KR20200066301A - Ire1 억제를 위한 화합물 및 조성물 - Google Patents

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Publication number

KR20200066301A

KR20200066301A KR1020207009201A KR20207009201A KR20200066301A KR 20200066301 A KR20200066301 A KR 20200066301A KR 1020207009201 A KR1020207009201 A KR 1020207009201A KR 20207009201 A KR20207009201 A KR 20207009201A KR 20200066301 A KR20200066301 A KR 20200066301A

Authority

KR

South Korea

Prior art keywords

amino

imidazo

naphthalen

cyclohex

pyrazin

Prior art date

2017-09-01

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.)

Ceased

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 245
• 102100030013 Endoribonuclease Human genes 0.000 title claims description 18
• 101001010783 Homo sapiens Endoribonuclease Proteins 0.000 title claims description 17
• 239000000203 mixture Substances 0.000 title abstract description 114
• 230000005764 inhibitory process Effects 0.000 title description 5
• 238000000034 method Methods 0.000 claims abstract description 116
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 109
• 201000010099 disease Diseases 0.000 claims abstract description 68
• 108091006081 Inositol-requiring enzyme-1 Proteins 0.000 claims abstract description 49
• 208000035475 disorder Diseases 0.000 claims abstract description 31
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 16
• 201000011510 cancer Diseases 0.000 claims abstract description 16
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
• 208000016192 Demyelinating disease Diseases 0.000 claims abstract description 14
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 13
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 13
• 206010016654 Fibrosis Diseases 0.000 claims abstract description 9
• 208000030533 eye disease Diseases 0.000 claims abstract description 9
• 206010012305 Demyelination Diseases 0.000 claims abstract description 6
• 230000004761 fibrosis Effects 0.000 claims abstract description 6
• -1 heteroalkenyl Chemical group 0.000 claims description 84
• 125000001424 substituent group Chemical group 0.000 claims description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims description 39
• 150000003839 salts Chemical class 0.000 claims description 32
• 230000000694 effects Effects 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000003107 substituted aryl group Chemical group 0.000 claims description 18
• 238000011282 treatment Methods 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 16
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 15
• 125000003367 polycyclic group Polymers 0.000 claims description 15
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
• 108010083644 Ribonucleases Proteins 0.000 claims description 14
• 102000006382 Ribonucleases Human genes 0.000 claims description 14
• 125000003566 oxetanyl group Chemical group 0.000 claims description 14
• XCGLILJUSGGSAC-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(3-methoxyphenyl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC=C1)OC)C(C)C XCGLILJUSGGSAC-UHFFFAOYSA-N 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 12
• PIPZGNNBWMTQRM-UHFFFAOYSA-N imidazo[1,5-a]pyrazine-5-carboxamide Chemical compound C=1N=CN2C=1C=NC=C2C(=O)N PIPZGNNBWMTQRM-UHFFFAOYSA-N 0.000 claims description 12
• 208000007014 Retinitis pigmentosa Diseases 0.000 claims description 11
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
• GOXNPDCKECLBLE-UHFFFAOYSA-N 1-[4-(1H-benzimidazol-2-ylmethyl)naphthalen-1-yl]-8-chloro-3-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazine Chemical compound N1C(=NC2=C1C=CC=C2)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2)Cl)CN1CCNCC1 GOXNPDCKECLBLE-UHFFFAOYSA-N 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• SUGVSVMHGSBVLO-UHFFFAOYSA-N N-[4-[8-amino-5-(piperazin-1-ylmethyl)-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-2-fluorophenyl]-1-(2-chlorophenyl)methanesulfonamide Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=CC(=C(C=C1)NS(=O)(=O)CC1=C(C=CC=C1)Cl)F)C(C)C SUGVSVMHGSBVLO-UHFFFAOYSA-N 0.000 claims description 8
• 108091000080 Phosphotransferase Proteins 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 230000003176 fibrotic effect Effects 0.000 claims description 8
• 102000020233 phosphotransferase Human genes 0.000 claims description 8
• AKIUKQGBBDWTNJ-UHFFFAOYSA-N 1-[4-[5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-phenylurea Chemical compound C(C)(C)C1=NC(=C2N1C(=CN=C2)C1=CCC(CC1)NC)C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC=CC=C1 AKIUKQGBBDWTNJ-UHFFFAOYSA-N 0.000 claims description 7
• YOJXTMKFMYASGR-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-phenylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC=CC=C1)C(C)C YOJXTMKFMYASGR-UHFFFAOYSA-N 0.000 claims description 7
• UVPJFALSFSKAPG-UHFFFAOYSA-N 5-[4-(methylamino)cyclohexen-1-yl]-1-[4-[(4-methyl-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound C(C)(C)C1=NC(=C2N1C(=CN=C2N)C1=CCC(CC1)NC)C1=CC=C(C2=CC=CC=C12)CC1=NC2=C(N1)C(=CC=C2)C UVPJFALSFSKAPG-UHFFFAOYSA-N 0.000 claims description 7
• PLBQDRPAJOSUPW-UHFFFAOYSA-N N-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-2-fluorophenyl]-1-(2-chlorophenyl)methanesulfonamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC(=C(C=C1)NS(=O)(=O)CC1=C(C=CC=C1)Cl)F)C(C)C PLBQDRPAJOSUPW-UHFFFAOYSA-N 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
• FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 6
• VZNMNKWJURWULV-UHFFFAOYSA-N 1-[4-(1H-benzimidazol-2-ylmethyl)naphthalen-1-yl]-8-chloro-3-[(4-methylpiperazin-1-yl)methyl]imidazo[1,5-a]pyrazine Chemical compound N1C(=NC2=C1C=CC=C2)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2)Cl)CN1CCN(CC1)C VZNMNKWJURWULV-UHFFFAOYSA-N 0.000 claims description 6
• LVGDTXGQDSYQOT-UHFFFAOYSA-N 1-[4-(8-amino-3-methyl-5-piperidin-3-ylimidazo[1,5-a]pyrazin-1-yl)naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1CNCCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C LVGDTXGQDSYQOT-UHFFFAOYSA-N 0.000 claims description 6
• TWLIWFJCVUKGQH-UHFFFAOYSA-N 1-[4-[5-(1-acetyl-3,6-dihydro-2H-pyridin-5-yl)-8-amino-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C(C)(=O)N1CC(=CCC1)C1=CN=C(C=2N1C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C)N TWLIWFJCVUKGQH-UHFFFAOYSA-N 0.000 claims description 6
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 6
• 241001279686 Allium moly Species 0.000 claims description 6
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 6
• 208000002780 macular degeneration Diseases 0.000 claims description 6
• 238000006384 oligomerization reaction Methods 0.000 claims description 6
• 201000007737 Retinal degeneration Diseases 0.000 claims description 5
• 201000010802 Wolfram syndrome Diseases 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 150000004820 halides Chemical class 0.000 claims description 5
• 230000004258 retinal degeneration Effects 0.000 claims description 5
• WDZRGHMZUWLJRS-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(piperazine-1-carbonyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C(=O)N1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C WDZRGHMZUWLJRS-UHFFFAOYSA-N 0.000 claims description 4
• QTVJLMNBIFQNGX-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3,5-difluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC(=CC(=C1)F)F)C(C)C QTVJLMNBIFQNGX-UHFFFAOYSA-N 0.000 claims description 4
• CYFPHYADTCYQOF-UHFFFAOYSA-N 5-[4-(methylamino)cyclohexen-1-yl]-1-[4-[(5-phenyl-1H-imidazol-2-yl)methyl]naphthalen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound C(C)(C)C1=NC(=C2N1C(=CN=C2N)C1=CCC(CC1)NC)C1=CC=C(C2=CC=CC=C12)CC=1NC(=CN=1)C1=CC=CC=C1 CYFPHYADTCYQOF-UHFFFAOYSA-N 0.000 claims description 4
• 230000030833 cell death Effects 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 claims description 3
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 claims description 3
• UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 claims description 3
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 claims description 3
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 claims description 3
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 claims description 3
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 claims description 3
• GLTCMSQLCBGUHO-UHFFFAOYSA-N 1-[4-(1H-benzimidazol-2-ylmethyl)-2-fluorophenyl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound N1C(=NC2=C1C=CC=C2)CC1=CC(=C(C=C1)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C)F GLTCMSQLCBGUHO-UHFFFAOYSA-N 0.000 claims description 3
• SXFNTSUXMMJUCY-UHFFFAOYSA-N 1-[4-(1H-benzimidazol-2-ylmethyl)naphthalen-1-yl]-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-8-amine Chemical compound N1C(=NC2=C1C=CC=C2)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C SXFNTSUXMMJUCY-UHFFFAOYSA-N 0.000 claims description 3
• SRRABQMVECDYIB-UHFFFAOYSA-N 1-[4-(1H-benzimidazol-2-ylmethyl)naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound N1C(=NC2=C1C=CC=C2)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C SRRABQMVECDYIB-UHFFFAOYSA-N 0.000 claims description 3
• NRRMVPUJAOSVOS-UHFFFAOYSA-N 1-[4-(3H-imidazo[4,5-c]pyridin-2-ylmethyl)naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound N1C(=NC=2C=NC=CC=21)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C NRRMVPUJAOSVOS-UHFFFAOYSA-N 0.000 claims description 3
• NIQHPWXUQZVDCN-UHFFFAOYSA-N 1-[4-(8-amino-3-methyl-5-pyridin-3-ylimidazo[1,5-a]pyrazin-1-yl)naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C=1C=NC=CC=1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C NIQHPWXUQZVDCN-UHFFFAOYSA-N 0.000 claims description 3
• JZLOMDDZYOMQFD-UHFFFAOYSA-N 1-[4-[(4,6-difluoro-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound FC1=CC(=CC=2NC(=NC=21)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C)F JZLOMDDZYOMQFD-UHFFFAOYSA-N 0.000 claims description 3
• FNMGYSCBFDCYQM-UHFFFAOYSA-N 1-[4-[(4,6-dimethyl-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound CC1=CC(=CC=2NC(=NC=21)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C)C FNMGYSCBFDCYQM-UHFFFAOYSA-N 0.000 claims description 3
• LHLLEKKPPFDWSJ-UHFFFAOYSA-N 1-[4-[(4-chloro-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound ClC1=CC=CC2=C1NC(=N2)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C LHLLEKKPPFDWSJ-UHFFFAOYSA-N 0.000 claims description 3
• OZXJQTQMPKEXOL-UHFFFAOYSA-N 1-[4-[(4-fluoro-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound FC1=CC=CC2=C1NC(=N2)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C OZXJQTQMPKEXOL-UHFFFAOYSA-N 0.000 claims description 3
• FRKRNSDOTOJNKA-UHFFFAOYSA-N 1-[4-[(4-methyl-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-3-propan-2-yl-5-[4-(2,2,2-trifluoroethylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-8-amine Chemical compound CC1=CC=CC=2NC(=NC=21)CC1=CC=C(C2=CC=CC=C12)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NCC(F)(F)F)N)C(C)C FRKRNSDOTOJNKA-UHFFFAOYSA-N 0.000 claims description 3
• XYNJILQMFRDGFL-UHFFFAOYSA-N 1-[4-[(4-methyl-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-5-[4-[methyl(2,2,2-trifluoroethyl)amino]cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound CN(C1CC=C(CC1)C1=CN=C(C=2N1C(=NC=2C1=CC=C(C2=CC=CC=C12)CC1=NC2=C(N1)C=CC=C2C)C(C)C)N)CC(F)(F)F XYNJILQMFRDGFL-UHFFFAOYSA-N 0.000 claims description 3
• ULSDLOGTKAFQBB-UHFFFAOYSA-N 1-[4-[(4-methyl-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-5-[4-[methyl(3,3,3-trifluoropropyl)amino]cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound CN(C1CC=C(CC1)C1=CN=C(C=2N1C(=NC=2C1=CC=C(C2=CC=CC=C12)CC1=NC2=C(N1)C=CC=C2C)C(C)C)N)CCC(F)(F)F ULSDLOGTKAFQBB-UHFFFAOYSA-N 0.000 claims description 3
• BWUYFXGEPUJPJU-UHFFFAOYSA-N 1-[4-[(6-methoxy-1H-benzimidazol-2-yl)methyl]naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound C(C)(C)C1=NC(=C2N1C(=CN=C2N)C1=CCC(CC1)NC)C1=CC=C(C2=CC=CC=C12)CC1=NC2=C(N1)C=CC(=C2)OC BWUYFXGEPUJPJU-UHFFFAOYSA-N 0.000 claims description 3
• OYQOGBONRWHXTQ-UHFFFAOYSA-N 1-[4-[5-(1-acetyl-3,6-dihydro-2H-pyridin-4-yl)-8-amino-3-methylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C(C)(=O)N1CCC(=CC1)C1=CN=C(C=2N1C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)F)C)N OYQOGBONRWHXTQ-UHFFFAOYSA-N 0.000 claims description 3
• KYPMSEFJPMAYDX-UHFFFAOYSA-N 1-[4-[5-(1-acetylpiperidin-3-yl)-8-amino-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C(C)(=O)N1CC(CCC1)C1=CN=C(C=2N1C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C)N KYPMSEFJPMAYDX-UHFFFAOYSA-N 0.000 claims description 3
• KWPBSHNSZFVEFB-UHFFFAOYSA-N 1-[4-[5-(2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-ylmethyl)-8-amino-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CC3CNCC3C1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C KWPBSHNSZFVEFB-UHFFFAOYSA-N 0.000 claims description 3
• IPJBOCDOZIARSA-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)F)CC IPJBOCDOZIARSA-UHFFFAOYSA-N 0.000 claims description 3
• ZVKGAJPPPAGZGO-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)CC ZVKGAJPPPAGZGO-UHFFFAOYSA-N 0.000 claims description 3
• DNFRVVSPFBTBII-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-[(4-methylpiperazin-1-yl)methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCN(CC1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)CC DNFRVVSPFBTBII-UHFFFAOYSA-N 0.000 claims description 3
• XNIWEMDQSZRIIR-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC1=CC(=CC=C1)F)F)CC XNIWEMDQSZRIIR-UHFFFAOYSA-N 0.000 claims description 3
• DVDXHZKPVLULQW-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)F)CC DVDXHZKPVLULQW-UHFFFAOYSA-N 0.000 claims description 3
• KOZDZIFVGMKULO-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)F)=O)CC KOZDZIFVGMKULO-UHFFFAOYSA-N 0.000 claims description 3
• FQTOCKAIODUUME-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-methylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C)=O)CC FQTOCKAIODUUME-UHFFFAOYSA-N 0.000 claims description 3
• HPBRSBWJGIOGNO-UHFFFAOYSA-N 1-[4-[8-amino-3-ethyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)CC HPBRSBWJGIOGNO-UHFFFAOYSA-N 0.000 claims description 3
• JTGFPRPNAAELRQ-LJQANCHMSA-N 1-[4-[8-amino-3-ethyl-5-[[(3R)-3-methylpiperazin-1-yl]methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C[C@H](NCC1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)CC JTGFPRPNAAELRQ-LJQANCHMSA-N 0.000 claims description 3
• JTGFPRPNAAELRQ-IBGZPJMESA-N 1-[4-[8-amino-3-ethyl-5-[[(3S)-3-methylpiperazin-1-yl]methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C[C@@H](NCC1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)CC JTGFPRPNAAELRQ-IBGZPJMESA-N 0.000 claims description 3
• HRRPZWXIEPMACD-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(1,2,3,4-tetrahydroisoquinolin-5-yl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=C3CCNCC3=CC=C1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C HRRPZWXIEPMACD-UHFFFAOYSA-N 0.000 claims description 3
• ZFURNAQAXALOCT-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C=1CCN(CC=1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C ZFURNAQAXALOCT-UHFFFAOYSA-N 0.000 claims description 3
• QNNZYNSUOIUIFN-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(1-methylpyrazol-4-yl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C=1C=NN(C=1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C QNNZYNSUOIUIFN-UHFFFAOYSA-N 0.000 claims description 3
• ANKVTUAGTWWNLA-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(1-piperidin-4-ylpyrazol-4-yl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C=1C=NN(C=1)C1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C ANKVTUAGTWWNLA-UHFFFAOYSA-N 0.000 claims description 3
• NXCWZROWYWZELZ-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(4-methylpiperazine-1-carbonyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C(=O)N1CCN(CC1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C NXCWZROWYWZELZ-UHFFFAOYSA-N 0.000 claims description 3
• UUJREGOHEWFPMD-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)F)C UUJREGOHEWFPMD-UHFFFAOYSA-N 0.000 claims description 3
• FCGADVOFQWXXDV-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)F)=O)C FCGADVOFQWXXDV-UHFFFAOYSA-N 0.000 claims description 3
• VDONLJSVWKVIMK-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-methylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C)=O)C VDONLJSVWKVIMK-UHFFFAOYSA-N 0.000 claims description 3
• ZODPKYJGQAWHIP-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C ZODPKYJGQAWHIP-UHFFFAOYSA-N 0.000 claims description 3
• XUNNDTLFQHLTJV-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(piperidin-4-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CC1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C XUNNDTLFQHLTJV-UHFFFAOYSA-N 0.000 claims description 3
• ZSTCSQGAXLEGAO-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[(4-methylpiperazin-1-yl)methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCN(CC1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C ZSTCSQGAXLEGAO-UHFFFAOYSA-N 0.000 claims description 3
• LTTVSTJARKYOOL-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[(piperidin-3-ylamino)methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CNC1CNCCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C LTTVSTJARKYOOL-UHFFFAOYSA-N 0.000 claims description 3
• LKGARWHJVRGERF-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[(piperidin-4-ylamino)methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CNC1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C LKGARWHJVRGERF-UHFFFAOYSA-N 0.000 claims description 3
• ZIBOAJZOVXTVQQ-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-2-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC(=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C)C ZIBOAJZOVXTVQQ-UHFFFAOYSA-N 0.000 claims description 3
• PAUREOJGVUDTRL-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)F)C PAUREOJGVUDTRL-UHFFFAOYSA-N 0.000 claims description 3
• HXTXSPIAZIURFL-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-3-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C)C HXTXSPIAZIURFL-UHFFFAOYSA-N 0.000 claims description 3
• LFDLJFJGADOPQS-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-5-fluoro-2-methoxyphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC(=C(C=C1F)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)OC)C LFDLJFJGADOPQS-UHFFFAOYSA-N 0.000 claims description 3
• QXKHDLCKSVAWOL-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-5-fluoro-2-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC(=C(C=C1F)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C)C QXKHDLCKSVAWOL-UHFFFAOYSA-N 0.000 claims description 3
• MUMZBUJYFOTJTI-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)F)=O)C MUMZBUJYFOTJTI-UHFFFAOYSA-N 0.000 claims description 3
• PZOKCVOCAMNHIQ-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-methylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C)=O)C PZOKCVOCAMNHIQ-UHFFFAOYSA-N 0.000 claims description 3
• CKXWEYFPOWJMQM-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C CKXWEYFPOWJMQM-UHFFFAOYSA-N 0.000 claims description 3
• OZRAPVMRCFUTCJ-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-pyridin-3-ylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC=1C=NC=CC=1)C OZRAPVMRCFUTCJ-UHFFFAOYSA-N 0.000 claims description 3
• MBWFEFUZDQYGFQ-GOSISDBHSA-N 1-[4-[8-amino-3-methyl-5-[[(3R)-3-methylpiperazin-1-yl]methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C[C@H](NCC1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C MBWFEFUZDQYGFQ-GOSISDBHSA-N 0.000 claims description 3
• MBWFEFUZDQYGFQ-SFHVURJKSA-N 1-[4-[8-amino-3-methyl-5-[[(3S)-3-methylpiperazin-1-yl]methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C[C@@H](NCC1)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C MBWFEFUZDQYGFQ-SFHVURJKSA-N 0.000 claims description 3
• SMNHYPALLHZZQE-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-[[4-(methylamino)piperidin-1-yl]methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C SMNHYPALLHZZQE-UHFFFAOYSA-N 0.000 claims description 3
• LTTVSTJARKYOOL-NRFANRHFSA-N 1-[4-[8-amino-3-methyl-5-[[[(3S)-piperidin-3-yl]amino]methyl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN[C@@H]1CNCCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C LTTVSTJARKYOOL-NRFANRHFSA-N 0.000 claims description 3
• WASGVADIUZMBBV-UHFFFAOYSA-N 1-[4-[8-amino-5-(1,4-diazepan-1-ylmethyl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C WASGVADIUZMBBV-UHFFFAOYSA-N 0.000 claims description 3
• DSRZOZWYHBSVLG-UHFFFAOYSA-N 1-[4-[8-amino-5-(2,5-diazabicyclo[2.2.1]heptan-2-ylmethyl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C3CNC(C1)C3)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C DSRZOZWYHBSVLG-UHFFFAOYSA-N 0.000 claims description 3
• MHYKQMNNONRDRF-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-ethylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC(=CC=C1)C(F)(F)F)CC MHYKQMNNONRDRF-UHFFFAOYSA-N 0.000 claims description 3
• UNUNCGCBMHUSPI-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-(2,3-dihydro-1,4-benzodioxin-6-yl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC2=C(OCCO2)C=C1)=O)F)C UNUNCGCBMHUSPI-UHFFFAOYSA-N 0.000 claims description 3
• ZJKUMUHZJMQYEY-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC1=CC=C(C=C1)CN1CCN(CC1)C)F)C ZJKUMUHZJMQYEY-UHFFFAOYSA-N 0.000 claims description 3
• YEGWVTBZAJAORW-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(2,3-dihydro-1,4-benzodioxin-6-yl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC2=C(OCCO2)C=C1)=O)C YEGWVTBZAJAORW-UHFFFAOYSA-N 0.000 claims description 3
• IOENQKLMEXPVJZ-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(2-methoxy-5-methylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=C(C=CC(=C1)C)OC)C IOENQKLMEXPVJZ-UHFFFAOYSA-N 0.000 claims description 3
• ADUWVRJNPXTLAA-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(2-methoxyphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=C(C=CC=C1)OC)C ADUWVRJNPXTLAA-UHFFFAOYSA-N 0.000 claims description 3
• SFPSABBUJAJXLG-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3,5-dimethylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC(=C1)C)C)=O)C SFPSABBUJAJXLG-UHFFFAOYSA-N 0.000 claims description 3
• UVPHVRIJYTUQCI-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)F)=O)C UVPHVRIJYTUQCI-UHFFFAOYSA-N 0.000 claims description 3
• CWDSQTHRDMHNPZ-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-methylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC=1C=C(C=CC=1)C)C CWDSQTHRDMHNPZ-UHFFFAOYSA-N 0.000 claims description 3
• ZXLFCFXCJBSDOV-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(5-chloro-2-methoxyphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=C(C=CC(=C1)Cl)OC)C ZXLFCFXCJBSDOV-UHFFFAOYSA-N 0.000 claims description 3
• ZERZRGVWSGLHRN-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(5-chloro-2-methylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=C(C=CC(=C1)Cl)C)=O)C ZERZRGVWSGLHRN-UHFFFAOYSA-N 0.000 claims description 3
• WLMRCGABELMEKQ-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[(4-methylphenyl)methyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NCC1=CC=C(C=C1)C)=O)C WLMRCGABELMEKQ-UHFFFAOYSA-N 0.000 claims description 3
• LMMQUUMPBIBJPD-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[2-chloro-5-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=C(C=CC(=C1)C(F)(F)F)Cl)C LMMQUUMPBIBJPD-UHFFFAOYSA-N 0.000 claims description 3
• MHVACDRHZSFNEI-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3,5-bis(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O)C MHVACDRHZSFNEI-UHFFFAOYSA-N 0.000 claims description 3
• IMSHPVSITKHVLB-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C IMSHPVSITKHVLB-UHFFFAOYSA-N 0.000 claims description 3
• LMKKBMRRKFUXSK-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC=C(C=C1)C(F)(F)F)=O)C LMKKBMRRKFUXSK-UHFFFAOYSA-N 0.000 claims description 3
• HSJWZAMYDWDTNG-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC=C(C=C1)CN1CCN(CC1)C)C HSJWZAMYDWDTNG-UHFFFAOYSA-N 0.000 claims description 3
• JXNJOPHECMWGBM-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=C(C=C1)Cl)C(F)(F)F)=O)C JXNJOPHECMWGBM-UHFFFAOYSA-N 0.000 claims description 3
• KBGSWPIMJIIUJE-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-benzylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NCC1=CC=CC=C1)C KBGSWPIMJIIUJE-UHFFFAOYSA-N 0.000 claims description 3
• MALUEWZRJZEUJK-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-phenylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC=CC=C1)C MALUEWZRJZEUJK-UHFFFAOYSA-N 0.000 claims description 3
• CSXBVPDMWWUHFM-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C(C)C CSXBVPDMWWUHFM-UHFFFAOYSA-N 0.000 claims description 3
• QWKZYTDZHXSAQH-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminophenyl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CC=C(C=C1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C QWKZYTDZHXSAQH-UHFFFAOYSA-N 0.000 claims description 3
• USYOWXXQKSEBGR-UHFFFAOYSA-N 1-[4-[8-amino-5-(4-aminopiperidine-1-carbonyl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C(=O)N1CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C USYOWXXQKSEBGR-UHFFFAOYSA-N 0.000 claims description 3
• MBMITYAMSGROJI-UHFFFAOYSA-N 1-[4-[8-amino-5-(cyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCCCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C MBMITYAMSGROJI-UHFFFAOYSA-N 0.000 claims description 3
• LEHCNANJAZYJNY-UHFFFAOYSA-N 1-[4-[8-amino-5-(piperazin-1-ylmethyl)-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C(C)C LEHCNANJAZYJNY-UHFFFAOYSA-N 0.000 claims description 3
• VKXZONBFMVCVLL-LJQANCHMSA-N 1-[4-[8-amino-5-[(3R)-3-aminopiperidine-1-carbonyl]-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C(=O)N1C[C@@H](CCC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C VKXZONBFMVCVLL-LJQANCHMSA-N 0.000 claims description 3
• VKXZONBFMVCVLL-IBGZPJMESA-N 1-[4-[8-amino-5-[(3S)-3-aminopiperidine-1-carbonyl]-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C(=O)N1C[C@H](CCC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C VKXZONBFMVCVLL-IBGZPJMESA-N 0.000 claims description 3
• KBKNGSDUNGMGJP-UHFFFAOYSA-N 1-[4-[8-amino-5-[(4-aminopiperidin-1-yl)methyl]-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C KBKNGSDUNGMGJP-UHFFFAOYSA-N 0.000 claims description 3
• KNCCJMMSBANWFG-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-2-fluorophenyl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC(=C(C=C1)NC(=O)NC1=CC(=CC=C1)F)F)C(C)C KNCCJMMSBANWFG-UHFFFAOYSA-N 0.000 claims description 3
• HCKXTXMXJRXZSM-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-2-fluorophenyl]-3-phenylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC(=C(C=C1)NC(=O)NC1=CC=CC=C1)F)C(C)C HCKXTXMXJRXZSM-UHFFFAOYSA-N 0.000 claims description 3
• PXVRREAGRSPKPS-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-chlorophenyl]-3-pyridin-3-ylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC=1C=NC=CC=1)Cl)C(C)C PXVRREAGRSPKPS-UHFFFAOYSA-N 0.000 claims description 3
• JSFVJRSZTZFNEE-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-(2,3-dihydro-1,4-benzodioxin-6-yl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC1=CC2=C(OCCO2)C=C1)F)C(C)C JSFVJRSZTZFNEE-UHFFFAOYSA-N 0.000 claims description 3
• JEJXEKXAZOJFSL-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-(3-fluoro-5-methoxyphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC1=CC(=CC(=C1)OC)F)F)C(C)C JEJXEKXAZOJFSL-UHFFFAOYSA-N 0.000 claims description 3
• JUSAVWDSNPWHBF-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC1=CC(=CC=C1)F)F)C(C)C JUSAVWDSNPWHBF-UHFFFAOYSA-N 0.000 claims description 3
• VTFWNOIPOXHYJF-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-(5-fluoropyridin-3-yl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC=1C=NC=C(C=1)F)F)C(C)C VTFWNOIPOXHYJF-UHFFFAOYSA-N 0.000 claims description 3
• JQDIKGWPCZWQHV-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-(5-methoxypyridin-3-yl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC=1C=NC=C(C=1)OC)F)C(C)C JQDIKGWPCZWQHV-UHFFFAOYSA-N 0.000 claims description 3
• FDWYKFDNIQPRFI-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)F)C(C)C FDWYKFDNIQPRFI-UHFFFAOYSA-N 0.000 claims description 3
• RNAICNOVVILUSS-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-phenylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC1=CC=CC=C1)F)C(C)C RNAICNOVVILUSS-UHFFFAOYSA-N 0.000 claims description 3
• ZXYFPYKTOVYMEP-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-3-pyridin-3-ylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC=1C=NC=CC=1)F)C(C)C ZXYFPYKTOVYMEP-UHFFFAOYSA-N 0.000 claims description 3
• QKMUFGGUCSPCIQ-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-methoxyphenyl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC1=CC(=CC=C1)F)OC)C(C)C QKMUFGGUCSPCIQ-UHFFFAOYSA-N 0.000 claims description 3
• VQVLEINQEYYNJO-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-methylphenyl]-3-pyridin-3-ylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)NC(=O)NC=1C=NC=CC=1)C)C(C)C VQVLEINQEYYNJO-UHFFFAOYSA-N 0.000 claims description 3
• KXLBOINXQMDOCA-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(2,3-dihydro-1,4-benzodioxin-6-yl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC2=C(OCCO2)C=C1)C(C)C KXLBOINXQMDOCA-UHFFFAOYSA-N 0.000 claims description 3
• AIOYHZXWPWKQDW-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(2-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=C(C=CC=C1)F)C(C)C AIOYHZXWPWKQDW-UHFFFAOYSA-N 0.000 claims description 3
• NGUXTMRTIKTOCZ-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3,4-dimethoxyphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC(=C(C=C1)OC)OC)C(C)C NGUXTMRTIKTOCZ-UHFFFAOYSA-N 0.000 claims description 3
• FSLDTIHDYNNBHQ-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-cyano-5-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC(=CC(=C1)F)C#N)C(C)C FSLDTIHDYNNBHQ-UHFFFAOYSA-N 0.000 claims description 3
• YYWWZODVNBBYFO-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)F)=O)C(C)C YYWWZODVNBBYFO-UHFFFAOYSA-N 0.000 claims description 3
• WWSCYSSYAAMTRG-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-methoxyphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC(=CC=C1)OC)C(C)C WWSCYSSYAAMTRG-UHFFFAOYSA-N 0.000 claims description 3
• XJIBAVMEPJKYBD-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-methylphenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C)=O)C(C)C XJIBAVMEPJKYBD-UHFFFAOYSA-N 0.000 claims description 3
• JURKNUVTUJEZMU-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(4-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC=C(C=C1)F)C(C)C JURKNUVTUJEZMU-UHFFFAOYSA-N 0.000 claims description 3
• YAGVYADQJAEFLI-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=CC(=CC=C1)C(F)(F)F)C(C)C YAGVYADQJAEFLI-UHFFFAOYSA-N 0.000 claims description 3
• VDENAHFOZUGQBO-UHFFFAOYSA-N 1-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]phenyl]-3-pyridin-3-ylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C=C1)NC(=O)NC=1C=NC=CC=1)C(C)C VDENAHFOZUGQBO-UHFFFAOYSA-N 0.000 claims description 3
• OSRLERBWFHAONJ-HXUWFJFHSA-N 1-[4-[8-amino-5-[[(3R)-3-aminopiperidin-1-yl]methyl]-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C[C@@H](CCC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C OSRLERBWFHAONJ-HXUWFJFHSA-N 0.000 claims description 3
• BYUUMAIPMPKMNW-KDURUIRLSA-N 1-[4-[8-amino-5-[[(3R,5S)-3,5-dimethylpiperazin-1-yl]methyl]-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C[C@H](N[C@H](C1)C)C)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C BYUUMAIPMPKMNW-KDURUIRLSA-N 0.000 claims description 3
• OSRLERBWFHAONJ-FQEVSTJZSA-N 1-[4-[8-amino-5-[[(3S)-3-aminopiperidin-1-yl]methyl]-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)CN1C[C@H](CCC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C OSRLERBWFHAONJ-FQEVSTJZSA-N 0.000 claims description 3
• CUIMGTAZDQFHOO-UHFFFAOYSA-N 1-[5-(1H-benzimidazol-2-ylmethyl)naphthalen-1-yl]-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-8-amine Chemical compound N1C(=NC2=C1C=CC=C2)CC1=C2C=CC=C(C2=CC=C1)C=1N=C(N2C=1C(=NC=C2C1=CCC(CC1)NC)N)C(C)C CUIMGTAZDQFHOO-UHFFFAOYSA-N 0.000 claims description 3
• VRLZKOZEYYLJRT-UHFFFAOYSA-N 1-[5-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]isoquinolin-8-yl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C2C=CN=CC2=C(C=C1)NC(=O)NC1=CC(=CC=C1)F)C(C)C VRLZKOZEYYLJRT-UHFFFAOYSA-N 0.000 claims description 3
• ATNLCTJLIKBARM-UHFFFAOYSA-N 1-[5-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(2,3-dihydro-1,4-benzodioxin-6-yl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C2C=CC=C(C2=CC=C1)NC(=O)NC1=CC2=C(OCCO2)C=C1)C(C)C ATNLCTJLIKBARM-UHFFFAOYSA-N 0.000 claims description 3
• NNQVPNHOOURITM-UHFFFAOYSA-N 1-[5-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-(3-fluorophenyl)urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C2C=CC=C(C2=CC=C1)NC(=O)NC1=CC(=CC=C1)F)C(C)C NNQVPNHOOURITM-UHFFFAOYSA-N 0.000 claims description 3
• SAIOOAGKPSXHNE-UHFFFAOYSA-N 1-[5-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C2C=CC=C(C2=CC=C1)NC(=O)NC1=CC(=CC=C1)C(F)(F)F)C(C)C SAIOOAGKPSXHNE-UHFFFAOYSA-N 0.000 claims description 3
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• RWUZAZWHNRAZLV-UHFFFAOYSA-N 2-[4-[8-amino-3-ethyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC=C1)C(F)(F)F)CC RWUZAZWHNRAZLV-UHFFFAOYSA-N 0.000 claims description 3
• VQYWQEDWEUAPFM-UHFFFAOYSA-N 2-[4-[8-amino-3-methyl-5-(piperazin-1-ylmethyl)imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide Chemical compound NC=1C=2N(C(=CN=1)CN1CCNCC1)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC=C1)C(F)(F)F)C VQYWQEDWEUAPFM-UHFFFAOYSA-N 0.000 claims description 3
• VAKXBKYUCQOPJZ-UHFFFAOYSA-N 2-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-N-[3-(trifluoromethyl)phenyl]acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C(F)(F)F)F)C VAKXBKYUCQOPJZ-UHFFFAOYSA-N 0.000 claims description 3
• OBJCGDJLRFPIOQ-UHFFFAOYSA-N 2-[4-[8-amino-3-methyl-5-[4-(methylamino)cyclohexen-1-yl]imidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC=C1)C(F)(F)F)C OBJCGDJLRFPIOQ-UHFFFAOYSA-N 0.000 claims description 3
• DQQRHCULUALFIP-UHFFFAOYSA-N 2-[4-[8-amino-5-(4-aminocyclohexen-1-yl)-3-methylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)N)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC=C1)C(F)(F)F)C DQQRHCULUALFIP-UHFFFAOYSA-N 0.000 claims description 3
• CXZIJXALYICZNC-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-N-(3-fluorophenyl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)F)F)C(C)C CXZIJXALYICZNC-UHFFFAOYSA-N 0.000 claims description 3
• ODGHFNABHVKIJO-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-3-fluorophenyl]-N-phenylacetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C(C=C(C=C1)CC(=O)NC1=CC=CC=C1)F)C(C)C ODGHFNABHVKIJO-UHFFFAOYSA-N 0.000 claims description 3
• RFMHITGLCRDWQJ-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(1,3-thiazol-5-yl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CN=CS1)C(C)C RFMHITGLCRDWQJ-UHFFFAOYSA-N 0.000 claims description 3
• GKYDSLLYJAADMU-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(1-methylbenzimidazol-5-yl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC2=C(N(C=N2)C)C=C1)C(C)C GKYDSLLYJAADMU-UHFFFAOYSA-N 0.000 claims description 3
• BNWJWKNWUCOZBM-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(1-methylpyrazol-4-yl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC=1C=NN(C=1)C)C(C)C BNWJWKNWUCOZBM-UHFFFAOYSA-N 0.000 claims description 3
• TWMGPGSKVFCQJF-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(2,2-difluoro-1,3-benzodioxol-5-yl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC2=C(OC(O2)(F)F)C=C1)C(C)C TWMGPGSKVFCQJF-UHFFFAOYSA-N 0.000 claims description 3
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• JNRWLYJSZNIGLA-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(3-cyano-5-fluorophenyl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC(=C1)F)C#N)C(C)C JNRWLYJSZNIGLA-UHFFFAOYSA-N 0.000 claims description 3
• XNQRQAHGKLVZEO-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(3-cyanophenyl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC=C1)C#N)C(C)C XNQRQAHGKLVZEO-UHFFFAOYSA-N 0.000 claims description 3
• HGUSWBFJIVMMRO-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(3-fluoro-5-methoxyphenyl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC(=C1)OC)F)C(C)C HGUSWBFJIVMMRO-UHFFFAOYSA-N 0.000 claims description 3
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• DZERNABSKMAXJO-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(5-fluoropyridin-3-yl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC=1C=NC=C(C=1)F)C(C)C DZERNABSKMAXJO-UHFFFAOYSA-N 0.000 claims description 3
• HYCTXLJAXIFQEM-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-(5-methoxypyridin-3-yl)acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC=1C=NC=C(C=1)OC)C(C)C HYCTXLJAXIFQEM-UHFFFAOYSA-N 0.000 claims description 3
• ZNANREGWTCXPMM-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=CC(=CC=C1)C(F)(F)F)C(C)C ZNANREGWTCXPMM-UHFFFAOYSA-N 0.000 claims description 3
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• JQRJUBNWKNMKFB-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-pyridin-2-ylacetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC1=NC=CC=C1)C(C)C JQRJUBNWKNMKFB-UHFFFAOYSA-N 0.000 claims description 3
• SKINCJICSKUQNF-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-pyridin-3-ylacetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC=1C=NC=CC=1)C(C)C SKINCJICSKUQNF-UHFFFAOYSA-N 0.000 claims description 3
• XZYAGONJQVJGNE-UHFFFAOYSA-N 2-[4-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-pyrimidin-5-ylacetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)CC(=O)NC=1C=NC=NC=1)C(C)C XZYAGONJQVJGNE-UHFFFAOYSA-N 0.000 claims description 3
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