ES2860937T3 - Derivados de pirimidina-2,4-diamina para el tratamiento del cáncer - Google Patents

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Publication number

ES2860937T3

ES2860937T3 ES13859400T ES13859400T ES2860937T3 ES 2860937 T3 ES2860937 T3 ES 2860937T3 ES 13859400 T ES13859400 T ES 13859400T ES 13859400 T ES13859400 T ES 13859400T ES 2860937 T3 ES2860937 T3 ES 2860937T3

Authority

ES

Spain

Prior art keywords

amino

optionally substituted

substituents selected

dimethylphenyl

pyrimidin

Prior art date

2012-11-27

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.)

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• 206010028980 Neoplasm Diseases 0.000 title claims description 58
• 201000011510 cancer Diseases 0.000 title claims description 48
• YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title claims description 9
• 125000001424 substituent group Chemical group 0.000 claims abstract description 157
• 150000001875 compounds Chemical class 0.000 claims abstract description 112
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 84
• -1 benzothiophene-3-yl Chemical group 0.000 claims abstract description 61
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 57
• 125000003118 aryl group Chemical group 0.000 claims abstract description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 53
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 40
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 39
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 39
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 39
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 39
• 239000001301 oxygen Substances 0.000 claims abstract description 39
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 39
• 239000011593 sulfur Substances 0.000 claims abstract description 39
• 239000001257 hydrogen Substances 0.000 claims abstract description 37
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 24
• 150000002367 halogens Chemical class 0.000 claims abstract description 24
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 9
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
• 125000006707 (C3-C12) heterocycloalkyl group Chemical group 0.000 claims abstract description 6
• 229910052702 rhenium Inorganic materials 0.000 claims abstract description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 5
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims abstract description 5
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 4
• 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims abstract description 4
• 150000001721 carbon Chemical group 0.000 claims abstract description 4
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
• 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims abstract description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
• 229910052703 rhodium Inorganic materials 0.000 claims abstract description 3
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims abstract 2
• 101100024317 Caenorhabditis elegans mrt-2 gene Proteins 0.000 claims abstract 2
• 210000004027 cell Anatomy 0.000 claims description 42
• 208000009956 adenocarcinoma Diseases 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 238000011282 treatment Methods 0.000 claims description 18
• 206010025323 Lymphomas Diseases 0.000 claims description 15
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• 239000003814 drug Substances 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
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• 239000002671 adjuvant Substances 0.000 claims description 10
• 239000003085 diluting agent Substances 0.000 claims description 10
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• 201000010099 disease Diseases 0.000 claims description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
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• 206010016629 fibroma Diseases 0.000 claims description 6
• 201000011066 hemangioma Diseases 0.000 claims description 6
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 6
• 239000003112 inhibitor Substances 0.000 claims description 6
• 208000032612 Glial tumor Diseases 0.000 claims description 5
• 206010018338 Glioma Diseases 0.000 claims description 5
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
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• 208000006990 cholangiocarcinoma Diseases 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• 210000000813 small intestine Anatomy 0.000 claims description 5
• 229940124530 sulfonamide Drugs 0.000 claims description 5
• 201000003076 Angiosarcoma Diseases 0.000 claims description 4
• 208000002927 Hamartoma Diseases 0.000 claims description 4
• 208000001258 Hemangiosarcoma Diseases 0.000 claims description 4
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 4
• 208000018142 Leiomyosarcoma Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 208000008383 Wilms tumor Diseases 0.000 claims description 4
• 208000002458 carcinoid tumor Diseases 0.000 claims description 4
• 239000013066 combination product Substances 0.000 claims description 4
• 229940127555 combination product Drugs 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 4
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• 206010027191 meningioma Diseases 0.000 claims description 4
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• UDBCIVOBBNHZBB-UHFFFAOYSA-N 4-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CCNC1=CC(C=2C(=C(C)C=CC=2)C)=NC(N)=N1 UDBCIVOBBNHZBB-UHFFFAOYSA-N 0.000 claims description 3
• ZEFLVHVNLHLHCR-UHFFFAOYSA-N 4-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethyl]benzenesulfonamide Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=CC(=CC=3)S(N)(=O)=O)C=2)=C1C ZEFLVHVNLHLHCR-UHFFFAOYSA-N 0.000 claims description 3
• IJVXKKLPMOXPAK-UHFFFAOYSA-N 4-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethylamino]benzenesulfonamide Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3C=CC(=CC=3)S(N)(=O)=O)C=2)=C1C IJVXKKLPMOXPAK-UHFFFAOYSA-N 0.000 claims description 3
• SBPJEECEHKBUFA-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-[2-(4-methylsulfonylphenyl)ethyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=CC(=CC=3)S(C)(=O)=O)C=2)=C1C SBPJEECEHKBUFA-UHFFFAOYSA-N 0.000 claims description 3
• KNPKJKXHRLPUOR-UHFFFAOYSA-N 6-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethylamino]pyridine-3-sulfonamide Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3N=CC(=CC=3)S(N)(=O)=O)C=2)=C1C KNPKJKXHRLPUOR-UHFFFAOYSA-N 0.000 claims description 3
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 3
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 3
• 201000005262 Chondroma Diseases 0.000 claims description 3
• 208000017604 Hodgkin disease Diseases 0.000 claims description 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 3
• 208000009905 Neurofibromatoses Diseases 0.000 claims description 3
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 3
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 3
• 208000029742 colonic neoplasm Diseases 0.000 claims description 3
• 208000014018 liver neoplasm Diseases 0.000 claims description 3
• RRBPRUSNMMUFEZ-UHFFFAOYSA-N n-[3-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]-2,2-dimethylpropyl]-3-fluorobenzenesulfonamide Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCC(C)(C)CNS(=O)(=O)C=3C=C(F)C=CC=3)C=2)=C1C RRBPRUSNMMUFEZ-UHFFFAOYSA-N 0.000 claims description 3
• 201000004931 neurofibromatosis Diseases 0.000 claims description 3
• JGNBWIJALCHVHC-UHFFFAOYSA-N 1-[3-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]propyl]-3-(3,4-difluorophenyl)urea Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCCNC(=O)NC=3C=C(F)C(F)=CC=3)C=2)=C1C JGNBWIJALCHVHC-UHFFFAOYSA-N 0.000 claims description 2
• AVFWTKFZYQCRRY-UHFFFAOYSA-N 2-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethylamino]pyridine-4-carbonitrile Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3N=CC=C(C=3)C#N)C=2)=C1C AVFWTKFZYQCRRY-UHFFFAOYSA-N 0.000 claims description 2
• KARFXSDQQHHSRI-UHFFFAOYSA-N 3-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethyl]phenol Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=C(O)C=CC=3)C=2)=C1C KARFXSDQQHHSRI-UHFFFAOYSA-N 0.000 claims description 2
• DMWAFOPFUKYONK-UHFFFAOYSA-N 4-N-[2-(1,3-benzoxazol-2-ylamino)ethyl]-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine Chemical compound O1C(=NC2=C1C=CC=C2)NCCNC1=NC(=NC(=C1)C1=C(C(=CC=C1)C)C)N DMWAFOPFUKYONK-UHFFFAOYSA-N 0.000 claims description 2
• HFMIWXHUMHMCDK-UHFFFAOYSA-N 4-[2-[[2-amino-6-(2,3-dichlorophenyl)pyrimidin-4-yl]amino]ethyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CCNC1=CC(C=2C(=C(Cl)C=CC=2)Cl)=NC(N)=N1 HFMIWXHUMHMCDK-UHFFFAOYSA-N 0.000 claims description 2
• AGUNDECOORWBJD-UHFFFAOYSA-N 4-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethoxy]benzonitrile Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCOC=3C=CC(=CC=3)C#N)C=2)=C1C AGUNDECOORWBJD-UHFFFAOYSA-N 0.000 claims description 2
• RRGUKNZSUFJYFN-UHFFFAOYSA-N 4-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethyl]benzonitrile Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=CC(=CC=3)C#N)C=2)=C1C RRGUKNZSUFJYFN-UHFFFAOYSA-N 0.000 claims description 2
• ILDPJNPDSPDHPO-UHFFFAOYSA-N 4-[2-[[2-amino-6-(3-chloro-2-methylphenyl)pyrimidin-4-yl]amino]ethyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CCNC1=CC(C=2C(=C(Cl)C=CC=2)C)=NC(N)=N1 ILDPJNPDSPDHPO-UHFFFAOYSA-N 0.000 claims description 2
• MFMPEHREIZTPMN-UHFFFAOYSA-N 4-[2-[[2-amino-6-(3-cyano-2-methylphenyl)pyrimidin-4-yl]amino]ethyl]benzenesulfonamide Chemical compound CC1=C(C#N)C=CC=C1C1=CC(NCCC=2C=CC(=CC=2)S(N)(=O)=O)=NC(N)=N1 MFMPEHREIZTPMN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• REZWHWQJXYBDOX-UHFFFAOYSA-N 4-n-(2-anilinoethyl)-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3C=CC=CC=3)C=2)=C1C REZWHWQJXYBDOX-UHFFFAOYSA-N 0.000 claims description 2
• IWMGPNZZKICENO-UHFFFAOYSA-N 4-n-[2-(4-chlorophenyl)ethyl]-6-(1h-indol-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(C=2C=3C=CNC=3C=CC=2)=NC(N)=NC=1NCCC1=CC=C(Cl)C=C1 IWMGPNZZKICENO-UHFFFAOYSA-N 0.000 claims description 2
• YTJCNLRMJOGDSE-UHFFFAOYSA-N 4-n-[2-(4-chlorophenyl)ethyl]-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=CC(Cl)=CC=3)C=2)=C1C YTJCNLRMJOGDSE-UHFFFAOYSA-N 0.000 claims description 2
• NZOLVOAJUXQZFR-UHFFFAOYSA-N 4-n-[2-(benzenesulfonyl)ethyl]-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCS(=O)(=O)C=3C=CC=CC=3)C=2)=C1C NZOLVOAJUXQZFR-UHFFFAOYSA-N 0.000 claims description 2
• MIRNPMNMQDJJAO-UHFFFAOYSA-N 4-n-[2-[(3-bromo-1,2,4-thiadiazol-5-yl)amino]ethyl]-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3SN=C(Br)N=3)C=2)=C1C MIRNPMNMQDJJAO-UHFFFAOYSA-N 0.000 claims description 2
• KVUMCYIVBZKKSM-UHFFFAOYSA-N 4-n-[2-[(5-bromopyridin-2-yl)amino]ethyl]-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3N=CC(Br)=CC=3)C=2)=C1C KVUMCYIVBZKKSM-UHFFFAOYSA-N 0.000 claims description 2
• YZPMNXSCGKCRNC-UHFFFAOYSA-N 4-n-[3-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]propyl]benzene-1,4-disulfonamide Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCCNS(=O)(=O)C=3C=CC(=CC=3)S(N)(=O)=O)C=2)=C1C YZPMNXSCGKCRNC-UHFFFAOYSA-N 0.000 claims description 2
• SQZATOYDHDHTTA-UHFFFAOYSA-N 6-(2,3-dichlorophenyl)-4-n-[2-(4-methylsulfonylphenyl)ethyl]pyrimidine-2,4-diamine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CCNC1=CC(C=2C(=C(Cl)C=CC=2)Cl)=NC(N)=N1 SQZATOYDHDHTTA-UHFFFAOYSA-N 0.000 claims description 2
• SNAQJOTULLRQOE-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-(2-phenoxyethyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCOC=3C=CC=CC=3)C=2)=C1C SNAQJOTULLRQOE-UHFFFAOYSA-N 0.000 claims description 2
• WQWJWKFDPCLWSN-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-(2-phenylethyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=CC=CC=3)C=2)=C1C WQWJWKFDPCLWSN-UHFFFAOYSA-N 0.000 claims description 2
• AQNVAMNWXHMHNP-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-(2-phenylpropyl)pyrimidine-2,4-diamine Chemical compound C=1C=CC=CC=1C(C)CNC(N=C(N)N=1)=CC=1C1=CC=CC(C)=C1C AQNVAMNWXHMHNP-UHFFFAOYSA-N 0.000 claims description 2
• BGDCWOXFHBDDEZ-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-(2-pyridin-3-yloxypropyl)pyrimidine-2,4-diamine Chemical compound C=1C=CN=CC=1OC(C)CNC(N=C(N)N=1)=CC=1C1=CC=CC(C)=C1C BGDCWOXFHBDDEZ-UHFFFAOYSA-N 0.000 claims description 2
• ZIOMYYGSUZOXBJ-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-(3-phenylpropyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCCC=3C=CC=CC=3)C=2)=C1C ZIOMYYGSUZOXBJ-UHFFFAOYSA-N 0.000 claims description 2
• JATDJNXXEWZYHW-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-(4-phenylbutan-2-yl)pyrimidine-2,4-diamine Chemical compound C=1C(C=2C(=C(C)C=CC=2)C)=NC(N)=NC=1NC(C)CCC1=CC=CC=C1 JATDJNXXEWZYHW-UHFFFAOYSA-N 0.000 claims description 2
• YRNGIBDOAMLCGY-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-[2-(3-fluoro-4-methylanilino)ethyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3C=C(F)C(C)=CC=3)C=2)=C1C YRNGIBDOAMLCGY-UHFFFAOYSA-N 0.000 claims description 2
• FNYMSEGMSGGBJV-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-[2-(3-methoxyanilino)ethyl]pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(NCCNC=2N=C(N)N=C(C=2)C=2C(=C(C)C=CC=2)C)=C1 FNYMSEGMSGGBJV-UHFFFAOYSA-N 0.000 claims description 2
• LLIXLTQGDMYSAK-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-[2-(4-fluorophenyl)ethyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=CC(F)=CC=3)C=2)=C1C LLIXLTQGDMYSAK-UHFFFAOYSA-N 0.000 claims description 2
• JLVYIZUUXJGBTK-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-[2-(4-methoxyphenyl)ethyl]pyrimidine-2,4-diamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C(=C(C)C=CC=2)C)=NC(N)=N1 JLVYIZUUXJGBTK-UHFFFAOYSA-N 0.000 claims description 2
• RCZAVCHNWCWMOY-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-[2-(4-methylphenyl)ethyl]pyrimidine-2,4-diamine Chemical compound C1=CC(C)=CC=C1CCNC1=CC(C=2C(=C(C)C=CC=2)C)=NC(N)=N1 RCZAVCHNWCWMOY-UHFFFAOYSA-N 0.000 claims description 2
• OMEMQGLZIYJDMY-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-4-n-[2-(pyridin-3-ylamino)ethyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3C=NC=CC=3)C=2)=C1C OMEMQGLZIYJDMY-UHFFFAOYSA-N 0.000 claims description 2
• IWGQOYSDSDCWSM-UHFFFAOYSA-N 6-(2-chloro-3-methylphenyl)-4-n-[2-(4-chlorophenyl)ethyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCC=3C=CC(Cl)=CC=3)C=2)=C1Cl IWGQOYSDSDCWSM-UHFFFAOYSA-N 0.000 claims description 2
• NRQACCOXQBDXCA-UHFFFAOYSA-N 6-(3-chloro-2-methylphenyl)-4-n-(2-phenylpropan-2-yl)pyrimidine-2,4-diamine Chemical compound CC1=C(Cl)C=CC=C1C1=CC(NC(C)(C)C=2C=CC=CC=2)=NC(N)=N1 NRQACCOXQBDXCA-UHFFFAOYSA-N 0.000 claims description 2
• SOSGINOJVOEJDA-CYBMUJFWSA-N 6-(3-chloro-2-methylphenyl)-4-n-[(1r)-1-phenylethyl]pyrimidine-2,4-diamine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=C(N)N=1)=CC=1C1=CC=CC(Cl)=C1C SOSGINOJVOEJDA-CYBMUJFWSA-N 0.000 claims description 2
• ZKXZWQLLEJYRGL-UHFFFAOYSA-N 6-[2-[[2-amino-6-(2,3-dimethylphenyl)pyrimidin-4-yl]amino]ethylamino]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(C=2N=C(N)N=C(NCCNC=3N=CC(=CC=3)C#N)C=2)=C1C ZKXZWQLLEJYRGL-UHFFFAOYSA-N 0.000 claims description 2
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