JPWO2019157458A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2019157458A5 JPWO2019157458A5 JP2020542437A JP2020542437A JPWO2019157458A5 JP WO2019157458 A5 JPWO2019157458 A5 JP WO2019157458A5 JP 2020542437 A JP2020542437 A JP 2020542437A JP 2020542437 A JP2020542437 A JP 2020542437A JP WO2019157458 A5 JPWO2019157458 A5 JP WO2019157458A5
- Authority
- JP
- Japan
- Prior art keywords
- benzodiazole
- fluoro
- pyridin
- pyridine
- substituted
- 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.)
- Granted
Links
- -1 4-Fluoro-1H-1,3-benzodiazole-2-yl Chemical group 0.000 claims 70
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 25
- 239000000203 mixture Substances 0.000 claims 24
- 239000012453 solvate Substances 0.000 claims 24
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 13
- 125000004404 heteroalkyl group Chemical group 0.000 claims 13
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 3
- YTEIHWVCQJZNEN-UHFFFAOYSA-N 3-pyridin-4-ylpyridine Chemical compound C1=CN=CC(C=2C=CN=CC=2)=C1 YTEIHWVCQJZNEN-UHFFFAOYSA-N 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- PEKSFTWITUWNKO-UHFFFAOYSA-N 1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound FC1=CC(=CC=2NC(=NC=21)C=1C=NC=C(C=1N1CC(CC1)N)C1=CC(=CC(=C1)C)F)F PEKSFTWITUWNKO-UHFFFAOYSA-N 0.000 claims 2
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 2
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 2
- UNHOPMIDKWXFMF-UHFFFAOYSA-N 1-methylpyrrolidin-3-amine Chemical compound CN1CCC(N)C1 UNHOPMIDKWXFMF-UHFFFAOYSA-N 0.000 claims 2
- DRXGJAANBSRBNW-INIZCTEOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=CC(F)=CC(=C1)C#N DRXGJAANBSRBNW-INIZCTEOSA-N 0.000 claims 2
- JFSILHPXTSLHJE-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-chloro-1-methylbenzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2Cl)C=1C=C(C#N)C=CC=1 JFSILHPXTSLHJE-KRWDZBQOSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- KNURDJSPJNPJSP-OAHLLOKOSA-N (3R)-1-[3-(3-chloro-5-fluorophenyl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound N[C@@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(Cl)=CC(F)=C1 KNURDJSPJNPJSP-OAHLLOKOSA-N 0.000 claims 1
- LZWOSTYOXLEYKD-GOSISDBHSA-N (3R)-1-[3-(4-methyl-1H-benzimidazol-2-yl)-5-(3-methylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=CC=CC(=C1)C1=CN=CC(C2=NC3=C(C)C=CC=C3N2)=C1N1CC[C@@H](N)C1 LZWOSTYOXLEYKD-GOSISDBHSA-N 0.000 claims 1
- PUAZJCMVJYTMTC-KRWDZBQOSA-N (3S)-1-[3-(3,5-difluorophenyl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(F)=CC(F)=C2)=C1N1CC[C@H](N)C1 PUAZJCMVJYTMTC-KRWDZBQOSA-N 0.000 claims 1
- KNURDJSPJNPJSP-HNNXBMFYSA-N (3S)-1-[3-(3-chloro-5-fluorophenyl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(Cl)=CC(F)=C1 KNURDJSPJNPJSP-HNNXBMFYSA-N 0.000 claims 1
- ZUVRJTOALGTZKB-KRWDZBQOSA-N (3S)-1-[3-(3-chloro-5-fluorophenyl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound ClC=1C=C(C=C(C=1)F)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=NC2=C(N1)C=CC=C2C ZUVRJTOALGTZKB-KRWDZBQOSA-N 0.000 claims 1
- JRCVPWCSSLUKSY-INIZCTEOSA-N (3S)-1-[3-(3-chloro-5-fluorophenyl)-5-(6-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound ClC=1C=C(C=C(C=1)F)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=NC2=C(N1)C=C(C=C2)F JRCVPWCSSLUKSY-INIZCTEOSA-N 0.000 claims 1
- ZQUKDBGSHPJGMN-INIZCTEOSA-N (3S)-1-[3-(3-chloro-5-fluorophenyl)-5-(6-methoxy-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound COC1=CC=C2NC(=NC2=C1)C1=CN=CC(C2=CC(Cl)=CC(F)=C2)=C1N1CC[C@H](N)C1 ZQUKDBGSHPJGMN-INIZCTEOSA-N 0.000 claims 1
- SLUJGFNBZQEPDA-KRWDZBQOSA-N (3S)-1-[3-(3-chloro-5-fluorophenyl)-5-(6-methyl-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=CC=C2NC(=NC2=C1)C1=CN=CC(C2=CC(Cl)=CC(F)=C2)=C1N1CC[C@H](N)C1 SLUJGFNBZQEPDA-KRWDZBQOSA-N 0.000 claims 1
- JNHQPBVZDHZQGW-KRWDZBQOSA-N (3S)-1-[3-(3-fluoro-5-methoxyphenyl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound COC1=CC(=CC(F)=C1)C1=C(N2CC[C@H](N)C2)C(=CN=C1)C1=NC2=C(C)C=CC=C2N1 JNHQPBVZDHZQGW-KRWDZBQOSA-N 0.000 claims 1
- XKSDARXKZBZUHZ-SFHVURJKSA-N (3S)-1-[3-(3-fluoro-5-methylphenyl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=CC(=CC(F)=C1)C1=C(N2CC[C@H](N)C2)C(=CN=C1)C1=NC2=C(C)C=CC=C2N1 XKSDARXKZBZUHZ-SFHVURJKSA-N 0.000 claims 1
- MJDNNMGBJURKJT-INIZCTEOSA-N (3S)-1-[3-(4-chloro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=CC(=CC(F)=C1)C1=CN=CC(C2=NC3=CC=CC(Cl)=C3N2)=C1N1CC[C@H](N)C1 MJDNNMGBJURKJT-INIZCTEOSA-N 0.000 claims 1
- XUSOHRPGWULAEH-HNNXBMFYSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(2-methylpyridin-4-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound FC1=CC=CC=2NC(=NC=21)C=1C(=C(C=NC=1)C1=CC(=NC=C1)C)N1C[C@H](CC1)N XUSOHRPGWULAEH-HNNXBMFYSA-N 0.000 claims 1
- VFLKUTDOBPKJLJ-INIZCTEOSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound FC1=CC=CC=2NC(=NC=21)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=CC(=CC(=C1)C)F VFLKUTDOBPKJLJ-INIZCTEOSA-N 0.000 claims 1
- ZEHFTCWXZPWUIN-HNNXBMFYSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylsulfonylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound FC1=CC=CC=2NC(=NC=21)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=CC(=CC(=C1)S(=O)(=O)C)F ZEHFTCWXZPWUIN-HNNXBMFYSA-N 0.000 claims 1
- SWHOESOEJKVUDO-HNNXBMFYSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(3-methylsulfonylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound FC1=CC=CC=2NC(=NC=21)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=CC(=CC=C1)S(=O)(=O)C SWHOESOEJKVUDO-HNNXBMFYSA-N 0.000 claims 1
- ZLDATHRCEOKAIY-KRWDZBQOSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-[3-(methoxyiminomethyl)phenyl]pyridin-4-yl]pyrrolidin-3-amine Chemical compound FC1=CC=CC=2NC(=NC=21)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=CC(=CC=C1)C=NOC ZLDATHRCEOKAIY-KRWDZBQOSA-N 0.000 claims 1
- LZWOSTYOXLEYKD-SFHVURJKSA-N (3S)-1-[3-(4-methyl-1H-benzimidazol-2-yl)-5-(3-methylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=CC=CC=2NC(=NC=21)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=CC(=CC=C1)C LZWOSTYOXLEYKD-SFHVURJKSA-N 0.000 claims 1
- LFESRXFIZMUZNU-INIZCTEOSA-N (3S)-1-[3-(6-chloro-1H-benzimidazol-2-yl)-5-(3-chloro-5-fluorophenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=CC(Cl)=CC(F)=C1)C1=NC2=CC(Cl)=CC=C2N1 LFESRXFIZMUZNU-INIZCTEOSA-N 0.000 claims 1
- UAXCRLQRTRNVQL-KRWDZBQOSA-N (3S)-1-[3-(6-chloro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=CC(=CC(F)=C1)C1=CN=CC(C2=NC3=CC=C(Cl)C=C3N2)=C1N1CC[C@H](N)C1 UAXCRLQRTRNVQL-KRWDZBQOSA-N 0.000 claims 1
- WDBOXDDMDHXRFF-KRWDZBQOSA-N (3S)-1-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(F)=CC(=C2)C(F)(F)F)=C1N1CC[C@H](N)C1 WDBOXDDMDHXRFF-KRWDZBQOSA-N 0.000 claims 1
- RISSYSYAUCJLMG-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-[3-(trifluoromethyl)phenyl]pyridin-4-yl]-3-methylazetidin-3-yl]ethanamine Chemical compound FC1=CC(=CC=2NC(=NC=21)C=1C=NC=C(C=1N1CC(C1)(C)C(C)N)C1=CC(=CC=C1)C(F)(F)F)F RISSYSYAUCJLMG-UHFFFAOYSA-N 0.000 claims 1
- SMDSSAAHKXSWLW-UHFFFAOYSA-N 1-[3-(2,3-dihydro-1-benzofuran-6-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC2=C(CCO2)C=C1 SMDSSAAHKXSWLW-UHFFFAOYSA-N 0.000 claims 1
- IKDGFWZWVXJQIX-UHFFFAOYSA-N 1-[3-(3-chloro-5-fluorophenyl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound ClC=1C=C(C=C(C=1)F)C=1C=NC=C(C=1N1CC(CC1)(N)C)C1=NC2=C(N1)C=CC=C2F IKDGFWZWVXJQIX-UHFFFAOYSA-N 0.000 claims 1
- LPOIKBZCTPVNQC-UHFFFAOYSA-N 1-[3-(3-chlorophenyl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(Cl)=CC=C1 LPOIKBZCTPVNQC-UHFFFAOYSA-N 0.000 claims 1
- YIPXKPPELHRHIR-UHFFFAOYSA-N 1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(3-imidazol-1-ylphenyl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=CC(=CC=C1)N1C=CN=C1)C1=NC2=C(F)C=CC=C2N1 YIPXKPPELHRHIR-UHFFFAOYSA-N 0.000 claims 1
- KNWVKJHJEHPHQW-UHFFFAOYSA-N 1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(3-methoxyphenyl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound COC1=CC=CC(=C1)C1=CN=CC(C2=NC3=C(F)C=CC=C3N2)=C1N1CCC(C)(N)C1 KNWVKJHJEHPHQW-UHFFFAOYSA-N 0.000 claims 1
- KNICYBVOEFJHRF-UHFFFAOYSA-N 1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(3-methylsulfonylphenyl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=CC(=CC=C1)S(C)(=O)=O)C1=NC2=C(F)C=CC=C2N1 KNICYBVOEFJHRF-UHFFFAOYSA-N 0.000 claims 1
- YRBJCSJVKIMDKF-UHFFFAOYSA-N 1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(3-pyrazol-1-ylphenyl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=CC(=CC=C1)N1C=CC=N1)C1=NC2=C(F)C=CC=C2N1 YRBJCSJVKIMDKF-UHFFFAOYSA-N 0.000 claims 1
- RQAOJAOTAMDOEB-UHFFFAOYSA-N 1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-[3-(trifluoromethoxy)phenyl]pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=CC(OC(F)(F)F)=CC=C1)C1=NC2=C(F)C=CC=C2N1 RQAOJAOTAMDOEB-UHFFFAOYSA-N 0.000 claims 1
- YLKAGUFQIQHUKP-UHFFFAOYSA-N 2-[3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorophenoxy]acetonitrile Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=CC(OCC#N)=C1 YLKAGUFQIQHUKP-UHFFFAOYSA-N 0.000 claims 1
- XNWIANXMRVMOOW-UHFFFAOYSA-N 2-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(2-cyanopyridin-4-yl)pyridin-3-yl]-1H-benzimidazole-4-carbonitrile Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(C=CC=C2N1)C#N)C1=CC(=NC=C1)C#N XNWIANXMRVMOOW-UHFFFAOYSA-N 0.000 claims 1
- IPQJYOUGNIQUGO-UHFFFAOYSA-N 2-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(3-cyano-4-fluorophenyl)pyridin-3-yl]-1H-benzimidazole-4-carbonitrile Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=CC(=C(C=C1)F)C#N)C1=NC2=C(N1)C=CC=C2C#N)C IPQJYOUGNIQUGO-UHFFFAOYSA-N 0.000 claims 1
- IPQJYOUGNIQUGO-VWLOTQADSA-N 2-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(3-cyano-4-fluorophenyl)pyridin-3-yl]-1H-benzimidazole-4-carbonitrile Chemical compound C[C@]1(N)CCN(C1)C1=C(C=NC=C1C1=CC(C#N)=C(F)C=C1)C1=NC2=CC=CC(C#N)=C2N1 IPQJYOUGNIQUGO-VWLOTQADSA-N 0.000 claims 1
- LKIOIKOIKDMFMV-VWLOTQADSA-N 2-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(3-cyanophenyl)pyridin-3-yl]-1H-benzimidazole-4-carbonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=CC(=CC=C1)C#N)C1=NC2=C(N1)C(=CC=C2)C#N)C LKIOIKOIKDMFMV-VWLOTQADSA-N 0.000 claims 1
- WWTIVTCZCYMMQH-KRWDZBQOSA-N 2-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(3-chloro-5-fluorophenyl)pyridin-3-yl]-3H-benzimidazole-5-carbonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=CC(Cl)=CC(F)=C1)C1=NC2=CC(=CC=C2N1)C#N WWTIVTCZCYMMQH-KRWDZBQOSA-N 0.000 claims 1
- RURNCBCZDOVMQQ-KRWDZBQOSA-N 2-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(3-cyano-4-fluorophenyl)pyridin-3-yl]-1H-benzimidazole-4-carbonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=CC(=C(C=C1)F)C#N)C1=NC2=C(N1)C=CC=C2C#N RURNCBCZDOVMQQ-KRWDZBQOSA-N 0.000 claims 1
- MOVVWDBTNAEZFW-INIZCTEOSA-N 2-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(3-cyanophenyl)pyridin-3-yl]-1H-benzimidazole-4-carboxamide Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=CC(=CC=C1)C#N)C1=NC2=C(N1)C=CC=C2C(=O)N MOVVWDBTNAEZFW-INIZCTEOSA-N 0.000 claims 1
- HXVZXDXGLKBBAU-INIZCTEOSA-N 2-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(3-cyanophenyl)pyridin-3-yl]-1H-benzimidazole-4-carboxylic acid Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=CC(=CC=C1)C#N)C1=NC2=C(N1)C=CC=C2C(=O)O HXVZXDXGLKBBAU-INIZCTEOSA-N 0.000 claims 1
- JHTNYXPNPZUDES-KRWDZBQOSA-N 2-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(3-cyanophenyl)pyridin-3-yl]-N-methyl-1H-benzimidazole-4-carboxamide Chemical compound CNC(=O)C1=C2N=C(NC2=CC=C1)C1=C(N2CC[C@H](N)C2)C(=CN=C1)C1=CC(=CC=C1)C#N JHTNYXPNPZUDES-KRWDZBQOSA-N 0.000 claims 1
- RNNRXNCZZUOJRD-LBPRGKRZSA-N 2-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,7-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-6-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC(F)=C2N1)C1=C(C#N)C(F)=CC=C1 RNNRXNCZZUOJRD-LBPRGKRZSA-N 0.000 claims 1
- AFNOHWGILDVVAH-ZDUSSCGKSA-N 2-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-6-chlorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=C(C#N)C(Cl)=CC=C1 AFNOHWGILDVVAH-ZDUSSCGKSA-N 0.000 claims 1
- QDZZGBIMECPPGD-UHFFFAOYSA-N 2-[4-[3-(aminomethyl)azetidin-1-yl]-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-1H-benzimidazole-4-carbonitrile Chemical compound CC1=CC(=CC(F)=C1)C1=CN=CC(C2=NC3=C(C=CC=C3N2)C#N)=C1N1CC(CN)C1 QDZZGBIMECPPGD-UHFFFAOYSA-N 0.000 claims 1
- HEQASOZGOWSBKH-UHFFFAOYSA-N 2-[4-[3-(aminomethyl)azetidin-1-yl]-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-3H-benzimidazole-5-carbonitrile Chemical compound CC1=CC(=CC(F)=C1)C1=CN=CC(C2=NC3=CC(=CC=C3N2)C#N)=C1N1CC(CN)C1 HEQASOZGOWSBKH-UHFFFAOYSA-N 0.000 claims 1
- WLLYFCFWMONUIN-UHFFFAOYSA-N 2-[4-[3-(aminomethyl)azetidin-1-yl]-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-6-fluoro-1H-benzimidazole-5-carbonitrile Chemical compound CC1=CC(=CC(F)=C1)C1=CN=CC(C2=NC3=CC(C#N)=C(F)C=C3N2)=C1N1CC(CN)C1 WLLYFCFWMONUIN-UHFFFAOYSA-N 0.000 claims 1
- KNRVDTSACYOLBG-UHFFFAOYSA-N 2-[4-[3-(aminomethyl)azetidin-1-yl]-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-7-fluoro-3H-benzimidazole-5-carbonitrile Chemical compound NCC1CN(C1)C1=C(C=NC=C1C1=CC(=CC(=C1)C)F)C1=NC2=C(N1)C=C(C=C2F)C#N KNRVDTSACYOLBG-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- QPFOQLGAOLFHEI-UHFFFAOYSA-N 3-[3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=CC(=C1)N1CCOC1=O QPFOQLGAOLFHEI-UHFFFAOYSA-N 0.000 claims 1
- BGRLDEDHBRUVJQ-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzamide Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C=1C=C(C(=O)N)C=C(C=1)F)C BGRLDEDHBRUVJQ-UHFFFAOYSA-N 0.000 claims 1
- FJEFPZRBPUXQSU-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=CC(=C1)C#N FJEFPZRBPUXQSU-UHFFFAOYSA-N 0.000 claims 1
- XRKXSJSJOICDAY-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-N,N-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC(=CC=C1)C1=C(N2CCC(C)(N)C2)C(=CN=C1)C1=NC2=C(F)C=CC=C2N1 XRKXSJSJOICDAY-UHFFFAOYSA-N 0.000 claims 1
- HVTJYSCYMFYVDP-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-N-methylbenzamide Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C=1C=C(C(=O)NC)C=CC=1)C HVTJYSCYMFYVDP-UHFFFAOYSA-N 0.000 claims 1
- RWKREBASWIVRFR-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C=1C=C(C#N)C=CC=1)C RWKREBASWIVRFR-UHFFFAOYSA-N 0.000 claims 1
- WDCZUFPJFYKFSX-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzamide Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC=CC(C(N)=O)=C2F)=C1N1CCC(C)(N)C1 WDCZUFPJFYKFSX-UHFFFAOYSA-N 0.000 claims 1
- BPKFYHPWURJURQ-DLBZAZTESA-N 3-[4-[(2R,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1C[C@@H](N(C1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C=1C=C(C#N)C=C(C=1)F)CO BPKFYHPWURJURQ-DLBZAZTESA-N 0.000 claims 1
- BPKFYHPWURJURQ-IRXDYDNUSA-N 3-[4-[(2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1C[C@@H](CO)N(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=CC(=C1)C#N BPKFYHPWURJURQ-IRXDYDNUSA-N 0.000 claims 1
- RCQXLZBXRPTSTG-RUZDIDTESA-N 3-[4-[(3R)-3-amino-3-(hydroxymethyl)pyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@]1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2C)C=1C=C(C#N)C=C(C=1)F)CO RCQXLZBXRPTSTG-RUZDIDTESA-N 0.000 claims 1
- WBNMUAMVUMUFII-RTBURBONSA-N 3-[4-[(3R,4R)-3-amino-4-fluoropyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@H]1CN(C[C@H]1F)c1c(cncc1-c1cccc(c1)C#N)-c1nc2c(F)cccc2[nH]1 WBNMUAMVUMUFII-RTBURBONSA-N 0.000 claims 1
- JJMMEOSKTMMFRC-UYAOXDASSA-N 3-[4-[(3R,4R)-3-amino-4-hydroxypyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@H]1CN(C[C@H]1O)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C=1C=C(C#N)C=CC=1 JJMMEOSKTMMFRC-UYAOXDASSA-N 0.000 claims 1
- OLWDHUBPSHBMFQ-TZIWHRDSSA-N 3-[4-[(3R,4R)-3-amino-4-methoxypyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CO[C@@H]1CN(C[C@H]1N)c1c(cncc1-c1cccc(c1)C#N)-c1nc2c(F)cccc2[nH]1 OLWDHUBPSHBMFQ-TZIWHRDSSA-N 0.000 claims 1
- WBNMUAMVUMUFII-RBUKOAKNSA-N 3-[4-[(3R,4S)-3-amino-4-fluoropyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@H]1CN(C[C@@H]1F)c1c(cncc1-c1cccc(c1)C#N)-c1nc2c(F)cccc2[nH]1 WBNMUAMVUMUFII-RBUKOAKNSA-N 0.000 claims 1
- JJMMEOSKTMMFRC-QUCCMNQESA-N 3-[4-[(3R,4S)-3-amino-4-hydroxypyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@H]1CN(C[C@@H]1O)c1c(cncc1-c1cccc(c1)C#N)-c1nc2c(F)cccc2[nH]1 JJMMEOSKTMMFRC-QUCCMNQESA-N 0.000 claims 1
- OLWDHUBPSHBMFQ-CTNGQTDRSA-N 3-[4-[(3R,4S)-3-amino-4-methoxypyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CO[C@H]1CN(C[C@H]1N)c1c(cncc1-c1cccc(c1)C#N)-c1nc2c(F)cccc2[nH]1 OLWDHUBPSHBMFQ-CTNGQTDRSA-N 0.000 claims 1
- RCQXLZBXRPTSTG-VWLOTQADSA-N 3-[4-[(3S)-3-amino-3-(hydroxymethyl)pyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2C)C=1C=C(C#N)C=C(C=1)F)CO RCQXLZBXRPTSTG-VWLOTQADSA-N 0.000 claims 1
- RWKREBASWIVRFR-DEOSSOPVSA-N 3-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound C[C@]1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=CC(=C1)C#N RWKREBASWIVRFR-DEOSSOPVSA-N 0.000 claims 1
- QIVSEUVGQLHMOY-IBGZPJMESA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1,4-dimethylbenzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CN1C2=CC=CC(C)=C2N=C1C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 QIVSEUVGQLHMOY-IBGZPJMESA-N 0.000 claims 1
- RPEQWZQNDQOWBU-IBGZPJMESA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1,7-dimethylbenzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CN1C(=NC2=CC=CC(C)=C12)C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 RPEQWZQNDQOWBU-IBGZPJMESA-N 0.000 claims 1
- XIJSGJGCVCMVHD-SFHVURJKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1-ethyl-4-fluorobenzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CCN1C2=CC=CC(F)=C2N=C1C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 XIJSGJGCVCMVHD-SFHVURJKSA-N 0.000 claims 1
- TVTVHNDUQZBQEO-SFHVURJKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1-ethyl-4-fluorobenzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CCN1C2=CC=CC(F)=C2N=C1C1=CN=CC(C2=CC=CC(=C2)C#N)=C1N1CC[C@H](N)C1 TVTVHNDUQZBQEO-SFHVURJKSA-N 0.000 claims 1
- GRKKNTKHFUVIKT-SFHVURJKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1-methylbenzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2)C=1C=C(C#N)C=C(C=1)F GRKKNTKHFUVIKT-SFHVURJKSA-N 0.000 claims 1
- NFZAKUOATMZJAA-FQEVSTJZSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1-propylbenzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CCCN1C2=CC=CC=C2N=C1C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 NFZAKUOATMZJAA-FQEVSTJZSA-N 0.000 claims 1
- WUQRTBNIRKGPSI-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=CC=CC=C2N1)C1=CC(F)=CC(=C1)C#N WUQRTBNIRKGPSI-KRWDZBQOSA-N 0.000 claims 1
- DOIBUDFCMUBRFP-ZDUSSCGKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,5,6,7-tetrafluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C(F)=C(F)C(F)=C2N1)C1=CC=CC(=C1)C#N DOIBUDFCMUBRFP-ZDUSSCGKSA-N 0.000 claims 1
- KICPCWXUQQHLOJ-HNNXBMFYSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,5-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC(=C2F)F)C=1C=C(C#N)C=C(C=1)F KICPCWXUQQHLOJ-HNNXBMFYSA-N 0.000 claims 1
- WPHBFRFGYPWDGB-HNNXBMFYSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,7-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC(F)=C2N1)C1=CC(F)=CC(=C1)C#N WPHBFRFGYPWDGB-HNNXBMFYSA-N 0.000 claims 1
- NONUQHZRSSKBIT-INIZCTEOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-bromo-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(Br)C=CC=C2N1)C1=CC=CC(=C1)C#N NONUQHZRSSKBIT-INIZCTEOSA-N 0.000 claims 1
- FISRMKVXFMAMPQ-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-chloro-1-methylbenzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2Cl)C=1C=C(C#N)C=C(C=1)F FISRMKVXFMAMPQ-KRWDZBQOSA-N 0.000 claims 1
- PANOLJWIMSTRFL-INIZCTEOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(Cl)C=CC=C2N1)C1=CC(F)=CC(=C1)C#N PANOLJWIMSTRFL-INIZCTEOSA-N 0.000 claims 1
- OXXIAXBWBQNQRD-IBGZPJMESA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-ethyl-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CCC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC=CC(=C2)C#N)=C1N1CC[C@H](N)C1 OXXIAXBWBQNQRD-IBGZPJMESA-N 0.000 claims 1
- IHWDQDKNSRSGSZ-IBGZPJMESA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-ethynyl-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(C=CC=C2N1)C#C)C1=CC=CC(=C1)C#N IHWDQDKNSRSGSZ-IBGZPJMESA-N 0.000 claims 1
- ICHBNQXFUJASEL-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1-methylbenzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CN1C2=CC=CC(F)=C2N=C1C1=CN=CC(C2=CC=CC(=C2)C#N)=C1N1CC[C@H](N)C1 ICHBNQXFUJASEL-KRWDZBQOSA-N 0.000 claims 1
- GUQHCIFRLUTGNQ-LBPRGKRZSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2,6-difluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=C(F)C(C#N)=C1F GUQHCIFRLUTGNQ-LBPRGKRZSA-N 0.000 claims 1
- PHSZRKAVRIBQBN-INIZCTEOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-chlorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(Cl)=CC(=C1)C#N PHSZRKAVRIBQBN-INIZCTEOSA-N 0.000 claims 1
- AYODVTGZTHONMD-HNNXBMFYSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzamide Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=CC(=C1)C(N)=O AYODVTGZTHONMD-HNNXBMFYSA-N 0.000 claims 1
- QNRAATFNBCBMPO-INIZCTEOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=CC(=C1)C#N QNRAATFNBCBMPO-INIZCTEOSA-N 0.000 claims 1
- OCJHZLPOCXOFRQ-AWEZNQCLSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorophenol Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=CC(O)=C1 OCJHZLPOCXOFRQ-AWEZNQCLSA-N 0.000 claims 1
- IYRKHMONMSFYSC-INIZCTEOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=CC(=C1)C#N IYRKHMONMSFYSC-INIZCTEOSA-N 0.000 claims 1
- OZKVNEVZCAUBCZ-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzamide Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(F)=CC(=C2)C(N)=O)=C1N1CC[C@H](N)C1 OZKVNEVZCAUBCZ-KRWDZBQOSA-N 0.000 claims 1
- UTCVPVMMHVQGPZ-SFHVURJKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 UTCVPVMMHVQGPZ-SFHVURJKSA-N 0.000 claims 1
- YQBFJDSGILSVCW-SFHVURJKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC=CC(=C2)C#N)=C1N1CC[C@H](N)C1 YQBFJDSGILSVCW-SFHVURJKSA-N 0.000 claims 1
- OHIVHPMPIJZAMU-IBGZPJMESA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-indol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C=1NC2=CC=CC(=C2C=1)C)C=1C=C(C#N)C=C(C=1)F OHIVHPMPIJZAMU-IBGZPJMESA-N 0.000 claims 1
- NWJHUIUKWIDBNZ-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(5-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CC1=C2N=C(NC2=CC=C1F)C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 NWJHUIUKWIDBNZ-KRWDZBQOSA-N 0.000 claims 1
- VBCIVKWAFWVSEB-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(6-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=CC=C(Cl)C=C2N1)C1=CC(F)=CC(=C1)C#N VBCIVKWAFWVSEB-KRWDZBQOSA-N 0.000 claims 1
- OEYXVRHHVPPZDZ-SFHVURJKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(6-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CC1=C2N=C(NC2=CC(F)=C1)C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 OEYXVRHHVPPZDZ-SFHVURJKSA-N 0.000 claims 1
- XUGKTGVMSKYYIX-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-chloro-1-methylbenzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C(=CC=C2)Cl)C=1C=C(C#N)C=C(C=1)F XUGKTGVMSKYYIX-KRWDZBQOSA-N 0.000 claims 1
- WGIBQFGWTMBHJV-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-fluoro-1-methylbenzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CN1C(=NC2=CC=CC(F)=C12)C1=CN=CC(C2=CC=CC(=C2)C#N)=C1N1CC[C@H](N)C1 WGIBQFGWTMBHJV-KRWDZBQOSA-N 0.000 claims 1
- DWKVCIJMEJZSQN-INIZCTEOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzamide Chemical compound CC1=C2N=C(NC2=C(F)C=C1)C1=CN=CC(C2=CC(F)=CC(=C2)C(N)=O)=C1N1CC[C@H](N)C1 DWKVCIJMEJZSQN-INIZCTEOSA-N 0.000 claims 1
- UJNUFHFWKHCQNO-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CC1=C2N=C(NC2=C(F)C=C1)C1=CN=CC(C2=CC(F)=CC(=C2)C#N)=C1N1CC[C@H](N)C1 UJNUFHFWKHCQNO-KRWDZBQOSA-N 0.000 claims 1
- OHQQNZHPDPITLY-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CC1=C2N=C(NC2=C(F)C=C1)C1=CN=CC(C2=CC=CC(=C2)C#N)=C1N1CC[C@H](N)C1 OHQQNZHPDPITLY-KRWDZBQOSA-N 0.000 claims 1
- WARRPZOKAHJEJN-FQEVSTJZSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-methyl-1H-indol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C=1NC2=C(C=CC=C2C=1)C)C=1C=C(C#N)C=C(C=1)F WARRPZOKAHJEJN-FQEVSTJZSA-N 0.000 claims 1
- SILANMUOYGFQSZ-IBGZPJMESA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-[1-(cyanomethyl)benzimidazol-2-yl]pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=CC=CC=C2N1CC#N)C1=CC(F)=CC(=C1)C#N SILANMUOYGFQSZ-IBGZPJMESA-N 0.000 claims 1
- RCEZPGUANWCWRX-SFHVURJKSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-[4-(hydroxymethyl)-1H-benzimidazol-2-yl]pyridin-3-yl]benzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=CC=CC(CO)=C2N1)C1=CC=CC(=C1)C#N RCEZPGUANWCWRX-SFHVURJKSA-N 0.000 claims 1
- NIVUDCBABGJBDD-UKILVPOCSA-N 3-[4-[(3S,4R)-3-amino-4-phenylpyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@H]1CN(C[C@H]1c1ccccc1)c1c(cncc1-c1cccc(c1)C#N)-c1nc2c(F)cccc2[nH]1 NIVUDCBABGJBDD-UKILVPOCSA-N 0.000 claims 1
- UTOKGWLBRRKBQL-UHFFFAOYSA-N 3-[4-[3-(1-aminoethyl)azetidin-1-yl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound CC(N)C1CN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=CC(F)=CC(=C1)C#N UTOKGWLBRRKBQL-UHFFFAOYSA-N 0.000 claims 1
- KLDXZXUITWHHKF-UHFFFAOYSA-N 3-[4-[3-(aminomethyl)azetidin-1-yl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound NCC1CN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=CC(F)=CC(=C1)C#N KLDXZXUITWHHKF-UHFFFAOYSA-N 0.000 claims 1
- NGHCNUQPYLXIMZ-UHFFFAOYSA-N 3-[4-[3-(aminomethyl)azetidin-1-yl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound NCC1CN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=CC=CC(=C1)C#N NGHCNUQPYLXIMZ-UHFFFAOYSA-N 0.000 claims 1
- NTFFAVAOEXEXDY-UHFFFAOYSA-N 3-[4-[3-amino-3-(hydroxymethyl)pyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound NC1(CO)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=CC(=C1)C#N NTFFAVAOEXEXDY-UHFFFAOYSA-N 0.000 claims 1
- KVJHWQQAIRFGNL-UHFFFAOYSA-N 3-[4-[3-amino-3-(trifluoromethyl)pyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound NC1(CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=CC(=C1)C#N)C(F)(F)F KVJHWQQAIRFGNL-UHFFFAOYSA-N 0.000 claims 1
- OXHFCAIOODMINV-UHFFFAOYSA-N 3-[4-[3-amino-4-(trifluoromethyl)pyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound NC1CN(CC1C(F)(F)F)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=CC(=C1)C#N OXHFCAIOODMINV-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- QAVULCRFSRRZRB-UHFFFAOYSA-N 4-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2Cl)C1=CC(=NC=C1)C#N)C QAVULCRFSRRZRB-UHFFFAOYSA-N 0.000 claims 1
- VWBJYMFKUTZDMX-UHFFFAOYSA-N 4-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]pyridin-2-amine Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C1=CC(=NC=C1)N)C VWBJYMFKUTZDMX-UHFFFAOYSA-N 0.000 claims 1
- PDDCYDRYZNMDCN-UHFFFAOYSA-N 4-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(=NC=C1)C#N PDDCYDRYZNMDCN-UHFFFAOYSA-N 0.000 claims 1
- LXJXPVBAJGKDSA-UHFFFAOYSA-N 4-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2C)C1=CC(=NC=C1)C#N)C LXJXPVBAJGKDSA-UHFFFAOYSA-N 0.000 claims 1
- YFDSHUCOXJEBCA-UHFFFAOYSA-N 4-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(=NC=C2)C(N)=O)=C1N1CCC(C)(N)C1 YFDSHUCOXJEBCA-UHFFFAOYSA-N 0.000 claims 1
- HRTDUKVWBYMBEV-UHFFFAOYSA-N 4-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-[4-(trifluoromethyl)-1H-benzimidazol-2-yl]pyridin-3-yl]pyridine-2-carbonitrile Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(C=CC=C2N1)C(F)(F)F)C1=CC(=NC=C1)C#N HRTDUKVWBYMBEV-UHFFFAOYSA-N 0.000 claims 1
- YUKIXCKOLGEKAF-VWLOTQADSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(1,4-dimethylbenzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2C)C1=CC(=NC=C1)C#N)C YUKIXCKOLGEKAF-VWLOTQADSA-N 0.000 claims 1
- QBPXZVQQHQDLIN-DEOSSOPVSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-chloro-1-methylbenzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2Cl)C1=CC(=NC=C1)C#N)C QBPXZVQQHQDLIN-DEOSSOPVSA-N 0.000 claims 1
- QAVULCRFSRRZRB-QHCPKHFHSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound C[C@]1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(Cl)C=CC=C2N1)C1=CC(=NC=C1)C#N QAVULCRFSRRZRB-QHCPKHFHSA-N 0.000 claims 1
- YWXVJKJQMWPNMA-DEOSSOPVSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-fluoro-1-methylbenzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2F)C1=CC(=NC=C1)C#N)C YWXVJKJQMWPNMA-DEOSSOPVSA-N 0.000 claims 1
- PDDCYDRYZNMDCN-QHCPKHFHSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound C[C@]1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(=NC=C1)C#N PDDCYDRYZNMDCN-QHCPKHFHSA-N 0.000 claims 1
- LXJXPVBAJGKDSA-DEOSSOPVSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(=NC=C2)C#N)=C1N1CC[C@](C)(N)C1 LXJXPVBAJGKDSA-DEOSSOPVSA-N 0.000 claims 1
- YFDSHUCOXJEBCA-DEOSSOPVSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(=NC=C2)C(N)=O)=C1N1CC[C@](C)(N)C1 YFDSHUCOXJEBCA-DEOSSOPVSA-N 0.000 claims 1
- LWPFNMFNZKRULK-DEOSSOPVSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(6-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound CC1=C2N=C(NC2=CC(F)=C1)C1=CN=CC(C2=CC(=NC=C2)C#N)=C1N1CC[C@](C)(N)C1 LWPFNMFNZKRULK-DEOSSOPVSA-N 0.000 claims 1
- HRTDUKVWBYMBEV-QHCPKHFHSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-[4-(trifluoromethyl)-1H-benzimidazol-2-yl]pyridin-3-yl]pyridine-2-carbonitrile Chemical compound C[C@]1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=CC=CC(=C2N1)C(F)(F)F)C1=CC(=NC=C1)C#N HRTDUKVWBYMBEV-QHCPKHFHSA-N 0.000 claims 1
- IYFAJMBPQGDFHN-AWEZNQCLSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(Cl)C=CC=C2N1)C1=CC(=NC=C1)C#N IYFAJMBPQGDFHN-AWEZNQCLSA-N 0.000 claims 1
- CTGUWQKPQCKJMS-HNNXBMFYSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(F)=C(C=C1)C#N CTGUWQKPQCKJMS-HNNXBMFYSA-N 0.000 claims 1
- PETJIDKQQFOWRK-AWEZNQCLSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-6-methylpyridin-2-amine Chemical compound CC1=CC(=CC(N)=N1)C1=C(N2CC[C@H](N)C2)C(=CN=C1)C1=NC2=C(F)C=CC=C2N1 PETJIDKQQFOWRK-AWEZNQCLSA-N 0.000 claims 1
- SERJLYXIPFMCBW-AWEZNQCLSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-N-methylpyridin-2-amine Chemical compound CNC1=NC=CC(=C1)C1=C(N2CC[C@H](N)C2)C(=CN=C1)C1=NC2=C(F)C=CC=C2N1 SERJLYXIPFMCBW-AWEZNQCLSA-N 0.000 claims 1
- ZGIOEOXXMMRBPD-INIZCTEOSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=C(C=C1)C#N ZGIOEOXXMMRBPD-INIZCTEOSA-N 0.000 claims 1
- LIOBCCFACVDICQ-INIZCTEOSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2C)C1=CC(=NC=C1)C#N LIOBCCFACVDICQ-INIZCTEOSA-N 0.000 claims 1
- ATCZRZOHPZOTHG-HNNXBMFYSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound CC1=C2N=C(NC2=C(F)C=C1)C1=CN=CC(C2=CC(=NC=C2)C#N)=C1N1CC[C@H](N)C1 ATCZRZOHPZOTHG-HNNXBMFYSA-N 0.000 claims 1
- RZQCBWISWDFWFI-AWEZNQCLSA-N 4-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carboxamide Chemical compound CC1=C2N=C(NC2=C(F)C=C1)C1=CN=CC(C2=CC(=NC=C2)C(N)=O)=C1N1CC[C@H](N)C1 RZQCBWISWDFWFI-AWEZNQCLSA-N 0.000 claims 1
- MUGNNSGPAFOWQV-UHFFFAOYSA-N 5-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzamide Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(C(N)=O)=C(F)C=C1 MUGNNSGPAFOWQV-UHFFFAOYSA-N 0.000 claims 1
- AGPJYVQCKWLVHE-UHFFFAOYSA-N 5-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-N,N-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=C(C=N1)C1=C(N2CCC(C)(N)C2)C(=CN=C1)C1=NC2=C(F)C=CC=C2N1 AGPJYVQCKWLVHE-UHFFFAOYSA-N 0.000 claims 1
- JJQUKBMOCHQUOV-UHFFFAOYSA-N 5-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2,3-difluorobenzamide Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(C(N)=O)=C(F)C(F)=C2)=C1N1CCC(C)(N)C1 JJQUKBMOCHQUOV-UHFFFAOYSA-N 0.000 claims 1
- UYONRTDOYMGOGS-UHFFFAOYSA-N 5-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2,3-difluorobenzoic acid Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(C(O)=O)=C(F)C(F)=C2)=C1N1CCC(C)(N)C1 UYONRTDOYMGOGS-UHFFFAOYSA-N 0.000 claims 1
- CZZVZVSFMVVGFL-UHFFFAOYSA-N 5-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzamide Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(C(N)=O)=C(F)C=C2)=C1N1CCC(C)(N)C1 CZZVZVSFMVVGFL-UHFFFAOYSA-N 0.000 claims 1
- RFELHLOOOUQPFF-UHFFFAOYSA-N 5-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(7-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzamide Chemical compound CC1=C2N=C(NC2=C(F)C=C1)C1=CN=CC(C2=CC(C(N)=O)=C(F)C=C2)=C1N1CCC(C)(N)C1 RFELHLOOOUQPFF-UHFFFAOYSA-N 0.000 claims 1
- ULCLLTMGMVEUQF-SFHVURJKSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1,4-dimethylbenzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound CN1C2=CC=CC(C)=C2N=C1C1=CN=CC(C2=CC(C#N)=C(F)C=C2)=C1N1CC[C@H](N)C1 ULCLLTMGMVEUQF-SFHVURJKSA-N 0.000 claims 1
- BGJAHJUEHPQDEF-SFHVURJKSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1,7-dimethylbenzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound CN1C(=NC2=CC=CC(C)=C12)C1=CN=CC(C2=CC(C#N)=C(F)C=C2)=C1N1CC[C@H](N)C1 BGJAHJUEHPQDEF-SFHVURJKSA-N 0.000 claims 1
- JINBZXPTWTVCOE-KRWDZBQOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(1-ethyl-4-fluorobenzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound CCN1C2=CC=CC(F)=C2N=C1C1=CN=CC(C2=CC(C#N)=C(F)C=C2)=C1N1CC[C@H](N)C1 JINBZXPTWTVCOE-KRWDZBQOSA-N 0.000 claims 1
- KBDIPWWMSATCEK-AWEZNQCLSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,5-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC(=C2F)F)C=1C=CC(=C(C#N)C=1)F KBDIPWWMSATCEK-AWEZNQCLSA-N 0.000 claims 1
- CADUSAZAKPBBIN-LBPRGKRZSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,7-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzamide Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC(F)=C2N1)C1=CC(C(N)=O)=C(F)C=C1 CADUSAZAKPBBIN-LBPRGKRZSA-N 0.000 claims 1
- LQMRZHSJVHSFHY-AWEZNQCLSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,7-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC(F)=C2N1)C1=CC(C#N)=C(F)C=C1 LQMRZHSJVHSFHY-AWEZNQCLSA-N 0.000 claims 1
- MGTYFIRWYCBDDG-INIZCTEOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,7-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-methylbenzonitrile Chemical compound CC1=C(C=C(C=C1)C1=C(N2CC[C@H](N)C2)C(=CN=C1)C1=NC2=C(F)C=CC(F)=C2N1)C#N MGTYFIRWYCBDDG-INIZCTEOSA-N 0.000 claims 1
- NSXIKKSJVIJGIW-INIZCTEOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-chloro-1-methylbenzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2Cl)C=1C=CC(=C(C#N)C=1)F NSXIKKSJVIJGIW-INIZCTEOSA-N 0.000 claims 1
- KYANISGOLFFMNZ-HNNXBMFYSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(Cl)C=CC=C2N1)C1=CC(C#N)=C(F)C=C1 KYANISGOLFFMNZ-HNNXBMFYSA-N 0.000 claims 1
- GQVBSRYVQSJDNT-HNNXBMFYSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-chlorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(C#N)=C(Cl)C=C1 GQVBSRYVQSJDNT-HNNXBMFYSA-N 0.000 claims 1
- OSPNXWNNUPHDTD-HNNXBMFYSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(C#N)=C(F)C=C1 OSPNXWNNUPHDTD-HNNXBMFYSA-N 0.000 claims 1
- WUSCAPAWEWSPFO-HNNXBMFYSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-hydroxybenzonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(C#N)=C(O)C=C1 WUSCAPAWEWSPFO-HNNXBMFYSA-N 0.000 claims 1
- HOUYPJWKRRMHLV-AWEZNQCLSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-methoxybenzamide Chemical compound COC1=C(C=C(C=C1)C1=C(N2CC[C@H](N)C2)C(=CN=C1)C1=NC2=C(F)C=CC=C2N1)C(N)=O HOUYPJWKRRMHLV-AWEZNQCLSA-N 0.000 claims 1
- RRPDZSUBOFAPEJ-LBPRGKRZSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]thiophene-2-carbonitrile Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=C(S1)C#N RRPDZSUBOFAPEJ-LBPRGKRZSA-N 0.000 claims 1
- HAKNMURZGCNYIE-INIZCTEOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2,3-difluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2C)C=1C=C(C(=C(C#N)C=1)F)F HAKNMURZGCNYIE-INIZCTEOSA-N 0.000 claims 1
- CHSWFFWVRVXCOU-KRWDZBQOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2-chlorobenzonitrile Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(C#N)=C(Cl)C=C2)=C1N1CC[C@H](N)C1 CHSWFFWVRVXCOU-KRWDZBQOSA-N 0.000 claims 1
- FIHFKBSEBWEYFH-KRWDZBQOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC(C#N)=C(F)C=C2)=C1N1CC[C@H](N)C1 FIHFKBSEBWEYFH-KRWDZBQOSA-N 0.000 claims 1
- WAAIEJATBTXTLX-INIZCTEOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-chloro-1-methylbenzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C(=CC=C2)Cl)C=1C=CC(=C(C#N)C=1)F WAAIEJATBTXTLX-INIZCTEOSA-N 0.000 claims 1
- PMAJEYRMPOZGFS-HNNXBMFYSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-[4-(trifluoromethyl)-1H-benzimidazol-2-yl]pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@H]1CCN(C1)c1c(cncc1-c1ccc(F)c(c1)C#N)-c1nc2c(cccc2[nH]1)C(F)(F)F PMAJEYRMPOZGFS-HNNXBMFYSA-N 0.000 claims 1
- VOPRWPRIPAEUIT-UHFFFAOYSA-N 5-[4-[3-(1-aminoethyl)azetidin-1-yl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound CC(N)C1CN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=CC(C#N)=C(F)C=C1 VOPRWPRIPAEUIT-UHFFFAOYSA-N 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
- FJYOJPXPOSXFJF-UHFFFAOYSA-N [1-[3-(3-chloro-2-fluorophenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cccc(Cl)c1F)-c1nc2c(F)cc(F)cc2[nH]1 FJYOJPXPOSXFJF-UHFFFAOYSA-N 0.000 claims 1
- RJTJQZJYVLPKSR-UHFFFAOYSA-N [1-[3-(3-chloro-2-methylphenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1c(Cl)cccc1-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 RJTJQZJYVLPKSR-UHFFFAOYSA-N 0.000 claims 1
- SYPPSOQAXJIXKM-UHFFFAOYSA-N [1-[3-(3-chloro-5-fluorophenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]-3-fluoroazetidin-3-yl]methanamine Chemical compound NCC1(F)CN(C1)c1c(cncc1-c1cc(F)cc(Cl)c1)-c1nc2c(F)cc(F)cc2[nH]1 SYPPSOQAXJIXKM-UHFFFAOYSA-N 0.000 claims 1
- SFZFUJHMVTYDAJ-UHFFFAOYSA-N [1-[3-(3-chloro-5-fluorophenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cc(F)cc(Cl)c1)-c1nc2c(F)cc(F)cc2[nH]1 SFZFUJHMVTYDAJ-UHFFFAOYSA-N 0.000 claims 1
- PTGDTJKNOAICKA-UHFFFAOYSA-N [1-[3-(3-chloro-5-methoxyphenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound COc1cc(Cl)cc(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 PTGDTJKNOAICKA-UHFFFAOYSA-N 0.000 claims 1
- NXNHCTAHBCGXKL-UHFFFAOYSA-N [1-[3-(3-chloro-5-methylphenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(Cl)cc(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 NXNHCTAHBCGXKL-UHFFFAOYSA-N 0.000 claims 1
- CQSUPACLVXVBPS-UHFFFAOYSA-N [1-[3-(3-fluoro-5-methylphenyl)-5-(1H-imidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2ncc[nH]2)c1N1CC(CN)C1 CQSUPACLVXVBPS-UHFFFAOYSA-N 0.000 claims 1
- MAVQAJDVYVEQBI-UHFFFAOYSA-N [1-[3-(4,5-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2nc3c(F)c(F)ccc3[nH]2)c1N1CC(CN)C1 MAVQAJDVYVEQBI-UHFFFAOYSA-N 0.000 claims 1
- NKPHGWMKBSQUAV-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(1-methylpyrazol-4-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cn1cc(cn1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 NKPHGWMKBSQUAV-UHFFFAOYSA-N 0.000 claims 1
- GQACYACENQQYGW-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(2-fluoro-3-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cccc(c1F)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 GQACYACENQQYGW-UHFFFAOYSA-N 0.000 claims 1
- GCIYXSMCYXSCMH-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(2-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1ccc(F)c(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 GCIYXSMCYXSCMH-UHFFFAOYSA-N 0.000 claims 1
- IBKMMRIGTODZNO-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(2-fluorophenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1ccccc1F)-c1nc2c(F)cc(F)cc2[nH]1 IBKMMRIGTODZNO-UHFFFAOYSA-N 0.000 claims 1
- CNFLYIQDHKSTDL-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3,4,5-trifluorophenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cc(F)c(F)c(F)c1)-c1nc2c(F)cc(F)cc2[nH]1 CNFLYIQDHKSTDL-UHFFFAOYSA-N 0.000 claims 1
- USTKGPYLYSWMFE-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-4-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1ccc(cc1F)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 USTKGPYLYSWMFE-UHFFFAOYSA-N 0.000 claims 1
- OEFYLNXRMAJXIE-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methoxyphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound COc1cc(F)cc(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 OEFYLNXRMAJXIE-UHFFFAOYSA-N 0.000 claims 1
- YEACCEDRWDFZPO-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]-3-methylazetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(C)(CN)C1 YEACCEDRWDFZPO-UHFFFAOYSA-N 0.000 claims 1
- MYHJKTDZAPCJBO-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluorophenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cccc(F)c1)-c1nc2c(F)cc(F)cc2[nH]1 MYHJKTDZAPCJBO-UHFFFAOYSA-N 0.000 claims 1
- SGOHDXJRSVZVBK-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cccc(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 SGOHDXJRSVZVBK-UHFFFAOYSA-N 0.000 claims 1
- LBPCZBNSWVMKGB-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(4-fluoro-3-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(ccc1F)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 LBPCZBNSWVMKGB-UHFFFAOYSA-N 0.000 claims 1
- HASJYMBVXCMILU-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(4-fluorophenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1ccc(F)cc1)-c1nc2c(F)cc(F)cc2[nH]1 HASJYMBVXCMILU-UHFFFAOYSA-N 0.000 claims 1
- GGCJVBOPIWZNDJ-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(4-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1ccc(cc1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 GGCJVBOPIWZNDJ-UHFFFAOYSA-N 0.000 claims 1
- LYQSWJHWMYZXMO-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(5-fluoro-2-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1ccc(F)cc1-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 LYQSWJHWMYZXMO-UHFFFAOYSA-N 0.000 claims 1
- UVKVOBUPCVTNLN-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(5-methylpyridin-3-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cncc(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 UVKVOBUPCVTNLN-UHFFFAOYSA-N 0.000 claims 1
- OSMFGYVOLIVLIF-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-phenylpyridin-4-yl]azetidin-3-yl]methanamine Chemical compound C1(C=2NC3=C(N=2)C(=CC(F)=C3)F)=C(N2CC(CN)C2)C(C2=CC=CC=C2)=CN=C1 OSMFGYVOLIVLIF-UHFFFAOYSA-N 0.000 claims 1
- GBYLIPBKYAILGP-UHFFFAOYSA-N [1-[3-(4,7-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2nc3c(F)ccc(F)c3[nH]2)c1N1CC(CN)C1 GBYLIPBKYAILGP-UHFFFAOYSA-N 0.000 claims 1
- NRRVPINVTOPDTO-UHFFFAOYSA-N [1-[3-(4-fluoro-1-methylbenzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound C=1(C=NC=C(C=1N1CC(CN)C1)C1=CC(C)=CC(F)=C1)C=1N(C2=CC=CC(F)=C2N=1)C NRRVPINVTOPDTO-UHFFFAOYSA-N 0.000 claims 1
- RKADVWSXXAPBLI-UHFFFAOYSA-N [1-[3-(5,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2nc3cc(F)c(F)cc3[nH]2)c1N1CC(CN)C1 RKADVWSXXAPBLI-UHFFFAOYSA-N 0.000 claims 1
- ZZXFOIUQNMPNIU-UHFFFAOYSA-N [1-[3-(5-chloro-6-fluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound ClC1=CC2=C(NC(=N2)C=2C=NC=C(C=2N2CC(C2)CN)C2=CC(=CC(=C2)C)F)C=C1F ZZXFOIUQNMPNIU-UHFFFAOYSA-N 0.000 claims 1
- YYRGCSYZXJDZOG-UHFFFAOYSA-N [1-[3-(6-chloro-4-fluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound ClC=1C=C(C2=C(NC(=N2)C=2C=NC=C(C=2N2CC(C2)CN)C2=CC(=CC(=C2)C)F)C=1)F YYRGCSYZXJDZOG-UHFFFAOYSA-N 0.000 claims 1
- GKYLFJCFVGDTKL-UHFFFAOYSA-N [1-[3-(6-fluoro-4-methoxy-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound FC=1C=C(C2=C(NC(=N2)C=2C=NC=C(C=2N2CC(C2)CN)C2=CC(=CC(=C2)C)F)C=1)OC GKYLFJCFVGDTKL-UHFFFAOYSA-N 0.000 claims 1
- TVRVQVAHPMTCFP-UHFFFAOYSA-N [1-[3-(7-fluoro-1-methylbenzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound CN1C(=NC2=CC=CC(F)=C12)C1=C(N2CC(CN)C2)C(=CN=C1)C1=CC(F)=CC(C)=C1 TVRVQVAHPMTCFP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 208000033066 hyperinsulinemic hypoglycemia Diseases 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862629377P | 2018-02-12 | 2018-02-12 | |
| US62/629,377 | 2018-02-12 | ||
| US201862673042P | 2018-05-17 | 2018-05-17 | |
| US62/673,042 | 2018-05-17 | ||
| US201862724421P | 2018-08-29 | 2018-08-29 | |
| US62/724,421 | 2018-08-29 | ||
| PCT/US2019/017529 WO2019157458A1 (en) | 2018-02-12 | 2019-02-11 | Somatostatin modulators and uses thereof |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021512889A JP2021512889A (ja) | 2021-05-20 |
| JP2021512889A5 JP2021512889A5 (https=) | 2022-02-21 |
| JPWO2019157458A5 true JPWO2019157458A5 (https=) | 2022-02-21 |
| JP7365347B2 JP7365347B2 (ja) | 2023-10-19 |
Family
ID=67548490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020542437A Active JP7365347B2 (ja) | 2018-02-12 | 2019-02-11 | ソマトスタチンモジュレーターおよびその使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11608335B2 (https=) |
| EP (1) | EP3752498B1 (https=) |
| JP (1) | JP7365347B2 (https=) |
| MA (1) | MA51840A (https=) |
| WO (1) | WO2019157458A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018170284A1 (en) | 2017-03-16 | 2018-09-20 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| EP3752498B1 (en) | 2018-02-12 | 2023-06-28 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| AR116424A1 (es) | 2018-09-18 | 2021-05-05 | Crinetics Pharmaceuticals Inc | Moduladores de la somatostatina y usos de los mismos |
| TWI841768B (zh) | 2019-08-14 | 2024-05-11 | 美商克林提克斯醫藥股份有限公司 | 非肽生長抑制素(somatostatin)5型受體激動劑及其用途 |
| EP4294797A1 (en) | 2021-02-17 | 2023-12-27 | Crinetics Pharmaceuticals, Inc. | Crystalline forms of a somatostatin modulator |
| CA3207382A1 (en) * | 2021-02-17 | 2022-08-25 | Christine FERRARA-COOK | Somatostatin receptor type 5 agonist for the treatment of hyperinsulinism |
| AU2023366475A1 (en) * | 2022-10-28 | 2025-05-29 | Exelixis, Inc. | Somatostatin receptor 2 agonists and uses thereof |
| JP2026500913A (ja) | 2022-12-13 | 2026-01-09 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンサブタイプ－２受容体（ｓｓｔ２ｒ）標的化治療薬及びその使用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6127343A (en) | 1996-05-14 | 2000-10-03 | Novo Nordisk A/S | Somatostatin agonists and antagonists |
| US6025372A (en) | 1997-04-04 | 2000-02-15 | Merck & Co., Inc. | Somatostatin agonists |
| FR2802206B1 (fr) | 1999-12-14 | 2005-04-22 | Sod Conseils Rech Applic | Derives de 4-aminopiperidine et leur utilisation en tant que medicament |
| US20060281764A1 (en) | 2005-06-10 | 2006-12-14 | Gaul Michael D | Aminopyrimidines as kinase modulators |
| CA2644929A1 (en) * | 2006-03-13 | 2008-05-02 | Merck & Co., Inc. | Somatostatin agonists |
| EP2054385A2 (en) | 2006-08-15 | 2009-05-06 | F. Hoffmann-Roche AG | Phenyl, pyridine and quinoline derivatives |
| EP2211619A1 (en) | 2007-10-18 | 2010-08-04 | Merck Sharp & Dohme Corp. | Substituted 1,2,4-oxadiazoles and analogs thereof as cb2 receptor modulators, useful in the treatment of pain, respiratory and non-respiratory diseases |
| CA2729220A1 (en) | 2008-06-25 | 2009-12-30 | Envivo Pharmaceuticals, Inc. | Di-substituted phenyl compounds |
| GB0818241D0 (en) | 2008-10-06 | 2008-11-12 | Cancer Res Technology | Compounds and their use |
| CA2772194A1 (en) | 2009-09-01 | 2011-03-10 | Pfizer Inc. | Benzimidazole derivatives |
| CA2799414A1 (en) | 2010-05-18 | 2011-11-24 | Merck Sharp & Dohme Corp. | Spiro isoxazoline compounds as sstr5 antagonists |
| GB201008290D0 (en) | 2010-05-18 | 2010-06-30 | Syngenta Ltd | Chemical compounds |
| WO2014007228A1 (ja) * | 2012-07-03 | 2014-01-09 | 小野薬品工業株式会社 | ソマトスタチン受容体作動活性を有する化合物およびその医薬用途 |
| AU2014325078B2 (en) * | 2013-09-30 | 2018-10-25 | Ono Pharmaceutical Co., Ltd. | Compound having agonistic activity to somatostatin receptor and medicinal use thereof |
| CN105579524B (zh) | 2013-10-02 | 2018-05-04 | 株式会社可乐丽 | 树脂组合物、多层片、包装材料和容器 |
| HRP20221279T1 (hr) | 2016-07-14 | 2022-12-23 | Crinetics Pharmaceuticals, Inc. | Modulatori somatostatina i njihove uporabe |
| CN110300749A (zh) | 2017-02-08 | 2019-10-01 | 小野药品工业株式会社 | 具有生长抑素受体激动活性的化合物及其医药用途 |
| WO2018170284A1 (en) * | 2017-03-16 | 2018-09-20 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| US11028068B2 (en) | 2017-07-25 | 2021-06-08 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| EP3752498B1 (en) | 2018-02-12 | 2023-06-28 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| AR116424A1 (es) | 2018-09-18 | 2021-05-05 | Crinetics Pharmaceuticals Inc | Moduladores de la somatostatina y usos de los mismos |
| TWI841768B (zh) | 2019-08-14 | 2024-05-11 | 美商克林提克斯醫藥股份有限公司 | 非肽生長抑制素(somatostatin)5型受體激動劑及其用途 |
-
2019
- 2019-02-11 EP EP19751144.7A patent/EP3752498B1/en active Active
- 2019-02-11 US US16/968,533 patent/US11608335B2/en active Active
- 2019-02-11 WO PCT/US2019/017529 patent/WO2019157458A1/en not_active Ceased
- 2019-02-11 MA MA051840A patent/MA51840A/fr unknown
- 2019-02-11 JP JP2020542437A patent/JP7365347B2/ja active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2021512889A5 (https=) | ||
| RU2317291C2 (ru) | Производные пиримидина в качестве модуляторов рецептора инсулинподобного фактора роста 1 (igf-1), фармацевтическая композиция, способы получения (варианты) и применение | |
| JP2019518036A5 (https=) | ||
| JP3930560B2 (ja) | 炎症の処置のための１，２−置換イミダゾリル化合物 | |
| RU2492167C2 (ru) | Производные аминотриазола в качестве агонистов alх | |
| RU2006127420A (ru) | Новое 2-гетероарил-замещенное производное бензимидазола | |
| JP2018535999A5 (https=) | ||
| RU2016141646A (ru) | Ингибиторы trka киназы, основанные на них композиции и способы | |
| JP2018530591A5 (https=) | ||
| RU2019132212A (ru) | Селективные ингибиторы hdac6 | |
| JP2007531752A5 (https=) | ||
| HRP20170506T1 (hr) | Dihidropiridon p1 kao inhibitori xia faktora | |
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| JP2019537571A5 (https=) | ||
| RU2016108753A (ru) | Ингибиторы ферментов | |
| JP2020533347A5 (https=) | ||
| JP2015533157A5 (https=) | ||
| JP2014511869A5 (https=) | ||
| RU2011153788A (ru) | Гетероциклические противовирусные соединения | |
| JPWO2019157458A5 (https=) | ||
| RU2015122698A (ru) | Производное пиридина | |
| CA2575003A1 (en) | Potassium channel inhibitors | |
| RU2017118562A (ru) | Соединения-антагонисты дофаминового d3-рецептора | |
| RU2003115612A (ru) | Производные амидоалкилпиперидинов и амидоалкилпиперазинов, пригодные для лечения нарушений нервной системы | |
| JP2018521119A5 (https=) |