JP2013526536A5

JP2013526536A5 -

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Publication number: JP2013526536A5
Authority: JP; Japan
Prior art keywords: azetidin; pyrazin; quinoline; quinolin; methanone
Prior art date: 2011-05-11
Legal status : Granted

Application number

JP2013510285A

Other languages

English (en)

Japanese (ja)

Other versions

JP5702855B2 (ja

JP2013526536A (ja

Filing date

2011-05-11

Publication date

2014-04-03

2011-05-11 Application filed filed Critical

2011-05-11 Priority claimed from PCT/US2011/036148 external-priority patent/WO2011143365A1/en

2013-06-24 Publication of JP2013526536A publication Critical patent/JP2013526536A/ja

2014-04-03 Publication of JP2013526536A5 publication Critical patent/JP2013526536A5/ja

2015-04-15 Application granted granted Critical

2015-04-15 Publication of JP5702855B2 publication Critical patent/JP5702855B2/ja

Status Expired - Fee Related legal-status Critical Current

2031-05-11 Anticipated expiration legal-status Critical

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-1 3,5-dimethoxyphenyl Chemical group 0.000 claims 30
229920006395 saturated elastomer Polymers 0.000 claims 24
150000003839 salts Chemical class 0.000 claims 23
150000001875 compounds Chemical class 0.000 claims 22
125000005843 halogen group Chemical group 0.000 claims 14
229910052757 nitrogen Inorganic materials 0.000 claims 14
229910052799 carbon Inorganic materials 0.000 claims 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
125000004433 nitrogen atom Chemical group N* 0.000 claims 7
ILEVFKKYXSPPJM-UHFFFAOYSA-N N1=CC(=CC=C1)C1CN(CC1)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1 Chemical compound N1=CC(=CC=C1)C1CN(CC1)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1 ILEVFKKYXSPPJM-UHFFFAOYSA-N 0.000 claims 6
229910052760 oxygen Inorganic materials 0.000 claims 5
239000008194 pharmaceutical composition Substances 0.000 claims 5
125000004429 atom Chemical group 0.000 claims 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
125000002950 monocyclic group Chemical group 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
125000001424 substituent group Chemical group 0.000 claims 4
229910052717 sulfur Inorganic materials 0.000 claims 4
KNNGPXFAAJXFLG-MRXNPFEDSA-N (1r)-1-[1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidin-4-yl]ethanol Chemical compound C1CC([C@H](O)C)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 KNNGPXFAAJXFLG-MRXNPFEDSA-N 0.000 claims 3
KNNGPXFAAJXFLG-INIZCTEOSA-N (1s)-1-[1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidin-4-yl]ethanol Chemical compound C1CC([C@@H](O)C)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 KNNGPXFAAJXFLG-INIZCTEOSA-N 0.000 claims 3
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 3
UAOTZYBGYKZIDA-OAHLLOKOSA-N 2-[3-[3-[(3r)-3-methylpyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1[C@H](C)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 UAOTZYBGYKZIDA-OAHLLOKOSA-N 0.000 claims 3
UAOTZYBGYKZIDA-HNNXBMFYSA-N 2-[3-[3-[(3s)-3-methylpyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1[C@@H](C)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 UAOTZYBGYKZIDA-HNNXBMFYSA-N 0.000 claims 3
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 3
201000010099 disease Diseases 0.000 claims 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
229910052739 hydrogen Inorganic materials 0.000 claims 3
239000003112 inhibitor Substances 0.000 claims 3
125000004430 oxygen atom Chemical group O* 0.000 claims 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
VMAQNBRTXIKONU-GOSISDBHSA-N (3r)-n,n-dimethyl-1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]pyrrolidin-3-amine Chemical compound C1[C@H](N(C)C)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 VMAQNBRTXIKONU-GOSISDBHSA-N 0.000 claims 2
FANSKEAEHOCFPM-UHFFFAOYSA-N (6-methyl-1h-benzimidazol-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N1C2=CC(C)=CC=C2N=C1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 FANSKEAEHOCFPM-UHFFFAOYSA-N 0.000 claims 2
YRPFGKXIWYXGHT-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 YRPFGKXIWYXGHT-UHFFFAOYSA-N 0.000 claims 2
ZFTJTNWIESVCOY-UHFFFAOYSA-N 2-[3-[3-(6-methoxypyridin-2-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=N1 ZFTJTNWIESVCOY-UHFFFAOYSA-N 0.000 claims 2
DOKPMAHKOKXQTR-UHFFFAOYSA-N 3-[3-[3-[3-fluoro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound FC=1C=C(C=C(C1)C(F)(F)F)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1 DOKPMAHKOKXQTR-UHFFFAOYSA-N 0.000 claims 2
NWSXHIAJISVPGL-UHFFFAOYSA-N 4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 NWSXHIAJISVPGL-UHFFFAOYSA-N 0.000 claims 2
206010012289 Dementia Diseases 0.000 claims 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
MOUYLPZSTHOZLB-UHFFFAOYSA-N N1=CC=C(C=C1)C1CN(CC1)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1 Chemical compound N1=CC=C(C=C1)C1CN(CC1)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1 MOUYLPZSTHOZLB-UHFFFAOYSA-N 0.000 claims 2
125000002619 bicyclic group Chemical group 0.000 claims 2
210000001159 caudate nucleus Anatomy 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
125000000623 heterocyclic group Chemical group 0.000 claims 2
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
230000001898 pallidal effect Effects 0.000 claims 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
125000004434 sulfur atom Chemical group 0.000 claims 2
WRLYTXMJKNQQQM-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 WRLYTXMJKNQQQM-UHFFFAOYSA-N 0.000 claims 1
FFBFPQPAOHWXKA-IAGOWNOFSA-N (1r,4r)-5-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]-2-oxa-5-azabicyclo[2.2.1]heptane Chemical class C1=CC=CC2=NC(N3CC(C3)C3=NC=CN=C3N3C[C@@]4(OC[C@@]3([H])C4)[H])=CC=C21 FFBFPQPAOHWXKA-IAGOWNOFSA-N 0.000 claims 1
LKBICRSWFRXGRG-UHFFFAOYSA-N (3-methylpyridin-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound CC1=CC=CN=C1C(=O)N1CC(C=2C(=NC=CN=2)C=2C=CC=CC=2)C1 LKBICRSWFRXGRG-UHFFFAOYSA-N 0.000 claims 1
NGEXGWCJQROFAS-CQSZACIVSA-N (3s)-1-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]piperidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCC[C@H](C#N)C1 NGEXGWCJQROFAS-CQSZACIVSA-N 0.000 claims 1
JGXKLWJTYYOZHY-IRXDYDNUSA-N (3s,4s)-1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]pyrrolidine-3,4-diol Chemical compound C1[C@H](O)[C@@H](O)CN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 JGXKLWJTYYOZHY-IRXDYDNUSA-N 0.000 claims 1
OLVXUJLAMOMDMQ-UHFFFAOYSA-N (4-chloro-1h-benzimidazol-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N1C=2C(Cl)=CC=CC=2N=C1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 OLVXUJLAMOMDMQ-UHFFFAOYSA-N 0.000 claims 1
YRTJUFPNLVAYMT-UHFFFAOYSA-N (4-chloro-1h-benzimidazol-2-yl)-[3-(3-pyridin-3-ylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N1C=2C(Cl)=CC=CC=2N=C1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CN=C1 YRTJUFPNLVAYMT-UHFFFAOYSA-N 0.000 claims 1
UKICQWVRXIZJEC-UHFFFAOYSA-N (4-fluoro-1h-benzimidazol-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N1C=2C(F)=CC=CC=2N=C1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 UKICQWVRXIZJEC-UHFFFAOYSA-N 0.000 claims 1
FGYHRPKUULUUEV-UHFFFAOYSA-N (4-methylpyridin-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound CC1=CC=NC(C(=O)N2CC(C2)C=2C(=NC=CN=2)C=2C=CC=CC=2)=C1 FGYHRPKUULUUEV-UHFFFAOYSA-N 0.000 claims 1
YUZYNQHNLFAOQH-UHFFFAOYSA-N (5-methylpyridin-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N1=CC(C)=CC=C1C(=O)N1CC(C=2C(=NC=CN=2)C=2C=CC=CC=2)C1 YUZYNQHNLFAOQH-UHFFFAOYSA-N 0.000 claims 1
AIGNMUVMERTZNP-UHFFFAOYSA-N (6-fluoro-1h-benzimidazol-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N1C2=CC(F)=CC=C2N=C1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 AIGNMUVMERTZNP-UHFFFAOYSA-N 0.000 claims 1
SDSUHCSHJNZBHQ-UHFFFAOYSA-N (6-methylpyridin-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound CC1=CC=CC(C(=O)N2CC(C2)C=2C(=NC=CN=2)C=2C=CC=CC=2)=N1 SDSUHCSHJNZBHQ-UHFFFAOYSA-N 0.000 claims 1
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
ZANCFGZXXVTYDU-UHFFFAOYSA-N 1,3-benzothiazol-2-yl-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2SC=1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 ZANCFGZXXVTYDU-UHFFFAOYSA-N 0.000 claims 1
OJCUGSPXFCNMDX-UHFFFAOYSA-N 1-[1-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]piperidin-4-yl]ethanone Chemical compound C1CC(C(=O)C)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 OJCUGSPXFCNMDX-UHFFFAOYSA-N 0.000 claims 1
CJIHPPUKJDERJH-UHFFFAOYSA-N 1-[3-(1-quinazolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound C1CC(C#N)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CN=2)C1 CJIHPPUKJDERJH-UHFFFAOYSA-N 0.000 claims 1
KRRSZDTXOOOKQA-UHFFFAOYSA-N 1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 KRRSZDTXOOOKQA-UHFFFAOYSA-N 0.000 claims 1
HEQACRRBIKQELW-UHFFFAOYSA-N 1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound C1CC(C#N)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 HEQACRRBIKQELW-UHFFFAOYSA-N 0.000 claims 1
RDISXHYFVLOZDN-UHFFFAOYSA-N 1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 RDISXHYFVLOZDN-UHFFFAOYSA-N 0.000 claims 1
QMBMJKIHULOECZ-UHFFFAOYSA-N 1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]pyrrolidin-3-amine Chemical compound C1C(N)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 QMBMJKIHULOECZ-UHFFFAOYSA-N 0.000 claims 1
WBGUTSYAZIDDNF-UHFFFAOYSA-N 1-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]phthalazine Chemical compound C1N(C=2C3=CC=CC=C3C=NN=2)CC1C1=NC=CN=C1C1=CC=CC=C1 WBGUTSYAZIDDNF-UHFFFAOYSA-N 0.000 claims 1
ZIIMJJQAYKUFHI-UHFFFAOYSA-N 1-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 ZIIMJJQAYKUFHI-UHFFFAOYSA-N 0.000 claims 1
SELAZMJMGDIXTM-UHFFFAOYSA-N 1-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 SELAZMJMGDIXTM-UHFFFAOYSA-N 0.000 claims 1
PDJMVGZDJWUKSL-UHFFFAOYSA-N 1-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]piperidin-4-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCC(=O)CC1 PDJMVGZDJWUKSL-UHFFFAOYSA-N 0.000 claims 1
DQRKILNWIGHEJF-UHFFFAOYSA-N 1-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCC(C#N)CC1 DQRKILNWIGHEJF-UHFFFAOYSA-N 0.000 claims 1
QWOIJNIWMLBKOU-UHFFFAOYSA-N 1-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 QWOIJNIWMLBKOU-UHFFFAOYSA-N 0.000 claims 1
CGVZSOXCSGJLOR-UHFFFAOYSA-N 1-[3-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 CGVZSOXCSGJLOR-UHFFFAOYSA-N 0.000 claims 1
RMSDWQMVCSUUKK-UHFFFAOYSA-N 1-[4-[3-(1-quinazolin-2-ylazetidin-3-yl)pyrazin-2-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CN=2)C1 RMSDWQMVCSUUKK-UHFFFAOYSA-N 0.000 claims 1
UWCUJTUJHFUPII-UHFFFAOYSA-N 1-[4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 UWCUJTUJHFUPII-UHFFFAOYSA-N 0.000 claims 1
RUZUHHNQTOKDHR-UHFFFAOYSA-N 1-[4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 RUZUHHNQTOKDHR-UHFFFAOYSA-N 0.000 claims 1
CDKPAVJAGKPFHR-UHFFFAOYSA-N 1-[4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 CDKPAVJAGKPFHR-UHFFFAOYSA-N 0.000 claims 1
SAAZEBWRCGYUFF-UHFFFAOYSA-N 1-[4-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]-1,4-diazepan-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 SAAZEBWRCGYUFF-UHFFFAOYSA-N 0.000 claims 1
HAXSANXTLSCHFK-UHFFFAOYSA-N 1-[4-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 HAXSANXTLSCHFK-UHFFFAOYSA-N 0.000 claims 1
TXESTSBBFYCPDX-UHFFFAOYSA-N 1-[4-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 TXESTSBBFYCPDX-UHFFFAOYSA-N 0.000 claims 1
KZGXQZYSPXZAIO-UHFFFAOYSA-N 1-[4-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 KZGXQZYSPXZAIO-UHFFFAOYSA-N 0.000 claims 1
OVBGBOJSSVDOSL-UHFFFAOYSA-N 1-methyl-4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 OVBGBOJSSVDOSL-UHFFFAOYSA-N 0.000 claims 1
UUKUTKFFHFFXLI-UHFFFAOYSA-N 1-methyl-5-[3-(1-quinazolin-2-ylazetidin-3-yl)pyrazin-2-yl]-3h-indol-2-one Chemical compound C1=CC=CC2=NC(N3CC(C3)C3=NC=CN=C3C=3C=C4CC(=O)N(C4=CC=3)C)=NC=C21 UUKUTKFFHFFXLI-UHFFFAOYSA-N 0.000 claims 1
UGGBOTIKGAFYDS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(2-phenylpyridin-3-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=CC=CN=C1C1=CC=CC=C1 UGGBOTIKGAFYDS-UHFFFAOYSA-N 0.000 claims 1
GWHFLYSMGBIISV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-morpholin-4-ylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCOCC1 GWHFLYSMGBIISV-UHFFFAOYSA-N 0.000 claims 1
YSUKVDCQEFVDLG-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-phenoxypyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1OC1=CC=CC=C1 YSUKVDCQEFVDLG-UHFFFAOYSA-N 0.000 claims 1
GUCPCLZTZMRAFR-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 GUCPCLZTZMRAFR-UHFFFAOYSA-N 0.000 claims 1
IRDYXJLMBIXWOA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-phenylpyridin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CC=C1C1=CC=CC=C1 IRDYXJLMBIXWOA-UHFFFAOYSA-N 0.000 claims 1
YFTBVPDYMNBQSB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-phenylquinolin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YFTBVPDYMNBQSB-UHFFFAOYSA-N 0.000 claims 1
MUURWGXPOFSTBH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-phenylquinoxalin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 MUURWGXPOFSTBH-UHFFFAOYSA-N 0.000 claims 1
CTEJNTPNKSPWKX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-piperidin-1-ylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCCCC1 CTEJNTPNKSPWKX-UHFFFAOYSA-N 0.000 claims 1
VRBOVMQPSVFTBK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-piperidin-1-ylquinoxalin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC2=CC=CC=C2N=C1N1CCCCC1 VRBOVMQPSVFTBK-UHFFFAOYSA-N 0.000 claims 1
NFZXEOCZRFLMNJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-pyridin-4-ylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=NC=C1 NFZXEOCZRFLMNJ-UHFFFAOYSA-N 0.000 claims 1
WIGCMCSGKOKBHB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(3-pyrrolidin-1-ylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCCC1 WIGCMCSGKOKBHB-UHFFFAOYSA-N 0.000 claims 1
CFVRKVUSYXYJIL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(5-fluoro-3-phenylpyridin-2-yl)azetidin-1-yl]methanone Chemical compound C=1C(F)=CN=C(C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)C=1C1=CC=CC=C1 CFVRKVUSYXYJIL-UHFFFAOYSA-N 0.000 claims 1
LVBXDLMVTGJZQT-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-(5-phenylpyrimidin-4-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=NC=C1C1=CC=CC=C1 LVBXDLMVTGJZQT-UHFFFAOYSA-N 0.000 claims 1
BCAMKFFSJBRIGJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(1,3-dihydroisoindol-2-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=CC=C2NC(C(N3CC(C3)C=3C(=NC=CN=3)N3CC4=CC=CC=C4C3)=O)=NC2=C1 BCAMKFFSJBRIGJ-UHFFFAOYSA-N 0.000 claims 1
BWIVKTVFLKTESZ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(1,4-oxazepan-4-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCCOCC1 BWIVKTVFLKTESZ-UHFFFAOYSA-N 0.000 claims 1
KCOXTURSOJZMBU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(1-methylpyrazol-4-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=NN(C)C=C1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 KCOXTURSOJZMBU-UHFFFAOYSA-N 0.000 claims 1
ZLNLDZAWBKOTTM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(2-methoxyphenoxy)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound COC1=CC=CC=C1OC1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 ZLNLDZAWBKOTTM-UHFFFAOYSA-N 0.000 claims 1
MXEMCLZPFFMEFF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(2-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound COC1=CC=CC=C1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 MXEMCLZPFFMEFF-UHFFFAOYSA-N 0.000 claims 1
DFYOXIFTOCWUFF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 DFYOXIFTOCWUFF-UHFFFAOYSA-N 0.000 claims 1
CQILVSBAOJYERG-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 CQILVSBAOJYERG-UHFFFAOYSA-N 0.000 claims 1
KFFRZXSCEHZCKP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3,4-dihydro-1h-isoquinolin-2-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=CC=C2NC(C(N3CC(C3)C=3C(=NC=CN=3)N3CC4=CC=CC=C4CC3)=O)=NC2=C1 KFFRZXSCEHZCKP-UHFFFAOYSA-N 0.000 claims 1
WLKXMKWDIVUDJQ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3,4-dimethoxyphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 WLKXMKWDIVUDJQ-UHFFFAOYSA-N 0.000 claims 1
QXFKXNZFCFJICL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-ethoxyphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound CCOC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QXFKXNZFCFJICL-UHFFFAOYSA-N 0.000 claims 1
YJMWZWQWBHEEEJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-fluoro-5-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound COC1=CC(F)=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 YJMWZWQWBHEEEJ-UHFFFAOYSA-N 0.000 claims 1
GEBVQMVZKPDQGX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-fluoro-5-methylphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound CC1=CC(F)=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 GEBVQMVZKPDQGX-UHFFFAOYSA-N 0.000 claims 1
DRTCCKGPGLUQMX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-hydroxypiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1C(O)CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 DRTCCKGPGLUQMX-UHFFFAOYSA-N 0.000 claims 1
QCVUWFLYRDGXBC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-methoxyphenoxy)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound COC1=CC=CC(OC=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QCVUWFLYRDGXBC-UHFFFAOYSA-N 0.000 claims 1
GHPSROQRQLDECX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 GHPSROQRQLDECX-UHFFFAOYSA-N 0.000 claims 1
MECJGKXQCSYWOS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound CC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 MECJGKXQCSYWOS-UHFFFAOYSA-N 0.000 claims 1
HSCDAWNZAILNKB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-methylpiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1C(C)CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 HSCDAWNZAILNKB-UHFFFAOYSA-N 0.000 claims 1
VLUONFPFPAASKP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-propan-2-yloxyphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound CC(C)OC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 VLUONFPFPAASKP-UHFFFAOYSA-N 0.000 claims 1
UDZVGFIJADGXMY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(3-propan-2-ylphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound CC(C)C1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 UDZVGFIJADGXMY-UHFFFAOYSA-N 0.000 claims 1
PKZGUAITGZXPOS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4,4-difluoropiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(F)(F)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 PKZGUAITGZXPOS-UHFFFAOYSA-N 0.000 claims 1
XHEDRPYQMYAOFX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4,4-dimethylpiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(C)(C)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 XHEDRPYQMYAOFX-UHFFFAOYSA-N 0.000 claims 1
OLDYBVGPRCUQHR-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-fluoro-3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=C(F)C(C)=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 OLDYBVGPRCUQHR-UHFFFAOYSA-N 0.000 claims 1
WPDOOHDODOYQOS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-hydroxy-4-methylpiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(C)(O)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 WPDOOHDODOYQOS-UHFFFAOYSA-N 0.000 claims 1
PBZMTMFIKFQKLI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-hydroxyazepan-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(O)CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 PBZMTMFIKFQKLI-UHFFFAOYSA-N 0.000 claims 1
BZAIZRCAMBRBLE-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-hydroxypiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(O)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 BZAIZRCAMBRBLE-UHFFFAOYSA-N 0.000 claims 1
MZPUHVVCBQJUMY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-hydroxypiperidin-1-yl)quinoxalin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(O)CCN1C1=NC2=CC=CC=C2N=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 MZPUHVVCBQJUMY-UHFFFAOYSA-N 0.000 claims 1
ASHJWBIMOKYLAZ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-methoxy-3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=C(C)C(OC)=CC=C1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 ASHJWBIMOKYLAZ-UHFFFAOYSA-N 0.000 claims 1
FVQGXEWJLKOHAX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-methoxyphenoxy)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1OC1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 FVQGXEWJLKOHAX-UHFFFAOYSA-N 0.000 claims 1
ZWOJHDCGAXERAD-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 ZWOJHDCGAXERAD-UHFFFAOYSA-N 0.000 claims 1
FLSONDPEMDBIPA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-methyl-1,4-diazepan-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CN(C)CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 FLSONDPEMDBIPA-UHFFFAOYSA-N 0.000 claims 1
NDFXMXBPYIXZAJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-methylpiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(C)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 NDFXMXBPYIXZAJ-UHFFFAOYSA-N 0.000 claims 1
SVUHTLVHOVGAQX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(4-methylthiophen-2-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound CC1=CSC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 SVUHTLVHOVGAQX-UHFFFAOYSA-N 0.000 claims 1
JEPSGYHOWQPRBL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(5-methoxypyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound COC1=CN=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 JEPSGYHOWQPRBL-UHFFFAOYSA-N 0.000 claims 1
ORTRUDBSDGMIIF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(5-methylpyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound CC1=CN=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 ORTRUDBSDGMIIF-UHFFFAOYSA-N 0.000 claims 1
BTXMSLGTIPJVDH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-(oxan-4-yl)pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1C1CCOCC1 BTXMSLGTIPJVDH-UHFFFAOYSA-N 0.000 claims 1
CMPSMIWNRNTFNH-CQSZACIVSA-N 1h-benzimidazol-2-yl-[3-[3-[(2r)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound OC[C@H]1CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 CMPSMIWNRNTFNH-CQSZACIVSA-N 0.000 claims 1
CMPSMIWNRNTFNH-AWEZNQCLSA-N 1h-benzimidazol-2-yl-[3-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound OC[C@@H]1CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 CMPSMIWNRNTFNH-AWEZNQCLSA-N 0.000 claims 1
DRTCCKGPGLUQMX-CQSZACIVSA-N 1h-benzimidazol-2-yl-[3-[3-[(3r)-3-hydroxypiperidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1[C@H](O)CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 DRTCCKGPGLUQMX-CQSZACIVSA-N 0.000 claims 1
SZQIATLHQGUNAU-CYBMUJFWSA-N 1h-benzimidazol-2-yl-[3-[3-[(3r)-3-hydroxypyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1[C@H](O)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 SZQIATLHQGUNAU-CYBMUJFWSA-N 0.000 claims 1
DRTCCKGPGLUQMX-AWEZNQCLSA-N 1h-benzimidazol-2-yl-[3-[3-[(3s)-3-hydroxypiperidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1[C@@H](O)CCCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 DRTCCKGPGLUQMX-AWEZNQCLSA-N 0.000 claims 1
SZQIATLHQGUNAU-ZDUSSCGKSA-N 1h-benzimidazol-2-yl-[3-[3-[(3s)-3-hydroxypyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1[C@@H](O)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 SZQIATLHQGUNAU-ZDUSSCGKSA-N 0.000 claims 1
KQBFMNYTQVRHSP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-[3-(hydroxymethyl)phenyl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound OCC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 KQBFMNYTQVRHSP-UHFFFAOYSA-N 0.000 claims 1
DDNUHKMHFIEDKA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-[3-(methoxymethyl)phenyl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound COCC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 DDNUHKMHFIEDKA-UHFFFAOYSA-N 0.000 claims 1
SIKKBWWIIMWRKB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-[3-(trifluoromethoxy)phenyl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 SIKKBWWIIMWRKB-UHFFFAOYSA-N 0.000 claims 1
VFZGFVQZGGUJGY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-[4-(2-hydroxyethyl)piperidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(CCO)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 VFZGFVQZGGUJGY-UHFFFAOYSA-N 0.000 claims 1
JZIWHMHRFMPJCN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-[4-(hydroxymethyl)piperidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(CO)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 JZIWHMHRFMPJCN-UHFFFAOYSA-N 0.000 claims 1
AAZNIMCVIKCNFF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-[4-(methoxymethyl)piperidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(COC)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 AAZNIMCVIKCNFF-UHFFFAOYSA-N 0.000 claims 1
BKCFHUCXNCQWSN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[3-[3-[4-(trifluoromethyl)piperidin-1-yl]pyrazin-2-yl]azetidin-1-yl]methanone Chemical compound C1CC(C(F)(F)F)CCN1C1=NC=CN=C1C1CN(C(=O)C=2NC3=CC=CC=C3N=2)C1 BKCFHUCXNCQWSN-UHFFFAOYSA-N 0.000 claims 1
PYLSMOIPCUHVRT-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-phenylpyrazin-2-yl)piperidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)N(CC1)CCC1C1=NC=CN=C1C1=CC=CC=C1 PYLSMOIPCUHVRT-UHFFFAOYSA-N 0.000 claims 1
AJCJTSNZKMXDFU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(hydroxymethyl)piperidin-1-yl]pyrazin-2-yl]piperidin-1-yl]methanone Chemical compound C1CC(CO)CCN1C1=NC=CN=C1C1CCN(C(=O)C=2NC3=CC=CC=C3N=2)CC1 AJCJTSNZKMXDFU-UHFFFAOYSA-N 0.000 claims 1
KGWASUNVSJTJCO-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2-[3-[3-[2-(trifluoromethyl)pyridin-3-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=NC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 KGWASUNVSJTJCO-UHFFFAOYSA-N 0.000 claims 1
GGHKWUZUBLOVIC-UHFFFAOYSA-N 2,2-dimethyl-4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]morpholine Chemical compound C1COC(C)(C)CN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 GGHKWUZUBLOVIC-UHFFFAOYSA-N 0.000 claims 1
125000004562 2,3-dihydroindol-1-yl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
OTIPQHSLAKSABC-UHFFFAOYSA-N 2-(3-methoxyphenyl)-3-(1-quinolin-2-ylazetidin-3-yl)quinoxaline Chemical compound COC1=CC=CC(C=2C(=NC3=CC=CC=C3N=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 OTIPQHSLAKSABC-UHFFFAOYSA-N 0.000 claims 1
RBXRDVZQVIFZTG-UHFFFAOYSA-N 2-(3-methoxyphenyl)-3-[1-(4-phenylpyrimidin-2-yl)azetidin-3-yl]pyrazine Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C(C=CN=2)C=2C=CC=CC=2)=C1 RBXRDVZQVIFZTG-UHFFFAOYSA-N 0.000 claims 1
GOJRPLUZGNVVAD-UHFFFAOYSA-N 2-(3-methylphenyl)-3-(1-quinolin-2-ylazetidin-3-yl)quinoxaline Chemical compound CC1=CC=CC(C=2C(=NC3=CC=CC=C3N=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 GOJRPLUZGNVVAD-UHFFFAOYSA-N 0.000 claims 1
ZAIXVMWZFBVYDU-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-3-(1-quinolin-2-ylazetidin-3-yl)quinoxaline Chemical compound C1CN(C=2C(=NC3=CC=CC=C3N=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)CCC1CC1=CC=CC=C1 ZAIXVMWZFBVYDU-UHFFFAOYSA-N 0.000 claims 1
IRGDAVOYDNDOFL-UHFFFAOYSA-N 2-[1-[3-(1-quinolin-2-ylazetidin-3-yl)pyridazin-4-yl]piperidin-4-yl]quinoline Chemical compound C1=CC=CC2=NC(C3CCN(CC3)C3=CC=NN=C3C3CN(C3)C=3N=C4C=CC=CC4=CC=3)=CC=C21 IRGDAVOYDNDOFL-UHFFFAOYSA-N 0.000 claims 1
OEGKMSNVNRVKJK-UHFFFAOYSA-N 2-[1-[3-[1-(5-bromopyridin-2-yl)azetidin-3-yl]pyrazin-2-yl]piperidin-4-yl]quinoline Chemical compound N1=CC(Br)=CC=C1N1CC(C=2C(=NC=CN=2)N2CCC(CC2)C=2N=C3C=CC=CC3=CC=2)C1 OEGKMSNVNRVKJK-UHFFFAOYSA-N 0.000 claims 1
HBRYICMCXJOZOK-UHFFFAOYSA-N 2-[1-[3-[1-(5-chloropyridin-2-yl)azetidin-3-yl]pyrazin-2-yl]piperidin-4-yl]quinoline Chemical compound N1=CC(Cl)=CC=C1N1CC(C=2C(=NC=CN=2)N2CCC(CC2)C=2N=C3C=CC=CC3=CC=2)C1 HBRYICMCXJOZOK-UHFFFAOYSA-N 0.000 claims 1
CITZWMIEPVLUEP-UHFFFAOYSA-N 2-[1-[3-[1-(5-methylpyridin-2-yl)azetidin-3-yl]pyrazin-2-yl]piperidin-4-yl]quinoline Chemical compound N1=CC(C)=CC=C1N1CC(C=2C(=NC=CN=2)N2CCC(CC2)C=2N=C3C=CC=CC3=CC=2)C1 CITZWMIEPVLUEP-UHFFFAOYSA-N 0.000 claims 1
OJXQZIOXLNPBFM-UHFFFAOYSA-N 2-[1-[3-[1-(6-methylpyridin-2-yl)azetidin-3-yl]pyrazin-2-yl]piperidin-4-yl]quinoline Chemical compound CC1=CC=CC(N2CC(C2)C=2C(=NC=CN=2)N2CCC(CC2)C=2N=C3C=CC=CC3=CC=2)=N1 OJXQZIOXLNPBFM-UHFFFAOYSA-N 0.000 claims 1
LOTIOUNCKIOAQV-UHFFFAOYSA-N 2-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]aniline Chemical compound NC1=CC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 LOTIOUNCKIOAQV-UHFFFAOYSA-N 0.000 claims 1
LZCGVOWZEUNQHQ-UHFFFAOYSA-N 2-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]phenol Chemical compound OC1=CC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 LZCGVOWZEUNQHQ-UHFFFAOYSA-N 0.000 claims 1
PIULQLKCJFQBOG-UHFFFAOYSA-N 2-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]-1h-benzimidazole Chemical compound C1N(C=2NC3=CC=CC=C3N=2)CC1C1=NC=CN=C1C1=CC=CC=C1 PIULQLKCJFQBOG-UHFFFAOYSA-N 0.000 claims 1
GNSXVNYZIFBAHH-UHFFFAOYSA-N 2-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1C1=CC=CC=C1 GNSXVNYZIFBAHH-UHFFFAOYSA-N 0.000 claims 1
LGCQZOJIBUXLTG-UHFFFAOYSA-N 2-[3-(3-piperidin-1-ylpyrazin-2-yl)azetidin-1-yl]-1,3-benzothiazole Chemical compound C1N(C=2SC3=CC=CC=C3N=2)CC1C1=NC=CN=C1N1CCCCC1 LGCQZOJIBUXLTG-UHFFFAOYSA-N 0.000 claims 1
CVSVOPWYLAPRHO-UHFFFAOYSA-N 2-[3-(3-pyrrolidin-1-ylpyrazin-2-yl)azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1N1CCCC1 CVSVOPWYLAPRHO-UHFFFAOYSA-N 0.000 claims 1
FZTGWWZZSGZACT-UHFFFAOYSA-N 2-[3-[3-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1C1=CCNCC1 FZTGWWZZSGZACT-UHFFFAOYSA-N 0.000 claims 1
ADTGWKNVZAKYAJ-UHFFFAOYSA-N 2-[3-[3-(1,4-diazepan-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1N1CCCNCC1 ADTGWKNVZAKYAJ-UHFFFAOYSA-N 0.000 claims 1
VFTXFFMYYDXVSG-UHFFFAOYSA-N 2-[3-[3-(1-methylindol-5-yl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound C1=CC=CC2=NC(N3CC(C3)C3=NC=CN=C3C=3C=C4C=CN(C4=CC=3)C)=NC=C21 VFTXFFMYYDXVSG-UHFFFAOYSA-N 0.000 claims 1
PSCLBKFDFGGCSX-UHFFFAOYSA-N 2-[3-[3-(1-methylindol-6-yl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound C1=CC=CC2=NC(N3CC(C3)C3=NC=CN=C3C3=CC=C4C=CN(C4=C3)C)=NC=C21 PSCLBKFDFGGCSX-UHFFFAOYSA-N 0.000 claims 1
NBPXRMDXHBAHKV-UHFFFAOYSA-N 2-[3-[3-(1h-indol-5-yl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound C1=C2NC=CC2=CC(C2=NC=CN=C2C2CN(C2)C=2N=C3C=CC=CC3=CN=2)=C1 NBPXRMDXHBAHKV-UHFFFAOYSA-N 0.000 claims 1
DYZJBSDSHQCFFN-UHFFFAOYSA-N 2-[3-[3-(1h-indol-6-yl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound C1=C2C=CNC2=CC(C2=NC=CN=C2C2CN(C2)C=2N=C3C=CC=CC3=CN=2)=C1 DYZJBSDSHQCFFN-UHFFFAOYSA-N 0.000 claims 1
QEGVNBGSRQQJNH-UHFFFAOYSA-N 2-[3-[3-(2,6-dimethoxypyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound COC1=NC(OC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 QEGVNBGSRQQJNH-UHFFFAOYSA-N 0.000 claims 1
MKUSSDGEWSNCEL-UHFFFAOYSA-N 2-[3-[3-(2-chlorophenyl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound ClC1=CC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CN=2)C1 MKUSSDGEWSNCEL-UHFFFAOYSA-N 0.000 claims 1
KDPIHHGZPGXTSY-UHFFFAOYSA-N 2-[3-[3-(2-fluorophenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound FC1=CC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 KDPIHHGZPGXTSY-UHFFFAOYSA-N 0.000 claims 1
NIJZAEZMLVBGDT-UHFFFAOYSA-N 2-[3-[3-(2-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound COC1=CC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 NIJZAEZMLVBGDT-UHFFFAOYSA-N 0.000 claims 1
DEQYQMWHIOLQAU-UHFFFAOYSA-N 2-[3-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound COC1=NC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 DEQYQMWHIOLQAU-UHFFFAOYSA-N 0.000 claims 1
COCJEYWHBJXKHQ-UHFFFAOYSA-N 2-[3-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 COCJEYWHBJXKHQ-UHFFFAOYSA-N 0.000 claims 1
NQGILYUCDYTIKP-UHFFFAOYSA-N 2-[3-[3-(2-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound CC1=CC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CN=2)C1 NQGILYUCDYTIKP-UHFFFAOYSA-N 0.000 claims 1
VVEZUWRDOPUAKM-UHFFFAOYSA-N 2-[3-[3-(2-methylpyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound CC1=NC=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 VVEZUWRDOPUAKM-UHFFFAOYSA-N 0.000 claims 1
SQVFKVRMHXYKSY-UHFFFAOYSA-N 2-[3-[3-(3,3-difluoroazetidin-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1C(F)(F)CN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 SQVFKVRMHXYKSY-UHFFFAOYSA-N 0.000 claims 1
HHZVYIJDUWINPD-UHFFFAOYSA-N 2-[3-[3-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1N1CC2CCCC2C1 HHZVYIJDUWINPD-UHFFFAOYSA-N 0.000 claims 1
YCYDGKBZNLZVGS-UHFFFAOYSA-N 2-[3-[3-(3,4-dichlorophenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 YCYDGKBZNLZVGS-UHFFFAOYSA-N 0.000 claims 1
AKXGDFXIXFLHPW-UHFFFAOYSA-N 2-[3-[3-(3,4-difluorophenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(F)C(F)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 AKXGDFXIXFLHPW-UHFFFAOYSA-N 0.000 claims 1
VWIIAPJXHVHVMV-UHFFFAOYSA-N 2-[3-[3-(3,4-dimethylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(C)C(C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 VWIIAPJXHVHVMV-UHFFFAOYSA-N 0.000 claims 1
SGNWQHDUSYAZBQ-UHFFFAOYSA-N 2-[3-[3-(3,6-dihydro-2h-pyran-4-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1C1=CCOCC1 SGNWQHDUSYAZBQ-UHFFFAOYSA-N 0.000 claims 1
FBKDIEYISUEUCG-UHFFFAOYSA-N 2-[3-[3-(3-chloro-4-ethoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(Cl)C(OCC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 FBKDIEYISUEUCG-UHFFFAOYSA-N 0.000 claims 1
OTZXJVIMKHNTGZ-UHFFFAOYSA-N 2-[3-[3-(3-chloro-4-fluorophenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(Cl)C(F)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 OTZXJVIMKHNTGZ-UHFFFAOYSA-N 0.000 claims 1
IJUYGRAUQYGJGL-UHFFFAOYSA-N 2-[3-[3-(3-chloro-4-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(Cl)C(C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 IJUYGRAUQYGJGL-UHFFFAOYSA-N 0.000 claims 1
AZJPWWAIWFAKOG-UHFFFAOYSA-N 2-[3-[3-(3-chloro-4-propoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(Cl)C(OCCC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 AZJPWWAIWFAKOG-UHFFFAOYSA-N 0.000 claims 1
HGGOXEQMOVLFOL-UHFFFAOYSA-N 2-[3-[3-(3-chlorophenyl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound ClC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CN=2)=C1 HGGOXEQMOVLFOL-UHFFFAOYSA-N 0.000 claims 1
XLOFPEOSUCLBOZ-UHFFFAOYSA-N 2-[3-[3-(3-ethoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound CCOC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 XLOFPEOSUCLBOZ-UHFFFAOYSA-N 0.000 claims 1
ATVCYPCFRLLEMX-UHFFFAOYSA-N 2-[3-[3-(3-fluoro-4-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(F)C(OC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 ATVCYPCFRLLEMX-UHFFFAOYSA-N 0.000 claims 1
ADKZTJSEDYYKTJ-UHFFFAOYSA-N 2-[3-[3-(3-fluoro-4-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(F)C(C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 ADKZTJSEDYYKTJ-UHFFFAOYSA-N 0.000 claims 1
XHVFFVHYOIEBSN-UHFFFAOYSA-N 2-[3-[3-(3-fluorophenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound FC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 XHVFFVHYOIEBSN-UHFFFAOYSA-N 0.000 claims 1
AXARMNBLJCRHKL-UHFFFAOYSA-N 2-[3-[3-(3-methoxyazetidin-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1C(OC)CN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 AXARMNBLJCRHKL-UHFFFAOYSA-N 0.000 claims 1
AHZFRRBULGKLML-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]-1,3-benzothiazole Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2SC3=CC=CC=C3N=2)=C1 AHZFRRBULGKLML-UHFFFAOYSA-N 0.000 claims 1
RDHIVJNWOKDLLZ-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]-1,6-naphthyridine Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CN=CC3=CC=2)=C1 RDHIVJNWOKDLLZ-UHFFFAOYSA-N 0.000 claims 1
KNNKWZHTBQEPEZ-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]-1,8-naphthyridine Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3N=CC=CC3=CC=2)=C1 KNNKWZHTBQEPEZ-UHFFFAOYSA-N 0.000 claims 1
LWOQORJIOSEUCU-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]-6-methylquinoline Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC(C)=CC3=CC=2)=C1 LWOQORJIOSEUCU-UHFFFAOYSA-N 0.000 claims 1
MCMYVCNIJZZIFL-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]-8-methylquinoline Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C(C)=CC=CC3=CC=2)=C1 MCMYVCNIJZZIFL-UHFFFAOYSA-N 0.000 claims 1
SRGSUXNYDDTNPH-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CN=2)=C1 SRGSUXNYDDTNPH-UHFFFAOYSA-N 0.000 claims 1
BRLSAPKNJAWFCU-UHFFFAOYSA-N 2-[3-[3-(3-methoxyphenyl)pyridin-2-yl]azetidin-1-yl]quinoline Chemical compound COC1=CC=CC(C=2C(=NC=CC=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 BRLSAPKNJAWFCU-UHFFFAOYSA-N 0.000 claims 1
OWKLYJSZNHPWQW-UHFFFAOYSA-N 2-[3-[3-(3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]-1,3-benzothiazole Chemical compound CC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2SC3=CC=CC=C3N=2)=C1 OWKLYJSZNHPWQW-UHFFFAOYSA-N 0.000 claims 1
JMBIWKMJFJTHAE-UHFFFAOYSA-N 2-[3-[3-(3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound CC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CN=2)=C1 JMBIWKMJFJTHAE-UHFFFAOYSA-N 0.000 claims 1
GHURNCZKBNHMLL-UHFFFAOYSA-N 2-[3-[3-(3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound CC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 GHURNCZKBNHMLL-UHFFFAOYSA-N 0.000 claims 1
PTTRYAKGUIQQEU-UHFFFAOYSA-N 2-[3-[3-(3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoxaline Chemical compound CC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=NC=2)=C1 PTTRYAKGUIQQEU-UHFFFAOYSA-N 0.000 claims 1
PLSBBSHQYZHBAI-UHFFFAOYSA-N 2-[3-[3-(3-methylphenyl)pyridin-2-yl]azetidin-1-yl]quinoline Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 PLSBBSHQYZHBAI-UHFFFAOYSA-N 0.000 claims 1
YTOQPEIWXUTGSX-UHFFFAOYSA-N 2-[3-[3-(3-phenylmethoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C=1C=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=CC=1OCC1=CC=CC=C1 YTOQPEIWXUTGSX-UHFFFAOYSA-N 0.000 claims 1
VTQRMJOGHSCBSR-UHFFFAOYSA-N 2-[3-[3-(3-phenylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1C(C=1)=CC=CC=1C1=CC=CC=C1 VTQRMJOGHSCBSR-UHFFFAOYSA-N 0.000 claims 1
CIADHTZUHITPIL-UHFFFAOYSA-N 2-[3-[3-(4,4-difluoropiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1CC(F)(F)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 CIADHTZUHITPIL-UHFFFAOYSA-N 0.000 claims 1
KSNXQLOLYJCHAR-UHFFFAOYSA-N 2-[3-[3-(4-chloro-3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(Cl)C(C)=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 KSNXQLOLYJCHAR-UHFFFAOYSA-N 0.000 claims 1
PETCOQAVAZRVRV-UHFFFAOYSA-N 2-[3-[3-(4-chlorophenyl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound C1=CC(Cl)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CN=2)C1 PETCOQAVAZRVRV-UHFFFAOYSA-N 0.000 claims 1
AGOBPYWIXHHVAO-UHFFFAOYSA-N 2-[3-[3-(4-ethoxy-3-fluorophenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(F)C(OCC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 AGOBPYWIXHHVAO-UHFFFAOYSA-N 0.000 claims 1
OGLUEMCGBMAAKD-UHFFFAOYSA-N 2-[3-[3-(4-ethoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(OCC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 OGLUEMCGBMAAKD-UHFFFAOYSA-N 0.000 claims 1
SYBREERITNUZIG-UHFFFAOYSA-N 2-[3-[3-(4-ethylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(CC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 SYBREERITNUZIG-UHFFFAOYSA-N 0.000 claims 1
MZBWYMMFJRWVPL-UHFFFAOYSA-N 2-[3-[3-(4-fluoro-3-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(F)C(OC)=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 MZBWYMMFJRWVPL-UHFFFAOYSA-N 0.000 claims 1
FHOJSCZBKAGUQX-UHFFFAOYSA-N 2-[3-[3-(4-fluorophenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(F)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 FHOJSCZBKAGUQX-UHFFFAOYSA-N 0.000 claims 1
ICQOXSAUAXHCJV-UHFFFAOYSA-N 2-[3-[3-(4-fluoropiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1CC(F)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 ICQOXSAUAXHCJV-UHFFFAOYSA-N 0.000 claims 1
RWKHALRIRXPTHN-UHFFFAOYSA-N 2-[3-[3-(4-methoxy-3-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(C)C(OC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 RWKHALRIRXPTHN-UHFFFAOYSA-N 0.000 claims 1
CFHXAIKVABZBSN-UHFFFAOYSA-N 2-[3-[3-(4-methoxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(OC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 CFHXAIKVABZBSN-UHFFFAOYSA-N 0.000 claims 1
MMGLONZJABWBLI-UHFFFAOYSA-N 2-[3-[3-(4-methyl-1,4-diazepan-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1CN(C)CCCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 MMGLONZJABWBLI-UHFFFAOYSA-N 0.000 claims 1
RRVNZJPAVNDUJG-UHFFFAOYSA-N 2-[3-[3-(4-methylimidazol-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=NC(C)=CN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 RRVNZJPAVNDUJG-UHFFFAOYSA-N 0.000 claims 1
SQXWMXUPJYJLNN-UHFFFAOYSA-N 2-[3-[3-(4-methylphenyl)pyrazin-2-yl]azetidin-1-yl]quinazoline Chemical compound C1=CC(C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CN=2)C1 SQXWMXUPJYJLNN-UHFFFAOYSA-N 0.000 claims 1
KPALJGIMYGHLPU-UHFFFAOYSA-N 2-[3-[3-(4-methylpiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1CC(C)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 KPALJGIMYGHLPU-UHFFFAOYSA-N 0.000 claims 1
IQQHTWWYNLIDCG-UHFFFAOYSA-N 2-[3-[3-(4-methylpyrazol-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline 1-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]pyrazole-4-carbonitrile Chemical compound CC=1C=NN(C1)C=1C(=NC=CN1)C1CN(C1)C1=NC2=CC=CC=C2C=C1.N1=C(C=CC2=CC=CC=C12)N1CC(C1)C=1C(=NC=CN1)N1N=CC(=C1)C#N IQQHTWWYNLIDCG-UHFFFAOYSA-N 0.000 claims 1
ZOQUKYHSVCTYAF-UHFFFAOYSA-N 2-[3-[3-(4-methylpyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=NC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 ZOQUKYHSVCTYAF-UHFFFAOYSA-N 0.000 claims 1
ZPEXJPGXTJNRPH-UHFFFAOYSA-N 2-[3-[3-(4-methylsulfonylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(S(=O)(=O)C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 ZPEXJPGXTJNRPH-UHFFFAOYSA-N 0.000 claims 1
VLZDWHYPWQCWIT-UHFFFAOYSA-N 2-[3-[3-(4-piperidin-1-ylsulfonylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C=1C=C(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)C=CC=1S(=O)(=O)N1CCCCC1 VLZDWHYPWQCWIT-UHFFFAOYSA-N 0.000 claims 1
IGTKPTLVDFIULZ-UHFFFAOYSA-N 2-[3-[3-(4-propan-2-yloxyphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(OC(C)C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 IGTKPTLVDFIULZ-UHFFFAOYSA-N 0.000 claims 1
NATHIXBDUKGXDD-UHFFFAOYSA-N 2-[3-[3-(4-propylphenyl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(CCC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 NATHIXBDUKGXDD-UHFFFAOYSA-N 0.000 claims 1
KHOHNWRCBXFLGH-UHFFFAOYSA-N 2-[3-[3-(4-quinolin-2-ylpiperidin-1-yl)pyrazin-2-yl]azetidin-1-yl]-1,8-naphthyridine Chemical compound C1=CC=CC2=NC(C3CCN(CC3)C3=NC=CN=C3C3CN(C3)C=3N=C4N=CC=CC4=CC=3)=CC=C21 KHOHNWRCBXFLGH-UHFFFAOYSA-N 0.000 claims 1
NWGJEBQGRVNOMD-UHFFFAOYSA-N 2-[3-[3-(5-methoxypyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CN=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 NWGJEBQGRVNOMD-UHFFFAOYSA-N 0.000 claims 1
XRLCLTWFIZLGGV-UHFFFAOYSA-N 2-[3-[3-(5-methylpyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CN=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 XRLCLTWFIZLGGV-UHFFFAOYSA-N 0.000 claims 1
PWPWFZAACFIVQT-UHFFFAOYSA-N 2-[3-[3-(6,6-dimethyl-2,3-dihydropyran-4-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound CC1(C)OCCC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 PWPWFZAACFIVQT-UHFFFAOYSA-N 0.000 claims 1
VXEYHEVCUFBTHK-UHFFFAOYSA-N 2-[3-[3-(6,6-dimethyl-2,5-dihydropyran-4-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1OC(C)(C)CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 VXEYHEVCUFBTHK-UHFFFAOYSA-N 0.000 claims 1
ZZCLFKMOJROBFV-UHFFFAOYSA-N 2-[3-[3-(6-methoxypyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC(OC)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 ZZCLFKMOJROBFV-UHFFFAOYSA-N 0.000 claims 1
NXOUSGIOCZEXJY-UHFFFAOYSA-N 2-[3-[3-(6-methylpyridin-3-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=NC(C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 NXOUSGIOCZEXJY-UHFFFAOYSA-N 0.000 claims 1
ZHYCDGSVRAZWBT-UHFFFAOYSA-N 2-[3-[3-(azepan-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1N(C=2N=C3C=CC=CC3=CC=2)CC1C1=NC=CN=C1N1CCCCCC1 ZHYCDGSVRAZWBT-UHFFFAOYSA-N 0.000 claims 1
GBNBAXXPRKUQES-KDURUIRLSA-N 2-[3-[3-[(1s,5r)-8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC=CC2=NC(N3CC(C3)C3=NC=CN=C3N3C[C@]4(CC[C@@](C3)(N4C)[H])[H])=CC=C21 GBNBAXXPRKUQES-KDURUIRLSA-N 0.000 claims 1
PUVXVNGTNDNHKO-GOSISDBHSA-N 2-[3-[3-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound COC[C@H]1CCCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 PUVXVNGTNDNHKO-GOSISDBHSA-N 0.000 claims 1
SDNKIARBFISGCI-MRXNPFEDSA-N 2-[3-[3-[(3R)-3-methylpyrrolidin-1-yl]pyridin-2-yl]azetidin-1-yl]quinoline Chemical compound C[C@H]1CN(CC1)C=1C(=NC=CC=1)C1CN(C1)C1=NC2=CC=CC=C2C=C1 SDNKIARBFISGCI-MRXNPFEDSA-N 0.000 claims 1
UAAOKEXGEUOKMR-QFIPXVFZSA-N 2-[3-[3-[(3s)-3-(2-phenylethyl)pyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C([C@@H]1CN(CC1)C=1C(=NC=CN=1)C1CN(C1)C=1N=C2C=CC=CC2=CC=1)CC1=CC=CC=C1 UAAOKEXGEUOKMR-QFIPXVFZSA-N 0.000 claims 1
NMXJQONRJWIBCV-INIZCTEOSA-N 2-[3-[3-[(3s)-3-fluoropyrrolidin-1-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1[C@@H](F)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 NMXJQONRJWIBCV-INIZCTEOSA-N 0.000 claims 1
SDNKIARBFISGCI-INIZCTEOSA-N 2-[3-[3-[(3s)-3-methylpyrrolidin-1-yl]pyridin-2-yl]azetidin-1-yl]quinoline Chemical compound C1[C@@H](C)CCN1C1=CC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 SDNKIARBFISGCI-INIZCTEOSA-N 0.000 claims 1
SAOAXGRPKDVTBO-UHFFFAOYSA-N 2-[3-[3-[4-(trifluoromethoxy)phenyl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 SAOAXGRPKDVTBO-UHFFFAOYSA-N 0.000 claims 1
BRSRAFPXFWYTJU-UHFFFAOYSA-N 2-[3-[3-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 BRSRAFPXFWYTJU-UHFFFAOYSA-N 0.000 claims 1
SUNHRNHFJARYBK-UHFFFAOYSA-N 2-[3-[3-[4-(trifluoromethyl)piperidin-1-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1CC(C(F)(F)F)CCN1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 SUNHRNHFJARYBK-UHFFFAOYSA-N 0.000 claims 1
LOJVCNNOLQKNKV-UHFFFAOYSA-N 2-[3-[3-[4-chloro-3-(trifluoromethyl)phenyl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 LOJVCNNOLQKNKV-UHFFFAOYSA-N 0.000 claims 1
FTFRNXKGDYEEIL-UHFFFAOYSA-N 2-[3-[3-[5-methoxy-5-(trifluoromethyl)cyclohexa-1,3-dien-1-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound COC1(CC(=CC=C1)C=1C(=NC=CN1)C1CN(C1)C1=NC2=CC=CC=C2C=C1)C(F)(F)F FTFRNXKGDYEEIL-UHFFFAOYSA-N 0.000 claims 1
LORJJIYHDKYRTE-UHFFFAOYSA-N 2-[3-[3-[6-(trifluoromethyl)pyridin-3-yl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 LORJJIYHDKYRTE-UHFFFAOYSA-N 0.000 claims 1
DSBBXAPRCAEDOO-UHFFFAOYSA-N 2-[[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methyl]-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CN(C1)CC1C1=NC=CN=C1C1=CC=CC=C1 DSBBXAPRCAEDOO-UHFFFAOYSA-N 0.000 claims 1
XQEWEJKWWWQRSB-UHFFFAOYSA-N 2-chloro-4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]phenol Chemical compound C1=C(Cl)C(O)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 XQEWEJKWWWQRSB-UHFFFAOYSA-N 0.000 claims 1
MQTIVRXHGJCGRT-UHFFFAOYSA-N 2-fluoro-4-[3-(1-quinazolin-2-ylazetidin-3-yl)pyrazin-2-yl]aniline Chemical compound C1=C(F)C(N)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CN=2)C1 MQTIVRXHGJCGRT-UHFFFAOYSA-N 0.000 claims 1
ASOSNPCBKUSOOV-UHFFFAOYSA-N 2-fluoro-4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]aniline 2-[3-(3-piperidin-1-ylpyrazin-2-yl)azetidin-1-yl]quinoline Chemical compound N1(CCCCC1)C=1C(=NC=CN1)C1CN(C1)C1=NC2=CC=CC=C2C=C1.FC1=C(C=CC(=C1)C1=NC=CN=C1C1CN(C1)C1=NC2=CC=CC=C2C=C1)N ASOSNPCBKUSOOV-UHFFFAOYSA-N 0.000 claims 1
IBEYASHWZVYIDO-UHFFFAOYSA-N 2-fluoro-4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 IBEYASHWZVYIDO-UHFFFAOYSA-N 0.000 claims 1
ADWTYIPFWRVNGG-UHFFFAOYSA-N 2-fluoro-5-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 ADWTYIPFWRVNGG-UHFFFAOYSA-N 0.000 claims 1
PHNCUGYJCDUYFY-UHFFFAOYSA-N 2-fluoro-5-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]phenol Chemical compound C1=C(F)C(O)=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 PHNCUGYJCDUYFY-UHFFFAOYSA-N 0.000 claims 1
WRZLBMWIUGOIIN-UHFFFAOYSA-N 2-methoxy-1-[4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 WRZLBMWIUGOIIN-UHFFFAOYSA-N 0.000 claims 1
SDWMOLHSKWAFJI-UHFFFAOYSA-N 2-methyl-2-[4-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]phenyl]propanenitrile Chemical compound C1=CC(C(C)(C#N)C)=CC=C1C1=NC=CN=C1C1CN(C=2N=C3C=CC=CC3=CC=2)C1 SDWMOLHSKWAFJI-UHFFFAOYSA-N 0.000 claims 1
UKIGMOSRQWLZER-UHFFFAOYSA-N 2-methyl-6-[3-(1-quinazolin-2-ylazetidin-3-yl)pyrazin-2-yl]isoquinolin-1-one Chemical compound C1=CC=CC2=NC(N3CC(C3)C3=NC=CN=C3C=3C=C4C=CN(C(C4=CC=3)=O)C)=NC=C21 UKIGMOSRQWLZER-UHFFFAOYSA-N 0.000 claims 1
GQGFOCQMOAVYOK-UHFFFAOYSA-N 3-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]aniline Chemical compound NC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 GQGFOCQMOAVYOK-UHFFFAOYSA-N 0.000 claims 1
YNMMFLGPECUAQX-UHFFFAOYSA-N 3-[3-(1-quinolin-2-ylazetidin-3-yl)pyrazin-2-yl]phenol Chemical compound OC1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 YNMMFLGPECUAQX-UHFFFAOYSA-N 0.000 claims 1
SPRYWRHFHPFKKH-UHFFFAOYSA-N 3-[3-(1-quinolin-2-ylazetidin-3-yl)quinoxalin-2-yl]phenol Chemical compound OC1=CC=CC(C=2C(=NC3=CC=CC=C3N=2)C2CN(C2)C=2N=C3C=CC=CC3=CC=2)=C1 SPRYWRHFHPFKKH-UHFFFAOYSA-N 0.000 claims 1
ASHBJSYDSOCJCJ-UHFFFAOYSA-N 3-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2C(=NC=CN=2)C2CN(C2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 ASHBJSYDSOCJCJ-UHFFFAOYSA-N 0.000 claims 1
SONOKAGRFXNMGT-UHFFFAOYSA-N 3-[3-[1-(1h-benzimidazole-2-carbonyl)azetidin-3-yl]pyrazin-2-yl]benzonitrile;(1-methylbenzimidazol-2-yl)-[3-(3-piperidin-1-ylpyrazin-2-yl)azetidin-1-yl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)N(C1)CC1C1=NC=CN=C1N1CCCCC1.N=1C2=CC=CC=C2NC=1C(=O)N(C1)CC1C1=NC=CN=C1C1=CC=CC(C#N)=C1 SONOKAGRFXNMGT-UHFFFAOYSA-N 0.000 claims 1
MEWANAYSUXYYNT-UHFFFAOYSA-N 3-[3-[3-(3,3-difluoropyrrolidin-1-yl)pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound FC1(CN(CC1)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1)F MEWANAYSUXYYNT-UHFFFAOYSA-N 0.000 claims 1
ADCFPTLCLLUXNM-UHFFFAOYSA-N 3-[3-[3-[3-(trifluoromethoxy)phenyl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound FC(OC=1C=C(C=CC1)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1)(F)F ADCFPTLCLLUXNM-UHFFFAOYSA-N 0.000 claims 1
RWOFYRCUKVPASU-UHFFFAOYSA-N 3-[3-[3-[3-(trifluoromethyl)phenyl]pyrazin-2-yl]azetidin-1-yl]quinoline Chemical compound FC(C=1C=C(C=CC1)C=1C(=NC=CN1)C1CN(C1)C=1C=NC2=CC=CC=C2C1)(F)F RWOFYRCUKVPASU-UHFFFAOYSA-N 0.000 claims 1
CRMSSXRCUWZLFR-UHFFFAOYSA-N 3-methyl-5-[3-(1-quinazolin-2-ylazetidin-3-yl)pyrazin-2-yl]-1h-benzimidazol-2-one Chemical compound C1=CC=CC2=NC(N3CC(C3)C3=NC=CN=C3C=3C=C4N(C(NC4=CC=3)=O)C)=NC=C21 CRMSSXRCUWZLFR-UHFFFAOYSA-N 0.000 claims 1
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JP2013510285A 2010-05-13 2011-05-11 Ｐｄｅ１０阻害剤として有用な窒素複素環化合物 Expired - Fee Related JP5702855B2 (ja)