KR20060097024A - 벤조이미다졸 화합물 - Google Patents

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Publication number

KR20060097024A

KR20060097024A KR1020067008435A KR20067008435A KR20060097024A KR 20060097024 A KR20060097024 A KR 20060097024A KR 1020067008435 A KR1020067008435 A KR 1020067008435A KR 20067008435 A KR20067008435 A KR 20067008435A KR 20060097024 A KR20060097024 A KR 20060097024A

Authority

KR

South Korea

Prior art keywords

methyl

benzoimidazole

chloro

propoxy

phenyl

Prior art date

2003-09-30

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• -1 Benzimidazole Compound Chemical class 0.000 title claims description 79
• 238000000034 method Methods 0.000 claims abstract description 204
• 239000000203 mixture Substances 0.000 claims abstract description 195
• 210000000265 leukocyte Anatomy 0.000 claims abstract description 69
• 206010061218 Inflammation Diseases 0.000 claims abstract description 29
• 230000004054 inflammatory process Effects 0.000 claims abstract description 29
• 230000007115 recruitment Effects 0.000 claims abstract description 3
• 150000001875 compounds Chemical class 0.000 claims description 399
• 102000005962 receptors Human genes 0.000 claims description 76
• 108020003175 receptors Proteins 0.000 claims description 76
• 239000008194 pharmaceutical composition Substances 0.000 claims description 74
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 68
• 230000003416 augmentation Effects 0.000 claims description 61
• 125000001424 substituent group Chemical group 0.000 claims description 55
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 40
• 230000001404 mediated effect Effects 0.000 claims description 40
• 230000028709 inflammatory response Effects 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
• 239000003112 inhibitor Substances 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 208000024891 symptom Diseases 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 150000002148 esters Chemical class 0.000 claims description 33
• 230000002401 inhibitory effect Effects 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 229940075993 receptor modulator Drugs 0.000 claims description 32
• 230000004044 response Effects 0.000 claims description 31
• 150000001408 amides Chemical class 0.000 claims description 30
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• 125000004122 cyclic group Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 208000023275 Autoimmune disease Diseases 0.000 claims description 9
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
• 201000010105 allergic rhinitis Diseases 0.000 claims description 9
• 208000006673 asthma Diseases 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• PMSKRMBSAZKNAO-UHFFFAOYSA-N 6-tert-butyl-2-[2-methyl-4-[3-(2-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound CC1CNCCN1CCCOC(C=C1C)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 PMSKRMBSAZKNAO-UHFFFAOYSA-N 0.000 claims description 7
• 206010020751 Hypersensitivity Diseases 0.000 claims description 7
• 230000001363 autoimmune Effects 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 239000003396 histamine H4 receptor antagonist Substances 0.000 claims description 7
• 230000001900 immune effect Effects 0.000 claims description 7
• 230000002757 inflammatory effect Effects 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• HOGIQAJOASEATP-UHFFFAOYSA-N 6-tert-butyl-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl HOGIQAJOASEATP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• QKEMCQCADKOQNJ-UHFFFAOYSA-N 4-methyl-2-[6-[3-(1-methylpiperidin-4-yl)propoxy]pyridin-3-yl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=N1 QKEMCQCADKOQNJ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 206010047115 Vasculitis Diseases 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 208000026935 allergic disease Diseases 0.000 claims description 5
• 201000004339 autoimmune neuropathy Diseases 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• VCIHULUAXLZRNB-UHFFFAOYSA-N 4,6-dimethyl-2-[2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=CC=N1 VCIHULUAXLZRNB-UHFFFAOYSA-N 0.000 claims description 4
• QNIBJIPCXYFDAG-UHFFFAOYSA-N 4,6-dimethyl-2-[2-[4-(4-methylpiperazin-1-yl)butoxy]pyridin-4-yl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCCOC1=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=CC=N1 QNIBJIPCXYFDAG-UHFFFAOYSA-N 0.000 claims description 4
• HEOOSKRYIMADSF-UHFFFAOYSA-N 4-[3-[4-(6-chloro-4-methyl-1h-benzimidazol-2-yl)-3-methylphenoxy]propyl]-1,4-diazepan-5-one Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(C)=CC=1OCCCN1CCNCCC1=O HEOOSKRYIMADSF-UHFFFAOYSA-N 0.000 claims description 4
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
• JESCQINQDIAWHZ-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[3-[3-(1-methylpiperidin-4-yl)oxypropoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1OCCCOC1=CC=CC(C=2NC3=C(C)C(F)=CC=C3N=2)=C1 JESCQINQDIAWHZ-UHFFFAOYSA-N 0.000 claims description 4
• WLWJNOVUEPCFDS-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C(F)=CC=C3N=2)=C1 WLWJNOVUEPCFDS-UHFFFAOYSA-N 0.000 claims description 4
• ZVQKIPPBPPNIJB-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[6-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)propoxy]pyridin-3-yl]-1h-benzimidazole Chemical compound C1N(C)CCC(CCCOC=2N=CC(=CC=2)C=2NC3=CC=C(F)C(C)=C3N=2)=C1 ZVQKIPPBPPNIJB-UHFFFAOYSA-N 0.000 claims description 4
• XQKWWEQHOPMFCD-UHFFFAOYSA-N 6-chloro-4-methyl-2-[2-methyl-4-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1N(C)CCC(CCCOC=2C=C(C)C(C=3NC4=CC(Cl)=CC(C)=C4N=3)=CC=2)=C1 XQKWWEQHOPMFCD-UHFFFAOYSA-N 0.000 claims description 4
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
• 208000038016 acute inflammation Diseases 0.000 claims description 4
• 230000006022 acute inflammation Effects 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 230000009285 allergic inflammation Effects 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 4
• 230000006020 chronic inflammation Effects 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 208000017520 skin disease Diseases 0.000 claims description 4
• WFYUITPFJSNEQQ-UHFFFAOYSA-N 1-[2-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(CN(C)C)=CC=1OCCCC1CCN(C)CC1 WFYUITPFJSNEQQ-UHFFFAOYSA-N 0.000 claims description 3
• AADBANJKFIORNE-UHFFFAOYSA-N 1-[3-[4-(6-tert-butyl-1h-benzimidazol-2-yl)-2-chlorophenoxy]propyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl AADBANJKFIORNE-UHFFFAOYSA-N 0.000 claims description 3
• FGHYEUTXZSFVTI-UHFFFAOYSA-N 2-[2-[4-(1-ethylpiperidin-4-yl)butoxy]pyridin-4-yl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(CC)CCC1CCCCOC1=CC(C=2NC3=CC=C(C)C(C)=C3N=2)=CC=N1 FGHYEUTXZSFVTI-UHFFFAOYSA-N 0.000 claims description 3
• QSSIZKWOJDCWML-UHFFFAOYSA-N 2-[2-chloro-4-[2-methyl-3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=CC(C)=C3N=2)C(Cl)=CC=1OCC(C)CN1CCN(C)CC1 QSSIZKWOJDCWML-UHFFFAOYSA-N 0.000 claims description 3
• CCHJDYXWLQLTHD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 CCHJDYXWLQLTHD-UHFFFAOYSA-N 0.000 claims description 3
• ZBKOPZVHMTXXQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 ZBKOPZVHMTXXQH-UHFFFAOYSA-N 0.000 claims description 3
• BYEFGIKEWXKOAC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 BYEFGIKEWXKOAC-UHFFFAOYSA-N 0.000 claims description 3
• YPWPMKJVTQONQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 YPWPMKJVTQONQH-UHFFFAOYSA-N 0.000 claims description 3
• RPIXQBZODSVPPC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 RPIXQBZODSVPPC-UHFFFAOYSA-N 0.000 claims description 3
• JMQRDCNEFGNPAL-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 JMQRDCNEFGNPAL-UHFFFAOYSA-N 0.000 claims description 3
• WMGUYQXCPREFOF-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 WMGUYQXCPREFOF-UHFFFAOYSA-N 0.000 claims description 3
• PBYAQWILYFZYHC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC=CC=C2N1 PBYAQWILYFZYHC-UHFFFAOYSA-N 0.000 claims description 3
• SKQKGGHCXLOMFJ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 SKQKGGHCXLOMFJ-UHFFFAOYSA-N 0.000 claims description 3
• FKLHKZSFHAZKBD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 FKLHKZSFHAZKBD-UHFFFAOYSA-N 0.000 claims description 3
• SIDSFFAOACXBRD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 SIDSFFAOACXBRD-UHFFFAOYSA-N 0.000 claims description 3
• DIFIANIFCWCWIA-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 DIFIANIFCWCWIA-UHFFFAOYSA-N 0.000 claims description 3
• NPYCKTMZMUAVJW-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-5-fluoro-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(F)=CC=C2N1 NPYCKTMZMUAVJW-UHFFFAOYSA-N 0.000 claims description 3
• NYNGHPOORNFKGZ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(OC(F)(F)F)=CC=C2N1 NYNGHPOORNFKGZ-UHFFFAOYSA-N 0.000 claims description 3
• FEMHOUCJHZSJJV-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C)=CC=C2N1 FEMHOUCJHZSJJV-UHFFFAOYSA-N 0.000 claims description 3
• KHADFEDGWBHJSK-UHFFFAOYSA-N 2-[2-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C(OC)=CC=1OCCCN1CCN(C)CC1 KHADFEDGWBHJSK-UHFFFAOYSA-N 0.000 claims description 3
• KBYGQHKVXVNPHA-UHFFFAOYSA-N 2-[3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(C=2NC3=CC=CC=C3N=2)=C1 KBYGQHKVXVNPHA-UHFFFAOYSA-N 0.000 claims description 3
• YVEXWWVMANPFEX-UHFFFAOYSA-N 2-[3-chloro-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=NC=CC(C=2NC3=CC=C(C)C(C)=C3N=2)=C1Cl YVEXWWVMANPFEX-UHFFFAOYSA-N 0.000 claims description 3
• KMJHRNRFTSIPJB-UHFFFAOYSA-N 2-[3-chloro-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=NC=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=C1Cl KMJHRNRFTSIPJB-UHFFFAOYSA-N 0.000 claims description 3
• NIQZSPRFQZPDAW-UHFFFAOYSA-N 2-[3-chloro-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridin-4-yl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=NC=CC(C=2NC3=CC=CC(C)=C3N=2)=C1Cl NIQZSPRFQZPDAW-UHFFFAOYSA-N 0.000 claims description 3
• BHXFOAZKCRAEEO-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=C1Cl BHXFOAZKCRAEEO-UHFFFAOYSA-N 0.000 claims description 3
• UMNDIUWKZLKSRC-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1Cl UMNDIUWKZLKSRC-UHFFFAOYSA-N 0.000 claims description 3
• ZJSRVCKWBKNRCM-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C=C1Cl ZJSRVCKWBKNRCM-UHFFFAOYSA-N 0.000 claims description 3
• PVHPABJTUPOEHL-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methoxy-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1C(C=C1Cl)=CC=C1OCCCN1CCN(C)CC1 PVHPABJTUPOEHL-UHFFFAOYSA-N 0.000 claims description 3
• QMGSOQRJRHUXGG-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1Cl QMGSOQRJRHUXGG-UHFFFAOYSA-N 0.000 claims description 3
• FOWBFPKYEHZJDX-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1F FOWBFPKYEHZJDX-UHFFFAOYSA-N 0.000 claims description 3
• WXWJVMLNEFLGCC-UHFFFAOYSA-N 2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)=CC=C1OCCCN1CCN(C)CC1 WXWJVMLNEFLGCC-UHFFFAOYSA-N 0.000 claims description 3
• DOLJNIUPEWVSMY-UHFFFAOYSA-N 2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1C DOLJNIUPEWVSMY-UHFFFAOYSA-N 0.000 claims description 3
• KUBYFJXKFPBGHW-UHFFFAOYSA-N 2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1 KUBYFJXKFPBGHW-UHFFFAOYSA-N 0.000 claims description 3
• PSSMSADYPZZWDS-UHFFFAOYSA-N 2-[4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1 PSSMSADYPZZWDS-UHFFFAOYSA-N 0.000 claims description 3
• CZXBEGBIJAJZQD-UHFFFAOYSA-N 2-[4-chloro-6-[3-(1-methylpiperidin-4-yl)propoxy]pyridin-3-yl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC(Cl)=C(C=2NC3=CC(C)=CC(C)=C3N=2)C=N1 CZXBEGBIJAJZQD-UHFFFAOYSA-N 0.000 claims description 3
• JEAOQSCHCZQCLW-UHFFFAOYSA-N 2-[4-chloro-6-[3-(1-methylpiperidin-4-yl)propoxy]pyridin-3-yl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC(Cl)=C(C=2NC3=CC=CC(C)=C3N=2)C=N1 JEAOQSCHCZQCLW-UHFFFAOYSA-N 0.000 claims description 3
• VNYUNJYMRIIELG-UHFFFAOYSA-N 2-[4-methoxy-6-[3-(1-methylpiperidin-4-yl)propoxy]pyridin-3-yl]-4-methyl-1h-benzimidazole Chemical compound N=1C=C(C=2NC3=CC=CC(C)=C3N=2)C(OC)=CC=1OCCCC1CCN(C)CC1 VNYUNJYMRIIELG-UHFFFAOYSA-N 0.000 claims description 3
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