JP5830094B2 - 置換イミダゾ［１，２−ａ］ピリミジンおよび−ピリジン - Google Patents

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Publication number

JP5830094B2

JP5830094B2 JP2013519035A JP2013519035A JP5830094B2 JP 5830094 B2 JP5830094 B2 JP 5830094B2 JP 2013519035 A JP2013519035 A JP 2013519035A JP 2013519035 A JP2013519035 A JP 2013519035A JP 5830094 B2 JP5830094 B2 JP 5830094B2

Authority

JP

Japan

Prior art keywords

phenyl

imidazo

pyridin

cyclobutylamine

alkyl

Prior art date

2010-07-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 title description 3
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical class C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 382
• 239000001257 hydrogen Substances 0.000 claims description 248
• 229910052739 hydrogen Inorganic materials 0.000 claims description 248
• -1 1-3C-alkyl Chemical group 0.000 claims description 240
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 207
• 229910052736 halogen Inorganic materials 0.000 claims description 202
• 150000002367 halogens Chemical group 0.000 claims description 202
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 146
• 238000000034 method Methods 0.000 claims description 135
• 150000003839 salts Chemical class 0.000 claims description 97
• 125000001424 substituent group Chemical group 0.000 claims description 88
• 125000003118 aryl group Chemical group 0.000 claims description 86
• 125000001072 heteroaryl group Chemical group 0.000 claims description 78
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 72
• 201000011510 cancer Diseases 0.000 claims description 65
• 229910052757 nitrogen Inorganic materials 0.000 claims description 63
• 150000001204 N-oxides Chemical class 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
• 201000010099 disease Diseases 0.000 claims description 49
• 238000011282 treatment Methods 0.000 claims description 46
• 125000006239 protecting group Chemical group 0.000 claims description 42
• 229920006395 saturated elastomer Polymers 0.000 claims description 36
• 239000002246 antineoplastic agent Substances 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 239000004480 active ingredient Substances 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 230000006882 induction of apoptosis Effects 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 14
• 230000003463 hyperproliferative effect Effects 0.000 claims description 13
• 230000002265 prevention Effects 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 6
• 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 description 5
• 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 description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 238000010511 deprotection reaction Methods 0.000 claims description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 125000004450 alkenylene group Chemical group 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 229910052727 yttrium Inorganic materials 0.000 claims description 3
• 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 description 2
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• 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 description 2
• SKFOXLKQCOJVTK-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-8-ol Chemical compound C=1C=C(C2=C(N3C=CC=C(O)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 SKFOXLKQCOJVTK-UHFFFAOYSA-N 0.000 claims description 2
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• 230000000973 chemotherapeutic effect Effects 0.000 claims description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
• 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 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 32
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• 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
• 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
• 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
• 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
• FBJAIPPQJRPHAE-UHFFFAOYSA-N 1-[4-[8-bromo-3-phenyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=C(Br)C3=N2)C(F)(F)F)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 FBJAIPPQJRPHAE-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
• 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
• IOYHLHFBJYDFEU-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-6-pyridin-3-ylimidazo[1,2-a]pyridine-8-carboxamide Chemical compound N1=C2C(C(=O)N)=CC(C=3C=NC=CC=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 IOYHLHFBJYDFEU-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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims 1
• 125000000753 cycloalkyl group Chemical group 0.000 claims 1
• JQPLJJDYLFEADK-UHFFFAOYSA-N ethyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OCC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 JQPLJJDYLFEADK-UHFFFAOYSA-N 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
• 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
• 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
• 229940080818 propionamide Drugs 0.000 claims 1
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• 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 98
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