JP2021500340A5 - - Google Patents
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- JP2021500340A5 JP2021500340A5 JP2020521911A JP2020521911A JP2021500340A5 JP 2021500340 A5 JP2021500340 A5 JP 2021500340A5 JP 2020521911 A JP2020521911 A JP 2020521911A JP 2020521911 A JP2020521911 A JP 2020521911A JP 2021500340 A5 JP2021500340 A5 JP 2021500340A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- cycloalkyl
- membered
- phenyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 774
- -1 Amino, Thio Chemical class 0.000 claims description 395
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 177
- 150000001875 compounds Chemical class 0.000 claims description 165
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
- 150000003839 salts Chemical class 0.000 claims description 139
- 125000001424 substituent group Chemical group 0.000 claims description 125
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 122
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 87
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 86
- 125000005843 halogen group Chemical group 0.000 claims description 77
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 75
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 229910052799 carbon Inorganic materials 0.000 claims description 70
- 125000003545 alkoxy group Chemical group 0.000 claims description 69
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 68
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 66
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 58
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 50
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 30
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 29
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 25
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 21
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- HWNHQKGIFMHZHG-UHFFFAOYSA-N imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound NC(=O)c1cn2ccnc2cn1 HWNHQKGIFMHZHG-UHFFFAOYSA-N 0.000 claims description 20
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 19
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 19
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 10
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- JPJMLQRVGZBWPD-UHFFFAOYSA-N 2-methyl-1h-imidazol-5-amine Chemical compound CC1=NC=C(N)N1 JPJMLQRVGZBWPD-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 2
- PEUPUKDBCPLDIH-UHFFFAOYSA-N 1,2,4-triazole Chemical group C1=NC=N[N]1 PEUPUKDBCPLDIH-UHFFFAOYSA-N 0.000 claims description 2
- OGBOTYGRYZDLMG-UHFFFAOYSA-N 1-fluoroethanol Chemical compound CC(O)F OGBOTYGRYZDLMG-UHFFFAOYSA-N 0.000 claims description 2
- XNHNGYRHGMXUMT-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazol-5-amine Chemical compound NC1=CN=C(C(F)(F)F)N1 XNHNGYRHGMXUMT-UHFFFAOYSA-N 0.000 claims description 2
- WHCMFEVONKMBRP-UHFFFAOYSA-N 2-fluoro-2-hydroxypropanamide Chemical compound CC(O)(F)C(N)=O WHCMFEVONKMBRP-UHFFFAOYSA-N 0.000 claims description 2
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 claims description 2
- JQTMGOLZSBTZMS-UHFFFAOYSA-N 4-methylpiperazine-1-carbaldehyde Chemical compound CN1CCN(C=O)CC1 JQTMGOLZSBTZMS-UHFFFAOYSA-N 0.000 claims description 2
- NHKZYIMWHDQJLJ-UHFFFAOYSA-N 8-amino-3-[5-(3-amino-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl)-2-methylphenyl]-N-(2-hydroxy-2-methylpropyl)imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC1=C(C=C(C=C1)C(O)(C(N)=O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(=O)NCC(C)(C)O NHKZYIMWHDQJLJ-UHFFFAOYSA-N 0.000 claims description 2
- OTZYLQXEUUJHEZ-UHFFFAOYSA-N 8-amino-N-[(1-cyanocyclobutyl)methyl]-3-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(=O)NCC1(CCC1)C#N OTZYLQXEUUJHEZ-UHFFFAOYSA-N 0.000 claims description 2
- XHCVERLASWIGCB-UHFFFAOYSA-N 8-amino-N-methyl-3-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CNC(=O)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)(F)F XHCVERLASWIGCB-UHFFFAOYSA-N 0.000 claims description 2
- YSUYZIDWVGPTQS-UHFFFAOYSA-N CC1=NC=C(C2=NC(N)=CN2)O1 Chemical compound CC1=NC=C(C2=NC(N)=CN2)O1 YSUYZIDWVGPTQS-UHFFFAOYSA-N 0.000 claims description 2
- YPHFXUYWGMCMJJ-UHFFFAOYSA-N CN1N=CC=C1C1=NC(N)=CN1 Chemical compound CN1N=CC=C1C1=NC(N)=CN1 YPHFXUYWGMCMJJ-UHFFFAOYSA-N 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 17
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006721 (C5-C10) heteroaryl (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000002355 alkine group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- GILIYJDBJZWGBG-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-ol Chemical compound CC(O)C(F)(F)F GILIYJDBJZWGBG-UHFFFAOYSA-N 0.000 claims 1
- MZAFTZDOCPPASU-FIBGUPNXSA-N 2-[3-[8-amino-6-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-(trideuteriomethyl)phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=C3N(N=C1)CCC3)C(=CN=2)C=1C=C(C=CC=1C([2H])([2H])[2H])C(C(F)(F)F)(C)O MZAFTZDOCPPASU-FIBGUPNXSA-N 0.000 claims 1
- 125000000033 alkoxyamino group Chemical group 0.000 claims 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
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