JP2015500862A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015500862A5 JP2015500862A5 JP2014548012A JP2014548012A JP2015500862A5 JP 2015500862 A5 JP2015500862 A5 JP 2015500862A5 JP 2014548012 A JP2014548012 A JP 2014548012A JP 2014548012 A JP2014548012 A JP 2014548012A JP 2015500862 A5 JP2015500862 A5 JP 2015500862A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- pyrazol
- chloro
- pyrrolidin
- 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.)
- Withdrawn
Links
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 230000000155 isotopic effect Effects 0.000 claims 6
- -1 1-methyl-1H-pyrazol-4-yl Chemical group 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- CDVJKQIIUPKHAL-CYBMUJFWSA-N (2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]-n-cyclopropylpyrrolidine-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)NC2CC2)=N1 CDVJKQIIUPKHAL-CYBMUJFWSA-N 0.000 claims 1
- ONIJLSBDIIRAFS-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl ONIJLSBDIIRAFS-CYBMUJFWSA-N 0.000 claims 1
- PSVYKMBUIKACRQ-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCCC2)C(=O)C=C)=N1 PSVYKMBUIKACRQ-CYBMUJFWSA-N 0.000 claims 1
- ANCXLJLCQQIKKP-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl ANCXLJLCQQIKKP-CYBMUJFWSA-N 0.000 claims 1
- QZCQRTWGRNBEDH-LLVKDONJSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)CO)=N1 QZCQRTWGRNBEDH-LLVKDONJSA-N 0.000 claims 1
- HKVIEWIXNYVQSS-GFCCVEGCSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl HKVIEWIXNYVQSS-GFCCVEGCSA-N 0.000 claims 1
- ZOPYHDHDONFLRQ-GFCCVEGCSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)C=C)=N1 ZOPYHDHDONFLRQ-GFCCVEGCSA-N 0.000 claims 1
- KFULROJDRYWQNS-CQSZACIVSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl KFULROJDRYWQNS-CQSZACIVSA-N 0.000 claims 1
- DEAIETUFAWQIJP-CQSZACIVSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCCC2)C(=O)C=C)=N1 DEAIETUFAWQIJP-CQSZACIVSA-N 0.000 claims 1
- ZDVMTKYERGFKSH-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl ZDVMTKYERGFKSH-CYBMUJFWSA-N 0.000 claims 1
- CPJRKQDKFMIEGI-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)C=C)=N1 CPJRKQDKFMIEGI-CYBMUJFWSA-N 0.000 claims 1
- ONIJLSBDIIRAFS-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl ONIJLSBDIIRAFS-ZDUSSCGKSA-N 0.000 claims 1
- PSVYKMBUIKACRQ-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCCC2)C(=O)C=C)=N1 PSVYKMBUIKACRQ-ZDUSSCGKSA-N 0.000 claims 1
- HKVIEWIXNYVQSS-LBPRGKRZSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl HKVIEWIXNYVQSS-LBPRGKRZSA-N 0.000 claims 1
- ZOPYHDHDONFLRQ-LBPRGKRZSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)C(=O)C=C)=N1 ZOPYHDHDONFLRQ-LBPRGKRZSA-N 0.000 claims 1
- KFULROJDRYWQNS-AWEZNQCLSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl KFULROJDRYWQNS-AWEZNQCLSA-N 0.000 claims 1
- DEAIETUFAWQIJP-AWEZNQCLSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCCC2)C(=O)C=C)=N1 DEAIETUFAWQIJP-AWEZNQCLSA-N 0.000 claims 1
- ZDVMTKYERGFKSH-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl ZDVMTKYERGFKSH-ZDUSSCGKSA-N 0.000 claims 1
- CPJRKQDKFMIEGI-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)C(=O)C=C)=N1 CPJRKQDKFMIEGI-ZDUSSCGKSA-N 0.000 claims 1
- UYUBGNTYPRFJIZ-GFCCVEGCSA-N 1-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1N(C(=O)CN(C)C)CC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl UYUBGNTYPRFJIZ-GFCCVEGCSA-N 0.000 claims 1
- XLDJUSNJZDOQHI-LLVKDONJSA-N 1-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl XLDJUSNJZDOQHI-LLVKDONJSA-N 0.000 claims 1
- XYFZTXIUUMNXCR-LLVKDONJSA-N 1-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)C(=O)C=C)=N1 XYFZTXIUUMNXCR-LLVKDONJSA-N 0.000 claims 1
- OEURTTGUJDNBDQ-GFCCVEGCSA-N 1-[(3r)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl OEURTTGUJDNBDQ-GFCCVEGCSA-N 0.000 claims 1
- RPMAACYUOMABIE-GFCCVEGCSA-N 1-[(3r)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)C(=O)C=C)=N1 RPMAACYUOMABIE-GFCCVEGCSA-N 0.000 claims 1
- XLDJUSNJZDOQHI-NSHDSACASA-N 1-[(3s)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl XLDJUSNJZDOQHI-NSHDSACASA-N 0.000 claims 1
- OEURTTGUJDNBDQ-LBPRGKRZSA-N 1-[(3s)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl OEURTTGUJDNBDQ-LBPRGKRZSA-N 0.000 claims 1
- RPMAACYUOMABIE-LBPRGKRZSA-N 1-[(3s)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CC2)C(=O)C=C)=N1 RPMAACYUOMABIE-LBPRGKRZSA-N 0.000 claims 1
- DFZBGSUDSUAWFV-UHFFFAOYSA-N 1-[3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]azetidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl DFZBGSUDSUAWFV-UHFFFAOYSA-N 0.000 claims 1
- XYFZTXIUUMNXCR-UHFFFAOYSA-N 1-[3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NCC2CN(CC2)C(=O)C=C)=N1 XYFZTXIUUMNXCR-UHFFFAOYSA-N 0.000 claims 1
- ICTNRLPCFQGQLY-UHFFFAOYSA-N 1-[3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]azetidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl ICTNRLPCFQGQLY-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
- CEVFPLQCSHTYJP-GFCCVEGCSA-N 2-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]acetonitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CC#N)=N1 CEVFPLQCSHTYJP-GFCCVEGCSA-N 0.000 claims 1
- DMOWEXUSLBOCCO-GFCCVEGCSA-N 2-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCO)=N1 DMOWEXUSLBOCCO-GFCCVEGCSA-N 0.000 claims 1
- WIAHVYCQTMEZOK-JSGCOSHPSA-N 2-[(2s,4s)-4-fluoro-2-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]acetonitrile Chemical compound N1=C(NC[C@H]2N(C[C@@H](F)C2)CC#N)C(C)=CN=C1NC=1C=NN(C)C=1 WIAHVYCQTMEZOK-JSGCOSHPSA-N 0.000 claims 1
- FGMDDPURZPCLLZ-LLVKDONJSA-N 2-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CCO)CC2)=N1 FGMDDPURZPCLLZ-LLVKDONJSA-N 0.000 claims 1
- CRVJQCHRRILZRL-MRXNPFEDSA-N 2-[4-[[4-[[(2r)-1-(2-cyanoacetyl)pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-propan-2-ylacetamide Chemical compound C1=NN(CC(=O)NC(C)C)C=C1NC1=NC=CC(NC[C@@H]2N(CCC2)C(=O)CC#N)=N1 CRVJQCHRRILZRL-MRXNPFEDSA-N 0.000 claims 1
- FDCYHHXXQFBQPQ-QGZVFWFLSA-N 2-[4-[[4-[[(2r)-1-(2-cyanoethyl)pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-propan-2-ylacetamide Chemical compound C1=NN(CC(=O)NC(C)C)C=C1NC1=NC=CC(NC[C@@H]2N(CCC2)CCC#N)=N1 FDCYHHXXQFBQPQ-QGZVFWFLSA-N 0.000 claims 1
- PCIBCIDUZFCAMU-QGZVFWFLSA-N 2-[4-[[4-[[(2r)-1-(3-cyanopropanoyl)pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-propan-2-ylacetamide Chemical compound C1=NN(CC(=O)NC(C)C)C=C1NC1=NC=CC(NC[C@@H]2N(CCC2)C(=O)CCC#N)=N1 PCIBCIDUZFCAMU-QGZVFWFLSA-N 0.000 claims 1
- UHMQNIBBVBVAHP-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[(1-methylsulfonylazetidin-3-yl)methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1N(S(=O)(=O)C)CC1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl UHMQNIBBVBVAHP-UHFFFAOYSA-N 0.000 claims 1
- BLZSSTQQSKUJMF-CYBMUJFWSA-N 2-[4-[[5-chloro-4-[[(2r)-1-methylsulfonylpiperidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound CS(=O)(=O)N1CCCC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl BLZSSTQQSKUJMF-CYBMUJFWSA-N 0.000 claims 1
- LCQBOLJGWYQSNW-CYBMUJFWSA-N 2-[4-[[5-chloro-4-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methylamino]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(NC[C@@H]2N(CCC2)S(C)(=O)=O)=N1 LCQBOLJGWYQSNW-CYBMUJFWSA-N 0.000 claims 1
- UVLYRUPRPSIXDD-GFCCVEGCSA-N 2-[4-[[5-chloro-4-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)S(C)(=O)=O)=N1 UVLYRUPRPSIXDD-GFCCVEGCSA-N 0.000 claims 1
- GJTGYIXHOHUOCY-GFCCVEGCSA-N 2-[4-[[5-chloro-4-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound CS(=O)(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl GJTGYIXHOHUOCY-GFCCVEGCSA-N 0.000 claims 1
- LYGUHFBRHCGVQV-LLVKDONJSA-N 2-[4-[[5-chloro-4-[[(2r)-pyrrolidin-2-yl]methylamino]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(NC[C@@H]2NCCC2)=N1 LYGUHFBRHCGVQV-LLVKDONJSA-N 0.000 claims 1
- ZFEULNSJXLXHJH-SNVBAGLBSA-N 2-[4-[[5-chloro-4-[[(2r)-pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC[C@@H]2NCCC2)=N1 ZFEULNSJXLXHJH-SNVBAGLBSA-N 0.000 claims 1
- IYXHWXLYRYKBEB-ZDUSSCGKSA-N 2-[4-[[5-chloro-4-[[(2s)-1-ethenylsulfonylpyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)S(=O)(=O)C=C)=N1 IYXHWXLYRYKBEB-ZDUSSCGKSA-N 0.000 claims 1
- BLZSSTQQSKUJMF-ZDUSSCGKSA-N 2-[4-[[5-chloro-4-[[(2s)-1-methylsulfonylpiperidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound CS(=O)(=O)N1CCCC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl BLZSSTQQSKUJMF-ZDUSSCGKSA-N 0.000 claims 1
- LCQBOLJGWYQSNW-ZDUSSCGKSA-N 2-[4-[[5-chloro-4-[[(2s)-1-methylsulfonylpyrrolidin-2-yl]methylamino]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(NC[C@H]2N(CCC2)S(C)(=O)=O)=N1 LCQBOLJGWYQSNW-ZDUSSCGKSA-N 0.000 claims 1
- GJTGYIXHOHUOCY-LBPRGKRZSA-N 2-[4-[[5-chloro-4-[[(2s)-1-methylsulfonylpyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound CS(=O)(=O)N1CCC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl GJTGYIXHOHUOCY-LBPRGKRZSA-N 0.000 claims 1
- LYGUHFBRHCGVQV-NSHDSACASA-N 2-[4-[[5-chloro-4-[[(2s)-pyrrolidin-2-yl]methylamino]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(NC[C@H]2NCCC2)=N1 LYGUHFBRHCGVQV-NSHDSACASA-N 0.000 claims 1
- ZFEULNSJXLXHJH-JTQLQIEISA-N 2-[4-[[5-chloro-4-[[(2s)-pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC[C@H]2NCCC2)=N1 ZFEULNSJXLXHJH-JTQLQIEISA-N 0.000 claims 1
- CVDXEQFVQUDTGS-LLVKDONJSA-N 2-[4-[[5-chloro-4-[[(3r)-1-methylsulfonylpyrrolidin-3-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1N(S(=O)(=O)C)CC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl CVDXEQFVQUDTGS-LLVKDONJSA-N 0.000 claims 1
- OFYGBRWUMAUGIT-JTQLQIEISA-N 2-[4-[[5-chloro-4-[[(3s)-pyrrolidin-3-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CNCC2)=N1 OFYGBRWUMAUGIT-JTQLQIEISA-N 0.000 claims 1
- XSJQYKVQFGUVAS-OAHLLOKOSA-N 2-n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-5-methyl-4-n-[[(2r)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@@H]2N(CCC2)CCS(C)(=O)=O)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 XSJQYKVQFGUVAS-OAHLLOKOSA-N 0.000 claims 1
- XSJQYKVQFGUVAS-HNNXBMFYSA-N 2-n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-5-methyl-4-n-[[(2s)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@H]2N(CCC2)CCS(C)(=O)=O)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 XSJQYKVQFGUVAS-HNNXBMFYSA-N 0.000 claims 1
- SXIAJLYTRNHUQT-CQSZACIVSA-N 2-n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-5-methyl-4-n-[[(3r)-1-(2-methylsulfonylethyl)pyrrolidin-3-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@@H]2CN(CCS(C)(=O)=O)CC2)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 SXIAJLYTRNHUQT-CQSZACIVSA-N 0.000 claims 1
- GCHHFXPKDXUPTF-CYBMUJFWSA-N 3-[(2r)-2-[[[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=CC(NC[C@@H]2N(CCC2)C(=O)CC#N)=N1 GCHHFXPKDXUPTF-CYBMUJFWSA-N 0.000 claims 1
- NVTXATTVUFRHDG-CQSZACIVSA-N 3-[(2r)-2-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound N1=C(NC[C@@H]2N(CCC2)C(=O)CC#N)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 NVTXATTVUFRHDG-CQSZACIVSA-N 0.000 claims 1
- HJJHAJDOJOFIDR-GFCCVEGCSA-N 3-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)CC#N)=N1 HJJHAJDOJOFIDR-GFCCVEGCSA-N 0.000 claims 1
- VLTFEEKKKFCFID-CYBMUJFWSA-N 3-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCC#N)=N1 VLTFEEKKKFCFID-CYBMUJFWSA-N 0.000 claims 1
- VDXQFJGXOHKOPM-GFCCVEGCSA-N 3-[(2r)-2-[[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@@H]2N(CCC2)C(=O)CC#N)=N1 VDXQFJGXOHKOPM-GFCCVEGCSA-N 0.000 claims 1
- BXLMDRVGSAVAJL-CYBMUJFWSA-N 3-[(2r)-2-[[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@@H]2N(CCC2)CCC#N)=N1 BXLMDRVGSAVAJL-CYBMUJFWSA-N 0.000 claims 1
- JBDQWCFXWFAOST-OAHLLOKOSA-N 3-[(2r)-2-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound N1=C(NC[C@@H]2N(CCC2)CCC#N)C(C)=CN=C1NC=1C=NN(C)C=1 JBDQWCFXWFAOST-OAHLLOKOSA-N 0.000 claims 1
- NVTXATTVUFRHDG-AWEZNQCLSA-N 3-[(2s)-2-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound N1=C(NC[C@H]2N(CCC2)C(=O)CC#N)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 NVTXATTVUFRHDG-AWEZNQCLSA-N 0.000 claims 1
- VLTFEEKKKFCFID-ZDUSSCGKSA-N 3-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)CCC#N)=N1 VLTFEEKKKFCFID-ZDUSSCGKSA-N 0.000 claims 1
- JBDQWCFXWFAOST-HNNXBMFYSA-N 3-[(2s)-2-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound N1=C(NC[C@H]2N(CCC2)CCC#N)C(C)=CN=C1NC=1C=NN(C)C=1 JBDQWCFXWFAOST-HNNXBMFYSA-N 0.000 claims 1
- BDUSXEPDLAVSAU-ZFWWWQNUSA-N 3-[(2s,4s)-2-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]-4-fluoropyrrolidin-1-yl]propanenitrile Chemical compound N1=C(NC[C@H]2N(C[C@@H](F)C2)CCC#N)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 BDUSXEPDLAVSAU-ZFWWWQNUSA-N 0.000 claims 1
- VMFJTXRWSVCQEQ-AAEUAGOBSA-N 3-[(2s,4s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]-4-fluoropyrrolidin-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(C[C@@H](F)C2)CCC#N)=N1 VMFJTXRWSVCQEQ-AAEUAGOBSA-N 0.000 claims 1
- WCCYJKBFKFMOBU-JSGCOSHPSA-N 3-[(2s,4s)-4-fluoro-2-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound N1=C(NC[C@H]2N(C[C@@H](F)C2)C(=O)CC#N)C(C)=CN=C1NC=1C=NN(C)C=1 WCCYJKBFKFMOBU-JSGCOSHPSA-N 0.000 claims 1
- YSGRIPIKVJJGGG-ZFWWWQNUSA-N 3-[(2s,4s)-4-fluoro-2-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound N1=C(NC[C@H]2N(C[C@@H](F)C2)CCC#N)C(C)=CN=C1NC=1C=NN(C)C=1 YSGRIPIKVJJGGG-ZFWWWQNUSA-N 0.000 claims 1
- BVTINCWPBKTKQU-CYBMUJFWSA-N 3-[(3r)-3-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound N1=C(NC[C@@H]2CN(CC2)C(=O)CC#N)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 BVTINCWPBKTKQU-CYBMUJFWSA-N 0.000 claims 1
- OJTYOPYBLHOXQT-CQSZACIVSA-N 3-[(3r)-3-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound N1=C(NC[C@@H]2CN(CCC#N)CC2)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 OJTYOPYBLHOXQT-CQSZACIVSA-N 0.000 claims 1
- JNQPITDCLYXADA-GFCCVEGCSA-N 3-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CCC2)C(=O)CC#N)=N1 JNQPITDCLYXADA-GFCCVEGCSA-N 0.000 claims 1
- TXPQJNJHLCDOAO-LLVKDONJSA-N 3-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)C(=O)CC#N)=N1 TXPQJNJHLCDOAO-LLVKDONJSA-N 0.000 claims 1
- PTWZBUZNJRYTNH-GFCCVEGCSA-N 3-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CCC#N)CC2)=N1 PTWZBUZNJRYTNH-GFCCVEGCSA-N 0.000 claims 1
- JNQPITDCLYXADA-LBPRGKRZSA-N 3-[(3s)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CCC2)C(=O)CC#N)=N1 JNQPITDCLYXADA-LBPRGKRZSA-N 0.000 claims 1
- JXHFWIPQLNIHJB-CQSZACIVSA-N 4-[(2r)-2-[[[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=CC(NC[C@@H]2N(CCC2)C(=O)CCC#N)=N1 JXHFWIPQLNIHJB-CQSZACIVSA-N 0.000 claims 1
- DZIUKYGIWUMGAM-CYBMUJFWSA-N 4-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)CCC#N)=N1 DZIUKYGIWUMGAM-CYBMUJFWSA-N 0.000 claims 1
- GYGILBKXVXGSGU-CQSZACIVSA-N 4-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]butanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCCC#N)=N1 GYGILBKXVXGSGU-CQSZACIVSA-N 0.000 claims 1
- DFKJIZYFGAWBRM-CYBMUJFWSA-N 4-[(2r)-2-[[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@@H]2N(CCC2)C(=O)CCC#N)=N1 DFKJIZYFGAWBRM-CYBMUJFWSA-N 0.000 claims 1
- OLZJIYAMLRJTAV-HNNXBMFYSA-N 4-[(2s)-2-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound N1=C(NC[C@H]2N(CCC2)C(=O)CCC#N)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 OLZJIYAMLRJTAV-HNNXBMFYSA-N 0.000 claims 1
- DZIUKYGIWUMGAM-ZDUSSCGKSA-N 4-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)C(=O)CCC#N)=N1 DZIUKYGIWUMGAM-ZDUSSCGKSA-N 0.000 claims 1
- BQYIONVWZNHTBE-ZFWWWQNUSA-N 4-[(2s,4s)-2-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]-4-fluoropyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound N1=C(NC[C@H]2N(C[C@@H](F)C2)C(=O)CCC#N)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 BQYIONVWZNHTBE-ZFWWWQNUSA-N 0.000 claims 1
- KTUNBEMZVSRULS-AAEUAGOBSA-N 4-[(2s,4s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]-4-fluoropyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(C[C@@H](F)C2)C(=O)CCC#N)=N1 KTUNBEMZVSRULS-AAEUAGOBSA-N 0.000 claims 1
- XDRHOASLJJITGJ-JSGCOSHPSA-N 4-[(2s,4s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]-4-fluoropyrrolidin-1-yl]butanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(C[C@@H](F)C2)CCCC#N)=N1 XDRHOASLJJITGJ-JSGCOSHPSA-N 0.000 claims 1
- MKUSAHNLXGHAJL-ZFWWWQNUSA-N 4-[(2s,4s)-4-fluoro-2-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound N1=C(NC[C@H]2N(C[C@@H](F)C2)C(=O)CCC#N)C(C)=CN=C1NC=1C=NN(C)C=1 MKUSAHNLXGHAJL-ZFWWWQNUSA-N 0.000 claims 1
- RGJOHYDFTARWQG-CQSZACIVSA-N 4-[(3r)-3-[[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound N1=C(NC[C@@H]2CN(CC2)C(=O)CCC#N)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 RGJOHYDFTARWQG-CQSZACIVSA-N 0.000 claims 1
- ATUIJWDDPFPFBJ-CYBMUJFWSA-N 4-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]-4-oxobutanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CCC2)C(=O)CCC#N)=N1 ATUIJWDDPFPFBJ-CYBMUJFWSA-N 0.000 claims 1
- LCIJVJPULYFCQL-CQSZACIVSA-N 4-[(3r)-3-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-4-oxobutanenitrile Chemical compound N1=C(NC[C@@H]2CN(CC2)C(=O)CCC#N)C(C)=CN=C1NC=1C=NN(C)C=1 LCIJVJPULYFCQL-CQSZACIVSA-N 0.000 claims 1
- ATUIJWDDPFPFBJ-ZDUSSCGKSA-N 4-[(3s)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]-4-oxobutanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CCC2)C(=O)CCC#N)=N1 ATUIJWDDPFPFBJ-ZDUSSCGKSA-N 0.000 claims 1
- SQCGRQFNIAKQOV-GZJFXKPMSA-N 4-[[(2S,4S)-4-fluoro-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]-5-methyl-2-N-(1-methylpyrazol-4-yl)-1H-pyrimidine-2,4-diamine Chemical compound F[C@H]1C[C@@H](N(C1)CCS(=O)(=O)C)CC1(NC(=NC=C1C)NC=1C=NN(C1)C)N SQCGRQFNIAKQOV-GZJFXKPMSA-N 0.000 claims 1
- AWVBACACGWGWFA-UHFFFAOYSA-N 5-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]-1-methylpyrrolidin-2-one Chemical compound C1CC(=O)N(C)C1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl AWVBACACGWGWFA-UHFFFAOYSA-N 0.000 claims 1
- ZKVOZWYQEAXVMD-UHFFFAOYSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-(oxan-4-ylmethyl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NCC2CCOCC2)=N1 ZKVOZWYQEAXVMD-UHFFFAOYSA-N 0.000 claims 1
- XSFJCGSXBDREEI-UHFFFAOYSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[(1-methylpyrrolidin-2-yl)methyl]pyrimidine-2,4-diamine Chemical compound CN1CCCC1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl XSFJCGSXBDREEI-UHFFFAOYSA-N 0.000 claims 1
- BCVYWCYHGNITQN-UHFFFAOYSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[(1-methylsulfonylazetidin-3-yl)methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NCC2CN(C2)S(C)(=O)=O)=N1 BCVYWCYHGNITQN-UHFFFAOYSA-N 0.000 claims 1
- IBYSVYWALJSGRO-CYBMUJFWSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCS(C)(=O)=O)=N1 IBYSVYWALJSGRO-CYBMUJFWSA-N 0.000 claims 1
- YVKFYNLRXUJIEG-OAHLLOKOSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-(2-propan-2-ylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound CC(C)S(=O)(=O)CCN1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl YVKFYNLRXUJIEG-OAHLLOKOSA-N 0.000 claims 1
- SDDGKBQZQSBMNT-GFCCVEGCSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-(3,3,3-trifluoropropyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCC(F)(F)F)=N1 SDDGKBQZQSBMNT-GFCCVEGCSA-N 0.000 claims 1
- RBWYEZZFKQLBRA-GFCCVEGCSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpiperidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCCC2)S(C)(=O)=O)=N1 RBWYEZZFKQLBRA-GFCCVEGCSA-N 0.000 claims 1
- NAZVEDNLWCJNBR-LLVKDONJSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)S(C)(=O)=O)=N1 NAZVEDNLWCJNBR-LLVKDONJSA-N 0.000 claims 1
- IBYSVYWALJSGRO-ZDUSSCGKSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)CCS(C)(=O)=O)=N1 IBYSVYWALJSGRO-ZDUSSCGKSA-N 0.000 claims 1
- FUWVFFRCXILPMB-AWEZNQCLSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-(3-methylsulfonylpropyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)CCCS(C)(=O)=O)=N1 FUWVFFRCXILPMB-AWEZNQCLSA-N 0.000 claims 1
- RBWYEZZFKQLBRA-LBPRGKRZSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-methylsulfonylpiperidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCCC2)S(C)(=O)=O)=N1 RBWYEZZFKQLBRA-LBPRGKRZSA-N 0.000 claims 1
- NAZVEDNLWCJNBR-NSHDSACASA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)S(C)(=O)=O)=N1 NAZVEDNLWCJNBR-NSHDSACASA-N 0.000 claims 1
- GEISHDPQNBSUQY-SNVBAGLBSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(3r)-1-methylsulfonylpyrrolidin-3-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)S(C)(=O)=O)=N1 GEISHDPQNBSUQY-SNVBAGLBSA-N 0.000 claims 1
- GEISHDPQNBSUQY-JTQLQIEISA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(3s)-1-methylsulfonylpyrrolidin-3-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CC2)S(C)(=O)=O)=N1 GEISHDPQNBSUQY-JTQLQIEISA-N 0.000 claims 1
- MFJWJVUJAHGIMX-UHFFFAOYSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[4-(2-methylsulfonylethyl)morpholin-3-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NCC2N(CCOC2)CCS(C)(=O)=O)=N1 MFJWJVUJAHGIMX-UHFFFAOYSA-N 0.000 claims 1
- UZLUCSQMWZBEMJ-UHFFFAOYSA-N 5-chloro-4-n-(cyclohexylmethyl)-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NCC2CCCCC2)=N1 UZLUCSQMWZBEMJ-UHFFFAOYSA-N 0.000 claims 1
- ULMWVMIIMOPDJM-KWCCSABGSA-N 5-chloro-4-n-[[(2r)-1-(1,1-dioxothiolan-3-yl)pyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C2CS(=O)(=O)CC2)=N1 ULMWVMIIMOPDJM-KWCCSABGSA-N 0.000 claims 1
- LRJXZRUNXCFTGA-GFCCVEGCSA-N 5-chloro-4-n-[[(2r)-1-cyclopropylsulfonylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)S(=O)(=O)C2CC2)=N1 LRJXZRUNXCFTGA-GFCCVEGCSA-N 0.000 claims 1
- GGMMCQYPOMJHSS-CYBMUJFWSA-N 5-chloro-4-n-[[(2r)-1-ethenylsulfonylpiperidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCCC2)S(=O)(=O)C=C)=N1 GGMMCQYPOMJHSS-CYBMUJFWSA-N 0.000 claims 1
- JJVILJFRZFPFTK-GFCCVEGCSA-N 5-chloro-4-n-[[(2r)-1-ethenylsulfonylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)S(=O)(=O)C=C)=N1 JJVILJFRZFPFTK-GFCCVEGCSA-N 0.000 claims 1
- QNKVNZUDWNEQOQ-GFCCVEGCSA-N 5-chloro-4-n-[[(2r)-1-ethylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound CCN1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl QNKVNZUDWNEQOQ-GFCCVEGCSA-N 0.000 claims 1
- BTGZDLTUAODHFW-GFCCVEGCSA-N 5-chloro-4-n-[[(2r)-1-ethylsulfonylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound CCS(=O)(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl BTGZDLTUAODHFW-GFCCVEGCSA-N 0.000 claims 1
- GGMMCQYPOMJHSS-ZDUSSCGKSA-N 5-chloro-4-n-[[(2s)-1-ethenylsulfonylpiperidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCCC2)S(=O)(=O)C=C)=N1 GGMMCQYPOMJHSS-ZDUSSCGKSA-N 0.000 claims 1
- JJVILJFRZFPFTK-LBPRGKRZSA-N 5-chloro-4-n-[[(2s)-1-ethenylsulfonylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)S(=O)(=O)C=C)=N1 JJVILJFRZFPFTK-LBPRGKRZSA-N 0.000 claims 1
- QNKVNZUDWNEQOQ-LBPRGKRZSA-N 5-chloro-4-n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound CCN1CCC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl QNKVNZUDWNEQOQ-LBPRGKRZSA-N 0.000 claims 1
- JXHCLEKLRIAQOG-JSGCOSHPSA-N 5-chloro-4-n-[[(2s,4s)-4-fluoro-1-(3-methylsulfonylpropyl)pyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(C[C@@H](F)C2)CCCS(C)(=O)=O)=N1 JXHCLEKLRIAQOG-JSGCOSHPSA-N 0.000 claims 1
- NPDSHYKPRROTSO-LLVKDONJSA-N 5-chloro-4-n-[[(3r)-1-ethenylsulfonylpyrrolidin-3-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)S(=O)(=O)C=C)=N1 NPDSHYKPRROTSO-LLVKDONJSA-N 0.000 claims 1
- NPDSHYKPRROTSO-NSHDSACASA-N 5-chloro-4-n-[[(3s)-1-ethenylsulfonylpyrrolidin-3-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CC2)S(=O)(=O)C=C)=N1 NPDSHYKPRROTSO-NSHDSACASA-N 0.000 claims 1
- TZLDKSUNDGKMCX-RFVHGSKJSA-N 5-fluoro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@@H]2N(CCC2)S(C)(=O)=O)=N1 TZLDKSUNDGKMCX-RFVHGSKJSA-N 0.000 claims 1
- DAATVZRKBFLUHN-SBSPUUFOSA-N 5-fluoro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@@H]2NCCC2)=N1 DAATVZRKBFLUHN-SBSPUUFOSA-N 0.000 claims 1
- DAATVZRKBFLUHN-FVGYRXGTSA-N 5-fluoro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@H]2NCCC2)=N1 DAATVZRKBFLUHN-FVGYRXGTSA-N 0.000 claims 1
- YTPSQOHQLAJLER-OAHLLOKOSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@@H]2N(CCC2)CCS(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 YTPSQOHQLAJLER-OAHLLOKOSA-N 0.000 claims 1
- PTXKOKBZWVETHC-CYBMUJFWSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@@H]2N(CCC2)S(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 PTXKOKBZWVETHC-CYBMUJFWSA-N 0.000 claims 1
- WBKRTQSFMUHMDY-RFVHGSKJSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.N1=C(NC[C@@H]2NCCC2)C(C)=CN=C1NC=1C=NN(C)C=1 WBKRTQSFMUHMDY-RFVHGSKJSA-N 0.000 claims 1
- YTPSQOHQLAJLER-HNNXBMFYSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@H]2N(CCC2)CCS(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 YTPSQOHQLAJLER-HNNXBMFYSA-N 0.000 claims 1
- PTXKOKBZWVETHC-ZDUSSCGKSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@H]2N(CCC2)S(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 PTXKOKBZWVETHC-ZDUSSCGKSA-N 0.000 claims 1
- WBKRTQSFMUHMDY-MERQFXBCSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.N1=C(NC[C@H]2NCCC2)C(C)=CN=C1NC=1C=NN(C)C=1 WBKRTQSFMUHMDY-MERQFXBCSA-N 0.000 claims 1
- SGSVAYRXUJLLAB-OAHLLOKOSA-N Cc1cnc(Nc2cnn(CC(F)F)c2)nc1NC[C@H]1CCCN1CCC#N Chemical compound Cc1cnc(Nc2cnn(CC(F)F)c2)nc1NC[C@H]1CCCN1CCC#N SGSVAYRXUJLLAB-OAHLLOKOSA-N 0.000 claims 1
- TZLDKSUNDGKMCX-MERQFXBCSA-N Cl.Cn1cc(Nc2ncc(F)c(NC[C@@H]3CCCN3S(C)(=O)=O)n2)cn1 Chemical compound Cl.Cn1cc(Nc2ncc(F)c(NC[C@@H]3CCCN3S(C)(=O)=O)n2)cn1 TZLDKSUNDGKMCX-MERQFXBCSA-N 0.000 claims 1
- XWAIHPHTWPDHKD-AAEUAGOBSA-N Cn1cc(Nc2ncc(Cl)c(NC[C@@H]3C[C@H](F)CN3CCS(C)(=O)=O)n2)cn1 Chemical compound Cn1cc(Nc2ncc(Cl)c(NC[C@@H]3C[C@H](F)CN3CCS(C)(=O)=O)n2)cn1 XWAIHPHTWPDHKD-AAEUAGOBSA-N 0.000 claims 1
- KTNJAVTYORZGMV-INHRHCAVSA-N FC(CN1N=CC(=C1)C1(NC=C(C(=N1)NC[C@H]1N(C[C@H](C1)F)CCS(=O)(=O)C)C)N)F Chemical compound FC(CN1N=CC(=C1)C1(NC=C(C(=N1)NC[C@H]1N(C[C@H](C1)F)CCS(=O)(=O)C)C)N)F KTNJAVTYORZGMV-INHRHCAVSA-N 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000030533 eye disease Diseases 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
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- OLGZNLFUXZSMAD-CYBMUJFWSA-N n-[2-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethyl]methanesulfonamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCNS(C)(=O)=O)=N1 OLGZNLFUXZSMAD-CYBMUJFWSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 0 **N(*)c1c(*)cnc(N*)n1 Chemical compound **N(*)c1c(*)cnc(N*)n1 0.000 description 4
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11195662 | 2011-12-23 | ||
| EP11195662.9 | 2011-12-23 | ||
| PCT/EP2012/076371 WO2013092854A1 (en) | 2011-12-23 | 2012-12-20 | Pyrimidine-2,4-diamine derivatives as kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015500862A JP2015500862A (ja) | 2015-01-08 |
| JP2015500862A5 true JP2015500862A5 (enExample) | 2016-02-18 |
Family
ID=47429836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014548012A Withdrawn JP2015500862A (ja) | 2011-12-23 | 2012-12-20 | キナーゼ阻害剤としてのピリミジン−２，４−ジアミン誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20150005281A1 (enExample) |
| EP (1) | EP2794598A1 (enExample) |
| JP (1) | JP2015500862A (enExample) |
| KR (1) | KR20140114344A (enExample) |
| CN (1) | CN104169272A (enExample) |
| AU (1) | AU2012357038B2 (enExample) |
| BR (1) | BR112014015723A8 (enExample) |
| CA (1) | CA2860095A1 (enExample) |
| RU (1) | RU2014130214A (enExample) |
| WO (1) | WO2013092854A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9296725B2 (en) * | 2012-05-24 | 2016-03-29 | Cellzome Limited | Heterocyclyl pyrimidine analogues as TYK2 inhibitors |
| AR094537A1 (es) * | 2013-11-07 | 2015-08-12 | Bristol Myers Squibb Co | COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA ÚTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL-23 Y/O IFNa |
| US9260415B2 (en) * | 2013-12-05 | 2016-02-16 | Genentech, Inc. | Heteroaryl pyridone and aza-pyridone compounds with electrophilic functionality |
| AR099376A1 (es) * | 2013-12-20 | 2016-07-20 | Signal Pharm Llc | Compuestos de diaminopirimidilo sustituidos, sus composiciones y métodos de tratamiento con aquellos |
| JP6517319B2 (ja) | 2014-03-28 | 2019-05-22 | キャリター・サイエンシーズ・リミテッド・ライアビリティ・カンパニーＣａｌｉｔｏｒ Ｓｃｉｅｎｃｅｓ， Ｌｌｃ | 置換されたヘテロアリール化合物および使用方法 |
| US10106507B2 (en) | 2014-08-03 | 2018-10-23 | H. Lee Moffitt Cancer Center and Research Insitute, Inc. | Potent dual BRD4-kinase inhibitors as cancer therapeutics |
| EP3347097B1 (en) | 2015-09-11 | 2021-02-24 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine derivatives as modulators of the kinases jak, flt3 and aurora |
| US10738016B2 (en) | 2015-10-13 | 2020-08-11 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | BRD4-kinase inhibitors as cancer therapeutics |
| CN113214230B (zh) * | 2017-09-21 | 2022-10-04 | 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 |
| WO2019057112A1 (zh) * | 2017-09-21 | 2019-03-28 | 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 |
| 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 |
| CN111718332B (zh) * | 2019-03-19 | 2021-08-17 | 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 |
| CN111004215B (zh) * | 2019-12-22 | 2022-08-09 | 华北理工大学 | 2,4-取代嘧啶类衍生物及其制备方法和在制备抗肿瘤药物中的应用 |
| WO2025166161A1 (en) * | 2024-02-02 | 2025-08-07 | Deciphera Pharmaceuticals, Llc | Ulk inhibitors and methods of use thereof |
| WO2025166124A1 (en) * | 2024-02-02 | 2025-08-07 | Deciphera Pharmaceuticals, Llc | Ulk inhibitors and methods of use thereof |
| CN120698987B (zh) * | 2025-06-20 | 2026-04-17 | 大连医科大学 | 2-芳氨基嘧啶类化合物及其应用 |
Family Cites Families (36)
| 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 |
| BRPI0017548B8 (pt) | 1999-02-10 | 2023-05-02 | Astrazeneca Ab | Composto |
| CN100376567C (zh) | 1999-11-05 | 2008-03-26 | 阿斯特拉曾尼卡有限公司 | 作为vegf抑制剂的喹唑啉衍生物 |
| EA006227B1 (ru) | 1999-12-10 | 2005-10-27 | Пфайзер Продактс Инк. | СОЕДИНЕНИЯ ПИРРОЛО[2,3-d]ПИРИМИДИНА |
| AR034118A1 (es) | 2000-02-15 | 2004-02-04 | Sugen Inc | Compuestos de 2-indolinonas sustituidas con pirroles inhibidoras de proteinquinasas; sus composiciones farmaceuticas e intermediarios de sintesis |
| US7109337B2 (en) | 2002-12-20 | 2006-09-19 | Pfizer Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| EA013248B1 (ru) | 2002-12-20 | 2010-04-30 | Пфайзер Продактс Инк. | Производные пиримидина для лечения патологического роста клеток |
| UA80767C2 (en) | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| ITMI20022758A1 (it) | 2002-12-23 | 2004-06-24 | Isagro Ricerca Srl | Nuovi uracili ad attivita' erbicida. |
| WO2005111022A1 (en) | 2004-05-14 | 2005-11-24 | Pfizer Products Inc. | Pyrimidines derivatives for the treatment of abnormal cell growth |
| WO2006134056A1 (en) | 2005-06-14 | 2006-12-21 | Cellzome Ag | Process for the identification of novel enzyme interacting compounds |
| RS20080272A (sr) | 2005-12-21 | 2009-07-15 | Pfizer Products Inc., | Derivati pirimidina za tretman neprirodnog rasta ćelija |
| 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. |
| EP2054392A2 (en) | 2006-06-15 | 2009-05-06 | Boehringer Ingelheim International GmbH | 2-anilino-4-(heterocyclic)amino-pyrimidines as inhibitors of protein kinase c-alpha |
| CA2657260A1 (en) | 2006-07-21 | 2008-01-24 | Novartis Ag | 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors |
| KR20100014271A (ko) | 2006-11-16 | 2010-02-10 | 파마코페이아, 엘엘씨. | 면역 억제를 위한 7-치환된 퓨린 유도체 |
| DE102007010801A1 (de) | 2007-03-02 | 2008-09-04 | Bayer Cropscience Ag | Diaminopyrimidine als Fungizide |
| US7947698B2 (en) | 2007-03-23 | 2011-05-24 | 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 |
| AP2009005010A0 (en) | 2007-04-18 | 2009-10-31 | Pfizer Prod Inc | Sulfonyl amide derivatives for the treatment of abnormal cell growth |
| JP2010532756A (ja) | 2007-07-06 | 2010-10-14 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | ｍＴＯＲＣ１及びｍＴＯＲＣ２の両方の阻害剤を含む組み合わせ抗癌療法 |
| JP5705720B2 (ja) | 2008-04-16 | 2015-04-22 | ポートラ ファーマシューティカルズ， インコーポレイテッド | Ｓｙｋまたはｊａｋキナーゼ阻害剤としての２，６−ジアミノ−ピリミジン−５−イル−カルボキサミド |
| WO2010025851A1 (de) * | 2008-09-03 | 2010-03-11 | Bayer Cropscience Ag | Thienylaminopyrimidine als fungizide |
| 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. |
| CA2749195C (en) | 2009-01-15 | 2017-03-07 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| US20120040955A1 (en) | 2009-04-14 | 2012-02-16 | Richard John Harrison | Fluoro substituted pyrimidine compounds as jak3 inhibitors |
| US8367689B2 (en) | 2009-05-06 | 2013-02-05 | Portola Pharmaceuticals, Inc. | Inhibitors of JAK |
| EP2443106A1 (en) * | 2009-06-18 | 2012-04-25 | Cellzome Limited | Heterocyclylaminopyrimidines as kinase inhibitors |
| EP2475648A1 (en) | 2009-09-11 | 2012-07-18 | Cellzome Limited | Ortho substituted pyrimidine compounds as jak inhibitors |
| NZ598907A (en) | 2009-10-20 | 2014-03-28 | Cellzome Ltd | Heterocyclyl pyrazolopyrimidine analogues as jak inhibitors |
| MX2012012328A (es) | 2010-04-30 | 2013-05-06 | Cellzome Ltd | Compuestos pirazol como inhibidores de jak. |
| EP2588105A1 (en) | 2010-07-01 | 2013-05-08 | Cellzome Limited | Triazolopyridines as tyk2 inhibitors |
| WO2012022681A2 (en) | 2010-08-20 | 2012-02-23 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as selective jak inhibitors |
| EP2638018A1 (en) | 2010-11-09 | 2013-09-18 | Cellzome Limited | Pyridine compounds and aza analogues thereof as tyk2 inhibitors |
-
2012
- 2012-12-20 WO PCT/EP2012/076371 patent/WO2013092854A1/en not_active Ceased
- 2012-12-20 CN CN201280070527.0A patent/CN104169272A/zh active Pending
- 2012-12-20 AU AU2012357038A patent/AU2012357038B2/en not_active Expired - Fee Related
- 2012-12-20 BR BR112014015723A patent/BR112014015723A8/pt not_active IP Right Cessation
- 2012-12-20 EP EP12806057.1A patent/EP2794598A1/en not_active Withdrawn
- 2012-12-20 RU RU2014130214A patent/RU2014130214A/ru not_active Application Discontinuation
- 2012-12-20 JP JP2014548012A patent/JP2015500862A/ja not_active Withdrawn
- 2012-12-20 CA CA2860095A patent/CA2860095A1/en not_active Abandoned
- 2012-12-20 US US14/367,958 patent/US20150005281A1/en not_active Abandoned
- 2012-12-20 KR KR1020147016971A patent/KR20140114344A/ko not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2014130214A (ru) | Пиримидин-2, 4-диаминовые производные в качестве ингибиторов киназы | |
| JP2014521623A5 (enExample) | ||
| CA2671744A1 (en) | Compounds and compositions as protein kinase inhibitors | |
| SI3074386T1 (en) | New aminopyrimidine derivatives | |
| JP2012501312A5 (enExample) | ||
| AU2010286569B2 (en) | Compounds and compositions as protein kinase inhibitors | |
| JP2017510555A5 (enExample) | ||
| JP2023509260A5 (enExample) | ||
| AU2016314898B2 (en) | 2,4-bis(nitrogen-containing group)-substituted pyrimidine compound, preparation method and use thereof | |
| JP2020073561A5 (enExample) | ||
| RU2433128C2 (ru) | Новые пиримидиновые производные и их применение в терапии, а также применение пиримидиновых производных в изготовлении лекарственного средства для предупреждения и/или лечения болезни альцгеймера | |
| RU2386630C2 (ru) | Соединения и композиции в качестве ингибиторов протеинтирозинкиназы | |
| JP2017530999A5 (enExample) | ||
| JP2017510554A5 (enExample) | ||
| HRP20231310T1 (hr) | Heteroarilaminopirimidin amidni inhibitori autofagije i postupci njihove primjene | |
| RU2014152257A (ru) | Гетероциклильные пиримидиновые аналоги в качестве ингибиторов tyk2 | |
| JP2017506659A5 (enExample) | ||
| RU2013155456A (ru) | Соединения пирролидинилмочевины и пирролидинилтиомочевины как ингибиторы киназы trka | |
| HRP20110882T1 (hr) | Ciklopenta [d] pirimidini kao inhibitori kinaze akt proteina | |
| JP2014526549A5 (enExample) | ||
| JP2013510876A5 (enExample) | ||
| RU2016136116A (ru) | Фармацевтические соединения | |
| HRP20172006T1 (hr) | Derivati pirazol-aminopiridina kao lrrk2-modulatori | |
| JP2009513575A5 (enExample) | ||
| SI2790705T1 (en) | Use of activity inhibitors or PI3K function |