EA010727B1 - Аминогетероарильные соединения в качестве ингибиторов протеинкиназ - Google Patents

Info

Publication number

EA010727B1

EA010727B1 EA200501236A EA200501236A EA010727B1 EA 010727 B1 EA010727 B1 EA 010727B1 EA 200501236 A EA200501236 A EA 200501236A EA 200501236 A EA200501236 A EA 200501236A EA 010727 B1 EA010727 B1 EA 010727B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

pyridin

ethoxy

phenyl

chloro

Prior art date

2003-02-26

Links

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• Global Dossier
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• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract 2
• 239000003909 protein kinase inhibitor Substances 0.000 title abstract 2
• 125000005214 aminoheteroaryl group Chemical group 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 239
• XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical class NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims abstract description 8
• -1 2,6-dichloro-3 fluorophenyl Chemical group 0.000 claims description 802
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 362
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 290
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 249
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 236
• 125000001072 heteroaryl group Chemical group 0.000 claims description 180
• 125000003118 aryl group Chemical group 0.000 claims description 157
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 153
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 126
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 112
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 229910052736 halogen Inorganic materials 0.000 claims description 78
• 150000002367 halogens Chemical class 0.000 claims description 76
• 150000003839 salts Chemical class 0.000 claims description 64
• 125000003342 alkenyl group Chemical group 0.000 claims description 58
• 125000000304 alkynyl group Chemical group 0.000 claims description 58
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 56
• 239000002253 acid Substances 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 239000001257 hydrogen Substances 0.000 claims description 50
• 150000001408 amides Chemical class 0.000 claims description 44
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
• 239000012453 solvate Substances 0.000 claims description 30
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 23
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 20
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 239000010802 sludge Substances 0.000 claims description 18
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 150000004677 hydrates Chemical class 0.000 claims description 17
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 13
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 12
• 229910052700 potassium Inorganic materials 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 150000007513 acids Chemical class 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 8
• YUIOPHXTILULQC-UHFFFAOYSA-N 1,4-Dithiane-2,5-diol Chemical compound OC1CSC(O)CS1 YUIOPHXTILULQC-UHFFFAOYSA-N 0.000 claims description 8
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 8
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 8
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 8
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 8
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 8
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 8
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 8
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 8
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 8
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 8
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 8
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 8
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 8
• 229930192474 thiophene Natural products 0.000 claims description 8
• UFTHRGJTARTOQG-UHFFFAOYSA-N 5-(4-aminophenyl)-3-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-2-amine Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=C(N)C=C1 UFTHRGJTARTOQG-UHFFFAOYSA-N 0.000 claims description 7
• 239000005711 Benzoic acid Substances 0.000 claims description 7
• 235000010233 benzoic acid Nutrition 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• YSVRSETXLUMJPC-UHFFFAOYSA-N 5-(4-aminophenyl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=C(N)C=C1 YSVRSETXLUMJPC-UHFFFAOYSA-N 0.000 claims description 6
• YAAAHPOEWDXLHC-UHFFFAOYSA-N 5-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]-1h-indole-2-carboxylic acid Chemical compound NC1=NC=C(C=2C=C3C=C(NC3=CC=2)C(O)=O)C=C1OCC1=C(Cl)C=CC=C1Cl YAAAHPOEWDXLHC-UHFFFAOYSA-N 0.000 claims description 6
• HQYVQYLIERNMTM-UHFFFAOYSA-N ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(C#CC(C)(C)N)=CN=C1N Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(C#CC(C)(C)N)=CN=C1N HQYVQYLIERNMTM-UHFFFAOYSA-N 0.000 claims description 6
• 150000004885 piperazines Chemical class 0.000 claims description 6
• 150000003852 triazoles Chemical class 0.000 claims description 6
• SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 claims description 5
• MUMDVZVQLUFQIV-UHFFFAOYSA-N 5-(3-aminoprop-1-ynyl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(C#CCN)=CN=C1N MUMDVZVQLUFQIV-UHFFFAOYSA-N 0.000 claims description 5
• XQGNDISABQARPN-UHFFFAOYSA-N FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C1=CC=C(N)C=C1 Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C1=CC=C(N)C=C1 XQGNDISABQARPN-UHFFFAOYSA-N 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 5
• QLTUUGFFRPMGKH-UHFFFAOYSA-N 1-[4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C1=CC=C(NC(=O)NCCO)C=C1 QLTUUGFFRPMGKH-UHFFFAOYSA-N 0.000 claims description 4
• XZTBNGSZLDJNLI-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(3,4-dichlorophenyl)pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=C(Cl)C(Cl)=C1 XZTBNGSZLDJNLI-UHFFFAOYSA-N 0.000 claims description 4
• SDXGGNKSWPLCEN-UHFFFAOYSA-N 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-ethenylpyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(C=C)=CN=C1N SDXGGNKSWPLCEN-UHFFFAOYSA-N 0.000 claims description 4
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• MFDDBUXFUWDGAU-UHFFFAOYSA-N 5-(aminomethyl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-amine Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC1=CC(CN)=CN=C1N MFDDBUXFUWDGAU-UHFFFAOYSA-N 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• GDAWTQDKSMPLMQ-UHFFFAOYSA-N [4-[6-amino-5-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound C1C(C)NC(C)CN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)C=C1 GDAWTQDKSMPLMQ-UHFFFAOYSA-N 0.000 claims description 4
• FFUORYKWLCQODB-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCCN1CCOCC1 FFUORYKWLCQODB-UHFFFAOYSA-N 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• OIXSOQOJISAETD-UHFFFAOYSA-N 2-(diethylamino)ethanesulfonic acid Chemical compound CCN(CC)CCS(O)(=O)=O OIXSOQOJISAETD-UHFFFAOYSA-N 0.000 claims description 3
• QAQFKVYIYWEOIJ-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methoxy]-5-phenylpyridin-2-amine Chemical compound COC1=CC=CC(COC=2C(=NC=C(C=2)C=2C=CC=CC=2)N)=C1 QAQFKVYIYWEOIJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• GGBBFUHTLXMIEO-UHFFFAOYSA-N 5-[4-(2-morpholin-4-ylethoxy)phenyl]-3-[(3-nitrophenyl)methoxy]pyridin-2-amine Chemical compound NC1=NC=C(C=2C=CC(OCCN3CCOCC3)=CC=2)C=C1OCC1=CC=CC([N+]([O-])=O)=C1 GGBBFUHTLXMIEO-UHFFFAOYSA-N 0.000 claims description 3
• XFXKQRFLZQWZIL-UHFFFAOYSA-N 5-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]thiophene-2-carboxylic acid Chemical compound NC1=NC=C(C=2SC(=CC=2)C(O)=O)C=C1OCC1=C(F)C=CC(F)=C1Cl XFXKQRFLZQWZIL-UHFFFAOYSA-N 0.000 claims description 3
• WSMASMMUYIRFBS-UHFFFAOYSA-N 5-phenyl-3-phenylmethoxypyridin-2-amine Chemical compound NC1=NC=C(C=2C=CC=CC=2)C=C1OCC1=CC=CC=C1 WSMASMMUYIRFBS-UHFFFAOYSA-N 0.000 claims description 3
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
• ODYVNXUCWDIVSA-UHFFFAOYSA-N N-[4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]ethanesulfonamide Chemical compound NC=1N=CC(=NC=1OC(C)C1=C(C(=CC=C1F)F)Cl)C1=CC=C(C=C1)NS(=O)(=O)CC ODYVNXUCWDIVSA-UHFFFAOYSA-N 0.000 claims description 3
• YSDLHTWNCGDLGW-UHFFFAOYSA-N [3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)N(CC1)CCC1N1CCCC1 YSDLHTWNCGDLGW-UHFFFAOYSA-N 0.000 claims description 3
• GCHURKJETQITJF-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 GCHURKJETQITJF-UHFFFAOYSA-N 0.000 claims description 3
• 239000004202 carbamide Substances 0.000 claims description 3
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
• WTDFFADXONGQOM-UHFFFAOYSA-N formaldehyde;hydrochloride Chemical compound Cl.O=C WTDFFADXONGQOM-UHFFFAOYSA-N 0.000 claims description 3
• VFQYQYRTIQWWPE-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCN1CCOCC1 VFQYQYRTIQWWPE-UHFFFAOYSA-N 0.000 claims description 3
• AOQMMUWCTVLKPT-UHFFFAOYSA-N n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCCN1CCCC1 AOQMMUWCTVLKPT-UHFFFAOYSA-N 0.000 claims description 3
• GBALKEWUZFZVFX-UHFFFAOYSA-N n-[4-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-2-(dimethylamino)ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CCN(C)C)=CC=C1C1=CN=C(N)C(OCC=2C(=C(F)C=CC=2F)Cl)=N1 GBALKEWUZFZVFX-UHFFFAOYSA-N 0.000 claims description 3
• USXYBTKLOOTSLM-UHFFFAOYSA-N 1,5-dimethylcyclohexa-2,4-diene-1-sulfonamide Chemical compound C1(CC(=CC=C1)C)(C)S(=O)(=O)N USXYBTKLOOTSLM-UHFFFAOYSA-N 0.000 claims description 2
• UNVPBZBLHBHHOY-UHFFFAOYSA-N 1-[2-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]ethanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=CC=C1C(C)=O UNVPBZBLHBHHOY-UHFFFAOYSA-N 0.000 claims description 2
• GVNORZZHNRNGDW-UHFFFAOYSA-N 1-[3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]ethanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=CC(C(C)=O)=C1 GVNORZZHNRNGDW-UHFFFAOYSA-N 0.000 claims description 2
• FAVGJHQJXTYWOL-UHFFFAOYSA-N 1-[3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]prop-2-ynyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C#CCNC(=O)NCCN1CCOCC1 FAVGJHQJXTYWOL-UHFFFAOYSA-N 0.000 claims description 2
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• QXRWYXPNIHEXBE-UHFFFAOYSA-N 1-[3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]prop-2-ynyl]-3-(3-morpholin-4-ylpropyl)urea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C#CCNC(=O)NCCCN1CCOCC1 QXRWYXPNIHEXBE-UHFFFAOYSA-N 0.000 claims description 2
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• YEJNKQPKGUJMMK-UHFFFAOYSA-N 1-[4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1NC(=O)NCCN1CCOCC1 YEJNKQPKGUJMMK-UHFFFAOYSA-N 0.000 claims description 2
• ZEXMMVGQCVSRRC-UHFFFAOYSA-N 1-[4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1NC(=O)NCCN1CCCC1 ZEXMMVGQCVSRRC-UHFFFAOYSA-N 0.000 claims description 2
• XWFPBJZMVURHRN-UHFFFAOYSA-N 1-[4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-3-(1-methylpiperidin-4-yl)urea Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1NC(=O)NC1CCN(C)CC1 XWFPBJZMVURHRN-UHFFFAOYSA-N 0.000 claims description 2
• DWPMATUCAYMTAB-UHFFFAOYSA-N 1-[4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=C(NC(=O)NCCO)C=C1 DWPMATUCAYMTAB-UHFFFAOYSA-N 0.000 claims description 2
• XRWLWJIPXPLPMD-UHFFFAOYSA-N 1-[4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1NC(=O)NCCN1CCOCC1 XRWLWJIPXPLPMD-UHFFFAOYSA-N 0.000 claims description 2
• AYEAIVKAJGVMMD-UHFFFAOYSA-N 1-[4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1NC(=O)NCCN1CCCC1 AYEAIVKAJGVMMD-UHFFFAOYSA-N 0.000 claims description 2
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• NZJFYKXRMJBRCA-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methoxy]-5-[2-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound NC1=NC=C(C=2C(=CC=CC=2)C(F)(F)F)C=C1OCC1=C(Cl)C=CC=C1Cl NZJFYKXRMJBRCA-UHFFFAOYSA-N 0.000 claims description 2
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• UKXPTPMOZOVUOL-UHFFFAOYSA-N [2-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]methanol Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=CC=C1CO UKXPTPMOZOVUOL-UHFFFAOYSA-N 0.000 claims description 2
• WMSLBRSXPGYZKZ-UHFFFAOYSA-N [3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2N=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 WMSLBRSXPGYZKZ-UHFFFAOYSA-N 0.000 claims description 2
• QUDKNHMGJFQVBG-UHFFFAOYSA-N [3-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)N(CC1)CCC1N1CCCC1 QUDKNHMGJFQVBG-UHFFFAOYSA-N 0.000 claims description 2
• DHQCDCMHAYULMK-UHFFFAOYSA-N [3-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[4-(cyclopropylamino)piperidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)N(CC1)CCC1NC1CC1 DHQCDCMHAYULMK-UHFFFAOYSA-N 0.000 claims description 2
• LSQMGGSDIJYTIZ-UHFFFAOYSA-N [3-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)N1CCN(C)CC1 LSQMGGSDIJYTIZ-UHFFFAOYSA-N 0.000 claims description 2
• SNZVYQKLPGTZLQ-UHFFFAOYSA-N [3-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)N(CC1)CCC1N1CCCC1 SNZVYQKLPGTZLQ-UHFFFAOYSA-N 0.000 claims description 2
• LXZLKOHQORCVBG-UHFFFAOYSA-N [3-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)N1CCN(C)CC1 LXZLKOHQORCVBG-UHFFFAOYSA-N 0.000 claims description 2
• RCTKNLJLGCDXFZ-UHFFFAOYSA-N [3-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=CC=1C(=O)N(CC1)CCC1N1CCCC1 RCTKNLJLGCDXFZ-UHFFFAOYSA-N 0.000 claims description 2
• CXOARPAHZCTFHX-UHFFFAOYSA-N [3-[5-amino-6-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2N=C(OCC=3C(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)=C1 CXOARPAHZCTFHX-UHFFFAOYSA-N 0.000 claims description 2
• FBSWXLMJSBVRQH-UHFFFAOYSA-N [3-[5-amino-6-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2C=C(C=CC=2)C(=O)N2CCC(CC2)N2CCCC2)N=C1OCC1=CC=CC(F)=C1C(F)(F)F FBSWXLMJSBVRQH-UHFFFAOYSA-N 0.000 claims description 2
• CQWJGEXEULXQQB-UHFFFAOYSA-N [3-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound C1C(C)NC(C)CN1C(=O)C1=CC=CC(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 CQWJGEXEULXQQB-UHFFFAOYSA-N 0.000 claims description 2
• FBLIJTZELJTOSH-UHFFFAOYSA-N [3-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-(4-aminopiperidin-1-yl)methanone Chemical compound C1CC(N)CCN1C(=O)C1=CC=CC(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 FBLIJTZELJTOSH-UHFFFAOYSA-N 0.000 claims description 2
• CAEYRQHXINZGJK-UHFFFAOYSA-N [3-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 CAEYRQHXINZGJK-UHFFFAOYSA-N 0.000 claims description 2
• FQNFURORIUWZRG-UHFFFAOYSA-N [3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]methanol Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=CC(CO)=C1 FQNFURORIUWZRG-UHFFFAOYSA-N 0.000 claims description 2
• WDHNKXHMNWAHSR-UHFFFAOYSA-N [3-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)N1CCN(C)CC1 WDHNKXHMNWAHSR-UHFFFAOYSA-N 0.000 claims description 2
• QJQSIADNHSMFPN-UHFFFAOYSA-N [3-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=CC=1C(=O)N1CCN(C)CC1 QJQSIADNHSMFPN-UHFFFAOYSA-N 0.000 claims description 2
• UVBCTMGXAWIUCG-UHFFFAOYSA-N [4-(6-amino-5-phenylmethoxypyridin-3-yl)phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound C1C(C)NC(C)CN1C(=O)C1=CC=C(C=2C=C(OCC=3C=CC=CC=3)C(N)=NC=2)C=C1 UVBCTMGXAWIUCG-UHFFFAOYSA-N 0.000 claims description 2
• XQMMXRNZDXAVRE-UHFFFAOYSA-N [4-(6-amino-5-phenylmethoxypyridin-3-yl)phenyl]-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C=CC=CC=3)C(N)=NC=2)C=C1 XQMMXRNZDXAVRE-UHFFFAOYSA-N 0.000 claims description 2
• JRCILYMTZPSJQS-UHFFFAOYSA-N [4-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2N=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)C=C1 JRCILYMTZPSJQS-UHFFFAOYSA-N 0.000 claims description 2
• WASOVOHUGKCSCW-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 WASOVOHUGKCSCW-UHFFFAOYSA-N 0.000 claims description 2
• KORDDKAJGCSZEW-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 KORDDKAJGCSZEW-UHFFFAOYSA-N 0.000 claims description 2
• BQKSTOOQRYVIRH-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-[4-(cyclopropylamino)piperidin-1-yl]methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1NC1CC1 BQKSTOOQRYVIRH-UHFFFAOYSA-N 0.000 claims description 2
• VYUSJOHXURFLCW-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CC=NC=1C(=O)N1CCN(C)CC1 VYUSJOHXURFLCW-UHFFFAOYSA-N 0.000 claims description 2
• PSYYECZBGYXYGV-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 PSYYECZBGYXYGV-UHFFFAOYSA-N 0.000 claims description 2
• UIUDVWLKLLITRL-UHFFFAOYSA-N [4-[5-amino-6-[1-(2,6-dichlorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 UIUDVWLKLLITRL-UHFFFAOYSA-N 0.000 claims description 2
• DUVZYOINSBFADI-UHFFFAOYSA-N [4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 DUVZYOINSBFADI-UHFFFAOYSA-N 0.000 claims description 2
• ZGMVUAVFZJKNEW-UHFFFAOYSA-N [4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 ZGMVUAVFZJKNEW-UHFFFAOYSA-N 0.000 claims description 2
• QHYJSQQUMNBASW-UHFFFAOYSA-N [4-[5-amino-6-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyrazin-2-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)N=C1OCC1=CC=CC(F)=C1C(F)(F)F QHYJSQQUMNBASW-UHFFFAOYSA-N 0.000 claims description 2
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• KYWAICZFDNAJLJ-UHFFFAOYSA-N [4-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]phenyl]methanol Chemical compound NC1=NC=C(C=2C=CC(CO)=CC=2)C=C1OCC1=C(Cl)C=CC=C1Cl KYWAICZFDNAJLJ-UHFFFAOYSA-N 0.000 claims description 2
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• CIRAQVLTXSCTHW-UHFFFAOYSA-N [4-[6-amino-5-[(4-tert-butylphenyl)methoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C=CC(=CC=3)C(C)(C)C)C(N)=NC=2)C=C1 CIRAQVLTXSCTHW-UHFFFAOYSA-N 0.000 claims description 2
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• XVBOYOUFSVIWSH-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-3-methylphenyl]-(2,2-dimethylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C(=C1)C)=CC=C1C(=O)N1CCNCC1(C)C XVBOYOUFSVIWSH-UHFFFAOYSA-N 0.000 claims description 2
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• OWJYVAGQUFLWBE-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 OWJYVAGQUFLWBE-UHFFFAOYSA-N 0.000 claims description 2
• CDAABCUOKXSPJC-UHFFFAOYSA-N [4-[6-amino-5-[1-(2,6-dichlorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 CDAABCUOKXSPJC-UHFFFAOYSA-N 0.000 claims description 2
• GDNMBLFQCIKWSG-UHFFFAOYSA-N [4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(C=2C=C(OC(C)C=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)C=C1 GDNMBLFQCIKWSG-UHFFFAOYSA-N 0.000 claims description 2
• ZQAQQCXBCQPQOX-UHFFFAOYSA-N [4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 ZQAQQCXBCQPQOX-UHFFFAOYSA-N 0.000 claims description 2
• HGTBKRYDMKQWBN-UHFFFAOYSA-N [4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 HGTBKRYDMKQWBN-UHFFFAOYSA-N 0.000 claims description 2
• QTKJXYDBTIWDAC-UHFFFAOYSA-N [4-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CC=NC=1C(=O)N1CCN(C)CC1 QTKJXYDBTIWDAC-UHFFFAOYSA-N 0.000 claims description 2
• NLSGGEDXODSKPV-UHFFFAOYSA-N [4-[6-amino-5-[1-[2-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC(C)NC(C)C1 NLSGGEDXODSKPV-UHFFFAOYSA-N 0.000 claims description 2
• WLBBAKVPDWTROC-UHFFFAOYSA-N [4-[6-amino-5-[1-[3-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-(3,5-dimethylpiperazin-1-yl)methanone Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N1CC(C)NC(C)C1 WLBBAKVPDWTROC-UHFFFAOYSA-N 0.000 claims description 2
• GSTGRNHIGZKLTR-UHFFFAOYSA-N [4-[6-amino-5-[1-[3-fluoro-2-(trifluoromethyl)phenyl]ethoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound C=1C=CC(F)=C(C(F)(F)F)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 GSTGRNHIGZKLTR-UHFFFAOYSA-N 0.000 claims description 2
• GMQINZXTXZUSGP-UHFFFAOYSA-N [4-[6-amino-5-[[2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=CC=CC=3)C(F)(F)F)C(N)=NC=2)C=C1 GMQINZXTXZUSGP-UHFFFAOYSA-N 0.000 claims description 2
• HHLJBWJBMWNGOP-UHFFFAOYSA-N [4-[6-amino-5-[[2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)C=C1OCC1=CC=CC=C1C(F)(F)F HHLJBWJBMWNGOP-UHFFFAOYSA-N 0.000 claims description 2
• JMFREZMQIYMKAO-UHFFFAOYSA-N [4-[6-amino-5-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)C=C1 JMFREZMQIYMKAO-UHFFFAOYSA-N 0.000 claims description 2
• QKNTVQVVZBGJGN-UHFFFAOYSA-N [4-[6-amino-5-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]phenyl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)C=C1OCC1=CC=CC(F)=C1C(F)(F)F QKNTVQVVZBGJGN-UHFFFAOYSA-N 0.000 claims description 2
• GFOGAKOOQFXPTC-UHFFFAOYSA-N [4-[6-amino-5-[[3-fluoro-2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]phenyl]-[3-(dimethylamino)pyrrolidin-1-yl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=C(F)C=CC=3)C(F)(F)F)C(N)=NC=2)C=C1 GFOGAKOOQFXPTC-UHFFFAOYSA-N 0.000 claims description 2
• FINPBYRDTVSMRZ-UHFFFAOYSA-N [5-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]thiophen-2-yl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2SC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)N=C1OCC1=C(F)C=CC(F)=C1Cl FINPBYRDTVSMRZ-UHFFFAOYSA-N 0.000 claims description 2
• LGGUYGOKKTVPCH-UHFFFAOYSA-N [5-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=1)=CN=CC=1C(=O)N1CCN(C)CC1 LGGUYGOKKTVPCH-UHFFFAOYSA-N 0.000 claims description 2
• ZURQXWIYRKRKHN-UHFFFAOYSA-N [5-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]thiophen-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)S1 ZURQXWIYRKRKHN-UHFFFAOYSA-N 0.000 claims description 2
• FQXVPKZLKKFLLQ-UHFFFAOYSA-N [5-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]thiophen-2-yl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound NC1=NC=C(C=2SC(=CC=2)C(=O)N2CCC(CC2)N2CCCC2)C=C1OCC1=C(F)C=CC(F)=C1Cl FQXVPKZLKKFLLQ-UHFFFAOYSA-N 0.000 claims description 2
• KYBBGWCVQUTRDW-UHFFFAOYSA-N [5-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=1)=CN=CC=1C(=O)N1CCN(C)CC1 KYBBGWCVQUTRDW-UHFFFAOYSA-N 0.000 claims description 2
• MOFORHKMXAUGMV-UHFFFAOYSA-N [5-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=N1)=CC=C1C(=O)N1CCN(C)CC1 MOFORHKMXAUGMV-UHFFFAOYSA-N 0.000 claims description 2
• PZJSFGFQDYOEDD-UHFFFAOYSA-N [6-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(N=1)=CC=CC=1C(=O)N1CCN(C)CC1 PZJSFGFQDYOEDD-UHFFFAOYSA-N 0.000 claims description 2
• DXJDJFDHQSGWOY-UHFFFAOYSA-N [6-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(N=C1)=CC=C1C(=O)N1CCN(C)CC1 DXJDJFDHQSGWOY-UHFFFAOYSA-N 0.000 claims description 2
• UIVFGHYSQQNWFN-UHFFFAOYSA-N [6-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(N=C1)=CC=C1C(=O)N1CCN(C)CC1 UIVFGHYSQQNWFN-UHFFFAOYSA-N 0.000 claims description 2
• SKLSFPPQMIPPEZ-UHFFFAOYSA-N [6-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]pyridin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=C(C=2N=C(OC(C)C=3C(=C(F)C=CC=3Cl)Cl)C(N)=NC=2)N=C1 SKLSFPPQMIPPEZ-UHFFFAOYSA-N 0.000 claims description 2
• UGCAPERLWHYSIC-UHFFFAOYSA-N [6-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(N=1)=CC=CC=1C(=O)N1CCN(C)CC1 UGCAPERLWHYSIC-UHFFFAOYSA-N 0.000 claims description 2
• JJGANHPZLZTDGT-UHFFFAOYSA-N [6-[6-amino-5-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyridin-3-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(N=C1)=CC=C1C(=O)N1CCN(C)CC1 JJGANHPZLZTDGT-UHFFFAOYSA-N 0.000 claims description 2
• 125000002723 alicyclic group Chemical group 0.000 claims description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 2
• FCOFUDRGQXLVKL-UHFFFAOYSA-N ethyl 2-[4-[6-amino-5-[(2,6-difluorophenyl)methoxy]pyridin-3-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1C1=CN=C(N)C(OCC=2C(=CC=CC=2F)F)=C1 FCOFUDRGQXLVKL-UHFFFAOYSA-N 0.000 claims description 2
• CBLZKOARTGRECJ-UHFFFAOYSA-N ethyl 5-[6-amino-5-[(2,6-dichlorophenyl)methoxy]pyridin-3-yl]-1h-indole-2-carboxylate Chemical compound C=1C=C2NC(C(=O)OCC)=CC2=CC=1C(C=1)=CN=C(N)C=1OCC1=C(Cl)C=CC=C1Cl CBLZKOARTGRECJ-UHFFFAOYSA-N 0.000 claims description 2
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
• ICDGQBSINVDDNH-UHFFFAOYSA-N methyl 2-[4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C1=CN=C(N)C(OC(C)C=2C(=C(F)C=CC=2Cl)Cl)=C1 ICDGQBSINVDDNH-UHFFFAOYSA-N 0.000 claims description 2
• UEGIWWILYKXDGR-UHFFFAOYSA-N methyl 3-[[2-amino-5-[4-(3,5-dimethylpiperazine-1-carbonyl)phenyl]pyridin-3-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C(=NC=C(C=2)C=2C=CC(=CC=2)C(=O)N2CC(C)NC(C)C2)N)=C1 UEGIWWILYKXDGR-UHFFFAOYSA-N 0.000 claims description 2
• ARGHYNJBPLSKRW-UHFFFAOYSA-N methyl 4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C1=CN=C(N)C(OC(C)C=2C(=C(F)C=CC=2Cl)Cl)=C1 ARGHYNJBPLSKRW-UHFFFAOYSA-N 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• IAMPDRRVWOQHHR-UHFFFAOYSA-N n-[3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-2-(cyclopropylamino)ethanesulfonamide Chemical compound NC1=NC=C(C=2C=C(NS(=O)(=O)CCNC3CC3)C=CC=2)N=C1OCC1=C(F)C=CC(F)=C1Cl IAMPDRRVWOQHHR-UHFFFAOYSA-N 0.000 claims description 2
• CJHGLAARFIMKNY-UHFFFAOYSA-N n-[3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-2-(cyclopropylmethylamino)ethanesulfonamide Chemical compound NC1=NC=C(C=2C=C(NS(=O)(=O)CCNCC3CC3)C=CC=2)N=C1OCC1=C(F)C=CC(F)=C1Cl CJHGLAARFIMKNY-UHFFFAOYSA-N 0.000 claims description 2
• FRJNLEFOROHHPZ-UHFFFAOYSA-N n-[3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-2-(diethylamino)ethanesulfonamide Chemical compound CCN(CC)CCS(=O)(=O)NC1=CC=CC(C=2N=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 FRJNLEFOROHHPZ-UHFFFAOYSA-N 0.000 claims description 2
• WLKCNQKSMUQWMY-UHFFFAOYSA-N n-[3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-2-(dimethylamino)ethanesulfonamide Chemical compound CN(C)CCS(=O)(=O)NC1=CC=CC(C=2N=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 WLKCNQKSMUQWMY-UHFFFAOYSA-N 0.000 claims description 2
• IWHAZWQZFQZWPD-UHFFFAOYSA-N n-[3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-2-[4-(2-hydroxyacetyl)piperazin-1-yl]ethanesulfonamide Chemical compound NC1=NC=C(C=2C=C(NS(=O)(=O)CCN3CCN(CC3)C(=O)CO)C=CC=2)N=C1OCC1=C(F)C=CC(F)=C1Cl IWHAZWQZFQZWPD-UHFFFAOYSA-N 0.000 claims description 2
• CNGUDOJBIWSGSB-UHFFFAOYSA-N n-[3-[5-amino-6-[(2-chloro-3,6-difluorophenyl)methoxy]pyrazin-2-yl]phenyl]-2-pyrrolidin-1-ylethanesulfonamide Chemical compound NC1=NC=C(C=2C=C(NS(=O)(=O)CCN3CCCC3)C=CC=2)N=C1OCC1=C(F)C=CC(F)=C1Cl CNGUDOJBIWSGSB-UHFFFAOYSA-N 0.000 claims description 2
• RZVTYDFOUPUICN-UHFFFAOYSA-N n-[3-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-2-(diethylamino)ethanesulfonamide Chemical compound CCN(CC)CCS(=O)(=O)NC1=CC=CC(C=2C=C(OCC=3C(=C(F)C=CC=3F)Cl)C(N)=NC=2)=C1 RZVTYDFOUPUICN-UHFFFAOYSA-N 0.000 claims description 2
• ZCBIWSPFLPWAQV-UHFFFAOYSA-N n-[3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]prop-2-ynyl]-4-methylpiperazine-1-carboxamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C#CCNC(=O)N1CCN(C)CC1 ZCBIWSPFLPWAQV-UHFFFAOYSA-N 0.000 claims description 2
• PKSBAWQOPGQPLS-UHFFFAOYSA-N n-[3-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]prop-2-ynyl]-4-pyrrolidin-1-ylpiperidine-1-carboxamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C#CCNC(=O)N(CC1)CCC1N1CCCC1 PKSBAWQOPGQPLS-UHFFFAOYSA-N 0.000 claims description 2
• SFJRXAIQIZRNJC-UHFFFAOYSA-N n-[4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-2-(4-hydroxypiperidin-1-yl)ethanesulfonamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1NS(=O)(=O)CCN1CCC(O)CC1 SFJRXAIQIZRNJC-UHFFFAOYSA-N 0.000 claims description 2
• XYTQSLMCOXKNSC-UHFFFAOYSA-N n-[4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-2-(diethylamino)ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CCN(CC)CC)=CC=C1C1=CN=C(N)C(OC(C)C=2C(=C(F)C=CC=2Cl)Cl)=N1 XYTQSLMCOXKNSC-UHFFFAOYSA-N 0.000 claims description 2
• IHGRHDPOLIBBDA-UHFFFAOYSA-N n-[4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-2-(dimethylamino)ethanesulfonamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C1=CC=C(NS(=O)(=O)CCN(C)C)C=C1 IHGRHDPOLIBBDA-UHFFFAOYSA-N 0.000 claims description 2
• PKXYROSEXPOAIM-UHFFFAOYSA-N n-[4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-2-pyrrolidin-1-ylethanesulfonamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1NS(=O)(=O)CCN1CCCC1 PKXYROSEXPOAIM-UHFFFAOYSA-N 0.000 claims description 2
• YYNPDXVSPZDOMQ-UHFFFAOYSA-N n-[4-[5-amino-6-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-4-methylpiperazine-1-carboxamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1NC(=O)N1CCN(C)CC1 YYNPDXVSPZDOMQ-UHFFFAOYSA-N 0.000 claims description 2
• SQUICNYYYZBLJC-UHFFFAOYSA-N n-[4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-2-[4-(2-hydroxyacetyl)piperazin-1-yl]ethanesulfonamide Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1NS(=O)(=O)CCN1CCN(C(=O)CO)CC1 SQUICNYYYZBLJC-UHFFFAOYSA-N 0.000 claims description 2
• BDRVEAGDBLTXCK-UHFFFAOYSA-N n-[4-[5-amino-6-[1-(2-chloro-3,6-difluorophenyl)ethoxy]pyrazin-2-yl]phenyl]-4-methylpiperazine-1-carboxamide Chemical compound FC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=NC=1C(C=C1)=CC=C1NC(=O)N1CCN(C)CC1 BDRVEAGDBLTXCK-UHFFFAOYSA-N 0.000 claims description 2
• VQTOUEXUOHWPAX-UHFFFAOYSA-N n-[4-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-2-(diethylamino)ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CCN(CC)CC)=CC=C1C1=CN=C(N)C(OCC=2C(=C(F)C=CC=2F)Cl)=C1 VQTOUEXUOHWPAX-UHFFFAOYSA-N 0.000 claims description 2
• SWGQPFCOSUGUSZ-UHFFFAOYSA-N n-[4-[6-amino-5-[(2-chloro-3,6-difluorophenyl)methoxy]pyridin-3-yl]phenyl]-2-(dimethylamino)ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CCN(C)C)=CC=C1C1=CN=C(N)C(OCC=2C(=C(F)C=CC=2F)Cl)=C1 SWGQPFCOSUGUSZ-UHFFFAOYSA-N 0.000 claims description 2
• HJLYJIKFIXFFNO-UHFFFAOYSA-N n-[4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-2-(cyclopropylamino)ethanesulfonamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C(C=C1)=CC=C1NS(=O)(=O)CCNC1CC1 HJLYJIKFIXFFNO-UHFFFAOYSA-N 0.000 claims description 2
• AJPNUMSKDNRFPP-UHFFFAOYSA-N n-[4-[6-amino-5-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-3-yl]phenyl]-2-(dimethylamino)ethanesulfonamide Chemical compound ClC=1C=CC(F)=C(Cl)C=1C(C)OC(C(=NC=1)N)=CC=1C1=CC=C(NS(=O)(=O)CCN(C)C)C=C1 AJPNUMSKDNRFPP-UHFFFAOYSA-N 0.000 claims description 2
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