BR112020004226A2 - compostos e composições para inibição de ire1 - Google Patents

Info

Publication number

BR112020004226A2

BR112020004226A2 BR112020004226-9A BR112020004226A BR112020004226A2 BR 112020004226 A2 BR112020004226 A2 BR 112020004226A2 BR 112020004226 A BR112020004226 A BR 112020004226A BR 112020004226 A2 BR112020004226 A2 BR 112020004226A2

Authority

BR

Brazil

Prior art keywords

amino

pyrazin

imidazo

naphthalen

cyclohex

Prior art date

2017-09-01

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 251
• 239000000203 mixture Substances 0.000 title abstract description 123
• 230000005764 inhibitory process Effects 0.000 title description 7
• 101100452784 Caenorhabditis elegans ire-1 gene Proteins 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 111
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 84
• 201000010099 disease Diseases 0.000 claims abstract description 56
• 208000035475 disorder Diseases 0.000 claims abstract description 27
• 102100030013 Endoribonuclease Human genes 0.000 claims abstract description 18
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 13
• 208000016192 Demyelinating disease Diseases 0.000 claims abstract description 12
• 201000011510 cancer Diseases 0.000 claims abstract description 12
• 208000030533 eye disease Diseases 0.000 claims abstract description 11
• 230000003176 fibrotic effect Effects 0.000 claims abstract description 11
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 11
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 11
• -1 -OH Chemical group 0.000 claims description 560
• 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 255
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 232
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 81
• 108091006081 Inositol-requiring enzyme-1 Proteins 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000000623 heterocyclic group Chemical group 0.000 claims description 32
• 230000000694 effects Effects 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
• 125000003107 substituted aryl group Chemical group 0.000 claims description 19
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 17
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
• 101001010783 Homo sapiens Endoribonuclease Proteins 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
• 239000012453 solvate Substances 0.000 claims description 15
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 108010083644 Ribonucleases Proteins 0.000 claims description 13
• 102000006382 Ribonucleases Human genes 0.000 claims description 13
• 230000006907 apoptotic process Effects 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 238000011282 treatment Methods 0.000 claims description 13
• 208000007014 Retinitis pigmentosa Diseases 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 125000003566 oxetanyl group Chemical group 0.000 claims description 10
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• 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 6
• 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 6
• 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 6
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 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
• 108091000080 Phosphotransferase Proteins 0.000 claims description 6
• 201000007737 Retinal degeneration Diseases 0.000 claims description 6
• 201000010802 Wolfram syndrome Diseases 0.000 claims description 6
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 6
• 150000004820 halides Chemical group 0.000 claims description 6
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
• SMKLPBPDGBAFRQ-UHFFFAOYSA-N imidazo[1,5-a]pyrazin-8-amine Chemical compound NC1=NC=CN2C=NC=C12 SMKLPBPDGBAFRQ-UHFFFAOYSA-N 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
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 102000020233 phosphotransferase Human genes 0.000 claims description 6
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
• 125000003367 polycyclic group Chemical group 0.000 claims description 6
• 230000004258 retinal degeneration Effects 0.000 claims description 6
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 5
• 238000006384 oligomerization reaction Methods 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
• 206010016654 Fibrosis Diseases 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 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
• 125000006273 (C1-C3) alkyl group Chemical group 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
• FJKKVYZQHKFJHJ-UHFFFAOYSA-N 1-[4-[8-amino-3-methyl-5-(1,2,3,6-tetrahydropyridin-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)C=1CNCCC=1)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C FJKKVYZQHKFJHJ-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
• 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
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 claims description 3
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 claims description 3
• YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 claims description 3
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 claims description 3
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 claims description 3
• VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 claims description 3
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 claims description 3
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 claims description 3
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 claims description 3
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 claims description 3
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 claims description 3
• ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 claims description 3
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• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
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• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 3
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• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 claims description 3
• LUIJNVAPJDNBKC-UHFFFAOYSA-N N-[4-[8-amino-5-[4-(2-fluoroethylamino)cyclohexen-1-yl]-3-methylimidazo[1,5-a]pyrazin-1-yl]-2-fluorophenyl]-2-chlorobenzenesulfonamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NCCF)C(=NC=2C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C=CC=C1)Cl)F)C LUIJNVAPJDNBKC-UHFFFAOYSA-N 0.000 claims description 3
• HYAIIJGDJZURIH-UHFFFAOYSA-N N-[4-[8-amino-5-[4-(2-fluoroethylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-2-fluorophenyl]-2-fluorobenzenesulfonamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NCCF)C(=NC=2C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C=CC=C1)F)F)C(C)C HYAIIJGDJZURIH-UHFFFAOYSA-N 0.000 claims description 3
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• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004438 haloalkoxy group Chemical group 0.000 claims 2
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• KQMUKMAFTCRLJF-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-cyanophenyl)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#N)C(C)C KQMUKMAFTCRLJF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• XEBHRARXJWILGQ-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-benzylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NCC1=CC=CC=C1)C(C)C XEBHRARXJWILGQ-UHFFFAOYSA-N 0.000 claims 1
• CDZSPVZPLANGDE-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-pyridin-2-ylurea Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(=O)NC1=NC=CC=C1)C(C)C CDZSPVZPLANGDE-UHFFFAOYSA-N 0.000 claims 1
• IWJPLCXKHVQRPM-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-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(C)C IWJPLCXKHVQRPM-UHFFFAOYSA-N 0.000 claims 1
• BHOJYKDKMYPGMD-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-pyridin-4-ylurea 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=NC=C1)C(C)C BHOJYKDKMYPGMD-UHFFFAOYSA-N 0.000 claims 1
• YYZLBFAXSXKRKQ-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-thiophen-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)NC1=CSC=C1)C(C)C YYZLBFAXSXKRKQ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• RLJDODLYJZYDIT-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-phenylurea 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(C)C RLJDODLYJZYDIT-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• HWNDVQSNELFXRT-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-phenylacetamide 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(C)C HWNDVQSNELFXRT-UHFFFAOYSA-N 0.000 claims 1
• BOHXLOGRAXUQQA-UHFFFAOYSA-N 2-[5-[8-amino-5-[4-(methylamino)cyclohexen-1-yl]-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]naphthalen-1-yl]-N-phenylacetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC)C(=NC=2C1=C2C=CC=C(C2=CC=C1)CC(=O)NC1=CC=CC=C1)C(C)C BOHXLOGRAXUQQA-UHFFFAOYSA-N 0.000 claims 1
• BHILGYPVRUUPNB-UHFFFAOYSA-N 5-[4-[2-fluoroethyl(methyl)amino]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 FCCN(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)C BHILGYPVRUUPNB-UHFFFAOYSA-N 0.000 claims 1
• BYVCCLUTTBHXNG-UHFFFAOYSA-N N-[4-[8-amino-3-methyl-1-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]naphthalen-1-yl]imidazo[1,5-a]pyrazin-5-yl]cyclohex-3-en-1-yl]acetamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)NC(C)=O)C(=NC=2C1=CC=C(C2=CC=CC=C12)NC(NC1=CC(=CC=C1)C(F)(F)F)=O)C BYVCCLUTTBHXNG-UHFFFAOYSA-N 0.000 claims 1
• QMWGADANCZDUJG-UHFFFAOYSA-N N-[4-[8-amino-5-(4-hydroxycyclohexen-1-yl)-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl]-2-fluorophenyl]-2-chlorobenzenesulfonamide Chemical compound NC=1C=2N(C(=CN=1)C1=CCC(CC1)O)C(=NC=2C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C=CC=C1)Cl)F)C(C)C QMWGADANCZDUJG-UHFFFAOYSA-N 0.000 claims 1
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