KR20140047092A - Jak 억제제로서의 헤테로시클릴 피리미딘 유사체 - Google Patents

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Publication number

KR20140047092A

KR20140047092A KR1020147001951A KR20147001951A KR20140047092A KR 20140047092 A KR20140047092 A KR 20140047092A KR 1020147001951 A KR1020147001951 A KR 1020147001951A KR 20147001951 A KR20147001951 A KR 20147001951A KR 20140047092 A KR20140047092 A KR 20140047092A

Authority

KR

South Korea

Prior art keywords

amino

pyrazol

pyrimidin

chloro

hydroxyethyl

Prior art date

2011-07-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

• Espacenet
• Global Dossier
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• -1 Heterocyclyl pyrimidine analogues Chemical class 0.000 title claims description 70
• 229940122245 Janus kinase inhibitor Drugs 0.000 title abstract description 8
• 229940045688 antineoplastic antimetabolites pyrimidine analogues Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 142
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 62
• 201000010099 disease Diseases 0.000 claims abstract description 36
• 238000011282 treatment Methods 0.000 claims abstract description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• 239000003814 drug Substances 0.000 claims abstract description 16
• 230000001363 autoimmune Effects 0.000 claims abstract description 11
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 11
• 230000002265 prevention Effects 0.000 claims abstract description 11
• 230000000172 allergic effect Effects 0.000 claims abstract description 10
• 208000010668 atopic eczema Diseases 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 88
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 59
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 51
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• 238000000034 method Methods 0.000 claims description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 28
• 208000035475 disorder Diseases 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 19
• 230000000155 isotopic effect Effects 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 206010052779 Transplant rejections Diseases 0.000 claims description 11
• 208000037765 diseases and disorders Diseases 0.000 claims description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
• 208000024908 graft versus host disease Diseases 0.000 claims description 10
• 230000002062 proliferating effect Effects 0.000 claims description 10
• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 9
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• NKEUVIDFOMNIHB-CQSZACIVSA-N 2-[4-[[5-chloro-4-[[(1s)-1-(2-fluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]acetamide Chemical compound C1=NN(CC(=O)N)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=CC=2)F)=N1 NKEUVIDFOMNIHB-CQSZACIVSA-N 0.000 claims description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
• QCIINRKCNBJUQL-OAHLLOKOSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 QCIINRKCNBJUQL-OAHLLOKOSA-N 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• VRCADXNOODMAKS-OAHLLOKOSA-N (2s)-2-(2,5-difluorophenyl)-2-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C(=CC=C(F)C=2)F)=N1 VRCADXNOODMAKS-OAHLLOKOSA-N 0.000 claims description 2
• MJELYOPKYYXACK-OAHLLOKOSA-N (2s)-2-(2,5-difluorophenyl)-2-[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound N1=C(N[C@H](CO)C=2C(=CC=C(F)C=2)F)C(C)=CN=C1NC=1C=NN(C)C=1 MJELYOPKYYXACK-OAHLLOKOSA-N 0.000 claims description 2
• QAEHLBSLFWONBV-OAHLLOKOSA-N (2s)-2-(3,5-difluorophenyl)-2-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)=N1 QAEHLBSLFWONBV-OAHLLOKOSA-N 0.000 claims description 2
• YOOXDLOGFFYUFG-OAHLLOKOSA-N (2s)-2-(3,5-difluorophenyl)-2-[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound N1=C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)C(C)=CN=C1NC=1C=NN(C)C=1 YOOXDLOGFFYUFG-OAHLLOKOSA-N 0.000 claims description 2
• ZGRDJXDWQGTWBF-CQSZACIVSA-N (2s)-2-(3-bromo-5-fluorophenyl)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(Br)C=C(F)C=2)=N1 ZGRDJXDWQGTWBF-CQSZACIVSA-N 0.000 claims description 2
• YUDWGAZWJTYIHS-OAHLLOKOSA-N (2s)-2-(3-bromo-5-fluorophenyl)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(Br)C=C(F)C=2)=N1 YUDWGAZWJTYIHS-OAHLLOKOSA-N 0.000 claims description 2
• JEHPGIJIBVMJLS-OAHLLOKOSA-N (2s)-2-(3-bromo-5-fluorophenyl)-2-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(Br)C=C(F)C=2)=N1 JEHPGIJIBVMJLS-OAHLLOKOSA-N 0.000 claims description 2
• CANMIUFARMZZQH-CQSZACIVSA-N (2s)-2-(3-bromophenyl)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(Br)C=CC=2)=N1 CANMIUFARMZZQH-CQSZACIVSA-N 0.000 claims description 2
• NGIMWXFLGMKNKL-OAHLLOKOSA-N (2s)-2-(3-bromophenyl)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(Br)C=CC=2)=N1 NGIMWXFLGMKNKL-OAHLLOKOSA-N 0.000 claims description 2
• ODUGFSPAXUTPGE-OAHLLOKOSA-N (2s)-2-(3-bromophenyl)-2-[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound N1=C(N[C@H](CO)C=2C=C(Br)C=CC=2)C(C)=CN=C1NC=1C=NN(C)C=1 ODUGFSPAXUTPGE-OAHLLOKOSA-N 0.000 claims description 2
• JJRIDVJZTBQPTI-CQSZACIVSA-N (2s)-2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(N[C@H](CO)C=2C=CC=CC=2)=N1 JJRIDVJZTBQPTI-CQSZACIVSA-N 0.000 claims description 2
• WNQNFVMZAGNSOR-OAHLLOKOSA-N (2s)-2-[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]-2-(2,5-difluorophenyl)ethanol Chemical compound N1=C(N[C@H](CO)C=2C(=CC=C(F)C=2)F)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 WNQNFVMZAGNSOR-OAHLLOKOSA-N 0.000 claims description 2
• WCGNRXHZJZLUQM-OAHLLOKOSA-N (2s)-2-[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]-2-(3,5-difluorophenyl)ethanol Chemical compound N1=C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 WCGNRXHZJZLUQM-OAHLLOKOSA-N 0.000 claims description 2
• ICCWXOGFMYSKGA-MRXNPFEDSA-N (2s)-2-[[2-[[1-(3-aminopropyl)pyrazol-4-yl]amino]-5-chloropyrimidin-4-yl]amino]-2-phenylethanol Chemical compound C1=NN(CCCN)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 ICCWXOGFMYSKGA-MRXNPFEDSA-N 0.000 claims description 2
• GHHPIJVNIUCRLD-CYBMUJFWSA-N (2s)-2-[[5-chloro-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]amino]-2-(2-fluorophenyl)ethanol Chemical compound N([C@H](CO)C=1C(=CC=CC=1)F)C(C(=CN=1)Cl)=NC=1NC=1C=NNC=1 GHHPIJVNIUCRLD-CYBMUJFWSA-N 0.000 claims description 2
• ADQQOSPIQJDZIN-CYBMUJFWSA-N (2s)-2-[[5-chloro-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]amino]-2-(3-fluorophenyl)ethanol Chemical compound N([C@H](CO)C=1C=C(F)C=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NNC=1 ADQQOSPIQJDZIN-CYBMUJFWSA-N 0.000 claims description 2
• KKTWUGALTUFPNR-CYBMUJFWSA-N (2s)-2-[[5-chloro-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound N([C@H](CO)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NNC=1 KKTWUGALTUFPNR-CYBMUJFWSA-N 0.000 claims description 2
• WJTRZKOLMJCKOK-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2-fluorophenyl)ethanol Chemical compound C1=NN(CC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=CC=2)F)=N1 WJTRZKOLMJCKOK-OAHLLOKOSA-N 0.000 claims description 2
• ZXSVYJNRLDWVSN-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2-methoxyphenyl)ethanol Chemical compound C1=NN(CC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=CC=2)OC)=N1 ZXSVYJNRLDWVSN-OAHLLOKOSA-N 0.000 claims description 2
• YKQWFJMZPAGVCO-MRXNPFEDSA-N (2s)-2-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(3-methoxyphenyl)ethanol Chemical compound C1=NN(CC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(OC)C=CC=2)=N1 YKQWFJMZPAGVCO-MRXNPFEDSA-N 0.000 claims description 2
• SRXFYWKVPABCPB-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-pyridin-3-ylethanol Chemical compound C1=NN(CC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=NC=CC=2)=N1 SRXFYWKVPABCPB-CQSZACIVSA-N 0.000 claims description 2
• YKIWOVFZCRFHFX-CYBMUJFWSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-3-yl)amino]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound CN1C=CC(NC=2N=C(N[C@H](CO)C=3C=CC=CC=3)C(Cl)=CN=2)=N1 YKIWOVFZCRFHFX-CYBMUJFWSA-N 0.000 claims description 2
• WNAVYYSDFDNZGV-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2-fluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=CC=2)F)=N1 WNAVYYSDFDNZGV-CQSZACIVSA-N 0.000 claims description 2
• MMUMFSOUTIHSSK-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2-methoxyphenyl)ethanol Chemical compound COC1=CC=CC=C1[C@@H](CO)NC1=NC(NC2=CN(C)N=C2)=NC=C1Cl MMUMFSOUTIHSSK-CQSZACIVSA-N 0.000 claims description 2
• IENUHAKGQXATMC-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(3-fluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(F)C=CC=2)=N1 IENUHAKGQXATMC-CQSZACIVSA-N 0.000 claims description 2
• ZZIKCPQEINCIBY-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(3-methoxyphenyl)ethanol Chemical compound COC1=CC=CC([C@@H](CO)NC=2C(=CN=C(NC3=CN(C)N=C3)N=2)Cl)=C1 ZZIKCPQEINCIBY-OAHLLOKOSA-N 0.000 claims description 2
• DEXQVSWVAHWJPK-GOSISDBHSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-[3-(1-methylpyrazol-4-yl)phenyl]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(C=CC=2)C2=CN(C)N=C2)=N1 DEXQVSWVAHWJPK-GOSISDBHSA-N 0.000 claims description 2
• QOHXWGSDOSTOJA-GOSISDBHSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-[3-fluoro-5-(1-methylpyrazol-4-yl)phenyl]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(C=C(F)C=2)C2=CN(C)N=C2)=N1 QOHXWGSDOSTOJA-GOSISDBHSA-N 0.000 claims description 2
• VKUCDVJMGBPAAJ-SFHVURJKSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-phenyl-1-piperidin-1-ylethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](C(=O)N2CCCCC2)C=2C=CC=CC=2)=N1 VKUCDVJMGBPAAJ-SFHVURJKSA-N 0.000 claims description 2
• BCZVKTPLCCBQKI-KRWDZBQOSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-phenyl-1-pyrrolidin-1-ylethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](C(=O)N2CCCC2)C=2C=CC=CC=2)=N1 BCZVKTPLCCBQKI-KRWDZBQOSA-N 0.000 claims description 2
• RXQRUYJJCNKFIQ-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 RXQRUYJJCNKFIQ-CQSZACIVSA-N 0.000 claims description 2
• CDIGVRQLUFGRRZ-CYBMUJFWSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-pyridin-3-ylethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=NC=CC=2)=N1 CDIGVRQLUFGRRZ-CYBMUJFWSA-N 0.000 claims description 2
• WYKFXRHIIVPURK-HNNXBMFYSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-(2-hydroxyethyl)-2-phenylacetamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](C(=O)NCCO)C=2C=CC=CC=2)=N1 WYKFXRHIIVPURK-HNNXBMFYSA-N 0.000 claims description 2
• DHBOFEVPSKJZDG-INIZCTEOSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-(2-methoxyethyl)-2-phenylacetamide Chemical compound N([C@H](C(=O)NCCOC)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 DHBOFEVPSKJZDG-INIZCTEOSA-N 0.000 claims description 2
• NUOFTMVVHQUZGO-SFHVURJKSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-cyclopentyl-2-phenylacetamide Chemical class C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](C(=O)NC2CCCC2)C=2C=CC=CC=2)=N1 NUOFTMVVHQUZGO-SFHVURJKSA-N 0.000 claims description 2
• VAEZNBCTCPXOEY-HNNXBMFYSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-ethyl-2-phenylacetamide Chemical compound N([C@H](C(=O)NCC)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 VAEZNBCTCPXOEY-HNNXBMFYSA-N 0.000 claims description 2
• IWCMSDDIRYMGNN-AWEZNQCLSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methyl-2-phenylacetamide Chemical compound N([C@H](C(=O)NC)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 IWCMSDDIRYMGNN-AWEZNQCLSA-N 0.000 claims description 2
• RSGVOJRSLUEJIB-MRXNPFEDSA-N (2s)-2-[[5-chloro-2-[(1-propan-2-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2-fluorophenyl)ethanol Chemical compound C1=NN(C(C)C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=CC=2)F)=N1 RSGVOJRSLUEJIB-MRXNPFEDSA-N 0.000 claims description 2
• YKLSOBAPDFODQO-MRXNPFEDSA-N (2s)-2-[[5-chloro-2-[(1-propan-2-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2-methoxyphenyl)ethanol Chemical compound COC1=CC=CC=C1[C@@H](CO)NC1=NC(NC2=CN(N=C2)C(C)C)=NC=C1Cl YKLSOBAPDFODQO-MRXNPFEDSA-N 0.000 claims description 2
• KHDOTATXPPYSRM-QGZVFWFLSA-N (2s)-2-[[5-chloro-2-[(1-propan-2-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(3-methoxyphenyl)ethanol Chemical compound COC1=CC=CC([C@@H](CO)NC=2C(=CN=C(NC3=CN(N=C3)C(C)C)N=2)Cl)=C1 KHDOTATXPPYSRM-QGZVFWFLSA-N 0.000 claims description 2
• LAPQLBXPBRWDHE-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[(1-propan-2-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-pyridin-3-ylethanol Chemical compound C1=NN(C(C)C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=NC=CC=2)=N1 LAPQLBXPBRWDHE-OAHLLOKOSA-N 0.000 claims description 2
• MRSQWFHDCSVGCF-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(2-fluorophenyl)ethanol Chemical compound N([C@H](CO)C=1C(=CC=CC=1)F)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(F)F)C=1 MRSQWFHDCSVGCF-CQSZACIVSA-N 0.000 claims description 2
• VLVBFDWOLPFQSL-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(2-fluorophenyl)ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=CC=2)F)=N1 VLVBFDWOLPFQSL-OAHLLOKOSA-N 0.000 claims description 2
• AJBNNIRGRQTWJS-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(2-methoxyphenyl)ethanol Chemical compound COC1=CC=CC=C1[C@@H](CO)NC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl AJBNNIRGRQTWJS-OAHLLOKOSA-N 0.000 claims description 2
• GZAUZHXRHFRDOK-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(3,5-difluorophenyl)ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)=N1 GZAUZHXRHFRDOK-OAHLLOKOSA-N 0.000 claims description 2
• CKOSHJVGYPLDMB-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(3-fluorophenyl)ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(F)C=CC=2)=N1 CKOSHJVGYPLDMB-OAHLLOKOSA-N 0.000 claims description 2
• WJIXMUBFHZXTCZ-MRXNPFEDSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(3-methoxyphenyl)ethanol Chemical compound COC1=CC=CC([C@@H](CO)NC=2C(=CN=C(NC3=CN(CCO)N=C3)N=2)Cl)=C1 WJIXMUBFHZXTCZ-MRXNPFEDSA-N 0.000 claims description 2
• IBNVHZOHLPFNTD-LJQANCHMSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-[3-(1-methylpyrazol-4-yl)phenyl]ethanol Chemical compound C1=NN(C)C=C1C1=CC=CC([C@@H](CO)NC=2C(=CN=C(NC3=CN(CCO)N=C3)N=2)Cl)=C1 IBNVHZOHLPFNTD-LJQANCHMSA-N 0.000 claims description 2
• POVHSKOBBQQZRQ-LJQANCHMSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-[3-fluoro-5-(1-methylpyrazol-4-yl)phenyl]ethanol Chemical compound C1=NN(C)C=C1C1=CC(F)=CC([C@@H](CO)NC=2C(=CN=C(NC3=CN(CCO)N=C3)N=2)Cl)=C1 POVHSKOBBQQZRQ-LJQANCHMSA-N 0.000 claims description 2
• XMNALHSLGADDHY-IBGZPJMESA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-phenyl-1-piperidin-1-ylethanone Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](C(=O)N2CCCCC2)C=2C=CC=CC=2)=N1 XMNALHSLGADDHY-IBGZPJMESA-N 0.000 claims description 2
• JGMJIRRCDLKALH-SFHVURJKSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-phenyl-1-pyrrolidin-1-ylethanone Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](C(=O)N2CCCC2)C=2C=CC=CC=2)=N1 JGMJIRRCDLKALH-SFHVURJKSA-N 0.000 claims description 2
• WPKBELRPTDQFFT-OAHLLOKOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 WPKBELRPTDQFFT-OAHLLOKOSA-N 0.000 claims description 2
• FOFRZBWOODJWCY-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-pyridin-2-ylethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2N=CC=CC=2)=N1 FOFRZBWOODJWCY-CQSZACIVSA-N 0.000 claims description 2
• OQPJLEVRKAILTG-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-pyridin-3-ylethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=NC=CC=2)=N1 OQPJLEVRKAILTG-CQSZACIVSA-N 0.000 claims description 2
• IZXDFTRTTAYOMG-INIZCTEOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-n,n-dimethyl-2-phenylacetamide Chemical compound N([C@H](C(=O)N(C)C)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 IZXDFTRTTAYOMG-INIZCTEOSA-N 0.000 claims description 2
• SZWJXPMMDUIZNT-INIZCTEOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-n-(2-hydroxyethyl)-2-phenylacetamide Chemical compound N([C@H](C(=O)NCCO)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 SZWJXPMMDUIZNT-INIZCTEOSA-N 0.000 claims description 2
• FGDFHWKZSWVVQM-KRWDZBQOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-n-(2-methoxyethyl)-2-phenylacetamide Chemical compound N([C@H](C(=O)NCCOC)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 FGDFHWKZSWVVQM-KRWDZBQOSA-N 0.000 claims description 2
• NKICVQQHIJMPIM-IBGZPJMESA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-n-cyclopentyl-2-phenylacetamide Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(N[C@H](C(=O)NC2CCCC2)C=2C=CC=CC=2)=N1 NKICVQQHIJMPIM-IBGZPJMESA-N 0.000 claims description 2
• DQWHPKFYJWLKBB-INIZCTEOSA-N (2s)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-n-ethyl-2-phenylacetamide Chemical compound N([C@H](C(=O)NCC)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 DQWHPKFYJWLKBB-INIZCTEOSA-N 0.000 claims description 2
• MTLMXSICCGZNNV-GOSISDBHSA-N (2s)-2-[[5-chloro-2-[[1-(2-propan-2-yloxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound C1=NN(CCOC(C)C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 MTLMXSICCGZNNV-GOSISDBHSA-N 0.000 claims description 2
• DIEBUARHSHTNBW-GOSISDBHSA-N (2s)-2-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-[3-fluoro-5-(1-methylpyrazol-4-yl)phenyl]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(C=C(F)C=2)C2=CN(C)N=C2)=N1 DIEBUARHSHTNBW-GOSISDBHSA-N 0.000 claims description 2
• NNWDPHCQEGUJRY-CQSZACIVSA-N (2s)-2-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=CC=CC=2)=N1 NNWDPHCQEGUJRY-CQSZACIVSA-N 0.000 claims description 2
• OBZKXCCWVJJJOO-LJQANCHMSA-N (2s)-2-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-[3-fluoro-5-(1-methylpyrazol-4-yl)phenyl]ethanol Chemical compound C1=NN(C)C=C1C1=CC(F)=CC([C@@H](CO)NC=2C(=CN=C(NC3=CN(CCO)N=C3)N=2)F)=C1 OBZKXCCWVJJJOO-LJQANCHMSA-N 0.000 claims description 2
• OAESFYMINDDZBR-OAHLLOKOSA-N (2s)-2-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=CC=CC=2)=N1 OAESFYMINDDZBR-OAHLLOKOSA-N 0.000 claims description 2
• MLDIFTQKQFXKBK-LJQANCHMSA-N (2s)-2-[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-[3-(1-methylpyrazol-4-yl)phenyl]ethanol Chemical compound N1=C(N[C@H](CO)C=2C=C(C=CC=2)C2=CN(C)N=C2)C(C)=CN=C1NC=1C=NN(C)C=1 MLDIFTQKQFXKBK-LJQANCHMSA-N 0.000 claims description 2
• OXPHMZRLGGDLSW-MRXNPFEDSA-N (3r)-3-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-3-phenylpropan-1-ol Chemical compound N([C@H](CCO)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 OXPHMZRLGGDLSW-MRXNPFEDSA-N 0.000 claims description 2
• MUMXWBCEQYHPQM-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[[1-(2,6-difluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=NN(CC(C)(O)C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2F)F)=N1 MUMXWBCEQYHPQM-UHFFFAOYSA-N 0.000 claims description 2
• KLVWDWKRSPLROB-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[[1-(2,6-difluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]propan-2-ol Chemical compound C1=NN(CC(O)C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2F)F)=N1 KLVWDWKRSPLROB-UHFFFAOYSA-N 0.000 claims description 2
• YGXUTJPJGREDDU-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[[1-(2-fluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=NN(CC(C)(O)C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2)F)=N1 YGXUTJPJGREDDU-UHFFFAOYSA-N 0.000 claims description 2
• MVHLPXLVIAEQNS-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[[1-(3-fluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=NN(CC(C)(O)C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=C(F)C=CC=2)=N1 MVHLPXLVIAEQNS-UHFFFAOYSA-N 0.000 claims description 2
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• CANMIUFARMZZQH-UHFFFAOYSA-N 2-(3-bromophenyl)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=C(Br)C=CC=2)=N1 CANMIUFARMZZQH-UHFFFAOYSA-N 0.000 claims description 2
• NGIMWXFLGMKNKL-UHFFFAOYSA-N 2-(3-bromophenyl)-2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=C(Br)C=CC=2)=N1 NGIMWXFLGMKNKL-UHFFFAOYSA-N 0.000 claims description 2
• HZWHPSHPFJZOBM-OAHLLOKOSA-N 2-[4-[[4-[[(1s)-1-(3,5-difluorophenyl)-2-hydroxyethyl]amino]-5-fluoropyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)=N1 HZWHPSHPFJZOBM-OAHLLOKOSA-N 0.000 claims description 2
• DKKGOQXABNRTIZ-OAHLLOKOSA-N 2-[4-[[4-[[(1s)-1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl]amino]-5-chloropyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(Br)C=C(F)C=2)=N1 DKKGOQXABNRTIZ-OAHLLOKOSA-N 0.000 claims description 2
• FTYABEOOWNWEFE-OAHLLOKOSA-N 2-[4-[[4-[[(1s)-1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl]amino]-5-fluoropyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(Br)C=C(F)C=2)=N1 FTYABEOOWNWEFE-OAHLLOKOSA-N 0.000 claims description 2
• SPYOWRPDXOMFTO-OAHLLOKOSA-N 2-[4-[[4-[[(1s)-1-(3-bromophenyl)-2-hydroxyethyl]amino]-5-fluoropyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(Br)C=CC=2)=N1 SPYOWRPDXOMFTO-OAHLLOKOSA-N 0.000 claims description 2
• FPXLPILAGKHEDV-QGZVFWFLSA-N 2-[4-[[4-[[(1s)-2-hydroxy-1-phenylethyl]amino]-5-methylpyrimidin-2-yl]amino]pyrazol-1-yl]-n,n-dimethylacetamide Chemical compound C1=NN(CC(=O)N(C)C)C=C1NC1=NC=C(C)C(N[C@H](CO)C=2C=CC=CC=2)=N1 FPXLPILAGKHEDV-QGZVFWFLSA-N 0.000 claims description 2
• QRTGNUWINGYOEI-MRXNPFEDSA-N 2-[4-[[4-[[(1s)-2-hydroxy-1-phenylethyl]amino]-5-methylpyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(C)C(N[C@H](CO)C=2C=CC=CC=2)=N1 QRTGNUWINGYOEI-MRXNPFEDSA-N 0.000 claims description 2
• RDJNHPLPOCUGRU-UHFFFAOYSA-N 2-[4-[[4-[[1-(2,6-difluorophenyl)-2-hydroxyethyl]amino]-5-methylpyrimidin-2-yl]amino]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound N1=C(NC(CO)C=2C(=CC=CC=2F)F)C(C)=CN=C1NC(=C1)C=NN1CC(=O)N1CCOCC1 RDJNHPLPOCUGRU-UHFFFAOYSA-N 0.000 claims description 2
• YGILEGKGACRRRC-MRXNPFEDSA-N 2-[4-[[5-chloro-4-[[(1r)-3-hydroxy-1-phenylpropyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(N[C@H](CCO)C=2C=CC=CC=2)=N1 YGILEGKGACRRRC-MRXNPFEDSA-N 0.000 claims description 2
• HUMUXEVIMMREDK-OAHLLOKOSA-N 2-[4-[[5-chloro-4-[[(1s)-1-(2,5-difluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=C(F)C=2)F)=N1 HUMUXEVIMMREDK-OAHLLOKOSA-N 0.000 claims description 2
• ZLJRYJRUYVSVSG-OAHLLOKOSA-N 2-[4-[[5-chloro-4-[[(1s)-1-(3,5-difluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)=N1 ZLJRYJRUYVSVSG-OAHLLOKOSA-N 0.000 claims description 2
• BSRVFAWSQMGAPT-LJQANCHMSA-N 2-[4-[[5-chloro-4-[[(1s)-1-[3-fluoro-5-(1-methylpyrazol-4-yl)phenyl]-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(C=C(F)C=2)C2=CN(C)N=C2)=N1 BSRVFAWSQMGAPT-LJQANCHMSA-N 0.000 claims description 2
• IHOSXXLJIKORCO-MRXNPFEDSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n,n-dimethylacetamide Chemical compound C1=NN(CC(=O)N(C)C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 IHOSXXLJIKORCO-MRXNPFEDSA-N 0.000 claims description 2
• GPFKXICOVDFZMW-QGZVFWFLSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-(cyanomethyl)-n-methylacetamide Chemical compound C1=NN(CC(=O)N(CC#N)C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 GPFKXICOVDFZMW-QGZVFWFLSA-N 0.000 claims description 2
• BOZRKGFACHXBTC-QGZVFWFLSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-cyclopropylacetamide Chemical compound N([C@H](CO)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC(=O)NC1CC1 BOZRKGFACHXBTC-QGZVFWFLSA-N 0.000 claims description 2
• QRACHGKPVCWUJS-QGZVFWFLSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-propan-2-ylacetamide Chemical compound C1=NN(CC(=O)NC(C)C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=CC=CC=2)=N1 QRACHGKPVCWUJS-QGZVFWFLSA-N 0.000 claims description 2
• BXZRGUOBAPEQJB-CQSZACIVSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]acetic acid Chemical compound N([C@H](CO)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(O)=O)C=1 BXZRGUOBAPEQJB-CQSZACIVSA-N 0.000 claims description 2
• HUMUXEVIMMREDK-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[[1-(2,5-difluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=C(F)C=2)F)=N1 HUMUXEVIMMREDK-UHFFFAOYSA-N 0.000 claims description 2
• PELNHYKIWGWPBO-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[[1-(2,6-difluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2F)F)=N1 PELNHYKIWGWPBO-UHFFFAOYSA-N 0.000 claims description 2
• AQXKPRDBZPRXCH-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[[1-(2-chlorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2)Cl)=N1 AQXKPRDBZPRXCH-UHFFFAOYSA-N 0.000 claims description 2
• DAYLRTJATXIQNI-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[[1-(2-fluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2)F)=N1 DAYLRTJATXIQNI-UHFFFAOYSA-N 0.000 claims description 2
• ZLJRYJRUYVSVSG-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[[1-(3,5-difluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=C(F)C=C(F)C=2)=N1 ZLJRYJRUYVSVSG-UHFFFAOYSA-N 0.000 claims description 2
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