JPWO2022040260A5 - - Google Patents
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- JPWO2022040260A5 JPWO2022040260A5 JP2023512228A JP2023512228A JPWO2022040260A5 JP WO2022040260 A5 JPWO2022040260 A5 JP WO2022040260A5 JP 2023512228 A JP2023512228 A JP 2023512228A JP 2023512228 A JP2023512228 A JP 2023512228A JP WO2022040260 A5 JPWO2022040260 A5 JP WO2022040260A5
- Authority
- JP
- Japan
- Prior art keywords
- benzo
- phenyl
- imidazole
- methylsulfonyl
- methyl
- Prior art date
- 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.)
- Pending
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- -1 6-azabicyclo[3.2.1]octanyl Chemical group 0.000 claims 335
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 17
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 11
- 125000003386 piperidinyl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000003566 oxetanyl group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- AKBSPQGOBVBJSG-UHFFFAOYSA-N 6-[1-(1-cyclobutylazepan-4-yl)piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C(CCC2)CCN2C2CCC2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C AKBSPQGOBVBJSG-UHFFFAOYSA-N 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- ZQNRANLWGBTSBU-UHFFFAOYSA-N 6-[3-fluoro-5-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2=CC(CN(CC3)CCC3N3CCCC3)=CC(F)=C2)=C1 ZQNRANLWGBTSBU-UHFFFAOYSA-N 0.000 claims 3
- 206010016654 Fibrosis Diseases 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 230000004761 fibrosis Effects 0.000 claims 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- YHEMUQAJACMSSG-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[1-(1-propan-2-ylazepan-4-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(CCC1)CCC1N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C YHEMUQAJACMSSG-UHFFFAOYSA-N 0.000 claims 2
- QUBLWLLKALGXHU-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[1-[1-(oxan-4-yl)azepan-4-yl]piperidin-4-yl]benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C(CCC2)CCN2C2CCOCC2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C QUBLWLLKALGXHU-UHFFFAOYSA-N 0.000 claims 2
- FZLUVWMHHGMGEN-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[1-[8-(oxetan-3-yl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C(CC2)CCN2C2CC(CC3)N(C4COC4)C3C2)=C1 FZLUVWMHHGMGEN-UHFFFAOYSA-N 0.000 claims 2
- YKTKBJHTFXLLDK-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]benzimidazole Chemical compound CC(C)N(CC1)CCC1OC(C=C1)=CC=C1C1=CC(C)=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=C1 YKTKBJHTFXLLDK-UHFFFAOYSA-N 0.000 claims 2
- AAKHXOACTWIFMN-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[4-(pyrrolidin-1-ylmethyl)phenyl]benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2=CC=C(CN3CCCC3)C=C2)=C1 AAKHXOACTWIFMN-UHFFFAOYSA-N 0.000 claims 2
- RFKADCXTBAKKDM-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]benzimidazole Chemical compound CC(C)N1CCN(CC(C=C2)=CC=C2C(C=C2C)=CC3=C2N=C(C(C=C2)=CC=C2S(C)(=O)=O)N3C)CC1 RFKADCXTBAKKDM-UHFFFAOYSA-N 0.000 claims 2
- KYWYNOIRUVGMTB-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[4-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]benzimidazole Chemical compound CC1=CC(C2=CC=C(CN(CC3)CCC3N3CCCC3)C=C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C KYWYNOIRUVGMTB-UHFFFAOYSA-N 0.000 claims 2
- IBHTVHWBNLRUTJ-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[4-[1-(oxan-4-yl)piperidin-4-yl]phenyl]benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2=CC=C(C(CC3)CCN3C3CCOCC3)C=C2)=C1 IBHTVHWBNLRUTJ-UHFFFAOYSA-N 0.000 claims 2
- VVGWAAXZNACZAU-UHFFFAOYSA-N 1,4-dimethyl-2-(4-methylsulfonylphenyl)-6-[4-[4-(oxan-4-yl)piperazin-1-yl]phenyl]benzimidazole Chemical compound CC1=CC(C(C=C2)=CC=C2N(CC2)CCN2C2CCOCC2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C VVGWAAXZNACZAU-UHFFFAOYSA-N 0.000 claims 2
- WCBHVBMRFGUWKC-UHFFFAOYSA-N 1,4-dimethyl-6-[1-[(6-methylpyridin-3-yl)methyl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2CCN(CC3=CN=C(C)C=C3)CC2)=C1 WCBHVBMRFGUWKC-UHFFFAOYSA-N 0.000 claims 2
- QTQRMTXFFUHQBV-UHFFFAOYSA-N 1,4-dimethyl-6-[1-[1-(2-methylpropyl)azepan-4-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC(C)CN(CCC1)CCC1N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C QTQRMTXFFUHQBV-UHFFFAOYSA-N 0.000 claims 2
- LNODWVQIQFSUBL-UHFFFAOYSA-N 1,4-dimethyl-6-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C LNODWVQIQFSUBL-UHFFFAOYSA-N 0.000 claims 2
- MHEGOCGLUWZRHL-UHFFFAOYSA-N 1,4-dimethyl-6-[4-(1-methylpiperidin-4-yl)phenyl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2=CC=C(C3CCN(C)CC3)C=C2)=C1 MHEGOCGLUWZRHL-UHFFFAOYSA-N 0.000 claims 2
- ZRZBDOXWYSVYKP-UHFFFAOYSA-N 1,4-dimethyl-6-[4-[1-(2-methylpropyl)piperidin-4-yl]oxyphenyl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC(C)CN(CC1)CCC1OC(C=C1)=CC=C1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C ZRZBDOXWYSVYKP-UHFFFAOYSA-N 0.000 claims 2
- DUTIECSRCVABJQ-UHFFFAOYSA-N 1-[4-[3,7-dimethyl-2-(4-methylsulfonylphenyl)benzimidazol-5-yl]phenyl]-N-ethyl-N-methylpiperidin-4-amine Chemical compound CCN(C)C(CC1)CCN1C(C=C1)=CC=C1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C DUTIECSRCVABJQ-UHFFFAOYSA-N 0.000 claims 2
- YCMYQCWAWZVESD-UHFFFAOYSA-N 1-[[4-[2-(2-fluoro-4-methylsulfonylphenyl)-3-methylbenzimidazol-5-yl]phenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C(C=CC(S(C)(=O)=O)=C2)=C2F)N3C)CC1 YCMYQCWAWZVESD-UHFFFAOYSA-N 0.000 claims 2
- PAMRBVBMZHGJOA-UHFFFAOYSA-N 1-[[4-[2-(3,5-difluorophenyl)-3-methylbenzimidazol-5-yl]phenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C2=CC(F)=CC(F)=C2)N3C)CC1 PAMRBVBMZHGJOA-UHFFFAOYSA-N 0.000 claims 2
- ZJFLJVGEYMRCOW-UHFFFAOYSA-N 1-[[4-[2-(3-fluorophenyl)-3-methylbenzimidazol-5-yl]phenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C2=CC(F)=CC=C2)N3C)CC1 ZJFLJVGEYMRCOW-UHFFFAOYSA-N 0.000 claims 2
- FXWIJZIRAFPDPC-UHFFFAOYSA-N 1-[[4-[2-(4-fluorophenyl)-3-methylbenzimidazol-5-yl]phenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C2=CC=C3N=C(C(C=C4)=CC=C4F)N(C)C3=C2)CC1 FXWIJZIRAFPDPC-UHFFFAOYSA-N 0.000 claims 2
- RTGNBCXMTRJBLL-UHFFFAOYSA-N 1-[[4-[2-(4-methoxyphenyl)-3-methylbenzimidazol-5-yl]phenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C(C=C2)=CC=C2OC)N3C)CC1 RTGNBCXMTRJBLL-UHFFFAOYSA-N 0.000 claims 2
- PIQKOGFGLYWLIZ-UHFFFAOYSA-N 1-[[4-[3,7-dimethyl-2-(4-methylsulfonylphenyl)benzimidazol-5-yl]-2,6-difluorophenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2=CC(F)=C(CN(CC3)CCC3N(C)C)C(F)=C2)=C1 PIQKOGFGLYWLIZ-UHFFFAOYSA-N 0.000 claims 2
- XAJSYUURAXANER-UHFFFAOYSA-N 1-[[4-[3,7-dimethyl-2-(4-methylsulfonylphenyl)benzimidazol-5-yl]-2-fluorophenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2=CC(F)=C(CN(CC3)CCC3N(C)C)C=C2)=C1 XAJSYUURAXANER-UHFFFAOYSA-N 0.000 claims 2
- ICVMCLZNIFRVSC-UHFFFAOYSA-N 1-[[4-[3,7-dimethyl-2-(4-methylsulfonylphenyl)benzimidazol-5-yl]phenyl]methyl]-N,N-dimethylpiperidin-4-amine Chemical compound CC1=CC(C2=CC=C(CN(CC3)CCC3N(C)C)C=C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C ICVMCLZNIFRVSC-UHFFFAOYSA-N 0.000 claims 2
- GJRGZPOKEWLGID-UHFFFAOYSA-N 1-cyclopropyl-4-fluoro-2-(4-methylsulfonylphenyl)-6-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(CC1)CCC1N(CC1)CCC1C(C=C1F)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C1CC1 GJRGZPOKEWLGID-UHFFFAOYSA-N 0.000 claims 2
- VMRZVEQCKULMIE-UHFFFAOYSA-N 1-cyclopropyl-4-fluoro-2-(4-methylsulfonylphenyl)-6-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1F)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C1CC1 VMRZVEQCKULMIE-UHFFFAOYSA-N 0.000 claims 2
- INVPXLUYSUVKJX-UHFFFAOYSA-N 1-cyclopropyl-4-fluoro-2-(4-methylsulfonylphenyl)-6-[1-[8-(oxan-4-yl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CS(C(C=C1)=CC=C1C1=NC(C(F)=CC(C(CC2)CCN2C(CC2CC3)CC3N2C2CCOCC2)=C2)=C2N1C1CC1)(=O)=O INVPXLUYSUVKJX-UHFFFAOYSA-N 0.000 claims 2
- YRNOLZVMUDGKJM-UHFFFAOYSA-N 1-cyclopropyl-4-fluoro-6-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C1=CC(F)=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C3CC3)C2=C1 YRNOLZVMUDGKJM-UHFFFAOYSA-N 0.000 claims 2
- OHDBHEPELYHITQ-UHFFFAOYSA-N 1-cyclopropyl-4-methyl-2-(4-methylsulfonylphenyl)-6-[3-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C3CC3)C2=CC(C2=CC(CN(CC3)CCC3N3CCCC3)=CC=C2)=C1 OHDBHEPELYHITQ-UHFFFAOYSA-N 0.000 claims 2
- XANUTVRVEFVULS-UHFFFAOYSA-N 1-cyclopropyl-4-methyl-2-(4-methylsulfonylphenyl)-6-[4-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]benzimidazole Chemical compound CC1=CC(C2=CC=C(CN(CC3)CCC3N3CCCC3)C=C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C1CC1 XANUTVRVEFVULS-UHFFFAOYSA-N 0.000 claims 2
- IQBAFYLTXKYDRY-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,4-dimethyl-6-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC(OC)=C1OC)N2C IQBAFYLTXKYDRY-UHFFFAOYSA-N 0.000 claims 2
- XIJYKKUWVOAIBL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,4-dimethyl-6-[8-[1-(2-methylpropyl)piperidin-4-yl]-8-azabicyclo[3.2.1]octan-3-yl]benzimidazole Chemical compound CC(C)CN(CC1)CCC1N(C(CC1)C2)C1CC2C1=CC(C)=C2N=C(C(C=C3)=CC(OC)=C3OC)N(C)C2=C1 XIJYKKUWVOAIBL-UHFFFAOYSA-N 0.000 claims 2
- GDLUOQJGPWQLDJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-methyl-6-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]benzimidazole Chemical compound CC(C)CN(CC1)CCC1N(CC1)CCC1C(C=C1)=CC2=C1N=C(C(C=C1)=CC(OC)=C1OC)N2C GDLUOQJGPWQLDJ-UHFFFAOYSA-N 0.000 claims 2
- WMZPIQFIDONNDD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-6-[1-[8-(2-methoxyethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-1,4-dimethylbenzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CC(CC3)N(CCOC)C3C2)=CC2=C1N=C(C(C=C1)=CC(OC)=C1OC)N2C WMZPIQFIDONNDD-UHFFFAOYSA-N 0.000 claims 2
- OBGOWFNVYQEZFZ-UHFFFAOYSA-N 2-(3-fluoro-4-methylsulfonylphenyl)-1,4-dimethyl-6-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C1=CC(C)=C2N=C(C(C=C3)=CC(F)=C3S(C)(=O)=O)N(C)C2=C1 OBGOWFNVYQEZFZ-UHFFFAOYSA-N 0.000 claims 2
- FMUDNQBYKQDMQG-UHFFFAOYSA-N 2-(3-fluoro-4-methylsulfonylphenyl)-1,4-dimethyl-6-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C1=CC(C)=C2N=C(C(C=C3)=CC(F)=C3S(C)(=O)=O)N(C)C2=C1 FMUDNQBYKQDMQG-UHFFFAOYSA-N 0.000 claims 2
- JSSZNPDDQKQNGP-UHFFFAOYSA-N 2-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-6-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-1H-benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC(F)=C1S(C)(=O)=O)N2 JSSZNPDDQKQNGP-UHFFFAOYSA-N 0.000 claims 2
- NHCXSQVRIKQPQY-UHFFFAOYSA-N 2-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-6-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-1H-benzimidazole Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC(F)=C1S(C)(=O)=O)N2 NHCXSQVRIKQPQY-UHFFFAOYSA-N 0.000 claims 2
- HFCVIAOZRCFXPW-UHFFFAOYSA-N 2-(4-diethoxyphosphorylphenyl)-1,4-dimethyl-6-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]benzimidazole Chemical compound CCOP(C(C=C1)=CC=C1C1=NC(C(C)=CC(C(CC2)CCN2C2CCN(CC(C)C)CC2)=C2)=C2N1C)(OCC)=O HFCVIAOZRCFXPW-UHFFFAOYSA-N 0.000 claims 2
- WGBYQBBDOJOMBH-UHFFFAOYSA-N 4-[6-[4-[[4-(dimethylamino)piperidin-1-yl]methyl]phenyl]-1-methylbenzimidazol-2-yl]benzonitrile Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C(C=C2)=CC=C2C#N)N3C)CC1 WGBYQBBDOJOMBH-UHFFFAOYSA-N 0.000 claims 2
- IKTSJIQPLHWYBS-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-5-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C=CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N1C)=C2F IKTSJIQPLHWYBS-UHFFFAOYSA-N 0.000 claims 2
- NLYJNJDOIITTJA-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-5-[1-[8-(oxan-4-yl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=CC(C(CC1)CCN1C(CC1CC3)CC3N1C1CCOCC1)=C2F NLYJNJDOIITTJA-UHFFFAOYSA-N 0.000 claims 2
- GPNJUFROMDICSI-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-5-[1-[8-(oxetan-3-yl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=CC(C(CC1)CCN1C1CC(CC3)N(C4COC4)C3C1)=C2F GPNJUFROMDICSI-UHFFFAOYSA-N 0.000 claims 2
- CSOLTCUTLYUMKP-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-5-[1-[8-(oxetan-3-ylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=CC(C(CC1)CCN1C1CC(CC3)N(CC4COC4)C3C1)=C2F CSOLTCUTLYUMKP-UHFFFAOYSA-N 0.000 claims 2
- OGIZEOMKRNNHGD-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-(1-propan-2-ylazepan-4-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(CCC1)CCC1N(CC1)CCC1C(C=C1F)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C OGIZEOMKRNNHGD-UHFFFAOYSA-N 0.000 claims 2
- LYBHBTPWUZZILL-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1F)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C LYBHBTPWUZZILL-UHFFFAOYSA-N 0.000 claims 2
- XBXVFIWOLGPTPD-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-[1-(oxan-4-yl)azepan-4-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C(CCC1)CCN1C1CCOCC1)C=C2F XBXVFIWOLGPTPD-UHFFFAOYSA-N 0.000 claims 2
- PZIJTEDZOLLAMC-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-[1-(oxetan-3-yl)azepan-4-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C(CCC1)CCN1C1COC1)C=C2F PZIJTEDZOLLAMC-UHFFFAOYSA-N 0.000 claims 2
- GAZXFYSLHONILQ-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-[1-(oxetan-3-yl)piperidin-4-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C(CC1)CCN1C1COC1)C=C2F GAZXFYSLHONILQ-UHFFFAOYSA-N 0.000 claims 2
- STHLSFCYZGYNDW-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-[8-(oxetan-3-yl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C1CC(CC3)N(C4COC4)C3C1)C=C2F STHLSFCYZGYNDW-UHFFFAOYSA-N 0.000 claims 2
- GNDVUMOHJMBIRR-UHFFFAOYSA-N 4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[4-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC(C(F)=C2)=C1C=C2C1=CC=C(CN(CC2)CCC2N2CCCC2)C=C1 GNDVUMOHJMBIRR-UHFFFAOYSA-N 0.000 claims 2
- IHVRMZHITGBQTO-UHFFFAOYSA-N 4-fluoro-1-methyl-5-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C(C=CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N1C)=C2F IHVRMZHITGBQTO-UHFFFAOYSA-N 0.000 claims 2
- AVAAAAAILQSAOH-UHFFFAOYSA-N 4-fluoro-1-methyl-6-[1-[1-(2-methylpropyl)azepan-4-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC(C)CN(CCC1)CCC1N(CC1)CCC1C(C=C1F)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C AVAAAAAILQSAOH-UHFFFAOYSA-N 0.000 claims 2
- BOCUCLLBJPPNFI-UHFFFAOYSA-N 4-fluoro-2-(4-methylsulfonylphenyl)-5-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-1H-benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C=CC1=C2NC(C(C=C3)=CC=C3S(C)(=O)=O)=N1)=C2F BOCUCLLBJPPNFI-UHFFFAOYSA-N 0.000 claims 2
- VEQZMAXMISUAAN-UHFFFAOYSA-N 4-fluoro-5-[1-[8-(2-methoxyethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=CC(C(CC1)CCN1C1CC(CC3)N(CCOC)C3C1)=C2F VEQZMAXMISUAAN-UHFFFAOYSA-N 0.000 claims 2
- BKJMBGHFFWCMRI-UHFFFAOYSA-N 4-fluoro-6-[1-[1-(2-methoxyethyl)azepan-4-yl]piperidin-4-yl]-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C1CCN(CCOC)CCC1)C=C2F BKJMBGHFFWCMRI-UHFFFAOYSA-N 0.000 claims 2
- NAEZFQICFYNDRM-UHFFFAOYSA-N 4-fluoro-6-[1-[8-(2-methoxyethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C1CC(CC3)N(CCOC)C3C1)C=C2F NAEZFQICFYNDRM-UHFFFAOYSA-N 0.000 claims 2
- TUXCUWJCRNFRLT-UHFFFAOYSA-N 4-methyl-2-(4-methylsulfonylphenyl)-6-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-1H-benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2 TUXCUWJCRNFRLT-UHFFFAOYSA-N 0.000 claims 2
- HVGSFYYQMHUIBB-UHFFFAOYSA-N 4-methyl-6-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)-1H-benzimidazole Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C(C=C1C)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2 HVGSFYYQMHUIBB-UHFFFAOYSA-N 0.000 claims 2
- MNNIVJWDWUPSPH-UHFFFAOYSA-N 5-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-6-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC(C=C2C(CC3)CCN3C3CC(CC4)N(C5CCC5)C4C3)=C1C=C2F MNNIVJWDWUPSPH-UHFFFAOYSA-N 0.000 claims 2
- JRRWPLYDNJDMOS-UHFFFAOYSA-N 5-[1-[8-(cyclopropylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=CC(C(CC1)CCN1C1CC(CC3)N(CC4CC4)C3C1)=C2F JRRWPLYDNJDMOS-UHFFFAOYSA-N 0.000 claims 2
- IJLLHGLWSZFSTL-UHFFFAOYSA-N 5-[1-[8-(cyclopropylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-6-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC(C=C2C(CC3)CCN3C3CC(CC4)N(CC5CC5)C4C3)=C1C=C2F IJLLHGLWSZFSTL-UHFFFAOYSA-N 0.000 claims 2
- DYXWDXWCTLINQL-UHFFFAOYSA-N 5-[1-[8-(cyclopropylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-7-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C(F)=CC(C(CC1)CCN1C1CC(CC3)N(CC4CC4)C3C1)=C2 DYXWDXWCTLINQL-UHFFFAOYSA-N 0.000 claims 2
- YWZOLXUWYJSKEG-UHFFFAOYSA-N 5-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-(8-propan-2-yl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]benzimidazole Chemical compound CC(C)N(C(CC1)C2)C1CC2N(CC1)CCC1C(C(F)=C1)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C YWZOLXUWYJSKEG-UHFFFAOYSA-N 0.000 claims 2
- GHDNCYJSXRCWMU-UHFFFAOYSA-N 5-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-[8-(oxan-4-yl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C(CC1CC3)CC3N1C1CCOCC1)C(F)=C2 GHDNCYJSXRCWMU-UHFFFAOYSA-N 0.000 claims 2
- KTBKYPMPVZDIAQ-UHFFFAOYSA-N 5-fluoro-1-methyl-2-(4-methylsulfonylphenyl)-6-[1-[8-(oxetan-3-yl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C1CC(CC3)N(C4COC4)C3C1)C(F)=C2 KTBKYPMPVZDIAQ-UHFFFAOYSA-N 0.000 claims 2
- BFEWEOASHCIQJZ-UHFFFAOYSA-N 5-fluoro-1-methyl-6-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C(C(F)=C1)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C BFEWEOASHCIQJZ-UHFFFAOYSA-N 0.000 claims 2
- FESRXKIIJGIEGX-UHFFFAOYSA-N 6-[1,4-dimethyl-6-[1-[8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]benzimidazol-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)CN(C(CC1)C2)C1CC2N(CC1)CCC1C1=CC(C)=C2N=C(C3=CN4N=CN=C4C(OC)=C3)N(C)C2=C1 FESRXKIIJGIEGX-UHFFFAOYSA-N 0.000 claims 2
- PTXFSDOUASJOJX-UHFFFAOYSA-N 6-[1-(1-cyclobutylazepan-4-yl)piperidin-4-yl]-7-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C(F)=C(C(CC1)CCN1C(CCC1)CCN1C1CCC1)C=C2 PTXFSDOUASJOJX-UHFFFAOYSA-N 0.000 claims 2
- QGDCBTQKJZLFGF-UHFFFAOYSA-N 6-[1-(1-cyclopropylpiperidin-4-yl)piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C(CC2)CCN2C2CC2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C QGDCBTQKJZLFGF-UHFFFAOYSA-N 0.000 claims 2
- FQVZXMVZBVQLHN-UHFFFAOYSA-N 6-[1-(1-cyclopropylpiperidin-4-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-1-propan-2-ylbenzimidazole Chemical compound CC(C)N1C(C(C=C2)=CC(OC)=C2OC)=NC2=C1C=C(C(CC1)CCN1C(CC1)CCN1C1CC1)C=C2 FQVZXMVZBVQLHN-UHFFFAOYSA-N 0.000 claims 2
- ANXNZQMFMCOTQJ-UHFFFAOYSA-N 6-[1-(1-cyclopropylpiperidin-4-yl)piperidin-4-yl]-2-(3-fluoro-4-methylsulfonylphenyl)-1,4-dimethylbenzimidazole Chemical compound CC1=CC(C(CC2)CCN2C(CC2)CCN2C2CC2)=CC2=C1N=C(C(C=C1)=CC(F)=C1S(C)(=O)=O)N2C ANXNZQMFMCOTQJ-UHFFFAOYSA-N 0.000 claims 2
- GEVRDSPCXYJURT-UHFFFAOYSA-N 6-[1-(1-cyclopropylpiperidin-4-yl)piperidin-4-yl]-2-(4-diethoxyphosphorylphenyl)-1,4-dimethylbenzimidazole Chemical compound CCOP(C(C=C1)=CC=C1C1=NC(C(C)=CC(C(CC2)CCN2C(CC2)CCN2C2CC2)=C2)=C2N1C)(OCC)=O GEVRDSPCXYJURT-UHFFFAOYSA-N 0.000 claims 2
- BKDOYVQCGKIIDD-UHFFFAOYSA-N 6-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C(CC2)CCN2C2CC(CC3)N(C4CCC4)C3C2)=C1 BKDOYVQCGKIIDD-UHFFFAOYSA-N 0.000 claims 2
- CXHGDHQRRQWDHX-UHFFFAOYSA-N 6-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-1-cyclopropyl-4-fluoro-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CS(C(C=C1)=CC=C1C1=NC(C(F)=CC(C(CC2)CCN2C2CC(CC3)N(C4CCC4)C3C2)=C2)=C2N1C1CC1)(=O)=O CXHGDHQRRQWDHX-UHFFFAOYSA-N 0.000 claims 2
- UJADXXJJFFXJRF-UHFFFAOYSA-N 6-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-1,4-dimethylbenzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC(OC)=C3OC)N(C)C2=CC(C(CC2)CCN2C2CC(CC3)N(C4CCC4)C3C2)=C1 UJADXXJJFFXJRF-UHFFFAOYSA-N 0.000 claims 2
- LXBDEVPDONHFAX-UHFFFAOYSA-N 6-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-2-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1H-benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CC(CC3)N(C4CCC4)C3C2)=CC2=C1N=C(C(C=C1)=CC(F)=C1S(C)(=O)=O)N2 LXBDEVPDONHFAX-UHFFFAOYSA-N 0.000 claims 2
- NKFQVGRVGYCTQX-UHFFFAOYSA-N 6-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-4-methyl-2-(4-methylsulfonylphenyl)-1H-benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CC(CC3)N(C4CCC4)C3C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2 NKFQVGRVGYCTQX-UHFFFAOYSA-N 0.000 claims 2
- RNRAPBWINSIVCB-UHFFFAOYSA-N 6-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-5-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C1CC(CC3)N(C4CCC4)C3C1)C(F)=C2 RNRAPBWINSIVCB-UHFFFAOYSA-N 0.000 claims 2
- XBSJESITKUXEJS-UHFFFAOYSA-N 6-[1-(8-cyclobutyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-7-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C(F)=C(C(CC1)CCN1C1CC(CC3)N(C4CCC4)C3C1)C=C2 XBSJESITKUXEJS-UHFFFAOYSA-N 0.000 claims 2
- VFXRVEWBJVZQGK-UHFFFAOYSA-N 6-[1-(8-cyclopropyl-8-azabicyclo[3.2.1]octan-3-yl)piperidin-4-yl]-2-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1H-benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CC(CC3)N(C4CC4)C3C2)=CC2=C1N=C(C(C=C1)=CC(F)=C1S(C)(=O)=O)N2 VFXRVEWBJVZQGK-UHFFFAOYSA-N 0.000 claims 2
- RQNFBNQLGPZMOT-UHFFFAOYSA-N 6-[1-[1-(2-methoxyethyl)azepan-4-yl]piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CCN(CCOC)CCC2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C RQNFBNQLGPZMOT-UHFFFAOYSA-N 0.000 claims 2
- BMNRNAHTHQAJIM-UHFFFAOYSA-N 6-[1-[1-(cyclobutylmethyl)azepan-4-yl]piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C(CC2)CCN2C2CCN(CC3CCC3)CCC2)=C1 BMNRNAHTHQAJIM-UHFFFAOYSA-N 0.000 claims 2
- SSMMHHCFTKVIFJ-UHFFFAOYSA-N 6-[1-[1-(cyclopropylmethyl)azepan-4-yl]piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CCN(CC3CC3)CCC2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C SSMMHHCFTKVIFJ-UHFFFAOYSA-N 0.000 claims 2
- BKIJACHBCYIHDE-UHFFFAOYSA-N 6-[1-[1-(cyclopropylmethyl)azepan-4-yl]piperidin-4-yl]-4-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C=C(C(CC1)CCN1C1CCN(CC3CC3)CCC1)C=C2F BKIJACHBCYIHDE-UHFFFAOYSA-N 0.000 claims 2
- CLQVXRBUTCCJSG-UHFFFAOYSA-N 6-[1-[1-(cyclopropylmethyl)piperidin-4-yl]piperidin-4-yl]-7-fluoro-1-methyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CN1C(C(C=C2)=CC=C2S(C)(=O)=O)=NC2=C1C(F)=C(C(CC1)CCN1C1CCN(CC3CC3)CC1)C=C2 CLQVXRBUTCCJSG-UHFFFAOYSA-N 0.000 claims 2
- CREMIHAWFFJMTC-UHFFFAOYSA-N 6-[1-[8-(2-methoxyethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CC(CC3)N(CCOC)C3C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C CREMIHAWFFJMTC-UHFFFAOYSA-N 0.000 claims 2
- CSSRFRFVTNVYAE-UHFFFAOYSA-N 6-[1-[8-(cyclobutylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-1,4-dimethylbenzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC(OC)=C3OC)N(C)C2=CC(C(CC2)CCN2C2CC(CC3)N(CC4CCC4)C3C2)=C1 CSSRFRFVTNVYAE-UHFFFAOYSA-N 0.000 claims 2
- XNKLHPQUVGORRF-UHFFFAOYSA-N 6-[1-[8-(cyclopropylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C(CC2)CCN2C2CC(CC3)N(CC4CC4)C3C2)=C1 XNKLHPQUVGORRF-UHFFFAOYSA-N 0.000 claims 2
- CVNIMJJMZPYOEE-UHFFFAOYSA-N 6-[1-[8-(cyclopropylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(3,4-dimethoxyphenyl)-1,4-dimethylbenzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC(OC)=C3OC)N(C)C2=CC(C(CC2)CCN2C2CC(CC3)N(CC4CC4)C3C2)=C1 CVNIMJJMZPYOEE-UHFFFAOYSA-N 0.000 claims 2
- GBTKOIINTNPKGH-UHFFFAOYSA-N 6-[1-[8-(cyclopropylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1H-benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CC(CC3)N(CC4CC4)C3C2)=CC2=C1N=C(C(C=C1)=CC(F)=C1S(C)(=O)=O)N2 GBTKOIINTNPKGH-UHFFFAOYSA-N 0.000 claims 2
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- JAKYVMAHGANUER-UHFFFAOYSA-N 6-[1-[8-(cyclopropylmethyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-4-methyl-2-(4-methylsulfonylphenyl)-1H-benzimidazole Chemical compound CC1=CC(C(CC2)CCN2C2CC(CC3)N(CC4CC4)C3C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2 JAKYVMAHGANUER-UHFFFAOYSA-N 0.000 claims 2
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- VUYFPYMSKAWWNI-UHFFFAOYSA-N CS(C(C=C1)=CC=C1C1=NC(C(F)=CC(C2=CC=C(CN(CC3)CCC3N3CCCC3)C=C2)=C2)=C2N1C1CC1)(=O)=O Chemical compound CS(C(C=C1)=CC=C1C1=NC(C(F)=CC(C2=CC=C(CN(CC3)CCC3N3CCCC3)C=C2)=C2)=C2N1C1CC1)(=O)=O VUYFPYMSKAWWNI-UHFFFAOYSA-N 0.000 claims 2
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- SXBAUMZEFUQCOR-UHFFFAOYSA-N N,N-dimethyl-1-[[4-[3-methyl-2-(3-methylsulfonylphenyl)benzimidazol-5-yl]phenyl]methyl]piperidin-4-amine Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C2=CC(S(C)(=O)=O)=CC=C2)N3C)CC1 SXBAUMZEFUQCOR-UHFFFAOYSA-N 0.000 claims 2
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- YQDJLJWGQWYESU-UHFFFAOYSA-N N-[4-[6-[4-[[4-(dimethylamino)piperidin-1-yl]methyl]phenyl]-1-methylbenzimidazol-2-yl]phenyl]methanesulfonamide Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C(C=C2)=CC=C2NS(C)(=O)=O)N3C)CC1 YQDJLJWGQWYESU-UHFFFAOYSA-N 0.000 claims 2
- ANGSPOSEQHYNTI-UHFFFAOYSA-N N-cyclopropyl-1-[[4-[3,7-dimethyl-2-(4-methylsulfonylphenyl)benzimidazol-5-yl]-2-fluorophenyl]methyl]-N-methylpiperidin-4-amine Chemical compound CC1=CC(C2=CC(F)=C(CN(CC3)CCC3N(C)C3CC3)C=C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C ANGSPOSEQHYNTI-UHFFFAOYSA-N 0.000 claims 2
- JKBZAGJUTPHOGL-UHFFFAOYSA-N N-cyclopropyl-1-[[4-[3,7-dimethyl-2-(4-methylsulfonylphenyl)benzimidazol-5-yl]phenyl]methyl]-N-methylpiperidin-4-amine Chemical compound CC1=CC(C2=CC=C(CN(CC3)CCC3N(C)C3CC3)C=C2)=CC2=C1N=C(C(C=C1)=CC=C1S(C)(=O)=O)N2C JKBZAGJUTPHOGL-UHFFFAOYSA-N 0.000 claims 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- BZUPOBMECWCTPV-UHFFFAOYSA-N 6-[3-[[4-(azetidin-1-yl)piperidin-1-yl]methyl]-5-fluorophenyl]-1,4-dimethyl-2-(4-methylsulfonylphenyl)benzimidazole Chemical compound CC1=C2N=C(C(C=C3)=CC=C3S(C)(=O)=O)N(C)C2=CC(C2=CC(CN(CC3)CCC3N3CCC3)=CC(F)=C2)=C1 BZUPOBMECWCTPV-UHFFFAOYSA-N 0.000 claims 1
- 206010004664 Biliary fibrosis Diseases 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- JEABQQHPPZKDQR-UHFFFAOYSA-N N-[3-[6-[4-[[4-(dimethylamino)piperidin-1-yl]methyl]phenyl]-1-methylbenzimidazol-2-yl]phenyl]methanesulfonamide Chemical compound CN(C)C1CCN(CC(C=C2)=CC=C2C(C=C2)=CC3=C2N=C(C2=CC=CC(NS(C)(=O)=O)=C2)N3C)CC1 JEABQQHPPZKDQR-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 125000005959 diazepanyl group Chemical group 0.000 claims 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
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| MX2024009441A (es) * | 2022-02-18 | 2024-08-14 | Bristol Myers Squibb Co | Compuestos de imidazopiridinilo sustituidos utiles como inhibidores del receptor tipo toll 9 (tlr9). |
| US20250163054A1 (en) * | 2022-02-18 | 2025-05-22 | Bristol-Myers Squibb Company | Substituted bicyclic heteroaryl compounds useful as inhibitors of tlr9 |
| CN117466863B (zh) * | 2022-07-20 | 2026-03-24 | 盛睿泽华医药科技（苏州）有限公司 | 含芳香族取代基的苯并咪唑化合物及其制备方法和用途 |
| WO2024102886A1 (en) * | 2022-11-10 | 2024-05-16 | Bristol-Myers Squibb Company | Substituted benzimidazole compounds useful as inhibitors of tlr9 |
| KR20250094727A (ko) * | 2022-11-10 | 2025-06-25 | 브리스톨-마이어스 스큅 컴퍼니 | Tlr9의 억제제로서 유용한 치환된 퀴놀론 화합물 |
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| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| CN105992766A (zh) | 2013-12-13 | 2016-10-05 | 武田药品工业株式会社 | 作为tlr抑制剂的吡咯并[3,2-c]吡啶衍生物 |
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| JP7028861B2 (ja) | 2016-09-09 | 2022-03-02 | ブリストル－マイヤーズ スクイブ カンパニー | ピリジル置換のインドール化合物 |
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| EA202091484A1 (ru) | 2017-12-18 | 2021-03-25 | Бристол-Маерс Сквибб Компани | 4-азаиндольные соединения |
| MX2020005462A (es) | 2017-12-19 | 2020-09-07 | Bristol Myers Squibb Co | Compuestos de indol sustituidos utiles como inhibidores de receptores tipo toll (tlr). |
| WO2019126081A1 (en) | 2017-12-19 | 2019-06-27 | Bristol-Myers Squibb Company | Amide substituted indole compounds useful as tlr inhibitors |
| JP7304352B2 (ja) | 2017-12-19 | 2023-07-06 | ブリストル－マイヤーズ スクイブ カンパニー | ６－アザインドール化合物 |
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| EP3728218B1 (en) | 2017-12-20 | 2021-12-01 | Bristol-Myers Squibb Company | Amino indole compounds useful as tlr inhibitors |
| SG11202005733QA (en) | 2017-12-20 | 2020-07-29 | Bristol Myers Squibb Co | Diazaindole compounds |
| WO2019136147A1 (en) * | 2018-01-03 | 2019-07-11 | The Board Of Trustees Of The University Of Illinois | Toll-like receptor signaling inhibitors |
| AU2019319835A1 (en) | 2018-08-08 | 2021-03-25 | Bristol-Myers Squibb Company | Indole and azaindole inhibitors of PAD enzymes |
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