JP2015500862A - 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 - Google Patents

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Publication number

JP2015500862A

JP2015500862A JP2014548012A JP2014548012A JP2015500862A JP 2015500862 A JP2015500862 A JP 2015500862A JP 2014548012 A JP2014548012 A JP 2014548012A JP 2014548012 A JP2014548012 A JP 2014548012A JP 2015500862 A JP2015500862 A JP 2015500862A

Authority

JP

Japan

Prior art keywords

methyl

amino

pyrazol

chloro

pyrrolidin

Prior art date

2011-12-23

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Withdrawn

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• YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title claims description 3
• 229940043355 kinase inhibitor Drugs 0.000 title description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 122
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 65
• 201000010099 disease Diseases 0.000 claims abstract description 37
• 239000003814 drug Substances 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 230000001363 autoimmune Effects 0.000 claims abstract description 12
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 12
• 230000000172 allergic effect Effects 0.000 claims abstract description 11
• 208000010668 atopic eczema Diseases 0.000 claims abstract description 11
• 230000002265 prevention Effects 0.000 claims abstract description 11
• 238000000034 method Methods 0.000 claims description 282
• -1 (3-(((5-chloro-2-((1- (2-hydroxyethyl) -1H-pyrazol-4-yl) amino) pyrimidin-4-yl) amino) methyl) pyrrolidine -1-yl) ethanone Chemical compound 0.000 claims description 85
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 55
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 150000002367 halogens Chemical class 0.000 claims description 32
• 208000035475 disorder Diseases 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 230000000155 isotopic effect Effects 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 206010052779 Transplant rejections Diseases 0.000 claims description 12
• 208000024908 graft versus host disease Diseases 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 230000002062 proliferating effect Effects 0.000 claims description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 10
• 208000037765 diseases and disorders Diseases 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 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 description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 150000004985 diamines Chemical class 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• XYFZTXIUUMNXCR-NSHDSACASA-N 1-[(3s)-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-NSHDSACASA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• BBOVBRAGQXRPAE-CQSZACIVSA-N 3-[(2r)-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(CCC2)C(=O)CC#N)C(C)=CN=C1NC=1C=NN(C)C=1 BBOVBRAGQXRPAE-CQSZACIVSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
• 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 description 3
• JNQPITDCLYXADA-UHFFFAOYSA-N 3-[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(NCC2CN(CCC2)C(=O)CC#N)=N1 JNQPITDCLYXADA-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• RBWYEZZFKQLBRA-GFCCVEGCSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpiperidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical class 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 description 3
• NAZVEDNLWCJNBR-LLVKDONJSA-N 5-chloro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical class 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 description 3
• 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 description 3
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