JP2015500862A5 - - Google Patents
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- 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- Withdrawn
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- 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
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| EP2331532A1 (de) | 2008-09-03 | 2011-06-15 | 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. |
| US8394951B2 (en) | 2009-01-15 | 2013-03-12 | Rigel Pharmaceuticals Inc. | Protein kinase C inhibitors and uses thereof |
| WO2010118986A1 (en) | 2009-04-14 | 2010-10-21 | Cellzome Limited | Fluoro substituted pyrimidine compounds as jak3 inhibitors |
| WO2010129802A1 (en) | 2009-05-06 | 2010-11-11 | Portola Pharmaceuticals, Inc. | Inhibitors of jak |
| US20120172384A1 (en) * | 2009-06-18 | 2012-07-05 | Mihiro Sunose | Heterocyclylaminopyrimidines as kinase inhibitors |
| EP2475648A1 (en) | 2009-09-11 | 2012-07-18 | Cellzome Limited | Ortho substituted pyrimidine compounds as jak inhibitors |
| KR20120102601A (ko) | 2009-10-20 | 2012-09-18 | 셀좀 리미티드 | Ｊａｋ 저해제로서의 헤테로시클릴 피라졸로피리미딘 유사체 |
| JP2013525392A (ja) | 2010-04-30 | 2013-06-20 | セルゾーム リミティッド | Ｊａｋ阻害剤としてのピラゾール化合物 |
| US20130143915A1 (en) | 2010-07-01 | 2013-06-06 | 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 EP EP12806057.1A patent/EP2794598A1/en not_active Withdrawn
- 2012-12-20 AU AU2012357038A patent/AU2012357038B2/en not_active Expired - Fee Related
- 2012-12-20 RU RU2014130214A patent/RU2014130214A/ru not_active Application Discontinuation
- 2012-12-20 KR KR1020147016971A patent/KR20140114344A/ko not_active Withdrawn
- 2012-12-20 CA CA2860095A patent/CA2860095A1/en not_active Abandoned
- 2012-12-20 WO PCT/EP2012/076371 patent/WO2013092854A1/en not_active Ceased
- 2012-12-20 US US14/367,958 patent/US20150005281A1/en not_active Abandoned
- 2012-12-20 CN CN201280070527.0A patent/CN104169272A/zh active Pending
- 2012-12-20 JP JP2014548012A patent/JP2015500862A/ja not_active Withdrawn
- 2012-12-20 BR BR112014015723A patent/BR112014015723A8/pt not_active IP Right Cessation
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