JP2011511034A5

JP2011511034A5 -

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Publication number: JP2011511034A5
Authority: JP; Japan
Prior art keywords: phenyl; pyrrolo; pyrimidin; ylmethyl; morpholin
Prior art date: 2009-02-04
Legal status : Granted

Application number

JP2010545458A

Other languages

English (en)

Japanese (ja)

Other versions

JP5323095B2 (ja

JP2011511034A (ja

Filing date

2009-02-04

Publication date

2012-06-07

2009-02-04 Application filed filed Critical

2009-02-04 Priority claimed from PCT/EP2009/051281 external-priority patent/WO2009098236A1/en

2011-04-07 Publication of JP2011511034A publication Critical patent/JP2011511034A/ja

2012-06-07 Publication of JP2011511034A5 publication Critical patent/JP2011511034A5/ja

2013-10-23 Application granted granted Critical

2013-10-23 Publication of JP5323095B2 publication Critical patent/JP5323095B2/ja

Status Expired - Fee Related legal-status Critical Current

2029-02-04 Anticipated expiration legal-status Critical

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RXIWRPMVWOVCKL-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(5-methyl-6-piperazin-1-ylpyridin-3-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C=1N=C(N2CCNCC2)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 RXIWRPMVWOVCKL-UHFFFAOYSA-N 0.000 claims description 3
-1 C 1 -C 7 - alkoxy Chemical group 0.000 claims 72
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 41
229910052739 hydrogen Inorganic materials 0.000 claims 32
239000001257 hydrogen Substances 0.000 claims 31
150000002431 hydrogen Chemical class 0.000 claims 24
150000001875 compounds Chemical class 0.000 claims 19
125000001153 fluoro group Chemical group F* 0.000 claims 15
150000003839 salts Chemical class 0.000 claims 15
125000001424 substituent group Chemical group 0.000 claims 15
125000000623 heterocyclic group Chemical group 0.000 claims 14
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 12
125000001309 chloro group Chemical group Cl* 0.000 claims 11
229910052757 nitrogen Inorganic materials 0.000 claims 11
201000010099 disease Diseases 0.000 claims 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
125000000000 cycloalkoxy group Chemical group 0.000 claims 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
125000000753 cycloalkyl group Chemical group 0.000 claims 8
229910052736 halogen Inorganic materials 0.000 claims 8
150000002367 halogens Chemical class 0.000 claims 8
230000001404 mediated effect Effects 0.000 claims 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
125000000217 alkyl group Chemical group 0.000 claims 7
125000005347 halocycloalkyl group Chemical group 0.000 claims 7
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 7
101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 6
102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 6
229910052799 carbon Inorganic materials 0.000 claims 6
125000001188 haloalkyl group Chemical group 0.000 claims 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
UUKNHVGOEZQOQE-UHFFFAOYSA-N [2,6-difluoro-4-[2-(4-fluoro-3-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(F)C(C)=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 UUKNHVGOEZQOQE-UHFFFAOYSA-N 0.000 claims 5
125000003545 alkoxy group Chemical group 0.000 claims 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
125000003118 aryl group Chemical group 0.000 claims 4
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 4
125000005843 halogen group Chemical group 0.000 claims 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
239000008194 pharmaceutical composition Substances 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
229910052717 sulfur Inorganic materials 0.000 claims 4
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
125000006413 ring segment Chemical group 0.000 claims 3
WICZMCGIKOFUPP-UHFFFAOYSA-N 1-[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-3,3-dimethylpiperazin-2-one Chemical compound O=C1C(C)(C)NCCN1C1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 WICZMCGIKOFUPP-UHFFFAOYSA-N 0.000 claims 2
ONEAOUHSDGYSHL-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-methyl-3-(piperazin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CCNCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 ONEAOUHSDGYSHL-UHFFFAOYSA-N 0.000 claims 2
GODKPWYLLOOFQL-KDURUIRLSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 GODKPWYLLOOFQL-KDURUIRLSA-N 0.000 claims 2
208000032027 Essential Thrombocythemia Diseases 0.000 claims 2
206010028980 Neoplasm Diseases 0.000 claims 2
108091000080 Phosphotransferase Proteins 0.000 claims 2
QSWUWVCHHYZJCJ-UHFFFAOYSA-N [2-fluoro-4-[2-(4-fluoro-3-methoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(F)C(OC)=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=C1 QSWUWVCHHYZJCJ-UHFFFAOYSA-N 0.000 claims 2
208000017733 acquired polycythemia vera Diseases 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
239000003085 diluting agent Substances 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
125000001072 heteroaryl group Chemical group 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
208000032839 leukemia Diseases 0.000 claims 2
125000002757 morpholinyl group Chemical group 0.000 claims 2
102000020233 phosphotransferase Human genes 0.000 claims 2
125000004193 piperazinyl group Chemical group 0.000 claims 2
208000037244 polycythemia vera Diseases 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
208000003476 primary myelofibrosis Diseases 0.000 claims 2
230000002062 proliferating effect Effects 0.000 claims 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
229920006395 saturated elastomer Polymers 0.000 claims 2
125000000547 substituted alkyl group Chemical group 0.000 claims 2
125000003107 substituted aryl group Chemical group 0.000 claims 2
IFNWESYYDINUHV-OLQVQODUSA-N (2s,6r)-2,6-dimethylpiperazine Chemical compound C[C@H]1CNC[C@@H](C)N1 IFNWESYYDINUHV-OLQVQODUSA-N 0.000 claims 1
UCFQTVKHBADDQH-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methanone Chemical compound FC1=CC(N2C3=NC(NC=4C=C(C=CC=4)C(=O)N4CCN(CC4)C4CC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 UCFQTVKHBADDQH-UHFFFAOYSA-N 0.000 claims 1
MRZSXOCJELDDDW-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[3-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 MRZSXOCJELDDDW-UHFFFAOYSA-N 0.000 claims 1
QQZZYLMMAXTHGM-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 QQZZYLMMAXTHGM-UHFFFAOYSA-N 0.000 claims 1
VDPNMAOGBHADDP-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-2-[3-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 VDPNMAOGBHADDP-UHFFFAOYSA-N 0.000 claims 1
APPOWPZWICPKLL-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-2-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCN(C)CC4)=CC=3)C2=N1 APPOWPZWICPKLL-UHFFFAOYSA-N 0.000 claims 1
DSDQOHOVFSCAFU-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-2-[4-[2-[4-(trifluoromethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=C(N2C3=NC(NC=4C=CC(=CC=4)C(F)(F)F)=NC=C3C=C2)C=C1 DSDQOHOVFSCAFU-UHFFFAOYSA-N 0.000 claims 1
PVODAPXRCSUPHL-UHFFFAOYSA-N 1-[4-[2-(4-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C2=NC(NC=3C=CC(F)=CC=3)=NC=C2C=C1 PVODAPXRCSUPHL-UHFFFAOYSA-N 0.000 claims 1
CYALKYABLDDHKR-UHFFFAOYSA-N 1-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanol Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(C)O)C2=N1 CYALKYABLDDHKR-UHFFFAOYSA-N 0.000 claims 1
GDKOPUXCQQQONP-UHFFFAOYSA-N 1-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(C)=O)C2=N1 GDKOPUXCQQQONP-UHFFFAOYSA-N 0.000 claims 1
GZSAGVZAELWUKO-UHFFFAOYSA-N 1-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]piperazin-2-one Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)N3C(CNCC3)=O)C2=N1 GZSAGVZAELWUKO-UHFFFAOYSA-N 0.000 claims 1
MBFAYKIJUBBRPK-UHFFFAOYSA-N 1-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]pyrrolidin-2-one Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)N3C(CCC3)=O)C2=N1 MBFAYKIJUBBRPK-UHFFFAOYSA-N 0.000 claims 1
HSJMSPWPKWGWFR-UHFFFAOYSA-N 1-[4-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1N1C2=NC(NC=3C=NC(=CC=3)N3CCN(C)CC3)=NC=C2C=C1 HSJMSPWPKWGWFR-UHFFFAOYSA-N 0.000 claims 1
YPVXCUFNOYDSTQ-UHFFFAOYSA-N 1-[4-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)N3C(CCC3)=O)C2=N1 YPVXCUFNOYDSTQ-UHFFFAOYSA-N 0.000 claims 1
UVMSJUCTHMXAIV-UHFFFAOYSA-N 1-[4-[[2,6-difluoro-4-[2-(4-fluoro-3-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=C(F)C=C(N2C3=NC(NC=4C=C(C)C(F)=CC=4)=NC=C3C=C2)C=C1F UVMSJUCTHMXAIV-UHFFFAOYSA-N 0.000 claims 1
LQWPKHNSNJLUBE-UHFFFAOYSA-N 1-[4-[[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 LQWPKHNSNJLUBE-UHFFFAOYSA-N 0.000 claims 1
STGUNWIJJJZJJB-UHFFFAOYSA-N 1-[4-[[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 STGUNWIJJJZJJB-UHFFFAOYSA-N 0.000 claims 1
PRUSKKQVEDWRET-UHFFFAOYSA-N 1-[4-[[4-[[7-[3,5-difluoro-4-(morpholine-4-carbonyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 PRUSKKQVEDWRET-UHFFFAOYSA-N 0.000 claims 1
YAXAUMXYZWVOAJ-UHFFFAOYSA-N 1-[4-[[4-[[7-[3-fluoro-4-(morpholine-4-carbonyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 YAXAUMXYZWVOAJ-UHFFFAOYSA-N 0.000 claims 1
OGWUQLPLQDWEQF-UHFFFAOYSA-N 1-[4-[[4-[[7-[4-(morpholine-4-carbonyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 OGWUQLPLQDWEQF-UHFFFAOYSA-N 0.000 claims 1
PMBLVMPZLVVISO-UHFFFAOYSA-N 1-[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 PMBLVMPZLVVISO-UHFFFAOYSA-N 0.000 claims 1
RSDXHKCZVHZTDK-UHFFFAOYSA-N 1-[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-3-methylpyridin-2-yl]-3,3-dimethylpiperazin-2-one Chemical compound C=1N=C(N2C(C(C)(C)NCC2)=O)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 RSDXHKCZVHZTDK-UHFFFAOYSA-N 0.000 claims 1
QGIAKOQXBTWSPM-UHFFFAOYSA-N 1-[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-3-methylpyridin-2-yl]piperazin-2-one Chemical compound C=1N=C(N2C(CNCC2)=O)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 QGIAKOQXBTWSPM-UHFFFAOYSA-N 0.000 claims 1
PNSKOAJGWOCIDJ-UHFFFAOYSA-N 1-[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-3,3-dimethylpiperazin-2-one Chemical compound O=C1C(C)(C)NCCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 PNSKOAJGWOCIDJ-UHFFFAOYSA-N 0.000 claims 1
LXCWKPVNFAMEGH-UHFFFAOYSA-N 1-[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]piperazin-2-one Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)N4C(CNCC4)=O)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 LXCWKPVNFAMEGH-UHFFFAOYSA-N 0.000 claims 1
CXXRTEBLGXOYJK-UHFFFAOYSA-N 1-[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 CXXRTEBLGXOYJK-UHFFFAOYSA-N 0.000 claims 1
VRDHFYDHSAWOTD-UHFFFAOYSA-N 1-[[2,6-difluoro-4-[2-[4-methyl-3-(piperazin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1=C(CN2CCNCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCCC1=O VRDHFYDHSAWOTD-UHFFFAOYSA-N 0.000 claims 1
XKHWWALXAKXYBF-UHFFFAOYSA-N 1-[[2-chloro-5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]azetidin-3-ol Chemical compound C1C(O)CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1Cl XKHWWALXAKXYBF-UHFFFAOYSA-N 0.000 claims 1
LOEPAKNEKYAGBS-BGYRXZFFSA-N 1-[[4-[2-[4-[[(3s,5r)-3,5-dimethylpiperazin-1-yl]methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]pyrrolidin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4C(CCC4)=O)=C(F)C=3)C2=N1 LOEPAKNEKYAGBS-BGYRXZFFSA-N 0.000 claims 1
DVULOZGYJPEQRO-HDICACEKSA-N 1-[[4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]pyrrolidin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4C(CCC4)=O)=C(F)C=3)C2=N1 DVULOZGYJPEQRO-HDICACEKSA-N 0.000 claims 1
VWRSSVPIDKGWIA-UHFFFAOYSA-N 1-[[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-2-one Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5C(CNCC5)=O)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 VWRSSVPIDKGWIA-UHFFFAOYSA-N 0.000 claims 1
YZAHYUPNFZUGHH-UHFFFAOYSA-N 1-[[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]methyl]piperazin-2-one Chemical compound FC1=CC(N2C3=NC(NC=4C=C(CN5C(CNCC5)=O)N=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 YZAHYUPNFZUGHH-UHFFFAOYSA-N 0.000 claims 1
VRAGZHOCJGQKGK-UHFFFAOYSA-N 1-[[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 VRAGZHOCJGQKGK-UHFFFAOYSA-N 0.000 claims 1
RWSBQPSKBYYJGJ-UHFFFAOYSA-N 1-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]-4-methylpiperazin-2-one Chemical compound O=C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C RWSBQPSKBYYJGJ-UHFFFAOYSA-N 0.000 claims 1
JNWNKSOPFAUSND-UHFFFAOYSA-N 1-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]azetidin-3-ol Chemical compound C1=C(CN2CC(O)C2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 JNWNKSOPFAUSND-UHFFFAOYSA-N 0.000 claims 1
MDYSSELHUKQITE-UHFFFAOYSA-N 1-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]piperazin-2-one Chemical compound C1=C(CN2C(CNCC2)=O)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 MDYSSELHUKQITE-UHFFFAOYSA-N 0.000 claims 1
DAZGQHPCQVIKSH-UHFFFAOYSA-N 1-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]pyrrolidin-3-ol Chemical compound C1=C(CN2CC(O)CC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 DAZGQHPCQVIKSH-UHFFFAOYSA-N 0.000 claims 1
FGHOQIYLCJSETL-UHFFFAOYSA-N 1-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 FGHOQIYLCJSETL-UHFFFAOYSA-N 0.000 claims 1
FRRYQSNQFMTSEO-UHFFFAOYSA-N 1-methyl-4-[[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-2-one Chemical compound C1C(=O)N(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 FRRYQSNQFMTSEO-UHFFFAOYSA-N 0.000 claims 1
CYROSCMUZZKGSJ-UHFFFAOYSA-N 1-methyl-5-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-3h-indol-2-one Chemical compound C=1C=C2N(C)C(=O)CC2=CC=1N(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCN(C)CC1 CYROSCMUZZKGSJ-UHFFFAOYSA-N 0.000 claims 1
IECMLRGWOVNYNJ-UHFFFAOYSA-N 1-morpholin-4-yl-2-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCOCC4)=CC=3)C2=N1 IECMLRGWOVNYNJ-UHFFFAOYSA-N 0.000 claims 1
ZUDXHUHKFTZATM-UHFFFAOYSA-N 1-morpholin-4-yl-2-[4-[2-[4-(trifluoromethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCOCC4)=CC=3)C2=N1 ZUDXHUHKFTZATM-UHFFFAOYSA-N 0.000 claims 1
ZKPMTAPIAIXGAG-UHFFFAOYSA-N 2,6-difluoro-4-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]benzonitrile Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C#N)=C(F)C=3)C2=N1 ZKPMTAPIAIXGAG-UHFFFAOYSA-N 0.000 claims 1
UYZWYSGPLXMBAD-HHHXNRCGSA-N 2-[(3s)-3-[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]morpholin-4-yl]ethanol Chemical compound OCCN1CCOC[C@@H]1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 UYZWYSGPLXMBAD-HHHXNRCGSA-N 0.000 claims 1
RRVOUPZOYGPIQA-UHFFFAOYSA-N 2-[1-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]pyrazol-4-yl]ethanol Chemical compound C1=C(CN2N=CC(CCO)=C2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 RRVOUPZOYGPIQA-UHFFFAOYSA-N 0.000 claims 1
JPOZDZXAYLGAFW-UHFFFAOYSA-N 2-[3-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-1-(4-ethylpiperazin-1-yl)ethanone Chemical compound C1CN(CC)CCN1C(=O)CC1=CC=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 JPOZDZXAYLGAFW-UHFFFAOYSA-N 0.000 claims 1
JIZIXEXRHFVGBM-UHFFFAOYSA-N 2-[4-(2-anilinopyrrolo[2,3-d]pyrimidin-7-yl)phenyl]-1-morpholin-4-ylethanone Chemical compound C1COCCN1C(=O)CC(C=C1)=CC=C1N(C1=N2)C=CC1=CN=C2NC1=CC=CC=C1 JIZIXEXRHFVGBM-UHFFFAOYSA-N 0.000 claims 1
ZDKMPZXYNAUHNQ-UHFFFAOYSA-N 2-[4-[2-(3,4-diethoxyanilino)-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C=C(C)N2C=3C=CC(CC(=O)N4CCN(C)CC4)=CC=3)C2=N1 ZDKMPZXYNAUHNQ-UHFFFAOYSA-N 0.000 claims 1
JZZJUONPBMZNBX-UHFFFAOYSA-N 2-[4-[2-(3,4-diethoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-(4-ethylpiperazin-1-yl)ethanone Chemical compound C1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCN(CC)CC4)=CC=3)C2=N1 JZZJUONPBMZNBX-UHFFFAOYSA-N 0.000 claims 1
HBRDSZQCUVOEPA-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethylanilino)-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=C(N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2C)C=C1 HBRDSZQCUVOEPA-UHFFFAOYSA-N 0.000 claims 1
JPEJFSUMPUBHHI-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=C(N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2)C=C1 JPEJFSUMPUBHHI-UHFFFAOYSA-N 0.000 claims 1
VKUJVIDTBIALIX-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-[4-(2-hydroxyethyl)piperazin-1-yl]ethanone Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCN(CCO)CC4)=CC=3)C2=N1 VKUJVIDTBIALIX-UHFFFAOYSA-N 0.000 claims 1
VMTWUEPMRJCHHK-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCOCC4)=CC=3)C2=N1 VMTWUEPMRJCHHK-UHFFFAOYSA-N 0.000 claims 1
PEUSXSAVICUVQS-UHFFFAOYSA-N 2-[4-[2-(4-fluoro-3-methoxyanilino)-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1=C(F)C(OC)=CC(NC=2N=C3N(C=4C=CC(CC(=O)N5CCN(C)CC5)=CC=4)C(C)=CC3=CN=2)=C1 PEUSXSAVICUVQS-UHFFFAOYSA-N 0.000 claims 1
WQESVXRTDYODQD-UHFFFAOYSA-N 2-[4-[2-(4-fluoro-3-methoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1=C(F)C(OC)=CC(NC=2N=C3N(C=4C=CC(CC(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=C1 WQESVXRTDYODQD-UHFFFAOYSA-N 0.000 claims 1
PSKPYVVAPZQGPY-UHFFFAOYSA-N 2-[4-[2-(4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=C(N2C3=NC(NC=4C=CC(C)=CC=4)=NC=C3C=C2)C=C1 PSKPYVVAPZQGPY-UHFFFAOYSA-N 0.000 claims 1
MAKBMMPLTXGMMN-UHFFFAOYSA-N 2-[4-[2-(4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1=CC(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCOCC4)=CC=3)C2=N1 MAKBMMPLTXGMMN-UHFFFAOYSA-N 0.000 claims 1
QPIOAAPNGSPGDP-UHFFFAOYSA-N 2-[4-[2-[(1-methylpyrazol-4-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCOCC4)=CC=3)C2=N1 QPIOAAPNGSPGDP-UHFFFAOYSA-N 0.000 claims 1
NRUVGHMOFUOBDF-UHFFFAOYSA-N 2-[4-[2-[4-(4-ethylpiperazin-1-yl)-3-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(CC)CCN1C(C(=C1)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CC(=O)N4CCN(C)CC4)=CC=3)C2=N1 NRUVGHMOFUOBDF-UHFFFAOYSA-N 0.000 claims 1
OYPDGHMKNPSGAB-UHFFFAOYSA-N 2-[4-[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 OYPDGHMKNPSGAB-UHFFFAOYSA-N 0.000 claims 1
FRXNZGGUADDFOM-UHFFFAOYSA-N 2-[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]oxyethanol Chemical compound C1=NC(OCCO)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 FRXNZGGUADDFOM-UHFFFAOYSA-N 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
URJDUNGOYVVLLZ-UHFFFAOYSA-N 2-methoxy-5-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 URJDUNGOYVVLLZ-UHFFFAOYSA-N 0.000 claims 1
ZARCEQHYYZPLLE-UHFFFAOYSA-N 2-methyl-1-morpholin-4-yl-2-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]propan-1-one Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(C)(C)C(=O)N3CCOCC3)C2=N1 ZARCEQHYYZPLLE-UHFFFAOYSA-N 0.000 claims 1
VUHKLVXLLPSBCD-UHFFFAOYSA-N 3-[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-2,3,4,6,7,8-hexahydropyrido[1,2-a]pyrazin-1-one Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)C4NC(=O)C5=CCCCN5C4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 VUHKLVXLLPSBCD-UHFFFAOYSA-N 0.000 claims 1
GRBSFYSRJMAKSE-UHFFFAOYSA-N 3-methyl-4-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]benzonitrile Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C(=CC(=CC=3)C#N)C)C2=N1 GRBSFYSRJMAKSE-UHFFFAOYSA-N 0.000 claims 1
NVQTZTHJNOSXPR-UHFFFAOYSA-N 3-methyl-n-[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]-1,2,4,4a,5,7-hexahydropyrazino[1,2-a][4,1]benzoxazepin-9-amine Chemical compound C1N(C)CCN(C2=CC=3)C1COCC2=CC=3NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 NVQTZTHJNOSXPR-UHFFFAOYSA-N 0.000 claims 1
DLRQWPVFIAHLIZ-UHFFFAOYSA-N 4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluoro-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)NCCN4CCOCC4)=CC=3)C2=N1 DLRQWPVFIAHLIZ-UHFFFAOYSA-N 0.000 claims 1
NTIYQKDOFFEMEV-UHFFFAOYSA-N 4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]benzonitrile Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C#N)C2=N1 NTIYQKDOFFEMEV-UHFFFAOYSA-N 0.000 claims 1
NSEKAHACLDNHOK-UHFFFAOYSA-N 4-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(N)(=O)=O)C2=N1 NSEKAHACLDNHOK-UHFFFAOYSA-N 0.000 claims 1
BTHQLXHPMHHDJX-UHFFFAOYSA-N 4-[2-[4-methyl-3-[(4-methylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(N)(=O)=O)C=CC3=CN=2)=CC=C1C BTHQLXHPMHHDJX-UHFFFAOYSA-N 0.000 claims 1
IXDZSFMQRZGFMC-UHFFFAOYSA-N 4-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]benzonitrile Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C#N)C2=N1 IXDZSFMQRZGFMC-UHFFFAOYSA-N 0.000 claims 1
GWUGZTYFQQJIFV-JKSUJKDBSA-N 4-[2-[[6-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C[C@@H]1CN[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(N)(=O)=O)C2=N1 GWUGZTYFQQJIFV-JKSUJKDBSA-N 0.000 claims 1
FKBOGWCTLSHHPJ-IYBDPMFKSA-N 4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(N)(=O)=O)C2=N1 FKBOGWCTLSHHPJ-IYBDPMFKSA-N 0.000 claims 1
MKNQBGPWGUGWRE-UHFFFAOYSA-N 4-[3-chloro-5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]piperazin-2-one Chemical compound FC1=CC(N2C3=NC(NC=4C=C(Cl)C(N5CC(=O)NCC5)=NC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 MKNQBGPWGUGWRE-UHFFFAOYSA-N 0.000 claims 1
LNVJZKRDORORLW-UHFFFAOYSA-N 4-[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 LNVJZKRDORORLW-UHFFFAOYSA-N 0.000 claims 1
MCIDRQYWAUICRS-UHFFFAOYSA-N 4-[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]piperazin-2-one Chemical compound FC1=CC(N2C3=NC(NC=4C=C(N=CC=4)N4CC(=O)NCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 MCIDRQYWAUICRS-UHFFFAOYSA-N 0.000 claims 1
LUCQUCIFVPYOGG-UHFFFAOYSA-N 4-[[2,6-difluoro-4-[2-(4-fluoro-3-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]-1-ethylpiperazin-2-one Chemical compound C1C(=O)N(CC)CCN1CC1=C(F)C=C(N2C3=NC(NC=4C=C(C)C(F)=CC=4)=NC=C3C=C2)C=C1F LUCQUCIFVPYOGG-UHFFFAOYSA-N 0.000 claims 1
GXYHWBHVLYGQEJ-UHFFFAOYSA-N 4-[[2,6-difluoro-4-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]piperazin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CC(=O)NCC4)=C(F)C=3)C2=N1 GXYHWBHVLYGQEJ-UHFFFAOYSA-N 0.000 claims 1
PWAXHJGMPYEDHA-UHFFFAOYSA-N 4-[[2,6-difluoro-4-[2-[4-methyl-3-(morpholin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]piperazin-2-one Chemical compound C1=C(CN2CCOCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCNC(=O)C1 PWAXHJGMPYEDHA-UHFFFAOYSA-N 0.000 claims 1
JYDFXSHRCZUMFZ-UHFFFAOYSA-N 4-[[2,6-difluoro-4-[2-[4-methyl-3-(piperazin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]morpholin-3-one Chemical compound C1=C(CN2CCNCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1=O JYDFXSHRCZUMFZ-UHFFFAOYSA-N 0.000 claims 1
VOBZAWUYUOCSDO-UHFFFAOYSA-N 4-[[2,6-difluoro-4-[2-[4-methyl-3-(piperazin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]piperazin-2-one Chemical compound C1=C(CN2CCNCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCNC(=O)C1 VOBZAWUYUOCSDO-UHFFFAOYSA-N 0.000 claims 1
CFAGAECHVDZABT-UHFFFAOYSA-N 4-[[2,6-difluoro-4-[2-[4-methyl-3-[(4-methylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]piperazin-2-one Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CC(=O)NCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C CFAGAECHVDZABT-UHFFFAOYSA-N 0.000 claims 1
FLMKBEFFCWYHMC-UHFFFAOYSA-N 4-[[4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]piperazin-2-one Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CC(=O)NCC4)=C(F)C=3)C2=N1 FLMKBEFFCWYHMC-UHFFFAOYSA-N 0.000 claims 1
FZAUBDQSSCQHGN-UHFFFAOYSA-N 4-[[4-[2-[4-[(4-acetylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]piperazin-2-one Chemical compound C1CN(C(=O)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CC(=O)NCC4)=C(F)C=3)C2=N1 FZAUBDQSSCQHGN-UHFFFAOYSA-N 0.000 claims 1
PPGQVVNSAXJEDL-UHFFFAOYSA-N 4-[[4-[2-[4-[(4-cyclopropylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]piperazin-2-one Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CCN(CC5)C5CC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCNC(=O)C1 PPGQVVNSAXJEDL-UHFFFAOYSA-N 0.000 claims 1
KSBRMLGQPKTSET-BGYRXZFFSA-N 4-[[4-[2-[4-[[(3r,5s)-3,5-dimethylpiperazin-1-yl]methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]morpholin-3-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4C(COCC4)=O)=C(F)C=3)C2=N1 KSBRMLGQPKTSET-BGYRXZFFSA-N 0.000 claims 1
QPXPVWVSNZRZMF-KDURUIRLSA-N 4-[[4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-5-methylpyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]morpholin-3-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C(=C1)C)=NC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4C(COCC4)=O)=C(F)C=3)C2=N1 QPXPVWVSNZRZMF-KDURUIRLSA-N 0.000 claims 1
XLUXJTSFFNALDM-HDICACEKSA-N 4-[[4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]methyl]piperazin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CC(=O)NCC4)=C(F)C=3)C2=N1 XLUXJTSFFNALDM-HDICACEKSA-N 0.000 claims 1
ZLTAGJAGPIRSMQ-UHFFFAOYSA-N 4-[[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]methyl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 ZLTAGJAGPIRSMQ-UHFFFAOYSA-N 0.000 claims 1
IBGNEADLGVZQAR-UHFFFAOYSA-N 4-[[4-[[7-[3,5-difluoro-4-(morpholine-4-carbonyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazin-2-one Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CC(=O)NCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 IBGNEADLGVZQAR-UHFFFAOYSA-N 0.000 claims 1
BYWGGKVBBSLDKZ-UHFFFAOYSA-N 4-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]-1-[2-(dimethylamino)ethyl]piperazin-2-one Chemical compound C1C(=O)N(CCN(C)C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C BYWGGKVBBSLDKZ-UHFFFAOYSA-N 0.000 claims 1
XZPGLOLMCOVBJK-UHFFFAOYSA-N 4-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C XZPGLOLMCOVBJK-UHFFFAOYSA-N 0.000 claims 1
KHAROAQXNHICTQ-UHFFFAOYSA-N 4-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]piperazin-2-one Chemical compound C1=C(CN2CC(=O)NCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 KHAROAQXNHICTQ-UHFFFAOYSA-N 0.000 claims 1
FHAXOUPREBJBFN-UHFFFAOYSA-N 4-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]piperazine-1-carbaldehyde Chemical compound C1=C(CN2CCN(CC2)C=O)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 FHAXOUPREBJBFN-UHFFFAOYSA-N 0.000 claims 1
OWHUISMTHRKCDB-UHFFFAOYSA-N 4-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]methyl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1CC(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 OWHUISMTHRKCDB-UHFFFAOYSA-N 0.000 claims 1
MACSHMUYIMTCRV-UHFFFAOYSA-N 4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C(=O)NCCN3CCOCC3)=NC=C2C=C1 MACSHMUYIMTCRV-UHFFFAOYSA-N 0.000 claims 1
RAIBKHJXROVYFM-UHFFFAOYSA-N 4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C#N)=NC=C2C=C1 RAIBKHJXROVYFM-UHFFFAOYSA-N 0.000 claims 1
WXOKXMOJSKYNHL-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)C#N)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 WXOKXMOJSKYNHL-UHFFFAOYSA-N 0.000 claims 1
DKOWNQSWRQJJGK-UHFFFAOYSA-N 4-[[7-[4-(morpholine-4-carbonyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound C=1C=C(N2C3=NC(NC=4C=CC(=CC=4)C#N)=NC=C3C=C2)C=CC=1C(=O)N1CCOCC1 DKOWNQSWRQJJGK-UHFFFAOYSA-N 0.000 claims 1
OZQITGSSHSJETB-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 OZQITGSSHSJETB-UHFFFAOYSA-N 0.000 claims 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
CLCCMTRRMOBGNP-KDURUIRLSA-N 5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridine-3-carbonitrile Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C(=C1)C#N)=NC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 CLCCMTRRMOBGNP-KDURUIRLSA-N 0.000 claims 1
YCBWJFFVAHJEPP-UHFFFAOYSA-N 5-[[7-[3-fluoro-4-(morpholine-4-carbonyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridine-2-carbonitrile Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)C#N)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 YCBWJFFVAHJEPP-UHFFFAOYSA-N 0.000 claims 1
SYHJOXSXWZFFAK-UHFFFAOYSA-N 5-[[7-[4-(morpholine-4-carbonyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridine-2-carbonitrile Chemical compound C=1C=C(N2C3=NC(NC=4C=NC(=CC=4)C#N)=NC=C3C=C2)C=CC=1C(=O)N1CCOCC1 SYHJOXSXWZFFAK-UHFFFAOYSA-N 0.000 claims 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 1
VAVFPENJFDYELW-KDURUIRLSA-N 6-[2-[4-[[(3s,5r)-3,5-dimethylpiperazin-1-yl]methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C4CCC(=O)NC4=CC=3)C2=N1 VAVFPENJFDYELW-KDURUIRLSA-N 0.000 claims 1
KPGJOJFGLICEQQ-GASCZTMLSA-N 7-(3,5-difluorophenyl)-n-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C=C(F)C=3)C2=N1 KPGJOJFGLICEQQ-GASCZTMLSA-N 0.000 claims 1
JMIKTMGRUMIBQY-UHFFFAOYSA-N 7-(3-fluoro-4-methylsulfonylphenyl)-n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(=CC=3)S(C)(=O)=O)C2=N1 JMIKTMGRUMIBQY-UHFFFAOYSA-N 0.000 claims 1
MKZFCJSPLRTIKK-UHFFFAOYSA-N 7-(4-ethylphenyl)-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1=CC(CC)=CC=C1N1C2=NC(NC=3C=NC(=CC=3)N3CCN(C)CC3)=NC=C2C=C1 MKZFCJSPLRTIKK-UHFFFAOYSA-N 0.000 claims 1
LWUYJJXNUFTJQV-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-(2,2,3,3-tetrafluoro-1,4-benzodioxin-6-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C4OC(F)(F)C(F)(F)OC4=CC=3)=NC=C2C=C1 LWUYJJXNUFTJQV-UHFFFAOYSA-N 0.000 claims 1
UTYNTJKJFKNOEL-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-(3,4,5-trimethoxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 UTYNTJKJFKNOEL-UHFFFAOYSA-N 0.000 claims 1
LIQABDVYFKDYPV-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-(4-piperazin-1-ylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C=C1 LIQABDVYFKDYPV-UHFFFAOYSA-N 0.000 claims 1
YEOYOYFJRCROLY-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 YEOYOYFJRCROLY-UHFFFAOYSA-N 0.000 claims 1
LJUOAHIFXRIJED-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-(4-pyrrolidin-2-ylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C3NCCC3)=NC=C2C=C1 LJUOAHIFXRIJED-UHFFFAOYSA-N 0.000 claims 1
MBFMWGMJDSKMRR-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-(6-piperazin-1-ylpyridin-3-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=NC(=CC=3)N3CCNCC3)=NC=C2C=C1 MBFMWGMJDSKMRR-UHFFFAOYSA-N 0.000 claims 1
BNSOQHQGPGYQPT-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-[3-(2-morpholin-4-ylethoxy)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C(OCCN4CCOCC4)C=CC=3)=NC=C2C=C1 BNSOQHQGPGYQPT-UHFFFAOYSA-N 0.000 claims 1
IMHMHICTHCYQOB-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-[3-(piperidin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C(CN4CCCCC4)C=CC=3)=NC=C2C=C1 IMHMHICTHCYQOB-UHFFFAOYSA-N 0.000 claims 1
VCZUVDKWGIEPSN-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-[4-(2-morpholin-4-ylethoxy)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(OCCN4CCOCC4)=CC=3)=NC=C2C=C1 VCZUVDKWGIEPSN-UHFFFAOYSA-N 0.000 claims 1
BKWWNLDQYQYNSB-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-[4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(CN4CCOCC4)=CC=3)=NC=C2C=C1 BKWWNLDQYQYNSB-UHFFFAOYSA-N 0.000 claims 1
PJIVXPRATCFTSQ-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-[4-(piperazin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(CN4CCNCC4)=CC=3)=NC=C2C=C1 PJIVXPRATCFTSQ-UHFFFAOYSA-N 0.000 claims 1
XAZIEVWHTYPCFB-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-[4-(piperidin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(CN4CCCCC4)=CC=3)=NC=C2C=C1 XAZIEVWHTYPCFB-UHFFFAOYSA-N 0.000 claims 1
VYYGRROKLJVRAU-UHFFFAOYSA-N 7-(4-methylsulfonylphenyl)-n-phenylpyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC=CC=3)=NC=C2C=C1 VYYGRROKLJVRAU-UHFFFAOYSA-N 0.000 claims 1
YYJQZMPTGMOTLB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(methoxymethyl)phenyl]-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(F)C(COC)=C(F)C=C1N1C2=NC(NC=3C=NC(=CC=3)N3CCN(C)CC3)=NC=C2C=C1 YYJQZMPTGMOTLB-UHFFFAOYSA-N 0.000 claims 1
YQPNDCJKVAVWBA-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(1-methylpyrazol-4-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=NN(C)C=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 YQPNDCJKVAVWBA-UHFFFAOYSA-N 0.000 claims 1
OYGGMEBPSCOTBB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(1-piperidin-4-ylpyrazol-4-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC4=CN(N=C4)C4CCNCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 OYGGMEBPSCOTBB-UHFFFAOYSA-N 0.000 claims 1
ZFMQCMHCYFUKHU-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(2,3-dihydro-1h-indol-6-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C5NCCC5=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 ZFMQCMHCYFUKHU-UHFFFAOYSA-N 0.000 claims 1
ZERVEXYJDKALTE-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(3,4-dimethylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 ZERVEXYJDKALTE-UHFFFAOYSA-N 0.000 claims 1
KGCDMMHUYBIYQL-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(3-methoxy-4-methylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1=C(C)C(OC)=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 KGCDMMHUYBIYQL-UHFFFAOYSA-N 0.000 claims 1
NSJGXXICGGPEFO-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(4-fluoro-3-methylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1=C(F)C(C)=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 NSJGXXICGGPEFO-UHFFFAOYSA-N 0.000 claims 1
GSGFRBKSEJRLAJ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(4-methylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 GSGFRBKSEJRLAJ-UHFFFAOYSA-N 0.000 claims 1
JJCBFRIXUKDPFO-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(4-morpholin-2-ylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)C4OCCNC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 JJCBFRIXUKDPFO-UHFFFAOYSA-N 0.000 claims 1
SHNBTEBXPGLIPL-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 SHNBTEBXPGLIPL-UHFFFAOYSA-N 0.000 claims 1
GEDVLGWXVYCSIN-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(6-piperazin-1-ylpyridin-3-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)N4CCNCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 GEDVLGWXVYCSIN-UHFFFAOYSA-N 0.000 claims 1
ANVXUEQVIAPQBW-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(6-pyrrolidin-3-yloxypyridin-3-yl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(OC5CNCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 ANVXUEQVIAPQBW-UHFFFAOYSA-N 0.000 claims 1
INJCTNWXFNPVRK-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[1-(2-methoxyethyl)pyrazol-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=NN(CCOC)C=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 INJCTNWXFNPVRK-UHFFFAOYSA-N 0.000 claims 1
SDIJUTLWQQYTGQ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-(2-morpholin-4-ylethoxy)pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(OCCN5CCOCC5)N=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 SDIJUTLWQQYTGQ-UHFFFAOYSA-N 0.000 claims 1
SWPRGBHQIXPJDL-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-(oxan-4-yloxy)pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(OC5CCOCC5)N=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 SWPRGBHQIXPJDL-UHFFFAOYSA-N 0.000 claims 1
IWRMQCZVBSLZLC-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-(piperazin-1-ylmethyl)pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(CN5CCNCC5)N=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 IWRMQCZVBSLZLC-UHFFFAOYSA-N 0.000 claims 1
BLRQYFZJVWDLJB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-(piperidin-4-ylmethoxy)pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(OCC5CCNCC5)N=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 BLRQYFZJVWDLJB-UHFFFAOYSA-N 0.000 claims 1
HJSWJCUVUUYJRP-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-[(3,3-difluoropyrrolidin-1-yl)methyl]pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(CN5CC(F)(F)CC5)N=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 HJSWJCUVUUYJRP-UHFFFAOYSA-N 0.000 claims 1
MMPZTCRHRDDRJB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-[(3-methoxypyrrolidin-1-yl)methyl]pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1C(OC)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 MMPZTCRHRDDRJB-UHFFFAOYSA-N 0.000 claims 1
UXCSKKGMKJNARV-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-[(4-methylpiperazin-1-yl)methyl]pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 UXCSKKGMKJNARV-UHFFFAOYSA-N 0.000 claims 1
HRGWBOUXHGHIAZ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-[3-(trifluoromethyl)piperazin-1-yl]pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(N=CC=4)N4CC(NCC4)C(F)(F)F)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 HRGWBOUXHGHIAZ-UHFFFAOYSA-N 0.000 claims 1
UDIGDLGWNVKRIA-BGYRXZFFSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-[[(3r,5s)-3,5-dimethylpiperazin-1-yl]methyl]pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 UDIGDLGWNVKRIA-BGYRXZFFSA-N 0.000 claims 1
PKGDNUXRTPIGIM-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1C(N(C)C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 PKGDNUXRTPIGIM-UHFFFAOYSA-N 0.000 claims 1
BPJDJDAZAGZTBP-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[2-[[4-[2-(dimethylamino)ethyl]piperazin-1-yl]methyl]pyridin-4-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CCN(C)C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 BPJDJDAZAGZTBP-UHFFFAOYSA-N 0.000 claims 1
UPSYYBWNXLGHAQ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3,5-dimethyl-4-(2-morpholin-4-ylethoxy)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C=1C(C)=C(OCCN2CCOCC2)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 UPSYYBWNXLGHAQ-UHFFFAOYSA-N 0.000 claims 1
NUHMXOOOGYPPRH-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-(2,5-dioxa-8-azaspiro[3.5]nonan-8-ylmethyl)-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CC3(COC3)OCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 NUHMXOOOGYPPRH-UHFFFAOYSA-N 0.000 claims 1
NDGJEEIAORALKZ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-(4-methylpiperazin-1-yl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 NDGJEEIAORALKZ-UHFFFAOYSA-N 0.000 claims 1
FXCIXLRKAABTOV-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-(imidazol-1-ylmethyl)-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2C=NC=C2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 FXCIXLRKAABTOV-UHFFFAOYSA-N 0.000 claims 1
OVZWHLPEAPCPDX-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical class FC1=CC(N2C3=NC(NC=4C=C(CN5CCOCC5)C=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 OVZWHLPEAPCPDX-UHFFFAOYSA-N 0.000 claims 1
SXIXOXIQQSYZNX-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[(3,3-difluoropyrrolidin-1-yl)methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CC(F)(F)CC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 SXIXOXIQQSYZNX-UHFFFAOYSA-N 0.000 claims 1
DUIHFLHPTPUYSO-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[(3-methoxyazetidin-1-yl)methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1C(OC)CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C DUIHFLHPTPUYSO-UHFFFAOYSA-N 0.000 claims 1
VNLHUNMGXFNZFO-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[(3-methoxypyrrolidin-1-yl)methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1C(OC)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C VNLHUNMGXFNZFO-UHFFFAOYSA-N 0.000 claims 1
UUXWRGMJRPKZQT-RUZDIDTESA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[(3s)-morpholin-3-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(C=CC=4)[C@@H]4NCCOC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 UUXWRGMJRPKZQT-RUZDIDTESA-N 0.000 claims 1
VMJCXYYKLYFMCX-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=CC=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 VMJCXYYKLYFMCX-UHFFFAOYSA-N 0.000 claims 1
XVFKQYAPWMMAJZ-FCHUYYIVSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[[(2r,5s)-2,5-dimethylpiperazin-1-yl]methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C[C@@H]1CN[C@@H](C)CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C XVFKQYAPWMMAJZ-FCHUYYIVSA-N 0.000 claims 1
QPKFEQDYHJDNTI-SZPZYZBQSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[[(3r,5s)-3,5-dimethylpiperazin-1-yl]methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C QPKFEQDYHJDNTI-SZPZYZBQSA-N 0.000 claims 1
PMQDNWDXYNDDOZ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1C(N(C)C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C PMQDNWDXYNDDOZ-UHFFFAOYSA-N 0.000 claims 1
UQJOKJZHSCAGQL-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[[4-[(dimethylamino)methyl]triazol-1-yl]methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound N1=NC(CN(C)C)=CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C UQJOKJZHSCAGQL-UHFFFAOYSA-N 0.000 claims 1
ULJCNLMWYADRAY-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-[[4-[2-(dimethylamino)ethyl]piperazin-1-yl]methyl]-4-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CCN(C)C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C ULJCNLMWYADRAY-UHFFFAOYSA-N 0.000 claims 1
ODIRXAWWCNUONZ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-methyl-4-(piperazin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C=1C=C(CN2CCNCC2)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 ODIRXAWWCNUONZ-UHFFFAOYSA-N 0.000 claims 1
CYZNTUWPWHPOIL-AREMUKBSSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[3-methyl-4-[(2r)-pyrrolidin-2-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C=1C=C([C@@H]2NCCC2)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 CYZNTUWPWHPOIL-AREMUKBSSA-N 0.000 claims 1
PCVCDGCQJIYNET-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-(methoxymethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(COC)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 PCVCDGCQJIYNET-UHFFFAOYSA-N 0.000 claims 1
JRSBKRKJRJSVGB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical class FC1=CC(N2C3=NC(NC=4C=CC(CN5CCOCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 JRSBKRKJRJSVGB-UHFFFAOYSA-N 0.000 claims 1
HOPKFHYFYOKONN-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-(piperazin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical class FC1=CC(N2C3=NC(NC=4C=CC(CN5CCNCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 HOPKFHYFYOKONN-UHFFFAOYSA-N 0.000 claims 1
LKPLZNBGPJVUKG-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-(piperidin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical class FC1=CC(N2C3=NC(NC=4C=CC(CC5CCNCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 LKPLZNBGPJVUKG-UHFFFAOYSA-N 0.000 claims 1
UKZLPVBTMYQBDP-VWLOTQADSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(2r)-piperazin-2-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)[C@H]4NCCNC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 UKZLPVBTMYQBDP-VWLOTQADSA-N 0.000 claims 1
UKZLPVBTMYQBDP-RUZDIDTESA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(2s)-piperazin-2-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)[C@@H]4NCCNC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 UKZLPVBTMYQBDP-RUZDIDTESA-N 0.000 claims 1
AVUHWICIPLXTIF-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(3,3-difluoropyrrolidin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CC(F)(F)CC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 AVUHWICIPLXTIF-UHFFFAOYSA-N 0.000 claims 1
WVFZXUBUIGYQFM-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(3,3-dimethylpiperazin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CNC(C)(C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 WVFZXUBUIGYQFM-UHFFFAOYSA-N 0.000 claims 1
PBQWTOHFZDSHOH-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(3-methoxypyrrolidin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1C(OC)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 PBQWTOHFZDSHOH-UHFFFAOYSA-N 0.000 claims 1
QFGWESUFQFHJIO-UUWRZZSWSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(3s)-4-(2-phenylmethoxyethyl)morpholin-3-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)[C@@H]4N(CCOC4)CCOCC=4C=CC=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 QFGWESUFQFHJIO-UUWRZZSWSA-N 0.000 claims 1
RUWYHWILNOGLGJ-HHHXNRCGSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(3s)-4-ethylmorpholin-3-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound CCN1CCOC[C@@H]1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 RUWYHWILNOGLGJ-HHHXNRCGSA-N 0.000 claims 1
MFISXLSRLIIEMW-AREMUKBSSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(3s)-4-methylmorpholin-3-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound CN1CCOC[C@@H]1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 MFISXLSRLIIEMW-AREMUKBSSA-N 0.000 claims 1
BKXCFBNNBBJFAV-RUZDIDTESA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(3s)-morpholin-3-yl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)[C@@H]4NCCOC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 BKXCFBNNBBJFAV-RUZDIDTESA-N 0.000 claims 1
FYDDWLWCOQAOCM-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 FYDDWLWCOQAOCM-UHFFFAOYSA-N 0.000 claims 1
FWRIDBPPCKUJDS-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 FWRIDBPPCKUJDS-UHFFFAOYSA-N 0.000 claims 1
KCJRFVJKYJXKQM-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 KCJRFVJKYJXKQM-UHFFFAOYSA-N 0.000 claims 1
XQQGZDAWEVRDBY-RTWAWAEBSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[[(2s,5r)-2,5-dimethylpiperazin-1-yl]methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C[C@H]1CN[C@H](C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 XQQGZDAWEVRDBY-RTWAWAEBSA-N 0.000 claims 1
YLLHGMCGGBSWBU-BGYRXZFFSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[[(3r,5s)-3,5-dimethylpiperazin-1-yl]methyl]-2-fluorophenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C=C1F)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 YLLHGMCGGBSWBU-BGYRXZFFSA-N 0.000 claims 1
AQGSMYJRZLBPDE-SZPZYZBQSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[[(3r,5s)-3,5-dimethylpiperazin-1-yl]methyl]-3-methylphenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C(=C1)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 AQGSMYJRZLBPDE-SZPZYZBQSA-N 0.000 claims 1
VBAHEMNBVZLAQO-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-[[3-(trifluoromethyl)piperazin-1-yl]methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CC(NCC5)C(F)(F)F)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 VBAHEMNBVZLAQO-UHFFFAOYSA-N 0.000 claims 1
UUBYJYRTXRTGCO-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-methyl-3-(1,2,4-triazol-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2C=NN=C2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 UUBYJYRTXRTGCO-UHFFFAOYSA-N 0.000 claims 1
QKTBPXRWXWFKAJ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-methyl-3-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C QKTBPXRWXWFKAJ-UHFFFAOYSA-N 0.000 claims 1
JXMYEQPNEJVTLO-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-methyl-3-[(4-methylpyrazol-1-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(C)C=NN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C JXMYEQPNEJVTLO-UHFFFAOYSA-N 0.000 claims 1
QNBJJWYBHWJFMX-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-methyl-3-[(7-methyl-2,7-diazaspiro[4.4]nonan-2-yl)methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1N(C)CCC11CN(CC=2C(=CC=C(NC=3N=C4N(C=5C=C(F)C(CN6CCOCC6)=C(F)C=5)C=CC4=CN=3)C=2)C)CC1 QNBJJWYBHWJFMX-UHFFFAOYSA-N 0.000 claims 1
IHXOSONUNQVOOU-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-methyl-3-[[3-(trifluoromethyl)piperazin-1-yl]methyl]phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CC(NCC2)C(F)(F)F)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 IHXOSONUNQVOOU-UHFFFAOYSA-N 0.000 claims 1
JNHMIORMHINKRT-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[5-(4-methylpiperazin-1-yl)pyridin-2-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C=N1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 JNHMIORMHINKRT-UHFFFAOYSA-N 0.000 claims 1
FZOVJAKRDILXIB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 FZOVJAKRDILXIB-UHFFFAOYSA-N 0.000 claims 1
CBNWGMNGKBLWBI-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-(2-methoxyethoxy)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=NC(OCCOC)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 CBNWGMNGKBLWBI-UHFFFAOYSA-N 0.000 claims 1
YIURKEPSDOVEKA-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-(2-morpholin-4-ylethoxy)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(OCCN5CCOCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 YIURKEPSDOVEKA-UHFFFAOYSA-N 0.000 claims 1
CWZVJVYURNVTIB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-(morpholin-4-ylmethyl)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(CN5CCOCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 CWZVJVYURNVTIB-UHFFFAOYSA-N 0.000 claims 1
KAERNZMGRLYXFZ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-(oxan-4-ylmethoxy)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(OCC5CCOCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 KAERNZMGRLYXFZ-UHFFFAOYSA-N 0.000 claims 1
GCOOWWQEDHHYAS-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-(oxan-4-yloxy)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(OC5CCOCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 GCOOWWQEDHHYAS-UHFFFAOYSA-N 0.000 claims 1
GFMXBXHELYPZKF-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-(piperazin-1-ylmethyl)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(CN5CCNCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 GFMXBXHELYPZKF-UHFFFAOYSA-N 0.000 claims 1
RBJHFPNJARCDIK-RBUKOAKNSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C[C@@H]1CN[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 RBJHFPNJARCDIK-RBUKOAKNSA-N 0.000 claims 1
IXABPYFAQOAGOQ-KDURUIRLSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-5-methoxypyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C=1N=C(N2C[C@@H](C)N[C@@H](C)C2)C(OC)=CC=1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 IXABPYFAQOAGOQ-KDURUIRLSA-N 0.000 claims 1
ZHHXJPIIMJHYDC-BGYRXZFFSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-5-methylpyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C(=C1)C)=NC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 ZHHXJPIIMJHYDC-BGYRXZFFSA-N 0.000 claims 1
FHLBPVUUOMTKLA-HDICACEKSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-5-(trifluoromethyl)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C(=C1)C(F)(F)F)=NC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 FHLBPVUUOMTKLA-HDICACEKSA-N 0.000 claims 1
GSJPRMPLXSEABZ-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 GSJPRMPLXSEABZ-UHFFFAOYSA-N 0.000 claims 1
MRSWHBIQJGZQCB-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[3-(trifluoromethyl)piperazin-1-yl]pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)N4CC(NCC4)C(F)(F)F)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 MRSWHBIQJGZQCB-UHFFFAOYSA-N 0.000 claims 1
RQLDFFLJGVYVEW-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[6-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CCN(C)C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 RQLDFFLJGVYVEW-UHFFFAOYSA-N 0.000 claims 1
JXIXNGUFSRFSJE-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-phenylpyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 JXIXNGUFSRFSJE-UHFFFAOYSA-N 0.000 claims 1
ZZOODPSQDKPXGG-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-pyridin-2-ylpyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4N=CC=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 ZZOODPSQDKPXGG-UHFFFAOYSA-N 0.000 claims 1
FNHXLQBULBOTOD-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-pyridin-3-ylpyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 FNHXLQBULBOTOD-UHFFFAOYSA-N 0.000 claims 1
FFBPUBAEGUIZGH-UHFFFAOYSA-N 7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-pyridin-4-ylpyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CN=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 FFBPUBAEGUIZGH-UHFFFAOYSA-N 0.000 claims 1
ITGZLMJFDJDVDM-UHFFFAOYSA-N 7-[3,5-difluoro-4-(pyrrolidin-1-ylmethyl)phenyl]-n-[4-(methoxymethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(COC)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCCC4)=C(F)C=3)C2=N1 ITGZLMJFDJDVDM-UHFFFAOYSA-N 0.000 claims 1
RVVKKQOMZQQMGJ-UHFFFAOYSA-N 7-[3,5-difluoro-4-[(3-methoxyazetidin-1-yl)methyl]phenyl]-n-[4-methyl-3-(piperazin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1C(OC)CN1CC1=C(F)C=C(N2C3=NC(NC=4C=C(CN5CCNCC5)C(C)=CC=4)=NC=C3C=C2)C=C1F RVVKKQOMZQQMGJ-UHFFFAOYSA-N 0.000 claims 1
JRLBGNFQHCTLAU-UHFFFAOYSA-N 7-[3,5-difluoro-4-[(4-methylpiperazin-1-yl)methyl]phenyl]-n-(3,4-dimethylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=C(F)C=C(N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2)C=C1F JRLBGNFQHCTLAU-UHFFFAOYSA-N 0.000 claims 1
QEAJIQNDLCVJTM-UHFFFAOYSA-N 7-[3,5-difluoro-4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]-n-(3,4-dimethylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C(C)C)CCN1CC1=C(F)C=C(N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2)C=C1F QEAJIQNDLCVJTM-UHFFFAOYSA-N 0.000 claims 1
ZEDLEUPTWVASSA-UHFFFAOYSA-N 7-[3-chloro-4-(morpholin-4-ylmethyl)phenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(Cl)C(CN4CCOCC4)=CC=3)C2=N1 ZEDLEUPTWVASSA-UHFFFAOYSA-N 0.000 claims 1
HXQVJGHIFHBHNG-UHFFFAOYSA-N 7-[3-chloro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-(methoxymethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(COC)=CC=C1NC1=NC=C(C=CN2C=3C=C(Cl)C(CN4CCOCC4)=CC=3)C2=N1 HXQVJGHIFHBHNG-UHFFFAOYSA-N 0.000 claims 1
HSTQWMKWQSGJFX-UHFFFAOYSA-N 7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=CC=3)C2=N1 HSTQWMKWQSGJFX-UHFFFAOYSA-N 0.000 claims 1
SKCOWYCDNROKGI-UHFFFAOYSA-N 7-[3-methyl-4-(morpholin-4-ylmethyl)phenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(C)C(CN4CCOCC4)=CC=3)C2=N1 SKCOWYCDNROKGI-UHFFFAOYSA-N 0.000 claims 1
WMVFCLNFHSREAY-UHFFFAOYSA-N 7-[4-(1-methoxyethyl)phenyl]-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(C(C)OC)=CC=C1N1C2=NC(NC=3C=NC(=CC=3)N3CCN(C)CC3)=NC=C2C=C1 WMVFCLNFHSREAY-UHFFFAOYSA-N 0.000 claims 1
DTAOJUJNSRMHBV-UHFFFAOYSA-N 7-[4-(1-morpholin-4-ylethyl)phenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(C)N3CCOCC3)C2=N1 DTAOJUJNSRMHBV-UHFFFAOYSA-N 0.000 claims 1
MEDMMSMGDWWFIP-UHFFFAOYSA-N 7-[4-(2-morpholin-4-ylethyl)phenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CCN4CCOCC4)=CC=3)C2=N1 MEDMMSMGDWWFIP-UHFFFAOYSA-N 0.000 claims 1
GJHDPKORWWQYCZ-UHFFFAOYSA-N 7-[4-(morpholin-4-ylmethyl)phenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CN4CCOCC4)=CC=3)C2=N1 GJHDPKORWWQYCZ-UHFFFAOYSA-N 0.000 claims 1
IDRBDBABJJSFAJ-UHFFFAOYSA-N 7-[4-[(3,3-dimethylmorpholin-4-yl)methyl]-3,5-difluorophenyl]-n-(3,4-dimethylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4C(COCC4)(C)C)=C(F)C=3)C2=N1 IDRBDBABJJSFAJ-UHFFFAOYSA-N 0.000 claims 1
AXRSMCQJPFJKEJ-UHFFFAOYSA-N 7-[4-[(4-cyclopropylpiperazin-1-yl)methyl]-3,5-difluorophenyl]-n-(3,4-dimethylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCN(CC4)C4CC4)=C(F)C=3)C2=N1 AXRSMCQJPFJKEJ-UHFFFAOYSA-N 0.000 claims 1
ZDFMYERUODLMDI-UHFFFAOYSA-N 7-[4-[(4-ethylpiperazin-1-yl)methyl]-3,5-difluorophenyl]-n-(4-fluoro-3-methylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC1=C(F)C=C(N2C3=NC(NC=4C=C(C)C(F)=CC=4)=NC=C3C=C2)C=C1F ZDFMYERUODLMDI-UHFFFAOYSA-N 0.000 claims 1
AUEXLGAGIGFZLV-UHFFFAOYSA-N 7-[4-[(4-ethylpiperazin-1-yl)methyl]-3-fluorophenyl]-n-(4-fluoro-3-methylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(N2C3=NC(NC=4C=C(C)C(F)=CC=4)=NC=C3C=C2)C=C1F AUEXLGAGIGFZLV-UHFFFAOYSA-N 0.000 claims 1
OVEBBGUVZKSWDR-UHFFFAOYSA-N 7-[4-[(4-ethylpiperazin-1-yl)methyl]-3-fluorophenyl]-n-(4-propan-2-yloxyphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1CN(CC)CCN1CC1=CC=C(N2C3=NC(NC=4C=CC(OC(C)C)=CC=4)=NC=C3C=C2)C=C1F OVEBBGUVZKSWDR-UHFFFAOYSA-N 0.000 claims 1
ZZXQDESBSHAYLM-BGYRXZFFSA-N 7-[4-[[(2r,6s)-2,6-dimethylmorpholin-4-yl]methyl]-3,5-difluorophenyl]-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=C(F)C=C(N2C3=NC(NC=4C=NC(=CC=4)N4CCN(C)CC4)=NC=C3C=C2)C=C1F ZZXQDESBSHAYLM-BGYRXZFFSA-N 0.000 claims 1
SJDMALMPERHIBS-UHFFFAOYSA-N CN(CCNC1CC(C=C2)=CC=C2NC2=NC(N(C=C3)C(C=C4)=CC(F)=C4C(N4CCOCC4)=O)=C3C=N2)C1=O Chemical compound CN(CCNC1CC(C=C2)=CC=C2NC2=NC(N(C=C3)C(C=C4)=CC(F)=C4C(N4CCOCC4)=O)=C3C=N2)C1=O SJDMALMPERHIBS-UHFFFAOYSA-N 0.000 claims 1
UVLJGHLTMFDUAX-UHFFFAOYSA-N FC1=CC(N2C3=NC(NC=4C=C5C6CCC(N6)C5=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 Chemical compound FC1=CC(N2C3=NC(NC=4C=C5C6CCC(N6)C5=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 UVLJGHLTMFDUAX-UHFFFAOYSA-N 0.000 claims 1
VGEYCLQFQULAAQ-UHFFFAOYSA-N [1-[4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]cyclopropyl]-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1(C=2C=CC(=CC=2)N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2)CC1 VGEYCLQFQULAAQ-UHFFFAOYSA-N 0.000 claims 1
QAXGJEKYOOHOLJ-UHFFFAOYSA-N [1-[4-[2-(3-chloro-4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]cyclopropyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1(C=2C=CC(=CC=2)N2C3=NC(NC=4C=C(Cl)C(C)=CC=4)=NC=C3C=C2)CC1 QAXGJEKYOOHOLJ-UHFFFAOYSA-N 0.000 claims 1
MPFISKZYSORNSK-UHFFFAOYSA-N [1-[4-[2-(4-fluoro-3-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]cyclopropyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1(C=2C=CC(=CC=2)N2C3=NC(NC=4C=C(C)C(F)=CC=4)=NC=C3C=C2)CC1 MPFISKZYSORNSK-UHFFFAOYSA-N 0.000 claims 1
OXFGBLCUSKXMST-UHFFFAOYSA-N [1-[[5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]methyl]triazol-4-yl]methanol Chemical compound C1=C(CN2N=NC(CO)=C2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 OXFGBLCUSKXMST-UHFFFAOYSA-N 0.000 claims 1
LVMBZFLXWWJUDA-UHFFFAOYSA-N [2,6-difluoro-4-[2-(1,3-thiazol-2-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4SC=CN=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 LVMBZFLXWWJUDA-UHFFFAOYSA-N 0.000 claims 1
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USYUCOHEHMBSLA-UHFFFAOYSA-N [2,6-difluoro-4-[2-(pyridin-2-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4N=CC=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 USYUCOHEHMBSLA-UHFFFAOYSA-N 0.000 claims 1
KKZWWWBLZNYERB-UHFFFAOYSA-N [2,6-difluoro-4-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=NC=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 KKZWWWBLZNYERB-UHFFFAOYSA-N 0.000 claims 1
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JTLSWOWBAJFMDE-UHFFFAOYSA-N [2,6-difluoro-4-[2-[(1-methylpyrazol-4-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 JTLSWOWBAJFMDE-UHFFFAOYSA-N 0.000 claims 1
WWRVIAHKQVSCHD-UHFFFAOYSA-N [2,6-difluoro-4-[2-[(5-methylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1=CN=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 WWRVIAHKQVSCHD-UHFFFAOYSA-N 0.000 claims 1
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KNULCLMWTZZYDM-UHFFFAOYSA-N [2,6-difluoro-4-[2-[3-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCN1C1=CC=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 KNULCLMWTZZYDM-UHFFFAOYSA-N 0.000 claims 1
FXGZAPSGZKOOGY-UHFFFAOYSA-N [2,6-difluoro-4-[2-[3-[(4-methylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCN1CC1=CC=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 FXGZAPSGZKOOGY-UHFFFAOYSA-N 0.000 claims 1
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MUBGVZBGMUNQHH-UHFFFAOYSA-N [2,6-difluoro-4-[2-[4-(morpholin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(F)C=C(N2C3=NC(NC=4C=CC(CN5CCOCC5)=CC=4)=NC=C3C=C2)C=C1F MUBGVZBGMUNQHH-UHFFFAOYSA-N 0.000 claims 1
LFOZTNGKMPEUKX-UHFFFAOYSA-N [2,6-difluoro-4-[2-[4-(morpholin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CCOCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 LFOZTNGKMPEUKX-UHFFFAOYSA-N 0.000 claims 1
OMGTUGCOTREROQ-UHFFFAOYSA-N [2,6-difluoro-4-[2-[4-(piperazin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CCNCC5)=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 OMGTUGCOTREROQ-UHFFFAOYSA-N 0.000 claims 1
LMQHYVFVTTVLFA-UHFFFAOYSA-N [2,6-difluoro-4-[2-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 LMQHYVFVTTVLFA-UHFFFAOYSA-N 0.000 claims 1
VONOJJRWBCYRBU-UHFFFAOYSA-N [2,6-difluoro-4-[2-[4-[(4-methylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 VONOJJRWBCYRBU-UHFFFAOYSA-N 0.000 claims 1
NNJGRDWZESOGRG-UHFFFAOYSA-N [2,6-difluoro-4-[2-[[1-(2-methoxyethyl)pyrazol-4-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NN(CCOC)C=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 NNJGRDWZESOGRG-UHFFFAOYSA-N 0.000 claims 1
ADJPSOQGNGJLLG-UHFFFAOYSA-N [2,6-difluoro-4-[2-[[2-(4-methylpiperazin-1-yl)pyridin-4-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCN1C1=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 ADJPSOQGNGJLLG-UHFFFAOYSA-N 0.000 claims 1
ZBDKEWDYTXQOOS-UHFFFAOYSA-N [2,6-difluoro-4-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methanol Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CO)=C(F)C=3)C2=N1 ZBDKEWDYTXQOOS-UHFFFAOYSA-N 0.000 claims 1
MDOWGJUNHKZRJV-UHFFFAOYSA-N [2,6-difluoro-4-[2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(CCO)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 MDOWGJUNHKZRJV-UHFFFAOYSA-N 0.000 claims 1
PEYHAJOTROXRCG-UHFFFAOYSA-N [2-chloro-4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(Cl)C(C(=O)N4CCOCC4)=CC=3)C2=N1 PEYHAJOTROXRCG-UHFFFAOYSA-N 0.000 claims 1
NCZCPEOWINAATE-UHFFFAOYSA-N [2-chloro-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)Cl)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 NCZCPEOWINAATE-UHFFFAOYSA-N 0.000 claims 1
WUGAPWHZMVUCOL-UHFFFAOYSA-N [2-fluoro-4-[2-(3-methoxy-4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(C)C(OC)=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=C1 WUGAPWHZMVUCOL-UHFFFAOYSA-N 0.000 claims 1
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ZIHYMFAXHDVVBN-UHFFFAOYSA-N [2-fluoro-4-[2-(4-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C3=NC(NC=4C=CC(F)=CC=4)=NC=C3C=C2)C=C1F ZIHYMFAXHDVVBN-UHFFFAOYSA-N 0.000 claims 1
MHHXJUCHOQSXHL-UHFFFAOYSA-N [2-fluoro-4-[2-(4-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 MHHXJUCHOQSXHL-UHFFFAOYSA-N 0.000 claims 1
FXAMHYMLVWBHRX-UHFFFAOYSA-N [2-fluoro-4-[2-(4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 FXAMHYMLVWBHRX-UHFFFAOYSA-N 0.000 claims 1
APFNTCMXERUWAP-UHFFFAOYSA-N [2-fluoro-4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCN(C)CC4)=CC=3)C2=N1 APFNTCMXERUWAP-UHFFFAOYSA-N 0.000 claims 1
FVRBCUPVTQAIEX-UHFFFAOYSA-N [2-fluoro-4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 FVRBCUPVTQAIEX-UHFFFAOYSA-N 0.000 claims 1
CGCHXCDIDUYGFK-UHFFFAOYSA-N [2-fluoro-4-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=NC=CC=4)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 CGCHXCDIDUYGFK-UHFFFAOYSA-N 0.000 claims 1
OPQBVLLPSXVZFX-UHFFFAOYSA-N [2-fluoro-4-[2-[(1-methylpyrazol-4-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 OPQBVLLPSXVZFX-UHFFFAOYSA-N 0.000 claims 1
DITZTVVXQONVDK-UHFFFAOYSA-N [2-fluoro-4-[2-[(6-methoxypyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 DITZTVVXQONVDK-UHFFFAOYSA-N 0.000 claims 1
WRRDXITWGDQDCF-UHFFFAOYSA-N [2-fluoro-4-[2-[(6-propan-2-yloxypyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 WRRDXITWGDQDCF-UHFFFAOYSA-N 0.000 claims 1
JLXOHDYRJKURSD-UHFFFAOYSA-N [2-fluoro-4-[2-[4-(morpholin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CCOCC5)=CC=4)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 JLXOHDYRJKURSD-UHFFFAOYSA-N 0.000 claims 1
RPVPWTNHPOQWHO-UHFFFAOYSA-N [2-fluoro-4-[2-[4-(piperazin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CCNCC5)=CC=4)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 RPVPWTNHPOQWHO-UHFFFAOYSA-N 0.000 claims 1
ANVUKCURMGOHHQ-UHFFFAOYSA-N [2-fluoro-4-[2-[4-(piperidin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CC5CCNCC5)=CC=4)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 ANVUKCURMGOHHQ-UHFFFAOYSA-N 0.000 claims 1
VXHPPQCIQHURFZ-UHFFFAOYSA-N [2-fluoro-4-[2-[4-methyl-3-(morpholin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(CN2CCOCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC=C1C(=O)N1CCOCC1 VXHPPQCIQHURFZ-UHFFFAOYSA-N 0.000 claims 1
MKJMFJDLMOELMH-UHFFFAOYSA-N [2-fluoro-4-[2-[4-methyl-3-(piperazin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(CN2CCNCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC=C1C(=O)N1CCOCC1 MKJMFJDLMOELMH-UHFFFAOYSA-N 0.000 claims 1
QWFKHVZRNPAVAV-UHFFFAOYSA-N [2-fluoro-4-[2-[4-methyl-3-[(4-methylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=CC=C1C QWFKHVZRNPAVAV-UHFFFAOYSA-N 0.000 claims 1
YFIYJPUMHYTBMT-UHFFFAOYSA-N [2-fluoro-4-[2-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)C(F)(F)F)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 YFIYJPUMHYTBMT-UHFFFAOYSA-N 0.000 claims 1
CLKLNUZYFYSTKW-UHFFFAOYSA-N [2-fluoro-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)F)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 CLKLNUZYFYSTKW-UHFFFAOYSA-N 0.000 claims 1
GWUBCFGWDIYTJN-UHFFFAOYSA-N [2-fluoro-4-[[7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)F)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=CC=3)C2=N1 GWUBCFGWDIYTJN-UHFFFAOYSA-N 0.000 claims 1
PPZDWOFKOYVYFZ-UHFFFAOYSA-N [2-fluoro-5-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=CC=C1F PPZDWOFKOYVYFZ-UHFFFAOYSA-N 0.000 claims 1
XEDQQFPTGUWZBI-UHFFFAOYSA-N [2-fluoro-5-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C(C(F)=CC=3)C(=O)N3CCOCC3)=NC=C2C=C1 XEDQQFPTGUWZBI-UHFFFAOYSA-N 0.000 claims 1
RPFLBUAIDGANCA-UHFFFAOYSA-N [2-methyl-4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(C)C(C(=O)N4CCOCC4)=CC=3)C2=N1 RPFLBUAIDGANCA-UHFFFAOYSA-N 0.000 claims 1
QQBUTSCGZBGCDL-UHFFFAOYSA-N [2-methyl-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 QQBUTSCGZBGCDL-UHFFFAOYSA-N 0.000 claims 1
TZJCBNOFHNXOMP-UHFFFAOYSA-N [2-methyl-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(C(=O)N2CCOCC2)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 TZJCBNOFHNXOMP-UHFFFAOYSA-N 0.000 claims 1
RIILYBUIWSCXRW-UHFFFAOYSA-N [2-methyl-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(C(=O)N2CCCC2)C(C)=CC=1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 RIILYBUIWSCXRW-UHFFFAOYSA-N 0.000 claims 1
KWOYDEDJJFXUDF-UHFFFAOYSA-N [3-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C(C=CC=3)C(=O)N3CCOCC3)=NC=C2C=C1 KWOYDEDJJFXUDF-UHFFFAOYSA-N 0.000 claims 1
RYXLXKGNPKSRQJ-UHFFFAOYSA-N [3-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 RYXLXKGNPKSRQJ-UHFFFAOYSA-N 0.000 claims 1
OMGLWSAGXRUXLB-BGYRXZFFSA-N [3-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=CC=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 OMGLWSAGXRUXLB-BGYRXZFFSA-N 0.000 claims 1
FPEUCCCVKWGUQU-UHFFFAOYSA-N [3-fluoro-4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C(=CC(=CC=3)C(=O)N3CCOCC3)F)C2=N1 FPEUCCCVKWGUQU-UHFFFAOYSA-N 0.000 claims 1
UCLHWOAMQYFXRH-UHFFFAOYSA-N [4-(2-anilinopyrrolo[2,3-d]pyrimidin-7-yl)-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC=CC=4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 UCLHWOAMQYFXRH-UHFFFAOYSA-N 0.000 claims 1
UFSQFCQRNVIZJE-UHFFFAOYSA-N [4-(dimethylamino)piperidin-1-yl]-[4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]methanone Chemical compound C1CC(N(C)C)CCN1C(=O)C1=CC=C(N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2)C=C1F UFSQFCQRNVIZJE-UHFFFAOYSA-N 0.000 claims 1
GJTMTPLTWXKRFF-UHFFFAOYSA-N [4-(dimethylamino)piperidin-1-yl]-[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methanone Chemical compound C1CC(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 GJTMTPLTWXKRFF-UHFFFAOYSA-N 0.000 claims 1
XMHDVYCZWCTXIY-UHFFFAOYSA-N [4-[2-(3,4-diethoxyanilino)-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C=C(C)N2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 XMHDVYCZWCTXIY-UHFFFAOYSA-N 0.000 claims 1
XSNDMYYCPMMHKM-UHFFFAOYSA-N [4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2)C=C1F XSNDMYYCPMMHKM-UHFFFAOYSA-N 0.000 claims 1
GTOAXSOYWSKVCR-UHFFFAOYSA-N [4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 GTOAXSOYWSKVCR-UHFFFAOYSA-N 0.000 claims 1
IROJYWVYFDFIFG-UHFFFAOYSA-N [4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylphenyl]-morpholin-4-ylmethanone Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(C)C(C(=O)N4CCOCC4)=CC=3)C2=N1 IROJYWVYFDFIFG-UHFFFAOYSA-N 0.000 claims 1
AUOSZJQBGKSZDC-UHFFFAOYSA-N [4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C3=NC(NC=4C=C(C)C(C)=CC=4)=NC=C3C=C2)C=C1 AUOSZJQBGKSZDC-UHFFFAOYSA-N 0.000 claims 1
RWOQEFYCIOGVOB-UHFFFAOYSA-N [4-[2-(3,4-dimethylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 RWOQEFYCIOGVOB-UHFFFAOYSA-N 0.000 claims 1
RHOAHAZEPUGQEZ-UHFFFAOYSA-N [4-[2-(3-chloro-4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 RHOAHAZEPUGQEZ-UHFFFAOYSA-N 0.000 claims 1
ANMFZZSXFLTBLW-UHFFFAOYSA-N [4-[2-(3-fluoro-4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(F)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 ANMFZZSXFLTBLW-UHFFFAOYSA-N 0.000 claims 1
YWEPNYCEBRFWCQ-UHFFFAOYSA-N [4-[2-(3-methoxy-4-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C(C)C(OC)=CC(NC=2N=C3N(C=4C=CC(=CC=4)C(=O)N4CCOCC4)C=CC3=CN=2)=C1 YWEPNYCEBRFWCQ-UHFFFAOYSA-N 0.000 claims 1
VOMIDVLZIHIBFL-UHFFFAOYSA-N [4-[2-(4-chloro-3-methoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(Cl)C(OC)=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=C1 VOMIDVLZIHIBFL-UHFFFAOYSA-N 0.000 claims 1
FXPAWFCTGXYONJ-UHFFFAOYSA-N [4-[2-(4-fluoro-3-methoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylphenyl]-morpholin-4-ylmethanone Chemical compound C1=C(F)C(OC)=CC(NC=2N=C3N(C=4C=C(C)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=C1 FXPAWFCTGXYONJ-UHFFFAOYSA-N 0.000 claims 1
NFBRFIACFHEGGX-UHFFFAOYSA-N [4-[2-(4-fluoro-3-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methylphenyl]-morpholin-4-ylmethanone Chemical compound C1=C(F)C(C)=CC(NC=2N=C3N(C=4C=C(C)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=C1 NFBRFIACFHEGGX-UHFFFAOYSA-N 0.000 claims 1
DAASOYVUUDIISL-UHFFFAOYSA-N [4-[2-(4-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(N2C3=NC(NC=4C=CC(F)=CC=4)=NC=C3C=C2)C=C1 DAASOYVUUDIISL-UHFFFAOYSA-N 0.000 claims 1
SLDHUSCXMUWFQF-UHFFFAOYSA-N [4-[2-(4-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 SLDHUSCXMUWFQF-UHFFFAOYSA-N 0.000 claims 1
BHJKRUNVZVLIIT-UHFFFAOYSA-N [4-[2-(4-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCCC3)C2=N1 BHJKRUNVZVLIIT-UHFFFAOYSA-N 0.000 claims 1
IBXTVWNJCHMDJS-UHFFFAOYSA-N [4-[2-[(1,5-dimethylpyrazol-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound CN1C(C)=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=N1 IBXTVWNJCHMDJS-UHFFFAOYSA-N 0.000 claims 1
QCVAEPGPMIMZOL-UHFFFAOYSA-N [4-[2-[(1-methylpyrazol-4-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 QCVAEPGPMIMZOL-UHFFFAOYSA-N 0.000 claims 1
LTHNQPDRALFTCL-UHFFFAOYSA-N [4-[2-[(5,6-dimethylpyridin-2-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound N1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 LTHNQPDRALFTCL-UHFFFAOYSA-N 0.000 claims 1
MILCPSHJDITXMG-UHFFFAOYSA-N [4-[2-[(6-methoxypyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 MILCPSHJDITXMG-UHFFFAOYSA-N 0.000 claims 1
CNYAORXUZPKJCW-UHFFFAOYSA-N [4-[2-[(6-methylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 CNYAORXUZPKJCW-UHFFFAOYSA-N 0.000 claims 1
UPBHGHGSWSVDPH-UHFFFAOYSA-N [4-[2-[3-(2,5-dioxa-8-azaspiro[3.5]nonan-8-ylmethyl)-4-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(CN2CC3(COC3)OCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC=C1C(=O)N1CCOCC1 UPBHGHGSWSVDPH-UHFFFAOYSA-N 0.000 claims 1
WUOLMMMWWSPEGO-UHFFFAOYSA-N [4-[2-[3-(4,7-diazaspiro[2.5]octan-7-ylmethyl)-4-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(CN2CC3(CC3)NCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC=C1C(=O)N1CCOCC1 WUOLMMMWWSPEGO-UHFFFAOYSA-N 0.000 claims 1
XVNOFIZGMGYUSC-UHFFFAOYSA-N [4-[2-[3-[(3,3-dimethylpiperazin-1-yl)methyl]-4-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(CN2CC(C)(C)NCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC=C1C(=O)N1CCOCC1 XVNOFIZGMGYUSC-UHFFFAOYSA-N 0.000 claims 1
QSABEPGVEAUCGY-UHFFFAOYSA-N [4-[2-[3-[(4-cyclopropylpiperazin-1-yl)methyl]-4-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1=C(CN2CCN(CC2)C2CC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC=C1C(=O)N1CCOCC1 QSABEPGVEAUCGY-UHFFFAOYSA-N 0.000 claims 1
AXJXFZMZSBWCDL-FCHUYYIVSA-N [4-[2-[3-[[(2r,5s)-2,5-dimethylpiperazin-1-yl]methyl]-4-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C[C@@H]1CN[C@@H](C)CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=CC=C1C AXJXFZMZSBWCDL-FCHUYYIVSA-N 0.000 claims 1
SNBPHFRMMXVZCX-SZPZYZBQSA-N [4-[2-[3-[[(3s,5r)-3,5-dimethylpiperazin-1-yl]methyl]-4-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(C(=O)N5CCOCC5)=CC=4)C=CC3=CN=2)=CC=C1C SNBPHFRMMXVZCX-SZPZYZBQSA-N 0.000 claims 1
SQEXVBGJSFDXHL-UHFFFAOYSA-N [4-[2-[4-(4-ethylpiperazin-1-yl)-3-methylanilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1CN(CC)CCN1C(C(=C1)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 SQEXVBGJSFDXHL-UHFFFAOYSA-N 0.000 claims 1
FIQYJHUMAHFSHP-UHFFFAOYSA-N [4-[2-[4-(methoxymethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(COC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 FIQYJHUMAHFSHP-UHFFFAOYSA-N 0.000 claims 1
KUQYZJIAWFVELJ-UHFFFAOYSA-N [4-[2-[4-[(4-cyclopropylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CCN(CC5)C5CC5)=CC=4)=NC=C3C=C2)=CC=C1C(=O)N1CCOCC1 KUQYZJIAWFVELJ-UHFFFAOYSA-N 0.000 claims 1
XDETUWKIRDPWAQ-UHFFFAOYSA-N [4-[2-[4-[(4-ethylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCN(C)CC4)=C(F)C=3)C2=N1 XDETUWKIRDPWAQ-UHFFFAOYSA-N 0.000 claims 1
JGKJMFMVGBWUHM-UXHICEINSA-N [4-[2-[4-[[(2s,5r)-2,5-dimethylpiperazin-1-yl]methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound C[C@H]1CN[C@H](C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 JGKJMFMVGBWUHM-UXHICEINSA-N 0.000 claims 1
JBFULUGVWFFCDG-BGYRXZFFSA-N [4-[2-[4-[[(3s,5r)-3,5-dimethylpiperazin-1-yl]methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 JBFULUGVWFFCDG-BGYRXZFFSA-N 0.000 claims 1
YXNDURRZDOYBPF-UHFFFAOYSA-N [4-[2-[4-methyl-3-[(4-methylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=CC(=CC=4)C(=O)N4CCOCC4)C=CC3=CN=2)=CC=C1C YXNDURRZDOYBPF-UHFFFAOYSA-N 0.000 claims 1
MJJKIUXKJYSTBO-UHFFFAOYSA-N [4-[2-[[2-(4,7-diazaspiro[2.5]octan-7-yl)pyridin-4-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=C(N=CC=4)N4CC5(CC5)NCC4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 MJJKIUXKJYSTBO-UHFFFAOYSA-N 0.000 claims 1
VCNAFDWRYNHCCL-UHFFFAOYSA-N [4-[2-[[6-(4,7-diazaspiro[2.5]octan-7-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)N4CC5(CC5)NCC4)=NC=C3C=C2)=CC(F)=C1C(=O)N1CCOCC1 VCNAFDWRYNHCCL-UHFFFAOYSA-N 0.000 claims 1
HPIYLJABDVKPQO-ZWKOTPCHSA-N [4-[2-[[6-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound C[C@@H]1CN[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 HPIYLJABDVKPQO-ZWKOTPCHSA-N 0.000 claims 1
UGMIVSNVOXKZFG-HDICACEKSA-N [4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2,6-difluorophenyl]-morpholin-4-ylmethanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=C(F)C=3)C2=N1 UGMIVSNVOXKZFG-HDICACEKSA-N 0.000 claims 1
FUNLWWPEAAWMGH-KDURUIRLSA-N [4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-fluorophenyl]-morpholin-4-ylmethanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)C2=N1 FUNLWWPEAAWMGH-KDURUIRLSA-N 0.000 claims 1
BWEHADIIUWPENR-UHFFFAOYSA-N [4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C(=O)N3CCOCC3)=NC=C2C=C1 BWEHADIIUWPENR-UHFFFAOYSA-N 0.000 claims 1
DAVLLMWAQKBQNR-UHFFFAOYSA-N [4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-piperazin-1-ylmethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C(=O)N3CCNCC3)=NC=C2C=C1 DAVLLMWAQKBQNR-UHFFFAOYSA-N 0.000 claims 1
YWMHOJKAAGYIFX-UHFFFAOYSA-N [4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-(trifluoromethyl)phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)C(F)(F)F)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 YWMHOJKAAGYIFX-UHFFFAOYSA-N 0.000 claims 1
NIFLALWLTCQRKC-UHFFFAOYSA-N [4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 NIFLALWLTCQRKC-UHFFFAOYSA-N 0.000 claims 1
VCVBRHXFSWNQOM-UHFFFAOYSA-N [4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 VCVBRHXFSWNQOM-UHFFFAOYSA-N 0.000 claims 1
DCHCWIZLBHPODM-UHFFFAOYSA-N [4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)C(=O)N4CCOCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 DCHCWIZLBHPODM-UHFFFAOYSA-N 0.000 claims 1
OALNVEKANNITLW-UHFFFAOYSA-N [4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-(2,5-dioxa-8-azaspiro[3.5]nonan-8-yl)methanone Chemical compound FC1=CC(N2C3=NC(NC=4C=C(N=CC=4)C(=O)N4CC5(COC5)OCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 OALNVEKANNITLW-UHFFFAOYSA-N 0.000 claims 1
OFJKFEOLLNLGOB-KDURUIRLSA-N [4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=N1 OFJKFEOLLNLGOB-KDURUIRLSA-N 0.000 claims 1
YEYLHQGAFUGMDQ-UHFFFAOYSA-N [4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-piperazin-1-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=C(N=CC=4)C(=O)N4CCNCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 YEYLHQGAFUGMDQ-UHFFFAOYSA-N 0.000 claims 1
GJISMAUIZQRION-UHFFFAOYSA-N [4-[[7-[3,5-difluoro-4-(pyrrolidin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)C(=O)N4CCOCC4)=NC=C3C=C2)=CC(F)=C1CN1CCCC1 GJISMAUIZQRION-UHFFFAOYSA-N 0.000 claims 1
CEDCLFVNUJBIAM-UHFFFAOYSA-N [4-[[7-[3-chloro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound ClC1=CC(N2C3=NC(NC=4C=CC(=CC=4)C(=O)N4CCOCC4)=NC=C3C=C2)=CC=C1CN1CCOCC1 CEDCLFVNUJBIAM-UHFFFAOYSA-N 0.000 claims 1
XJZMGWAUXVVHGE-UHFFFAOYSA-N [4-[[7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(=CC=4)C(=O)N4CCOCC4)=NC=C3C=C2)=CC=C1CN1CCOCC1 XJZMGWAUXVVHGE-UHFFFAOYSA-N 0.000 claims 1
KXWCGAAUJGHFRO-UHFFFAOYSA-N [5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C KXWCGAAUJGHFRO-UHFFFAOYSA-N 0.000 claims 1
HNPHKKRFEUGWGA-OYRHEFFESA-N [5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]-2-methylphenyl]-[(3r,5s)-3,5-dimethylpiperazin-1-yl]methanone Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1C HNPHKKRFEUGWGA-OYRHEFFESA-N 0.000 claims 1
TYOJNKGYUTWARB-UHFFFAOYSA-N [5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 TYOJNKGYUTWARB-UHFFFAOYSA-N 0.000 claims 1
QMUKXWVWYVJMAQ-UHFFFAOYSA-N [5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-2-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)C(=O)N4CCOCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 QMUKXWVWYVJMAQ-UHFFFAOYSA-N 0.000 claims 1
HCXMGPZHXMPWDR-UHFFFAOYSA-N [5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound FC1=CC(N2C3=NC(NC=4C=C(C=NC=4)C(=O)N4CCOCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 HCXMGPZHXMPWDR-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
125000002619 bicyclic group Chemical group 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 1
125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
SLVDOUWFWWGHDM-UHFFFAOYSA-N cyclopropyl-[4-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methanol Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(O)C3CC3)C2=N1 SLVDOUWFWWGHDM-UHFFFAOYSA-N 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
125000002950 monocyclic group Chemical group 0.000 claims 1
ONESHIXOKOYSHV-UHFFFAOYSA-N morpholin-4-yl-[1-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]cyclopropyl]methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C3(CC3)C(=O)N3CCOCC3)C2=N1 ONESHIXOKOYSHV-UHFFFAOYSA-N 0.000 claims 1
GGDMRDFPARYZRK-UHFFFAOYSA-N morpholin-4-yl-[4-[2-(4-propan-2-yloxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 GGDMRDFPARYZRK-UHFFFAOYSA-N 0.000 claims 1
XEHHSUMCBBKMDR-UHFFFAOYSA-N morpholin-4-yl-[4-[2-[(6-propan-2-yloxypyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methanone Chemical compound C1=NC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 XEHHSUMCBBKMDR-UHFFFAOYSA-N 0.000 claims 1
OYOSAVYVCYCKJB-UHFFFAOYSA-N morpholin-4-yl-[4-[2-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)N3CCOCC3)C2=N1 OYOSAVYVCYCKJB-UHFFFAOYSA-N 0.000 claims 1
LVVXMCMOPYUNQY-UHFFFAOYSA-N n,n-diethyl-4-[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)N(CC)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 LVVXMCMOPYUNQY-UHFFFAOYSA-N 0.000 claims 1
AOTSXNUBXLSNLQ-UHFFFAOYSA-N n,n-dimethyl-4-[2-(3,4,5-trimethoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(=O)(=O)N(C)C)C=CC3=CN=2)=C1 AOTSXNUBXLSNLQ-UHFFFAOYSA-N 0.000 claims 1
DOAZAENSDGVSFD-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C4OCOC4=CC=3)=NC=C2C=C1 DOAZAENSDGVSFD-UHFFFAOYSA-N 0.000 claims 1
IMSXVXRDJYOWTL-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 IMSXVXRDJYOWTL-UHFFFAOYSA-N 0.000 claims 1
JSJBBCXMGVSXNX-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(=CC=3)C(=O)NCCO)=NC=C2C=C1 JSJBBCXMGVSXNX-UHFFFAOYSA-N 0.000 claims 1
UNQLFAWJQTWSDS-UHFFFAOYSA-N n-(3,4-diethoxyphenyl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 UNQLFAWJQTWSDS-UHFFFAOYSA-N 0.000 claims 1
QRBDIEDVGRHYTD-UHFFFAOYSA-N n-(3,4-diethoxyphenyl)-7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-6-methylpyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C=C(C)N2C=3C=C(F)C(CN4CCOCC4)=CC=3)C2=N1 QRBDIEDVGRHYTD-UHFFFAOYSA-N 0.000 claims 1
FNPBOUPEEKWXFE-UHFFFAOYSA-N n-(3,4-diethoxyphenyl)-7-[4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CN4CCOCC4)=CC=3)C2=N1 FNPBOUPEEKWXFE-UHFFFAOYSA-N 0.000 claims 1
DRENPQMNPZPRJY-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 DRENPQMNPZPRJY-UHFFFAOYSA-N 0.000 claims 1
LXTNXXVQLLCNNR-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-6-methylpyrrolo[2,3-d]pyrimidin-2-amine Chemical class N1=C2N(C=3C=C(F)C(CN4CCOCC4)=CC=3)C(C)=CC2=CN=C1NC1=CC=C(C)C(C)=C1 LXTNXXVQLLCNNR-UHFFFAOYSA-N 0.000 claims 1
ZVCQEFJJGQFYRH-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-[4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CN4CCOCC4)=CC=3)C2=N1 ZVCQEFJJGQFYRH-UHFFFAOYSA-N 0.000 claims 1
OVQAISUHHXMOFJ-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=CC(OC)=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 OVQAISUHHXMOFJ-UHFFFAOYSA-N 0.000 claims 1
HZUSKOXZHXMIPZ-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1=C(Cl)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 HZUSKOXZHXMIPZ-UHFFFAOYSA-N 0.000 claims 1
BTSZBIBTHKCOPM-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=CC=3)C2=N1 BTSZBIBTHKCOPM-UHFFFAOYSA-N 0.000 claims 1
QYOJQYFWBXMQQQ-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-7-[4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CN4CCOCC4)=CC=3)C2=N1 QYOJQYFWBXMQQQ-UHFFFAOYSA-N 0.000 claims 1
WBDPZYYFUVYXCJ-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-7-[4-[(4-ethylpiperazin-1-yl)methyl]-3,5-difluorophenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC1=C(F)C=C(N2C3=NC(NC=4C=C(Cl)C(C)=CC=4)=NC=C3C=C2)C=C1F WBDPZYYFUVYXCJ-UHFFFAOYSA-N 0.000 claims 1
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ZOPQXHFAJYJGOO-UHFFFAOYSA-N n-(4-fluoro-3-methoxyphenyl)-7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-6-methylpyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(F)C(OC)=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=CC=4)C(C)=CC3=CN=2)=C1 ZOPQXHFAJYJGOO-UHFFFAOYSA-N 0.000 claims 1
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ISBZHMFHBXRKHS-UHFFFAOYSA-N n-(4-fluoro-3-methylphenyl)-7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(F)C(C)=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=CC=4)C=CC3=CN=2)=C1 ISBZHMFHBXRKHS-UHFFFAOYSA-N 0.000 claims 1
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VWGFSTWLZLPRNH-UHFFFAOYSA-N n-(4-fluorophenyl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(F)=CC=3)=NC=C2C=C1 VWGFSTWLZLPRNH-UHFFFAOYSA-N 0.000 claims 1
YWOWHRRREZDNOA-UHFFFAOYSA-N n-(4-methoxyphenyl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 YWOWHRRREZDNOA-UHFFFAOYSA-N 0.000 claims 1
NPEMROGMFPULOA-UHFFFAOYSA-N n-(4-methylphenyl)-7-[4-(methylsulfinylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CS(C)=O)=CC=3)C2=N1 NPEMROGMFPULOA-UHFFFAOYSA-N 0.000 claims 1
ZPYJPBCODMAWBY-UHFFFAOYSA-N n-(4-methylphenyl)-7-[4-(methylsulfonylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CS(C)(=O)=O)=CC=3)C2=N1 ZPYJPBCODMAWBY-UHFFFAOYSA-N 0.000 claims 1
KHGWOFSFLFBODL-UHFFFAOYSA-N n-(4-methylphenyl)-7-[4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CN4CCOCC4)=CC=3)C2=N1 KHGWOFSFLFBODL-UHFFFAOYSA-N 0.000 claims 1
FXLKNVOOCCFEPH-UHFFFAOYSA-N n-(4-propan-2-yloxyphenyl)-7-[4-(pyrrolidin-1-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(CN4CCCC4)=CC=3)C2=N1 FXLKNVOOCCFEPH-UHFFFAOYSA-N 0.000 claims 1
FXFTVYGDADXXGX-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 FXFTVYGDADXXGX-UHFFFAOYSA-N 0.000 claims 1
OBFWNUQVBBOEQW-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 OBFWNUQVBBOEQW-UHFFFAOYSA-N 0.000 claims 1
BIJCXLLNGBISCO-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-2-fluoro-5-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=CC=C1F BIJCXLLNGBISCO-UHFFFAOYSA-N 0.000 claims 1
PNANRTZXALECJC-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-4-[2-(4-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]benzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=C(N2C3=NC(NC=4C=CC(F)=CC=4)=NC=C3C=C2)C=C1 PNANRTZXALECJC-UHFFFAOYSA-N 0.000 claims 1
PSPBSXHLTRURJN-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzamide Chemical compound CCN1CCCC1CNC(=O)C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 PSPBSXHLTRURJN-UHFFFAOYSA-N 0.000 claims 1
XWYDCNFOMKZOMZ-UHFFFAOYSA-N n-[2-(4,7-diazaspiro[2.5]octan-7-yl)pyridin-4-yl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C(N=CC=3)N3CC4(CC4)NCC3)=NC=C2C=C1 XWYDCNFOMKZOMZ-UHFFFAOYSA-N 0.000 claims 1
LYYHAKJPPRRGOZ-UHFFFAOYSA-N n-[2-(4-cyclopropylpiperazin-1-yl)pyridin-4-yl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(N=CC=4)N4CCN(CC4)C4CC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 LYYHAKJPPRRGOZ-UHFFFAOYSA-N 0.000 claims 1
PBZFSPCXUFTFNW-UHFFFAOYSA-N n-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1CN(C)CCN1C(N=C1)=NC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 PBZFSPCXUFTFNW-UHFFFAOYSA-N 0.000 claims 1
MXUCDRQSXZCHQD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(CCN(C)C)C(=O)C(C=1)=CC=CC=1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 MXUCDRQSXZCHQD-UHFFFAOYSA-N 0.000 claims 1
JKKXMEJRMUKIPX-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 JKKXMEJRMUKIPX-UHFFFAOYSA-N 0.000 claims 1
NAJBSABAXHIEJR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 NAJBSABAXHIEJR-UHFFFAOYSA-N 0.000 claims 1
MMMAQSLHNPUPFK-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-n-methyl-4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)N(C)CCN(C)C)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 MMMAQSLHNPUPFK-UHFFFAOYSA-N 0.000 claims 1
YIFIXQIIBFRIFS-UHFFFAOYSA-N n-[2-[(4-cyclopropylpiperazin-1-yl)methyl]pyridin-4-yl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(CN5CCN(CC5)C5CC5)N=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 YIFIXQIIBFRIFS-UHFFFAOYSA-N 0.000 claims 1
KGIJVUOZLVKWEJ-UHFFFAOYSA-N n-[3-(4,7-diazaspiro[2.5]octan-7-ylmethyl)-4-methylphenyl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CC3(CC3)NCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 KGIJVUOZLVKWEJ-UHFFFAOYSA-N 0.000 claims 1
GXQMHHWVTILWFM-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 GXQMHHWVTILWFM-UHFFFAOYSA-N 0.000 claims 1
OVJPBMFOTFWECC-UHFFFAOYSA-N n-[3-(7-azabicyclo[2.2.1]heptan-7-ylmethyl)-4-methylphenyl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2C3CCC2CC3)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 OVJPBMFOTFWECC-UHFFFAOYSA-N 0.000 claims 1
RMHAQRYQHCXEFU-UHFFFAOYSA-N n-[3-(azetidin-3-yloxymethyl)-4-methylphenyl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(COC2CNC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 RMHAQRYQHCXEFU-UHFFFAOYSA-N 0.000 claims 1
HQEAPQJFRRFMSH-UHFFFAOYSA-N n-[3-(imidazol-1-ylmethyl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C(CN4C=NC=C4)C=CC=3)=NC=C2C=C1 HQEAPQJFRRFMSH-UHFFFAOYSA-N 0.000 claims 1
ACDIVKBIAVUUSV-UHFFFAOYSA-N n-[3-[(4-cyclopropylpiperazin-1-yl)methyl]-4-methylphenyl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CCN(CC2)C2CC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C(C=C1F)=CC(F)=C1CN1CCOCC1 ACDIVKBIAVUUSV-UHFFFAOYSA-N 0.000 claims 1
LUIYXCAYRKWWIC-UHFFFAOYSA-N n-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CCOC1=CC=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 LUIYXCAYRKWWIC-UHFFFAOYSA-N 0.000 claims 1
QSTRMTAHJHDDCX-UHFFFAOYSA-N n-[3-[2-(diethylamino)ethoxy]phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound CCN(CC)CCOC1=CC=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(C)(=O)=O)C=CC3=CN=2)=C1 QSTRMTAHJHDDCX-UHFFFAOYSA-N 0.000 claims 1
KZCHIOPNEUKSNE-UHFFFAOYSA-N n-[3-[2-(dimethylamino)ethoxy]-4-methoxyphenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(OCCN(C)C)C(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 KZCHIOPNEUKSNE-UHFFFAOYSA-N 0.000 claims 1
TYMNKUYTGMPJEM-UHFFFAOYSA-N n-[3-[3-(dimethylamino)propoxy]-4-methoxyphenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(OCCCN(C)C)C(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 TYMNKUYTGMPJEM-UHFFFAOYSA-N 0.000 claims 1
FUFPZLNTZSAPRA-UHFFFAOYSA-N n-[4-(1-methylpiperidin-4-yl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 FUFPZLNTZSAPRA-UHFFFAOYSA-N 0.000 claims 1
FXHDITNEAFNTTL-UHFFFAOYSA-N n-[4-(4-ethylpiperazin-1-yl)-3-methylphenyl]-7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(CC)CCN1C(C(=C1)C)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=CC=3)C2=N1 FXHDITNEAFNTTL-UHFFFAOYSA-N 0.000 claims 1
VIISTRLGJBDKQI-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 VIISTRLGJBDKQI-UHFFFAOYSA-N 0.000 claims 1
KQVUYWKXIFLZIW-UHFFFAOYSA-N n-[4-(imidazol-1-ylmethyl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=CC(CN4C=NC=C4)=CC=3)=NC=C2C=C1 KQVUYWKXIFLZIW-UHFFFAOYSA-N 0.000 claims 1
KFXXDWPDGRXACR-UHFFFAOYSA-N n-[4-(methoxymethyl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(COC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 KFXXDWPDGRXACR-UHFFFAOYSA-N 0.000 claims 1
KVAZZESOYJZUOY-UHFFFAOYSA-N n-[4-[(4-cyclopropylpiperazin-1-yl)methyl]phenyl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=CC(CN5CCN(CC5)C5CC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 KVAZZESOYJZUOY-UHFFFAOYSA-N 0.000 claims 1
IQUOUCYYNJTKNQ-UHFFFAOYSA-N n-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 IQUOUCYYNJTKNQ-UHFFFAOYSA-N 0.000 claims 1
LIHXTXJPSSSWML-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 LIHXTXJPSSSWML-UHFFFAOYSA-N 0.000 claims 1
XUYPKMOWFOVALK-CALCHBBNSA-N n-[4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methanesulfonamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(NS(C)(=O)=O)=CC=3)C2=N1 XUYPKMOWFOVALK-CALCHBBNSA-N 0.000 claims 1
FOPCGFPSDLJTRG-KDURUIRLSA-N n-[4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1N1C2=NC(NC=3C=NC(=CC=3)N3C[C@@H](C)N[C@@H](C)C3)=NC=C2C=C1 FOPCGFPSDLJTRG-KDURUIRLSA-N 0.000 claims 1
GVNIOWZPPSQPNV-UHFFFAOYSA-N n-[4-chloro-3-(piperazin-1-ylmethyl)phenyl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=C(CN5CCNCC5)C(Cl)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 GVNIOWZPPSQPNV-UHFFFAOYSA-N 0.000 claims 1
WYYYWHCSUDLIRQ-UHFFFAOYSA-N n-[4-chloro-3-[(4-methylpiperazin-1-yl)methyl]phenyl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=CC=C1Cl WYYYWHCSUDLIRQ-UHFFFAOYSA-N 0.000 claims 1
URAOBJZGHOKJOZ-UHFFFAOYSA-N n-[4-fluoro-3-(trifluoromethyl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=C(C(F)=CC=3)C(F)(F)F)=NC=C2C=C1 URAOBJZGHOKJOZ-UHFFFAOYSA-N 0.000 claims 1
NZCCUUPLBSDSJU-UHFFFAOYSA-N n-[4-methoxy-3-(2-morpholin-4-ylethoxy)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1=C(OCCN2CCOCC2)C(OC)=CC=C1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 NZCCUUPLBSDSJU-UHFFFAOYSA-N 0.000 claims 1
ARRCVACPRCWSEN-UHFFFAOYSA-N n-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1=C(N2CCN(C)CC2)C(OC)=CC=C1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 ARRCVACPRCWSEN-UHFFFAOYSA-N 0.000 claims 1
HAYVMELMISTIHE-UHFFFAOYSA-N n-[4-methyl-3-(morpholin-4-ylmethyl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CCOCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 HAYVMELMISTIHE-UHFFFAOYSA-N 0.000 claims 1
QVVCIBSGTTYRKZ-UHFFFAOYSA-N n-[4-methyl-3-(piperazin-1-ylmethyl)phenyl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=C(CN2CCNCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(C)(=O)=O)C=C1 QVVCIBSGTTYRKZ-UHFFFAOYSA-N 0.000 claims 1
NFRREVWEUHPWJK-UHFFFAOYSA-N n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical class C1CN(CC)CCN1CC(C=N1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 NFRREVWEUHPWJK-UHFFFAOYSA-N 0.000 claims 1
UOEWJHILHLDOSN-HDICACEKSA-N n-[5-chloro-6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C(=C1)Cl)=NC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)C2=N1 UOEWJHILHLDOSN-HDICACEKSA-N 0.000 claims 1
KUWGGZGLEAIIEK-UHFFFAOYSA-N n-[6-(4,7-diazaspiro[2.5]octan-7-yl)pyridin-3-yl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC(NC=3C=NC(=CC=3)N3CC4(CC4)NCC3)=NC=C2C=C1 KUWGGZGLEAIIEK-UHFFFAOYSA-N 0.000 claims 1
FLRCCDFMCBIAOA-UHFFFAOYSA-N n-[6-(4,7-diazaspiro[2.5]octan-7-yl)pyridin-3-yl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)N4CC5(CC5)NCC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 FLRCCDFMCBIAOA-UHFFFAOYSA-N 0.000 claims 1
LIGAGTIKQYQLBP-UHFFFAOYSA-N n-[6-(4-cyclopropylpiperazin-1-yl)pyridin-3-yl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(=CC=4)N4CCN(CC4)C4CC4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 LIGAGTIKQYQLBP-UHFFFAOYSA-N 0.000 claims 1
OHSTZJHPPBKUBD-UHFFFAOYSA-N n-[6-(azetidin-3-yloxy)pyridin-3-yl]-7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound FC1=CC(N2C3=NC(NC=4C=NC(OC5CNC5)=CC=4)=NC=C3C=C2)=CC(F)=C1CN1CCOCC1 OHSTZJHPPBKUBD-UHFFFAOYSA-N 0.000 claims 1
RSTHRRNLQRSIBD-DLBZAZTESA-N n-[6-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyridin-3-yl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C[C@@H]1CN[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 RSTHRRNLQRSIBD-DLBZAZTESA-N 0.000 claims 1
DFVRKGZOFXZNJM-CALCHBBNSA-N n-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]-7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 DFVRKGZOFXZNJM-CALCHBBNSA-N 0.000 claims 1
JRAKMZLXTHXCKU-BGYRXZFFSA-N n-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]-7-[4-(2,5-dioxa-8-azaspiro[3.5]nonan-8-ylmethyl)-3,5-difluorophenyl]pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=C(F)C(CN4CC5(COC5)OCC4)=C(F)C=3)C2=N1 JRAKMZLXTHXCKU-BGYRXZFFSA-N 0.000 claims 1
VCBHIEVPOJEYQB-UHFFFAOYSA-N n-tert-butyl-4-[2-(3,4,5-trimethoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C3N(C=4C=CC(=CC=4)C(=O)NC(C)(C)C)C=CC3=CN=2)=C1 VCBHIEVPOJEYQB-UHFFFAOYSA-N 0.000 claims 1
ONHQYMOWAHKUSR-UHFFFAOYSA-N n-tert-butyl-4-[2-(3,4,5-trimethoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(=O)(=O)NC(C)(C)C)C=CC3=CN=2)=C1 ONHQYMOWAHKUSR-UHFFFAOYSA-N 0.000 claims 1
MJYRJOMSTADWJB-UHFFFAOYSA-N n-tert-butyl-4-[2-(3,4-dimethoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)C(=O)NC(C)(C)C)C2=N1 MJYRJOMSTADWJB-UHFFFAOYSA-N 0.000 claims 1
LTKGHFYBHLPISM-UHFFFAOYSA-N n-tert-butyl-4-[2-(3,4-dimethoxyanilino)pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(=O)(=O)NC(C)(C)C)C2=N1 LTKGHFYBHLPISM-UHFFFAOYSA-N 0.000 claims 1
ROHZVQIJTRJIEG-UHFFFAOYSA-N n-tert-butyl-4-[2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1N1C2=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=NC=C2C=C1 ROHZVQIJTRJIEG-UHFFFAOYSA-N 0.000 claims 1
QACXZZATBXSXEX-UHFFFAOYSA-N n-tert-butyl-4-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(=O)(=O)NC(C)(C)C)C2=N1 QACXZZATBXSXEX-UHFFFAOYSA-N 0.000 claims 1
JHWPWEBTQIWELF-UHFFFAOYSA-N n-tert-butyl-4-[2-[4-[(4-cyclopropylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1N1C2=NC(NC=3C=CC(CN4CCN(CC4)C4CC4)=CC=3)=NC=C2C=C1 JHWPWEBTQIWELF-UHFFFAOYSA-N 0.000 claims 1
YQDLVHBNPFSNEO-OYRHEFFESA-N n-tert-butyl-4-[2-[4-[[(3s,5r)-3,5-dimethylpiperazin-1-yl]methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(=O)(=O)NC(C)(C)C)C2=N1 YQDLVHBNPFSNEO-OYRHEFFESA-N 0.000 claims 1
XCKQNTAKHMEBON-UHFFFAOYSA-N n-tert-butyl-4-[2-[4-methyl-3-(piperazin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1=C(CN2CCNCC2)C(C)=CC=C1NC(N=C12)=NC=C1C=CN2C1=CC=C(S(=O)(=O)NC(C)(C)C)C=C1 XCKQNTAKHMEBON-UHFFFAOYSA-N 0.000 claims 1
YCLIWJAVFHNBJC-UHFFFAOYSA-N n-tert-butyl-4-[2-[4-methyl-3-[(4-methylpiperazin-1-yl)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1CC1=CC(NC=2N=C3N(C=4C=CC(=CC=4)S(=O)(=O)NC(C)(C)C)C=CC3=CN=2)=CC=C1C YCLIWJAVFHNBJC-UHFFFAOYSA-N 0.000 claims 1
QAOWZGLSAIFWAT-RBUKOAKNSA-N n-tert-butyl-4-[2-[[6-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C[C@@H]1CN[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(=O)(=O)NC(C)(C)C)C2=N1 QAOWZGLSAIFWAT-RBUKOAKNSA-N 0.000 claims 1
QVBPGPYTCMBKHA-KDURUIRLSA-N n-tert-butyl-4-[2-[[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(=O)(=O)NC(C)(C)C)C2=N1 QVBPGPYTCMBKHA-KDURUIRLSA-N 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000003226 pyrazolyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
XGXVTOQGJIWLIS-UHFFFAOYSA-N tert-butyl 2-[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 XGXVTOQGJIWLIS-UHFFFAOYSA-N 0.000 claims 1
NZNABMYXPQKMFL-UHFFFAOYSA-N tert-butyl 4-[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]benzoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 NZNABMYXPQKMFL-UHFFFAOYSA-N 0.000 claims 1
UXAAFYYQMVOQGB-UHFFFAOYSA-N tert-butyl 4-[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1N=CC(NC=2N=C3N(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC3=CN=2)=C1 UXAAFYYQMVOQGB-UHFFFAOYSA-N 0.000 claims 1
PXPSPNKPPDPLAZ-UHFFFAOYSA-N tert-butyl 4-[[4-[[7-(4-methylsulfonylphenyl)pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C=CN2C=3C=CC(=CC=3)S(C)(=O)=O)C2=N1 PXPSPNKPPDPLAZ-UHFFFAOYSA-N 0.000 claims 1

JP2010545458A 2008-02-06 2009-02-04 ピロロ［２，３−ｄ］ピリミジンおよびそのチロシンキナーゼ阻害剤としての使用 Expired - Fee Related JP5323095B2 (ja)