NO326408B1 - Benzimidazoler, farmasoytisk preparat og anvendelse av disse for fremstilling av et medikament for behandling av sykdommer som er tilknyttet en mikrogliaaktivering - Google Patents
Benzimidazoler, farmasoytisk preparat og anvendelse av disse for fremstilling av et medikament for behandling av sykdommer som er tilknyttet en mikrogliaaktivering Download PDFInfo
- Publication number
- 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
- Authority
- NO
- Norway
- Prior art keywords
- benzimidazol
- oxy
- phenyl
- methyl ester
- acid methyl
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title claims abstract description 10
- 150000001556 benzimidazoles Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 210000000274 microglia Anatomy 0.000 title abstract description 14
- 230000004913 activation Effects 0.000 title abstract description 9
- 201000010099 disease Diseases 0.000 title description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 123
- -1 methanediylbisoxy Chemical group 0.000 claims description 118
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 claims description 113
- 150000004702 methyl esters Chemical class 0.000 claims description 89
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 21
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 21
- 230000006724 microglial activation Effects 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- JSHDAORXSNJOBA-UHFFFAOYSA-N Isopropyl hexanoate Chemical compound CCCCCC(=O)OC(C)C JSHDAORXSNJOBA-UHFFFAOYSA-N 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- RFNXOSMCFKSBMU-UHFFFAOYSA-N methyl 6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C(C)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 RFNXOSMCFKSBMU-UHFFFAOYSA-N 0.000 claims description 8
- HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- FDQBUDXZZQHOPI-UHFFFAOYSA-N 1-(3-chlorophenyl)-6-hexoxy-2-phenylbenzimidazole Chemical compound CCCCCCOC1=CC2=C(C=C1)N=C(N2C3=CC(=CC=C3)Cl)C4=CC=CC=C4 FDQBUDXZZQHOPI-UHFFFAOYSA-N 0.000 claims description 6
- VPXKBNAVTYQZSV-UHFFFAOYSA-N methyl 6-[2-phenyl-3-[3-(trifluoromethyl)phenyl]benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC(C(F)(F)F)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 VPXKBNAVTYQZSV-UHFFFAOYSA-N 0.000 claims description 6
- KXLUVXKJSNATGT-UHFFFAOYSA-N 6-hexoxy-1-(3-methylphenyl)-2-phenylbenzimidazole Chemical compound CCCCCCOC1=CC2=C(C=C1)N=C(N2C3=CC=CC(=C3)C)C4=CC=CC=C4 KXLUVXKJSNATGT-UHFFFAOYSA-N 0.000 claims description 5
- YDZYKHYTSRCKLU-UHFFFAOYSA-N 6-hexoxy-2-(4-methylphenyl)-1-phenylbenzimidazole Chemical compound CC1=CC=C(C=C1)C1=NC2=C(N1C1=CC=CC=C1)C=C(C=C2)OCCCCCC YDZYKHYTSRCKLU-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 230000006806 disease prevention Effects 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- MXZVNYAJOLUNGC-UHFFFAOYSA-N methyl 2-(2,3-diphenylbenzimidazol-5-yl)oxyacetate Chemical compound C=1C=CC=CC=1N1C2=CC(OCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 MXZVNYAJOLUNGC-UHFFFAOYSA-N 0.000 claims description 5
- HGWNOVOCQCIYIL-UHFFFAOYSA-N methyl 6-(2,3-diphenylbenzimidazol-5-yl)oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 HGWNOVOCQCIYIL-UHFFFAOYSA-N 0.000 claims description 5
- JQSWNMRUYCTSQW-UHFFFAOYSA-N methyl 6-[3-(1,3-benzodioxol-5-yl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C2OCOC2=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 JQSWNMRUYCTSQW-UHFFFAOYSA-N 0.000 claims description 5
- RERXTHPSQOFDBN-UHFFFAOYSA-N methyl 6-[3-(3,4-dimethoxyphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(OC)C(OC)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 RERXTHPSQOFDBN-UHFFFAOYSA-N 0.000 claims description 5
- PGTVLPZOSZIMIQ-UHFFFAOYSA-N propan-2-yl 6-[6-hydroxy-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C=2C=C(O)C(OCCCCCC(=O)OC(C)C)=CC=2N(C=2C=CC(C)=CC=2)C=1C1=CC=CC=C1 PGTVLPZOSZIMIQ-UHFFFAOYSA-N 0.000 claims description 5
- PUKNULLFRQPICT-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-hexoxy-1-phenylbenzimidazole Chemical compound ClC1=CC=C(C=C1)C1=NC2=C(N1C1=CC=CC=C1)C=C(C=C2)OCCCCCC PUKNULLFRQPICT-UHFFFAOYSA-N 0.000 claims description 4
- FEGMXVYXGWGNCH-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxyhexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)N)=CC=C2N=C1C1=CC=CC=C1 FEGMXVYXGWGNCH-UHFFFAOYSA-N 0.000 claims description 4
- KXLVUPHAFOESOH-UHFFFAOYSA-N 6-hexoxy-1-(4-methylphenyl)-2-phenylbenzimidazole Chemical compound CC1=CC=C(C=C1)N1C(=NC2=C1C=C(C=C2)OCCCCCC)C1=CC=CC=C1 KXLVUPHAFOESOH-UHFFFAOYSA-N 0.000 claims description 4
- AZVAEOBTYLBLHI-UHFFFAOYSA-N C(CCCCC)OC=1C=CC2=C(N(C(=N2)C2=CC=CC=C2)C2=CC(=CC=C2)[N+](=O)[O-])C1 Chemical compound C(CCCCC)OC=1C=CC2=C(N(C(=N2)C2=CC=CC=C2)C2=CC(=CC=C2)[N+](=O)[O-])C1 AZVAEOBTYLBLHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- JCCIXIBHAPLZRY-UHFFFAOYSA-N ethyl 4-(2,3-diphenylbenzimidazol-5-yl)oxybutanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCC(=O)OCC)=CC=C2N=C1C1=CC=CC=C1 JCCIXIBHAPLZRY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- KLTVKGWQXWLMIN-UHFFFAOYSA-N methyl 5-(2,3-diphenylbenzimidazol-5-yl)oxypentanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 KLTVKGWQXWLMIN-UHFFFAOYSA-N 0.000 claims description 4
- LMWWFXKLCHCHDR-UHFFFAOYSA-N methyl 5-[3-(3-acetamidophenyl)-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=CC(NC(C)=O)=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 LMWWFXKLCHCHDR-UHFFFAOYSA-N 0.000 claims description 4
- SEHYRKTVIUOQBX-UHFFFAOYSA-N methyl 5-[3-(3-aminophenyl)-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=CC(N)=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 SEHYRKTVIUOQBX-UHFFFAOYSA-N 0.000 claims description 4
- BXEJAXJRBGUOQS-UHFFFAOYSA-N methyl 5-[3-(3-nitrophenyl)-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=CC([N+]([O-])=O)=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 BXEJAXJRBGUOQS-UHFFFAOYSA-N 0.000 claims description 4
- WUWSUSLUAMOOLG-UHFFFAOYSA-N methyl 5-[3-(4-acetamidophenyl)-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=C(NC(C)=O)C=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 WUWSUSLUAMOOLG-UHFFFAOYSA-N 0.000 claims description 4
- URQWHIZPMMZRAG-UHFFFAOYSA-N methyl 5-[3-(4-aminophenyl)-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=C(N)C=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 URQWHIZPMMZRAG-UHFFFAOYSA-N 0.000 claims description 4
- YPCBBZMKDAZPTJ-UHFFFAOYSA-N methyl 5-[3-(4-nitrophenyl)-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 YPCBBZMKDAZPTJ-UHFFFAOYSA-N 0.000 claims description 4
- PGAJGZTYOYRXOB-UHFFFAOYSA-N methyl 5-[3-[4-[(4-chlorophenyl)sulfonylamino]phenyl]-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=C(NS(=O)(=O)C=2C=CC(Cl)=CC=2)C=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 PGAJGZTYOYRXOB-UHFFFAOYSA-N 0.000 claims description 4
- WJCUFVBKEXDHRG-UHFFFAOYSA-N methyl 5-[6-[(4-chlorophenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxypentanoate Chemical compound COC(=O)CCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 WJCUFVBKEXDHRG-UHFFFAOYSA-N 0.000 claims description 4
- INVORRHQNXUXIP-UHFFFAOYSA-N methyl 6-[2-phenyl-3-(3,4,5-trimethoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C(OC)=C(OC)C(OC)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 INVORRHQNXUXIP-UHFFFAOYSA-N 0.000 claims description 4
- PAPLLBZDZFPZBX-UHFFFAOYSA-N methyl 6-[3-(3,5-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C(C)=CC(C)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 PAPLLBZDZFPZBX-UHFFFAOYSA-N 0.000 claims description 4
- RWYBKKPNKFBPLN-UHFFFAOYSA-N methyl 6-[6-[(4-chlorophenyl)sulfonylamino]-3-(4-methoxyphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=CC(OC)=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 RWYBKKPNKFBPLN-UHFFFAOYSA-N 0.000 claims description 4
- GDBVEWZRSDIRMT-UHFFFAOYSA-N methyl 7-(2,3-diphenylbenzimidazol-5-yl)oxyheptanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 GDBVEWZRSDIRMT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- YSVKSJDCSPBERW-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-1-pyrrolidin-1-ylhexan-1-one Chemical compound C1CCCN1C(=O)CCCCCOC(C=C1N2C=3C=CC=CC=3)=CC=C1N=C2C1=CC=CC=C1 YSVKSJDCSPBERW-UHFFFAOYSA-N 0.000 claims description 3
- KRUMMOMADKVYQX-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n,n-bis(2-methoxyethyl)hexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)N(CCOC)CCOC)=CC=C2N=C1C1=CC=CC=C1 KRUMMOMADKVYQX-UHFFFAOYSA-N 0.000 claims description 3
- KNCQGDLFQFHSQB-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n,n-dimethylhexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)N(C)C)=CC=C2N=C1C1=CC=CC=C1 KNCQGDLFQFHSQB-UHFFFAOYSA-N 0.000 claims description 3
- YYNYJQSHGOGTNF-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-(2-methoxyethyl)hexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)NCCOC)=CC=C2N=C1C1=CC=CC=C1 YYNYJQSHGOGTNF-UHFFFAOYSA-N 0.000 claims description 3
- HNRXWEBIUKRBGJ-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-(2-methylpropyl)hexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)NCC(C)C)=CC=C2N=C1C1=CC=CC=C1 HNRXWEBIUKRBGJ-UHFFFAOYSA-N 0.000 claims description 3
- GXEZTLZPCAYDIX-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-(3-methoxypropyl)hexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=CC=C1 GXEZTLZPCAYDIX-UHFFFAOYSA-N 0.000 claims description 3
- QGAONDXFYWAUAL-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-(3-methylbutyl)hexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)NCCC(C)C)=CC=C2N=C1C1=CC=CC=C1 QGAONDXFYWAUAL-UHFFFAOYSA-N 0.000 claims description 3
- AMTCNFIHRAQAHW-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-hydroxyhexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)NO)=CC=C2N=C1C1=CC=CC=C1 AMTCNFIHRAQAHW-UHFFFAOYSA-N 0.000 claims description 3
- NFTDGZNTVPFCEV-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-methoxyhexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)NOC)=CC=C2N=C1C1=CC=CC=C1 NFTDGZNTVPFCEV-UHFFFAOYSA-N 0.000 claims description 3
- HLPIEKVVCFQLIZ-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-phenylmethoxyhexanamide Chemical compound C=1C=CC=CC=1CONC(=O)CCCCCOC(C=C1N2C=3C=CC=CC=3)=CC=C1N=C2C1=CC=CC=C1 HLPIEKVVCFQLIZ-UHFFFAOYSA-N 0.000 claims description 3
- NHLRLZJKAWVOFS-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-propan-2-ylhexanamide Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)NC(C)C)=CC=C2N=C1C1=CC=CC=C1 NHLRLZJKAWVOFS-UHFFFAOYSA-N 0.000 claims description 3
- HRILJWKYJCZLHO-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-pyridin-2-ylhexanamide Chemical compound C=1C=CC=NC=1NC(=O)CCCCCOC(C=C1N2C=3C=CC=CC=3)=CC=C1N=C2C1=CC=CC=C1 HRILJWKYJCZLHO-UHFFFAOYSA-N 0.000 claims description 3
- YIUJHLCVOWAOQF-UHFFFAOYSA-N 6-(2,3-diphenylbenzimidazol-5-yl)oxy-n-pyridin-3-ylhexanamide Chemical compound C=1C=CN=CC=1NC(=O)CCCCCOC(C=C1N2C=3C=CC=CC=3)=CC=C1N=C2C1=CC=CC=C1 YIUJHLCVOWAOQF-UHFFFAOYSA-N 0.000 claims description 3
- POIKKIYEFXWLQD-UHFFFAOYSA-N 6-[2-phenyl-3-(3,4,5-trimethoxyphenyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound COC1=C(OC)C(OC)=CC(N2C3=CC(OCCCCCC(O)=O)=CC=C3N=C2C=2C=CC=CC=2)=C1 POIKKIYEFXWLQD-UHFFFAOYSA-N 0.000 claims description 3
- NYIJDYGRWDVANM-UHFFFAOYSA-N 6-[3-(1,3-benzodioxol-5-yl)-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound C=1C=C2OCOC2=CC=1N1C2=CC(OCCCCCC(=O)O)=CC=C2N=C1C1=CC=CC=C1 NYIJDYGRWDVANM-UHFFFAOYSA-N 0.000 claims description 3
- UQVDLNYDRJBINC-UHFFFAOYSA-N 6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxy-n,n-diethylhexanamide Chemical compound C=1C=C(C)C(C)=CC=1N1C2=CC(OCCCCCC(=O)N(CC)CC)=CC=C2N=C1C1=CC=CC=C1 UQVDLNYDRJBINC-UHFFFAOYSA-N 0.000 claims description 3
- WTJDOXJXFVDIIQ-UHFFFAOYSA-N 6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxy-n,n-dimethylhexanamide Chemical compound C=1C=C(C)C(C)=CC=1N1C2=CC(OCCCCCC(=O)N(C)C)=CC=C2N=C1C1=CC=CC=C1 WTJDOXJXFVDIIQ-UHFFFAOYSA-N 0.000 claims description 3
- LHDOIDSKMVSFJH-UHFFFAOYSA-N 6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxy-n-(2-methylpropyl)hexanamide Chemical compound C=1C=C(C)C(C)=CC=1N1C2=CC(OCCCCCC(=O)NCC(C)C)=CC=C2N=C1C1=CC=CC=C1 LHDOIDSKMVSFJH-UHFFFAOYSA-N 0.000 claims description 3
- SRQTXEQOMSQTCG-UHFFFAOYSA-N 6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxy-n-(2-pyridin-2-ylethyl)hexanamide Chemical compound C1=C(C)C(C)=CC=C1N1C2=CC(OCCCCCC(=O)NCCC=3N=CC=CC=3)=CC=C2N=C1C1=CC=CC=C1 SRQTXEQOMSQTCG-UHFFFAOYSA-N 0.000 claims description 3
- BYDWJPVEUFFKDX-UHFFFAOYSA-N 6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxy-n-(3-imidazol-1-ylpropyl)hexanamide Chemical compound C1=C(C)C(C)=CC=C1N1C2=CC(OCCCCCC(=O)NCCCN3C=NC=C3)=CC=C2N=C1C1=CC=CC=C1 BYDWJPVEUFFKDX-UHFFFAOYSA-N 0.000 claims description 3
- PMSZDJJDXPLGKR-UHFFFAOYSA-N 6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxy-n-propan-2-ylhexanamide Chemical compound C=1C=C(C)C(C)=CC=1N1C2=CC(OCCCCCC(=O)NC(C)C)=CC=C2N=C1C1=CC=CC=C1 PMSZDJJDXPLGKR-UHFFFAOYSA-N 0.000 claims description 3
- JTWZEOCPWJHJEX-UHFFFAOYSA-N 6-[3-(3-cyanophenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound C=1C=CC(C#N)=CC=1N1C2=CC(OCCCCCC(=O)O)=CC=C2N=C1C1=CC=CC=C1 JTWZEOCPWJHJEX-UHFFFAOYSA-N 0.000 claims description 3
- JWNMDHIDOVRTCA-UHFFFAOYSA-N methyl 2-(2,3-diphenylbenzimidazol-5-yl)oxypropanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OC(C)C(=O)OC)=CC=C2N=C1C1=CC=CC=C1 JWNMDHIDOVRTCA-UHFFFAOYSA-N 0.000 claims description 3
- WGXNVLGDJVXBKO-UHFFFAOYSA-N methyl 2-[2-(2,3-diphenylbenzimidazol-5-yl)oxyethoxy]acetate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCOCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 WGXNVLGDJVXBKO-UHFFFAOYSA-N 0.000 claims description 3
- UDBOQYCOKDWLJJ-UHFFFAOYSA-N methyl 3-(2,3-diphenylbenzimidazol-5-yl)oxypropanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 UDBOQYCOKDWLJJ-UHFFFAOYSA-N 0.000 claims description 3
- LLKDCQGWAYWMSZ-UHFFFAOYSA-N methyl 3-[2-(2,3-diphenylbenzimidazol-5-yl)oxyethoxy]propanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCOCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 LLKDCQGWAYWMSZ-UHFFFAOYSA-N 0.000 claims description 3
- KDOUOGWEWOTJIK-UHFFFAOYSA-N methyl 4-(2,3-diphenylbenzimidazol-5-yl)oxybutanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 KDOUOGWEWOTJIK-UHFFFAOYSA-N 0.000 claims description 3
- QENSVDCGBBERGS-UHFFFAOYSA-N methyl 4-[6-[(4-chlorophenyl)sulfonylamino]-3-(4-methoxyphenyl)-2-phenylbenzimidazol-5-yl]oxybutanoate Chemical compound COC(=O)CCCOC1=CC=2N(C=3C=CC(OC)=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 QENSVDCGBBERGS-UHFFFAOYSA-N 0.000 claims description 3
- XDWPCFAYRMOPRH-UHFFFAOYSA-N methyl 5-[3-[3-[(4-chlorophenyl)sulfonylamino]phenyl]-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound C=1C=CC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC=1N1C2=CC(OCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 XDWPCFAYRMOPRH-UHFFFAOYSA-N 0.000 claims description 3
- REIOHTAWSGTTLA-UHFFFAOYSA-N methyl 6-(2-phenyl-3-thiophen-3-ylbenzimidazol-5-yl)oxyhexanoate Chemical compound C1=CSC=C1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 REIOHTAWSGTTLA-UHFFFAOYSA-N 0.000 claims description 3
- FMMBSHYDOYJHLP-UHFFFAOYSA-N methyl 6-[2-(1H-indol-3-yl)-3-(4-methylphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C12=CC(OCCCCCC(=O)OC)=CC=C2N=C(C=2C3=CC=CC=C3NC=2)N1C1=CC=C(C)C=C1 FMMBSHYDOYJHLP-UHFFFAOYSA-N 0.000 claims description 3
- XPGUTRYTNLKPGC-UHFFFAOYSA-N methyl 6-[2-(furan-2-yl)-3-(4-methylphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CO1 XPGUTRYTNLKPGC-UHFFFAOYSA-N 0.000 claims description 3
- IRIKEUTYGNCYCE-UHFFFAOYSA-N methyl 6-[3-(4-chlorophenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(Cl)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 IRIKEUTYGNCYCE-UHFFFAOYSA-N 0.000 claims description 3
- WMDRDOMEJXKXIX-UHFFFAOYSA-N methyl 6-[3-(4-methylphenyl)-2-(3-methylthiophen-2-yl)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C=1SC=CC=1C WMDRDOMEJXKXIX-UHFFFAOYSA-N 0.000 claims description 3
- PCNPQEIGDFDVNP-UHFFFAOYSA-N methyl 6-[3-(4-methylphenyl)-2-(5-methylthiophen-2-yl)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(C)S1 PCNPQEIGDFDVNP-UHFFFAOYSA-N 0.000 claims description 3
- COJXDRKAMPMOHV-UHFFFAOYSA-N methyl 6-[3-(4-methylphenyl)-2-pyridin-3-ylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CN=C1 COJXDRKAMPMOHV-UHFFFAOYSA-N 0.000 claims description 3
- NIWAULOWDPYIPX-UHFFFAOYSA-N methyl 6-[3-(4-methylphenyl)-2-thiophen-3-ylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C=1C=CSC=1 NIWAULOWDPYIPX-UHFFFAOYSA-N 0.000 claims description 3
- AXLVMAYWKKVFQW-UHFFFAOYSA-N methyl 6-[3-[4-(dimethylamino)phenyl]-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(N(C)C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 AXLVMAYWKKVFQW-UHFFFAOYSA-N 0.000 claims description 3
- VBLOAZSBAOOKCW-UHFFFAOYSA-N methyl 6-[6-[(4-chlorophenyl)sulfonylamino]-2,3-bis(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=CC(OC)=CC=3)C(C=3C=CC(OC)=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 VBLOAZSBAOOKCW-UHFFFAOYSA-N 0.000 claims description 3
- XYLPHRHRWNZGDH-UHFFFAOYSA-N methyl 6-[6-[(4-chlorophenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 XYLPHRHRWNZGDH-UHFFFAOYSA-N 0.000 claims description 3
- DWKOAPRDQPMUCB-UHFFFAOYSA-N methyl 6-[6-[(4-chlorophenyl)sulfonylamino]-2-(4-fluorophenyl)-3-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=CC(OC)=CC=3)C(C=3C=CC(F)=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 DWKOAPRDQPMUCB-UHFFFAOYSA-N 0.000 claims description 3
- HORUWDOGUPFRQK-UHFFFAOYSA-N methyl 6-[6-methoxy-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C=2C=C(OC)C(OCCCCCC(=O)OC)=CC=2N(C=2C=CC(C)=CC=2)C=1C1=CC=CC=C1 HORUWDOGUPFRQK-UHFFFAOYSA-N 0.000 claims description 3
- NLHIWDDWLQVYJI-UHFFFAOYSA-N n-cyclopropyl-6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanamide Chemical compound C1=C(C)C(C)=CC=C1N1C2=CC(OCCCCCC(=O)NC3CC3)=CC=C2N=C1C1=CC=CC=C1 NLHIWDDWLQVYJI-UHFFFAOYSA-N 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- MIEUUFBAFGUENF-UHFFFAOYSA-N propan-2-yl 2-(2,3-diphenylbenzimidazol-5-yl)oxyacetate Chemical compound C=1C=CC=CC=1N1C2=CC(OCC(=O)OC(C)C)=CC=C2N=C1C1=CC=CC=C1 MIEUUFBAFGUENF-UHFFFAOYSA-N 0.000 claims description 3
- DBDXLOKNCMMXRC-UHFFFAOYSA-N propan-2-yl 4-(2,3-diphenylbenzimidazol-5-yl)oxybutanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCC(=O)OC(C)C)=CC=C2N=C1C1=CC=CC=C1 DBDXLOKNCMMXRC-UHFFFAOYSA-N 0.000 claims description 3
- FDACWRLZQSAANA-UHFFFAOYSA-N propan-2-yl 5-(2,3-diphenylbenzimidazol-5-yl)oxypentanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCC(=O)OC(C)C)=CC=C2N=C1C1=CC=CC=C1 FDACWRLZQSAANA-UHFFFAOYSA-N 0.000 claims description 3
- MGUCDFLRIJAIAR-UHFFFAOYSA-N propan-2-yl 6-(2,3-diphenylbenzimidazol-5-yl)oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)OC(C)C)=CC=C2N=C1C1=CC=CC=C1 MGUCDFLRIJAIAR-UHFFFAOYSA-N 0.000 claims description 3
- WJECVPDLIAEBNL-UHFFFAOYSA-N propan-2-yl 6-(6-nitro-2,3-diphenylbenzimidazol-5-yl)oxyhexanoate Chemical compound N=1C=2C=C([N+]([O-])=O)C(OCCCCCC(=O)OC(C)C)=CC=2N(C=2C=CC=CC=2)C=1C1=CC=CC=C1 WJECVPDLIAEBNL-UHFFFAOYSA-N 0.000 claims description 3
- KQTITEXSJGVKEY-UHFFFAOYSA-N propan-2-yl 6-[2,3-diphenyl-6-(propylsulfonylamino)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1N1C=2C=C(OCCCCCC(=O)OC(C)C)C(NS(=O)(=O)CCC)=CC=2N=C1C1=CC=CC=C1 KQTITEXSJGVKEY-UHFFFAOYSA-N 0.000 claims description 3
- RGGZQODDCBKXJH-UHFFFAOYSA-N propan-2-yl 6-[2-phenyl-3-[3-(trifluoromethyl)phenyl]benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC(C(F)(F)F)=CC=1N1C2=CC(OCCCCCC(=O)OC(C)C)=CC=C2N=C1C1=CC=CC=C1 RGGZQODDCBKXJH-UHFFFAOYSA-N 0.000 claims description 3
- ITSHNVMFHJVLMS-UHFFFAOYSA-N propan-2-yl 6-[6-(benzylsulfonylamino)-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound CC(C)OC(=O)CCCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)CC1=CC=CC=C1 ITSHNVMFHJVLMS-UHFFFAOYSA-N 0.000 claims description 3
- ZRFMFJADYWIXDD-UHFFFAOYSA-N propan-2-yl 6-[6-[(3-methylphenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound CC(C)OC(=O)CCCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=CC(C)=C1 ZRFMFJADYWIXDD-UHFFFAOYSA-N 0.000 claims description 3
- NHWVTVYSQLWRDD-UHFFFAOYSA-N propan-2-yl 6-[6-[(4-acetamidophenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound CC(C)OC(=O)CCCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 NHWVTVYSQLWRDD-UHFFFAOYSA-N 0.000 claims description 3
- OZUBQADOBUSGNF-UHFFFAOYSA-N propan-2-yl 6-[6-[(4-bromophenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound CC(C)OC(=O)CCCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Br)C=C1 OZUBQADOBUSGNF-UHFFFAOYSA-N 0.000 claims description 3
- KUNDYVSSAOQRFF-UHFFFAOYSA-N propan-2-yl 6-[6-[(4-methoxyphenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(C(=C1)OCCCCCC(=O)OC(C)C)=CC2=C1N(C=1C=CC=CC=1)C(C=1C=CC=CC=1)=N2 KUNDYVSSAOQRFF-UHFFFAOYSA-N 0.000 claims description 3
- OSZLGKYAUHAZST-UHFFFAOYSA-N propan-2-yl 6-[6-[(4-methylphenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound CC(C)OC(=O)CCCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(C)C=C1 OSZLGKYAUHAZST-UHFFFAOYSA-N 0.000 claims description 3
- DYPNXVYESDZSGH-UHFFFAOYSA-N propan-2-yl 6-[6-methoxy-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C=2C=C(OCCCCCC(=O)OC(C)C)C(OC)=CC=2N=C1C1=CC=CC=C1 DYPNXVYESDZSGH-UHFFFAOYSA-N 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- CXEJSLKQRIKBSX-UHFFFAOYSA-N 6-[3-[4-(dimethylamino)phenyl]-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound C1=CC(N(C)C)=CC=C1N1C2=CC(OCCCCCC(O)=O)=CC=C2N=C1C1=CC=CC=C1 CXEJSLKQRIKBSX-UHFFFAOYSA-N 0.000 claims description 2
- VVFIAWOXPCAKGK-UHFFFAOYSA-N 6-[7-hydroxy-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound C1=CC(C)=CC=C1N1C2=CC(OCCCCCC(O)=O)=CC(O)=C2N=C1C1=CC=CC=C1 VVFIAWOXPCAKGK-UHFFFAOYSA-N 0.000 claims description 2
- RGUDYGQOBUCJJJ-UHFFFAOYSA-N 6-hexoxy-5-nitro-1,2-diphenylbenzimidazole Chemical compound N=1C=2C=C([N+]([O-])=O)C(OCCCCCC)=CC=2N(C=2C=CC=CC=2)C=1C1=CC=CC=C1 RGUDYGQOBUCJJJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- PXMLRIRZORMIRT-UHFFFAOYSA-N methyl 5-[6-[(4-chlorophenyl)sulfonylamino]-3-(4-methoxyphenyl)-2-phenylbenzimidazol-5-yl]oxypentanoate Chemical compound COC(=O)CCCCOC1=CC=2N(C=3C=CC(OC)=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 PXMLRIRZORMIRT-UHFFFAOYSA-N 0.000 claims description 2
- OOFMFTXJIMEKCA-UHFFFAOYSA-N methyl 6-(2-phenyl-1-thiophen-3-ylbenzimidazol-5-yl)oxyhexanoate Chemical compound C=1C=CC=CC=1C1=NC2=CC(OCCCCCC(=O)OC)=CC=C2N1C=1C=CSC=1 OOFMFTXJIMEKCA-UHFFFAOYSA-N 0.000 claims description 2
- FKMLMEWWVHFKEM-UHFFFAOYSA-N methyl 6-[1-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC(OCCCCCC(=O)OC)=CC=C2N(C=2C=CC(C)=CC=2)C=1C1=CC=CC=C1 FKMLMEWWVHFKEM-UHFFFAOYSA-N 0.000 claims description 2
- YCKBFLWNQNNOMQ-UHFFFAOYSA-N methyl 6-[3-(3-cyanophenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC(C#N)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 YCKBFLWNQNNOMQ-UHFFFAOYSA-N 0.000 claims description 2
- YFTBURXTHKRZHV-UHFFFAOYSA-N methyl 6-[3-(3-methoxyphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC(OC)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 YFTBURXTHKRZHV-UHFFFAOYSA-N 0.000 claims description 2
- DLCQYSANNMPWOL-UHFFFAOYSA-N methyl 6-[3-(4-methoxyphenyl)-2-phenyl-6-[[4-(trifluoromethyl)phenyl]sulfonylamino]benzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=CC(OC)=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 DLCQYSANNMPWOL-UHFFFAOYSA-N 0.000 claims description 2
- PWUNNILXGHRGFF-UHFFFAOYSA-N methyl 6-[3-(4-methoxyphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(OC)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 PWUNNILXGHRGFF-UHFFFAOYSA-N 0.000 claims description 2
- DAJLZUBXISXEDF-UHFFFAOYSA-N methyl 6-[3-(4-methylphenyl)-2-pyridin-4-ylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=NC=C1 DAJLZUBXISXEDF-UHFFFAOYSA-N 0.000 claims description 2
- DKEWEIFOJMGBJM-UHFFFAOYSA-N methyl 6-[4-methyl-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=C(C)C(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 DKEWEIFOJMGBJM-UHFFFAOYSA-N 0.000 claims description 2
- ZVPCRULTTFWXTG-UHFFFAOYSA-N methyl 6-[6-[(4-chlorophenyl)sulfonylamino]-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=CC(C)=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 ZVPCRULTTFWXTG-UHFFFAOYSA-N 0.000 claims description 2
- ONUZHEPICYPYTR-UHFFFAOYSA-N methyl 6-[7-acetyloxy-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC(OC(C)=O)=C2N=C1C1=CC=CC=C1 ONUZHEPICYPYTR-UHFFFAOYSA-N 0.000 claims description 2
- XJTTWRRIEISWCN-UHFFFAOYSA-N methyl 6-[7-hydroxy-3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC(O)=C2N=C1C1=CC=CC=C1 XJTTWRRIEISWCN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- UQGCBUZMSVDCIP-UHFFFAOYSA-N n-phenylmethoxy-6-[2-phenyl-3-(3,4,5-trimethoxyphenyl)benzimidazol-5-yl]oxyhexanamide Chemical compound COC1=C(OC)C(OC)=CC(N2C3=CC(OCCCCCC(=O)NOCC=4C=CC=CC=4)=CC=C3N=C2C=2C=CC=CC=2)=C1 UQGCBUZMSVDCIP-UHFFFAOYSA-N 0.000 claims description 2
- QFHPZIXADVODLR-UHFFFAOYSA-N n-tert-butyl-6-[3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanamide Chemical compound C1=C(C)C(C)=CC=C1N1C2=CC(OCCCCCC(=O)NC(C)(C)C)=CC=C2N=C1C1=CC=CC=C1 QFHPZIXADVODLR-UHFFFAOYSA-N 0.000 claims description 2
- AZMPKXREGNZROU-UHFFFAOYSA-N propan-2-yl 6-[2-phenyl-3-(3,4,5-trimethoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound COC1=C(OC)C(OC)=CC(N2C3=CC(OCCCCCC(=O)OC(C)C)=CC=C3N=C2C=2C=CC=CC=2)=C1 AZMPKXREGNZROU-UHFFFAOYSA-N 0.000 claims description 2
- WHMNXRAEIBAFRM-UHFFFAOYSA-N propan-2-yl 6-[3-(3,5-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C(C)=CC(C)=CC=1N1C2=CC(OCCCCCC(=O)OC(C)C)=CC=C2N=C1C1=CC=CC=C1 WHMNXRAEIBAFRM-UHFFFAOYSA-N 0.000 claims description 2
- BYYBWGXWFPOUMQ-UHFFFAOYSA-N propan-2-yl 6-[3-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC(C)C)=CC=C2N=C1C1=CC=CC=C1 BYYBWGXWFPOUMQ-UHFFFAOYSA-N 0.000 claims description 2
- WVXPYFGCAONFRA-UHFFFAOYSA-N propan-2-yl 6-[6-[(4-chlorophenyl)sulfonylamino]-2,3-diphenylbenzimidazol-5-yl]oxyhexanoate Chemical compound CC(C)OC(=O)CCCCCOC1=CC=2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 WVXPYFGCAONFRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- FKOBIZYCAAOLRD-UHFFFAOYSA-N 6-[3-(2,3-dihydro-1h-inden-5-yl)-2-phenylbenzimidazol-5-yl]oxy-n-(3-methoxypropyl)heptanamide Chemical compound C=1C=C2CCCC2=CC=1N1C2=CC(OC(C)CCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=CC=C1 FKOBIZYCAAOLRD-UHFFFAOYSA-N 0.000 claims 1
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- HKRJWXIPSUYLHF-UHFFFAOYSA-N methyl 6-(3-phenyl-2-pyridin-4-ylbenzimidazol-5-yl)oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=NC=C1 HKRJWXIPSUYLHF-UHFFFAOYSA-N 0.000 description 1
- RGSICFGFEBXYNK-UHFFFAOYSA-N methyl 6-(4-amino-2,3-diphenylbenzimidazol-5-yl)oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=C(N)C(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 RGSICFGFEBXYNK-UHFFFAOYSA-N 0.000 description 1
- WCTSPDHVNPEYOT-UHFFFAOYSA-N methyl 6-(6-nitro-2,3-diphenylbenzimidazol-5-yl)oxyhexanoate Chemical compound N=1C=2C=C([N+]([O-])=O)C(OCCCCCC(=O)OC)=CC=2N(C=2C=CC=CC=2)C=1C1=CC=CC=C1 WCTSPDHVNPEYOT-UHFFFAOYSA-N 0.000 description 1
- WRYPKFHXYFCHJZ-UHFFFAOYSA-N methyl 6-[(1,2-diphenylbenzimidazol-5-yl)-(4-fluorophenyl)sulfonylamino]hexanoate Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(CCCCCC(=O)OC)C(C=C1N=2)=CC=C1N(C=1C=CC=CC=1)C=2C1=CC=CC=C1 WRYPKFHXYFCHJZ-UHFFFAOYSA-N 0.000 description 1
- JWXXLLHJAHQTPD-UHFFFAOYSA-N methyl 6-[(1,2-diphenylbenzimidazol-5-yl)-[4-(trifluoromethyl)phenyl]sulfonylamino]hexanoate Chemical compound C=1C=C(C(F)(F)F)C=CC=1S(=O)(=O)N(CCCCCC(=O)OC)C(C=C1N=2)=CC=C1N(C=1C=CC=CC=1)C=2C1=CC=CC=C1 JWXXLLHJAHQTPD-UHFFFAOYSA-N 0.000 description 1
- BETVORSKUBWGMB-UHFFFAOYSA-N methyl 6-[(4-chlorophenyl)sulfonyl-[1-(4-methoxyphenyl)-2-phenylbenzimidazol-5-yl]amino]hexanoate Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N(CCCCCC(=O)OC)C(C=C1N=2)=CC=C1N(C=1C=CC(OC)=CC=1)C=2C1=CC=CC=C1 BETVORSKUBWGMB-UHFFFAOYSA-N 0.000 description 1
- VAAOJEJSCZLPLW-UHFFFAOYSA-N methyl 6-[2-(3-methylphenyl)-3-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC(C)=C1 VAAOJEJSCZLPLW-UHFFFAOYSA-N 0.000 description 1
- HSEMLVKKZQDNME-UHFFFAOYSA-N methyl 6-[2-(4-bromothiophen-2-yl)-3-(4-methylphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC(Br)=CS1 HSEMLVKKZQDNME-UHFFFAOYSA-N 0.000 description 1
- QRRIDHCTCVKYDW-UHFFFAOYSA-N methyl 6-[2-(4-fluorophenyl)-3-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(F)C=C1 QRRIDHCTCVKYDW-UHFFFAOYSA-N 0.000 description 1
- CGZGGUBJIQJRNK-UHFFFAOYSA-N methyl 6-[2-(4-nitrophenyl)-3-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C([N+]([O-])=O)C=C1 CGZGGUBJIQJRNK-UHFFFAOYSA-N 0.000 description 1
- OYOPIFSKVKXWJJ-UHFFFAOYSA-N methyl 6-[3-(1,3-benzodioxol-5-ylamino)-4-nitrophenoxy]hexanoate Chemical compound COC(=O)CCCCCOC1=CC=C([N+]([O-])=O)C(NC=2C=C3OCOC3=CC=2)=C1 OYOPIFSKVKXWJJ-UHFFFAOYSA-N 0.000 description 1
- LRTDIMNMUSSTPW-UHFFFAOYSA-N methyl 6-[3-(2,3-dihydro-1h-inden-5-yl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C2CCCC2=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 LRTDIMNMUSSTPW-UHFFFAOYSA-N 0.000 description 1
- NASJWZHAHYEWQY-UHFFFAOYSA-N methyl 6-[3-(3-fluorophenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC(F)=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 NASJWZHAHYEWQY-UHFFFAOYSA-N 0.000 description 1
- BBQMUYLGLLHQNN-UHFFFAOYSA-N methyl 6-[3-(4-methoxyanilino)-4-nitrophenoxy]hexanoate Chemical compound COC(=O)CCCCCOC1=CC=C([N+]([O-])=O)C(NC=2C=CC(OC)=CC=2)=C1 BBQMUYLGLLHQNN-UHFFFAOYSA-N 0.000 description 1
- VLLURYIWFDAFMF-UHFFFAOYSA-N methyl 6-[3-(9h-fluoren-2-ylamino)-4-nitrophenoxy]hexanoate Chemical compound COC(=O)CCCCCOC1=CC=C([N+]([O-])=O)C(NC=2C=C3C(C4=CC=CC=C4C3)=CC=2)=C1 VLLURYIWFDAFMF-UHFFFAOYSA-N 0.000 description 1
- KHVDQMCNNJEBPY-UHFFFAOYSA-N methyl 6-[3-phenyl-2-[3-(trifluoromethyl)phenyl]benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC(C(F)(F)F)=C1 KHVDQMCNNJEBPY-UHFFFAOYSA-N 0.000 description 1
- ZXILCHWTLZKPTM-UHFFFAOYSA-N methyl 6-[4-nitro-3-(3,4,5-trimethoxyanilino)phenoxy]hexanoate Chemical compound COC(=O)CCCCCOC1=CC=C([N+]([O-])=O)C(NC=2C=C(OC)C(OC)=C(OC)C=2)=C1 ZXILCHWTLZKPTM-UHFFFAOYSA-N 0.000 description 1
- IYXIZVWHTPGVEB-UHFFFAOYSA-N methyl 6-[6-[(4-chlorophenyl)sulfonylamino]-3-(3,4-dimethylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=C(C)C(C)=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 IYXIZVWHTPGVEB-UHFFFAOYSA-N 0.000 description 1
- VZKQHOYDUVYDMH-UHFFFAOYSA-N methyl 6-[6-[(4-chlorophenyl)sulfonylmethylamino]-3-(4-methoxyphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound COC(=O)CCCCCOC1=CC=2N(C=3C=CC(OC)=CC=3)C(C=3C=CC=CC=3)=NC=2C=C1NCS(=O)(=O)C1=CC=C(Cl)C=C1 VZKQHOYDUVYDMH-UHFFFAOYSA-N 0.000 description 1
- MBEVKXZVDTUGPF-UHFFFAOYSA-N methyl 6-[6-methoxy-1-(4-methylphenyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=C(C)C=CC=1N1C=2C=C(OC)C(OCCCCCC(=O)OC)=CC=2N=C1C1=CC=CC=C1 MBEVKXZVDTUGPF-UHFFFAOYSA-N 0.000 description 1
- YFWHEIZKKCJTLJ-UHFFFAOYSA-N methyl 7-(2,3-diphenylbenzimidazol-5-yl)heptanoate Chemical compound C=1C=CC=CC=1N1C2=CC(CCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 YFWHEIZKKCJTLJ-UHFFFAOYSA-N 0.000 description 1
- PNMHIIWTNWOKCP-UHFFFAOYSA-N methyl 7-[(4-chlorophenyl)sulfonyl-(1,2-diphenylbenzimidazol-5-yl)amino]heptanoate Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N(CCCCCCC(=O)OC)C(C=C1N=2)=CC=C1N(C=1C=CC=CC=1)C=2C1=CC=CC=C1 PNMHIIWTNWOKCP-UHFFFAOYSA-N 0.000 description 1
- LBZIMVLYQBXRTB-UHFFFAOYSA-N methyl 8-(2,3-diphenylbenzimidazol-5-yl)oxyoctanoate Chemical compound C=1C=CC=CC=1N1C2=CC(OCCCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 LBZIMVLYQBXRTB-UHFFFAOYSA-N 0.000 description 1
- IZIJRYNUYQXBPG-UHFFFAOYSA-N methyl 8-bromooctanoate Chemical compound COC(=O)CCCCCCCBr IZIJRYNUYQXBPG-UHFFFAOYSA-N 0.000 description 1
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- AHSVQTULXYKAPV-UHFFFAOYSA-N n-(1,2-diphenylbenzimidazol-5-yl)-1-phenylmethanesulfonamide Chemical compound C=1C=C2N(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=NC2=CC=1NS(=O)(=O)CC1=CC=CC=C1 AHSVQTULXYKAPV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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DE10002898 | 2000-01-14 | ||
PCT/EP2001/000334 WO2001051473A1 (de) | 2000-01-14 | 2001-01-12 | 1,2-diarylbenzimidazole zur behandlung von krankungen die mit einer microglia-aktivierung assoziiert sind |
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NO20023362D0 NO20023362D0 (no) | 2002-07-12 |
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DE10134775A1 (de) * | 2001-07-06 | 2003-01-30 | Schering Ag | 1-Alkyl-2.aryl-benzimidazolderivate, deren Verwendung zur Herstellung von Arzneimitteln sowie diese Derivate enthaltende pharmazeutische Präparate |
US6855714B2 (en) | 2001-07-06 | 2005-02-15 | Schering Aktiengesellschaft | 1-alkyl-2-aryl-benzimidazole derivatives, their use for the production of pharmaceutical agents as well as pharmaceutical preparations that contain these derivatives |
DE10135050A1 (de) * | 2001-07-09 | 2003-02-06 | Schering Ag | 1-Ary1-2-N-, S- oder O-substituierte Benzimidazolderivate, deren Verwendung zur Herstellung von Arzneimitteln sowie diese Derivate enthaltende pharmazeutische Präparate |
US6903126B2 (en) | 2001-07-09 | 2005-06-07 | Schering Ag | 1-Aryl-2-N-, S- or O-substituted benzimidazole derivatives, their use for the production of pharmaceutical agents as well as pharmaceutical preparations that contain these derivatives |
US6962932B2 (en) | 2002-02-15 | 2005-11-08 | Schering Aktiengesellschaft | 1-phenyl-2-heteroaryl-substituted benzimdazole derivatives, their use for the production of pharmaceutical agents as well as pharmaceutical preparations that contain these derivatives |
DE10207843A1 (de) * | 2002-02-15 | 2003-09-04 | Schering Ag | Mikrolia-Inhibitoren zur Unterbrechung von Interleukin 12 und IFN-gamma vermittelten Immunreaktionen |
DE10207844A1 (de) * | 2002-02-15 | 2003-09-04 | Schering Ag | 1-Phenyl-2-heteroaryl-substituierte Benzimidazolderivate, deren Verwendung zur Herstellung von Arzneimitteln sowie diese Derivate enthaltende pharmazeutische Präparate |
US7381825B2 (en) * | 2003-03-17 | 2008-06-03 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
SE0302570D0 (sv) * | 2003-09-26 | 2003-09-26 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
SE0302573D0 (sv) * | 2003-09-26 | 2003-09-26 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
KR101269869B1 (ko) | 2004-09-24 | 2013-06-07 | 네오메드 인스티튜트 | 벤즈이미다졸 유도체, 그를 함유하는 조성물, 그의 제조방법 및 그의 용도 |
TW200745049A (en) | 2006-03-23 | 2007-12-16 | Astrazeneca Ab | New crystalline forms |
TW200808769A (en) | 2006-04-18 | 2008-02-16 | Astrazeneca Ab | Therapeutic compounds |
JP5255994B2 (ja) * | 2008-11-04 | 2013-08-07 | 国立大学法人 岡山大学 | 核内受容体リガンド |
WO2012012478A1 (en) * | 2010-07-21 | 2012-01-26 | Merck Sharp & Dohme Corp. | Aldosterone synthase inhibitors |
CN102382102B (zh) * | 2010-09-06 | 2014-01-08 | 中国科学院广州生物医药与健康研究院 | 一种酰胺类化合物 |
CN110698408B (zh) * | 2012-02-17 | 2021-01-05 | 奇尼塔病毒性出血热有限责任公司 | 用于治疗沙粒病毒感染的抗病毒药物 |
WO2014044611A1 (en) | 2012-09-20 | 2014-03-27 | Bayer Pharma Aktiengesellschaft | 1-aryl-2-heteroaryl benzimidazoles for the induction of neuronal regeneration |
MX2018007147A (es) * | 2015-12-15 | 2019-03-28 | Univ Leland Stanford Junior | Metodo para prevenir y/o tratar el daño cognitivo asociado al envejecimiento y la neuroinflamacion. |
JP2022508648A (ja) | 2018-10-05 | 2022-01-19 | アンナプルナ バイオ インコーポレイテッド | Apj受容体活性に関連する状態を処置するための化合物および組成物 |
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US4430502A (en) * | 1982-08-13 | 1984-02-07 | The Upjohn Company | Pyridinyl substituted benzimidazoles and quinoxalines |
DK0520200T3 (da) * | 1991-06-24 | 1998-09-23 | Neurosearch As | Imadazol-forbindelser, deres fremstilling og anvendelse |
MX9203323A (es) * | 1991-07-11 | 1994-07-29 | Hoechst Ag | El empleo de derivados de xantina para el tratamiento de lesiones secundarias de las celulas nerviosas y trastornos funcionales despues de traumas craneo-cerebrales. |
DE4129603A1 (de) * | 1991-09-06 | 1993-03-11 | Thomae Gmbh Dr K | Kondensierte 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE4330959A1 (de) * | 1993-09-09 | 1995-03-16 | Schering Ag | Neue Benzimidazolderivate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
US5552426A (en) * | 1994-04-29 | 1996-09-03 | Eli Lilly And Company | Methods for treating a physiological disorder associated with β-amyloid peptide |
IL113472A0 (en) * | 1994-04-29 | 1995-07-31 | Lilly Co Eli | Non-peptidyl tachykinin receptor antogonists |
AU6966696A (en) * | 1995-10-05 | 1997-04-28 | Warner-Lambert Company | Method for treating and preventing inflammation and atherosclerosis |
WO1997033873A1 (en) * | 1996-03-11 | 1997-09-18 | Eli Lilly And Company | Methods of treating or preventing interstitial cystitis |
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Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE |
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MM1K | Lapsed by not paying the annual fees |