CA2396227A1 - 1,2-diaryl benzimidazoles for treating illnesses associated with a microglia activation - Google Patents
1,2-diaryl benzimidazoles for treating illnesses associated with a microglia activation Download PDFInfo
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- CA2396227A1 CA2396227A1 CA002396227A CA2396227A CA2396227A1 CA 2396227 A1 CA2396227 A1 CA 2396227A1 CA 002396227 A CA002396227 A CA 002396227A CA 2396227 A CA2396227 A CA 2396227A CA 2396227 A1 CA2396227 A1 CA 2396227A1
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Abstract
1,2-Diarylbenzimidazoles of general formula (I) and the use of benzimidazole derivatives for the production of pharmaceutical agents for treatment and prophylaxis of diseases that are associated with a microglia activation are described.
(see formula I)
(see formula I)
Claims (24)
1.
in which R1 means a monocyclic or bicyclic C6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-4 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, I, C(NH)NH2, C(NH)NHR4, C(NH)NR4R4, C(NR4)NH2, C(NR4)NHR4, C(NR4)NR4R4, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC (NOH) R4, XC (NOR4) R4', XC (NO(COR4))R4' XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)SO2R4', XNR4SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl,
in which R1 means a monocyclic or bicyclic C6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-4 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, I, C(NH)NH2, C(NH)NHR4, C(NH)NR4R4, C(NR4)NH2, C(NR4)NHR4, C(NR4)NR4R4, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC (NOH) R4, XC (NOR4) R4', XC (NO(COR4))R4' XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)SO2R4', XNR4SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl,
2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R1, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R2 means a monocyclic or bicyclic C6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-4 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, I, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4) SO2R4', XNR4SO2R4', tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediyl-bisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R3 means one or two substituents, which form, independently of one another:
hydrogen, F, Cl, Br, I, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)(SO2R4'), XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, or R3 can be R4, whereby two substituents at R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R4 and R4', independently of one another, mean C1-4 perfluoroalkyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, C3-cycloalkyl, (C1-3 alkyl-C3-7 cycloalkyl), C1-3 alkyl-C6-10 - aryl, C1-3 alkyl-5 to 10-membered heteroaryl, with 1-4 N, S or O atoms, C6-10aryl or 5- to 10-membered heteroaryl with 1-4 N, S or O atoms, whereby the aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy group or ethane-1,2-diylbisoxy group, and in addition in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, R5 and R5', independently of one another, mean C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, whereby a carbon atom can be exchanged for O, S, SO, SO2, NH, N C1-3 alkyl or N C1-3 alkanoyl, C3-7 cycloalkyl-CO-3 alkyl, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, C6-10 aryl or 5- to 10-membered heteroaryl with 1-4 heteroatoms from N, S, and O, whereby the above-mentioned alkyl, alkenyl and alkinyl chains can be substituted with one of the previously mentioned cycloalkyls, aryls or heteroaryls, whereby all previously mentioned alkyl and cycloalkyl radicals with up to two substituents consisting of CF3, C2F5, OH, O C1-3 alkyl, NH2, NH C1-3 alkyl, NH C1-3 alkanoyl, N(C1-3 alkyl)2, N(C1-3 alkyl)(C1-3 alkanoyl), COOH, CONH2, COO C1-3 alkyl and all previously mentioned aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy, ethane-1,2-diylbisoxy group, or R5 and R5' together with the nitrogen atom form a 5-to 7-membered heterocyclic compound, which can contain another oxygen, nitrogen or sulfur atom and can be substituted with C1-4 alkyl, C1-4 alkoxy-C0-2 alkyl, C1-4 alkoxy-carbonyl, aminocarbonyl or phenyl, A means C1-10 alkanediyl, C2-10 alkenediyl, C2-10 alkinediyl, (C0-5 alkanediyl-C3-7 cycloalkanediyl-C0-5 alkanediyl), whereby in a 5-membered cyeloalkyl ring, a ring member can be an N or an 0, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, whereby in the above-mentioned aliphatic chains, a carbon atom or two carbon atoms can be exchanged for O, NH, N C1-3 alkyl, N C1-3 alkanoyl, and whereby alkyl or cycloalkyl groups can be substituted with up to two substituents consisting of =O, OH, O C1-3 alkyl, NH2, NH
C1-3 alkyl, NH C1-3 alkanoyl, N(C1-3 alkyl)2, N(C1-3 alkyl) (C1-3 alkanoyl), B means COOH, COOR5, CONH5, CONHNH2, CONHR5, CONR5R5', CONHOH, CONHOR5, SO3H, SO2NH2, SO2NHR5, SO2NR5R5', PO3H, PO(OH)(OR5), PO(OR5)(OR5'), PO(OH)(NHR5).
PO(NHR5)(NHR5').
tetrazolyl, in each case bonded to a carbon atom of group A, or the entire group Y-A-B N (SO2R4)(SO2R4') or NHSO2R4, Z means a bond, CH2, (CH2)2, CH(CH3), (CH2)3, CH(CH2CH3), CH(CH3)CH2, CH2CH(CH3), Y means O, NH, NR4, NCOR4, NSO2R4, provided that if Y means NH, NR4, NCOR4 or NSO2R4, and a) substituent R2 contains a nitrogen-containing, saturated heterocyclic compound, this heterocyclic compound is not substituted in the imine nitrogen with H, methyl, ethyl, propyl or isopropyl, or b) in optionally present groups XNHR4 or XNR4R4' of substituent R2, R4 and/or R4' does not mean C1-4 alkyl, provided that B does not mean COON, SO3H, PO3H2 or tetrazolyl at the same time, and R1 and R2, independently of one another, mean C5-6 heteroaryl or phenyl, if the latter, independently of one another, are unsubstituted, or are substituted simply with C1-6 alkyl, C1-4 perfluoroalkyl, O C1-6 alkyl, O C1-4 perfluoroalkyl, COOH, COO C1-6 alkyl, CO C1-6 alkyl, CONH2, CONHR4, NO2, NH2, NHCOR4, NHSO2R4, or with 1 or 2 halogen atoms from the group that consists of F, Cl, Br, and I, and whereby the following compounds are excluded:
[(1,2-biphenyl-1H-benzimidazol-6-yl)oxy]acetic acid methyl ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester, 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-pentanoic acid methyl ester, 6-[[1-(4-nitrophenyl)-2-phenyl-iH-benzimidazol-6-yl]oxy]hexanoic 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-iH-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[4-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester 5-[[1-(3-nitrophenyl)-2-phenyl-iH-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[3-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[3-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester.
2. Benzimidazoles according to claim 1, characterized in that R1 means a monocyclic or bicyclic C6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-2 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4, XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, NO2, XNHR4, XNR4R4', R4 whereby two substituents at R1, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
F, Cl, Br, I, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4) SO2R4', XNR4SO2R4', tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediyl-bisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R3 means one or two substituents, which form, independently of one another:
hydrogen, F, Cl, Br, I, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)(SO2R4'), XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, or R3 can be R4, whereby two substituents at R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R4 and R4', independently of one another, mean C1-4 perfluoroalkyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, C3-cycloalkyl, (C1-3 alkyl-C3-7 cycloalkyl), C1-3 alkyl-C6-10 - aryl, C1-3 alkyl-5 to 10-membered heteroaryl, with 1-4 N, S or O atoms, C6-10aryl or 5- to 10-membered heteroaryl with 1-4 N, S or O atoms, whereby the aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy group or ethane-1,2-diylbisoxy group, and in addition in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, R5 and R5', independently of one another, mean C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, whereby a carbon atom can be exchanged for O, S, SO, SO2, NH, N C1-3 alkyl or N C1-3 alkanoyl, C3-7 cycloalkyl-CO-3 alkyl, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, C6-10 aryl or 5- to 10-membered heteroaryl with 1-4 heteroatoms from N, S, and O, whereby the above-mentioned alkyl, alkenyl and alkinyl chains can be substituted with one of the previously mentioned cycloalkyls, aryls or heteroaryls, whereby all previously mentioned alkyl and cycloalkyl radicals with up to two substituents consisting of CF3, C2F5, OH, O C1-3 alkyl, NH2, NH C1-3 alkyl, NH C1-3 alkanoyl, N(C1-3 alkyl)2, N(C1-3 alkyl)(C1-3 alkanoyl), COOH, CONH2, COO C1-3 alkyl and all previously mentioned aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy, ethane-1,2-diylbisoxy group, or R5 and R5' together with the nitrogen atom form a 5-to 7-membered heterocyclic compound, which can contain another oxygen, nitrogen or sulfur atom and can be substituted with C1-4 alkyl, C1-4 alkoxy-C0-2 alkyl, C1-4 alkoxy-carbonyl, aminocarbonyl or phenyl, A means C1-10 alkanediyl, C2-10 alkenediyl, C2-10 alkinediyl, (C0-5 alkanediyl-C3-7 cycloalkanediyl-C0-5 alkanediyl), whereby in a 5-membered cyeloalkyl ring, a ring member can be an N or an 0, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, whereby in the above-mentioned aliphatic chains, a carbon atom or two carbon atoms can be exchanged for O, NH, N C1-3 alkyl, N C1-3 alkanoyl, and whereby alkyl or cycloalkyl groups can be substituted with up to two substituents consisting of =O, OH, O C1-3 alkyl, NH2, NH
C1-3 alkyl, NH C1-3 alkanoyl, N(C1-3 alkyl)2, N(C1-3 alkyl) (C1-3 alkanoyl), B means COOH, COOR5, CONH5, CONHNH2, CONHR5, CONR5R5', CONHOH, CONHOR5, SO3H, SO2NH2, SO2NHR5, SO2NR5R5', PO3H, PO(OH)(OR5), PO(OR5)(OR5'), PO(OH)(NHR5).
PO(NHR5)(NHR5').
tetrazolyl, in each case bonded to a carbon atom of group A, or the entire group Y-A-B N (SO2R4)(SO2R4') or NHSO2R4, Z means a bond, CH2, (CH2)2, CH(CH3), (CH2)3, CH(CH2CH3), CH(CH3)CH2, CH2CH(CH3), Y means O, NH, NR4, NCOR4, NSO2R4, provided that if Y means NH, NR4, NCOR4 or NSO2R4, and a) substituent R2 contains a nitrogen-containing, saturated heterocyclic compound, this heterocyclic compound is not substituted in the imine nitrogen with H, methyl, ethyl, propyl or isopropyl, or b) in optionally present groups XNHR4 or XNR4R4' of substituent R2, R4 and/or R4' does not mean C1-4 alkyl, provided that B does not mean COON, SO3H, PO3H2 or tetrazolyl at the same time, and R1 and R2, independently of one another, mean C5-6 heteroaryl or phenyl, if the latter, independently of one another, are unsubstituted, or are substituted simply with C1-6 alkyl, C1-4 perfluoroalkyl, O C1-6 alkyl, O C1-4 perfluoroalkyl, COOH, COO C1-6 alkyl, CO C1-6 alkyl, CONH2, CONHR4, NO2, NH2, NHCOR4, NHSO2R4, or with 1 or 2 halogen atoms from the group that consists of F, Cl, Br, and I, and whereby the following compounds are excluded:
[(1,2-biphenyl-1H-benzimidazol-6-yl)oxy]acetic acid methyl ester, 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid methyl ester, 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid ethyl ester, 5-[[1-(4-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]-pentanoic acid methyl ester, 6-[[1-(4-nitrophenyl)-2-phenyl-iH-benzimidazol-6-yl]oxy]hexanoic 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-iH-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[4-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester 5-[[1-(3-nitrophenyl)-2-phenyl-iH-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester, 5-[[1-(3-aminophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[3-[[(4-chlorophenyl)sulfonyl]amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester, 5-[[1-[3-[(acetyl)amino]phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester.
2. Benzimidazoles according to claim 1, characterized in that R1 means a monocyclic or bicyclic C6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-2 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4, XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, NO2, XNHR4, XNR4R4', R4 whereby two substituents at R1, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
3. Benzimidazoles according to claim 1 or 2, wherein R2 means a monocyclic or bicyclic C6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-2 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)SO2R4'; XNR4SO2R4', R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)SO2R4'; XNR4SO2R4', R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
4. Benzimidazoles according to one of claims 1-3, wherein R3 means one or two substituents, which, independently of one another, can be:
hydrogen, F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4N4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, or R4, whereby two substituents R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, or butane-1,4-diyl.
hydrogen, F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4N4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, or R4, whereby two substituents R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, or butane-1,4-diyl.
5. Benzimidazoles according to one of claims 1-4, wherein R4 and R4', independently of one another, mean CF3, C2F5, C1-4-alkyl, C2-4-alkenyl, CZ-4-alkinyl, C3-6-cycloalkyl, (C1-3-alkyl-C3-6-cycloalkyl), phenyl or 5- to 6-membered heteroaryl with 1-2 N, S or O atoms, whereby the phenyl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, OCH3, OC2H5, CF3, C2F5, and in addition in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3-alkyl or C1-3-alkanoyl.
and/or O, whereby ring nitrogens optionally can be substituted with C1-3-alkyl or C1-3-alkanoyl.
6. Benzimidazoles according to one of claims 1-5, wherein R5 and R5', independently of one another, can be C1-6 alkyl, Whereby a carbon atom can be exchanged for O, NH, N C1-3 alkyl , N C1-3 alkanoyl , C3-7 cycloalkyl-C0-3 alkyl, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, whereby the above-mentioned C1-6 alkyl part can be substituted with one of the previously mentioned cycloalkyls or else a 5- to 6-membered heteroaromatic compound with 1-2 heteroatoms, selected from N, S or 0, whereby all previously mentioned alkyl and cycloalkyl parts can be substituted with up to two substituents that consist of CF3, OH, O C1-3 alkyl, and the previously mentioned heteroaryl groups with one or two substituents that consist of F, Cl, CF3, CH3, C2H5, OCH3, OC2H5, or R5 and R5' together with the nitrogen atom form a 5- to 7-membered heterocyclic compound, which can contain another oxygen, nitrogen or sulfur atom and can be substituted with C1-4-alkyl, C1-4-alkoxy-C0-2-alkyl, C1-4-alkoxy-carbonyl, aminocarbonyl or phenyl.
7. Benzimidazoles according to one of claims 1-6, wherein A means C1-10 alkanediyl, C2-10 alkenediyl, C2-10 alkinediyl, (C0-5 alkanediyl-C3-T cycloalkanediyl-C-5 alkanediyl), whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, or in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be -substituted with C1-3 alkyl or C1-3 alkanoyl, whereby in the above-mentioned aliphatic chains, a carbon atom or two carbon atoms can be exchanged for 0, NH, N C1-3 alkyl, or N C1-3 alkanoyl.
and/or O, whereby ring nitrogens optionally can be -substituted with C1-3 alkyl or C1-3 alkanoyl, whereby in the above-mentioned aliphatic chains, a carbon atom or two carbon atoms can be exchanged for 0, NH, N C1-3 alkyl, or N C1-3 alkanoyl.
8. Benzimidazoles according to one of claims 1-7, wherein B means COOH, COOR5, CONH2, CONHR5, CONR5R5', CONHOH, CONHOR5 or tetrazolyl, in each case bonded to a carbon atom of group A.
9. Benzimidazoles according to one of claims 1-8, wherein X means a bond or methylene.
10. Benzimidazoles according to one of claims 1-9, wherein Y means 0.
11. [(1,2-Diphenyl-1H-benzimidazol-6-yl)oxy]acetic acid isopropyl ester 3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester 2-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propanoic acid methyl ester 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid isopropyl ester 5-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]pentanoic acid isopropyl ester 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide N-methoxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide N-(phenylmethoxy)-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide N-hydroxy-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide 7-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]heptanoic acid methyl ester 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic 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]hexanoic acid isopropyl ester 6-[(1-(3-cyanophenyl)-2-phenyl-1H-benzimidazol-6-y1] oxy] hexanoic acid 6-((1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-cyanophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[(1-(3-chlorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic 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-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(3-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-([1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-([1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[(1-(3,5-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[1-(3-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(3,4-dimethoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-([1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-([1-[3,4-(methylenedioxy)phenyl]-2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-([2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl] oxy] hexanoic acid 6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-[4-(N,N-dimethylamino)phenyl]-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid 6-[[1-phenyl-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-(3-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-(4-chlorophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-(4-methylphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[1-phenyl-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester 6-[(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl)oxy]hexanoic acid isopropyl ester 6-[[5-[((4-bromophenyl)sulfonyl]amino]-1,2-Biphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-Biphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[5-[((4-chlorophenyl)sulfonyl]amino]-1,2-Biphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[1,2-Biphenyl-5-[((3-methylphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-((1,2-Biphenyl-5-[[(4-methylphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-((1,2-Biphenyl-5-[[(4-methoxyphenyl)sulfonyl]amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[1,2-Biphenyl-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-Biphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[(1,2-Biphenyl-5-[(propylsulfonyl)amino]-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[5-[(benzylsulfonyl)amino]-1,2-Biphenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 2-(2-[(1,2-Biphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]acetic acid methyl ester 3-[2-[(1,2-Biphenyl-1H-benzimidazol-6-yl)oxy]ethoxy]propanoic acid methyl ester 6-[[1-(3-nitrophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid ethyl ester 6-[[4-acetyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester 6-[[2-phenyl-1-[4-(thiomethyl)phenyl]-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester 6-[[2-phenyl-1-[(4-(thiomethyl)phenyl]-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-5-yl]oxy]hexanoic acid methyl ester 6-[[2-phenyl-1-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 4-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]butanoic acid methyl ester N-(phenylmethoxy)-6-[[2-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-6-yl]oxy]-hexanamide N,N-dimethyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide N-isopropyl-6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanamide 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]-1-pyrrolidin-1-ylhexan-1-one 5-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[4-(acetyloxy)-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[4-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[4-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid 6-[[7-methyl-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester
12. 6-[[2-Phenyl-1-(3-pyridyl)-1H-benzimidazol-5-yl]oxy]hexanoic 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-fluoro-phenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-(4-methoxyphenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]-hexanoic acid methyl ester 6-[[2-(4-bromophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-[4-(trifluoromethyl)phenyl]-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid 6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester 6-[[5-hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[5-methoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-2-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-(4-methoxyphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 4-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]butanoic acid methyl ester 5-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester 5-[[5-[[(4-chlorophenyl)sulfonyl]amino]-1,2-diphenyl-1H-benzimidazol-6-yl]oxy]pentanoic acid methyl ester 6-[[5-[[(4-(trifluoromethyl)phenyl)sulfonyl]amino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[5-[[(4-chlorophenyl)sulfonyl]methylamino]-1-(4-methoxyphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid 6-[[1-(3-fluorophenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-(4-nitrophenyl)-1-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-phenyl-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic 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]hexanamide 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-ylhexan-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]hexanamide 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]hexanamide (R)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]1-(2-methoxymethyl)-pyrrolidin-1-ylhexan-1-one N-(3-imidazol-1-yl-propyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide N-(2-pyridin-2-ylethyl)-6-[[1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanamide N-(3-methoxypropyl)-6-[[1-(indan-5-yl)-2-phenyl-1H-benzimidazol-6-yl]oxy]heptanamide 6-[[1-(4-methylphenyl)-2-(3-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-(4-pyridyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-(2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[2-(3-indolyl)-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-(2-furyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-(3-furyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-(5-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 6-[[1-(4-methylphenyl)-2-(3-methyl-2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester.
13. Use of a compound according to one of claims 1-12 for the production of a pharmaceutical agent for treating or preventing diseases that are associated with a microglia activation.
14. Pharmaceutical agent, wherein it contains one or more compounds according to one of claims 1-12 and one or more vehicles.
15. Use of a benzimidazole of general formula II
in which R1 means a monocyclic or bicyclic C6-12-aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-4 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, I, C(NH)NH2, C(NH)NHR4, C(NH)NR4R4', C(NR4)NH2, C(NR4)NHR4', C(NR4)NR4R4', XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', No2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)(SO2R4'), XNR4So2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R1, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R2 means a monocyclic or bicyclic C6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-4 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, I, C(NH)NH2, C(NH)NHR4, C(NH)NR4R4', C(NR4)NH2, C(NR4)NHR4', C(NR4)NR4R4', XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)(SO2R4'), XNR4SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R3 stands for one or two substituents, which form, independently of one another:
hydrogen, F, Cl, Br, I, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)(SO2R4'), XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R4 and R4', independently of one another, mean C1-4 perfluoroalkyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, C3-7 cycloalkyl, (C1-3 alkyl-C3-7 cycloalkyl), C1-3 alkyl-C6-10- aryl, C1-3 alkyl 5 to 10-membered heteroaryl, with 1-4 N, S or O atoms, C6-10-aryl or 5- to 10-membered heteroaryl with 1-4 N, S or O atoms, whereby the C6-10-aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy group or ethane-1,2-diylbisoxy group, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, R5 and R5', independently of one another, mean hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, whereby a carbon atom can be exchanged for O, S, SO, SO2, NH, N C1-3 alkyl or N C1-3 alkanoyl, C3-7 cycloalkyl-C0-3 alkyl, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, C6-10 aryl or 5- to 10-membered heteroaryl with 1-4 heteroatoms from N, S, and O, whereby the above-mentioned alkyl, alkenyl and alkinyl chains can be substituted with one of the previously mentioned cycloalkyls, aryls or heteroaryls, whereby all previously mentioned alkyl and cycloalkyl radicals with up to two substituents consisting of CF3, C2F5, OH, O C1-3 alkyl, NH2, NH C1-3 alkyl, NH C1-3 alkanoyl, N (C1-3 alkyl)2, N(C1-3 alkyl)(C1-3 alkanoyl), COOH, CONH2, COO C1-3 alkyl and all previously mentioned aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy, ethane-1,2-diylbisoxy group, or R5 and R5' together with the nitrogen atom form a 5-to 7-membered heterocyclic compound, which can contain another oxygen, nitrogen or sulfur atom and can be substituted with C1-4-alkyl, C1-4-alkoxy-C0-2-alkyl, C1-4-alkoxy-carbonyl, aminocarbonyl or phenyl, A means C1-10 alkanediyl, C2-10 alkenediyl, C2-10 alkinediyl, (C0-5 alkanediyl-C3-7 cycloalkanediyl-C0-5 alkanediyl), (C0-5 alkanediylarylene-C0-5 alkanediyl), (C0-5 alkanediyl-heteroarylene-C0-5 alkanediyl), whereby the aryl and heteroaryl groups can be substituted with one or two substituents that consist Of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3-alkyl or C1-3-alkanoyl, whereby in the above-mentioned aliphatic chains, a carbon atom or two carbon atoms can be exchanged for 0, NH, NR4, NCOR4, NSO2R4, and whereby alkyl or cycloalkyl groups can be substituted with up to two substituents consisting of F, OH, OR4, OCOR4, =O, NH2, NR4R4', NHCOR4, NHCOOR4, NHCONHR4, NHSO2R4 SH, SR4, B means hydrogen, OH, OCOR5, OCONHR5, OCOOR5, COR5, C(NOH)R5, C(NOR5)R5', C(NO(COR5))R5', COOH, COOR5, CONH2, CONHNH2, CONHR5, CONR5R5', CONHOH, CONHOR5, SO3H, SO2NH2, SO2NHR5, SO2NR5R5', PO3H, PO(OH)(OR5), PO(OR5)(OR5'), PO(OH)(NHR5), PO(NHR5)(NHR5'), tetrazolyl, respectively bonded to a carbon atom of group A, or the entire group Y-A-B N(SO2R4)(SO2R4') or NHSO2R4, X means a bond, CH2, (CH2)2, CH(CH3), (CH2)3, CH(CH2CH3), CH(CH3)CH2, CH2CH(CH3), Y means a bond, O, S, SO, SO2, NH, NR4, NCOR4, NSO2R4, for the production of a pharmaceutical agent for treating or preventing diseases that are associated with a microglia activation.
in which R1 means a monocyclic or bicyclic C6-12-aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-4 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, I, C(NH)NH2, C(NH)NHR4, C(NH)NR4R4', C(NR4)NH2, C(NR4)NHR4', C(NR4)NR4R4', XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', No2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)(SO2R4'), XNR4So2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R1, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R2 means a monocyclic or bicyclic C6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-4 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, I, C(NH)NH2, C(NH)NHR4, C(NH)NR4R4', C(NR4)NH2, C(NR4)NHR4', C(NR4)NR4R4', XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4)(SO2R4'), XNR4SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R3 stands for one or two substituents, which form, independently of one another:
hydrogen, F, Cl, Br, I, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONHR4, XCONR4R4', XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)(SO2R4'), XNHCOR4, XNHCOOR4, XNHCONHR4, tetrahydro-2,5-dioxopyrrol-1-yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, R4, whereby two substituents at R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl, R4 and R4', independently of one another, mean C1-4 perfluoroalkyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, C3-7 cycloalkyl, (C1-3 alkyl-C3-7 cycloalkyl), C1-3 alkyl-C6-10- aryl, C1-3 alkyl 5 to 10-membered heteroaryl, with 1-4 N, S or O atoms, C6-10-aryl or 5- to 10-membered heteroaryl with 1-4 N, S or O atoms, whereby the C6-10-aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy group or ethane-1,2-diylbisoxy group, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, R5 and R5', independently of one another, mean hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkinyl, whereby a carbon atom can be exchanged for O, S, SO, SO2, NH, N C1-3 alkyl or N C1-3 alkanoyl, C3-7 cycloalkyl-C0-3 alkyl, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, C6-10 aryl or 5- to 10-membered heteroaryl with 1-4 heteroatoms from N, S, and O, whereby the above-mentioned alkyl, alkenyl and alkinyl chains can be substituted with one of the previously mentioned cycloalkyls, aryls or heteroaryls, whereby all previously mentioned alkyl and cycloalkyl radicals with up to two substituents consisting of CF3, C2F5, OH, O C1-3 alkyl, NH2, NH C1-3 alkyl, NH C1-3 alkanoyl, N (C1-3 alkyl)2, N(C1-3 alkyl)(C1-3 alkanoyl), COOH, CONH2, COO C1-3 alkyl and all previously mentioned aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy, ethane-1,2-diylbisoxy group, or R5 and R5' together with the nitrogen atom form a 5-to 7-membered heterocyclic compound, which can contain another oxygen, nitrogen or sulfur atom and can be substituted with C1-4-alkyl, C1-4-alkoxy-C0-2-alkyl, C1-4-alkoxy-carbonyl, aminocarbonyl or phenyl, A means C1-10 alkanediyl, C2-10 alkenediyl, C2-10 alkinediyl, (C0-5 alkanediyl-C3-7 cycloalkanediyl-C0-5 alkanediyl), (C0-5 alkanediylarylene-C0-5 alkanediyl), (C0-5 alkanediyl-heteroarylene-C0-5 alkanediyl), whereby the aryl and heteroaryl groups can be substituted with one or two substituents that consist Of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3-alkyl or C1-3-alkanoyl, whereby in the above-mentioned aliphatic chains, a carbon atom or two carbon atoms can be exchanged for 0, NH, NR4, NCOR4, NSO2R4, and whereby alkyl or cycloalkyl groups can be substituted with up to two substituents consisting of F, OH, OR4, OCOR4, =O, NH2, NR4R4', NHCOR4, NHCOOR4, NHCONHR4, NHSO2R4 SH, SR4, B means hydrogen, OH, OCOR5, OCONHR5, OCOOR5, COR5, C(NOH)R5, C(NOR5)R5', C(NO(COR5))R5', COOH, COOR5, CONH2, CONHNH2, CONHR5, CONR5R5', CONHOH, CONHOR5, SO3H, SO2NH2, SO2NHR5, SO2NR5R5', PO3H, PO(OH)(OR5), PO(OR5)(OR5'), PO(OH)(NHR5), PO(NHR5)(NHR5'), tetrazolyl, respectively bonded to a carbon atom of group A, or the entire group Y-A-B N(SO2R4)(SO2R4') or NHSO2R4, X means a bond, CH2, (CH2)2, CH(CH3), (CH2)3, CH(CH2CH3), CH(CH3)CH2, CH2CH(CH3), Y means a bond, O, S, SO, SO2, NH, NR4, NCOR4, NSO2R4, for the production of a pharmaceutical agent for treating or preventing diseases that are associated with a microglia activation.
16. Use according to claim 15, whereby in general formula II, R1 means a monocyclic or bicyclic aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-2 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XCN, XCOOH, XCOOR4, XCONH2, XCONR4R44', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, NO2, XNHR4, XNR4R4', R4, whereby two substituents at R1, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XCN, XCOOH, XCOOR4, XCONH2, XCONR4R44', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, NO2, XNHR4, XNR4R4', R4, whereby two substituents at R1, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
17. Use according to claim 15 or 16, whereby in general formula II, R2 means a monocyclic or bicyclic aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group with 1-2 heteroatoms selected from the group that consists of N, S or O, whereby the above-mentioned aryl group or heteroaryl group can be substituted with up to three of the following substituents, independently of one another:
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4) (SO2R4'), XNR4SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4', XCN, XCOOH, XCOOR4, XCONH2, XCONR4R4', XCONHR4, XCONHOH, XCONHOR4, XCOSR4, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4, SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XN(SO2R4) (SO2R4'), XNR4SO2R4', XNHCOR4, XNHCOOR4, XNHCONHR4, R4, whereby two substituents at R2, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
18. Use according to one of claims 15-17, whereby in general formula II
R3 stands for one or two substituents, which independently of one another, mean:
hydrogen, F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4' , XCN, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4; SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)(SO2R4'), XNHCOR4, XNHCOOR4, XNHCONHR4, or R4, whereby two substituents R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
R3 stands for one or two substituents, which independently of one another, mean:
hydrogen, F, Cl, Br, XOH, XOR4, XOCOR4, XOCONHR4, XOCOOR4, XCOR4, XC(NOH)R4, XC(NOR4)R4', XC(NO(COR4))R4' , XCN, XSR4, XSOR4, XSO2R4, SO2NH2, SO2NHR4; SO2NR4R4', NO2, XNH2, XNHR4, XNR4R4', XNHSO2R4, XNR4SO2R4', XN(SO2R4)(SO2R4'), XNHCOR4, XNHCOOR4, XNHCONHR4, or R4, whereby two substituents R3, if they are in ortho-position to one another, can be linked to one another in such a way that they jointly form methanediylbisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane-1,4-diyl.
19. Use according to one of claims 15-18, whereby in general formula II
R4 and R4', independently of one another, mean CF3, C2F5, C1-4 alkyl, C2-4 alkenyl, C2-4 alkinyl, C3-6 cycloalkyl, (C1-3 alkyl-C3-6 cycloalkyl), C1-3 alkyl aryl, C1-3 alkylheteroaryl, monocyclic aryl or 5- to 6-membered heteroaryl with 1-2 N, S or O atoms, whereby the aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group, and in addition in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl.
R4 and R4', independently of one another, mean CF3, C2F5, C1-4 alkyl, C2-4 alkenyl, C2-4 alkinyl, C3-6 cycloalkyl, (C1-3 alkyl-C3-6 cycloalkyl), C1-3 alkyl aryl, C1-3 alkylheteroaryl, monocyclic aryl or 5- to 6-membered heteroaryl with 1-2 N, S or O atoms, whereby the aryl and heteroaryl groups can be substituted with one or two substituents from the group that consists of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5 or else can carry an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group, and in addition in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6-membered cycloalkyl ring, one or two ring members can be N and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl.
20. Use according to one of claims 15-19, whereby in general formula II
R5 and R5', independently of one another, can be C1-6 alkyl, whereby a carbon atom can be exchanged for O, NH, N C1-3 alkyl, N C1-3 alkanoyl, C3-7 cycloalkyl-C0-3 alkyl, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, whereby the above-mentioned C1-6 alkyl part can be substituted with one of the previously mentioned cycloalkyls or else a 5- to 6-membered heteroaromatic compound with 1-2 heteroatoms, selected from the group that consists of N, S or O, whereby all previously mentioned alkyl and cycloalkyl parts can be substituted with up to two substituents that consist of CF3, OH, O C1-3 alkyl, and the previously mentioned heteroaryl groups can be substituted with one or two substituents that consist of F, Cl, CF3, CH3, C2H5, OCH3, OC2H5, or R5 and R5' together with the nitrogen atom form a 5-to 7-membered heterocyclic compound, which can contain another oxygen, nitrogen or sulfur atom and can be substituted with C1-4-alkyl, C1-4-alkoxy-C0-2-alkyl, C1-4-alkoxy-carbonyl, aminocarbonyl or phenyl.
R5 and R5', independently of one another, can be C1-6 alkyl, whereby a carbon atom can be exchanged for O, NH, N C1-3 alkyl, N C1-3 alkanoyl, C3-7 cycloalkyl-C0-3 alkyl, whereby in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, whereby the above-mentioned C1-6 alkyl part can be substituted with one of the previously mentioned cycloalkyls or else a 5- to 6-membered heteroaromatic compound with 1-2 heteroatoms, selected from the group that consists of N, S or O, whereby all previously mentioned alkyl and cycloalkyl parts can be substituted with up to two substituents that consist of CF3, OH, O C1-3 alkyl, and the previously mentioned heteroaryl groups can be substituted with one or two substituents that consist of F, Cl, CF3, CH3, C2H5, OCH3, OC2H5, or R5 and R5' together with the nitrogen atom form a 5-to 7-membered heterocyclic compound, which can contain another oxygen, nitrogen or sulfur atom and can be substituted with C1-4-alkyl, C1-4-alkoxy-C0-2-alkyl, C1-4-alkoxy-carbonyl, aminocarbonyl or phenyl.
21. Use according to one of claims 15-20, whereby in general formula II
A means C1-10 alkanediyl, C2-10 alkenediyl, C2-10 alkinediyl, (C0-5 alkanediyl-C3-7 cycloalkanediyl-C0-5 alkanediyl) , or (C0-5 alkanediyl-heteroarylene-C0-5 alkanediyl), whereby an optionally present heteroaryl group can be substituted with one or two substituents that consist of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5, and in addition in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, whereby in an aliphatic chain, a carbon atom or two carbon atoms can be exchanged for O, NH, N C1-3 alkyl, N
C1-3 alkanoyl, NSO2 C1-3 alkyl, and whereby alkyl or cycloalkyl parts can be substituted with up to two F atoms or one of the substituents that consists of OH, O C1-3 alkyl, O C1-3 alkanoyl, =O, NH2, NH C1-3 alkyl, N (C1-3 alkyl) 2, NH C1-3 alkanoyl, N (C1-3 alkyl) (C1-3 alkanoyl) , NHCOO C1-3 alkyl, NHCONH C1-3 alkyl, NHSO2 C1-3 alkyl, SH, S C1-3 alkyl.
A means C1-10 alkanediyl, C2-10 alkenediyl, C2-10 alkinediyl, (C0-5 alkanediyl-C3-7 cycloalkanediyl-C0-5 alkanediyl) , or (C0-5 alkanediyl-heteroarylene-C0-5 alkanediyl), whereby an optionally present heteroaryl group can be substituted with one or two substituents that consist of F, Cl, Br, CH3, C2H5, NO2, OCH3, OC2H5, CF3, C2F5, and in addition in a 5-membered cycloalkyl ring, a ring member can be an N or an O, and in a 6- or 7-membered cycloalkyl ring, one or two ring members can be N
and/or O, whereby ring nitrogens optionally can be substituted with C1-3 alkyl or C1-3 alkanoyl, whereby in an aliphatic chain, a carbon atom or two carbon atoms can be exchanged for O, NH, N C1-3 alkyl, N
C1-3 alkanoyl, NSO2 C1-3 alkyl, and whereby alkyl or cycloalkyl parts can be substituted with up to two F atoms or one of the substituents that consists of OH, O C1-3 alkyl, O C1-3 alkanoyl, =O, NH2, NH C1-3 alkyl, N (C1-3 alkyl) 2, NH C1-3 alkanoyl, N (C1-3 alkyl) (C1-3 alkanoyl) , NHCOO C1-3 alkyl, NHCONH C1-3 alkyl, NHSO2 C1-3 alkyl, SH, S C1-3 alkyl.
22. Use according to one of claims 15-21, whereby in general formula II
B means hydrogen, OH, OCOR5, OCONHR5, OCOOR5, COOH, COOR5, CONH2, CONHR5, CONR5R5', CONHOH, CONHOR5, or tetrazolyl, in each case bonded to a carbon atom of group A.
B means hydrogen, OH, OCOR5, OCONHR5, OCOOR5, COOH, COOR5, CONH2, CONHR5, CONR5R5', CONHOH, CONHOR5, or tetrazolyl, in each case bonded to a carbon atom of group A.
23. Use according to one of claims 15-22, whereby in general formula II, X means a bond or CH2.
24. Use according to one of claims 15-23, whereby in general formula II, Y means a bond, O, S, NH, NR4, NCOR4 or NSO2R4.
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TW200808769A (en) | 2006-04-18 | 2008-02-16 | Astrazeneca Ab | Therapeutic compounds |
JP5255994B2 (en) * | 2008-11-04 | 2013-08-07 | 国立大学法人 岡山大学 | Nuclear receptor ligand |
WO2012012478A1 (en) * | 2010-07-21 | 2012-01-26 | Merck Sharp & Dohme Corp. | Aldosterone synthase inhibitors |
CN102382102B (en) * | 2010-09-06 | 2014-01-08 | 中国科学院广州生物医药与健康研究院 | Amide compound |
JP6200903B2 (en) * | 2012-02-17 | 2017-09-20 | キネタ フォー エルエルシー | Antiviral drugs for the treatment of arenavirus infections |
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US4430502A (en) * | 1982-08-13 | 1984-02-07 | The Upjohn Company | Pyridinyl substituted benzimidazoles and quinoxalines |
DK0520200T3 (en) * | 1991-06-24 | 1998-09-23 | Neurosearch As | Imadazole compounds, their preparation and use |
MX9203323A (en) * | 1991-07-11 | 1994-07-29 | Hoechst Ag | THE USE OF XANTHINE DERIVATIVES FOR THE TREATMENT OF SECONDARY INJURIES OF THE NERVOUS CELLS AND FUNCTIONAL DISORDERS AFTER CRANIAL-BRAIN TRAUMA. |
DE4129603A1 (en) * | 1991-09-06 | 1993-03-11 | Thomae Gmbh Dr K | CONDENSED 5-LOW HETEROCYCLES, METHOD FOR THE PRODUCTION THEREOF, AND MEDICAMENTS CONTAINING THESE COMPOUNDS |
DE4330959A1 (en) * | 1993-09-09 | 1995-03-16 | Schering Ag | New benzimidazole derivatives, processes for their preparation and their pharmaceutical use |
US5552426A (en) * | 1994-04-29 | 1996-09-03 | Eli Lilly And Company | Methods for treating a physiological disorder associated with β-amyloid peptide |
NZ270985A (en) * | 1994-04-29 | 1997-06-24 | Lilly Co Eli | Substituted benzimidazole derivatives; medicaments and preparation of medicaments |
WO1997012613A1 (en) * | 1995-10-05 | 1997-04-10 | Warner-Lambert Company | Method for treating and preventing inflammation and atherosclerosis |
JP2000506529A (en) * | 1996-03-11 | 2000-05-30 | イーライ・リリー・アンド・カンパニー | Methods for treating or preventing interstitial cystitis |
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