JP2013531684A5 - - Google Patents
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- JP2013531684A5 JP2013531684A5 JP2013519035A JP2013519035A JP2013531684A5 JP 2013531684 A5 JP2013531684 A5 JP 2013531684A5 JP 2013519035 A JP2013519035 A JP 2013519035A JP 2013519035 A JP2013519035 A JP 2013519035A JP 2013531684 A5 JP2013531684 A5 JP 2013531684A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- imidazo
- pyridin
- cyclobutylamine
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229910052739 hydrogen Inorganic materials 0.000 claims 42
- 239000001257 hydrogen Substances 0.000 claims 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 42
- 229910052736 halogen Inorganic materials 0.000 claims 40
- 150000002367 halogens Chemical group 0.000 claims 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 16
- -1 1-3C-alkyl Chemical group 0.000 claims 14
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 14
- 125000006239 protecting group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- UDVSAIBACXRTOQ-UHFFFAOYSA-N 1-[4-(3-phenyl-6-pyridin-3-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C=2C=NC=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 UDVSAIBACXRTOQ-UHFFFAOYSA-N 0.000 claims 2
- ABXVUGZVUCYNCO-UHFFFAOYSA-N 1-[4-(3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ABXVUGZVUCYNCO-UHFFFAOYSA-N 0.000 claims 2
- KKDGQLCPXPQQJS-UHFFFAOYSA-N 1-[4-(6-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(Br)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 KKDGQLCPXPQQJS-UHFFFAOYSA-N 0.000 claims 2
- HPQFDZVVQQRZHS-UHFFFAOYSA-N 1-[4-[3-phenyl-7-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C2=CNN=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 HPQFDZVVQQRZHS-UHFFFAOYSA-N 0.000 claims 2
- JBTAEEKPONTXSL-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)N)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 JBTAEEKPONTXSL-UHFFFAOYSA-N 0.000 claims 2
- SNTBNZPFJQCQAZ-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-8-carboxamide Chemical compound N1=C2C(C(=O)N)=CC=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 SNTBNZPFJQCQAZ-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 230000006882 induction of apoptosis Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- ZLUZMRGENYSWJR-NTUHNPAUSA-N (e)-3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]prop-2-enamide Chemical compound N12C=C(/C=C/C(=O)N)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 ZLUZMRGENYSWJR-NTUHNPAUSA-N 0.000 claims 1
- RXXZXZOLEIMPSZ-KPKJPENVSA-N (e)-3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]prop-2-enamide Chemical compound N1=C2C=C(/C=C/C(=O)N)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 RXXZXZOLEIMPSZ-KPKJPENVSA-N 0.000 claims 1
- FJZWNBISHWDALI-UHFFFAOYSA-N 1-[2-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyrimidin-7-yl]oxyethyl]pyrrolidin-2-one Chemical compound C=1C=C(C2=C(N3C=CC(OCCN4C(CCC4)=O)=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 FJZWNBISHWDALI-UHFFFAOYSA-N 0.000 claims 1
- WARCYKWNWXOOSP-UHFFFAOYSA-N 1-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]-3-methylurea Chemical compound N12C=C(NC(=O)NC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 WARCYKWNWXOOSP-UHFFFAOYSA-N 0.000 claims 1
- VDKHXAAHUVGQOQ-UHFFFAOYSA-N 1-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]ethanol Chemical compound N12C=C(C(O)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 VDKHXAAHUVGQOQ-UHFFFAOYSA-N 0.000 claims 1
- NTBZGYRYZJXCHI-UHFFFAOYSA-N 1-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]ethanone Chemical compound N12C=C(C(=O)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 NTBZGYRYZJXCHI-UHFFFAOYSA-N 0.000 claims 1
- DOLDYUXQWQXPRT-UHFFFAOYSA-N 1-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]-3-methylurea Chemical compound N1=C2C=C(NC(=O)NC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 DOLDYUXQWQXPRT-UHFFFAOYSA-N 0.000 claims 1
- LYEYCIOFBOBJRV-UHFFFAOYSA-N 1-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]ethanone Chemical compound N1=C2C=C(C(=O)C)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LYEYCIOFBOBJRV-UHFFFAOYSA-N 0.000 claims 1
- JUHKWLMPWQGMOU-UHFFFAOYSA-N 1-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]pyridin-2-one Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)N2C(C=CC=C2)=O)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 JUHKWLMPWQGMOU-UHFFFAOYSA-N 0.000 claims 1
- UPJRTEWYTRCMGI-UHFFFAOYSA-N 1-[4-(3,6-diphenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=NC3=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 UPJRTEWYTRCMGI-UHFFFAOYSA-N 0.000 claims 1
- IGZBZGFHJNODTL-UHFFFAOYSA-N 1-[4-(3,7-diphenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=NC3=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 IGZBZGFHJNODTL-UHFFFAOYSA-N 0.000 claims 1
- XXQGWNIKFHCTIN-UHFFFAOYSA-N 1-[4-(3-phenyl-6-pyrazol-1-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)N2N=CC=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XXQGWNIKFHCTIN-UHFFFAOYSA-N 0.000 claims 1
- MHPDKKLTPXQKGE-UHFFFAOYSA-N 1-[4-(3-phenyl-6-pyridin-4-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C=2C=CN=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 MHPDKKLTPXQKGE-UHFFFAOYSA-N 0.000 claims 1
- SSMHOKCXASOSDR-UHFFFAOYSA-N 1-[4-(3-phenyl-7-propan-2-yloxyimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OC(C)C)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 SSMHOKCXASOSDR-UHFFFAOYSA-N 0.000 claims 1
- PTBIXVGGTHAJMK-UHFFFAOYSA-N 1-[4-(3-phenyl-7-propoxyimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OCCC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 PTBIXVGGTHAJMK-UHFFFAOYSA-N 0.000 claims 1
- RBZYXASPIFZSKF-UHFFFAOYSA-N 1-[4-(3-phenyl-7-pyrazol-1-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)N2N=CC=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 RBZYXASPIFZSKF-UHFFFAOYSA-N 0.000 claims 1
- UFAPEESOYAUIKS-UHFFFAOYSA-N 1-[4-(3-phenyl-7-pyridin-2-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C=2N=CC=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 UFAPEESOYAUIKS-UHFFFAOYSA-N 0.000 claims 1
- ZFZHMEKRPREPAJ-UHFFFAOYSA-N 1-[4-(3-phenyl-7-pyridin-3-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C=2C=NC=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZFZHMEKRPREPAJ-UHFFFAOYSA-N 0.000 claims 1
- ZBWUPNWRTMRORJ-UHFFFAOYSA-N 1-[4-(3-phenyl-7-pyridin-4-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C=2C=CN=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZBWUPNWRTMRORJ-UHFFFAOYSA-N 0.000 claims 1
- LMBQMEOEJDKMKM-UHFFFAOYSA-N 1-[4-(3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LMBQMEOEJDKMKM-UHFFFAOYSA-N 0.000 claims 1
- AQQGZTUNRJVZAQ-UHFFFAOYSA-N 1-[4-(5-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C(C)=CC=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 AQQGZTUNRJVZAQ-UHFFFAOYSA-N 0.000 claims 1
- OWTNOKGCBLFOFA-UHFFFAOYSA-N 1-[4-(6,8-dimethoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(OC)C=C(OC)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 OWTNOKGCBLFOFA-UHFFFAOYSA-N 0.000 claims 1
- UYGBNGMSQVKEOD-UHFFFAOYSA-N 1-[4-(6-bromo-8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(Br)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 UYGBNGMSQVKEOD-UHFFFAOYSA-N 0.000 claims 1
- NSVGZPTZQRHMMS-UHFFFAOYSA-N 1-[4-(6-chloro-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(Cl)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 NSVGZPTZQRHMMS-UHFFFAOYSA-N 0.000 claims 1
- WJXWHMPAMHDJER-UHFFFAOYSA-N 1-[4-(6-chloro-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(Cl)C=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 WJXWHMPAMHDJER-UHFFFAOYSA-N 0.000 claims 1
- LCABWUQLPSYHLY-UHFFFAOYSA-N 1-[4-(6-chloro-8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(Cl)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LCABWUQLPSYHLY-UHFFFAOYSA-N 0.000 claims 1
- NVABCHXZMMWMST-UHFFFAOYSA-N 1-[4-(6-cyclopropyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C2CC2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 NVABCHXZMMWMST-UHFFFAOYSA-N 0.000 claims 1
- BBKYAPLWNWFTDX-UHFFFAOYSA-N 1-[4-(6-ethenyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=C)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 BBKYAPLWNWFTDX-UHFFFAOYSA-N 0.000 claims 1
- MXIHJUGRVIDEMV-UHFFFAOYSA-N 1-[4-(6-ethenyl-8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(C=C)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 MXIHJUGRVIDEMV-UHFFFAOYSA-N 0.000 claims 1
- BRVNNBSKYFJJGM-UHFFFAOYSA-N 1-[4-(6-ethoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(OCC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 BRVNNBSKYFJJGM-UHFFFAOYSA-N 0.000 claims 1
- ZNLHXUTZXOXBOT-UHFFFAOYSA-N 1-[4-(6-ethoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(OCC)C=NC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 ZNLHXUTZXOXBOT-UHFFFAOYSA-N 0.000 claims 1
- JVOLVCNRQRHUHA-UHFFFAOYSA-N 1-[4-(6-ethyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(CC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 JVOLVCNRQRHUHA-UHFFFAOYSA-N 0.000 claims 1
- LGWBCYYZSZQYET-UHFFFAOYSA-N 1-[4-(6-ethyl-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(CC)C=NC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 LGWBCYYZSZQYET-UHFFFAOYSA-N 0.000 claims 1
- YYGYICYUALVYOQ-UHFFFAOYSA-N 1-[4-(6-ethyl-8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(CC)C=C(OC)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 YYGYICYUALVYOQ-UHFFFAOYSA-N 0.000 claims 1
- QBHGSIJMOROVHB-UHFFFAOYSA-N 1-[4-(6-fluoro-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(F)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 QBHGSIJMOROVHB-UHFFFAOYSA-N 0.000 claims 1
- DBJSYPFMXMIPHU-UHFFFAOYSA-N 1-[4-(6-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(OC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 DBJSYPFMXMIPHU-UHFFFAOYSA-N 0.000 claims 1
- JBNWJZGHPXUORC-UHFFFAOYSA-N 1-[4-(6-methoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(OC)C=NC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 JBNWJZGHPXUORC-UHFFFAOYSA-N 0.000 claims 1
- DVQPLUOKKCUTKU-UHFFFAOYSA-N 1-[4-(6-methyl-3-phenyl-8-pyridin-3-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C12=NC(C=3C=CC(=CC=3)C3(N)CCC3)=C(C=3C=CC=CC=3)N2C=C(C)C=C1C1=CC=CN=C1 DVQPLUOKKCUTKU-UHFFFAOYSA-N 0.000 claims 1
- NMIWYCWLYFRSLJ-UHFFFAOYSA-N 1-[4-(6-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 NMIWYCWLYFRSLJ-UHFFFAOYSA-N 0.000 claims 1
- CIKUORISQCEFPK-UHFFFAOYSA-N 1-[4-(6-methyl-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(C)C=NC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 CIKUORISQCEFPK-UHFFFAOYSA-N 0.000 claims 1
- FBANRZKZWPNHSN-UHFFFAOYSA-N 1-[4-(7-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(Br)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 FBANRZKZWPNHSN-UHFFFAOYSA-N 0.000 claims 1
- PMLIJZCWPLPZLY-UHFFFAOYSA-N 1-[4-(7-chloro-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(Cl)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 PMLIJZCWPLPZLY-UHFFFAOYSA-N 0.000 claims 1
- VYFQASOWIMQBFB-UHFFFAOYSA-N 1-[4-(7-cyclohexyloxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(OC4CCCCC4)=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 VYFQASOWIMQBFB-UHFFFAOYSA-N 0.000 claims 1
- DYEWQJXBDVQCKP-UHFFFAOYSA-N 1-[4-(7-cyclopropyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C2CC2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DYEWQJXBDVQCKP-UHFFFAOYSA-N 0.000 claims 1
- GPJNKJQYJDBCRJ-UHFFFAOYSA-N 1-[4-(7-cyclopropyl-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=NC3=N2)C2CC2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GPJNKJQYJDBCRJ-UHFFFAOYSA-N 0.000 claims 1
- PANSYNBNNASHEW-UHFFFAOYSA-N 1-[4-(7-ethenyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(C=C)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 PANSYNBNNASHEW-UHFFFAOYSA-N 0.000 claims 1
- MYNRPWMBDKXPIV-UHFFFAOYSA-N 1-[4-(7-ethoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C=C(OCC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 MYNRPWMBDKXPIV-UHFFFAOYSA-N 0.000 claims 1
- LFEWFIMPGRKMKG-UHFFFAOYSA-N 1-[4-(7-ethyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C=C(CC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LFEWFIMPGRKMKG-UHFFFAOYSA-N 0.000 claims 1
- SYCVULGNXZQCGX-UHFFFAOYSA-N 1-[4-(7-ethynyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C#C)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 SYCVULGNXZQCGX-UHFFFAOYSA-N 0.000 claims 1
- SFUWGIZEPMCDBL-UHFFFAOYSA-N 1-[4-(7-fluoro-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(F)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 SFUWGIZEPMCDBL-UHFFFAOYSA-N 0.000 claims 1
- MOGYPQBWQDORPP-UHFFFAOYSA-N 1-[4-(7-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C=C(OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 MOGYPQBWQDORPP-UHFFFAOYSA-N 0.000 claims 1
- CBOPZRDROLVYRN-UHFFFAOYSA-N 1-[4-(7-methoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 CBOPZRDROLVYRN-UHFFFAOYSA-N 0.000 claims 1
- LJBPADJHDSNGPA-UHFFFAOYSA-N 1-[4-(7-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C=C(C)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LJBPADJHDSNGPA-UHFFFAOYSA-N 0.000 claims 1
- UHNOLIYOGJZRNT-UHFFFAOYSA-N 1-[4-(7-methyl-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 UHNOLIYOGJZRNT-UHFFFAOYSA-N 0.000 claims 1
- ZYLHBIQWOJSANG-UHFFFAOYSA-N 1-[4-(7-phenoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(OC=4C=CC=CC=4)=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZYLHBIQWOJSANG-UHFFFAOYSA-N 0.000 claims 1
- XGDHYAZSEQCNOK-UHFFFAOYSA-N 1-[4-(8-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(Br)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XGDHYAZSEQCNOK-UHFFFAOYSA-N 0.000 claims 1
- MXWXDYUJBMSKPA-UHFFFAOYSA-N 1-[4-(8-chloro-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(Cl)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 MXWXDYUJBMSKPA-UHFFFAOYSA-N 0.000 claims 1
- RHAMTEMTFSTAJW-UHFFFAOYSA-N 1-[4-(8-cyclopropyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C2CC2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 RHAMTEMTFSTAJW-UHFFFAOYSA-N 0.000 claims 1
- DKFLSQRUSSOPJV-UHFFFAOYSA-N 1-[4-(8-ethenyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C=C)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DKFLSQRUSSOPJV-UHFFFAOYSA-N 0.000 claims 1
- POVSBIPSJMIOSH-UHFFFAOYSA-N 1-[4-(8-ethoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OCC)=CC=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 POVSBIPSJMIOSH-UHFFFAOYSA-N 0.000 claims 1
- OZHUDFAFDJKZSG-UHFFFAOYSA-N 1-[4-(8-fluoro-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(F)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 OZHUDFAFDJKZSG-UHFFFAOYSA-N 0.000 claims 1
- MZAMJYVYNLRQJQ-UHFFFAOYSA-N 1-[4-(8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 MZAMJYVYNLRQJQ-UHFFFAOYSA-N 0.000 claims 1
- VXKMKCHPPGQXNG-UHFFFAOYSA-N 1-[4-(8-methyl-3-phenyl-6-pyridin-3-ylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C(C)=CC(C=3C=NC=CC=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 VXKMKCHPPGQXNG-UHFFFAOYSA-N 0.000 claims 1
- UFWMQKLUNMFTTL-UHFFFAOYSA-N 1-[4-(8-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C(C)=CC=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 UFWMQKLUNMFTTL-UHFFFAOYSA-N 0.000 claims 1
- OFRLOQQQWQBNPQ-UHFFFAOYSA-N 1-[4-[3-phenyl-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C2=CNN=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 OFRLOQQQWQBNPQ-UHFFFAOYSA-N 0.000 claims 1
- ALKDQQZUPXPOBW-UHFFFAOYSA-N 1-[4-[3-phenyl-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C2=NNC=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ALKDQQZUPXPOBW-UHFFFAOYSA-N 0.000 claims 1
- DNLPIJXLHBUSLS-UHFFFAOYSA-N 1-[4-[3-phenyl-7-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C=2NN=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DNLPIJXLHBUSLS-UHFFFAOYSA-N 0.000 claims 1
- SUOJVVLUIMLFQX-UHFFFAOYSA-N 1-[4-[3-phenyl-8-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C2=CNN=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 SUOJVVLUIMLFQX-UHFFFAOYSA-N 0.000 claims 1
- DPQDHVZPZYLUNI-UHFFFAOYSA-N 1-[4-[3-phenyl-8-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C=2NN=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DPQDHVZPZYLUNI-UHFFFAOYSA-N 0.000 claims 1
- VBLRWCPOAATBTO-UHFFFAOYSA-N 1-[4-[6-(1-methylpyrazol-4-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C1=NN(C)C=C1C1=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2C=C1 VBLRWCPOAATBTO-UHFFFAOYSA-N 0.000 claims 1
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- BSWGDKWWXTZXEK-UHFFFAOYSA-N 1-[4-[6-(1h-imidazol-2-yl)-8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(C=3NC=CN=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 BSWGDKWWXTZXEK-UHFFFAOYSA-N 0.000 claims 1
- XBISPBWLIODRFQ-UHFFFAOYSA-N 1-[4-[6-(1h-imidazol-5-yl)-8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(C=3NC=NC=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 XBISPBWLIODRFQ-UHFFFAOYSA-N 0.000 claims 1
- OAXWKOAQPWOHNF-UHFFFAOYSA-N 1-[4-[6-(3-methylimidazol-4-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound CN1C=NC=C1C1=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2C=C1 OAXWKOAQPWOHNF-UHFFFAOYSA-N 0.000 claims 1
- MNKWQDBCRJYVMM-UHFFFAOYSA-N 1-[4-[6-(5-methyl-1h-pyrazol-3-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1N=C(C)C=C1C1=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2C=C1 MNKWQDBCRJYVMM-UHFFFAOYSA-N 0.000 claims 1
- URLXVJBLJIEHQN-UHFFFAOYSA-N 1-[4-[6-(methoxymethyl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N12C=C(COC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 URLXVJBLJIEHQN-UHFFFAOYSA-N 0.000 claims 1
- RLWYOWMXBOMUSN-UHFFFAOYSA-N 1-[4-[6-chloro-7-methyl-3-phenyl-8-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound CC=1C(Cl)=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2C=1C1=CC=NN1 RLWYOWMXBOMUSN-UHFFFAOYSA-N 0.000 claims 1
- FQVDDVQBSVTNFF-UHFFFAOYSA-N 1-[4-[6-chloro-8-(4-fluorophenyl)-7-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound CC=1C(Cl)=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2C=1C1=CC=C(F)C=C1 FQVDDVQBSVTNFF-UHFFFAOYSA-N 0.000 claims 1
- XHPBTXUIIKKTCV-UHFFFAOYSA-N 1-[4-[6-methyl-3-phenyl-8-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C12=NC(C=3C=CC(=CC=3)C3(N)CCC3)=C(C=3C=CC=CC=3)N2C=C(C)C=C1C=1C=NNC=1 XHPBTXUIIKKTCV-UHFFFAOYSA-N 0.000 claims 1
- OXVAKPMYZFUKFH-UHFFFAOYSA-N 1-[4-[7,8-dimethyl-3-phenyl-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N12C=C(C=3NN=CC=3)C(C)=C(C)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 OXVAKPMYZFUKFH-UHFFFAOYSA-N 0.000 claims 1
- VQGZGYYXZFFFCR-UHFFFAOYSA-N 1-[4-[7-(1-methylpyrazol-4-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C1=NN(C)C=C1C1=CC2=NC(C=3C=CC(=CC=3)C3(N)CCC3)=C(C=3C=CC=CC=3)N2C=C1 VQGZGYYXZFFFCR-UHFFFAOYSA-N 0.000 claims 1
- XMWNNGHXZDVUJV-UHFFFAOYSA-N 1-[4-[7-(2-aminoethoxy)-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OCCN)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 XMWNNGHXZDVUJV-UHFFFAOYSA-N 0.000 claims 1
- YNOSHXGRYKDBMO-UHFFFAOYSA-N 1-[4-[7-(2-methoxyethoxy)-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OCCOC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 YNOSHXGRYKDBMO-UHFFFAOYSA-N 0.000 claims 1
- UPXGPTVFECKXRX-UHFFFAOYSA-N 1-[4-[7-(3-methylimidazol-4-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound CN1C=NC=C1C1=CC2=NC(C=3C=CC(=CC=3)C3(N)CCC3)=C(C=3C=CC=CC=3)N2C=C1 UPXGPTVFECKXRX-UHFFFAOYSA-N 0.000 claims 1
- GTFSRNKPWDHODK-UHFFFAOYSA-N 1-[4-[7-(4-fluorophenyl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C=2C=CC(F)=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GTFSRNKPWDHODK-UHFFFAOYSA-N 0.000 claims 1
- SYMPTBRPUWCVTC-UHFFFAOYSA-N 1-[4-[7-[(2-methoxypyridin-4-yl)methoxy]-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C1=NC(OC)=CC(COC2=NC3=NC(=C(N3C=C2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C2(N)CCC2)=C1 SYMPTBRPUWCVTC-UHFFFAOYSA-N 0.000 claims 1
- GHEHSCYHOBFXLO-UHFFFAOYSA-N 1-[4-[7-[(6-methoxypyridin-3-yl)methoxy]-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C1=NC(OC)=CC=C1COC1=NC2=NC(C=3C=CC(=CC=3)C3(N)CCC3)=C(C=3C=CC=CC=3)N2C=C1 GHEHSCYHOBFXLO-UHFFFAOYSA-N 0.000 claims 1
- KSFUYHJYEXMKDO-UHFFFAOYSA-N 1-[4-[8-(1h-indazol-6-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C=2C=C3NN=CC3=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 KSFUYHJYEXMKDO-UHFFFAOYSA-N 0.000 claims 1
- XQIJCRMHBBDRAW-UHFFFAOYSA-N 1-[4-[8-(3-fluorophenyl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C=2C=C(F)C=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XQIJCRMHBBDRAW-UHFFFAOYSA-N 0.000 claims 1
- IAHBHCUTIPCVMP-UHFFFAOYSA-N 1-[4-[8-(4-fluorophenyl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C=2C=CC(F)=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 IAHBHCUTIPCVMP-UHFFFAOYSA-N 0.000 claims 1
- FVXZQCOTPCONRK-UHFFFAOYSA-N 1-[4-[8-(5-methoxypyridin-3-yl)-6-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound COC1=CN=CC(C=2C3=NC(=C(N3C=C(C)C=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C2(N)CCC2)=C1 FVXZQCOTPCONRK-UHFFFAOYSA-N 0.000 claims 1
- WTRPETLHOOKVDX-UHFFFAOYSA-N 1-[4-[8-methoxy-3-phenyl-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(C3=CNN=C3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 WTRPETLHOOKVDX-UHFFFAOYSA-N 0.000 claims 1
- AWHHMDMYGALEAJ-UHFFFAOYSA-N 1-[4-[8-methyl-3-phenyl-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2C(C)=CC(C3=CNN=C3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 AWHHMDMYGALEAJ-UHFFFAOYSA-N 0.000 claims 1
- UOGFBQHXZGZNHI-UHFFFAOYSA-N 1-[4-[8-methyl-3-phenyl-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2C(C)=CC(C=3NN=CC=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 UOGFBQHXZGZNHI-UHFFFAOYSA-N 0.000 claims 1
- XGYWJGDFOXGYAO-UHFFFAOYSA-N 1-[4-[8-methyl-6-(5-methyl-1h-pyrazol-3-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1N=C(C)C=C1C1=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2C(C)=C1 XGYWJGDFOXGYAO-UHFFFAOYSA-N 0.000 claims 1
- FYAKXCWSZDVBDW-UHFFFAOYSA-N 1-[[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyrimidin-7-yl]oxymethyl]cyclopropane-1-carboxamide Chemical compound C1=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2N=C1OCC1(C(=O)N)CC1 FYAKXCWSZDVBDW-UHFFFAOYSA-N 0.000 claims 1
- ZFZVEUDOVBTELB-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-1h-imidazo[1,2-a]pyridin-7-one Chemical compound C=1C=C(C2=C(N3C=CC(=O)C=C3N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZFZVEUDOVBTELB-UHFFFAOYSA-N 0.000 claims 1
- YANODRAYNDRPAT-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-1h-imidazo[1,2-a]pyrimidin-7-one Chemical compound C=1C=C(C2=C(N3C=CC(O)=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 YANODRAYNDRPAT-UHFFFAOYSA-N 0.000 claims 1
- FIYJBZFUABAWAP-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridine-8-carboxamide Chemical compound N1=C2C(C(=O)N)=CC(C3=CNN=C3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 FIYJBZFUABAWAP-UHFFFAOYSA-N 0.000 claims 1
- FPPAQOQEDKFECY-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide Chemical compound N1=C2C(C(=O)N)=CC(C=3NN=CC=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 FPPAQOQEDKFECY-UHFFFAOYSA-N 0.000 claims 1
- YAYCLPNKCZCYNV-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-n-propan-2-ylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NC(C)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 YAYCLPNKCZCYNV-UHFFFAOYSA-N 0.000 claims 1
- VDWVIQZXVQSPBH-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-amine Chemical compound N12C=C(N)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 VDWVIQZXVQSPBH-UHFFFAOYSA-N 0.000 claims 1
- XBQDOZCBHDDKPA-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-ol Chemical compound C=1C=C(C2=C(N3C=C(O)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XBQDOZCBHDDKPA-UHFFFAOYSA-N 0.000 claims 1
- UVMWGRJYEMCBSN-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-amine Chemical compound N1=C2C=C(N)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 UVMWGRJYEMCBSN-UHFFFAOYSA-N 0.000 claims 1
- GLKFXRCYMJOMSD-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GLKFXRCYMJOMSD-UHFFFAOYSA-N 0.000 claims 1
- GGNJMPIPRZOFQC-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)N)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 GGNJMPIPRZOFQC-UHFFFAOYSA-N 0.000 claims 1
- SCHNZNCVVMTSHR-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carboxylic acid;hydrochloride Chemical compound Cl.C=1C=C(C2=C(N3C=C(C=CC3=N2)C(O)=O)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 SCHNZNCVVMTSHR-UHFFFAOYSA-N 0.000 claims 1
- IWPHXFMQLJNWQA-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-7-carbonitrile Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 IWPHXFMQLJNWQA-UHFFFAOYSA-N 0.000 claims 1
- ZATBMOVJDNGDAP-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-8-carbonitrile Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZATBMOVJDNGDAP-UHFFFAOYSA-N 0.000 claims 1
- VQUHRMBRIIYMST-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-6-bromo-3-phenylimidazo[1,2-a]pyridine-8-carboxamide Chemical compound N1=C2C(C(=O)N)=CC(Br)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 VQUHRMBRIIYMST-UHFFFAOYSA-N 0.000 claims 1
- HHRIIEGZTIJORA-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-6-methyl-3-phenylimidazo[1,2-a]pyridine-8-carboxamide Chemical compound N12C=C(C)C=C(C(N)=O)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 HHRIIEGZTIJORA-UHFFFAOYSA-N 0.000 claims 1
- SIIXQCPGTUWGJH-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-7,8-dimethyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(N)=O)C(C)=C(C)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 SIIXQCPGTUWGJH-UHFFFAOYSA-N 0.000 claims 1
- WURJZSZUOFJYBH-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-7-methoxy-3-phenylimidazo[1,2-a]pyridine-8-carbonitrile Chemical compound N1=C2C(C#N)=C(OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 WURJZSZUOFJYBH-UHFFFAOYSA-N 0.000 claims 1
- QNLKKXRGJRQSDH-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-8-bromo-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)N)C=C(Br)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 QNLKKXRGJRQSDH-UHFFFAOYSA-N 0.000 claims 1
- VHGGDRGBYFHHAS-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-8-chloro-3-phenylimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C=1C=C(C2=C(N3C=C(C=C(Cl)C3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 VHGGDRGBYFHHAS-UHFFFAOYSA-N 0.000 claims 1
- ZLVBVXHVGVTLST-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-8-methoxy-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N1=C2C(OC)=CC(C(N)=O)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 ZLVBVXHVGVTLST-UHFFFAOYSA-N 0.000 claims 1
- HNAHVCDJEMVGAX-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-8-methyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N1=C2C(C)=CC(C(N)=O)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 HNAHVCDJEMVGAX-UHFFFAOYSA-N 0.000 claims 1
- SPEBRUYKFDLZQY-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n,n-dimethyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)N(C)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 SPEBRUYKFDLZQY-UHFFFAOYSA-N 0.000 claims 1
- UBSFWERTKGDEBO-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-(2-fluoroethyl)-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C(=O)NCCF)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 UBSFWERTKGDEBO-UHFFFAOYSA-N 0.000 claims 1
- NPOGSQHOERHPNH-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-(2-hydroxyethyl)-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C(=O)NCCO)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 NPOGSQHOERHPNH-UHFFFAOYSA-N 0.000 claims 1
- MYLUEKSBIRDYJU-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-(2-methoxyethyl)-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCOC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 MYLUEKSBIRDYJU-UHFFFAOYSA-N 0.000 claims 1
- QTMAVKBPASHUTM-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-(cyclopropylmethyl)-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C(=O)NCC2CC2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 QTMAVKBPASHUTM-UHFFFAOYSA-N 0.000 claims 1
- VVJALPIXKAWUMN-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-cyclopropyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C(=O)NC2CC2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 VVJALPIXKAWUMN-UHFFFAOYSA-N 0.000 claims 1
- OQBNARLLVQAWES-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-ethyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 OQBNARLLVQAWES-UHFFFAOYSA-N 0.000 claims 1
- VMDVOPZSDPSBAT-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-ethyl-3-phenylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NCC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 VMDVOPZSDPSBAT-UHFFFAOYSA-N 0.000 claims 1
- POHBSNCKJNYVAL-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-hydroxy-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C(=O)NO)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 POHBSNCKJNYVAL-UHFFFAOYSA-N 0.000 claims 1
- DRBMEYLWCNBQFV-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-hydroxy-3-phenylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C(=O)NO)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DRBMEYLWCNBQFV-UHFFFAOYSA-N 0.000 claims 1
- IIJPSYGMQNPMKH-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-methoxy-n-methyl-3-phenylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)N(C)OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 IIJPSYGMQNPMKH-UHFFFAOYSA-N 0.000 claims 1
- MGFSZAHJUZQYSI-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-methyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 MGFSZAHJUZQYSI-UHFFFAOYSA-N 0.000 claims 1
- KJVRCOXMJJVLCG-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-methyl-3-phenylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 KJVRCOXMJJVLCG-UHFFFAOYSA-N 0.000 claims 1
- AFBOMFWMMSRZBK-UHFFFAOYSA-N 3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]-1h-pyridin-2-one Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C=2C(=NC=CC=2)O)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 AFBOMFWMMSRZBK-UHFFFAOYSA-N 0.000 claims 1
- XUBHFJGWXWMFCJ-UHFFFAOYSA-N 3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]propanamide Chemical compound N1=C2C=C(CCC(=O)N)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 XUBHFJGWXWMFCJ-UHFFFAOYSA-N 0.000 claims 1
- WBZUWSGBNWQZOF-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]methanol Chemical compound C=1C=C(C2=C(N3C=C(CO)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 WBZUWSGBNWQZOF-UHFFFAOYSA-N 0.000 claims 1
- NQBZWIXQIDSOBC-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]urea Chemical compound N12C=C(NC(=O)N)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 NQBZWIXQIDSOBC-UHFFFAOYSA-N 0.000 claims 1
- JAEYTKRVBLGLPC-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C(=O)N2CCCC2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 JAEYTKRVBLGLPC-UHFFFAOYSA-N 0.000 claims 1
- YRBLOFAVEJSWNY-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]methanol Chemical compound C=1C=C(C2=C(N3C=CC(CO)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 YRBLOFAVEJSWNY-UHFFFAOYSA-N 0.000 claims 1
- LQMSNTHUOFIWKS-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]urea Chemical compound N1=C2C=C(NC(=O)N)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LQMSNTHUOFIWKS-UHFFFAOYSA-N 0.000 claims 1
- IYTYBBKZINCQJF-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-8-yl]methanol Chemical compound C=1C=C(C2=C(N3C=CC=C(CO)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 IYTYBBKZINCQJF-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000000973 chemotherapeutic effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- JLCNPKCWGOTCNE-UHFFFAOYSA-N ethyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-7-carboxylate Chemical compound N1=C2C=C(C(=O)OCC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 JLCNPKCWGOTCNE-UHFFFAOYSA-N 0.000 claims 1
- JHQZYACKMYYVOI-UHFFFAOYSA-N ethyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-8-carboxylate Chemical compound N1=C2C(C(=O)OCC)=CC=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 JHQZYACKMYYVOI-UHFFFAOYSA-N 0.000 claims 1
- XJZYLKQYZWOOKZ-UHFFFAOYSA-N ethyl 2-[4-(1-aminocyclobutyl)phenyl]-8-bromo-3-phenylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OCC)C=C(Br)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 XJZYLKQYZWOOKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- FTNAWZGCDDQDJB-OQLLNIDSSA-N methyl (e)-3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]prop-2-enoate Chemical compound N12C=C(/C=C/C(=O)OC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 FTNAWZGCDDQDJB-OQLLNIDSSA-N 0.000 claims 1
- LKWMVZZEONIZRJ-MDWZMJQESA-N methyl (e)-3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]prop-2-enoate Chemical compound N1=C2C=C(/C=C/C(=O)OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LKWMVZZEONIZRJ-MDWZMJQESA-N 0.000 claims 1
- UFOIRIHRBHLNIF-UHFFFAOYSA-N methyl 2-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]oxyacetate Chemical compound N1=C2C=C(OCC(=O)OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 UFOIRIHRBHLNIF-UHFFFAOYSA-N 0.000 claims 1
- FQSAGOQZJDXZJW-UHFFFAOYSA-N methyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-7-carboxylate Chemical compound N1=C2C=C(C(=O)OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 FQSAGOQZJDXZJW-UHFFFAOYSA-N 0.000 claims 1
- YODVXSCOWOEGCP-UHFFFAOYSA-N methyl 2-[4-(1-aminocyclobutyl)phenyl]-8-chloro-3-phenylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=C(Cl)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 YODVXSCOWOEGCP-UHFFFAOYSA-N 0.000 claims 1
- CDOOEFFJOKTQAQ-UHFFFAOYSA-N methyl 2-[4-(1-aminocyclobutyl)phenyl]-8-methoxy-3-phenylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=C(OC)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 CDOOEFFJOKTQAQ-UHFFFAOYSA-N 0.000 claims 1
- LNHXAMFKIDOTFU-UHFFFAOYSA-N methyl 3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]propanoate Chemical compound N1=C2C=C(CCC(=O)OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LNHXAMFKIDOTFU-UHFFFAOYSA-N 0.000 claims 1
- LRTGOWXJKJYYGQ-UHFFFAOYSA-N n-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]acetamide Chemical compound N12C=C(NC(=O)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 LRTGOWXJKJYYGQ-UHFFFAOYSA-N 0.000 claims 1
- NBYASNLRMKAGQF-UHFFFAOYSA-N n-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]methanesulfonamide Chemical compound N12C=C(NS(=O)(=O)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 NBYASNLRMKAGQF-UHFFFAOYSA-N 0.000 claims 1
- PGYSOMADUOJSOK-UHFFFAOYSA-N n-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]acetamide Chemical compound N1=C2C=C(NC(=O)C)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 PGYSOMADUOJSOK-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| DK2694510T3 (en) * | 2011-04-07 | 2016-01-18 | Bayer Ip Gmbh | IMIDAZOPYRIDAZINER AS AKT kinase inhibitors |
| US9370517B2 (en) * | 2012-01-10 | 2016-06-21 | Bayer Intellectual Property Gmbh | Substituted pyrazolopyrimidines as Akt kinase inhibitors |
| EP2802586B1 (en) * | 2012-01-10 | 2016-05-25 | Bayer Intellectual Property GmbH | Substituted imidazopyrazines as akt kinase inhibitors |
| BR112015000675B1 (pt) * | 2012-07-13 | 2022-07-12 | UCB Biopharma SRL | Derivados de imidazopiridina como moduladores da atividade de tnf |
| PE20161573A1 (es) | 2014-02-13 | 2017-01-19 | Incyte Corp | Ciclopropilamina como inhibidor de la lsd1 |
| EP3392244A1 (en) | 2014-02-13 | 2018-10-24 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
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| US9493450B2 (en) | 2014-02-13 | 2016-11-15 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| CA2946538A1 (en) | 2014-04-04 | 2015-10-08 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
| JPWO2016136928A1 (ja) | 2015-02-27 | 2017-08-31 | 大鵬薬品工業株式会社 | イミダゾオキサジンの結晶、当該結晶を含む医薬組成物、及び当該結晶の製造方法 |
| PE20180455A1 (es) | 2015-04-03 | 2018-03-05 | Incyte Corp | Compuestos heterociclicos como inhibidores de lsd1 |
| CN106188063A (zh) * | 2015-05-08 | 2016-12-07 | 中国科学院上海药物研究所 | 用作Lp-PLA2抑制剂的双环类化合物、其制备方法及医药用途 |
| SG10202001219UA (en) | 2015-08-12 | 2020-03-30 | Incyte Corp | Salts of an lsd1 inhibitor |
| US11883404B2 (en) | 2016-03-04 | 2024-01-30 | Taiho Pharmaceuticals Co., Ltd. | Preparation and composition for treatment of malignant tumors |
| CN109414410B (zh) | 2016-04-22 | 2022-08-12 | 因赛特公司 | Lsd1抑制剂的制剂 |
| WO2018013430A2 (en) | 2016-07-12 | 2018-01-18 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus infection |
| KR20190043437A (ko) | 2017-10-18 | 2019-04-26 | 씨제이헬스케어 주식회사 | 단백질 키나제 억제제로서의 헤테로고리 화합물 |
| GB201811695D0 (en) * | 2018-07-17 | 2018-08-29 | Salvensis | Compounds for use in the treatment of fascioliasis |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| KR102195348B1 (ko) | 2018-11-15 | 2020-12-24 | 에이치케이이노엔 주식회사 | 단백질 키나제 억제제로서의 신규 화합물 및 이를 포함하는 약제학적 조성물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1898903T3 (da) * | 2005-06-10 | 2013-07-01 | Merck Sharp & Dohme | Inhibitorer af Akt-aktivitet |
| AR064010A1 (es) * | 2006-12-06 | 2009-03-04 | Merck & Co Inc | Inhibidores de la actividad de la akt |
| MX2010001745A (es) * | 2007-08-14 | 2010-03-10 | Bayer Schering Pharma Ag | Imidazoles fusionados para el tratamiento del cancer. |
| EA201001456A1 (ru) | 2008-03-21 | 2011-06-30 | Новартис Аг | Новые гетероциклические соединения и их применение |
| CA2726317A1 (en) * | 2008-06-03 | 2009-12-10 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| WO2010088177A1 (en) | 2009-02-02 | 2010-08-05 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| US8168652B2 (en) | 2009-03-12 | 2012-05-01 | Merck Sharp & Dohme Corp. | Inhibitors of AKT activity |
| US8691825B2 (en) | 2009-04-01 | 2014-04-08 | Merck Sharp & Dohme Corp. | Inhibitors of AKT activity |
| EP2473495A1 (en) | 2009-09-18 | 2012-07-11 | Almac Discovery Limited | Pharmaceutical compounds |
| GB0919380D0 (en) | 2009-11-04 | 2009-12-23 | Almac Discovery Ltd | Pharmaceutical compouds |
-
2011
- 2011-07-07 US US13/808,430 patent/US8975265B2/en not_active Expired - Fee Related
- 2011-07-07 EP EP11730003.8A patent/EP2593451B1/en active Active
- 2011-07-07 JP JP2013519035A patent/JP5830094B2/ja not_active Expired - Fee Related
- 2011-07-07 ES ES11730003.8T patent/ES2552841T3/es active Active
- 2011-07-07 WO PCT/EP2011/061508 patent/WO2012007345A2/en not_active Ceased
- 2011-07-07 CN CN201180043391.XA patent/CN103097384B/zh not_active Expired - Fee Related
- 2011-07-07 CA CA2804845A patent/CA2804845A1/en not_active Abandoned
- 2011-07-11 UY UY0001033503A patent/UY33503A/es not_active Application Discontinuation
- 2011-07-12 AR ARP110102496A patent/AR090005A1/es unknown
- 2011-07-12 TW TW100124649A patent/TW201206933A/zh unknown
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