CA2645731A1 - N-substituted-azacyclylamines as histamine-3 antagonists - Google Patents

Info

Publication number

CA2645731A1

CA2645731A1 CA002645731A CA2645731A CA2645731A1 CA 2645731 A1 CA2645731 A1 CA 2645731A1 CA 002645731 A CA002645731 A CA 002645731A CA 2645731 A CA2645731 A CA 2645731A CA 2645731 A1 CA2645731 A1 CA 2645731A1

Authority

CA

Canada

Prior art keywords

methyl

benzimidazol

benzoyl

bipyrrolidine

pyrrolidin

Prior art date

2006-03-15

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000005557 antagonist Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 145
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 208000015114 central nervous system disease Diseases 0.000 claims abstract description 8
• 208000012902 Nervous system disease Diseases 0.000 claims abstract 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 137
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 72
• -1 cycloheteroalkyl Chemical group 0.000 claims description 70
• 238000000034 method Methods 0.000 claims description 57
• 238000002360 preparation method Methods 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 25
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 239000002904 solvent Substances 0.000 claims description 15
• 102000004384 Histamine H3 receptors Human genes 0.000 claims description 14
• 108090000981 Histamine H3 receptors Proteins 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 11
• 208000024827 Alzheimer disease Diseases 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 11
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 11
• 208000010877 cognitive disease Diseases 0.000 claims description 10
• 102000005962 receptors Human genes 0.000 claims description 10
• 108020003175 receptors Proteins 0.000 claims description 10
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 9
• 125000002619 bicyclic group Chemical group 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 150000002475 indoles Chemical class 0.000 claims description 5
• 208000019116 sleep disease Diseases 0.000 claims description 5
• ZZCKGXAYSCVENO-UHFFFAOYSA-N 1-[[4-[(4-fluorobenzimidazol-1-yl)methyl]phenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1)=CC=C1CN1C2=CC=CC(F)=C2N=C1 ZZCKGXAYSCVENO-UHFFFAOYSA-N 0.000 claims description 4
• JZSKJBGVSGURIV-FQEVSTJZSA-N [4-[(5-fluorobenzimidazol-1-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC=C(C=C3N=C2)F)CCCC1 JZSKJBGVSGURIV-FQEVSTJZSA-N 0.000 claims description 4
• HKSPIQPSCHDGLG-NRFANRHFSA-N [4-[(6-chloro-2-methylbenzimidazol-1-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC(Cl)=CC=C3N=C2C)CCCC1 HKSPIQPSCHDGLG-NRFANRHFSA-N 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• GOYVYKRMDXBFOQ-UHFFFAOYSA-N [4-[(1-ethylbenzimidazol-2-yl)methyl]phenyl]-(3-pyrrolidin-1-ylpyrrolidin-1-yl)methanone Chemical compound N=1C2=CC=CC=C2N(CC)C=1CC(C=C1)=CC=C1C(=O)N(C1)CCC1N1CCCC1 GOYVYKRMDXBFOQ-UHFFFAOYSA-N 0.000 claims description 3
• TYPMSXWMJDHEPY-QFIPXVFZSA-N [4-[(1-methylindol-3-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CC2=CN(C3=CC=CC=C32)C)CCCC1 TYPMSXWMJDHEPY-QFIPXVFZSA-N 0.000 claims description 3
• FWMXBCISCWVQLF-NRFANRHFSA-N [4-[(5-chloro-2-methylbenzimidazol-1-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC=C(Cl)C=C3N=C2C)CCCC1 FWMXBCISCWVQLF-NRFANRHFSA-N 0.000 claims description 3
• 150000001556 benzimidazoles Chemical group 0.000 claims description 3
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• NKJNVVMJEBRTDJ-NRFANRHFSA-N (4-benzylphenyl)-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C=2C=CC(CC=3C=CC=CC=3)=CC=2)CCCC1 NKJNVVMJEBRTDJ-NRFANRHFSA-N 0.000 claims description 2
• XNEFBIXQNVFRLQ-WIIYFNMSSA-N 1-[1-[4-[(3s)-3-pyrrolidin-1-ylpyrrolidine-1-carbonyl]phenyl]ethyl]indole-5-carbonitrile Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)C(C)N2C3=CC=C(C=C3C=C2)C#N)CCCC1 XNEFBIXQNVFRLQ-WIIYFNMSSA-N 0.000 claims description 2
• WNYFCVHBWNPGFS-UHFFFAOYSA-N 1-[[2-chloro-4-[(3-piperidin-1-ylpyrrolidin-1-yl)methyl]phenyl]methyl]benzimidazole Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C(Cl)=CC=1CN(C1)CCC1N1CCCCC1 WNYFCVHBWNPGFS-UHFFFAOYSA-N 0.000 claims description 2
• FSCHBUFEORTTSK-UHFFFAOYSA-N 1-[[4-(benzimidazol-1-ylmethyl)-3-chlorophenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1Cl)=CC=C1CN1C2=CC=CC=C2N=C1 FSCHBUFEORTTSK-UHFFFAOYSA-N 0.000 claims description 2
• FKYWWSRNAPEWLB-UHFFFAOYSA-N 1-[[4-(indol-1-ylmethyl)phenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1)=CC=C1CN1C2=CC=CC=C2C=C1 FKYWWSRNAPEWLB-UHFFFAOYSA-N 0.000 claims description 2
• PCTJZBPKMUXKBV-UHFFFAOYSA-N 4-(benzimidazol-1-ylmethyl)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C=CC=1C(=O)NCCN1CCCC1 PCTJZBPKMUXKBV-UHFFFAOYSA-N 0.000 claims description 2
• BNKWKNSYRGYGQT-UHFFFAOYSA-N 4-[(2-methylbenzimidazol-1-yl)methyl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=NC2=CC=CC=C2N1CC(C=C1)=CC=C1C(=O)NCCN1CCCC1 BNKWKNSYRGYGQT-UHFFFAOYSA-N 0.000 claims description 2
• OSZHOKFIDJUEGU-UHFFFAOYSA-N 4-fluoro-1-[[4-[(3-piperidin-1-ylpyrrolidin-1-yl)methyl]phenyl]methyl]benzimidazole Chemical compound C1=NC=2C(F)=CC=CC=2N1CC(C=C1)=CC=C1CN(C1)CCC1N1CCCCC1 OSZHOKFIDJUEGU-UHFFFAOYSA-N 0.000 claims description 2
• ITAJFFQEBAKMJR-ZZWBGTBQSA-N 5-fluoro-1-[[4-[[3-[(2r)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methyl]phenyl]methyl]benzimidazole Chemical compound C[C@@H]1CCCN1C1CN(CC=2C=CC(CN3C4=CC=C(F)C=C4N=C3)=CC=2)CC1 ITAJFFQEBAKMJR-ZZWBGTBQSA-N 0.000 claims description 2
• 208000012239 Developmental disease Diseases 0.000 claims description 2
• YFOVYMUNACKLJM-SFHVURJKSA-N [(3s)-3-(azetidin-1-yl)pyrrolidin-1-yl]-[4-[(7-fluorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C=NC=3C=CC=C(C2=3)F)CCC1 YFOVYMUNACKLJM-SFHVURJKSA-N 0.000 claims description 2
• CUHVFDRJOCNUTK-UGSOOPFHSA-N [(3s)-3-aminopyrrolidin-1-yl]-[4-[(1s)-1-(5-chloro-2-methylbenzimidazol-1-yl)ethyl]phenyl]methanone Chemical compound C1=CC([C@H](C)N2C3=CC=C(Cl)C=C3N=C2C)=CC=C1C(=O)N1CC[C@H](N)C1 CUHVFDRJOCNUTK-UGSOOPFHSA-N 0.000 claims description 2
• OYJUQBUJIKMYLC-INIZCTEOSA-N [(3s)-3-aminopyrrolidin-1-yl]-[4-[(5-chlorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1[C@@H](N)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=C(Cl)C=C2N=C1 OYJUQBUJIKMYLC-INIZCTEOSA-N 0.000 claims description 2
• MXFTYPZMFCWDGD-IBGZPJMESA-N [(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]-[4-[[2-(trifluoromethyl)benzimidazol-1-yl]methyl]phenyl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC=CC=C3N=C2C(F)(F)F)CCCC1 MXFTYPZMFCWDGD-IBGZPJMESA-N 0.000 claims description 2
• CHXYRVONIWLABP-UHFFFAOYSA-N [4-(1h-benzimidazol-2-ylmethyl)phenyl]-(3-piperidin-1-ylpyrrolidin-1-yl)methanone Chemical compound C=1C=C(CC=2NC3=CC=CC=C3N=2)C=CC=1C(=O)N(C1)CCC1N1CCCCC1 CHXYRVONIWLABP-UHFFFAOYSA-N 0.000 claims description 2
• HCASEGGSGZPNRG-UHFFFAOYSA-N [4-(1h-benzimidazol-2-ylmethyl)phenyl]-(3-pyrrolidin-1-ylpyrrolidin-1-yl)methanone Chemical compound C=1C=C(CC=2NC3=CC=CC=C3N=2)C=CC=1C(=O)N(C1)CCC1N1CCCC1 HCASEGGSGZPNRG-UHFFFAOYSA-N 0.000 claims description 2
• MKFUTLJBZBYCCA-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)-2-fluorophenyl]-(3-pyrrolidin-1-ylpyrrolidin-1-yl)methanone Chemical compound FC1=CC(CN2C3=CC=CC=C3N=C2)=CC=C1C(=O)N(C1)CCC1N1CCCC1 MKFUTLJBZBYCCA-UHFFFAOYSA-N 0.000 claims description 2
• FLFNHBOROKVAFC-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-(3-piperidin-1-ylpiperidin-1-yl)methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C=CC=1C(=O)N(C1)CCCC1N1CCCCC1 FLFNHBOROKVAFC-UHFFFAOYSA-N 0.000 claims description 2
• WSVDCIDSNHAANT-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-(3-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C=CC=1C(=O)N(C1)CCCC1N1CCCC1 WSVDCIDSNHAANT-UHFFFAOYSA-N 0.000 claims description 2
• WMGFFKHQNCLGHB-WIYYLYMNSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-[(3r)-3-[(2r)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methanone Chemical compound C[C@@H]1CCCN1[C@H]1CN(C(=O)C=2C=CC(CN3C4=CC=CC=C4N=C3)=CC=2)CC1 WMGFFKHQNCLGHB-WIYYLYMNSA-N 0.000 claims description 2
• WMGFFKHQNCLGHB-GHTZIAJQSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-[(3r)-3-[(2s)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methanone Chemical compound C[C@H]1CCCN1[C@H]1CN(C(=O)C=2C=CC(CN3C4=CC=CC=C4N=C3)=CC=2)CC1 WMGFFKHQNCLGHB-GHTZIAJQSA-N 0.000 claims description 2
• RBFNAMZWICIZDO-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-[3-(2-methylpyrrolidin-1-yl)piperidin-1-yl]methanone Chemical compound CC1CCCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=CC=C4N=C3)=CC=2)CCC1 RBFNAMZWICIZDO-UHFFFAOYSA-N 0.000 claims description 2
• CCUDNLWFJUWTMY-AIBWNMTMSA-N [4-(indazol-1-ylmethyl)phenyl]-[1-[(3s)-pyrrolidin-3-yl]pyrrolidin-2-yl]methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3C=N2)C=CC=1C(=O)C1CCCN1[C@H]1CCNC1 CCUDNLWFJUWTMY-AIBWNMTMSA-N 0.000 claims description 2
• DZNOGNRCWAFGJA-BBQAJUCSSA-N [4-(indol-1-ylmethyl)phenyl]-[1-[(3s)-pyrrolidin-3-yl]pyrrolidin-2-yl]methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3C=C2)C=CC=1C(=O)C1CCCN1[C@H]1CCNC1 DZNOGNRCWAFGJA-BBQAJUCSSA-N 0.000 claims description 2
• GOYVYKRMDXBFOQ-NRFANRHFSA-N [4-[(1-ethylbenzimidazol-2-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CC=2N(C3=CC=CC=C3N=2)CC)CCCC1 GOYVYKRMDXBFOQ-NRFANRHFSA-N 0.000 claims description 2
• CJHOAMPISBRSIJ-VWLOTQADSA-N [4-[(1-phenylbenzimidazol-2-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C=2C=CC(CC=3N(C4=CC=CC=C4N=3)C=3C=CC=CC=3)=CC=2)CCCC1 CJHOAMPISBRSIJ-VWLOTQADSA-N 0.000 claims description 2
• IMEIHJWXQIJUEO-QFIPXVFZSA-N [4-[(1-propylbenzimidazol-2-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CC=2N(C3=CC=CC=C3N=2)CCC)CCCC1 IMEIHJWXQIJUEO-QFIPXVFZSA-N 0.000 claims description 2
• QISUIGKPHXAXFI-JTSKRJEESA-N [4-[(1s)-1-(5-chloro-2-methylbenzimidazol-1-yl)ethyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)[C@H](C)N2C3=CC=C(Cl)C=C3N=C2C)CCCC1 QISUIGKPHXAXFI-JTSKRJEESA-N 0.000 claims description 2
• WEFBGFKYFBJFPI-JTSKRJEESA-N [4-[(1s)-1-(6-chloro-2-methylbenzimidazol-1-yl)ethyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)[C@H](C)N2C3=CC(Cl)=CC=C3N=C2C)CCCC1 WEFBGFKYFBJFPI-JTSKRJEESA-N 0.000 claims description 2
• QZPNKFJJDYDSGB-RXVVDRJESA-N [4-[(1s)-1-(benzimidazol-1-yl)ethyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)[C@H](C)N2C3=CC=CC=C3N=C2)CCCC1 QZPNKFJJDYDSGB-RXVVDRJESA-N 0.000 claims description 2
• ADZIWICILUZNFO-UHFFFAOYSA-N [4-[(2-phenylbenzimidazol-1-yl)methyl]phenyl]-(3-pyrrolidin-1-ylpyrrolidin-1-yl)methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2C=2C=CC=CC=2)C=CC=1C(=O)N(C1)CCC1N1CCCC1 ADZIWICILUZNFO-UHFFFAOYSA-N 0.000 claims description 2
• FWMXBCISCWVQLF-UHFFFAOYSA-N [4-[(5-chloro-2-methylbenzimidazol-1-yl)methyl]phenyl]-(3-pyrrolidin-1-ylpyrrolidin-1-yl)methanone Chemical compound CC1=NC2=CC(Cl)=CC=C2N1CC(C=C1)=CC=C1C(=O)N(C1)CCC1N1CCCC1 FWMXBCISCWVQLF-UHFFFAOYSA-N 0.000 claims description 2
• NXJVFLMPXBWWFL-FQEVSTJZSA-N [4-[(5-chlorobenzimidazol-1-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC=C(C=C3N=C2)Cl)CCCC1 NXJVFLMPXBWWFL-FQEVSTJZSA-N 0.000 claims description 2
• XYZKJWCNULDFKE-OQHSHRKDSA-N [4-[(5-fluorobenzimidazol-1-yl)methyl]phenyl]-[3-[(2r)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methanone Chemical compound C[C@@H]1CCCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=C(F)C=C4N=C3)=CC=2)CC1 XYZKJWCNULDFKE-OQHSHRKDSA-N 0.000 claims description 2
• XYZKJWCNULDFKE-PBVYKCSPSA-N [4-[(5-fluorobenzimidazol-1-yl)methyl]phenyl]-[3-[(2s)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methanone Chemical compound C[C@H]1CCCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=C(F)C=C4N=C3)=CC=2)CC1 XYZKJWCNULDFKE-PBVYKCSPSA-N 0.000 claims description 2
• QMGPOQDFYWLZBM-UHFFFAOYSA-N [4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]-(3-piperidin-1-ylpyrrolidin-1-yl)methanone Chemical compound C1=NC2=CC(C)=CC=C2N1CC(C=C1)=CC=C1C(=O)N(C1)CCC1N1CCCCC1 QMGPOQDFYWLZBM-UHFFFAOYSA-N 0.000 claims description 2
• IVQSAQWOHVCNMN-UHFFFAOYSA-N [4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]-[3-(2-methylpiperidin-1-yl)pyrrolidin-1-yl]methanone Chemical compound CC1CCCCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=C(C)C=C4N=C3)=CC=2)CC1 IVQSAQWOHVCNMN-UHFFFAOYSA-N 0.000 claims description 2
• LXRIHKRSUHOUJI-UHFFFAOYSA-N [4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]-[3-(4-methyl-1,4-diazepan-1-yl)pyrrolidin-1-yl]methanone Chemical compound C1CN(C)CCCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=C(C)C=C4N=C3)=CC=2)CC1 LXRIHKRSUHOUJI-UHFFFAOYSA-N 0.000 claims description 2
• QHAIYCPEDMXVCO-UHFFFAOYSA-N [4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]-[3-(4-methylpiperazin-1-yl)pyrrolidin-1-yl]methanone Chemical compound C1CN(C)CCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=C(C)C=C4N=C3)=CC=2)CC1 QHAIYCPEDMXVCO-UHFFFAOYSA-N 0.000 claims description 2
• IENOVDDWBKZXOA-UHFFFAOYSA-N [4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]-[3-(4-methylpiperidin-1-yl)pyrrolidin-1-yl]methanone Chemical compound C1CC(C)CCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=C(C)C=C4N=C3)=CC=2)CC1 IENOVDDWBKZXOA-UHFFFAOYSA-N 0.000 claims description 2
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