JPWO2020239951A5 - - Google Patents
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- Publication number
- JPWO2020239951A5 JPWO2020239951A5 JP2021570930A JP2021570930A JPWO2020239951A5 JP WO2020239951 A5 JPWO2020239951 A5 JP WO2020239951A5 JP 2021570930 A JP2021570930 A JP 2021570930A JP 2021570930 A JP2021570930 A JP 2021570930A JP WO2020239951 A5 JPWO2020239951 A5 JP WO2020239951A5
- Authority
- JP
- Japan
- Prior art keywords
- quinazolin
- amine
- methyl
- methoxy
- fluorophenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 (R A R B )N- Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
- 125000002947 alkylene group Chemical group 0.000 claims 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 206010011224 Cough Diseases 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 5
- MYZJDILHQQODST-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[1-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C(F)(F)F MYZJDILHQQODST-UHFFFAOYSA-N 0.000 claims 5
- LJGYHNGYHHQIOD-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C LJGYHNGYHHQIOD-UHFFFAOYSA-N 0.000 claims 5
- QCZMGQXHYHFLMB-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1SC(=NN=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1SC(=NN=1)C QCZMGQXHYHFLMB-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- AUDLGQHDBBAHNA-UHFFFAOYSA-N 6-(4-fluorophenyl)-N-[1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=CC=1)NC(C)C1=NC(=NO1)C AUDLGQHDBBAHNA-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- LQOCLKXJJRUWSQ-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[1-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C(C)C LQOCLKXJJRUWSQ-UHFFFAOYSA-N 0.000 claims 3
- XRQJMGLSMSQPOL-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NOC(=N1)C XRQJMGLSMSQPOL-UHFFFAOYSA-N 0.000 claims 3
- DOPNNYDJALCIEW-UHFFFAOYSA-N 6-(4-fluorophenyl)-N-[1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-2-morpholin-4-ylquinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC(=NC2=CC=1)N1CCOCC1)NC(C)C1=NC(=NO1)C DOPNNYDJALCIEW-UHFFFAOYSA-N 0.000 claims 3
- FCKGVVHUSKVSMX-UHFFFAOYSA-N C(C)C1=NOC(=N1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=CC=C(C=C1)F)OC Chemical compound C(C)C1=NOC(=N1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=CC=C(C=C1)F)OC FCKGVVHUSKVSMX-UHFFFAOYSA-N 0.000 claims 3
- NENZTEKHDWGQQV-UHFFFAOYSA-N C1(CC1)NC1=NC2=CC=C(C=C2C(=N1)NC(C)C1=NC(=NO1)C)C1=CC=C(C=C1)F Chemical compound C1(CC1)NC1=NC2=CC=C(C=C2C(=N1)NC(C)C1=NC(=NO1)C)C1=CC=C(C=C1)F NENZTEKHDWGQQV-UHFFFAOYSA-N 0.000 claims 3
- VTABQHJHNJFIEK-LLVKDONJSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC(=NC2=C(C=1)OC)O)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC(=NC2=C(C=1)OC)O)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F VTABQHJHNJFIEK-LLVKDONJSA-N 0.000 claims 3
- HUKOVVKJGLDTEG-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C(C)C)C1=NC(=NO1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C(C)C)C1=NC(=NO1)C HUKOVVKJGLDTEG-UHFFFAOYSA-N 0.000 claims 3
- NYGAOZAGWUYDPY-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1C=NC(=CC=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1C=NC(=CC=1)C NYGAOZAGWUYDPY-UHFFFAOYSA-N 0.000 claims 3
- UCNOXLVSOJYWOS-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1C=NC(=CC=1)OC Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1C=NC(=CC=1)OC UCNOXLVSOJYWOS-UHFFFAOYSA-N 0.000 claims 3
- VXQIIRFHOFZBRM-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1OC(=NN=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1OC(=NN=1)C VXQIIRFHOFZBRM-UHFFFAOYSA-N 0.000 claims 3
- FVJXQCNIAQIDNV-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC1CS(CC1)(=O)=O Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC1CS(CC1)(=O)=O FVJXQCNIAQIDNV-UHFFFAOYSA-N 0.000 claims 3
- 208000013116 chronic cough Diseases 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- DDOBFWNYTJNCDI-UHFFFAOYSA-N 6-(3,5-difluoropyridin-2-yl)-8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound FC=1C(=NC=C(C=1)F)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NC(=CC=1)C DDOBFWNYTJNCDI-UHFFFAOYSA-N 0.000 claims 2
- DKPQEKXKZDLQHY-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-(2-methoxyethoxy)-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCCOC)NCC=1N=NC(=CC=1)C DKPQEKXKZDLQHY-UHFFFAOYSA-N 0.000 claims 2
- KLYUOOJQZVYCOM-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-([1,2,4]triazolo[4,3-a]pyrimidin-3-ylmethyl)quinazolin-4-amine Chemical compound N=1N=C(N2C=1N=CC=C2)CNC1=NC=NC2=C(C=C(C=C12)C1=CC=C(C=C1)F)OC KLYUOOJQZVYCOM-UHFFFAOYSA-N 0.000 claims 2
- BRMGBVVQFGPZMH-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(1-methylpiperidin-4-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1CCN(CC1)C BRMGBVVQFGPZMH-UHFFFAOYSA-N 0.000 claims 2
- DMPJTLBMVLVCCM-CQSZACIVSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C DMPJTLBMVLVCCM-CQSZACIVSA-N 0.000 claims 2
- IKBYRWPBKOTVFM-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[2-(6-methylpyridin-3-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCCC=1C=NC(=CC=1)C IKBYRWPBKOTVFM-UHFFFAOYSA-N 0.000 claims 2
- XSBJQAMWPKCLTJ-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[[2-(trifluoromethyl)pyrimidin-5-yl]methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1C=NC(=NC=1)C(F)(F)F XSBJQAMWPKCLTJ-UHFFFAOYSA-N 0.000 claims 2
- SUSYLIFVVDLEKM-UHFFFAOYSA-N 6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]-8-(morpholin-2-ylmethoxy)quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC1CNCCO1)NCC=1N=NC(=CC=1)C SUSYLIFVVDLEKM-UHFFFAOYSA-N 0.000 claims 2
- IIMDBOLYMIUPNV-UHFFFAOYSA-N 6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]-8-(oxan-4-yloxy)quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)NCC=1N=NC(=CC=1)C IIMDBOLYMIUPNV-UHFFFAOYSA-N 0.000 claims 2
- VKUIKUMAYRCIHT-UHFFFAOYSA-N 6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]-8-(oxetan-3-ylmethoxy)quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC1COC1)NCC=1N=NC(=CC=1)C VKUIKUMAYRCIHT-UHFFFAOYSA-N 0.000 claims 2
- IUIKQGQIZKAEEU-UHFFFAOYSA-N 6-(5-chloropyridin-2-yl)-8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound ClC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NC(=CC=1)C IUIKQGQIZKAEEU-UHFFFAOYSA-N 0.000 claims 2
- ACWUQGWJKSJWEX-UHFFFAOYSA-N 6-(5-ethyl-1,3-thiazol-2-yl)-8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound C(C)C1=CN=C(S1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NC(=CC=1)C ACWUQGWJKSJWEX-UHFFFAOYSA-N 0.000 claims 2
- TXNAFGCACZJMBG-CYBMUJFWSA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C TXNAFGCACZJMBG-CYBMUJFWSA-N 0.000 claims 2
- HNAGBRIXYIIIBP-LLVKDONJSA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F HNAGBRIXYIIIBP-LLVKDONJSA-N 0.000 claims 2
- ALFVYEIHIYCISV-JTQLQIEISA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[(1S)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@@H](C)C1=NOC(=N1)C ALFVYEIHIYCISV-JTQLQIEISA-N 0.000 claims 2
- KJQWLUCUECTVSD-UHFFFAOYSA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1OC(=NN=1)C KJQWLUCUECTVSD-UHFFFAOYSA-N 0.000 claims 2
- GTADTGLAOGYVSF-UHFFFAOYSA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[1-[6-(trifluoromethyl)pyridazin-3-yl]ethyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1N=NC(=CC=1)C(F)(F)F GTADTGLAOGYVSF-UHFFFAOYSA-N 0.000 claims 2
- IFYKAERNUFDGJZ-UHFFFAOYSA-N 6-[[[6-(4-fluorophenyl)-8-methoxyquinazolin-4-yl]amino]methyl]-1H-pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=CC=CC(N1)=O IFYKAERNUFDGJZ-UHFFFAOYSA-N 0.000 claims 2
- QWOMEONAAGEJPD-GFCCVEGCSA-N 8-methoxy-6-(5-methylpyrimidin-2-yl)-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F)C1=NC=C(C=N1)C QWOMEONAAGEJPD-GFCCVEGCSA-N 0.000 claims 2
- HXSMGOPFPVUKJQ-GFCCVEGCSA-N 8-methoxy-N-[(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-6-(5-methylpyridin-2-yl)quinazolin-4-amine Chemical class COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C1=NOC(=N1)C)C1=NC=C(C=C1)C HXSMGOPFPVUKJQ-GFCCVEGCSA-N 0.000 claims 2
- PMWPMYMVWQKCRM-LLVKDONJSA-N 8-methoxy-N-[(1R)-1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]-6-(5-methylpyrimidin-2-yl)quinazolin-4-amine Chemical class COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1OC(=NN=1)C)C1=NC=C(C=N1)C PMWPMYMVWQKCRM-LLVKDONJSA-N 0.000 claims 2
- YIZUUTIBWVQJDQ-CQSZACIVSA-N 8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]-6-(5-methylpyrimidin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)C1=NC=C(C=N1)C YIZUUTIBWVQJDQ-CQSZACIVSA-N 0.000 claims 2
- YIZUUTIBWVQJDQ-AWEZNQCLSA-N 8-methoxy-N-[(1S)-1-(6-methylpyridazin-3-yl)ethyl]-6-(5-methylpyrimidin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@@H](C)C=1N=NC(=CC=1)C)C1=NC=C(C=N1)C YIZUUTIBWVQJDQ-AWEZNQCLSA-N 0.000 claims 2
- DXVYXSKIAHBUOD-UHFFFAOYSA-N 8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]-6-(5-methylpyridin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=NC=C(C=C1)C DXVYXSKIAHBUOD-UHFFFAOYSA-N 0.000 claims 2
- GGFOOBGCDDETLF-UHFFFAOYSA-N 8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]-6-(5-methylpyrimidin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=NC=C(C=N1)C GGFOOBGCDDETLF-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- PXUZXRRLQRPYBO-UHFFFAOYSA-N C1(CC1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=CC=C(C=C1)F)OC Chemical compound C1(CC1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=CC=C(C=C1)F)OC PXUZXRRLQRPYBO-UHFFFAOYSA-N 0.000 claims 2
- QQHYCZFQCXNOMY-UHFFFAOYSA-N CC1=CC=C(C=N1)CNC1=NC=NC2=CC=C(C=C12)C1=CC=C(C=C1)C Chemical compound CC1=CC=C(C=N1)CNC1=NC=NC2=CC=C(C=C12)C1=CC=C(C=C1)C QQHYCZFQCXNOMY-UHFFFAOYSA-N 0.000 claims 2
- MGRZWYCHJIQXJT-UHFFFAOYSA-N CC1=CC=C(N=N1)CNC1=NC=NC2=CC=C(C=C12)C1=NC=C(C=C1)C Chemical compound CC1=CC=C(N=N1)CNC1=NC=NC2=CC=C(C=C12)C1=NC=C(C=C1)C MGRZWYCHJIQXJT-UHFFFAOYSA-N 0.000 claims 2
- URVRSEJOBPXIRQ-UHFFFAOYSA-N CC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=CC=1)NCC=1C=NC(=CC=1)C Chemical compound CC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=CC=1)NCC=1C=NC(=CC=1)C URVRSEJOBPXIRQ-UHFFFAOYSA-N 0.000 claims 2
- BFOFHOYBTLGLKZ-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NC(=NO1)C)C1=NC=C(C=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NC(=NO1)C)C1=NC=C(C=C1)C BFOFHOYBTLGLKZ-UHFFFAOYSA-N 0.000 claims 2
- FKBUUIVRECGTEM-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C=1SC(=CN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C=1SC(=CN=1)C FKBUUIVRECGTEM-UHFFFAOYSA-N 0.000 claims 2
- KARYMXGPZWGIBY-SNVBAGLBSA-N COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1C=CC(=[N+](C=1)[O-])C(F)(F)F)C=1SC(=NN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1C=CC(=[N+](C=1)[O-])C(F)(F)F)C=1SC(=NN=1)C KARYMXGPZWGIBY-SNVBAGLBSA-N 0.000 claims 2
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- WHVVOAXGRYCTBT-NSHDSACASA-N 6-(4-fluorophenyl)-8-methoxy-N-[(1S)-1-(3-methyl-1H-1,2,4-triazol-5-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@@H](C)C1=NN=C(N1)C WHVVOAXGRYCTBT-NSHDSACASA-N 0.000 claims 1
- MVFDTGLDHVFQSA-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(2-methyl-1,2,4-triazol-3-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NC=NN1C MVFDTGLDHVFQSA-UHFFFAOYSA-N 0.000 claims 1
- KXQSSOUZOSMHQV-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(2-methylindazol-6-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1C=CC2=CN(N=C2C=1)C KXQSSOUZOSMHQV-UHFFFAOYSA-N 0.000 claims 1
- LYANMVIDTSVQSD-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(2-methyltetrazol-5-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NN(N=1)C LYANMVIDTSVQSD-UHFFFAOYSA-N 0.000 claims 1
- OVIKAXAUSWVRFD-HNNXBMFYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(2S)-1-pyrrolidin-1-ylpropan-2-yl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](CN1CCCC1)C OVIKAXAUSWVRFD-HNNXBMFYSA-N 0.000 claims 1
- UTMOZBUCRCAZBJ-QGZVFWFLSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(3R)-1-methylpiperidin-3-yl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H]1CN(CCC1)C UTMOZBUCRCAZBJ-QGZVFWFLSA-N 0.000 claims 1
- ZRMTYFOCDMBLCD-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=CC2=C(N(CCO2)C)C=C1 ZRMTYFOCDMBLCD-UHFFFAOYSA-N 0.000 claims 1
- YGIDJQRWZYFTPX-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(5-methylpyridin-2-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NC=C(C=C1)C YGIDJQRWZYFTPX-UHFFFAOYSA-N 0.000 claims 1
- FOEYZLXALIGEST-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[(6-morpholin-4-ylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NC(=CC=1)N1CCOCC1 FOEYZLXALIGEST-UHFFFAOYSA-N 0.000 claims 1
- CSASXSBPJUBMOP-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[1-(1H-1,2,4-triazol-5-yl)ethyl]quinazolin-4-amine Chemical compound N=1N=C(NC=1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=CC=C(C=C1)F)OC CSASXSBPJUBMOP-UHFFFAOYSA-N 0.000 claims 1
- RASCKORQFCAIRQ-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[1-(3-pyridin-4-yl-1,2,4-oxadiazol-5-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C1=CC=NC=C1 RASCKORQFCAIRQ-UHFFFAOYSA-N 0.000 claims 1
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- SLYHBFRBBCOFCP-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[2-(4-methylpiperazin-1-yl)-1-phenylethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(CN1CCN(CC1)C)C1=CC=CC=C1 SLYHBFRBBCOFCP-UHFFFAOYSA-N 0.000 claims 1
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- XDYMOGDSJIMGCV-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[[2-(trifluoromethyl)pyridin-4-yl]methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=CC(=NC=C1)C(F)(F)F XDYMOGDSJIMGCV-UHFFFAOYSA-N 0.000 claims 1
- LEEVQKOYVWHSKE-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[[3-(piperidin-1-ylmethyl)-1,2,4-oxadiazol-5-yl]methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NC(=NO1)CN1CCCCC1 LEEVQKOYVWHSKE-UHFFFAOYSA-N 0.000 claims 1
- JFRJSZYHXGGOFQ-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[[6-(2,2,2-trifluoroethoxy)pyridazin-3-yl]methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NC(=CC=1)OCC(F)(F)F JFRJSZYHXGGOFQ-UHFFFAOYSA-N 0.000 claims 1
- CPSRIIPMXGTVMP-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1C=NC(=CC=1)N1CCN(CC1)C CPSRIIPMXGTVMP-UHFFFAOYSA-N 0.000 claims 1
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- RFPZAGUUAOUWNN-HXUWFJFHSA-N 6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]-8-[(3R)-pyrrolidin-3-yl]oxyquinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)O[C@H]1CNCC1)NCC=1N=NC(=CC=1)C RFPZAGUUAOUWNN-HXUWFJFHSA-N 0.000 claims 1
- RFPZAGUUAOUWNN-FQEVSTJZSA-N 6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]-8-[(3S)-pyrrolidin-3-yl]oxyquinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)O[C@@H]1CNCC1)NCC=1N=NC(=CC=1)C RFPZAGUUAOUWNN-FQEVSTJZSA-N 0.000 claims 1
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- WGKWTJQXWJQXDW-CYBMUJFWSA-N 6-[5-(difluoromethyl)pyridin-2-yl]-8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]quinazolin-4-amine Chemical compound FC(C=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C)F WGKWTJQXWJQXDW-CYBMUJFWSA-N 0.000 claims 1
- XXIRPZMYAIBGHR-UHFFFAOYSA-N 6-[5-(dimethylamino)pyridin-2-yl]-8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound CN(C=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NC(=CC=1)C)C XXIRPZMYAIBGHR-UHFFFAOYSA-N 0.000 claims 1
- KCNHTQGFGFHXMN-UHFFFAOYSA-N 6-[8-methoxy-4-[(6-methylpyridazin-3-yl)methylamino]quinazolin-6-yl]pyridin-3-ol Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=CC=C(C=N1)O KCNHTQGFGFHXMN-UHFFFAOYSA-N 0.000 claims 1
- FCUXUVHPPPHOFX-UHFFFAOYSA-N 6-[8-methoxy-4-[(6-methylpyridazin-3-yl)methylamino]quinazolin-6-yl]pyridine-3-carbonitrile Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=NC=C(C#N)C=C1 FCUXUVHPPPHOFX-UHFFFAOYSA-N 0.000 claims 1
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- ODWGTTJHNDGSBD-UHFFFAOYSA-N 8-(cyclopropylmethoxy)-6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound C1(CC1)COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=CC=C(C=C1)F ODWGTTJHNDGSBD-UHFFFAOYSA-N 0.000 claims 1
- FZQBCYPBPYFYRH-UHFFFAOYSA-N 8-[3-(dimethylamino)propoxy]-6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound CN(CCCOC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=CC=C(C=C1)F)C FZQBCYPBPYFYRH-UHFFFAOYSA-N 0.000 claims 1
- HHWQIDNRYKHENQ-UHFFFAOYSA-N 8-ethoxy-6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound C(C)OC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=CC=C(C=C1)F HHWQIDNRYKHENQ-UHFFFAOYSA-N 0.000 claims 1
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- GJIJUGVZSICVGK-UHFFFAOYSA-N 8-methoxy-6-(4-methoxyphenyl)-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C1=CC=C(C=C1)OC GJIJUGVZSICVGK-UHFFFAOYSA-N 0.000 claims 1
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- GGVBUUNLDORHCW-GFCCVEGCSA-N 8-methoxy-6-(4-methylpyrazol-1-yl)-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F)N1N=CC(=C1)C GGVBUUNLDORHCW-GFCCVEGCSA-N 0.000 claims 1
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- HHAGUORIMPCBND-SECBINFHSA-N 8-methoxy-6-(5-methyl-1,3,4-thiadiazol-2-yl)-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F)C=1SC(=NN=1)C HHAGUORIMPCBND-SECBINFHSA-N 0.000 claims 1
- SSHNNMNJIVAOPL-UHFFFAOYSA-N 8-methoxy-6-(6-methoxypyridazin-3-yl)-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C=1N=NC(=CC=1)OC SSHNNMNJIVAOPL-UHFFFAOYSA-N 0.000 claims 1
- ZLSRCSKFURFULU-LLVKDONJSA-N 8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]-6-(5-methyl-1,3,4-thiadiazol-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)C=1SC(=NN=1)C ZLSRCSKFURFULU-LLVKDONJSA-N 0.000 claims 1
- CGRWKMXTYRQQBF-OAHLLOKOSA-N 8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]-6-(5-methylpyridin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)C1=NC=C(C=C1)C CGRWKMXTYRQQBF-OAHLLOKOSA-N 0.000 claims 1
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- QFPFVYGVLPFALA-UHFFFAOYSA-N 8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]-6-(4-methyl-1,3-thiazol-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C=1SC=C(N=1)C QFPFVYGVLPFALA-UHFFFAOYSA-N 0.000 claims 1
- ZKYZZZRRSUGBCW-UHFFFAOYSA-N 8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]-6-(6-methylpyridin-3-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C=1C=NC(=CC=1)C ZKYZZZRRSUGBCW-UHFFFAOYSA-N 0.000 claims 1
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| BR112021022099A2 (pt) | 2019-05-31 | 2021-12-28 | Chiesi Farm Spa | Derivados de amino quinazolina como inibidores de p2x3 |
| KR20220030222A (ko) | 2019-05-31 | 2022-03-10 | 이케나 온콜로지, 인코포레이티드 | Tead 억제제 및 이의 용도 |
| CN114222741B (zh) * | 2019-05-31 | 2025-12-30 | 奇斯药制品公司 | 作为p2x3抑制剂的吡啶并嘧啶类衍生物 |
| CN114222737B (zh) | 2019-05-31 | 2024-07-26 | 詹森药业有限公司 | NF-κB诱导激酶的小分子抑制剂 |
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| WO2022063205A1 (zh) * | 2020-09-24 | 2022-03-31 | 中国医药研究开发中心有限公司 | 芳基甲酰胺类化合物及其制备方法和医药用途 |
| EP4234548A4 (en) * | 2020-10-20 | 2024-10-23 | Suzhou Zelgen Biopharmaceutical Co., Ltd. | SUBSTITUTED BENZO OR PYRIDOPYRIMIDINE AMINE INHIBITOR, ITS PREPARATION METHOD AND ITS APPLICATION |
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| JP2023550830A (ja) * | 2020-11-27 | 2023-12-05 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | Ｐ２ｘ３阻害剤としての（アザ）キノリン４－アミン誘導体 |
| CN112661803A (zh) * | 2020-12-17 | 2021-04-16 | 上海药明康德新药开发有限公司 | DNA编码化合物库构建中On-DNA 4-胺基喹唑啉化合物的合成方法 |
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- 2021-11-22 SA SA521430920A patent/SA521430920B1/ar unknown
- 2021-11-25 IL IL288405A patent/IL288405A/en unknown
- 2021-11-29 CL CL2021003165A patent/CL2021003165A1/es unknown
- 2021-12-14 CO CONC2021/0017031A patent/CO2021017031A2/es unknown
-
2025
- 2025-02-27 JP JP2025029719A patent/JP2025098014A/ja active Pending
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