoksy-fenyl) -lH-benzimidazol-6-yl] oksy] heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 198-201 °C. ;Eksempel 67 ;6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester ;ble erholdt ved omsetning av 6-[[2-fenyl-1-(3,4,5-trimetoksy-fenyl) -lH-benzimidazol-6-yl] oksy] heksansyre med isopropanol i henhold til den generelle arbeidsinstruks 10. ;Smp. 98-101 °C. ;Eksempel 68 ;6-[[1-[4-(N,N-dimetylamino)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester ;a) N,N-dimetyl-N'-(5-klor-2-nitrofenyl)benzen-1,4-diamin ble fremstilt analogt med 5-klor-2-nitrofenyl-m-tolylamin fra 1-klor-3,4-dinitrobenzen og N,N-dimetyl-p-fenylendiamin. ^-NMR (CDC13) : 6 = 3,01 ppm s (6H); 6,63 dd (J = 10, 2 Hz, 1H) ; 6,80 d (bred)(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 (bred) (1H) . b) N,N-dimetyl-N1 - <5-metoksy-2-nitrofenyl)benzen-1,4-diamin 24,9 g N,N-dimetyl-N'-(5-klor-2-nitrofenyl)benzen-1, 4-diamin ble tilsatt til en oppløsning av 8 g natrium i 200 ml metanol og blandingen oppvarmet til 120 °C i 9 h i en autoklav. Etter avkjøling ble det foretatt avsugning fra det krystallinske produkt. <1>H-NMR (CDC13) : 5 = 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); 9,67 s (bred)(1H). c) 6-metoksy-l- [4- (N,N-dimetylamino) fenyl] -2-fenyl-lH-benzimidazol ble fremstilt ved omsetning av N,N-dimetyl-N'-(5-metoksy-2-nitrofenyl)benzen-1,4-diamin i henhold til den generelle arbeidsinstruks 1, påfølgende omsetning av rådiaminet med trimetylortobenzoat i henhold til den generelle arbeidsinstruks 3 og påfølgende oppvarming av råproduktet med 6 N vandig saltsyre i 1 h inntil tilbakeløp. Etter alkalisering av reaksjonsblandingen med vandig natriumhydroksid ble det ekstrahert med etylacetat, tørket over natriumsulfat og konsentrert i vakuum. <1>H-NMR (CDCI3) : 5 = 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-hydroksy-l-[4-(N,N-dimetylamino)fenyl]-2-fenyl-lH-benzimidazol ;ble erholdt ved omsetning av 6-metoksy-l-[4-(N,N-dimetylamino)-fenyl]-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 6. ;<1>H-NMR (De-DMSO): 5 = 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 (bred)(1H). ;6- [ [1- [4- (N,N-dimetylamino) fenyl] -2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester ;ble erholdt ved omsetning av 6-hydroksy-l-[4-(N,N-dimetylamino)-fenyl]-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;<1>H-NMR (CDC13) : 6 = 1,43-1,57 ppm m (2H); 1, 64-1, 85 m (4H); 2,33 t (J = 7,5 Hz, 2H); 3,05 s (6H); 3,67 s (3H); 3,93 t (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). ;Eksempel 69 ;6-[[1-[4- (N,N-dimetylamino)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ;ble erholdt ved omsetning av 6-[[1-[4-(N,N-dimetylamino)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 210-213 °C. ;Eksempel 70 ;6-[[1-(4-bifenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ;a) 5-klor-2-nitrofeny1-4-bifenylamin ;ble analogt med 5-klor-2-nitrofenyl-m-tolylamin fremstilt fra 1-klor-3,4-dinitrobenzen og 4-bifenylamin. Man renset ved hjelp av kromatografi på silikagel. ;<1>H-NMR (CDCI3) : 5 = 6,76 dd (J = 10, 2 Hz, 1H); 7,26 d (J = 2 Hz, 1H); 7,35 d (J = 8 Hz, 1H); 7,32-7,52 m (4H); 7,60-7,72 m (4H); 8,19 d (J = 10 Hz, 1H); 9,60 s (bred)(1H). ;b) 5-metoksy-2-nitrofenyl-4-bifenylamin ;ble analogt med 5-metoksy-2-nitrofenyl-m-tolylamin fremstilt fra ;5-klor-2-nitrofenyl-4-bifenylamin og natriummetanolat. ;Smp. 150-154 °C. ;b) 1-(4-bifenyl)-6-metoksy-2-fenyl-lH-benzimidazol ble erholdt ved. omsetning av 5-metoksy-2-nitrofenyl-4-bifenylamin i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. Smp. 140-144 °C. c) 1-(4-bifenyl)-6-hydroksy-2-fenyl-lH-benzimidazol ble erholdt ved omsetning av 1-(4-bifenyl)-6-metoksy-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 6. ;Smp. 312 °C. ;6-[[1-(4-bifenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ;ble erholdt ved omsetning av 1-(4-bifenyl)-6-hydroksy-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 106-108 °C. ;Eksempel 71 ;6-[[1-(4-bifenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[1-(4-bifenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;<1>H-NMR (D6-DMSO): 6 = 1,35-1,78 ppm m (6H); 2,20 t (J = 7,5 Hz, 2H); 3,96 m (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) . ;Eksempel 72 ;6-[[1-(2-naftyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ;a) 3-(2-naftylamino)-4-nitrofenol ;3 g 3-fluor-4-nitrofenol og 8,2 g 2-naftylamin ble ;blandet med hverandre og' omrørt ved 180 °C i 8 h. Råblandingen ble tatt opp i kloroform og vasket med 2 N vandig saltsyre. Den organiske fase ble tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. ;<1>H-NMR (D6-DMSO) : 5 = 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 (bred) (1H). , ;b) 6-[3-(2-naftyl)amino-4-nitrofenyl]oksyheksansyremetylester ble erholdt ved omsetning av 3-(2-naftylamino)-4-nitrofenol med ;6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;<1>H-NMR (CDC13) : 5 = 1,35-1,49 ppm m (2H) ; 1, 60-1,80 m (4H) ; 2,30 t (J = 7,5 Hz, 2H); 3,64 s (3H); 3,84 t (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 (bred)(1H). ;6-[[1-(2-naftyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ;ble erholdt ved omsetning av 6-[3-(2-naftylamino)-4-nitrofenyl]-oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. ;Smp. 111-114 °C. ;Eksempel 73 ;6-[[1-(2-naftyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[1-(2-naftyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 170-175 °C. ;Eksempel 74 ;6-[[1-(2-fluorenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;a) 3-(2-fluorenylamino)-4-nitrofenol ;2,17 g 3-fluor-4-nitrofenol og 5 g 2-aminofluoren ble ;blandet med hverandre og omrørt ved 140 °C i 9 h. Råblandingen ble tatt opp i etylacetat og vann og vasket med 1 N vandig saltsyre. Den vandige fase ble ekstrahert med etylacetat, og de kombinerte, organiske faser ble vasket tre ganger med 2 N vandig saltsyre og én gang med mettet natriumkloridoppløsning, tørket over natriumsulfat og vakuum. Resten ble kromatografert på silikagel. ;<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); 7,57 s (bred)(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 (bred)(1H). ;b) 6-[3-(2-fluorenylamino)-4-nitrofenyl]oksyheksansyremetylester ble erholdt ved omsetning av 3-(2-fluorenylamino)-4-nitrofenol ;med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;<1>H-NMR (CDCI3) : 6 = 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 t (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 t (J = 8 Hz, 2H); 7,42 t (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 (bred) (1H) . ;6-[ [1-(2-fluorenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;ble erholdt ved omsetning av 6-[3-(2-f luorenylamino).-4-nitrofenyl]oksyheksansyremetylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende syklisering med trietylortobenzoat i henhold til den generelle arbeidsinstruks 3. ;Smp. 125-128 °C. ;Eksempel 75 ;6-[[l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;a) Etyl-(3-trifluormetyl)benzimidathydroklorid ;9,7 ml 3-(trifluormetyl)benzonitril ble oppløst i 12 ml ;etanol og oppløsningen mettet med HCl-gass under avkjøling i isbad. Etter 72 h ble det foretatt avsugning fra det utfelte produkt. Produktet ble vasket med dietyleter. ;Smp. 131-133 °C (dekomp.). ;b) 5-metoksy-2-nitrofenyldifenylamin ;En oppløsning av 2 g 3-fluor-4-nitroanisol i 16 ml ;anilin ble omrørt ved 140 °C i 24 h. Etter avkjøling tok man opp i etylacetat og ekstraherte med 2 N vandig saltsyre. Den organ- ;iske fase ble tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. ;<X>H-NMR (CDCI3) : 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); 9,78 s (bred)(1H). ;c) 4-metoksy-N<2->fenyl-o-fenylendiamin ;ble erholdt ved omsetning av 5-metoksy-2-nitrofenyldifenylamin i ;henhold til den generelle arbeidsinstruks 1. ;<X>H-NMR (CDCI3) : 5 = 3,42 ppm s (bred) (2H); 3,72 s (3H); 5,33 s (bred)(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-metoksy-l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol ble erholdt ved omsetning av 4-metoksy-N<2->fenyl-o-fenylendiamin ;med etyl-(3-trifluormetyl)benzimidathydroklorid i henhold til den generelle arbeidsinstruks 4. ;Smp. 138-140 ?C. e) 6-hydroksy-l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-l-fenyl-2-[3-(trifluor-metyl) f enyl] -lH-benzimidazol i henhold til den generelle arbeidsinstruks 7. ;<X>H-NMR (D6-DMSO) : 5 = 6,60 ppm d (J = 2 Hz, 1H) ; 6,99 dd (J = 10, 2 Hz, 1H); 7,50-7,89 m (10H). ;6-[[l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;ble erholdt ved omsetning av 6-hydroksy-l-fenyl-2-[3-(trifluor-metyl) fenyl] -lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 68-70 °C. ;Eksempel 76 ;6-[[l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester ;ble erholdt ved omsetning av 6-hydroksy-l-fenyl-2-[3-(trifluor-metyl) f enyl] -lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 96-98 °C. ;Eksempel 77 ;6-[[l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyre ;ble erholdt ved omsetning av 6-[[1-fenyl-2-[3-(trifluormetyl)-fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;<1>H-NMR (D6-DMSO): 5 = 1,38-1,80 ppm m (6H); 2,27 t (J = 7,5 Hz, 2H); 3,98 t (J = 7,5 Hz, 2H); 6,70 d (J = 2 Hz, 1H); 7,02 dd (J = 10, 2 Hz, 1H); 7,48-7,88 m (9H); 7,77 d (J = 10 Hz, 1H); 11,94 s (bred)(1H). ;Eksempel 78 ;6-[[l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksan-l-ol ;ble erholdt ved omsetning av 6-[[l-fenyl-2-[3-(trifluormetyl)-fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 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 t (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 (bred)(J = 8 Hz, 1H); 7,78 d (J = 10 Hz, 1H); 7,83 s (bred)(1H). ;Eksempel 79 ;6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;a) 2-(3-klorfenyl)-6-metoksy-l-fenyl-lH-benzimidazol ble erholdt ved omsetning av 4-metoksy-N<2->fenyl-o-fenylendiamin ;med etyl-3-klorbenzimidathydroklorid (fremstilt i henhold til: DeWolfe og Augustine; J. Org. Chem.; 30; 699) i henhold til den generelle arbeidsinstruks 4. ;Smp. 149-151 °C. b) 2-(3-klorfenyl)-6-hydroksy-l-fenyl-lH-benzimidazol ble erholdt ved omsetning av 2-(3-klorfenyl)-6-metoksy-l-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 7. Smp. 199-202 °C. ;6-[[2-(3-klorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;ble erholdt ved omsetning av 2-(3-klorfenyl)-6-hydroksy-l-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 69-72 °C. ;Eksempel 80 ;6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester ;ble erholdt ved omsetning av 2-(3-klorfenyl)-6-hydroksy-l-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 98-100 °C. ;Eksempel 81 ;6-[[2-(3-klorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 137-140 °C. ;Eksempel 82 ;6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-1-ol ;ble erholdt ved omsetning av 6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. ;<1>H-NMR (CDC13) : 5 = 1,40-1,70 ppm m (6H); 1,75-1, 86 m (2H) ; 3,67 t (J = 7,5 Hz, 2H); 3,93 t (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) ;Eksempel 83 ;6-[[2-(4-klorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;a) Etyl-4-klorbenzimidathydroklorid ;10 g 4-klorbenzonitril ble suspendert i 12 ml etanol og ;oppløst ved tilsetning av dietyleter. Under avkjøling i isbad ble metning med HCl-gass foretatt. Etter 72 h ble det foretatt avsugnijig fra det utfelte produkt. Produktet ble vasket med dietyleter. ;Smp. 173-174 °C (dekomp.). ;a) 2-(4-klorfenyl)-6-metoksy-l-fenyl-lH-benzimidazol ble erholdt ved omsetning av 4-metoksy-N<2->fenyl-o-fenylendiamin ;med etyl-4-klorbenzimidathydroklorid i henhold til den generelle arbeidsinstruks 4. ;Smp. 162-164 °C. b) 2-(4-klorfenyl)-6-hydroksy-l-fenyl-lH-benzimidazol ble erholdt ved omsetning av 2-(4-klorfenyl)-6-metoksy-l-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 7. Smp. 24 6-250 °C. ;6-[[2-(4-klorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;ble erholdt ved omsetning av 2-(4-klorfenyl)-6-hydroksy-l-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 8 6-87 °C. ;Eksempel 84 ;6-t[2-(4-klorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester ;ble erholdt ved omsetning av 2-(4-klorfenyl)-6-hydroksy-l-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 124-126 °C.. ;Eksempel 85 ;6-[[2-(4-klorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[2-(4-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 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 t (J = 7,5 Hz, 2H) ; 3,91 t (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). ;Eksempel 86 ;6-[[2-(4-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-1-ol ;ble erholdt ved omsetning av 6-[[2-(4-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. ;<1>H-NMR (CDC13) : 5 = 1,38-1, 68 ppm m (6H); 1,74-1,85 m (2H); 3,67 ;t (bred) (J = 7,5 Hz, 2H) ; 3,94 t (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). ;Eksempel 87 ;6-[[2-(3-metylfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;a) 6-metoksy-2-(3-metylfenyl)-1-fenyl-lH-benzimidazol ble erholdt ved omsetning av 4-metoksy-N<2->fenyl-o-fenylendiamin ;med etyl-3-metylbenzimidathydroklorid (fremstilt i henhold til: DeWolfe og Augustine; J. Org. Chem.; 30; 699) i henhold til den generelle arbeidsinstruks 4. ;Smp. 156-158 °C. b) 6-hydroksy-2-(3-metylfenyl)-1-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-2-(3-metylfenyl)-1-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 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 (bred)(3H); 7,35-7,52 m (3H); 7,50-7-, 63 m (4H); 9,28 s (bred) (1H) . ;6-[[2-(3-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ble erholdt ved omsetning av 6-hydroksy-2-(3-metylfenyl)"-l-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 82-84 °C. ;Eksempel 88 ;6-[[2-(3-metylfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester ;ble erholdt ved omsetning av 6-hydroksy-2-(3-metylfenyl)-1-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;<X>H-NMR (CDC13) : 5 = 1,22 ppm d (J = 7,5 Hz, 6H) ; 1,38-1,56 m (2H); 1,62-1,85 m (4H); 2,30 t (J = 7,5 Hz, 2H); 2,30 s (3H); 3,93 t (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 (bred)(3H); 7,31 dd (J = 8, 2 Hz, 2H); 7,42-7,57 m (4H); 7,76 d (J = 10 Hz, 1H). ;Eksempel 89 ;6-[[2-(3-metylfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre ;ble erholdt ved omsetning av 6-[[2-(3-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;<1>H-NMR (D6-DMS0): 5 = 1,35-1,49 ppm m (2H); 1,50-1,63 m (2H) ; 1,64-1,78 m (2H); 2,22 t (J = 7,5 Hz, 2H); 2,24 s (3H); 3,92 t (J = 7,5 Hz, 2H); 6,62 d (J = 2 Hz, 1H); 6,95 dd (J = 10, 2 Hz, 1H); 7,18 s (bred)(3H); 7,37-7,42 m (3H); 7,51-7,65 m (3H); 7,67 d (J = 10 Hz, 1H); 11,90 s (bred)(1H). ;Eksempel 90 ;6-[[2-(3-metylfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-l-61 ;ble erholdt ved omsetning av 6-[[2-(3-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 92-94 °C. ;Eksempel 91 ;6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;a) 6-metoksy-2-(4-metylfenyl)-1-fenyl-lH-benzimidazol ble erholdt ved omsetning av 4-metoksy-N<2->fenyl-o-fenylendiamin ;med etyl-4-metylbenzimidathydroklorid (fremstilt i henhold til: DeWolfe og Augustine; J. Org. Chem.; 30; 699) i henhold til den generelle arbeidsinstruks 4. ;Smp. 150-152 °C. b) 6-hydroksy-2-(4-metylfenyl)-1-fenyl-lH-benzimidazol ble erholdt ved omsetning av 6-metoksy-2-(4-metylfenyl)-1-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 7. Smp. 257-264 °C. ;6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;ble erholdt ved omsetning av 6-hydroksy-2-(4-metylfenyl)-1-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 99-102 °C. ;Eksempel 92 ;6-[[2-(4-metylfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester ;ble erholdt ved ^msetning av 6-hydroksy-2-(4-metylfenyl)-1-fenyl-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 107-109 °C. ;Eksempel 93 ;6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre ;ble erholdt ved omsetning av 6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;1H-NMR (D6-DMSO): 5 = 1,33-1,49 ppm m (2H); 1,50-1,62 m (2H); 1,64-1,77 m (2H); 2,22 t (J = 7,5 Hz, 2H-) ; 2,30 s (3H) ; 3,90 t (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). ;Eksempel 94 ;6-[[2-(4-metylfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-l-ol ;ble erholdt ved omsetning av 6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 11. ;Smp. 150-152 °C. ;Eksempel 95 ;6-[[l-fenyl-2-(4-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;a) 6-metoksy-l-fenyl-2-(4-pyridinyl)-lH-benzimidazol ;0,4 g 4-metoksy-N<2>.-fenyl-o-fenylendiamin ble oppløst i ;8 ml N,N-dimetylformamid, og oppløsningen ble forsynt med 0,7 g etyl-2-etoksy-l,2-dihydrokinolin-l-karboksylat og 0,34 g iso-nikotinsyre. Man omrørte i 16 h ved 100 °C, tilsatte vann etter avkjølingen, ekstraherte tre ganger med etylacetat, vasket de kombinerte, organiske faser med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrerte i vakuum. Etter kroma-tografisk rensing på silikagel tok man amidet opp i 5 ml 6 N vandig saltsyre og oppvarmet i 3 h inntil tilbakeløp. Etter avkjøling omrørte man i mettet natriumbikarbonatoppløsning, ekstraherte tre ganger med etylacetat, vasket de kombinerte ekstrakter med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrerte i vakuum. <1>H-NMR (CDC13) : 5 = 3,80 ppm s (3H) ; 6,66 ppm d (J = 2 Hz, 1H) ; 7,02 dd (J = 10, 2 Hz, 1H); 7,32-7,38 m (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 (bred)(J = 6 Hz, 2H). b) 6-hydroksy-l-fenyl-2-(4-pyridinyl)-lH-benzimidazol ble fremstilt ved omsetning av 6-metoksy-l-fenyl-2-(4-pyridinyl)-1H-benzimidazol i henhold til den generelle arbeidsnstruks 7. <1>H-NMR (CD3OD): 5 = 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) ; 7., 4 9-7,57 m (4H); 8,40 d (bred)(J = 6 Hz, 2H). ;6-[[l-fenyl-2-(4-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksan-syrernetyles ter ;ble fremstilt ved omsetning av 6-hydroksy-l-fenyl-2-(4-pyri-dinyl) -lH-benzimidazol i henhold til den generelle arbeidsinstruks 8. ;Smp. 100-103 °C. ;Eksempel 96 ;6-[[l-fenyl-2-(4-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksansyre ble fremstilt ved omsetning av 6-[[1-fenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 160-162 °C. ;Eksempel 97 ;6-[(1,2-difenyl-5-nitro-lH-benzimidazol-6-yl)oksy]heksansyre-metylester ;a) 1,2-difenyl-6-hydroksy-5-nitro-lH-benzimidazol ;b) 1,2-difenyl-6-hydroksy-7-nitro-lH-benzimidazol ;c) 1,2-difenyl-6-hydroksy-5,7-dinitro-lH-benzimidazol ;5 g 1,2-difenyl-6-hydroksy-lH-benzimidazol ble oppløst ;i 45 ml iseddik og forsynt dråpevis ved 10-15 °C med en oppløs-ning av 1,67 g kaliumnitritt i 15 ml vann. Man holdt oppløs-ningen 2 h i isbad og deretter ved 20 °C i 2 h under omrøring, konsentrerte reaksjonsblandingen i vakuum og renset ved hjelp av kromatografi på silikagel. ;a) <X>H-NMR (CDCI3) : 5 = 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): 5 = 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): 5 = 7,32-7,58 ppm m (10H); 8,67 s (1H). ;6-[(1,2-difenyl-5-nitro-lH-benzimidazol-6-yl)oksy]heksansyre-metylester ;ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-5-nitro-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 123 °C. ;Eksempel 98 6-[(1,2-dif enyl-5.-nitro-lH-benzimidazol-6-yl)oksy]heksansyre-isopropylester ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-5-nitro-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 115-117 °C. ;Eksempel 99 ;6-[(1,2-difenyl-7-nitro-lH-benzimidazol-6-yl)oksy]heksansyre-metylester ;ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-7-nitro-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 110-112 °C. ;Eksempel 100 ;6-[(1,2-difenyl-7-nitro-lH-benzimidazol-6-yl)oksy]heksansyre-isopropyles ter ;ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-5-nitro-lH-benzimidazol med 6-brpmheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 88 °C. ;Eksempel 101 ;6-[(7-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyre-metylester ;340 mg 6-[(1,2-difenyl-7-nitro-lH-benzimidazol-6-yl)oksy]heksansyremetylester ble hydrert i etanol med Raney-nikkel i en autoklav ved' 50 °C og ved normalt trykk. Etter avsluttet hydrogenopptak ble det foretatt frafiltrering fra katalysatoren og konsentrering i vakuum. ;Smp. 113-115 °C. ;Eksempel 102 ;6-[(7-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyre-isopropylester ;fikk man analogt med den i eksempel 101 angitte instruks ved omsetning av .6-[(1,2-difenyl-7-nitro-lH-benzimidazol-6-yl)-oksy]heksansyreisopropylester. ;<1>H-NMR (CDC13) : 6 = 1,22 ppm d (J = 7,5 Hz, 6H) ; 1, 43-1, 88 m (6H); 2,30 t (J = 7,5 Hz, 2H); 4,04 t (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). ;Eksempel 103 ;6-[(5,7-dinitro-l,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-syremetylester ;ble erholdt ved omsetning av 5,7-dinitro-l,2-difenyl-6-hydroksy-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 88-91 °C. ;Eksempel 104 ;6-[(5,7-dinitro-l,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-syreisopropylester ;ble erholdt ved omsetning av 5,7-dinitro-l,2-difenyl-6-hydroksy-lH-benzimidazol med 6-bromheksansyreisopropylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 92-93 °C. ;Eksempel 105 ;6-[[5-(acetylamino)-1,2-difenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester ;a) 5-fluor-2,4-dinitrofenol ;0,41 g 1,3-difluor-4,6-dinitrobenzen ble oppløst i 8 ml ;0,5 N vandig natriumhydroksid og oppvarmet i 2 h inntil tilbake-løp. Etter avkjøling ble det fortynnet med vann og ekstrahert tre ganger med dietyleter. Den vandige fase ble gjort sur ved tilsetning av 1 N saltsyre og ekstrahert med dietyleter. Den organiske fase ble tørket over natriumsulfat og konsentrert i vakuum.. ;<1>H-NMR (CDCI3) : 5 = 7,10 ppm d (J = 12 Hz, 1H); 9,03 d (J = 8 Hz, 1H); 11,10 s (1H). ;b) 2,4-dinitro-5-hydroksydifenylamin ;Til suspensjonen av 50 mg 5-fluor-2,4-dinitrofenol i ;0,5 ml etanol tilsatte man 100 ul anilin, omrørte i 30 min og lot blandingen henstå i 15 h. Man foretok avsugning, vasket det faste stoff med 1 N vandig saltsyre og tørket i vakuum. ;<X>H-NMR (CDCI3) : 5 = 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 (bred)(lH); 10,97 s (bred)(1H). ;c) Eddiksyre-(2,4-dinitro-5-fenylamino)fenylester ;Til 275 mg 2,4-dinitro-5-hydroksydifenylamin i 1 ml ;pyridin tilsatte man 0,11 ml eddiksyreanhydrid og foretok omrøring i 30 min i isbad og deretter i enda 1 h ved 20 °C. Etter fortynning med etylacetat ble det vasket tre ganger med iskald 1 N vandig saltsyre, én gang med mettet kaliumbikarbonatoppløs-ning og én gang med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum. ;<X>H-NMR (CDCI3) : 5 = 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); 9,95 s (bred)(1H). d) Eddiksyre-(1,2-difenyl-6-hydroksy-lH-benzimidazol-5-yl)amid ble erholdt ved omsetning av eddiksyre-(2,4-dinitro-5-fenyl-amino)fenylester i henhold til den generelle arbeidsinstruks 1 og med påfølgende omsetning med trimetylortobenzoat i henhold til den generelle arbeidsinstruks 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 (bred)(1H). ;6-[[5-(acetylamino)-1,2-difenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester ;ble erholdt ved omsetning av eddiksyre-(1,2-difenyl-6-hydroksy-lH-benzimidazol-5-yl)amid med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. Smp. 128-130 °C-. ;Eksempel 106 ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyre-isopropylester ;ble erholdt ved omsetning av 6-[(1,2-difenyl-5-nitro-lH-benzimidazol-6-yl)oksy]heksansyreisopropylester i henhold til den generelle arbeidsinstruks 1. ;<1>H-NMR (CDC13) : 5 = 1,23 ppm d (J = 7,5 Hz, 6H); 1,47-1, 90 m (6H); 2,32 t (J = 7,5 Hz, 2H); 3,95 t (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); 7,43-7,58 m (5H). ;Eksempel 107 ;6-[[5-[[(4-bromfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 4-brombenzensulfon-syreklorid i henhold til den generelle arbeidsinstruks 13. ;Smp. 173-175 °C. ;Eksempel 108 ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyre-metylester ;ble erholdt ved omsetning av 6-[(1,2-difenyl-5-nitro-lH-benzimidazol-6-yl)oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 1. ;<1>H-NMR (CDCI3) : 6 = 1,48-1, 88 ppm (6H); 2,36 t (J = 7,5 Hz, 2H, CH2 = CO); 3,67 s (3H) ; 3,94 t (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). ;Eksempel 109 ;6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;Smp. 157-159 °C. ;Eksempel 110 ;6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. Smp. 158-159 °C. ;Eksempel 111 ;6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyre ;ble erholdt ved omsetning av 6-[[5-[[(4-klorfenyl)sulfonyl]-amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyremetyl-ester i henhold til den generelle arbeidsinstruks 9. ;Smp. 201-203 °C. ;Eksempel 112 ;6-[[1,2-difenyl-5-[[(3-metylfenyl)sulfonyl]amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 3-metylbenzensulfon-syreklorid i henhold til den generelle arbeidsinstruks 13. Smp. 149-151 °C. ;Eksempel 113 ;6-[[1,2-difenyl-5-[[(4-metylfenyl)sulfonyl]amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 4-metylbenzensulfon-syreklorid i henhold til den generelle arbeidsinstruks 13. Smp. 139-141 °C. ;Eksempel 114 ;6-[[1,2-difenyl-5-[[(4-metoksyfenyl)sulfonyl] amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 4-metoksybenzensulfon-syreklorid i henhold til den generelle arbeidsinstruks 13.. ;<1>H-NMR (CDCI3) : 5 = 1,25 ppm d (J = 7,5 Hz, 6H); 1,35-1, 45 m (2H); 1,59-1, 73 m (4H) ; 2,30 t (J = 7,5 Hz, 2H); 3,72 t (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); 7,99 s (1H). ;Eksempel 115 ;6-[[1,2-difenyl-5-[[[(4-trifluormetyl)fenyl]sulfonyl]amino]-1H-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 4-trifluormetylbenzen-sulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. Smp. 170-171 °C. ;Eksempel 116 ;6-[[5-[[[4-(acetylamino)fenyl]sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 4-ac.etylaminobenzen-sulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. Smp. 100-102 °C. ;Eksempel 117 ;6-[[5-[[bis(3-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med 3-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;Smp. 163-167 °C. ;Eksempel 118 ;6-[[1,2-difenyl-5-[(propylsulfonyl)amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksansyreisopropylester ble omsatt med propansulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;Smp. 126-128 °C. ;Eksempel 119 ;6-[[5-[(benzylsulfonyl)amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yljoksy]-heksansyreisopropylester ble omsatt med benzenmetansulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. Smp. 137-138 °C. ;Eksempel 120 ;4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]metylbenzosyre-metylester■- ;ble fremstilt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 4-(brommetyl)benzosyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 180-184 °C. ;Eksempel 121 ;4- [ (1,2-difenyl-lH-benzimidazol-6-yl)oksy]metylbenzosyre ble fremstilt ved omsetning av 4-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]metylbenzosyremetylester i henhold til den generelle arbeidsinstruks 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). ;Eksempel 122 ;4-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]metyl-benzosyremetylester ;ble fremstilt ved omsetning av 6-hydroksy-l-(3-metylfenyl)-2-fenyl-lH-benzimidazol med 4-(brommetyl)benzosyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 138-142 °C. ;Eksempel 123 ;4-t[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]metyl-benzosyremetylester ;ble fremstilt ved omsetning av 6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol med 4-(brommetyl)benzosyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 145-148 °C. ;Eksempel 124 ;2-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]eddiksyre-tert.-butylester ;0,2 g [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etan-l-ol ble suspendert i 1,7 ml toluen og 0,7 ml tetrahydrofuran. Til dette tilsatte man 0,1 ml bromeddiksyre-tert.-butylester og 13 mg tetrabutylammoniumhydrogensulfat og 1,45 ml 32%-ig natriumhydroksid og lot omrøre i 48 h. Man tilsatte ytterligere 0,1 ml bromeddiksyre-tert.-butylester og 13 mg tetrabutyl-ammoniumhydrogensulf at og etterlot blandingen i ultralydbad i 48 h. Deretter ble det fortynnet med vann og ekstrahert tre ganger med toluen. De kombinerte, organiske faser ble vasket med vann og mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. ;<1>H-NMR (CDC13) : 6 = 1,43 ppm s (9H); 3,91 t (J = 6 Hz, 2H); 4,10 s (2H); 4,17 t (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). ;Eksempel 125 ;2-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]eddiksyre 50 mg 2-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-etoksy]eddiksyre-tert.-butylester ble oppløst i 0,5 ml tri-fluoreddiksyre og omrørt i 48 h. Deretter ble det fortynnet med vann og ekstrahert tre ganger med etylacetat. De kombinerte, organiske faser ble vasket med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. ;Smp. 134-136 °C. ;Eksempel 126 ;2-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]eddiksyre-metylester ;35 mg 2-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-etoksy]eddiksyre ble.oppløst i 0,4 ml N,N-dimetylformamid og forsynt med 29 mg cesiumkarbonat og 50 ul metyljodid. Man omrørte i 20 h og konsentrerte deretter i vakuum og kromato-graf erte på silikagel. ;<X>H-NMR (CDCI3) : = 3,73 ppm s (3H) ; 3,93 t (J = 6 Hz, 2H) ; 4,18 t (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). ;Eksempel 127 ;3-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]propansyre-tert.-butylester ;0,2 g [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etan-l-ol ble suspendert i 1,7 ml toluen og 0,7 ml tetrahydrofuran. Til dette tilsatte man 60 ul akrylsyre-tert.-butylester, 13 mg tetrabutylammoniumhydrogensulfat og 1,45 ml 32%-ig natriumhydroksid og lot omrøre i 48 h. Man tilsatte ytterligere 60 ul akrylsyre-tert.-butylester og 13 mg tetrabutylammoniumhydrogensulfat og etterlot blandingen i 48 h i ultralydbad. Deretter ble det fortynnet med vann og ekstrahert tre ganger med toluen. De kombinerte, organiske faser ble vasket med vann og mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. ;^-NMR (CDCI3) : 5 = 1,45 ppm s (9H); 2,52 t (J = 8 Hz, 2H) ; 3,73-3,84 m (4H); 4,10 t (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). ;Eksempel 128 ;3-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]propansyre 50 mg 3-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-etoksy]propansyre-tert.-butylester ble oppløst i 0,5 ml tri-fluoreddiksyre og omrørt i 15 h. Deretter ble det fortynnet med vann og ekstrahert tre ganger med etylacetat. De kombinerte, organiske faser ble vasket med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. ;<X>H-NMR (D6-DMSO) : 5 = 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). ;Eksempel 129 ;3-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]propan-syremetylester 35 mg 3-[2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-etoksy]propansyre ble oppløst i 0,4 ml N,N-dimetylformamid, forsynt med 28 mg cesiumkarbonat og 50 ul metyljodid og omrørt i 30 h. Deretter ble det fortynnet med vann og ekstrahert tre ganger med etylacetat. De kombinerte, organiske faser ble vasket med mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. Smp. 91-93 °C. ;Eksempel 130 ;3-[3-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]propoksy]propan-syre- tert .-butylester ;0,2 g 3-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]propan-l-ol ble suspendert i 1,7 ml toluen og 0,7 ml tetrahydrofuran. Til dette tilsatte man 60 ul akrylsyre-tert.-butylester, 13 mg tetrabutylammoniumhydrogensulfat og 1,47 ml 32%-ig natrium-hydroksidoppløsning og lot omrøre i 48 h. Man tilsatte ytter-. ligere 60 ul akrylsyre-tert.-butylester og 13 mg tetrabutyl-ammoniumhydrogensulf at og lot blandingen henstå i 48 h i ultralydbad. Deretter ble det fortynnet med vann og ekstrahert tre ganger med toluen. De kombinerte, organiske faser ble vasket med vann og mettet natriumkloridoppløsning, tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. ;Smp. 95-98 °C. ;Eksempel 131 ;(E/Z)-5-(1,2-difenyl-lH-benzimidazol-6-yl)pent-4-ensyremetyl-ester ;a) 1,2-difenyl-6-metyl-lH-benzimidazol ;5,1 g 5-metyl-2-nitrodifenylamin ble hydrert i 55 ml ;etanol i henhold til den generelle arbeidsinstruks 1. Råproduktet ble omsatt med trimetylortobenzoat i henhold til den generelle arbeidsinstruks 3. ;Smp. 134-136 °C. ;b) 1,2-difenyl-lH-benzimidazol-6-karbaldehyd ;1 g 1,2-difenyl-6-metyl-lH-benzimidazol ble suspendert ;i 31 ml 40%-ig svovelsyre og forsynt med 13,5 g ceriumammonium-nitrat. Man lot omrøre i 2,5 h ved 80 °C, avkjølte til 20 °C og rørte forsiktig inn mettet, vandig natriumbikarbonatoppløsning. Blandingen ble ekstrahert tre ganger med etylacetat, de kombinerte ekstrakter ble vasket med mettet, vandig natriumklorid-oppløsning, tørket over natriumsulfat og konsentrert til tørrhet i vakuum. Resten ble kromatografert på silikagel. ;<X>H-NMR (CDClj) : 5 = 7,30-7, 42 ppm m (5H); 7,50-7, 66 m (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-difenyl-lH-benzimidazol-6-yl)pent-4-ensyremetyl-ester ;ble erholdt ved omsetning av 1,2-difenyl-lH-benzimidazol-6-karbaldehyd med 3-karboksypropyltrifenylfosfoniumbromid i henhold til den generelle arbeidsinstruks 12. ;<X>H-NMR (CDC13) : 5 = 2,40-2,71 ppm m (4H) ; 3, 68 (3, 66) hver s (3H); 5,56-5,64 (6,12-6,22) hver m (1H); 6,50 d (J = 18 Hz, 1H); 6,58 d (bred)(J = 12 Hz, 1H); 7,12 (7,15) hver s (bred)(lH); 7,25-7,40 m (6H); 7,45-7,62 m (5H); 7,80 (7,83) hver d (J = ;8 Hz, 1H). ;Eksempel 132 ;E-5-(1,2-difenyl-lH-benzimidazol-6-yl)pent-4-ensyre ;ble erholdt ved omsetning av (E/Z)-5-(1,2-difenyl-lH-benzimidazol-6-yl)pent-4-ensyremetylester i henhold til den generelle arbeidsinstruks 9. ;<:>H-NMR (CD3OD): 5 = 2,26-2,43 ppm m (4H); 6,10-6,21 m (1H); 6,45 d (J = 18 Hz, 1H); 7,08 s (1H); 7,22-7,52 m (11H); 7,59 d (J = ;8 Hz, 1H). ;Eksempel 133 ;5-(1,2-difenyl-lH-benzimidazol-6-yl)pentansyremetylester ble erholdt ved omsetning av (E/Z)-5-(1,2-difenyl-lH-benzimidazol-6-yl)pent-4-ensyremetylester i henhold til den generelle arbeidsinstruks 1. ;<X>H-NMR (CDCI3) : 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 (bred)(lH); 7,17 dd (J = 8, 2 Hz, 1H); 7,25-7,38 m (5H); 7,45-7,60 m (5H); 7,79 d (J = 8 Hz, 1H) . ;Eksempel 134 ;5- (1,2-difenyl-lH-benzimidazol-6-yl)pentansyre ;ble erholdt ved omsetning av 5-(1,2-difenyl-lH-benzimidazol-6-yl)pentansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 192-193 °C. ;Eksempel 135 ;(E/Z)-6-(1,2-difenyl-lH-benzimidazol-6-yl)heks-5-ensyremetyl-ester ;ble erholdt ved omsetning av 1,2-difenyl-lH-benzimidazol-6-karbaldehyd med 4-karboksybutyltrifenylfosfoniumbromid i henhold til den generelle arbeidsinstruks 12. ;<X>H-NMR (CDCI3) : 6 = 1,72-1,88 ppm m (2H) ; 2,20-2, 42 m (4H); 3,65 (3,67) hver s (3H, CH3) ; 5,57-5,68 (6, 10-6,20) hver m (1H); 6,48 d (J = 18 Hz, 1H); 6,56 d (bred)(J = 12 Hz, 1H); 7,12 (7,16) hver s (bred)(1H); 7,25-7,38 m (6H); 7,45-7,60 m (5H); 7,80 (7,84) hver d (J = 8 Hz, 1H). ;Eksempel 136 ;(E/Z)-6-(1,2-difenyl-lH-benzimidazol-6-yl)heks-5-ensyre ble erholdt ved omsetning av (E/Z)-6-(1,2-difenyl-lH-benzimidazol-6-yl)heks-5-ensyremetylester i henhold til den generelle arbeidsinstruks 9. ;<X>H-NMR (CDCI3) : 6 = 1,74-1, 89 ppm m (2H); 2,22-2,43 m (4H); 5,58-5,68 (6,10-6,22) hver m (1H); 6,47 d (J = 18 Hz, 1H); 6,55 d (bred)(J = 12 Hz, 1H); 7,11 (7,14) hver s (bred)(1H); 7,25-7,40 m (6 H); 7,48-7,59 m (5H); 7,80 (7,85) hver d (J = 8 Hz, 1H). ;Eksempel 137 ;6- (1,2-difenyl-lH-benzimidazol-6-yl)heksansyremetylester ble erholdt ved omsetning av (E/Z)-6-(1,2-difenyl-lH-benzimidazol-6-yl)héks-5-ensyremetylester i henhold til den generelle arbeidsinstruks 1. ;<1>H-NMR (CDCI3) : 5 = 1,32-1, 43 ppm m (2H)'; 1, 62-1,74 m (4H) ; 2,31 t (J = 7,5 -Hz, 2H) ; 2,72 t (J = 7,5. Hz, 2H) ; 3,56 s (3H) ; 7,02 s (bred)(1H); 7,18 dd (J = 8, 2 Hz, 1H); 7,27-7,38 m (5H); 7,45-. 7,60 m (5H); 7,80 d (J = 8 Hz, 1H). ;Eksempel 138 ;6-(1,2-difenyl-lH-benzimidazol-6-yl)heksansyre ;ble erholdt ved omsetning av 6-(1,2-difenyl-lH-benzimidazol-6-yl)heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;<1>H-NMR JCDC1-3) : 6 = 1,30-1 ,^5 ppm m (2H) ; 1,54-1,74 m (4H) ; 2,32 t (J = 7,5 Hz, 2H); 2,70 t (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). ;Eksempel 139 ;(E/Z)-7-(1,2-difenyl-lH-benzimidazol-6-yl)hept-6-ensyremetyl-ester ;ble erholdt ved omsetning av 1,2-difenyl-lH-benzimidazol-6-karbaldehyd med 5-karboksypentyltrifenylfosfoniumbromid i henhold til den generelle arbeidsinstruks 12. ;^-NMR (CDCI3) : 5 = 1,43-1,55 ppm m (2H) ; 1,58-1,72 m (2H) ; 2,18-2,38 m (4H); 3, 65 (3, 66) hver s (3H, CH3) ; 5,58-5, 68 (6,12-6,22) hver m (1H); 6,45 d (J = 18 Hz, 1H); 6,54 d (bred) (J = 12 Hz, 1H); 7,12 (7,14) hver s (bred)(lH); 7,26-7,40 m (6H); 7,48-7,60 m (5H); 7,80 (7,83) hver d (J = 8 Hz, 1H). ;Eksempel 140 ;(E/Z)-7-(l,2-difenyl-lH-benzimidazol-6-yl)hept-6-ensyre ble erholdt ved .omsetning av (E/Z)-7-(1,2-difenyl-lH-benzimidazol-6-yl)hept-6-ensyremetylester i henhold til den generelle arbeidsinstruks 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) hver s (bred)(lH); 7,32-7,64 m (11H); 7,70 (7,78) hver d (J = 8 Hz, 1H); 12,00 s (bred)(1H). ;Eksempel 141 ;7-(1,2-difenyl-lH-benzimidazol-6-yl)heptansyremetylester ble erholdt ved omsetning av (E/Z)-7-(1,2-difenyl-lH-benzimidazol-6-yl)hept-6-ensyremetylester i henhold til den generelle arbeidsinstruks 1. ;<1>H-NMR (CDC13) : 6 = 1,30-1,42 ppm m (4H); 1,55-1,70 m (4H); 2,30 t (J = 7,5 Hz, 2H); 2,68 t (J = 7,5 Hz, 2H); 3,56 s (3H); 7,02 s (bred)(lH); 7,18 dd (J = 8, 2 Hz, 1H); 7,28-7,35 m (5H); 7,45-7,58 m (5H); 7,79 d (J = 8 Hz, 1H) . ;Eksempel 142 ;7-(1,2-difenyl-lH-benzimidazol-6-yl)heptansyre ;ble erholdt ved omsetning av 7-(1,2-difenyl-lH-benzimidazol-6-yl)heptansyremetylester i henhold til den generelle arbeidsinstruks 9. ;Smp. 99-103 °C. ;Eksempel 143 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ;Eksempel 144 ;N- (fenylsulfonyl) -N- (1,2-difenyl-lH-benzimidazol-5-yl)benzen-sulfonamid ;a) 5-amino-l,2-difenyl-lH-benzimidazol ;2, 4-diaminodifenylamin blir omsatt med trimetylortobenzoat i henhold til den generelle arbeidsinstruks 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-l,2-difenyl-lH-benzimidazol ble omsatt med benzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;143: Smp. 196-205 °C. ;144: <1>H-NMR (CDC13) : 5 = 6,94 ppm dd (J = 7,5, 2 Hz, 1H); 7,20 d (J = 2 Hz, 1H); 7,26-8,04 m (21H). ;Eksempel 145 ;3-klor-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ;Eksempel 146 ;N- [(3-klorfenyl)sulfonyl]-N-(1,2-difenyl-lH-benzimidazol-5-yl) - ;(3-klorbenzen)sulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 3-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;145: Smp. 160-162 °C. ;146: <1>H-NMR (CDC13) : 5 = 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 (bred)(2H); 7,90 d (bred)(2H); 8,00 d (bred)(2H). ;Eksempel 147 ;4-klor-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;<1>H-NMR (CDC13) : 6 = 6,86 ppm s (bred) (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). ;Eksempel 148 ;4-brom-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ;Eksempel 149 ;N-(4-bromfenylsulfonyl)-N-(1,2-difenyl-lH-benzimidazol-5-yl)-4-brombenzensulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 4-brombenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;148: Smp. 135-139 °C. ;149: <1>H-NMR (CDCI3) : 5 = 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). ;Eksempel 150 ;4-(trifluormetyl)-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensul-f onamid ;Eksempel 151 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)-N-[(3-trifluormetyl)fenylsulfonyl]-(3-trifluormetyl)benzensulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 3-trifluormetylbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;150: Smp. 116-121 °C. ;151: Smp. 238-241 °C. ;Eksempel 152 ;3- metyl-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ;Eksempel 153 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)-N-(3-metylfenylsulfonyl)-3-me tylbenzensulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 3-metylbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;152: Smp. 192-195 °C. ;153: Smp. 173-176 °C. ;Eksempel 154 ;4- metyl-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ;Eksempel 155 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)-N-(4-metylfenylsulfonyl)-4-metylbenzensulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 4-metylbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;154: <1>H-NMR (CDCI3) : 5 = 2,38 ppm s (3H) ; 6,77 s (bred) (1H) ; 7,14-7,55 m (14H); 7,66 d (J = 10 Hz, 2H). ;155: Smp. 234-236 °C. ;Eksempel 156 ;4-metoksy-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ;Eksempel 157 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)-N-(4-metoksyfenylsulfonyl)-4-metoksybenzensulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 4-metoksybenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;156: <1>H-NMR (CDC13) : 5 = 3,82 ppm s (3H); 6,78 s (bred) (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 (CDCI3) : 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) . ;Eksempel 158 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)propansulfonamid ;Eksempel 159 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)-N-(propylsulfonyl)-propansulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med propanbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;158: <1>H-NMR (CDC13/D6-DMS0) : 6 = 0,80 ppm t (J = 7,5 Hz, 3H) ; 1,65 m (2H); 2,82 m (2H); 6,95 d (J = 7,5 Hz, 1H); 7,08 dd (J = 7,5, 2 Hz, 1H); 7,10-7,40 m (10H); 7,61 d (J = 2 Hz, 1H); 9,05 s (bred)(1H, NH). ;159: <1>H-NMR (CDCI3) : 5 = 1,08 ppm t (J = 7,5 Hz, 3H); 1,12 t (J = 7,5 Hz, 3H); 2,00 m (4H); 3,60 m (4H); 7,25-7,63 m (13H). ;Eksempel 160 ;N-(1,2-difenyl-lH-benzimidazol-5-yl)benzenmetansulfonamid ;5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med benzenmetansulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. ;Smp. 185-188 °C. ;Eksempel 161 ;6-[[1,2-difenyl-lH-benzimidazol-5-yl] amino]heksansyremetylester ;Eksempel 162 ;6-[N-(1,2-difenyl-lH-benzimidazol-5-yl)-N-[(5-metoksykarbonyl)-pentyl]amino]heksansyremetylester ;Til en oppløsning av 285 mg 5-amino-l,2-difenyl-lH-benzimidazol i 5 ml metanol tilsatte man 207 mg 6-bromheksansyremetylester, 138 mg kaliumkarbonat og 150 mg natriumjodid og lot omrøre i 3 d ved 20 °C. Man tilsatte vann, ekstraherte tre ganger med etylacetat, tørket de kombinerte, organiske faser over natriumsulfat og konsentrerte i vakuum. Resten ble kromatografert på silikagel. ;161: Smp. 109-113 °C. ;162: <1>H-NMR (CDCI3) : 6 = 1,30-1,43 m (4H); 1,53-1,73 m (8H); 2,32 t (J = 7,5 Hz, 4H); 3,30 t (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); 7,42-7,58 m (5H) . ;Eksempel 163 ;6-[[1,2-difenyl-lH-benzimidazol-5-yl] amino]heksansyre ble erholdt ved omsetning av 6-[[1,2-difenyl-lH-benzimidazol-5-yl]amino]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;<X>H-NMR (D6-DMSO) : 5 = 1,35-1,50 ppm m (2H) ; 1, 50-1, 68 m (4H); 2,23 t (J = 7,5 Hz, 2H); 3,05 t (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); 7,30-7,40 m (4H); 7,45-7,62 m (6H). ;Eksempel 164 ;6-[[2-fenyl-l-[4-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;a) (5-hydroksy-2-nitrofenyl)[(4-(fenylmetoksy)fenyl] amin ;1 g 3-fluor-4-nitrofenol og 3,8 g 4-benzyloksyanilin ;ble omrørt i 6,5 h ved 150 °C. Chargen ble deretter fortynnet med diklormetan. Etter ekstraksjon to ganger med 1 N vandig saltsyre og vasking med vann ble det ekstrahert to ganger med 2 N vandig natriumhydroksidoppløsning. Den basiske vannfase ble forsynt med etylacetat og 1 N vandig saltsyre. Etter faseseparering ble den organiske fase ekstrahert flere ganger med 1 N vandig saltsyre. Etter vasking av den organiske.fase med mettet natriumklorid- ;oppløsning ble .det tørket over natriumsulfat, konsentrert i vakuum og resten kromatografert på silikagel. ;<1>H-NMR (D6-DMSO) : 5 = 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-(fenylmetoksy)fenyl]amino]fenyl]oksy]-heksansyremetylester ble erholdt ved omsetning av (5-hydroksy-2-nitrofenyl)[(4-(fenylmetoksy)fenyl]amin med 6-bromheksansyremetylester i henhold, til-den generelle arbeidsinstruks 8. <1>H-NMR (CDC13) : 6 = 1,37-1,50 m (2H) ; 1,59-1, 80 m (4H); 2,33 t (J = 7,5 Hz, 2H); 3,67 s (3H) ; 3,83 t (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-fenyl-l-[4-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester ble erholdt ved reduksjon av 6-[[4-nitro-3-[[4-(fenylmetoksy)-fenyl]amino]fenyl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 2 og med påfølgende syklisering med trimetylortobenzoat i henhold til den generelle arbeidsinstruks 3. <1>H-NMR (CDCI3) : 6 = 1,43-1,58 m (2H) ; 1, 65-1,86 m (4H) ; 2,35 t (J = 7,5 Hz, 2H); 3,67 s (3H); 3,94 t (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). Eksempel 165 6-[[2-fenyl-l-[4r(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyre 6-[[2-fenyl-l-[4-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester ble omsatt i henhold til den generelle arbeidsinstruks 9. <1>H-NMR (D6-DMSO) : 5 = 1,36-1, 62 m (4H); 1, 65-1,78 m (2H) ; 2,22 t (J = 7,5 Hz, 2H); 3,92 t (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). Eksempel 166 6-[[1-(4-hydroksyfenyl)-2-fenyl-lH-ben^imidazol-6-yl]oksy] - heksansyre 6-[[2-fenyl-l-[4-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyre ble omsatt i henhold til den generelle arbeidsinstruks 1. <X>H-NMR (D6-DMSO): 5 = 1,37-1,79 m (6H); 2,22 t (J = 7,5 Hz, 2H); 3,92 t (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); 7,36 m (3H); 7,52 m (2H); 7,63 d (J = 8 Hz, 1H). ;Eksempel 167 ;6-[[2-fenyl-l-[3-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;a) (5-hydroksy-2-nitrofenyl)[(3-(fenylmetoksy)fenyl]amin ;1 g 3-fluor-4-nitrofenol og 3,81 g 3-benzyloksyanilin ;ble omrørt i 22 h ved 150 °C. Deretter ble blandingen tatt opp i litt diklormetan og kromatografert direkte på silikagel. ;<1>H-NMR (CDC13) : 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-(fenylmetoksy)fenyl]amino]fenyl]oksy]-heksansyremetylester ;ble erholdt ved omsetning av (5-hydroksy-2-nitrofenyl)[(3-(fenylmetoksy)fenyl]amin med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;^-NMR (CDCI3) : 5 = 1,40-1,53 m (2H) ; 1,61-1,82 m (4H); -2,34 t (J = 7,5 Hz, 2H); 3,67 s (3H); 3,88 t (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-fenyl-l-[3-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;ble erholdt ved reduksjon av 6-[[4-nitro-3-[[3-(fenylmetoksy)-fenyl]amino]fenyl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 2 og med påfølgende syklisering med ;trimetylortobenzoat i henhold til den generelle arbeidsinstruks 3. <1>H-NMR (CDCI3) : 5 = 1,45-1, 60 m (2H) ; 1, 66-1, 88 m (4H) ; 2,35 t (J = 7,5 Hz, 2H); 3,68 s (3H); 3,93 t (J = 7,5 Hz, 2H); 5,02 s ;(2H); 6,69 d (J = 2 Hz, 1H); 6,90 m (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). ;Eksempel 168 ;6-[[2-fenyl-l-[3-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyre ;6-[[2-fenyl-l-[3-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester ble omsatt i henhold til den generelle arbeidsinstruks 9. ;<1>H-NMR (CDCI3) : 5 = 1,49-1, 62 m (2H) ; 1, 67-1, 88 m (4H) ; 2,39 t (J = 7,5 Hz, 2H); 3,93 t (J = 7,5 Hz, 2H); 5,03 s (2H); 6,68 d (J = 2 Hz, 1H); 6,91 m (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) . ;Eksempel 169 ;6-[[1-(3-hydroksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyre ;6-[[2-fenyl-l-[3-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyre ble omsatt i henhold tii den generelle arbeidsinstruks 1. ;<1>H-NMR (D6-DMSO): 5 = 1,39-1,80 m (6H); 2,23 t (J = 7,5 Hz, 2H) ; 3,94 t (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); 6,94 m (2H); 7,38 m (4H); 7,53 m (2H); 7,66 d (J = 8 Hz, 1H). ;Eksempel 170 ;6-[[1-(3-hydroksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester ;6-[[2-fenyl-l-[3-(fenylmetoksy)fenyl]-lH-benzimidazol-6-yl]oksy]heksansyremetylester ble omsatt i henhold til den generelle arbeidsinstruks 1. <1>H-NMR (D6-DMSO)-: 6 = 1,38-1, 80 m (6H); 2,32 t (J = 7,5 Hz, 2H) ; 3,59 s (3H); 3,94 t (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); 7,38 m (4H); 7,54 m (2H); 7,67 d (J = 8 Hz, 1H). ;Eksempel 171 ;6-[[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreetylester ;ble erholdt ved omsetning av 6-hydroksy-l-(3-nitrofenyl)-2-fenylbenzimidazol (DE 4330959) med 6-bromheksansyreetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 104-106 °C. ;Eksempel 172 ;6-[[4-brom-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;a) 4-brom-6-metoksy-2-fenyl-lH-benzimidazol ;36,6 g 4-amino-3-brom-5-nitroanisol (J. Chem. Soc. ;1966, 1769) ble forlagt på forhånd i 750 ml etanol og.forsynt med 19,8 g jernpulver og 126 ml eddiksyre. Etter omrøring i 2,5 h ved 55 ?C ble 350 ml diklormetan tilsatt og blandingen gjort basisk med 2 N natriumhydroksidoppløsning. Etter filtrering over Celite ble det vasket med vann og mettet koksalt-oppløsning og konsentrert. Det således erholdte rå fenylendiamin ble omsatt med trimetylortobenzoat i henhold til den generelle arbeidsinstruks 3. ;Smp. 203-205 °C. ;b) 4-brom-6-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol 2,5 g 4-brom-6-metoksy-2-fenyl-lH-benzimidazol og ;2,24 g 4-(metylbenzen)borsyre ble omrørt med 1,5 g vannfritt kobber(II)acetat og ca. 3 g molekylsil i 35 ml pyridin i 7 h ved 100 °C. Etter tilsetning av diklormetan og Celite ble det foretatt konsentrering og kromatografering på silikagel med en heksan/etylacetatblanding. ;Smp. 209-210 °C. ;c) 4-brom-6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol 1,2 g 4-brom-6-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol, 6 ml eddiksyre og 6 ml vandig bromhydrogensyre (62%-ig) kokes i 5,5 h. Deretter utfelles med vann, og bunnfallet blir avsuget. Dette ble deretter fordelt mellom etylacetat og 2 N natriumhydroksidoppløsning. Etter vasking av den organiske fase med vann ble konsentrering foretatt. ;Smp. 136-137 °C. ;6-[[4-brom-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;ble erholdt ved omsetning av 4-brom-6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 136 °C. ;Eksempel 173 ;6-[[4-acetyl-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;0,5 g 4-brom-6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol, 0,37 ml (a-etoksyvinyl)tributyltinn og 140 mg diklorbis(trifenylfosfin)palladium ble omrørt i 10 ml toluen i 18 h ved 100 °C. Etter avkjøling ble det omrørt i 0,25 h med 2 N vandig saltsyre. Etter faseseparering ble den organiske fase vasket med vann og konsentrert. Resten ble kromatografert på silikagel med en heksan/etylacetatblanding. ;Smp. 114-115 °C. ;Eksempel 174 ;6~[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksan-syremetylester ;a) 5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol ;16,8 g 5-metoksy-2-fenyl-lH-benzimidazol (Bull. Sei. ;Fac. Chim. Ind. Bologna, 11, 1953, 42) og 20,4 g 4-(metyl-benzen)borsyre omsettes i henhold til den generelle arbeidsinstruks 14. ;<X>H-NMR (CDC13) : 5 = 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); 7,25-7,38 m (6H); 7,57 m (2H). ;Dessuten ble 6-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol erholdt. b) 5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt fra 5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 6. ;Smp. 270 °C. ;6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksan-syremetylester ;ble erholdt fra 5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol ved omsetning med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;<1>H-NMR (CDC13) : 5 = 1, 48-1, 92 m (6H); 2,38 t (J = 7,5 Hz, 2H); 2,46 s (3H); 3,69 s (3H); 4,06 t (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); 7,57 m (2H). ;Eksempel 175 ;6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksan-syre ;ble erholdt fra 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;<1>H-NMR (D6-DMSO): 6 = 1,41-1,67 m (4H); 1,70-1,83 m (2H); 2,26 t (J = 7,5 Hz, 2H); 2,43 s (3H); 4,05 t (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); 7,52 m (2H); 11,92 s (br.)(1H). ;Eksempel 176 ;6-[[2-fenyl-l-[4-(tiometyl)fenyl]-lH-benzimidazol-5-yl]oksy]-heksansyremetylester a) 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester 4,84 g 2-fenyl-5-hydroksy-lH-benzimidazol (Izv. Akad. ;Nauk. SSSR Ser. Chim. 8, 1990, 1888) ble erholdt ved omsetning med 6-bromheksansyremetylester i henhold til den generelle arbeidsinstruks 8. ;<1>H-NMR (CDCI3) : 5 = 1,43-1,58 m (2H); 1, 64-1, 87 m (4H); 2,37 t (J = 7,5 Hz, 2H); 3,69 s (3H); 3,94 t (J = 7,5 Hz, 2H); 6,87 dd (J = 8, 2 Hz, 1H);. 7,02 s (br.); 7,40-7,57 m (4H); 8,05 m (2H). ;6-[[2-fenyl-l-[4-(tiometyl)fenyl]-lH-benzimidazol-5-yl]oksy]-heksansyremetylester ;ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med 4-(tiometylbenzen)borsyre i henhold til den generelle arbeidsinstruks 14. ;<X>H-NMR (CDC13) : 6 = 1,48-1,61 m (2H) ; 1, 66-1, 92 m (4H) ; 2,36 t (J = 7,5 Hz, 2H); 2,54 s (3H); 3,68 s (3H); 4,05 t (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); 7,57 m (2H) . ;Eksempel 177 6-[[2-fenyl-l-[(4-tiometyl)fenyl]-lH-benzimidazol-6-yl]oksy]-heksansyremetylester ;ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med 4-(tiometylbenzen)borsyre i henhold til den generelle arbeidsinstruks 14. ;<1>H-NMR (CDCI3) : 5 = 1, 45-1,57 m (2H) ; 1, 62-1,86 m (4H); 2,44 t (J = 7,5 Hz, 2H) ; 2,56 s (3H.) ; 3,66 s (3H) ; 3,93 t (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); 7,54 m (2H); 7,73 d (J = 8 Hz, 1H). ;Eksempel 178 ;6-[[2-fenyl-l-(3-tienyl)-lH-benzimidazol-5-yl]oksy]heksansyre-metylester ;ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med tiofen-3-borsyre i henhold til den generelle arbeidsinstruks 14. ;<1>H-NMR (CDCI3) : 6 = 1, 48-1, 62 m (2H) ; 1, 66-1, 92 m (4H); 2,47 t (J = 7,5 Hz, 2H); 3,68 s (3H); 4,04 t (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); 7,30-7,40 m (4H); 7,46 dd (J = 5, 3 Hz, 1H) ; 7, 60 m (2H) . ;Eksempel 179 ;6-[[2-fenyl-l-(3-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ;ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med tiofen-3-borsyre i henhold til den generelle arbeidsinstruks 14. ;1H-NMR (CDCI3) : 6 = 1, 45-1,58 m (2H) ; 1, 64-1, 87 m (4H) ; 2,35 t (J = 7,5 Hz, 2H); 3,67 s (3H); 3,97 t (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); 7,30-7,38 m (4H); 7,47 dd (J = 5, ;3 Hz, 1H); 7,58 m (2H) ; 7,73 d (J = 8 Hz, 1H) . Eksempel 180 4-[3-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-fenoksy]butansyremetylester a) 6-(3-metoksyfenoksy)-1-(4-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt fra 6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol og 3-metoksybenzenborsyre i henhold til den generelle arbeidsinstruks 14. ;Smp. 120-122 °C. b) 3-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]fenol ble erholdt ved omsetning av 6-(3-metoksyfenoksy)-1-(4-metylfenyl) -2-f enyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 6 under tilsetning av 10 mol% heksadecyltri-butylfosfoniumbromid. ;Smp. 252-253 °C. ;4-[3-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-fenoksy]butansyremetylester ;ble erholdt ved omsetning av 3-[ [1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]fenol med 4-bromsmørsyremetylester i henhold til den generelle arbeidsinstruks 8. ;<1>H-NMR (CDCI3) : 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 t (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); 7,59 m (2H); 7,87 d (J = 8 Hz, 1H) . ;Eksempel 181 ;4-[4-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-fenoksy]butansyremetylester ;a) 6-(4-metoksyfenoksy)-1-(4-metylfenyl)-2-fenyl-lH-benzimidazol ble erholdt fra 6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol og 4-metoksybenzenborsyre i henhold til den generelle arbeidsinstruks 14. <1>H-NMR (CDC13) : 5 = 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); 7,57 m (2H); 7,82 d (J = 8 Hz, 1H). b) 4-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]fenol ble erholdt ved omsetning av 6-(3-metoksyfenoksy)-1-(4-metylfenyl) -2-f enyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 6 under tilsetning av 10 mol% heksadecyltri-butylfosfoniumbromid. ;<1>H-NMR (De-DMSO): 6 = 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); 7,49 m (2H); 7,75 d (J = 8 Hz, 1H); 9,32 s (1H). ;4-[4-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-fenoksy]butansyremetylester ;ble erholdt ved omsetning av 4-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]fenol med 4-bromsmørsyremetylester i henhold til den generelle arbeidsinstruks 8r. ;<1>H-NMR (CDCI3) : 6 = 2,03-2,16 m (2H) ; 2,42 s (3H) ; 2,53 t (J = 7,5 Hz, 2H); 3,69 s (3H); 3,97 t (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).; 7,24-7,38 m (5H); 7,57 m (2H); 7,79 d (J = 8 Hz, 1H). ;Eksempel 182 ;[4-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]fen-oksy] eddiksyremetylester ;ble erholdt ved omsetning av 4-[[l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]fenol med bromeddiksyremetylester i henhold til den generelle arbeidsinstruks 8. ;<X>H-NMR (CDCI3) : 5 = 2,43 s (3H) ; 3,82 s (3H) ; 4,61 s (2H) ; 6,78T 6,96 m (5H); 7,00 dd (J = 8, 2 Hz, 1H); 7,14 d (J = 8, Hz, 2H); 7,23-7,38 m (5H); 7,56 m (2H); 7,80 d (J = 8 Hz, 1H). ;Eksempel 183 ;4-[(1,2-difenyl-lH-benzimidazol-6-yl]oksy]butansyremetylester ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 4-brombutansyremetylester i henhold til den generelle arbeidsinstruks 8. ;Smp. 107-110 °C. ;Eksempel 184 ;6-[[2-fenyl-l-(3-pyridyl)-lH-benzimidazol-5-yl]oksy]heksansyre-metylester ;ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med pyridin-3-borsyre i henhold til den generelle arbeidsinstruks 14. ;MS (EI): 415 (molekyliontopp). ;Eksempel 185 ;6-[[2-fenyl-l-(3-pyridyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ;ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med pyridin-3-borsyre i henhold til den generelle arbeidsinstruks 14. ;MS (EI): 415 (molekyliontopp). ;Eksempel 186 ;6-[[2-fenyl-l-(2-pyridyl)-lH-benzimidazol-5-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med 2-fluorpyridin i henhold til den generelle arbeidsinstruks 15. ;MS (EI): 401 (molekyliontopp). ;Eksempel 187 ;6-[[2-fenyl-l-(2-pyridyl)-lH-benzimidazol-6-yl]oksy]heksansyre ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med 2-fluorpyridin i henhold til den generelle arbeidsinstruks 15. ;MS (EI): 401 (molekyliontopp). ;Eksempel 188 ;6-t[2-fenyl-l-(4-pyridyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ;ble erholdt ved omsetning av 6-[[2-fenyl]-lH-benzimidazol-5-yl]oksy]heksansyremetylester med pyridin-4-borsyre i henhold til den generelle arbeidsinstruks 14. ;MS (EI): 415 (molekyliontopp). ;Eksempel 189 ;6-[[2-(4-fluorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;ble erholdt ved omsetning av 6-[[4-amino-3-(fenylamino)fenyl]-oksy]heksansyremetylester med 4-fluorbenzoylklorid i henhold til den generelle arbeidsinstruks 5. ;MS (EI): 432 (molekyliontopp). ;Eksempel 190 ;6-[[2-(4-metoksyfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreme tyles ter ;ble erholdt ved omsetning av 6-[[4-amino-3-(fenylamino)fenyl]-oksy]heksansyremetylester med 4-metoksybenzoylklorid i henhold til den generelle arbeidsinstruks 5. ;MS (EI): 444 (molekyliontopp). ;Eksempel 191 ;6-[[2-(3-fluorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;ble erholdt ved omsetning av 6-[[4-amino-3-(fenylamino)fenyl]-oksy]heksansyremetylester med 3-fluorbenzoylklorid i henhold til den generelle arbeidsinstruks 5. ;MS (EI): 432 (molekyliontopp). ;Eksempel 192 ;6-[[2-(4-bromfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester ;ble erholdt ved omsetning av 6-[[4-amino-3-(fenylamino)fenyl]-oksy]heksansyremetylester med 4-brombenzoylklorid i henhold til den generelle arbeidsinstruks 5. ;MS (EI): 492/494 (molekyliontopper). ;Eksempel 193 ;6-[[2-[4-(trifluormetyl)fenyl]-1-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester ;ble erholdt ved omsetning av 6-[[4-amino-3-(fenylamino)fenyl]-oksy]heksansyremetylester med 4-(trifluormetyl)benzoylklorid i henhold til den generelle arbeidsinstruks 5. ;MS (EI): 482 (molekyliontopp). ;Eksempel 194 ;6-[[2-(4-fluorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre ;ble erholdt ved omsetning av 6-[[2-(4-fluorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester i henhold til den generelle arbeidsinstruks 9. ;MS (EI): 418 (molekyliontopp). ;Eksempel 195 ;6-[[l-fenyl-2-(benzotien-2-yl)-lH-benzimidazol-6-yl]oksy]-heksansyremetylester ;ble erholdt ved omsetning av 6-[[4-amino-3-(fenylamino)fenyl]-oksy]heksansyremetylester med benzotiofen-2-karbonsyreklorid i henhold til den generelle arbeidsinstruks 5. ;Smp. 129-130 °C. ;Eksempel 196 ;6-[[l-fenyl-2-(benzotien-2-yl)-lH-benzimidazol-6-yl]oksy]heksan-syre ;ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 340 °C (dekomp.). ;Eksempel 197 ;6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester ;Eksempel 198 ;6-[[6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyreisopropylester ;4,5-dimetoksy-l,2-dinitrobenzen ble i henhold til den ;.generelle arbeidsinstruks 1 hydrert til diaminoforbindelsen som ;i henhold til den generelle arbeidsinstruks 3 ble syklisert med trimetylortobenzoat tii 5,6-dimetoksy-2-fenyl-lH-benzimidazol (smp. 131-133 °C) . Dette benzimidazolderivat ble i henhold til den generelle arbeidsinstruks 14 omsatt med 4-metylfenylborsyre til 5,6-dimetoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol (smp. 145-148 °C) . Etter eterspaltning med bromhydrogensyre i henhold til den generelle arbeidsinstruks 6 til 5,6-dihydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol (<1>H-NMR til hydrobromidet (D6-DMSO): 5 = 2,42 ppm s (3H); 6,68 s (1H); 7,22 s (1H); 7,40-7,62 m (10H)) ble i henhold til den generelle arbeidsinstruks 8 alkyler^ing foretatt med 6-bromheksansyreisopropylester. Man erholdt 6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;smp. 137-139 °C ;og 6-[[6-hydroksy-l- (4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyreisopropylester ;smp. 177-178 °C. ;Eksempel 199 ;6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ;ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 245-248 °C. ;Eksempel 200 ;6-[[6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyre ;ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 182-184 °C. ;Eksempel 201 ;6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ;6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester ble metylert med metyljodid i henhold til den generelle arbeidsinstruks 8. ;Smp. 89-91 °C. ;Eksempel 202 ;6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ;ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 184-186 °C. ;Eksempel 203 ;6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester ;Eksempel 204 ;6-[[6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyremetylester ;ble fremstilt analogt med isopropylestrene ved alkylering av 5,6-dihydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol i henhold til den generelle arbeidsinstruks 8 med 6-bromheksansyremetylester. Man erholdt 6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester. ;<*>H-NMR (CDC13) : 5 = 1,45-1,58 ppm m (2H) ; 1, 65-1, 90 m (4H) ; 2,37 t (J = 7,5 Hz, 2H); 2,48 s (3H); 3,68 s (3H); 3,98 t (J = 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 (bred) (1H, OH); 6,62 s (1H); 7,18 d (J = 7.5 Hz, 2H); 5.68 s (broad) (1H, OH); 6.62 s (1H); 7.18 d (J =

8 Hz, 2H); 7,22-7,38 m (5H); 7,40 s (1H); 7,53 dd (J = 8, 1 Hz, 2H) 8Hz, 2H); 7.22-7.38 m (5H); 7.40 s (1H); 7.53 dd (J = 8, 1 Hz, 2H)

og 6-[[6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyremetylester. and 6-[[6-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester.

Smp. 141-143 °C. Temp. 141-143 °C.

Eksempel 205 Example 205

6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester 40 mg 6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble oppløst i 2 ml metanol, forsynt med 1 dråpe konsentrert svovelsyre og blandingen omrørt i 2 h. Man tilsatte mettet kaliumhydrogenkarbonatoppløsning, fortynnet med vann, ekstraherte med etylacetat, tørket ekstraktene over natriumsulfat og konsentrerte i vakuum. Resten ble krystallisert fra diisopropyleter. 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.

Smp. 81-82 °C. Temp. 81-82 °C.

Eksempel 206 Example 206

6-[[6-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]-oksy]heksansyremetylester 6-[[6-Methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]-oxy]hexanoic acid methyl ester

6-[[6-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyremetylester ble metylert med metyljodid i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 108-110 °C. Temp. 108-110 °C.

Eksempel 207 Example 207

6-[[6-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksansyre 6-[[6-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 182-184 °C. was produced in accordance with the general work instructions 9. Smp. 182-184 °C.

Eksempel 208 Example 208

6-[(5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

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

Til en suspensjon av 4 g 4,6-dinitro-3-fluprfenol (J. Org. Chem. 1991, 5958) i 100 ml etanol tilsatte man 6,6 g 3,4-dimetylanilin og omrørte i 7 d ved 40 °C. Etter avkjøling ble avsugning foretatt og resten rekrystallisert fra etanol. 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 (CDC13) : 5 = 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 (bred) (1H); 10,2-10,6 (1H). <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-dimetylfenyl)amino]-4,6-dinitrofenyl]oksy]heksan-syremetylester 5 g 3-[(3,4-dimetylfenyl)amino]-4,6-dinitrofenol ble 0-alkylert med 6-bromheksansyremetylester ved 70 °C analogt med den generelle arbeidsinstruks 8. 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 (CDCI3) : 5 = 1,45-1, 88 ppm m (6H); 2,30 s (6H); 2,33 t (J = 7,5 Hz, 2H); 3,68 s (3H); 3,88 t (J = 7,5 Hz, 2H); 6,45 s (1H); 7,00-7,08 m (2H); 7,25 d (J = 8 Hz, 1H); 9,03 s (1H); 9,89 s (bred) (1H). <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-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester c) 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

2,45 g 6-[[3-[(3,4-dimetylfenyl)amino]-4,6-dinitro-fenyl]oksy]heksansyremetylester ble hydrert i metanol i henhold til den generelle arbeidsinstruks 1. 500 mg av råproduktet ble omsatt med benzimidathydroklorid i henhold til den generelle arbeidsinstruks 4. Til forskjell fra den generelle arbeidsinstruks 4 ble råproduktet ikke vasket med vandig saltsyre etter at det var blitt tatt opp i løsningsmidlet. 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 (CDC13) : 5 = 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 t (J = 7,5 Hz, 2H); 3,67 s (3H); 3,93 t (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 og 2 Hz, 2H) . <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) .

Eksempel 209 Example 209

6-[[5-t[(4-klorfenyl)sulfonyl]amino]-1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester 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-l- (3, 4-dimetylf enyl) -2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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.

Smp. 186-191 °C. Temp. 186-191 °C.

Eksempel 210 Example 210

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

ble fremstilt med 6-[ (5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester. was prepared with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

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

Eksempel 211 Example 211

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

ble fremstilt analogt med 6-[(5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester. 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 (molekyliontopp). MS (EI): 489 (molecular ion peak).

Eksempel 212 Example 212

6-[[5-[[(4-klorfenyl)sulfonyl]amino]-2-(4-fluorfenyl)-1-(4-metoksyfenyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester 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-fluorfenyl)-1-(4-metoksyfenyl)-1H-benzimidazol-6-yl)oksy]heksansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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.

Smp. 180-182 °C. Temp. 180-182 °C.

Eksempel 213 Example 213

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

6-[(5-amino-l-(4-metoksyfenyl)-2-(4-metoksyfenyl)-1H-benzimidazol-6-yl)oksy]heksansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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.

Smp. 169-171 °C. Temp. 169-171 °C.

Eksempel 214 Example 214

4-[(5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]butansyremetylester 4-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]butanoic acid methyl ester

ble fremstilt analogt med 6-[(5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester. 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 (CDC13) : 5 = 2,17 ppm tt (J = 8 og 8 Hz, 2H); 2,52 t (J = 8 Hz, 2H); 3,68 s (3H); 3,90 s (3H); 3,98 t (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). <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).

Eksempel 215 Example 215

4-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]butansyremetylester 4-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester

4-[(5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]butansyremetylester ble omsatt med klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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 (molekyliontopp). MS (EI): 605 (molecular ion peak).

Eksempel 216 Example 216

5-[(5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]pentansyremetylester 5-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester

ble fremstilt analogt med 6-[(5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester. 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 (CDC13) : 5 = 1,78-1,89 ppm m (4H); 2,32 t (J = 8 Hz, 2H); 3,68 s (3H); 3,88 s (3H); 3,92 t (J = 7,5 Hz, 2H); 6,53 s (1H); 7,0 d (J = 12 Hz, 2H); 7,18-7,36 m (6H); 7,48-7,58 m (2H) . <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) .

Eksempel 217 Example 217

5- [[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester 5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester

5- [(5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6- yl)oksy]pentansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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 (molekyliontopp). MS (EI): 619 (molecular ion peak).

Eksempel 218 Example 218

6-[(5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl)-oksy]heksansyremetylester 6-[(5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl)-oxy]hexanoic acid methyl ester

ble fremstilt analogt med 6- [ (5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester. was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

Smp. 129-131 °C. Temp. 129-131 °C.

Eksempel 219 Example 219

6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6- [(5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. Smp. 168-170 °C. 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.

Eksempel 220 Example 220

6-[ [5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre 6-[ [5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 181-182 °C. was produced in accordance with the general work instructions 9. Smp. 181-182 °C.

Eksempel 221 Example 221

6-[(5-amino-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl)-oksy]heksansyremetylester 6-[(5-amino-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl)-oxy]hexanoic acid methyl ester

ble fremstilt analogt med 6-[(5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester. was prepared analogously with 6-[(5-amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester.

Smp. 105-107 °C. Temp. 105-107 °C.

Eksempel 222 Example 222

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

6-[(5-amino-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13-. 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-.

Smp. 189-191 °C. Temp. 189-191 °C.

Eksempel 223 Example 223

6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 102-105 °C. was produced in accordance with the general work instructions 9. Smp. 102-105 °C.

Eksempel 224 Example 224

5-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]pentansyre-metylester 5-[(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester

ble fremstilt analogt med 6-[(5-amino-l-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester. 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 (CDCI3) : 6 = 1, 82-1, 95 ppm m (4H) ; 2,39 t (J = 8 Hz, 2H) ; 3,69 s (3H); 3,92-4,00 m (2H); 6,60 s (1H); 7,26-7,34 m (6H); 7,43-7,58 m (5H). <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).

Eksempel 225 Example 225

5-[[5-[[(4-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester . 5-[(5-amino-l,2-difenyl-lH-benzimidazol-6-yl)oksy]-pentansyremetylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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.

Smp. 157-161 °C, Temp. 157-161 °C,

Eksempel 226 Example 226

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

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 236-242 _°C. was produced in accordance with the general work instructions 9. Smp. 236-242 _°C.

Eksempel 227 Example 227

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

6- [. (5-amino-l- (4-metoksyfenyl) -2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester ble omsatt med 4-fluorbenzensul-fonsyreklorid i henhold til den generelle arbeidsinstruks 13. MS (EI): 617 (molekyliontopp). 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).

Eksempel 228 Example 228

6-[[5-[[(4-(trifluormetylfenyl)sulfonyl]amino]-1-(4-metoksyfenyl) -2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester 6-[[5-[[(4-(trifluoromethylphenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

6-[(5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester ble omsatt med 4-(trifluormetyl)-benzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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 (molekyliontopp). MS (EI): 668 (molecular ion peak).

Eksempel 229 Example 229

6-[[5-[[(4-trifluorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lB-benzimidazol-6-yl]oksy]heksansyre 6-[[5-[[(4-trifluorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1B-benzimidazol-6-yl]oxy]hexanoic acid

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 190-192 °C. was produced in accordance with the general work instructions 9. Smp. 190-192 °C.

Eksempel 230 Example 230

6-[[5-[[(4-klorfenyl)sulfonyl]metylamino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester 6-[[5-[[(4-chlorophenyl)sulfonyl]methylamino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

100 mg 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre-metylester ble oppløst i 3 ml tetrahydrofuran. Til dette tilsatte man 10 mg hatriumhydrid ved 0 °C, lot omrøre i 30 min, tilsatte deretter 50 ul metyljodid dråpevis og lot omrøre i ytterligere 60 min ved 0 °C. Man tilsatte mettet ammoniumklorid-oppløsning, ekstraherte tre ganger med etylacetat, vasket de 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

organiske faser med vann, tørket over natriumsulfat og konsentrerte i vakuum. Resten kromatograferte man på silikagel. Smp. 178-180 °C. organic phases with water, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. Temp. 178-180 °C.

Eksempel 231 Example 231

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

100 mg 4-klor-N-(1,2-difenyl-lH-benzimidazol-5-yl)-benzensulfonamid ble suspendert i 0,5 ml N,N-dimetylformamid, forsynt med 8 mg natriumhydrid og omrørt i 30 min ved 20 °C. Man tilsatte 50 mg bromeddiksyremetylester, lot omrøre i 15 h, tilsatte vann, ekstraherte tre ganger med etylacetat, tørket ekstraktene over natriumsulfat, konsentrerte i vakuum og kromato-graf erte resten på silikagel. 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 (CDC13) : 5 = 3,70 ppm s (3H) ; 4,52 s (2H) ; 7,20 d (J = <1>H-NMR (CDCl3) : δ = 3.70 ppm s (3H); 4.52 s (2H); 7.20 d (J =

8 Hz, 1H); 7,26-7,58 m (14H); 7,70 d (J = 10 Hz, 2H). 8Hz, 1H); 7.26-7.58m (14H); 7.70 d (J = 10 Hz, 2H).

Eksempel 232 Example 232

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

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 248 °C. was produced in accordance with the general work instructions 9. Smp. 248 °C.

Eksempel 233 Example 233

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

100 mg 4-klor-N-(1,2-difenyl-lH-benzimidazol-5-yl)-benzensulfonamid ble suspendert i 0,5 ml N,N-dimetylformamid, forsynt med 6 mg natriumhydrid og omrørt i 30 min ved 20 °C. Man tilsatte 56 mg 4-bromsmøremetylester, lot omrøre i 15 h, tilsatte vann, ekstraherte tre ganger med etylacetat, tørket ekstraktene over natriumsulfat, konsentrerte i vakuum og utlutet resten med diisopropyleter. 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.

Smp. 54-58 °C. Temp. 54-58 °C.

Eksempel 234 Example 234

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

ble fremstilt i henhold til den generelle arbeidsinstruks 9. was produced in accordance with the general work instructions 9.

Smp. 24 9-254 °C. Temp. 24 9-254 °C.

Eksempel 235 Example 235

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

100 mg 4-klor-N-(1,2-difenyl-lH-benzimidazol-5-yl)-benzensulfonamid ble suspendert i 0,5 ml N,N-dimetylformamid, forsynt med 8 mg natriumhydrid og omrørt i 30 min ved 20 °C. Man tilsatte 60 mg 5-brompentansyremetylester, lot omrøre i 15 h, tilsatte vann, ekstraherte tre ganger med etylacetat, tørket ekstraktene over natriumsulfat, konsentrerte i vakuum og kroma-tograf erte resten på silikagel. 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.

^-NMR (CDC13) : 6 = 1,46-1,54 ppm m (2H) ; 1, 62-1,78 m (2H) ; 2,30 t (J = 8 Hz, 2H); 3,62 s (3H); 3,62 t (J = 8 Hz, 2H); 7,12-7,53 m (17H) . 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) .

Eksempel 236 Example 236

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

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 123-127 °C. was produced in accordance with the general work instructions 9. Smp. 123-127 °C.

Eksempel 237 Example 237

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

6-[[1,2-difenyl-lH-benzimidazol-5-yl]amino]heksansyre-metylester ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 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 (molekyliontopp). MS (EI): 588 (molecular ion peak).

Eksempel 238 Example 238

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

100 mg 4-klor-N-(1,2-difenyl-lH-benzimidazol-5-yl)-benzensulfonamid ble suspendert i 0,5 ml N,N-dimetylformamid, forsynt med 8 mg natriumhydrid og omrørt i 30 min ved 20 °C. Man tilsatte 70 mg 7-bromheptansyremetylester, lot omrøre i 15 h, forsynte med vann, ekstraherte tre ganger med etylacetat, tørket 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

ekstraktene over natriumsulfat, konsentrerte i vakuum og kroma-tograf erte resten på silikagel. the extracts over sodium sulfate, concentrated in vacuo and chromatographed the residue on silica gel.

<1>H-NMR (CDCI3) : 5 = 1,26-1, 64 ppm m (8H); 2,27 t (J = 8 Hz, 2H) ; 3,60 t (J = 8 Hz, 2H); 3,68 s (3H); 7,12 dd (J = 10, 2 Hz, 1H) ; 7,22 d (J = 10 Hz, 1H); 7,30-7,61 m (15H). <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).

Eksempel 239 Example 239

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

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 172-178 °C. was produced in accordance with the general work instructions 9. Smp. 172-178 °C.

Eksempel 240 Example 240

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

5-amino-l,2-difenyl-lH-benzimidazol ble omsatt med 4-fluorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 5-amino-1,2-diphenyl-1H-benzimidazole was reacted with 4-fluorobenzenesulfonic acid chloride according to the general work instructions 13.

Smp. 209-214 °C. Temp. 209-214 °C.

Eksempel 241 Example 241

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

150 mg N-(1,2-difenyl-lH-benzimidazol-5-yl)-4-fluor-benzensulf onamid ble suspendert i 0,5 ml N,N-dimetylformamid, forsynt med 12 mg natriumhydrid og omrørt i 30 min ved 20 °C. Man tilsatte 98 mg 6-bromheksansyremetylester, lot omrøre i 15 h, forsynte med vann, ekstraherte tre ganger med etylacetat, tørket ekstraktene over natriumsulfat, konsentrerte i vakuum og kroma-tograf erte resten på silikagel. 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.

Smp. 128-134 °C. Temp. 128-134 °C.

Eksempel 242 Example 242

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

ble fremstilt i henhold til den generelle arbeidsinstruks. 9. Smp. 200-210 °C. was produced in accordance with the general work instructions. 9. Smp. 200-210 °C.

Eksempel 243 Example 243

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

150 mg 4-(trifluormetyl)-N-(1,2-difenyl-lH-benzimidazol-5-yl)benzensulfonamid ble suspendert i 0,5 ml N,N-dimetyl-formamid, ble forsynt med 11 mg natriumhydrid og omrørt i 30 min ved 20 °C. Man tilsatte 88 mg 6-bromheksansyremetylester, lot omrøre i 15 h, forsynte med vann, ekstraherte tre ganger med etylacetat, tørket ekstraktene over natriumsulfat, konsentrerte i vakuum og utlutet resten med diisopropyleter. 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.

Smp. 159-161 °C. Temp. 159-161 °C.

Eksempel 244 Example 244

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

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 224-230 °C. was produced in accordance with the general work instructions 9. Smp. 224-230 °C.

Eksempel 245 Example 245

4-klor-N-[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-5-yl]-benzensulfonamid 4-chloro-N-[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-5-yl]-benzenesulfonamide

a) (2,4-dinitrofenyl)(4-metoksyfenyl)amin a) (2,4-dinitrophenyl)(4-methoxyphenyl)amine

1,43 g 4-(2,4-dinitroanilino)fenol, 500 mg kaliumkarbonat og 0,32 ml metyljodid ble omrørt i 2 d ved 20 °C i 5 ml N,N-dimetylformamid. Man helte blandingen på vann, ekstraherte tre ganger med etylacetat, tørket ekstraktene over natriumsulfat, konsentrerte i vakuum og kromatograferte resten på silikagel. 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.

Smp. 117-127 °C. Temp. 117-127 °C.

b) 5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol (2,4-dinitrofenyl)-4-metoksyfenylamin ble hydrert i b) 5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazole (2,4-dinitrophenyl)-4-methoxyphenylamine was hydrogenated in

henhold til den generelle arbeidsinstruks 1. Råproduktet ble syklisert med trimetylortobenzoat til benzimidazolderivatet ifølge i henhold til den generelle arbeidsinstruks 3. 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 (CDC13) : 6 = 3,88 ppm s (3H); 6,70 dd (J = 12, 2 Hz, 1H); 6,95-7,06 m (4H); 7,18-7,38 m (7H); 7,53-7,65 m (2H). <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-klor-N-[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-5-yl]-benzensulfonamid c) 4-chloro-N-[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-5-yl]-benzenesulfonamide

5-amino-l-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol ble omsatt med 4-klorbenzensulfonsyreklorid i henhold til den generelle arbeidsinstruks 13. 5-amino-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazole was reacted with 4-chlorobenzenesulfonic acid chloride according to the general work instructions 13.

Smp. 238-24 °C. Temp. 238-24 °C.

Eksempel 246 Example 246

6-[[(4-klorfenyl)sulfonyl][1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-5-yl] amino]heksansyremetylester 75 mg 4-klor-N-[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-5-yl]benzensulfonamid ble suspendert i 0,5 ml N,N-dimetylformamid, forsynt med 6 mg natriumhydrid og omrørt i 30 min ved 20 °C. Man tilsatte 44 mg 6-bromheksansyremetylester, lot omrøre i 15 h, forsynte med vann, ekstraherte tre ganger med etylacetat, tørket ekstraktene over natriumsulfat, konsentrerte i vakuum og kromatograferte resten på silikagel. 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 (molekyliontopp). MS (EI): 617 (molecular ion peak).

Eksempel 247 Example 247

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

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 205-208 °C. was produced in accordance with the general work instructions 9. Smp. 205-208 °C.

Eksempel 248 Example 248

2,2-dimetyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid 2,2-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

a) 2,2-dimetyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-nitril a) 2,2-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-nitrile

ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 6-brom-l,1-dimetylheksannitril i henhold til den generelle arbeidsinstruks 8. 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.

Smp. 115-118 °C. Temp. 115-118 °C.

b) 2,2-dimetyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid b) 2,2-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide

500 mg 2,2-dimetyl-6-[(1, 2-difenyl-lH-benzimidazol-6-yl)oksy]heksannitril ble oppvarmet i 2 h i.5 ml 80%-ig svovelsyre inntil tilbakeløp. Etter avkjøling'- ble oppløsningen for- 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

siktig helt over. på isvann, pH-verdien innstilt på pH 8 med natriumhydr.oksidoppløsning, ekstrahert tre ganger med etylacetat, ekstraktene tørket over natriumsulfat og konsentrert i vakuum. Resten ble kromatografert på silikagel. 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.

Smp. 115-118.°C. Temp. 115-118°C.

Eksempel 249 Example 249

8-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]oktansyremetylester ble erholdt ved omsetning av 1,2-difenyl-6-hydroksy-lH-benzimidazol med 8-bromoktansyremetylester i henhold til den generelle arbeidsinstruks 8. 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 .

Smp. 92-95 °C. Temp. 92-95 °C.

Eksempel 250 Example 250

8-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]oktansyre ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 136-140 °C. 8-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]octanoic acid was prepared according to general work instructions 9. M.p. 136-140 °C.

Eksempel 251 Example 251

6-[[1-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

ble fremstilt analogt med 6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester. was prepared analogously with 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Smp. 81-85 °C. Temp. 81-85 °C.

Eksempel 252 Example 252

6- t[I-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 17 6-180 °C. 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.

Eksempel 253 Example 253

7- t[I-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heptansyre-metylester 7- t[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]heptanoic acid methyl ester

ble fremstilt analogt med 6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester. was prepared analogously with 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Smp. 92-98 °C. Temp. 92-98 °C.

Eksempel 254 Example 254

7-[ [1-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heptansyre ble fremstilt i henhold til den generelle arbeidsinstruks 9. 7-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]heptanoic acid was prepared according to the general work instructions 9.

Smp. 175-178 °C. Temp. 175-178 °C.

Eksempel 255 Example 255

6- [ [1-(3-fluorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreme tyle s ter 6-[ [1-(3-fluorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

ble fremstilt analogt med 6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester. was prepared analogously with 6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Smp. 104-106 °C. Temp. 104-106 °C.

Eksempel 256 Example 256

6-[[1-(3-fluorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre 6-[[1-(3-fluorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble fremstilt i henhold til den generelle arbeidsinstruks 9. was produced in accordance with the general work instructions 9.

Smp. 149-151 °C. Temp. 149-151 °C.

Eksempel 257 Example 257

6-[[2-(4-nitrofenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

a) 6-metoksy-2-(4-nitrofenyl)-1-fenyl-lH-benzimidazol a) 6-Methoxy-2-(4-nitrophenyl)-1-phenyl-1H-benzimidazole

200 mg 4-metoksy-N<2->fenyl-o-fenylendiamin ble oppløst i 5 ml N,N-dimetylformamid, forsynt med 34 6 mg EEDQ og 234 mg 4-nitrobenzosyre og blandingen omrørt i 5 h ved 100 °C. Etter avkjøling ble vann tilsatt. Bunnfallet ble suget av og renset ved hjelp av søylekromatografi, tatt opp i 6 N saltsyre og oppvarmet i 2 h under tilbakeløp. Etter avkjøling ble oppløs-ningen dryppet inn i kaliumbikarbonatoppløsning. Bunnfallet ble suget av og tørket. 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.

Smp. 189-191 °C. b) 6-hydroksy-2-(4-nitrofenyl)-1-fenyl-lH-benzimidazol ble erholdt ved omsetning i henhold til den generelle arbeidsinstruks 6. 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): 5 = 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); 9,55 s (bred)(1H). <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-nitrofenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester c) 6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

ble erholdt ved omsetning i henhold til den generelle arbeidsinstruks 8. was obtained by turnover in accordance with the general work instructions 8.

<1>H-NMR (CDC13) : 6 = 1,45-1,55 ppm m (2H); 1, 62-1,84 m (4H); 2,33 t (J = 8 Hz, 2H); 3,68 s (3H) ; 3,95 t (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). <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).

Eksempel 258 Example 258

6-[[2-(4-nitrofenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre 6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid

ble fremstilt i henhold til den generelle arbeidsinstruks 9. Smp. 181-186 °C. was produced in accordance with the general work instructions 9. Smp. 181-186 °C.

Eksempel 259 Example 259

6-[[l-fenyl-2-(3-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester 6-[[1-phenyl-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexane acid methyl ester

ble fremstilt analogt med 6-[[l-fenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oksy]heksansyremetylester. was prepared analogously with 6-[[l-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.

Smp. 159-160 °C. Temp. 159-160 °C.

Eksempel 260 Example 260

N-(syklopropylmetoksy)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)-oksy]heksanamid N-(cyclopropylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)-oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. was produced in accordance with the general work instructions 18.

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

Eksempel 261 Example 261

N-isobutoksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid N-isobutoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexane-amide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. was produced in accordance with the general work instructions 18.

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

Eksempel 262 Example 262

N-( fenylmetoksy)- 6-[ 2- fenyl- l-( 3, 4, 5- trimetoksyfenyl)- 1H-benzimidazol- 6- yl) oksy] heksanamid N-(phenylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide

Til en oppløsning av 17 mg karbonyldiimidazol i 1 ml tetrahydrofuran tilsatte man en oppløsning av 50 mg 6-[2-fenyl-1-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl)oksy]heksansyre i 1 ml tetrahydrofuran, omrørte i 30 minutter ved 20 °C og oppvarmet i 30 minutter inntil tilbakeløp. Ved 20 °C tilsatte man 16 mg O-benzylhydroksylaminhydroklorid og lot omrøre i 20 h. For opparbeidelse tilsatte man etylacetat, ekstraherte med 2 N saltsyre og mettet natriumbikarbonatoppløsning, tørket over natriumsulfat og konsentrerte i vakuum. Resten ble renset ved hjelp av søylekromatografi på silikagel. 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.

Smp. 145-148 °C. Temp. 145-148 °C.

Eksempel 263 Example 263

N- (syklopropylmetoksy)-6-[2-fenyl-l-(3,4,5-trimetoksyfenyl)-1H-benzimidazol-6-yl)oksy]heksanamid N-(cyclopropylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide

ble fremstilt, analogt med N-(fenylmetoksy)-6-[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl)oksy]heksanamid. was prepared, analogously to N-(phenylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide.

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

Eksempel 264 Example 264

N-isobutoksy-6-[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl)oksy]heksanamid N-isobutoxy-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide

ble fremstilt analogt med N-(fenylmetoksy)-6-[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl)oksy]heksanamid. was prepared analogously with N-(phenylmethoxy)-6-[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl)oxy]hexanamide.

<1>H-NMR (CDCI3) : 5 = 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 (bred)(1H). <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).

Eksempel 265 Example 265

N-isopropyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid ble fremstilt i henhold til den generelle arbeidsinstruks 17. Smp. 107-112 °C. 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.

Eksempel 266 Example 266

N,N-dimetyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid ble fremstilt i henhold til den generelle arbeidsinstruks 17. Smp. 83-88 °C. 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.

Eksempel 267 Example 267

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-pyrrolidin-l-ylheksan-l-on 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-pyrrolidin-1-ylhexan-1-one

ble fremstilt i henhold til den generelle arbeidsinstruks 17. Smp. 84-88 °C. was produced in accordance with the general work instructions 17. Smp. 84-88 °C.

Eksempel 268 Example 268

N- (2-metoksyetyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid N-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 17. Smp. 63-68 °C. was produced in accordance with the general work instructions 17. Smp. 63-68 °C.

Eksempel 269 Example 269

N- (3-metoksypropyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid N-(3-methoxypropyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 84-91 °C. was prepared in accordance with the general work instructions 18. Smp. 84-91 °C.

Eksempel 270 Example 270

N-isobutyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid ble fremstilt i henhold til den generelle arbeidsinstruks 17. <X>H-NMR (CDC13) : 5 = 0,90 ppm d (J = 8 Hz, 6H) ; 1, 44-1,57 m (2H) ; 1,65-1,85 m (5H); 2,20 t (J = 8 Hz, 2H); 3,08 t (J = 8 Hz, 2H); 3,94 t (J = 8 Hz, 2H); 6,68 d (J = 2 Hz, 1H); 6,96 dd (J = 10, 2 Hz, 1H); 7,25-7,38 m (5H); 7,45-7,58 m (5H); 7,75 d (J = 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). 10 Hz, 1H).

Eksempel 271 Example 271

N-[(2,2-dimetylamino)etyl]-N-metyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid N-[(2,2-dimethylamino)ethyl]-N-methyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 17. <1>H-NMR (CDCI3) (signaler fra hovedrotameren): 5 = 1,44-1,57 ppm m (2H); 1,64-1,84 m (4H); 2,30 s (6H); 2,34 t (J = 8 Hz, 2H); 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 t (J = 8 Hz, 2H); 3,00 s (3H); 3,50 t (J = 8 Hz, 2H); 3,94 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). 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).

Eksempel 272 Example 272

N-(2-metoksyetyl)-N-metyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid N-(2-methoxyethyl)-N-methyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 17. <1>H-NMR (CDC13) (signaler fra hovedrotameren): 5 = 1,43-1,58 ppm m (2H); 1, 63-1,84 m (4H); 2,33 t (J = 8 Hz, 2H); 3,07 s (3H) ; 3,32 s (3H); 3,47-3,58 m (4H) ; 3,95 t (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). 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).

Eksempel 273 Example 273

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-morfolin-l-yl-heksan-l-on 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-morpholin-1-yl-hexan-1-one

ble fremstilt i henhold til den generelle arbeidsinstruks 17. <1>H-NMR (CDCI3) : 6 = 1, 47-1,59 ppm m (2H) ; 1, 63-1,88 m (4H) ; 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 t (J = 8 Hz, 2H); 3,42-3,49 m (2H); 3,57-3,70 m (6H); 3,94 t (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). 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).

Eksempel 274 Example 274

N,N-di-(2-metoksyetyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)-oksy]heksanamid N,N-di-(2-methoxyethyl)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)-oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 88-98 °C. was prepared in accordance with the general work instructions 18. Smp. 88-98 °C.

Eksempel 275 Example 275

N-isopentyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 127-129 °C. 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.

Eksempel 276 Example 276

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

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp, 120-124 °C. ' was prepared according to the general work instructions 18. Mp, 120-124 °C. '

Eksempel 277 Example 277

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

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 154 °C. was prepared in accordance with the general work instructions 18. Smp. 154 °C.

Eksempel 278 Example 278

6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-piperidin-1-ylheksan-l-on 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-piperidin-1-ylhexan-1-one

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 93-98. °C. was prepared in accordance with the general work instructions 18. Smp. 93-98. °C.

Eksempel 279 Example 279

[6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-l-heksanoyl]piperidin-4-karbonamid [6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-hexanoyl]piperidine-4-carbonamide

ble fremstilt i henhold til den generelle arbeidsinstruks 17. Smp. 177-178 °C. was produced in accordance with the general work instructions 17. Smp. 177-178 °C.

Eksempel 280 Example 280

[[6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-heksanoyl]metyl-amino] eddiksyreetylester [[6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-hexanoyl]methyl-amino] acetic acid ethyl ester

ble fremstilt i henhold til den generelle arbeidsinstruks 17. <X>H-NMR (CDC13) (signaler fra hovedrotameren): 5 = 1,23 ppm t (J = 8 Hz, 3H); 1,45-1,88 m (6H); 2,40 t (J = 8 Hz, 2H); 3,08 s (3H); 3,93 t (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); 7,45-7,58 m (5H); 7,75 d (J = 10 Hz, 1H). 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).

Eksempel 281 Example 281

4-[[6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-heksanoyl]]-piperazin-1-karbonsyreetyles ter 4-[[6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-hexanoyl]]-piperazine-1-carboxylic acid ethyl ester

ble fremstilt i henhold til den generelle arbeidsinstruks 17. <X>H-NMR (CDCI3) : 6 = 1,27 ppm t (J = 8 Hz, 3H); 1,45-1, 60 m (2H); 1,63-1,88 m (4H); 2,36 t (J = 8 Hz, 2H); 3,40-3,53 m (6H); 3,56-3,64 m (2H) ; 3,93 t (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) . 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) .

Eksempel 282 Example 282

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

ble fremstilt i henhold til den generelle arbeidsinstruks 18. was produced in accordance with the general work instructions 18.

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

Eksempel 283 Example 283

N,N-dimetyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N,N-dimethyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. was produced in accordance with the general work instructions 18.

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

Eksempel 284 Example 284

N,N-dietyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N,N-diethyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. was produced in accordance with the general work instructions 18.

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

Eksempel 285 Example 285

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

ble fremstilt i henhold til den generelle arbeidsinstruks 18. <1>H-NMR (CDC13) : 5 = 0,90 ppm d (J = 8 Hz, 6H) ; 1, 44-1,55 m (2H) ; 1,58-1,83 m (5H); 2,20 t (J = 8 Hz, 2H); 2,30 s (3H); 2,35 s (3H); 3,09 t (J = 8 Hz, 2H); 3,94 t (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 og 2 Hz, 2H); 7,73 d (J = 10 Hz, 1H). 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).

Eksempel 286 Example 286

N-syklopropyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N-cyclopropyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. was produced in accordance with the general work instructions 18.

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

Eksempel 287 Example 287

N-syklobutyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N-cyclobutyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til dé-n' generelle arbeidsinstruks 18. was produced in accordance with dé-n' general work instructions 18.

1H-NMR (CDCI3) : 6 = 1, 42-1, 55 ppm m (2H); 1, 60-1,88 m (8H); 2,15 t (J = 8 Hz, 2H); 2,28-2,40 m (2H); 2,30 s (3H); 2,35 s (3H) ; 3,93 t (J = 8 Hz, 2H); 4,40 kvintett (J = 8 Hz, 2H); 5,55 s (bred) (1H); 6,63 d (J = 2 Hz, 1H); 6,92 dd (J = 10, 2 Hz, 1H) ; 7,03 dd (J = 10 Hz og 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) . 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) .

Eksempel 288 Example 288

N-tert.-butyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl] oksy] heksanamid N-tert-butyl-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. <1>H-NMR (CDCI3) : 6 = 1,32 ppm s (9H); 1,42-1,55 m (2H); 1,62-1,82 m (4H); 2,10 t (J = 8 Hz, 2H); 2,30 s (3H); 2,36 s (3H) ; 3,92 t . 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 (bred) (1H); 6,66 d (J = 2 Hz, 1H) ; 6,93 dd (J = 10, 2 Hz, 1H); 7,02 dd (J = 10 Hz og 2 Hz, 1H); 7,09 s (bred)(lH); 7,22-7,36 m (4H); 7,56 dd (J = 8, 2 Hz, 2H); 7,73 d (J = 10 Hz, 1H). (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).

Eksempel 289 Example 289

(R)-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-1-(2-metoksymetyl)pyrrolidin-l-ylheksan-l-on (R)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-1-(2-methoxymethyl)pyrrolidin-1-ylhexan-1-one

ble fremstilt i henhold til den generelle arbeidsinstruks 18. was produced in accordance with the general work instructions 18.

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

Eksempel 290 Example 290

N-(3-imidazol-l-yl-propyl)-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N-(3-imidazol-1-yl-propyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. <1>H-NMR (CDCI3) : 5 = 1, 42-1,53 ppm m (2H); 1, 62-2, 02 m (6H); 2,17 t (J = 8 Hz, 2H); 2,27 s (3H) ; 2,34 s (3H); 3,24 q (J = 8 Hz, 2H); 3,92 t (J = 8 Hz, 2H); 3,96 t (J = 8 Hz, 2H); 5,68 s (bred)(lH); 6,63 d (J = 2 Hz, 1H); 6,88-6,95 m (2H); 7,00 dd (J = 10 Hz og 2 Hz, 1H); 7,04-7,10 m (2H); 7,20-7,36 m (4H); 7,50 s (bred)(lH); 7,53 dd (J = 8, 2 Hz, 2H); 7,72 d (J = 10 Hz, 1H). 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).

Eksempel 291 Example 291

N- (2-pyridin-2-yletyl)-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N-(2-pyridin-2-ylethyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble. fremstilt i henhold til den generelle arbeidsinstruks 18. • became. produced in accordance with the general work instructions 18. •

<X>H-NMR (CDCI3) : 6 = 1,38-1,52 ppm m (2H) ; 1, 62-1,82 m (4H); 2,15 t (J = 8 Hz, 2H); 2,30 s (3H); 2,35 s (3H); 2,96 t (J = 8 Hz, 2H); 3,66 q (J = 8 Hz, 2H); 3,90 t (J = 8 Hz, 2H); 6,48 s (bred)(1H); 6,65 d (J = 2 Hz, 1H); 6,92 dd (J = 10, 2 Hz, 1H); 7,00 dd (J = 10 Hz og 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 (bred)(J = 6 Hz, 1H). <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).

Eksempel 292 Example 292

N,N-dimetyl-6-[[2-(4-nitrofenyl)-l-fenyl-lH-benzimidazol-6-y1]oksy]heksanamid N,N-dimethyl-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. <1>H-NMR (CDCI3) : 6 = 1,46-1,58 ppm m (2H) ; 1, 64-1, 88 m (4H); 2,32 t (J = 8 Hz, 2H); 2,93 s (3H); 3,00 s (3H); 3,96 t (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) . 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) .

Eksempel 293 Example 293

N-isopropyl-6r[[2-(4-nitrofenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N-isopropyl-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 162-165 °C. was prepared in accordance with the general work instructions 18. Smp. 162-165 °C.

Eksempel 294 Example 294

N-isopentyl-6-[[2-(4-nitrofenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N-isopentyl-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 148-154 °C. was prepared in accordance with the general work instructions 18. Smp. 148-154 °C.

Eksempel 295 Example 295

N- (3-metoksypropyl)-6-[[2-(4-nitrofenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid N-(3-methoxypropyl)-6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks 18. Smp. 104-110 °C. was prepared in accordance with the general work instructions 18. Smp. 104-110 °C.

Eksempel 296 Example 296

N-(3-metoksypropyl)-6-[[1-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl] oksy] heksanamid N-(3-methoxypropyl)-6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide

ble fremstilt i henhold til den generelle arbeidsinstruks.18. was produced in accordance with the general work instructions.18.

^-NMR (CDCI3) : 5 = 1, 43-1,56 ppm m (2H) ; 1, 62-1,85 m (6H) ; 2,10-2,23 m (4H); 2,95 t (J = 10 Hz, 2H); 3,00 t (J = 10 Hz, 2H) ; 3,32 s (3H); 3,32-3,40 m (2H); 3,48 t (J = 8 Hz, 2H); 3,93 t (J = 8 Hz, 2H); 6,03 s (bred)(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 (bred)(1H); 7,26-7,35 m (4H); 7,55 dd (J = 10 Hz, 2H); 7,72 d (J = 8 Hz, 1H). 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).

Eksempel 297 Example 297

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

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 3-pyridylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 429 (molecular ion peak).

Eksempel 298 Example 298

6-[[1-(4-metylfenyl)-2-(4-pyridyl)-lH-benzimidazol-6-yl]oksy]-heksansyrenre tyle s ter 6-[[1-(4-methylphenyl)-2-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid ethyl ester

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 4-pyridylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 429 (molecular ion peak).

Eksempel 299 Example 299

6-[[1-(4-metylfenyl)-2-(2-tienyl)-lH-benzimidazol-6-yl]oksy]-heksansyremetyles ter 6-[[1-(4-methylphenyl)-2-(2-thienyl)-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 2-tienylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 434 (molecular ion peak).

Eksempel 300 Example 300

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

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 3-tienylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 434 (molecular ion peak).

Eksempel 301 Example 301

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

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 3-indolylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 4 67 (molecular ion peak).

Eksempel 302 Example 302

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

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl] oksy]heksansyremetylester med 2-furylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 418 (molecular ion peak).

Eksempel 303 Example 303

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

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl] oksy]heksansyremetylester med 3-furylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 418 (molecular ion peak).

Eksempel 304 Example 304

6-[[1-(4-metylfenyl)-2-(5-metyl-2-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester 6-[[1-(4-methylphenyl)-2-(5-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 5-metyl-2-tienylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 448 (molecular ion peak).

Eksempel 305 Example 305

6-[[1-(4-metylfenyl)-2-(4-brom-2-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester 6-[[1-(4-methylphenyl)-2-(4-bromo-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 4-brom-2-tienylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliqntopper). MS' (ÉI):•512/514 (molecular peaks).

Eksempel 306 Example 306

6-[[1-(4-metylfenyl)-2-(3-metyl-2-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester 6-[[1-(4-methylphenyl)-2-(3-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

ble erholdt ved omsetning av 6-[[4-amino-3-((4-metylfenyl)-amino)fenyl]oksy]heksansyremetylester med 3-metyl-2-tienylkarbaldehyd i henhold til den generelle arbeidsinstruks 16. 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 (molekyliontopp). MS (EI): 448 (molecular ion peak).

Eksempel 307 Example 307

Hemming av mikrogliaaktiveringen Inhibition of microglial activation

For fremstilling in vitro av A(5-aktiverte mikroglia blir primære rottemikroglia inkubert med syntetisk A(3-peptld: For å simulere A(J-avléiringer blir syntetisk A(3-peptid tørket inn på 96-hulls vevskulturplater. For dette blir en peptidstamoppløsning av 2 mg/ml H20 1:50 fortynnet i H2O. For belegning av 96-hullsplatene blir 30 ul av denne fortynnede peptidoppløsning anvendt pr. hull og tørket inn over natten ved romtemperatur. 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.

Primære rottemikroglia blir høstet fra blandede gliakulturer som ble utvunnet fra P3-rottehjerner. For fremstilling av blandede gliakulturer blir hjernene til 3 dager gamle rotter tatt ut og befridd for hjernehud. Enkeltvise celler ble oppnådd ved hjelp av trypsinering (0,25% trypsinoppløsning, 15 minutter 37 °C). Etter fraskillelse av ikke-fordøyde vevsfragmenter ved hjelp av et 40 um nylonnett blir de isolerte celler avsentri-fugert (800 opm/10 minutter). Cellepelleten ble på ny suspendert i dyrkningsmedium og overført til 100 ml vevskulturflasker. 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 hjerne/vevskulturflaske). Dyrkningen av cellene fant sted over et tidsrom på 5-7 dåger i Dulbeccos modfiserte Eagles medium (DMEM, med glutamin), supplert med penicillin (50 U/ml), streptomycin (40 ug/ml), og 10% (v/v) føtalt kalveserum (FCS) ved 37 °C og 5% CO2. I løpet av denne inkubasjon dannes en adhesiv celleplen som hovedsakelig består av astrocytter. Mikroglia forplanter seg som ikke- eller svakt-adhesive celler på denne og blir høstet via risteinkubasjon (420 omdreininger/minutt, (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 time). 1 hour).

For aktivering av mikrogliaene ved hjelp av A(5-peptid blir 2,5 ganger 104 mikroglia/hull sådd på Ap-belagte vevskulturplater og i løpet av et tidsrom på 7 dager inkubert i DMEM (med glutamin), supplert med penicillin (50 U/ml), streptomycin (40 ug/ml) og 10% (v/v) føtalt kalveserum (FCS) ved 37 °C og 5% C02. På dag 5 fant tilførsel av en forbindelse ifølge oppfinnelsen i forskjellige konsentrasjoner (0,1, 0,3, 1,3 og 10 uM) sted. 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 kvantifisering av mikrogliareaktiviteten blir på dyrkningsdag 7 den metabolske aktivitet målt via reduksjonen av MTS (3-(4,5-dimetyltiazol-2-yl)-5-(3-karboksymetoksyfenyl)-2-(sulfofenyl)-2H-tetrazolium), Owen's Reagenz, Baltrop, J.A. et al., Bioorg. & Med. Chem. Lett. 1, 6111 (1991)). Den prosentu-élle hemming relaterer seg til bare én kontroll behandlet med DMSO. Forbindelsene ifølge oppfinnelsen hemmer mikrogliaaktiveringen . 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.

Eksempel 308 Example 308

Cerebralt hjerneinfarkt hos rotter (MCAO-modell) Cerebral infarction in rats (MCAO model)

Forbindelsene ifølge oppfinnelsen ble ved et dyreforsøk testet for cerebral iskemi (slaganfall), MCAO-modellen ("perman-ent middle cerebral artery occlusion"), for in vivo-aktivitet. ■ Ved ensidig stengning av den midlere hjernearterie (MCA) blir et hjerneinfarkt utløst som beror på underforsyning av det tilsvarende hjerneområde med oksygen og næringsstoffer. Følgene av denne underforsyning er en utpreget celleundergang så vel som, påfølgende, en sterk mikrogliaaktivering. Denne mikrogliaaktivering når riktignok først etter flere dager sitt maksimum og kan holde på i flere uker. For testing av stoffene ble forbindelsene ifølge oppfinnelsen administrert intraperitonealt 1-6 dager etter okklusjon. Dyrene ble perfundert på dag 7 og avlivet. Omfanget av mikrogliaaktiveringen ble målt ved hjelp av en modifisert immunhistokjemisk metode. For dette ble vibratom-snitt av fikserte hjerner inkubert med antistoffer som kjenner igjen CR3-komplementreseptoren hhv. MHCII-komplekset på akti-verte mikroglia. Kvantifiseringen av den primære antistoffbind-ing fant sted ved hjelp av et enzymkoblet deteksjonssystem. Behandlingen med forbindelsene ifølge oppfinnelsen førte til en signifikant reduksjon av mikrogliaaktiveringen i den hjernehalv-del som var utsatt for hjerneinfarkt. Reduksjonen utgjorde minst 20%. 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%.

Eksempel 309 Example 309

Aktivering av makrofager Activation of macrophages

For å teste stoffene på makrofager/monocytter ble LPS-aktiverte THP-l-celler anvendt. For dette ble 2,5 x 106 celler/ml sådd ut i RPMI-medium (RPMI 1640 + 10% FCS). Forbindelsene ifølge oppfinnelsen ble tilført i en konsentrasjon på 5 uM og forhåndsinkubert i 30 minutter. Stimuleringen av cellene fant sted over natten ved 37 °C med 1 jag/ml LPS. Deretter ble mediet høstet og TNFa-mengden bestemt kvantitativt. Behandlingen av cellene med stoffene ifølge oppfinnelsen førte til en reduksjon av TNFa-mengden på minst 30%. 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. Benzimidazoler, karakterisert ved generell formel: hvori R<1> betyr en fenyl-, naftyl-, fluorenyl-, indanyl-, pyridyl-, tienyl-, furyl-, indolyl- eller benzotienylgruppe som kan være substituert med inntil tre av de følgende substituenter uavhengig av hverandre: F, Cl, Br, I, XOH, XOR4, XCN, XSR4, N02, XNH2, XNHR<4>, XNR<4>R4', R<4>, hvorved to substituenter på R<1>, dersom de står i ortostilling til hverandre, kan være slik forbundet med hverandre at de sammen danner metandiylbisoksy, etan-1,2-diylbisoksy, propan-1,3-diyl, butan-1,4-diyl, R2 har samme betydning som R<1>, R3 betyr én eller to substituenter som uavhengig av hverandre kan være: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, N02, XNH2, XNHR4, XNR<4>R<4>', XNHS02R<4> eller R<4>, R4 og R<4>' betyr uavhengig av hverandre Ci-4-perfluor-alkyl,' Ci-6-alkyl, fenyl eller fenyl-Ci-C4-alkyl, hvorved fenyl-gruppene kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3 eller C2F5, R5 og R<5>' betyr uavhengig av hverandre Ci_6-alkyl, hvorved et karbonatom kan være utvekslet mot Q, S, SO, S02, NH, NCi-3--alkyl eller• NCi-3-alkanoyl, C3-7-syklpalkyl-Co-3Talkyl, hvorved i en 5-leddet sykloalkylring et ringledd kan være et N eller et 0 og i en 6- eller 7-leddet sykloalkylring ett eller to ringledd kan være N og/eller 0, hvorved ringnitrogener eventuelt kan være substituert med Ci_3-alkyl eller Ci-3-alkanoyl, fenyl, fenyl-Ci-C4-alkyl, pyridyl, pyridyl-Ci-C4-alkyl eller imidazolyl-Ci-C4-alkyl, hvorved alle tidligere nevnte alkylrester kan være substituert med inntil to substituenter av 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 og alle tidligere nevnte fenyl- og pyridylgrupper kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2H5, N02, OCH3, 0C2H5, CF3, C2F5, eller R<5> og R<5>' danner sammen med nitrogenatomet en 7-pyrrolidin-, morfolin-, piperidin- eller piperazinring og kan være substituert med Ci-4-alkyl, Ci-4-alkoksy-Co-2-alkyl, Ci_4-alkoksykarbonyl eller aminokarbonyl, A betyr Ci_i0-alkandiyl eller C2_i0-alkendiyl, B betyr COOH, COOR<5>, C0NH2, C0NHNH2, CONHR<5>, CONR<5>R<5>', CONHOH, CONHOR<5>, S02NH2, S02NHR<5>, S02NR<5>R<5>', X betyr en binding, Y betyr 0, NH, NR<4>, NS02R<4>, hvorved de følgende forbindelser er utelukket: [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyremetylester, 5-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]pentansyremetylester,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-difenyl-lH-benzimidazol-6-yl)oksy]butansyreetylester,4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5- [[1-(4-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester,5- [[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [ [1- (4-nitrofenyl) -2-fenyl-lH-benzimidazol-6-yl] oksy].heksan-syremetylester, 5-[[1-(4-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester,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-klorfenyl)sulfonyl]amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester, 5-[[1-[4-[(acetyl)amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester,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-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester,5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 5-[[1-(3-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5-[[1-[3-[[(4-klorfenyl)sulfonyl]amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy] pentansyremetylester, 5-[[1-[3-[(acetyl)amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester.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. Benzimidazoler ifølge krav 1, karakterisert ved at de er valgt fra: [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyreisopropylester,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-difenyl-lH-benzimidazol-6-yl)oksy]propansyremetylester, 2-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]propansyremetylester,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-difenyl-lH-benzimidazol-6-yl)oksy]butansyreisopropyl-ester,4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid isopropyl ester, 5- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]pentansyreisopropyl-ester,5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid isopropyl ester, 6- [(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyremetylester, 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksansyreisopropyl-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-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid, N-metoksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid, N-(fenylmetoksy)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-hydroksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid,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-difenyl-lH-benzimidazol-6-yl)oksy]heptansyremetylester, 6-[[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[2-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[2-fenyl-l-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(3-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syre, ■ 6-[[1-(4-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan- -syremetylester, 6-[[1-(4-cyanfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(3-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester 6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-klorfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester,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-metylfenyl) -2-fenyl-lH-.benzimidazol-6-yl] oksy] heksan-syrernetylester, 6-[[1-(3-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[1-(3,5-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[1-(3,5-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyreisopropylester, 6-[[1-(3-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(3,4-dimetoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-heksansyremetylester,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- (metylendioksy)fenyl]-2-fenyl-lH-benzimidazol-6-yl] oksy]heksansyremetylester, 6-[[1-[3,4-(metylendioksy)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre,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-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyremetylester,6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]-oxy]hexanoic acid methyl ester, 6- [ [2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyre, 6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[1-[4-(N,N-dimetylamino)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[1-[4-(N,N-dimetylamino)fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre, 6-[[l-fenyl-2-[3-(trifluormetyl)fenyl]-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(3-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[2-(4-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-klorfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreisopropylester, 6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-metylfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-■ syreisopropylester, 6-[[l-fenyl-2-(4-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[(1,2-difenyl-5-nitro-lH-benzimidazol-6-yl)oksy]heksan-syremetylester, 6-[(1,2-difenyl-5-nitro-lH-benzimidazol-6-yl)oksy]heksansyre-isopropylester, 6-[[5-[[(4-bromfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1, 2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1, 2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[1,2-difenyl-5-[[(3-metylfenyl)sulfonyl]amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[1,2-difenyl-5-[[(4-metylfenyl)sulfonyl]amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester,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- [ [l,.2-difenyl-5- [ [ (4-metoksyfenyl) sulfonyl] amino] -lH-benzimidazol-6-yl]oksy]heksansyreisopropylester,6-[[1,2-diphenyl-5-[[(4-methoxyphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester, 6- [ [1,2-difenyl-5-[[[(4-trifluormetyl)fenyl]sulfonyl]amino]-1H-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[5-[[[4-(acetylamino)fenyl]sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[5-[[bis-(3-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[1,2-difenyl-5-[(propylsulfonyl)amino]-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester, 6-[[5-[(benzylsulfonyl)amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]heksansyreisopropylester,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-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]eddiksyre-metylester,2-[2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid methyl ester, 3- [2-[(1, 2-difenyl-lH-benzimidazol-6-yl)oksy]etoksy]propan-syremetylester, 6-[[1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syreetylester, 6-[[4-acetyl-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-5-yl]oksy]heksan-syremetylester, 6-[[2-fenyl-l-[4-(tiometyl)fenyl]-lH-benzimidazol-5-yl]oksy]-heksansyremetylester, 6-[[2-fenyl-l-[(4-tiometyl)fenyl]-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[2-fenyl-l-(3-tienyl)-lH-benzimidazol-5-yl]oksy]heksan-syremetylester, 6-[[2-fenyl-l-(3-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester,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-difenyl-lH-benzimidazol-6-yl)oksy]butansyremetylester, N-(fenylmetoksy)-6-[[2-fenyl-l-(3,4,5-trimetoksyfenyl)-1H-benzimidazol-6-yl]oksy]heksanamid, N,N-dimetyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, N-isopropyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-pyrrolidin-l-ylheksan-l-on,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-klorfenyl) sulfonyl] amino] -1, 2-difenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[4-(acetyloksy)-1-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[4-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[4-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre,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--metyl-l- (4-metylfenyl) -2-fenyl-lH-benzimidazol-6-yl] oksy] - heksansyremetylester.6-[[7--methyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester. 3. Benzimidazoler ifølge krav 1, karakterisert ved at de er valgt fra:3. Benzimidazoles according to claim 1, characterized in that they are selected from: 6- [ [2-fenyl-l- (3-pyridyl) -lH-ben.zimidazol-5-yl] oksy] heksan-syremetylester, 6-[[2-fenyl-l-(3-pyridyl)-lH-benzimidazol-6-yl]oksy]heksansyre-metylester, 6-[[2-fenyl-l-(4-pyridyl)-lH-benzimidazol-6-yI]oksy]heksansyre-metylester, 6-[[2-(4-fluorfenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-metoksyfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-(4-bromfenyl)-1-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[2-[4-(trifluormetyl)fenyl]-1-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[l-fenyl-2-(benzotien-2-yl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[l-fenyl-2-(benzotien-2-yl)-lH-benzimidazol-6-yl]oksy]heksan-syre, 6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyreisopropylester, 6-[[5-hydroksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyre, 6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy] heksansyreisopropylester, 6-[[5-hydroksy-l- (4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[5-metoksy-l-(4-metylfenyl)-2-fenyl-lH-benzimidazol-6-yl]-oksy]heksansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-2-(4-fluorfenyl)-1-(4-metoksyfenyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-(4-metoksyfenyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester,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-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]butansyremetylester,4- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester, 5- [[5-[[(4-klorfenyl)sulfonyl]amino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester,5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5- [[5-[[(4-klorfenyl)sulfonyl]amino]-1,2-difenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester,5- [[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [[5-[[(4-(trifluormetyl)fenyl)sulfonyl]amino]-1-(4-metoksyfenyl) -2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[5-[[(4-klorfenyl)sulfonyl]metylamino]-1-(4-metoksyfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[1-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[1-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksansyre, 6-[[1-(3-fluorfenyl)-2^fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester , 6-[[2-(4-nitrofenyl)-l-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 6-[[l-fenyl-2-(3-pyridinyl)-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, N-(syklopropylmetoksy)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)-oksy]heksanamid, N-isobutoksy-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, N-(syklopropylmetoksy)-6-[2-fenyl-l-(3,4,5-trimetoksyfenyl)-1H-benzimidazol-6-yl)oksy]heksanamid, N-isobutoksy-6-[2-fenyl-l-(3,4,5-trimetoksyfenyl)-lH-benzimidazol-6-yl)oksy]heksanamid, N-(2-metoksyetyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-(3-metoksypropyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-isobutyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksanamid, 6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-1-morfolin-l-yl-heksan-l-on, N,N-di-(2-metoksyetyl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)-oksy]heksanamid, N-isopentyl-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]heksan-amid, N-(pyridin-2-yl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-(pyridin-3-yl)-6-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]-heksanamid, N-isopropyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N,N-dimetyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N,N-dietyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-isobutyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-syklopropyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-syklobutyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-tert.-butyl-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid,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-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]-1-(2-metoksymetyl)pyrrolidin-l-ylheksan-l-on, N-(3-imidazol-l-ylpropyl)-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-(2-pyridin-2-yletyl)-6-[[1-(3,4-dimetylfenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksanamid, N-(3-metoksypropyl)-6-[[1-(indan-5-yl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heptanamid, 6-[[1-(4-metylfenyl)-2-(3-pyridyl)-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[1-(4-metylfenyl)-2-(4-pyridyl)-lH-benzimidazol-6-yl]oksy]-heksansyremetylester,(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-metylfenyl) -2- (2-tienyl) -lH-benzimidazol-6-yl].oksy] - heksansyremetylester, 6-[[1-(4-metylfenyl)-2-(3-tienyl)-lH-benzimidazol-6-yl]oksy] - heksansyremetylester, 6-[[2-(3-indolyl)-1-(4-metylfenyl)-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[1-(4-metylfenyl)-2-(2-furyl)-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[1-(4-metylfenyl)-2-(3-furyl^-lH-benzimidazol-6-yl]oksy]-heksansyremetylester, 6-[[1-(4-metylfenyl)-2-(5-metyl-2-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester, 6-[[1-(4-metylfenyl)-2-(3-metyl-2-tienyl)-lH-benzimidazol-6-yl]oksy]heksansyremetylester.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. Anvendelse av en forbindelse ifølge et av kravene 1-3 for fremstilling av et legemiddel for behandling eller hindring av sykdommer som er assosiert med en mikrogliaaktivering.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. Farmasøytisk middel, karakterisert ved at det inneholder én eller flere forbindelser ifølge et av kravene 1-3 og ett eller flere bærerstoffer.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. Anvendelse av en benzimidazol med den generelle formel II hvori R<1> betyr en fenyl-, naftyl-, fluorenyl-, indanyl-, pyridyl-, tienyl-, furyl-, indolyl- eller benzotienylgruppe som kan være substituert med inntil tre av de følgende substituenter uavhengig av hverandre: F, Cl, Br, I, XOH, XOR4, XCN, XSR<4>, N02, XNH2, XNHR<4>, XNR<4>R<4>', R<4>, hvorved to substituenter på R<1>, dersom de står i ortostilling til hverandre, kan være slik forbundet med hverandre at de sammen danner metandiylbisoksy, etan-1,2-diylbisoksy, propan-1,3-diyl, butan-1,4-diyl, R<2> har samme betydning som R<1>, R3 betyr én eller to substituenter som uavhengig av hverandre kan være: hydrogen, F, Cl, Br, I, XOH, XOR<4>, XCN, N02, XNH2, XNHR<4>, XNR<4>R4', XNHS02R<4> eller R<4>, R<4> og R<4>' betyr uavhengig av hverandre Ci-4-perf luor-alkyl, Ci_6-alkyl, fenyl eller fenyl-Ci-C4-alkyl, hvorved fenyl-gruppene kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3 eller C2F5/ R<5> og R<5>' betyr uavhengig av hverandre Ci-6-alkyl, hvorved et karbonatom kan være utvekslet mot 0, S, SO, S02, NH, NCi_3-alkyl eller NCi_3-alkanoyl, C3-7-sykloalkyl-C0-3-alkyl, hvorved i en 5-leddet sykloalkylring et ringledd kan være et N eller et 0 og i en 6- eller 7-leddet sykloalkylring ett eller to ringledd kan være N og/eller 0, hvorved ringnitrogener eventuelt kan være substituert med Ci-3-alkyl eller Ci_3-alkanoyl, fenyl, fenyl-Ci-C4-alkyl, pyridyl, pyridyl-Ci-C4-alkyl eller imidazolyl-Ci-C4-alkyl, hvorved alle tidligere nevnte alkylrester kan- være substituert med inntil to substituenter av 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 og alle tidligere nevnte fenyl- og pyridylgrupper kan være substituert med én eller to substituenter fra gruppen bestående av F, Cl, Br, CH3, C2H5, N02, 0CH3, OC2H5, CF3, C2F5, eller R<5> og R<5>' danner sammen med nitrogenatomet en 7-pyrrolidin-, morfolin-, piperidin- eller piperazinring og kan være substituert med Ci_4-alkyl, Ci-4-alkoksy-C0-2-alkyl, Ci-4-alkoksykarbonyl eller aminokarbonyl, A betyr Ci_i0-alkandiyl eller C2-io-alkendiyl, B betyr COOH, COOR<5>, CONH2, CONHNH2, CONHR<5>, CONR<5>R<5>', CONHOH, CONHOR<5>, S02NH2, S02NHR<5>, S02NR<5>R<5>', X betyr en binding, Y betyr 0, NH, NR<4>, NS02R<4>, hvorved de følgende forbindelser er utelukket: [ (1,2-difenyl-lH-benzimidazol-6-yl)oksy]eddiksyremetylester, 5-[(1,2-difenyl-lH-benzimidazol-6-yl)oksy]pentansyremetylester,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-difenyl-lH-benzimidazol-6-yl)oksy]butansyreetylester,4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5- [[1-(4-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester,5- [[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [ [1-(4-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 5-[[1-(4-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5-[[1-[4-[[(4-klorfenyl)sulfonyl]amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester, 5-[[1-[4-[(acetyl)amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester,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-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester,5- [[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6- [ [1-(3-nitrofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]heksan-syremetylester, 5-[[1-(3-aminofenyl)-2-fenyl-lH-benzimidazol-6-yl]oksy]pentan-syremetylester, 5-[[1-[3-[[(4-klorfenyl)sulfonyl]amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester, 5-[[1-[3-[(acetyl)amino]fenyl]-2-fenyl-lH-benzimidazol-6-yl]oksy]pentansyremetylester, for fremstilling av et legemiddel for behandling eller hindring av sykdommer som er assosiert med en mikrogliaaktivering.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.
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NO20023362L (en) 2002-09-13
HRP20020664A2 (en) 2005-04-30
CZ303726B6 (en) 2013-04-10
AU782993B2 (en) 2005-09-15
SK10002002A3 (en) 2003-02-04
SK287527B6 (en) 2011-01-04
WO2001051473A1 (en) 2001-07-19
PL209573B1 (en) 2011-09-30
RS51860B (en) 2012-02-29
CA2396227C (en) 2012-03-20
HUP0204011A3 (en) 2003-07-28
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PT1246808E (en) 2011-11-30
HRP20020664B1 (en) 2012-03-31
PL356091A1 (en) 2004-06-14
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AU4233201A (en) 2001-07-24
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