JP2015500862A5 - - Google Patents

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Publication number: JP2015500862A5
Authority: JP; Japan
Prior art keywords: methyl; amino; pyrazol; chloro; pyrrolidin
Prior art date: 2012-12-20
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

JP2014548012A

Other languages

English (en)

Japanese (ja)

Other versions

JP2015500862A (ja

Filing date

2012-12-20

Publication date

2016-02-18

2012-12-20 Application filed filed Critical

2012-12-20 Priority claimed from PCT/EP2012/076371 external-priority patent/WO2013092854A1/en

2015-01-08 Publication of JP2015500862A publication Critical patent/JP2015500862A/ja

2016-02-18 Publication of JP2015500862A5 publication Critical patent/JP2015500862A5/ja

Status Withdrawn legal-status Critical Current

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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
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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
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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

JP2014548012A 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 Withdrawn JP2015500862A (ja)

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2012
- 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 WO PCT/EP2012/076371 patent/WO2013092854A1/en not_active Ceased
- 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 EP EP12806057.1A patent/EP2794598A1/en not_active Withdrawn
- 2012-12-20 RU RU2014130214A patent/RU2014130214A/ru not_active Application Discontinuation
- 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 KR KR1020147016971A patent/KR20140114344A/ko not_active Withdrawn

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