CA2729909A1

CA2729909A1 - Imidazolyl pyrimidine inhibitor compounds

Imidazolyl pyrimidine inhibitor compounds Download PDF

Info

Publication number: CA2729909A1
Authority: CA; Canada
Prior art keywords: alkyl; amino; isopropyl; methylimidazol; ylamino
Prior art date: 2008-07-14
Legal status : Abandoned

Application number

CA2729909A

Other languages

English (en)

French (fr)

Inventor

Chandrasekar Venkataramani

Current Assignee

Gilead Sciences Inc

Original Assignee

Gilead Sciences Inc

Priority date

2008-07-14

Filing date

2009-07-14

Publication date

2010-01-21

2009-07-14 Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc

2010-01-21 Publication of CA2729909A1 publication Critical patent/CA2729909A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 158
239000003112 inhibitor Substances 0.000 title description 16
FKTSKGMJQQGFHN-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)pyrimidine Chemical compound C1=CNC(C=2N=CC=CN=2)=N1 FKTSKGMJQQGFHN-UHFFFAOYSA-N 0.000 title description 2
102000003964 Histone deacetylase Human genes 0.000 claims abstract description 35
108090000353 Histone deacetylase Proteins 0.000 claims abstract description 35
238000000034 method Methods 0.000 claims abstract description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
201000010099 disease Diseases 0.000 claims abstract description 24
230000002401 inhibitory effect Effects 0.000 claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
-1 cyano, hydroxy Chemical group 0.000 claims description 348
125000000217 alkyl group Chemical group 0.000 claims description 123
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 104
125000003118 aryl group Chemical group 0.000 claims description 55
150000003839 salts Chemical class 0.000 claims description 40
125000001072 heteroaryl group Chemical group 0.000 claims description 39
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
125000000753 cycloalkyl group Chemical group 0.000 claims description 38
125000000623 heterocyclic group Chemical group 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
125000005843 halogen group Chemical group 0.000 claims description 36
125000000304 alkynyl group Chemical group 0.000 claims description 35
125000001188 haloalkyl group Chemical group 0.000 claims description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
125000003342 alkenyl group Chemical group 0.000 claims description 31
108091007914 CDKs Proteins 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000005236 alkanoylamino group Chemical group 0.000 claims description 16
125000001589 carboacyl group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 13
125000004438 haloalkoxy group Chemical group 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
241001465754 Metazoa Species 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 10
125000004423 acyloxy group Chemical group 0.000 claims description 10
125000005110 aryl thio group Chemical group 0.000 claims description 9
125000004104 aryloxy group Chemical group 0.000 claims description 9
125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
125000003106 haloaryl group Chemical group 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
125000004468 heterocyclylthio group Chemical group 0.000 claims description 9
125000004103 aminoalkyl group Chemical group 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
206010016654 Fibrosis Diseases 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 7
230000004761 fibrosis Effects 0.000 claims description 7
230000002159 abnormal effect Effects 0.000 claims description 6
239000002246 antineoplastic agent Substances 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000003276 histone deacetylase inhibitor Substances 0.000 claims description 6
230000001404 mediated effect Effects 0.000 claims description 6
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
229940121372 histone deacetylase inhibitor Drugs 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
201000003883 Cystic fibrosis Diseases 0.000 claims description 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
230000024245 cell differentiation Effects 0.000 claims description 4
230000004663 cell proliferation Effects 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
208000005069 pulmonary fibrosis Diseases 0.000 claims description 4
201000002793 renal fibrosis Diseases 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 3
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
229910003600 H2NS Inorganic materials 0.000 claims description 3
206010012601 diabetes mellitus Diseases 0.000 claims description 3
125000004282 imidazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])N([H])C1([H])* 0.000 claims description 3
125000004283 imidazolin-2-yl group Chemical group [H]N1C(*)=NC([H])([H])C1([H])[H] 0.000 claims description 3
201000001441 melanoma Diseases 0.000 claims description 3
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 3
125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
125000002912 morpholin-4-ylsulfonyl group Chemical group O1C([H])([H])C([H])([H])N(S(=O)(=O)[*])C([H])([H])C1([H])[H] 0.000 claims description 3
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 3
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
125000004290 pyrazolidin-3-yl group Chemical group [H]N1N([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000004291 pyrazolin-3-yl group Chemical group [H]C1([H])N=NC([H])(*)C1([H])[H] 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 2
WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 2
102000015790 Asparaginase Human genes 0.000 claims description 2
108010024976 Asparaginase Proteins 0.000 claims description 2
208000023275 Autoimmune disease Diseases 0.000 claims description 2
206010005003 Bladder cancer Diseases 0.000 claims description 2
108010006654 Bleomycin Proteins 0.000 claims description 2
206010006187 Breast cancer Diseases 0.000 claims description 2
208000026310 Breast neoplasm Diseases 0.000 claims description 2
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 2
206010009944 Colon cancer Diseases 0.000 claims description 2
102000007644 Colony-Stimulating Factors Human genes 0.000 claims description 2
108010071942 Colony-Stimulating Factors Proteins 0.000 claims description 2
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 2
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 2
206010014733 Endometrial cancer Diseases 0.000 claims description 2
206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 2
208000024934 IgG4-related mediastinitis Diseases 0.000 claims description 2
208000014919 IgG4-related retroperitoneal fibrosis Diseases 0.000 claims description 2
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
239000005517 L01XE01 - Imatinib Substances 0.000 claims description 2
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
208000002805 Mediastinal fibrosis Diseases 0.000 claims description 2
229930192392 Mitomycin Natural products 0.000 claims description 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 2
208000012902 Nervous system disease Diseases 0.000 claims description 2
208000025966 Neurological disease Diseases 0.000 claims description 2
208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
229930012538 Paclitaxel Natural products 0.000 claims description 2
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
206010036805 Progressive massive fibrosis Diseases 0.000 claims description 2
206010060862 Prostate cancer Diseases 0.000 claims description 2
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
206010038748 Restrictive cardiomyopathy Diseases 0.000 claims description 2
206010038979 Retroperitoneal fibrosis Diseases 0.000 claims description 2
208000000453 Skin Neoplasms Diseases 0.000 claims description 2
208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 2
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 2
229960001097 amifostine Drugs 0.000 claims description 2
JKOQGQFVAUAYPM-UHFFFAOYSA-N amifostine Chemical compound NCCCNCCSP(O)(O)=O JKOQGQFVAUAYPM-UHFFFAOYSA-N 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
229960003272 asparaginase Drugs 0.000 claims description 2
DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 claims description 2
229960001561 bleomycin Drugs 0.000 claims description 2
OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 2
229940127093 camptothecin Drugs 0.000 claims description 2
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
229960004316 cisplatin Drugs 0.000 claims description 2
208000029742 colonic neoplasm Diseases 0.000 claims description 2
239000002875 cyclin dependent kinase inhibitor Substances 0.000 claims description 2
229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 claims description 2
229960004397 cyclophosphamide Drugs 0.000 claims description 2
229960000684 cytarabine Drugs 0.000 claims description 2
229960003901 dacarbazine Drugs 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 2
229960004679 doxorubicin Drugs 0.000 claims description 2
201000010048 endomyocardial fibrosis Diseases 0.000 claims description 2
229960002949 fluorouracil Drugs 0.000 claims description 2
MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 claims description 2
229960002074 flutamide Drugs 0.000 claims description 2
230000002068 genetic effect Effects 0.000 claims description 2
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 2
229960002411 imatinib Drugs 0.000 claims description 2
238000002347 injection Methods 0.000 claims description 2
239000007924 injection Substances 0.000 claims description 2
229960004942 lenalidomide Drugs 0.000 claims description 2
GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims description 2
208000032839 leukemia Diseases 0.000 claims description 2
201000005202 lung cancer Diseases 0.000 claims description 2
208000020816 lung neoplasm Diseases 0.000 claims description 2
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 2
229960001428 mercaptopurine Drugs 0.000 claims description 2
208000030159 metabolic disease Diseases 0.000 claims description 2
229960000485 methotrexate Drugs 0.000 claims description 2
229960004857 mitomycin Drugs 0.000 claims description 2
206010028537 myelofibrosis Diseases 0.000 claims description 2
PRXUOEHAUVAIDP-UHFFFAOYSA-N n-(2-amino-5-fluorophenyl)-4-[[4-(2-methyl-3-propan-2-ylimidazol-4-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC(C)N1C(C)=NC=C1C1=CC=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(F)C=2)N)=N1 PRXUOEHAUVAIDP-UHFFFAOYSA-N 0.000 claims description 2
LOJWWSFSOOFAJO-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[4-(2-methyl-3-propan-2-ylimidazol-4-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC(C)N1C(C)=NC=C1C1=CC=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)=N1 LOJWWSFSOOFAJO-UHFFFAOYSA-N 0.000 claims description 2
RTWISRHZRFNCNF-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[5-(2-methyl-3-propan-2-ylimidazol-4-yl)-1,2,4-triazin-3-yl]amino]benzamide Chemical compound CC(C)N1C(C)=NC=C1C1=CN=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)=N1 RTWISRHZRFNCNF-UHFFFAOYSA-N 0.000 claims description 2
DPSPDYJEVDCHQH-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-5-[[5-fluoro-4-(2-methyl-3-propan-2-ylimidazol-4-yl)pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC(C)N1C(C)=NC=C1C1=NC(NC=2SC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)=NC=C1F DPSPDYJEVDCHQH-UHFFFAOYSA-N 0.000 claims description 2
GQEFUEQDKNMYJZ-UHFFFAOYSA-N n-(2-aminophenyl)-2-[[4-(2-methyl-3-propan-2-ylimidazol-4-yl)pyrimidin-2-yl]amino]-1,3-thiazole-5-carboxamide Chemical compound CC(C)N1C(C)=NC=C1C1=CC=NC(NC=2SC(=CN=2)C(=O)NC=2C(=CC=CC=2)N)=N1 GQEFUEQDKNMYJZ-UHFFFAOYSA-N 0.000 claims description 2
BESOEZXXILQXLZ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-(2-methyl-3-propan-2-ylimidazol-4-yl)-1,3,5-triazin-2-yl]amino]benzamide Chemical compound CC(C)N1C(C)=NC=C1C1=NC=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2)N)=N1 BESOEZXXILQXLZ-UHFFFAOYSA-N 0.000 claims description 2
FNYFUSBKHWDEQX-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-(2-methyl-3-propan-2-ylimidazol-4-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC(C)N1C(C)=NC=C1C1=CC=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2)N)=N1 FNYFUSBKHWDEQX-UHFFFAOYSA-N 0.000 claims description 2
ARINEKFTKLBFPJ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[5-(2-methyl-3-propan-2-ylimidazol-4-yl)-1,2,4-triazin-3-yl]amino]benzamide Chemical compound CC(C)N1C(C)=NC=C1C1=CN=NC(NC=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2)N)=N1 ARINEKFTKLBFPJ-UHFFFAOYSA-N 0.000 claims description 2
PWPZQJQYDSCNOD-UHFFFAOYSA-N n-(2-aminophenyl)-5-[[4-(2-methyl-3-propan-2-ylimidazol-4-yl)pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC(C)N1C(C)=NC=C1C1=CC=NC(NC=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2)N)=N1 PWPZQJQYDSCNOD-UHFFFAOYSA-N 0.000 claims description 2
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