JP2014521623A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014521623A5 JP2014521623A5 JP2014522067A JP2014522067A JP2014521623A5 JP 2014521623 A5 JP2014521623 A5 JP 2014521623A5 JP 2014522067 A JP2014522067 A JP 2014522067A JP 2014522067 A JP2014522067 A JP 2014522067A JP 2014521623 A5 JP2014521623 A5 JP 2014521623A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- pyrazol
- pyrimidin
- chloro
- hydroxyethyl
- Prior art date
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 26
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
- -1 3- (2-oxa-6-azaspiro [3.3] heptane-6-yl) phenyl Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 230000000155 isotopic effect Effects 0.000 claims 3
- 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 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- YWAUQSFUTBZFMJ-CQSZACIVSA-N (2s)-2-(2,5-difluorophenyl)-2-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C(=CC=C(F)C=2)F)=N1 YWAUQSFUTBZFMJ-CQSZACIVSA-N 0.000 claims 1
- 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 1
- FFCIMDGIZAZOGN-CQSZACIVSA-N (2s)-2-(3,5-difluorophenyl)-2-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)=N1 FFCIMDGIZAZOGN-CQSZACIVSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- ALZYRQUSZSTJID-CQSZACIVSA-N (2s)-2-(3-bromo-5-fluorophenyl)-2-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(N[C@H](CO)C=2C=C(Br)C=C(F)C=2)=N1 ALZYRQUSZSTJID-CQSZACIVSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- NLBLZALOYCDNAW-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2,5-difluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=C(F)C=2)F)=N1 NLBLZALOYCDNAW-CQSZACIVSA-N 0.000 claims 1
- 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 1
- 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 1
- RFIUFRRMSPKJFK-CQSZACIVSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(3,5-difluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(F)C=C(F)C=2)=N1 RFIUFRRMSPKJFK-CQSZACIVSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- VWLXZDUUVRDYGP-HNNXBMFYSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-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(C)C=1 VWLXZDUUVRDYGP-HNNXBMFYSA-N 0.000 claims 1
- 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 1
- 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 1
- NUOFTMVVHQUZGO-SFHVURJKSA-N (2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-cyclopentyl-2-phenylacetamide Chemical compound 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- QFMZTHIJEQORIC-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[[1-(3-fluorophenyl)-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=C(F)C=CC=2)=N1 QFMZTHIJEQORIC-UHFFFAOYSA-N 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- MATVWFGDKHOHCG-OAHLLOKOSA-N 2-[4-[[4-[[(1s)-1-(2,5-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(=CC=C(F)C=2)F)=N1 MATVWFGDKHOHCG-OAHLLOKOSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- USGOMFLMIAOXDT-OAHLLOKOSA-N 2-[4-[[4-[[(1s)-1-(3-bromophenyl)-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=CC=2)=N1 USGOMFLMIAOXDT-OAHLLOKOSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- SHEZPHYTOIDNBA-GOSISDBHSA-N 2-[4-[[5-chloro-4-[[(1s)-1-(2-fluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound N([C@H](CO)C=1C(=CC=CC=1)F)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC(=O)N1CCOCC1 SHEZPHYTOIDNBA-GOSISDBHSA-N 0.000 claims 1
- AWTYKPFGZFAAMX-OAHLLOKOSA-N 2-[4-[[5-chloro-4-[[(1s)-1-(2-fluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropanamide Chemical compound C1=NN(C(C)(C(N)=O)C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=CC=CC=2)F)=N1 AWTYKPFGZFAAMX-OAHLLOKOSA-N 0.000 claims 1
- DAYLRTJATXIQNI-OAHLLOKOSA-N 2-[4-[[5-chloro-4-[[(1s)-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(N[C@H](CO)C=2C(=CC=CC=2)F)=N1 DAYLRTJATXIQNI-OAHLLOKOSA-N 0.000 claims 1
- IKGBIPDYEDIGQC-QGZVFWFLSA-N 2-[4-[[5-chloro-4-[[(1s)-1-(2-fluorophenyl)-2-hydroxyethyl]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)F)=N1 IKGBIPDYEDIGQC-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- MRYQRNALJMYYIO-GOSISDBHSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-(2-methoxyphenyl)ethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound COC1=CC=CC=C1[C@@H](CO)NC1=NC(NC2=CN(CC(=O)N3CCOCC3)N=C2)=NC=C1Cl MRYQRNALJMYYIO-GOSISDBHSA-N 0.000 claims 1
- MZLRVVZENQSDRD-OAHLLOKOSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-(2-methoxyphenyl)ethyl]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)OC)=N1 MZLRVVZENQSDRD-OAHLLOKOSA-N 0.000 claims 1
- JIPXQCNZMBTTRN-LJQANCHMSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-(3-methoxyphenyl)ethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound COC1=CC=CC([C@@H](CO)NC=2C(=CN=C(NC3=CN(CC(=O)N4CCOCC4)N=C3)N=2)Cl)=C1 JIPXQCNZMBTTRN-LJQANCHMSA-N 0.000 claims 1
- FTKYNEPIWUGBGC-MRXNPFEDSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-(3-methoxyphenyl)ethyl]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(OC)C=CC=2)=N1 FTKYNEPIWUGBGC-MRXNPFEDSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- PUXWPVMRSTXHFF-QGZVFWFLSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-pyridin-3-ylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound N([C@H](CO)C=1C=NC=CC=1)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC(=O)N1CCOCC1 PUXWPVMRSTXHFF-QGZVFWFLSA-N 0.000 claims 1
- UWEJVMVPKSJHKW-CQSZACIVSA-N 2-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-pyridin-3-ylethyl]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=NC=CC=2)=N1 UWEJVMVPKSJHKW-CQSZACIVSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- XTAKUCIMHVOHFR-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[[1-(3-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=C(F)C=CC=2)=N1 XTAKUCIMHVOHFR-UHFFFAOYSA-N 0.000 claims 1
- AFECMOMSJHWJEF-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[[2-hydroxy-1-[2-(trifluoromethyl)phenyl]ethyl]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)C(F)(F)F)=N1 AFECMOMSJHWJEF-UHFFFAOYSA-N 0.000 claims 1
- XBUXORGIIBDVFL-GOSISDBHSA-N 2-[4-[[5-fluoro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound N([C@H](CO)C=1C=CC=CC=1)C(C(=CN=1)F)=NC=1NC(=C1)C=NN1CC(=O)N1CCOCC1 XBUXORGIIBDVFL-GOSISDBHSA-N 0.000 claims 1
- HNXUEVFTQBHCDE-OAHLLOKOSA-N 2-[4-[[5-fluoro-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(F)C(N[C@H](CO)C=2C=CC=CC=2)=N1 HNXUEVFTQBHCDE-OAHLLOKOSA-N 0.000 claims 1
- BLCMNWHCMNPEHE-UHFFFAOYSA-N 2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]-2-phenylpropan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC(C)(CO)C=2C=CC=CC=2)=N1 BLCMNWHCMNPEHE-UHFFFAOYSA-N 0.000 claims 1
- XRIZGSIEKUHTRL-UHFFFAOYSA-N 2-[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]-2-(2,6-difluorophenyl)ethanol Chemical compound N1=C(NC(CO)C=2C(=CC=CC=2F)F)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 XRIZGSIEKUHTRL-UHFFFAOYSA-N 0.000 claims 1
- KUFAIPDLGPKRFP-UHFFFAOYSA-N 2-[[2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]-2-phenylethanol Chemical compound N1=C(NC(CO)C=2C=CC=CC=2)C(C)=CN=C1NC=1C=NN(CCO)C=1 KUFAIPDLGPKRFP-UHFFFAOYSA-N 0.000 claims 1
- NLBLZALOYCDNAW-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2,5-difluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=C(F)C=2)F)=N1 NLBLZALOYCDNAW-UHFFFAOYSA-N 0.000 claims 1
- BPPSZYPDHVBYLR-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2,6-difluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2F)F)=N1 BPPSZYPDHVBYLR-UHFFFAOYSA-N 0.000 claims 1
- YHAKQDUQTYCBOR-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(2-chlorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2)Cl)=N1 YHAKQDUQTYCBOR-UHFFFAOYSA-N 0.000 claims 1
- WNAVYYSDFDNZGV-UHFFFAOYSA-N 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(NC(CO)C=2C(=CC=CC=2)F)=N1 WNAVYYSDFDNZGV-UHFFFAOYSA-N 0.000 claims 1
- RFIUFRRMSPKJFK-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(3,5-difluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=C(F)C=C(F)C=2)=N1 RFIUFRRMSPKJFK-UHFFFAOYSA-N 0.000 claims 1
- IENUHAKGQXATMC-UHFFFAOYSA-N 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(NC(CO)C=2C=C(F)C=CC=2)=N1 IENUHAKGQXATMC-UHFFFAOYSA-N 0.000 claims 1
- HFXNLXDAQFJBDX-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-(4-fluorophenyl)ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=CC(F)=CC=2)=N1 HFXNLXDAQFJBDX-UHFFFAOYSA-N 0.000 claims 1
- DEXQVSWVAHWJPK-UHFFFAOYSA-N 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(NC(CO)C=2C=C(C=CC=2)C2=CN(C)N=C2)=N1 DEXQVSWVAHWJPK-UHFFFAOYSA-N 0.000 claims 1
- HUJJMUALWOHJSQ-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-phenylacetic acid Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(C(O)=O)C=2C=CC=CC=2)=N1 HUJJMUALWOHJSQ-UHFFFAOYSA-N 0.000 claims 1
- RXQRUYJJCNKFIQ-UHFFFAOYSA-N 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(NC(CO)C=2C=CC=CC=2)=N1 RXQRUYJJCNKFIQ-UHFFFAOYSA-N 0.000 claims 1
- CKCSDFJODCGFLT-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-phenylpropan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(C)(CO)C=2C=CC=CC=2)=N1 CKCSDFJODCGFLT-UHFFFAOYSA-N 0.000 claims 1
- PEJLEKFNMPWERQ-UHFFFAOYSA-N 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-3-phenylpropan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)CC=2C=CC=CC=2)=N1 PEJLEKFNMPWERQ-UHFFFAOYSA-N 0.000 claims 1
- YIDFEZROOALWON-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-3-yl]amino]pyrimidin-4-yl]amino]-2-(2,6-difluorophenyl)ethanol Chemical compound OCCN1C=CC(NC=2N=C(NC(CO)C=3C(=CC=CC=3F)F)C(Cl)=CN=2)=N1 YIDFEZROOALWON-UHFFFAOYSA-N 0.000 claims 1
- DYDOSUQNRBPGDA-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-3-yl]amino]pyrimidin-4-yl]amino]-2-(2-fluorophenyl)ethanol Chemical compound OCCN1C=CC(NC=2N=C(NC(CO)C=3C(=CC=CC=3)F)C(Cl)=CN=2)=N1 DYDOSUQNRBPGDA-UHFFFAOYSA-N 0.000 claims 1
- PPVCISMXHZQIIT-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-3-yl]amino]pyrimidin-4-yl]amino]-2-(3-fluorophenyl)ethanol Chemical compound OCCN1C=CC(NC=2N=C(NC(CO)C=3C=C(F)C=CC=3)C(Cl)=CN=2)=N1 PPVCISMXHZQIIT-UHFFFAOYSA-N 0.000 claims 1
- BKLXVHYHAOHCGE-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(2,6-difluorophenyl)ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2F)F)=N1 BKLXVHYHAOHCGE-UHFFFAOYSA-N 0.000 claims 1
- LDNHSVKRTAUBMS-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(2-chlorophenyl)ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2)Cl)=N1 LDNHSVKRTAUBMS-UHFFFAOYSA-N 0.000 claims 1
- SHQAXVFIOUEHHQ-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(2-fluorophenyl)-n,n-dimethylacetamide Chemical compound C=1C=CC=C(F)C=1C(C(=O)N(C)C)NC(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 SHQAXVFIOUEHHQ-UHFFFAOYSA-N 0.000 claims 1
- VLVBFDWOLPFQSL-UHFFFAOYSA-N 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(NC(CO)C=2C(=CC=CC=2)F)=N1 VLVBFDWOLPFQSL-UHFFFAOYSA-N 0.000 claims 1
- GZAUZHXRHFRDOK-UHFFFAOYSA-N 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(NC(CO)C=2C=C(F)C=C(F)C=2)=N1 GZAUZHXRHFRDOK-UHFFFAOYSA-N 0.000 claims 1
- CKOSHJVGYPLDMB-UHFFFAOYSA-N 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(NC(CO)C=2C=C(F)C=CC=2)=N1 CKOSHJVGYPLDMB-UHFFFAOYSA-N 0.000 claims 1
- HSDQSYSOTPPXKW-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-(4-fluorophenyl)ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=CC(F)=CC=2)=N1 HSDQSYSOTPPXKW-UHFFFAOYSA-N 0.000 claims 1
- IBNVHZOHLPFNTD-UHFFFAOYSA-N 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(CO)NC=2C(=CN=C(NC3=CN(CCO)N=C3)N=2)Cl)=C1 IBNVHZOHLPFNTD-UHFFFAOYSA-N 0.000 claims 1
- IWBJSQDRZQXPDW-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-phenylacetic acid Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC(C(O)=O)C=2C=CC=CC=2)=N1 IWBJSQDRZQXPDW-UHFFFAOYSA-N 0.000 claims 1
- LMRYRVSDUAONDY-UHFFFAOYSA-N 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-3-phenylpropan-1-ol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC(CO)CC=2C=CC=CC=2)=N1 LMRYRVSDUAONDY-UHFFFAOYSA-N 0.000 claims 1
- NNWDPHCQEGUJRY-UHFFFAOYSA-N 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(NC(CO)C=2C=CC=CC=2)=N1 NNWDPHCQEGUJRY-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- BFFOKLCANWDYEI-TZHYSIJRSA-N 3-[4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]-1-methylpyrrolidin-2-one Chemical compound O=C1N(C)CCC1N1N=CC(NC=2N=C(N[C@H](CO)C=3C=CC=CC=3)C(Cl)=CN=2)=C1 BFFOKLCANWDYEI-TZHYSIJRSA-N 0.000 claims 1
- FIHAVFRNXRCMLA-UHFFFAOYSA-N 3-[4-[[5-chloro-4-[[1-(2-fluorophenyl)-2-hydroxyethyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]propan-1-ol Chemical compound C1=NN(CCCO)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C(=CC=CC=2)F)=N1 FIHAVFRNXRCMLA-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- QTCMSVLPQGNMAW-OAHLLOKOSA-N 4-[3-[(1s)-1-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-hydroxyethyl]-2-fluorophenyl]morpholin-3-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C(=C(N3C(COCC3)=O)C=CC=2)F)=N1 QTCMSVLPQGNMAW-OAHLLOKOSA-N 0.000 claims 1
- UIUHEIIXARGKHM-QGZVFWFLSA-N 4-[3-[(1s)-1-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-hydroxyethyl]phenyl]morpholin-3-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H](CO)C=2C=C(C=CC=2)N2C(COCC2)=O)=N1 UIUHEIIXARGKHM-QGZVFWFLSA-N 0.000 claims 1
- UIUHEIIXARGKHM-UHFFFAOYSA-N 4-[3-[1-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-hydroxyethyl]phenyl]morpholin-3-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC(CO)C=2C=C(C=CC=2)N2C(COCC2)=O)=N1 UIUHEIIXARGKHM-UHFFFAOYSA-N 0.000 claims 1
- SFZMGXXIJQGYCY-OAHLLOKOSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[(1r)-1-phenylpropyl]pyrimidine-2,4-diamine Chemical compound N([C@H](CC)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 SFZMGXXIJQGYCY-OAHLLOKOSA-N 0.000 claims 1
- SKQPZCXHGMDQFX-OAHLLOKOSA-N 5-chloro-4-n-[(1s)-2-methoxy-1-phenylethyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound N([C@H](COC)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 SKQPZCXHGMDQFX-OAHLLOKOSA-N 0.000 claims 1
- ZULKNANRYDTNQM-UHFFFAOYSA-N 5-chloro-4-n-[1-(2-fluorophenyl)propyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C=CC=C(F)C=1C(CC)NC(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 ZULKNANRYDTNQM-UHFFFAOYSA-N 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- IZNSYIUZDFSDST-GOSISDBHSA-N [4-[[5-chloro-4-[[(1s)-2-hydroxy-1-phenylethyl]amino]pyrimidin-2-yl]amino]-1h-pyrrol-2-yl]-morpholin-4-ylmethanone Chemical compound N([C@H](CO)C=1C=CC=CC=1)C(C(=CN=1)Cl)=NC=1NC(C=1)=CNC=1C(=O)N1CCOCC1 IZNSYIUZDFSDST-GOSISDBHSA-N 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 230000001900 immune effect Effects 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- JUJANQURVOHWIV-UHFFFAOYSA-N methyl 2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)NC(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 JUJANQURVOHWIV-UHFFFAOYSA-N 0.000 claims 1
- WGLLYVGBKSOUQO-UHFFFAOYSA-N methyl 2-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)NC(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 WGLLYVGBKSOUQO-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 0 CC1=C(*)C*C(*(C2(/C3=C\C=C\C(C4)=C4/C=C3)NN=NC2)=C)=*1 Chemical compound CC1=C(*)C*C(*(C2(/C3=C\C=C\C(C4)=C4/C=C3)NN=NC2)=C)=*1 0.000 description 2
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11175807 | 2011-07-28 | ||
| EP11175807.4 | 2011-07-28 | ||
| US201261635921P | 2012-04-20 | 2012-04-20 | |
| US61/635,921 | 2012-04-20 | ||
| PCT/EP2012/064515 WO2013014162A1 (en) | 2011-07-28 | 2012-07-24 | Heterocyclyl pyrimidine analogues as jak inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014521623A JP2014521623A (ja) | 2014-08-28 |
| JP2014521623A5 true JP2014521623A5 (https=) | 2015-09-10 |
Family
ID=47600533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014522067A Pending JP2014521623A (ja) | 2011-07-28 | 2012-07-24 | Ｊａｋ阻害剤としてのヘテロシクリルピリミジンアナログ |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20140179664A1 (https=) |
| EP (1) | EP2736901A1 (https=) |
| JP (1) | JP2014521623A (https=) |
| KR (1) | KR20140047092A (https=) |
| CN (1) | CN103781780B (https=) |
| AU (1) | AU2012288892B2 (https=) |
| BR (1) | BR112014000360A2 (https=) |
| CA (1) | CA2843195A1 (https=) |
| WO (1) | WO2013014162A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8765747B2 (en) | 2009-06-12 | 2014-07-01 | Dana-Farber Cancer Institute, Inc. | Fused 2-aminothiazole compounds |
| US9382239B2 (en) | 2011-11-17 | 2016-07-05 | Dana-Farber Cancer Institute, Inc. | Inhibitors of c-Jun-N-terminal kinase (JNK) |
| EP2909194A1 (en) | 2012-10-18 | 2015-08-26 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
| USRE48175E1 (en) | 2012-10-19 | 2020-08-25 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged small molecules as inducers of protein degradation |
| WO2014063054A1 (en) | 2012-10-19 | 2014-04-24 | Dana-Farber Cancer Institute, Inc. | Bone marrow on x chromosome kinase (bmx) inhibitors and uses thereof |
| WO2015058126A1 (en) | 2013-10-18 | 2015-04-23 | Syros Pharmaceuticals, Inc. | Heteroaromatic compounds useful for the treatment of prolferative diseases |
| EP3057956B1 (en) | 2013-10-18 | 2021-05-05 | Dana-Farber Cancer Institute, Inc. | Polycyclic inhibitors of cyclin-dependent kinase 7 (cdk7) |
| WO2015164614A1 (en) * | 2014-04-23 | 2015-10-29 | Dana-Farber Cancer Institute, Inc. | Janus kinase inhibitors and uses thereof |
| US9862688B2 (en) | 2014-04-23 | 2018-01-09 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged janus kinase inhibitors and uses thereof |
| JP6854762B2 (ja) | 2014-12-23 | 2021-04-07 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | サイクリン依存性キナーゼ７（ｃｄｋ７）の阻害剤 |
| USRE50776E1 (en) | 2015-03-27 | 2026-02-03 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| WO2016201370A1 (en) | 2015-06-12 | 2016-12-15 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
| AU2016319125B2 (en) | 2015-09-09 | 2021-04-08 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| BR112018006817A2 (pt) | 2015-10-08 | 2018-10-23 | Macrogenics Inc | método de tratamento do câncer |
| US11214565B2 (en) | 2015-11-20 | 2022-01-04 | Denali Therapeutics Inc. | Compound, compositions, and methods |
| US11028080B2 (en) | 2016-03-11 | 2021-06-08 | Denali Therapeutics Inc. | Substituted pyrimidines as LRKK2 inhibitors |
| SMT202100699T1 (it) | 2016-06-16 | 2022-01-10 | Denali Therapeutics Inc | Pirimidin-2-ilammino-1h-pirazoli come inibitori di lrrk2 per l'uso nel trattamento di disturbi neurodegenerativi |
| JP7117029B2 (ja) * | 2017-09-21 | 2022-08-12 | 北京賽特明強医薬科技有限公司 | ２－置換ピラゾールアミノ－４－置換アミノ－５－ピリミジンホルムアミド系化合物、組成物およびその使用 |
| CN109535132B (zh) * | 2017-09-21 | 2021-07-20 | 北京赛特明强医药科技有限公司 | 2-取代吡唑氨基-4-取代氨基-5-嘧啶甲酰胺类化合物、组合物及其应用 |
| JP7307729B2 (ja) | 2017-12-20 | 2023-07-12 | ヤンセン ファーマシューティカ エヌ．ベー． | メニン－ｍｌｌ相互作用のエキソ－アザスピロ阻害剤 |
| EP3810132A4 (en) | 2018-06-25 | 2022-06-22 | Dana-Farber Cancer Institute, Inc. | TAIRE FAMILY KINASE INHIBITORS AND RELATED USES |
| CN110734427B (zh) * | 2018-07-20 | 2021-01-15 | 北京赛特明强医药科技有限公司 | 含烯基的嘧啶甲酰胺类化合物、组合物及其应用 |
| CN110845476B (zh) * | 2018-08-21 | 2022-11-18 | 上海和誉生物医药科技有限公司 | 一种高选择性csf1r抑制剂、其制备方法和在药学上的应用 |
| EP3877371A4 (en) | 2018-11-07 | 2022-07-27 | Dana-Farber Cancer Institute, Inc. | IMIDAZOPYRIDINE DERIVATIVES AND AZA-IMIDAZOPYRIDINE DERIVATIVES AS JANUS KINASE 2 INHIBITORS AND USES THEREOF |
| EP3876939A4 (en) | 2018-11-07 | 2022-08-10 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| US12522583B2 (en) | 2018-11-07 | 2026-01-13 | Dana-Farber Cancer Institute, Inc. | Benzimidazole derivatives and aza-benzimidazole derivatives as Janus kinase 2 inhibitors and uses thereof |
| WO2020118683A1 (en) * | 2018-12-14 | 2020-06-18 | Lynk Pharmaceuticals Co. Ltd. | Benzamides of pyrazolyl-amino-pyrimidinyl derivatives, and compositions and methods thereof |
| US12281126B2 (en) | 2018-12-28 | 2025-04-22 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 and uses thereof |
| US11518758B2 (en) * | 2019-05-10 | 2022-12-06 | Deciphera Pharmaceuticals, Llc | Heteroarylaminopyrimidine amide autophagy inhibitors and methods of use thereof |
| PE20220597A1 (es) | 2019-05-10 | 2022-04-22 | Deciphera Pharmaceuticals Llc | Inhibidores de la autofagia de fenilaminopirimidina amida y metodos de uso de estos |
| PE20221083A1 (es) | 2019-06-17 | 2022-07-05 | Deciphera Pharmaceuticals Llc | Inhibidores de la autofagia de la amida aminopirimidina y sus metodos de uso |
| TW202525813A (zh) | 2019-12-19 | 2025-07-01 | 比利時商健生藥品公司 | 經取代之直鏈螺環接衍生物 |
| WO2024239282A1 (zh) * | 2023-05-24 | 2024-11-28 | 凌科药业(杭州)有限公司 | 一种药物组合物、外用制剂及其制备方法、应用 |
| CN120917009A (zh) * | 2024-01-26 | 2025-11-07 | 凌科药业(杭州)有限公司 | 一种吡唑基-氨基-嘧啶基衍生物的苯甲酰胺的晶型、制备方法及应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2280930C (en) | 1997-02-12 | 2010-04-06 | The Regents Of The University Of Michigan | Protein markers for lung cancer and use thereof |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| EP1054004B1 (en) * | 1997-12-15 | 2008-07-16 | Astellas Pharma Inc. | Novel pyrimidine-5-carboxamide derivatives |
| PT1154774E (pt) | 1999-02-10 | 2005-10-31 | Astrazeneca Ab | Derivados de quinazolina como inibidores de angiogenese |
| KR100881105B1 (ko) | 1999-11-05 | 2009-02-02 | 아스트라제네카 아베 | Ｖｅｇｆ 억제제로서의 퀴나졸린 유도체 |
| DE60037345T2 (de) | 1999-12-10 | 2008-11-13 | Pfizer Products Inc., Groton | Pyrrolo(2,3-d)pyrimidin-Verbindungen |
| JP3663382B2 (ja) | 2000-02-15 | 2005-06-22 | スージェン・インコーポレーテッド | ピロール置換２−インドリノン蛋白質キナーゼ阻害剤 |
| CN101218229A (zh) * | 2005-05-05 | 2008-07-09 | 阿斯利康(瑞典)有限公司 | 吡唑基-氨基取代的嘧啶及其在癌症治疗中的应用 |
| PL1891446T3 (pl) | 2005-06-14 | 2013-08-30 | Cellzome Gmbh | Sposób identyfikacji nowych związków oddziałujących z enzymami |
| GB0605691D0 (en) | 2006-03-21 | 2006-05-03 | Novartis Ag | Organic Compounds |
| ES2318616T3 (es) | 2006-06-01 | 2009-05-01 | Cellzome Ag | Metodos para la identificacion de moleculas que interactuan con zap-70 y para la purificacion de zap-70. |
| WO2008009458A1 (en) | 2006-07-21 | 2008-01-24 | Novartis Ag | 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors |
| BRPI0622030A2 (pt) | 2006-11-16 | 2014-04-22 | Pharmacopeia Llc | Derivados de purina 7-substituída, para imunossupressão |
| WO2008118822A1 (en) | 2007-03-23 | 2008-10-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US7834024B2 (en) | 2007-03-26 | 2010-11-16 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| CN101678215B (zh) | 2007-04-18 | 2014-10-01 | 辉瑞产品公司 | 用于治疗异常细胞生长的磺酰胺衍生物 |
| WO2008132502A1 (en) * | 2007-04-25 | 2008-11-06 | Astrazeneca Ab | Pyrazolyl-amino-substituted pyrimidines and their use for the treatment of cancer |
| US20090274698A1 (en) | 2007-07-06 | 2009-11-05 | Shripad Bhagwat | Combination anti-cancer therapy |
| CL2009001884A1 (es) | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| CA2758614A1 (en) | 2009-04-14 | 2010-10-21 | Cellzome Limited | Fluoro substituted pyrimidine compounds as jak3 inhibitors |
| CA2775009A1 (en) * | 2009-10-20 | 2011-04-28 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as jak inhibitors |
-
2012
- 2012-07-24 EP EP12738141.6A patent/EP2736901A1/en not_active Withdrawn
- 2012-07-24 US US14/234,662 patent/US20140179664A1/en not_active Abandoned
- 2012-07-24 WO PCT/EP2012/064515 patent/WO2013014162A1/en not_active Ceased
- 2012-07-24 BR BR112014000360A patent/BR112014000360A2/pt not_active IP Right Cessation
- 2012-07-24 KR KR1020147001951A patent/KR20140047092A/ko not_active Withdrawn
- 2012-07-24 AU AU2012288892A patent/AU2012288892B2/en not_active Expired - Fee Related
- 2012-07-24 CA CA2843195A patent/CA2843195A1/en not_active Abandoned
- 2012-07-24 JP JP2014522067A patent/JP2014521623A/ja active Pending
- 2012-07-24 CN CN201280043720.5A patent/CN103781780B/zh not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014521623A5 (https=) | ||
| JP2015500862A5 (https=) | ||
| JP2022534751A5 (https=) | ||
| JP2014531449A5 (https=) | ||
| RU2014130214A (ru) | Пиримидин-2, 4-диаминовые производные в качестве ингибиторов киназы | |
| JP2013508332A5 (https=) | ||
| RU2014152257A (ru) | Гетероциклильные пиримидиновые аналоги в качестве ингибиторов tyk2 | |
| JP2016538313A5 (https=) | ||
| RU2008135690A (ru) | Соединения и композиции в качестве ингибиторов протеинкиназы | |
| JP2014526549A5 (https=) | ||
| HRP20191220T1 (hr) | Disupstituirani oktahi-dropirolo[3,4-c]piroli kao modulatori oreksin receptora | |
| RU2015101115A (ru) | Гетероароматическое циклическое производное с алкильной разветвленной цепью | |
| RU2018120330A (ru) | Химерные соединения, осуществляющие нацеливание для протеолиза, и способы их получения и применения | |
| JP2019530695A5 (https=) | ||
| JP2017530999A5 (https=) | ||
| JP2007519754A5 (https=) | ||
| JP2022500402A5 (https=) | ||
| RU2007132262A (ru) | Соединения и композиции в качестве ингибиторов протеинкиназ | |
| JP2013531074A5 (https=) | ||
| SI3074386T1 (en) | New aminopyrimidine derivatives | |
| IL263511A (en) | 1h-pyrazolo[4,3-b]pyridines as pde1 inhibitors | |
| RU2015121374A (ru) | Ингибиторы alk-киназы | |
| JP2015517566A5 (https=) | ||
| SI2638031T1 (en) | Pyrazole aminopyrimidine derivatives as LRRK2 modulators | |
| RU2018138047A (ru) | Гетероциклические вещества - агонисты gpr119 |