JP7365347B2 - ソマトスタチンモジュレーターおよびその使用 - Google Patents

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Publication number

JP7365347B2

JP7365347B2 JP2020542437A JP2020542437A JP7365347B2 JP 7365347 B2 JP7365347 B2 JP 7365347B2 JP 2020542437 A JP2020542437 A JP 2020542437A JP 2020542437 A JP2020542437 A JP 2020542437A JP 7365347 B2 JP7365347 B2 JP 7365347B2

Authority

JP

Japan

Prior art keywords

pyridin

benzodiazol

fluoro

substituted

unsubstituted

Prior art date

2018-02-12

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.)

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• 108010056088 Somatostatin Proteins 0.000 title description 24
• 102000005157 Somatostatin Human genes 0.000 title description 23
• NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 title description 23
• 229960000553 somatostatin Drugs 0.000 title description 23
• 150000001875 compounds Chemical class 0.000 claims description 391
• 239000000203 mixture Substances 0.000 claims description 159
• 150000003839 salts Chemical class 0.000 claims description 100
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 71
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 59
• 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 description 56
• 239000012453 solvate Substances 0.000 claims description 52
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 48
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 238000011282 treatment Methods 0.000 claims description 39
• 239000003814 drug Substances 0.000 claims description 38
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 38
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 33
• 229910052731 fluorine Inorganic materials 0.000 claims description 30
• 102000004877 Insulin Human genes 0.000 claims description 28
• 108090001061 Insulin Proteins 0.000 claims description 28
• 229940125396 insulin Drugs 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 229910052801 chlorine Inorganic materials 0.000 claims description 24
• 229940079593 drug Drugs 0.000 claims description 23
• 201000008980 hyperinsulinism Diseases 0.000 claims description 23
• 125000002950 monocyclic group Chemical group 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• 230000002218 hypoglycaemic effect Effects 0.000 claims description 18
• 208000013016 Hypoglycemia Diseases 0.000 claims description 17
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 13
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 12
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 10
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 7
• SAVGKRODXUPDNR-KRWDZBQOSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-[3-fluoro-5-(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)F SAVGKRODXUPDNR-KRWDZBQOSA-N 0.000 claims description 6
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
• 208000033066 hyperinsulinemic hypoglycemia Diseases 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• GJNLDXPKEDAZJI-IEBWSBKVSA-N (3R,4S)-4-amino-1-[3-(3-cyanophenyl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidine-3-carboxamide Chemical compound N[C@H]1[C@@H](CN(C1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C1=CC(=CC=C1)C#N)C(=O)N GJNLDXPKEDAZJI-IEBWSBKVSA-N 0.000 claims description 5
• BVSDVAIOFHKVEI-DEOSSOPVSA-N 3-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-5-fluorobenzamide Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=C(C(=O)N)C=C(C=1)F)C BVSDVAIOFHKVEI-DEOSSOPVSA-N 0.000 claims description 5
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 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 description 4
• CDAMFUZFIZUPHW-DEOSSOPVSA-N 2-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(3-cyano-4-fluorophenyl)pyridin-3-yl]-1H-imidazo[4,5-b]pyridine-7-carbonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=CC(=C(C=C1)F)C#N)C=1NC=2C(=NC=CC=2C#N)N=1)C CDAMFUZFIZUPHW-DEOSSOPVSA-N 0.000 claims description 4
• KDSMEECDTHDWGG-DEOSSOPVSA-N 3-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=C(C#N)C=CC=1)C KDSMEECDTHDWGG-DEOSSOPVSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• XJMDLRTXSMXOFG-DEOSSOPVSA-N 5-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-2,3-difluorobenzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=C(C(=C(C#N)C=1)F)F)C XJMDLRTXSMXOFG-DEOSSOPVSA-N 0.000 claims description 4
• MZSPVPPUDSYEAS-DEOSSOPVSA-N 5-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=CC(=C(C#N)C=1)F)C MZSPVPPUDSYEAS-DEOSSOPVSA-N 0.000 claims description 4
• VAOZFQOCTNFQHL-UHFFFAOYSA-N 3-(aminomethyl)-1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-ol Chemical compound CC1=CC(=CC(F)=C1)C1=CN=CC(C2=NC3=C(F)C=C(F)C=C3N2)=C1N1CC(O)(CN)C1 VAOZFQOCTNFQHL-UHFFFAOYSA-N 0.000 claims description 3
• XDZAFOBGMPYENH-DEOSSOPVSA-N 3-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=C(C#N)C=C(C=1)F)C XDZAFOBGMPYENH-DEOSSOPVSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 125000002393 azetidinyl group Chemical group 0.000 claims description 3
• 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 description 2
• 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 description 2
• ZRWJINGOSDMPKT-INIZCTEOSA-N (3S)-1-[3-(2,3-dihydro-1-benzofuran-6-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound O1CCC2=C1C=C(C=C2)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=NC2=C(N1)C=CC=C2F ZRWJINGOSDMPKT-INIZCTEOSA-N 0.000 claims description 2
• ASVQHYVFKTVREJ-QHCPKHFHSA-N (3S)-1-[3-(3,4-difluorophenyl)-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound FC=1C=C(C=CC=1F)C=1C=NC=C(C=1N1C[C@](CC1)(N)C)C=1NC=2C(=NC=CC=2C)N=1 ASVQHYVFKTVREJ-QHCPKHFHSA-N 0.000 claims description 2
• 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 description 2
• RTTADQAOONRVQZ-QHCPKHFHSA-N (3S)-1-[3-(3-chloro-4-fluorophenyl)-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound Cc1ccnc2nc([nH]c12)-c1cncc(-c2ccc(F)c(Cl)c2)c1N1CC[C@](C)(N)C1 RTTADQAOONRVQZ-QHCPKHFHSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• GCOSJNLMUMEYJG-QHCPKHFHSA-N (3S)-1-[3-(3-chlorophenyl)-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound ClC=1C=C(C=CC=1)C=1C=NC=C(C=1N1C[C@](CC1)(N)C)C=1NC=2C(=NC=CC=2C)N=1 GCOSJNLMUMEYJG-QHCPKHFHSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• NYTSLAWGXLBROS-HNNXBMFYSA-N (3S)-1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-methylsulfonylphenyl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound CS(=O)(=O)C1=CC=CC(=C1)C1=CN=CC(C2=NC3=C(F)C=C(F)C=C3N2)=C1N1CC[C@H](N)C1 NYTSLAWGXLBROS-HNNXBMFYSA-N 0.000 claims description 2
• 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 description 2
• JICIJPWGXWQZJA-QHCPKHFHSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(2-methoxypyridin-4-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound COC1=NC=CC(=C1)C1=C(N2CC[C@](C)(N)C2)C(=CN=C1)C1=NC2=C(F)C=CC=C2N1 JICIJPWGXWQZJA-QHCPKHFHSA-N 0.000 claims description 2
• DITLMVSYWIQSLG-QHCPKHFHSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(2-methylpyridin-4-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1=NC=CC(=C1)C1=C(N2CC[C@](C)(N)C2)C(=CN=C1)C1=NC2=C(F)C=CC=C2N1 DITLMVSYWIQSLG-QHCPKHFHSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• XYIQEKIEWDBGHZ-QFIPXVFZSA-N (3S)-1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-[2-(trifluoromethyl)pyridin-4-yl]pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound C[C@]1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC(=NC=C1)C(F)(F)F XYIQEKIEWDBGHZ-QFIPXVFZSA-N 0.000 claims description 2
• 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 description 2
• MQXKRQGNIIQKTM-DEOSSOPVSA-N (3S)-1-[3-(4-fluoro-3-methoxyphenyl)-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound FC1=C(C=C(C=C1)C=1C=NC=C(C=1N1C[C@](CC1)(N)C)C=1NC=2C(=NC=CC=2C)N=1)OC MQXKRQGNIIQKTM-DEOSSOPVSA-N 0.000 claims description 2
• BDUHSMSURXCYII-DEOSSOPVSA-N (3S)-1-[3-(4-fluoro-3-methylphenyl)-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound FC1=C(C=C(C=C1)C=1C=NC=C(C=1N1C[C@](CC1)(N)C)C=1NC=2C(=NC=CC=2C)N=1)C BDUHSMSURXCYII-DEOSSOPVSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• RLYGXRDXKJSDMW-HNNXBMFYSA-N (3S)-1-[3-[4-fluoro-3-(trifluoromethoxy)phenyl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-4-yl]pyrrolidin-3-amine Chemical compound FC1=C(C=C(C=C1)C=1C=NC=C(C=1N1C[C@H](CC1)N)C1=NC2=C(N1)C=CC=C2C)OC(F)(F)F RLYGXRDXKJSDMW-HNNXBMFYSA-N 0.000 claims description 2
• FBZHJPGLGZRASV-QHCPKHFHSA-N (3S)-1-[3-[4-fluoro-3-(trifluoromethyl)phenyl]-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound FC1=C(C=C(C=C1)C=1C=NC=C(C=1N1C[C@](CC1)(N)C)C=1NC=2C(=NC=CC=2C)N=1)C(F)(F)F FBZHJPGLGZRASV-QHCPKHFHSA-N 0.000 claims description 2
• MUQGUHLVQZVQMY-UHFFFAOYSA-N 1-[1-[3-(2-chloro-3-fluorophenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]ethanamine Chemical compound CC(N)C1CN(C1)c1c(cncc1-c1cccc(F)c1Cl)-c1nc2c(F)cc(F)cc2[nH]1 MUQGUHLVQZVQMY-UHFFFAOYSA-N 0.000 claims description 2
• JTJOZVZAPCRMGR-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(2-fluoro-3-methylphenyl)pyridin-4-yl]azetidin-3-yl]ethanamine Chemical compound CC(N)C1CN(C1)c1c(cncc1-c1cccc(C)c1F)-c1nc2c(F)cc(F)cc2[nH]1 JTJOZVZAPCRMGR-UHFFFAOYSA-N 0.000 claims description 2
• KZAADSNTLDOVGS-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-2-methoxyphenyl)pyridin-4-yl]azetidin-3-yl]ethanamine Chemical compound COc1c(F)cccc1-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(C1)C(C)N KZAADSNTLDOVGS-UHFFFAOYSA-N 0.000 claims description 2
• WLBDJPJCSSJKNW-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(4-ethoxy-3-fluorophenyl)pyridin-4-yl]azetidin-3-yl]ethanamine Chemical compound CCOc1ccc(cc1F)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(C1)C(C)N WLBDJPJCSSJKNW-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• COEGUULEHWGDDW-UHFFFAOYSA-N 1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(1H-indol-5-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=CC=C2NC=CC2=C1)C1=NC2=C(F)C=CC=C2N1 COEGUULEHWGDDW-UHFFFAOYSA-N 0.000 claims description 2
• IGYZSZMWXKOZCD-UHFFFAOYSA-N 1-[3-(4-fluoro-1H-benzimidazol-2-yl)-5-(1H-indol-6-yl)pyridin-4-yl]-3-methylpyrrolidin-3-amine Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=CC=C2C=CNC2=C1)C1=NC2=C(F)C=CC=C2N1 IGYZSZMWXKOZCD-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• WTJVOFKFOSOJQW-VWLOTQADSA-N 2-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(3-cyano-4-methoxyphenyl)pyridin-3-yl]-1H-imidazo[4,5-b]pyridine-7-carbonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=CC(=C(C=C1)OC)C#N)C=1NC=2C(=NC=CC=2C#N)N=1)C WTJVOFKFOSOJQW-VWLOTQADSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• 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 description 2
• PMSOMRFBAIJDBB-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzamide Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2C)C=1C=C(C(=O)N)C=C(C=1)F)C PMSOMRFBAIJDBB-UHFFFAOYSA-N 0.000 claims description 2
• XDZAFOBGMPYENH-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=C(C#N)C=C(C=1)F)C XDZAFOBGMPYENH-UHFFFAOYSA-N 0.000 claims description 2
• KDSMEECDTHDWGG-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]benzonitrile Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=C(C#N)C=CC=1)C KDSMEECDTHDWGG-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• VKTYDNKQGVXSIF-VWLOTQADSA-N 3-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(4-fluoro-1-methylbenzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1C)C=CC=C2F)C=1C=C(C#N)C=CC=1)C VKTYDNKQGVXSIF-VWLOTQADSA-N 0.000 claims description 2
• 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 description 2
• LSHSMWTWLILNCX-VWLOTQADSA-N 3-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(5,7-dimethyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]benzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC(=CC=2C)C)N=1)C=1C=C(C#N)C=CC=1)C LSHSMWTWLILNCX-VWLOTQADSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• YASMXHVIZIUATD-AWEZNQCLSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4,7-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzamide Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC(F)=C2N1)C1=CC=CC(=C1)C(N)=O YASMXHVIZIUATD-AWEZNQCLSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• ANZSJKDFFOVAOI-AWEZNQCLSA-N 3-[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=CC(C#N)=C1F ANZSJKDFFOVAOI-AWEZNQCLSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• WFXJPWPOOREJHM-HNNXBMFYSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzamide Chemical compound N[C@H]1CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=CC(=C1)C(N)=O WFXJPWPOOREJHM-HNNXBMFYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• CGUSPROGINMGQO-KRWDZBQOSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]benzamide Chemical compound CC1=C2N=C(NC2=CC=C1)C1=CN=CC(C2=CC=CC(=C2)C(N)=O)=C1N1CC[C@H](N)C1 CGUSPROGINMGQO-KRWDZBQOSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• MQPPLTGILGUVOD-UHFFFAOYSA-N 3-[4-[3-amino-3-(trifluoromethyl)pyrrolidin-1-yl]-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzamide Chemical compound NC1(CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1)C=CC=C2F)C=1C=C(C(=O)N)C=CC=1)C(F)(F)F MQPPLTGILGUVOD-UHFFFAOYSA-N 0.000 claims description 2
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• 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 description 2
• 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 description 2
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• 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 description 2
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• 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 description 2
• 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 description 2
• SUAQJKUTTALWDJ-DEOSSOPVSA-N 4-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(5-fluoro-4-methyl-1H-benzimidazol-2-yl)pyridin-3-yl]pyridine-2-carbonitrile Chemical compound CC1=C2N=C(NC2=CC=C1F)C1=CN=CC(C2=CC(=NC=C2)C#N)=C1N1CC[C@](C)(N)C1 SUAQJKUTTALWDJ-DEOSSOPVSA-N 0.000 claims description 2
• 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 description 2
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• 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 description 2
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• HOYANWAMZNULAM-QHCPKHFHSA-N 5-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(6-fluoro-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=C(C=2)F)N=1)C=1C=CC(=C(C#N)C=1)F)C HOYANWAMZNULAM-QHCPKHFHSA-N 0.000 claims description 2
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• VIDMKTKRANGWJF-DEOSSOPVSA-N 5-[4-[(3S)-3-amino-3-methylpyrrolidin-1-yl]-5-(7-methoxy-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@@]1(CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2OC)N=1)C=1C=CC(=C(C#N)C=1)F)C VIDMKTKRANGWJF-DEOSSOPVSA-N 0.000 claims description 2
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• ZQFKTFRUSVCNET-INIZCTEOSA-N 5-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-(7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl]-2-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C=1NC=2C(=NC=CC=2C)N=1)C=1C=CC(=C(C#N)C=1)F ZQFKTFRUSVCNET-INIZCTEOSA-N 0.000 claims description 2
• 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 description 2
• DDGQKGXPYXQOQH-UHFFFAOYSA-N [1-[3-(3,5-dichlorophenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cc(Cl)cc(Cl)c1)-c1nc2c(F)cc(F)cc2[nH]1 DDGQKGXPYXQOQH-UHFFFAOYSA-N 0.000 claims description 2
• KUYKYNLBOTYHIY-UHFFFAOYSA-N [1-[3-(3-chlorophenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cccc(Cl)c1)-c1nc2c(F)cc(F)cc2[nH]1 KUYKYNLBOTYHIY-UHFFFAOYSA-N 0.000 claims description 2
• WFQBSEQNAOTTMX-UHFFFAOYSA-N [1-[3-(3-fluoro-5-methylphenyl)-5-(1H-imidazo[4,5-b]pyridin-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2nc3ncccc3[nH]2)c1N1CC(CN)C1 WFQBSEQNAOTTMX-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• XIQSAEJPPOSVNR-UHFFFAOYSA-N [1-[3-(3-fluoro-5-methylphenyl)-5-(3H-imidazo[4,5-c]pyridin-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2nc3ccncc3[nH]2)c1N1CC(CN)C1 XIQSAEJPPOSVNR-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• JBXHEXGJIJFMFX-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(1H-indol-6-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1ccc2cc[nH]c2c1)-c1nc2c(F)cc(F)cc2[nH]1 JBXHEXGJIJFMFX-UHFFFAOYSA-N 0.000 claims description 2
• SJTJVRPSGXTUFA-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(1H-indol-7-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cccc2cc[nH]c12)-c1nc2c(F)cc(F)cc2[nH]1 SJTJVRPSGXTUFA-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• CXVSXCPTDQIMSS-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(2-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1ccccc1-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 CXVSXCPTDQIMSS-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• NTUKIROIQXTDQV-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound Cc1cc(F)cc(c1)-c1cncc(-c2nc3c(F)cc(F)cc3[nH]2)c1N1CC(CN)C1 NTUKIROIQXTDQV-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• VZECRMITRVHNBW-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-naphthalen-1-ylpyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1cccc2ccccc12)-c1nc2c(F)cc(F)cc2[nH]1 VZECRMITRVHNBW-UHFFFAOYSA-N 0.000 claims description 2
• ONRCOUGZANSXJI-UHFFFAOYSA-N [1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-naphthalen-2-ylpyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)c1c(cncc1-c1ccc2ccccc2c1)-c1nc2c(F)cc(F)cc2[nH]1 ONRCOUGZANSXJI-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• CSPMIINAUJZPCE-UHFFFAOYSA-N [1-[3-[3-chloro-5-(trifluoromethyl)phenyl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]methanamine Chemical compound NCC1CN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=CC(Cl)=CC(=C1)C(F)(F)F CSPMIINAUJZPCE-UHFFFAOYSA-N 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• PNLJXCYHPZAREL-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-[3-fluoro-5-(trifluoromethyl)phenyl]pyridin-4-yl]azetidin-3-yl]ethanamine Chemical compound CC(N)C1CN(C1)c1c(cncc1-c1cc(F)cc(c1)C(F)(F)F)-c1nc2c(F)cc(F)cc2[nH]1 PNLJXCYHPZAREL-UHFFFAOYSA-N 0.000 claims 2
• JNNMLMQTWIYXOB-UHFFFAOYSA-N 1-[1-[3-(3-chloro-5-fluorophenyl)-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-4-yl]azetidin-3-yl]ethanamine Chemical compound CC(N)C1CN(C1)c1c(cncc1-c1cc(F)cc(Cl)c1)-c1nc2c(F)cc(F)cc2[nH]1 JNNMLMQTWIYXOB-UHFFFAOYSA-N 0.000 claims 1
• HHKAJFXRJFJXMO-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]ethanamine Chemical compound CC(N)C1CN(C1)c1c(cncc1-c1cc(C)cc(F)c1)-c1nc2c(F)cc(F)cc2[nH]1 HHKAJFXRJFJXMO-UHFFFAOYSA-N 0.000 claims 1
• GFWQXCCHNPVHSL-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)pyridin-4-yl]azetidin-3-yl]propan-1-amine Chemical compound C=1(C=NC=C(C=1N1CC(C(CC)N)C1)C1=CC(C)=CC(F)=C1)C=1NC2=C(C=C(F)C=C2N=1)F GFWQXCCHNPVHSL-UHFFFAOYSA-N 0.000 claims 1
• XMBFQDPNXMGESQ-UHFFFAOYSA-N 1-[1-[3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluorophenyl)pyridin-4-yl]-3-methylazetidin-3-yl]ethanamine Chemical compound CC(N)C1(C)CN(C1)c1c(cncc1-c1cccc(F)c1)-c1nc2c(F)cc(F)cc2[nH]1 XMBFQDPNXMGESQ-UHFFFAOYSA-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
• 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
• IKRAKDBGIZBWAV-UHFFFAOYSA-N 2-[4-[3-(1-aminoethyl)azetidin-1-yl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-6-fluorophenol Chemical compound CC(N)C1CN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=C(O)C(F)=CC=C1 IKRAKDBGIZBWAV-UHFFFAOYSA-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
• VJBNWZHKKJUDJZ-UHFFFAOYSA-N 3-[4-(3-amino-3-methylpyrrolidin-1-yl)-5-(4-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzamide Chemical compound CC1(N)CCN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=CC=C2N1)C1=CC=CC(=C1)C(N)=O VJBNWZHKKJUDJZ-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
• 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
• 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
• 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
• COOBKTYTXIKLFX-FQEVSTJZSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]-5-[1-(2-methoxyethyl)benzimidazol-2-yl]pyridin-3-yl]-5-fluorobenzonitrile Chemical compound N[C@@H]1CN(CC1)C1=C(C=NC=C1C1=NC2=C(N1CCOC)C=CC=C2)C=1C=C(C#N)C=C(C=1)F COOBKTYTXIKLFX-FQEVSTJZSA-N 0.000 claims 1
• FUEVUELKEHKJCS-UHFFFAOYSA-N 3-[4-[3-(1-aminoethyl)-3-methylazetidin-1-yl]-5-(4,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]benzonitrile Chemical compound CC(N)C1(C)CN(C1)C1=C(C=NC=C1C1=NC2=C(F)C=C(F)C=C2N1)C1=CC=CC(=C1)C#N FUEVUELKEHKJCS-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
• 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
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