EA019700B1 - Ингибиторы pi3 киназы или mtor - Google Patents

Info

Publication number

EA019700B1

EA019700B1 EA201101583A EA201101583A EA019700B1 EA 019700 B1 EA019700 B1 EA 019700B1 EA 201101583 A EA201101583 A EA 201101583A EA 201101583 A EA201101583 A EA 201101583A EA 019700 B1 EA019700 B1 EA 019700B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

amino

pyridinyl

triazin

amine

Prior art date

2009-04-28

Links

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• 239000003112 inhibitor Substances 0.000 title description 11
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 title description 2
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 title description 2
• 101150097381 Mtor gene Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 180
• 150000003839 salts Chemical class 0.000 claims abstract description 69
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• -1 (3- (4-amino-6-methyl-1,3,5-triazin-2-yl) pyridin-2-yl) -1H-indole-4-amine Chemical compound 0.000 claims description 551
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 65
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 238000000034 method Methods 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000005605 benzo group Chemical group 0.000 claims description 10
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• TUACKNJTNFYBSF-UHFFFAOYSA-N [methyl-(sulfamoylamino)amino]methane Chemical compound CN(C)NS(N)(=O)=O TUACKNJTNFYBSF-UHFFFAOYSA-N 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 7
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 208000029742 colonic neoplasm Diseases 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• PFEQTXMFFPPYOF-UHFFFAOYSA-N 2-[6-[(6-methoxypyridin-3-yl)amino]-5-(2-methyl-7h-purin-6-yl)pyridin-3-yl]ethanol Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(CCO)C=C1C1=NC(C)=NC2=C1N=CN2 PFEQTXMFFPPYOF-UHFFFAOYSA-N 0.000 claims description 5
• OIPZJHZMJMKKBK-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-(morpholin-4-ylmethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCOCC1 OIPZJHZMJMKKBK-UHFFFAOYSA-N 0.000 claims description 5
• KEDQOULNSHVTKP-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-(piperazin-1-ylmethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCNCC1 KEDQOULNSHVTKP-UHFFFAOYSA-N 0.000 claims description 5
• SZCHCSAKGOOKBA-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-methylpyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C)C=C1C1=NC(C)=NC(N)=N1 SZCHCSAKGOOKBA-UHFFFAOYSA-N 0.000 claims description 5
• DYLZJJGYKQIVGK-UHFFFAOYSA-N 4-[5-methoxy-2-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound N=1C(C)=NC(N)=NC=1C1=CC(OC)=CN=C1NC1=CC=C(OC)N=C1 DYLZJJGYKQIVGK-UHFFFAOYSA-N 0.000 claims description 5
• ATHPNYQIYLPFFO-UHFFFAOYSA-N 4-methyl-1,3,5-triazin-2-amine Chemical compound CC1=NC=NC(N)=N1 ATHPNYQIYLPFFO-UHFFFAOYSA-N 0.000 claims description 5
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 5
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 5
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 5
• OFIJGDSZAPCHLL-UHFFFAOYSA-N [6-[(6-methoxypyridin-3-yl)amino]-5-(2-methyl-7h-purin-6-yl)pyridin-3-yl]methanol Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(CO)C=C1C1=NC(C)=NC2=C1N=CN2 OFIJGDSZAPCHLL-UHFFFAOYSA-N 0.000 claims description 5
• 208000005017 glioblastoma Diseases 0.000 claims description 5
• FDFKXEWPSUOWJQ-UHFFFAOYSA-N 4-[2-[(6-ethoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OCC)=CC=C1NC1=NC=CC=C1C1=NC(C)=NC(N)=N1 FDFKXEWPSUOWJQ-UHFFFAOYSA-N 0.000 claims description 4
• VFQFLOSZDOVNJV-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(C)N2CCN(CC2)S(C)(=O)=O)C=C1C1=NC(C)=NC(N)=N1 VFQFLOSZDOVNJV-UHFFFAOYSA-N 0.000 claims description 4
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
• 206010033128 Ovarian cancer Diseases 0.000 claims description 4
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
• WWZQMWJGKGAIBX-UHFFFAOYSA-N [6-(1h-indazol-4-ylamino)-5-(2-methyl-7h-purin-6-yl)pyridin-3-yl]methanol Chemical compound C=12N=CNC2=NC(C)=NC=1C1=CC(CO)=CN=C1NC1=CC=CC2=C1C=NN2 WWZQMWJGKGAIBX-UHFFFAOYSA-N 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• IMLFYVBAKGAECZ-UHFFFAOYSA-N 1-[6-[(6-methoxypyridin-3-yl)amino]-5-(2-methyl-7h-purin-6-yl)pyridin-3-yl]pyrrolidin-3-ol Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(N2CC(O)CC2)C=C1C1=NC(C)=NC2=C1N=CN2 IMLFYVBAKGAECZ-UHFFFAOYSA-N 0.000 claims description 3
• UKNKDNUCQBOVBR-UHFFFAOYSA-N 2,2-dimethylpiperazine-1-carboxamide Chemical compound CC1(C)CNCCN1C(N)=O UKNKDNUCQBOVBR-UHFFFAOYSA-N 0.000 claims description 3
• MBXZJWKXDYOBEK-UHFFFAOYSA-N 3-[[3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-[(4-methylsulfonylpiperazin-1-yl)methyl]pyridin-2-yl]amino]phenol Chemical compound CC1=NC(N)=NC(C=2C(=NC=C(CN3CCN(CC3)S(C)(=O)=O)C=2)NC=2C=C(O)C=CC=2)=N1 MBXZJWKXDYOBEK-UHFFFAOYSA-N 0.000 claims description 3
• ITUBWSOGJQVWCJ-UHFFFAOYSA-N 3-[[3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl]amino]phenol Chemical compound CC1=NC(N)=NC(C=2C(=NC=CC=2)NC=2C=C(O)C=CC=2)=N1 ITUBWSOGJQVWCJ-UHFFFAOYSA-N 0.000 claims description 3
• OFOLNFFDYMUPIF-UHFFFAOYSA-N 3-[[3-(6-amino-2-methylpyrimidin-4-yl)pyridin-2-yl]amino]phenol Chemical compound CC1=NC(N)=CC(C=2C(=NC=CC=2)NC=2C=C(O)C=CC=2)=N1 OFOLNFFDYMUPIF-UHFFFAOYSA-N 0.000 claims description 3
• SCHQEVQRKJLPDK-UHFFFAOYSA-N 4-[2-[(6-chloropyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound CC1=NC(N)=NC(C=2C(=NC=CC=2)NC=2C=NC(Cl)=CC=2)=N1 SCHQEVQRKJLPDK-UHFFFAOYSA-N 0.000 claims description 3
• RNTFRUPRTOCGJO-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-[(4-methylsulfonylpiperazin-1-yl)methyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCN(S(C)(=O)=O)CC1 RNTFRUPRTOCGJO-UHFFFAOYSA-N 0.000 claims description 3
• XZIRFISMMDAPDH-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=CC=C1C1=NC(C)=NC(N)=N1 XZIRFISMMDAPDH-UHFFFAOYSA-N 0.000 claims description 3
• QMMDEPVOHKKXOW-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-3-yl)amino]pyrazin-2-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=CN=C1C1=NC(C)=NC(N)=N1 QMMDEPVOHKKXOW-UHFFFAOYSA-N 0.000 claims description 3
• WJZMXUCRKARIRS-UHFFFAOYSA-N 4-[5-bromo-2-(4-methoxyanilino)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(Br)C=C1C1=NC(C)=NC(N)=N1 WJZMXUCRKARIRS-UHFFFAOYSA-N 0.000 claims description 3
• PIKPJBNKQLHAHN-UHFFFAOYSA-N 4-methyl-6-[5-methyl-2-(pyridin-3-ylamino)pyridin-3-yl]-1,3,5-triazin-2-amine Chemical compound N=1C(C)=NC(N)=NC=1C1=CC(C)=CN=C1NC1=CC=CN=C1 PIKPJBNKQLHAHN-UHFFFAOYSA-N 0.000 claims description 3
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
• 201000010881 cervical cancer Diseases 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
• 201000007270 liver cancer Diseases 0.000 claims description 3
• 208000014018 liver neoplasm Diseases 0.000 claims description 3
• 201000005202 lung cancer Diseases 0.000 claims description 3
• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 201000011549 stomach cancer Diseases 0.000 claims description 3
• 201000002510 thyroid cancer Diseases 0.000 claims description 3
• 206010046766 uterine cancer Diseases 0.000 claims description 3
• PRKHSWZAKJRMJV-UHFFFAOYSA-N 1-[4-[[6-[(6-methoxypyridin-3-yl)amino]-5-(2-methyl-7h-purin-6-yl)pyridin-3-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2C=3N=CNC=3N=C(C)N=2)=NC=C1CN1CCN(C(C)=O)CC1 PRKHSWZAKJRMJV-UHFFFAOYSA-N 0.000 claims description 2
• LYAQKDDXVAENGV-UHFFFAOYSA-N 1-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-2-methylpropane-1,2-diol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(O)C(C)(C)O)C=C1C1=NC(C)=NC(N)=N1 LYAQKDDXVAENGV-UHFFFAOYSA-N 0.000 claims description 2
• LDEKSEIDMAEWQY-UHFFFAOYSA-N 1-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]cyclopropan-1-ol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C2(O)CC2)C=C1C1=NC(C)=NC(N)=N1 LDEKSEIDMAEWQY-UHFFFAOYSA-N 0.000 claims description 2
• RFMMTRCKHHKIJM-UHFFFAOYSA-N 1-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]ethanol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)O)C=C1C1=NC(C)=NC(N)=N1 RFMMTRCKHHKIJM-UHFFFAOYSA-N 0.000 claims description 2
• ONDSOJOVVNNBHE-UHFFFAOYSA-N 1-[5-[[3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-yl]amino]pyridin-2-yl]-3-[4-(2-methoxyethoxy)phenyl]urea Chemical compound C1=CC(OCCOC)=CC=C1NC(=O)NC(N=C1)=CC=C1NC1=NC=C(Cl)C=C1C1=NC(C)=NC(N)=N1 ONDSOJOVVNNBHE-UHFFFAOYSA-N 0.000 claims description 2
• HYWHIHCPQVZJOH-UHFFFAOYSA-N 1-[5-[[3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl]amino]pyridin-2-yl]-3-(3-fluorophenyl)urea Chemical compound CC1=NC(N)=NC(C=2C(=NC=CC=2)NC=2C=NC(NC(=O)NC=3C=C(F)C=CC=3)=CC=2)=N1 HYWHIHCPQVZJOH-UHFFFAOYSA-N 0.000 claims description 2
• IKMZBKGFXVMTRE-UHFFFAOYSA-N 1-[5-[[3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl]amino]pyridin-2-yl]-3-phenylurea Chemical compound CC1=NC(N)=NC(C=2C(=NC=CC=2)NC=2C=NC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 IKMZBKGFXVMTRE-UHFFFAOYSA-N 0.000 claims description 2
• SSMJAUVOQAUFJB-UHFFFAOYSA-N 1-[5-[[3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl]amino]pyridin-2-yl]-3-propan-2-ylurea Chemical compound C1=NC(NC(=O)NC(C)C)=CC=C1NC1=NC=CC=C1C1=NC(C)=NC(N)=N1 SSMJAUVOQAUFJB-UHFFFAOYSA-N 0.000 claims description 2
• XWMZQMMELKTFFV-UHFFFAOYSA-N 1-[6-[(6-methoxypyridin-3-yl)amino]-5-(2-methyl-7h-purin-6-yl)pyridin-3-yl]-2,2-dimethylpropan-1-ol Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(O)C(C)(C)C)C=C1C1=NC(C)=NC2=C1N=CN2 XWMZQMMELKTFFV-UHFFFAOYSA-N 0.000 claims description 2
• PLZWKQZPZPLCFY-UHFFFAOYSA-N 1-[[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methyl]piperidin-4-ol Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCC(O)CC1 PLZWKQZPZPLCFY-UHFFFAOYSA-N 0.000 claims description 2
• BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
• 229940044613 1-propanol Drugs 0.000 claims description 2
• BGEXTJGOTZMOEE-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5,6-dimethoxypyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound N1=C(OC)C(OC)=CC(NC=2C(=CC(=CN=2)C(C)(C)O)C=2N=C(N)N=C(C)N=2)=C1 BGEXTJGOTZMOEE-UHFFFAOYSA-N 0.000 claims description 2
• VWJMXEJPKWZLNL-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-2-methylpropan-1-ol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)CO)C=C1C1=NC(C)=NC(N)=N1 VWJMXEJPKWZLNL-UHFFFAOYSA-N 0.000 claims description 2
• BPKLYAPVXXJVLM-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-2-methylpropanoic acid Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)C(O)=O)C=C1C1=NC(C)=NC(N)=N1 BPKLYAPVXXJVLM-UHFFFAOYSA-N 0.000 claims description 2
• JCDSCTRINIXUJR-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]propan-1-ol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)CO)C=C1C1=NC(C)=NC(N)=N1 JCDSCTRINIXUJR-UHFFFAOYSA-N 0.000 claims description 2
• JTIBGKGGRQKKJP-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)O)C=C1C1=NC(C)=NC(N)=N1 JTIBGKGGRQKKJP-UHFFFAOYSA-N 0.000 claims description 2
• QTCHCGFCYOHSMS-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-fluoropyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound CC1=NC(N)=NC(C=2C(=NC=C(C=2)C(C)(C)O)NC=2C=C(F)C=NC=2)=N1 QTCHCGFCYOHSMS-UHFFFAOYSA-N 0.000 claims description 2
• GIJFIWCYFZUZAA-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound COC1=CN=CC(NC=2C(=CC(=CN=2)C(C)(C)O)C=2N=C(N)N=C(C)N=2)=C1 GIJFIWCYFZUZAA-UHFFFAOYSA-N 0.000 claims description 2
• RFOXDJCJLFNLBY-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(5-methylsulfonylpyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound CC1=NC(N)=NC(C=2C(=NC=C(C=2)C(C)(C)O)NC=2C=C(C=NC=2)S(C)(=O)=O)=N1 RFOXDJCJLFNLBY-UHFFFAOYSA-N 0.000 claims description 2
• PUMWJWJEHSCNLG-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(6-chloro-5-methoxypyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound N1=C(Cl)C(OC)=CC(NC=2C(=CC(=CN=2)C(C)(C)O)C=2N=C(N)N=C(C)N=2)=C1 PUMWJWJEHSCNLG-UHFFFAOYSA-N 0.000 claims description 2
• ZVLPCWDGIPHSSN-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(6-methoxy-5-methylpyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound C1=C(C)C(OC)=NC=C1NC1=NC=C(C(C)(C)O)C=C1C1=NC(C)=NC(N)=N1 ZVLPCWDGIPHSSN-UHFFFAOYSA-N 0.000 claims description 2
• AMLSTGMUISSLPX-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-1,1,1-trifluoropropan-2-ol Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(C)(O)C(F)(F)F)C=C1C1=NC(C)=NC(N)=N1 AMLSTGMUISSLPX-UHFFFAOYSA-N 0.000 claims description 2
• IOYMOANGBJUQON-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[[5-(benzenesulfonyl)pyridin-3-yl]amino]pyridin-3-yl]propan-2-ol Chemical compound CC1=NC(N)=NC(C=2C(=NC=C(C=2)C(C)(C)O)NC=2C=C(C=NC=2)S(=O)(=O)C=2C=CC=CC=2)=N1 IOYMOANGBJUQON-UHFFFAOYSA-N 0.000 claims description 2
• DDKMFSTVGYJPSR-UHFFFAOYSA-N 2-[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[[6-methoxy-5-(trifluoromethyl)pyridin-3-yl]amino]pyridin-3-yl]propan-2-ol Chemical compound C1=C(C(F)(F)F)C(OC)=NC=C1NC1=NC=C(C(C)(C)O)C=C1C1=NC(C)=NC(N)=N1 DDKMFSTVGYJPSR-UHFFFAOYSA-N 0.000 claims description 2
• WRDZQSWCULXFCM-UHFFFAOYSA-N 2-[5-(6-amino-2-methylpyrimidin-4-yl)-6-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]propan-2-ol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)O)C=C1C1=CC(N)=NC(C)=N1 WRDZQSWCULXFCM-UHFFFAOYSA-N 0.000 claims description 2
• QHIZLUJPVDLRHH-UHFFFAOYSA-N 2-[6-(6-amino-2-methylpyrimidin-4-yl)-5-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyrazin-2-yl]propan-2-ol Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)O)N=C1C1=CC(N)=NC(C)=N1 QHIZLUJPVDLRHH-UHFFFAOYSA-N 0.000 claims description 2
• FJEKJXXIGHWUSD-UHFFFAOYSA-N 2-[[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methyl]-2,5,7-triazaspiro[3.4]octane-6,8-dione Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CC2(C(NC(=O)N2)=O)C1 FJEKJXXIGHWUSD-UHFFFAOYSA-N 0.000 claims description 2
• BWTPOSPBJJQYIP-UHFFFAOYSA-N 2-[[5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methylamino]ethanol Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(CNCCO)C=C1C1=NC(C)=NC(N)=N1 BWTPOSPBJJQYIP-UHFFFAOYSA-N 0.000 claims description 2
• BHEMPSVJQFJQIN-UHFFFAOYSA-N 2-amino-4-[2-[[6-chloro-5-(dimethylsulfamoylamino)pyridin-3-yl]amino]-5-methoxypyridin-3-yl]-6-methyl-1,3,5-triazine Chemical compound N=1C(C)=NC(N)=NC=1C1=CC(OC)=CN=C1NC1=CN=C(Cl)C(NS(=O)(=O)N(C)C)=C1 BHEMPSVJQFJQIN-UHFFFAOYSA-N 0.000 claims description 2
• BDPFBEZKIMGRJN-UHFFFAOYSA-N 3-[3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-yl]-6-chloro-4H-pyridine-3,5-diamine Chemical compound C=1C(OC)=CN=C(C2(N)C=NC(Cl)=C(N)C2)C=1C1=NC(C)=NC(N)=N1 BDPFBEZKIMGRJN-UHFFFAOYSA-N 0.000 claims description 2
• HUZVARWZIFWJRG-UHFFFAOYSA-N 4-[1-[6-[[6-chloro-5-(dimethylsulfamoylamino)pyridin-3-yl]amino]-5-(2-methyl-7h-purin-6-yl)pyridin-3-yl]ethyl]morpholine Chemical compound C=1N=C(NC=2C=C(NS(=O)(=O)N(C)C)C(Cl)=NC=2)C(C=2C=3N=CNC=3N=C(C)N=2)=CC=1C(C)N1CCOCC1 HUZVARWZIFWJRG-UHFFFAOYSA-N 0.000 claims description 2
• ACTACCHYOLXHKZ-UHFFFAOYSA-N 4-[2-(3,4-difluoroanilino)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound CC1=NC(N)=NC(C=2C(=NC=CC=2)NC=2C=C(F)C(F)=CC=2)=N1 ACTACCHYOLXHKZ-UHFFFAOYSA-N 0.000 claims description 2
• ZRWFBYWFGFNDNS-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyanilino)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=CC=C1C1=NC(C)=NC(N)=N1 ZRWFBYWFGFNDNS-UHFFFAOYSA-N 0.000 claims description 2
• GJKNYTNNOSILJC-UHFFFAOYSA-N 4-[2-(3-fluoro-4-methoxyanilino)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=CC=C1NC1=NC=CC=C1C1=NC(C)=NC(N)=N1 GJKNYTNNOSILJC-UHFFFAOYSA-N 0.000 claims description 2
• UMWFVAOLBYZVJO-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methoxyanilino)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=CC(NC=2C(=CC=CN=2)C=2N=C(N)N=C(C)N=2)=C1 UMWFVAOLBYZVJO-UHFFFAOYSA-N 0.000 claims description 2
• JKEWMSQXWXBURR-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-4-[(6-methoxypyridin-3-yl)amino]pyrimidin-5-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(C=2C=CC(F)=CC=2)=NC=C1C1=NC(C)=NC(N)=N1 JKEWMSQXWXBURR-UHFFFAOYSA-N 0.000 claims description 2
• XXVQUOSJLYEXMX-UHFFFAOYSA-N 4-[2-[(2-methoxypyrimidin-5-yl)amino]-5-[(4-methylsulfonylpiperazin-1-yl)methyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=NC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCN(S(C)(=O)=O)CC1 XXVQUOSJLYEXMX-UHFFFAOYSA-N 0.000 claims description 2
• FXICDGUYHGAJQR-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-(2-morpholin-4-ylpropan-2-yl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)N2CCOCC2)C=C1C1=NC(C)=NC(N)=N1 FXICDGUYHGAJQR-UHFFFAOYSA-N 0.000 claims description 2
• CCPBDCSMPIVTGQ-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-(morpholin-4-ylmethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCOCC1 CCPBDCSMPIVTGQ-UHFFFAOYSA-N 0.000 claims description 2
• RRZAWRPRYQZTBC-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-[(4-methylsulfonylphenyl)methyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CC1=CC=C(S(C)(=O)=O)C=C1 RRZAWRPRYQZTBC-UHFFFAOYSA-N 0.000 claims description 2
• QQVZMCVBFIOVCA-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-[1-(4-methylsulfonylphenyl)ethyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)C=2C=CC(=CC=2)S(C)(=O)=O)C=C1C1=NC(C)=NC(N)=N1 QQVZMCVBFIOVCA-UHFFFAOYSA-N 0.000 claims description 2
• KUGIFHQBIIHRIZ-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)N2CCN(CC2)S(C)(=O)=O)C=C1C1=NC(C)=NC(N)=N1 KUGIFHQBIIHRIZ-UHFFFAOYSA-N 0.000 claims description 2
• BTHPXDNRFHNRDI-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-[2,2,2-trifluoro-1-(4-methylsulfonylpiperazin-1-yl)ethyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(N2CCN(CC2)S(C)(=O)=O)C(F)(F)F)C=C1C1=NC(C)=NC(N)=N1 BTHPXDNRFHNRDI-UHFFFAOYSA-N 0.000 claims description 2
• DZRQGNOLDZNGKA-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-[2-(4-methylsulfonylpiperazin-1-yl)propan-2-yl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)N2CCN(CC2)S(C)(=O)=O)C=C1C1=NC(C)=NC(N)=N1 DZRQGNOLDZNGKA-UHFFFAOYSA-N 0.000 claims description 2
• PHLGAGBCMFTLBF-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-5-[[4-methylsulfonyl-2-(trifluoromethyl)piperazin-1-yl]methyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1C(C(F)(F)F)CN(S(C)(=O)=O)CC1 PHLGAGBCMFTLBF-UHFFFAOYSA-N 0.000 claims description 2
• YZZOSTHOBZZDTN-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-6-(2,2,2-trifluoroethoxymethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC(COCC(F)(F)F)=CC=C1C1=NC(C)=NC(N)=N1 YZZOSTHOBZZDTN-UHFFFAOYSA-N 0.000 claims description 2
• CLVJXWRMWQKBFM-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-6-(2-methoxyethoxy)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound N=1C(OCCOC)=CC=C(C=2N=C(N)N=C(C)N=2)C=1NC1=CN=C(OC)C(F)=C1 CLVJXWRMWQKBFM-UHFFFAOYSA-N 0.000 claims description 2
• IKLPBTLNWPASJU-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-6-(morpholin-4-ylmethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC(CN2CCOCC2)=CC=C1C1=NC(C)=NC(N)=N1 IKLPBTLNWPASJU-UHFFFAOYSA-N 0.000 claims description 2
• AZUVJJIOPMFHJW-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]-6-methylpyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC(C)=CC=C1C1=NC(C)=NC(N)=N1 AZUVJJIOPMFHJW-UHFFFAOYSA-N 0.000 claims description 2
• MSQQWMIPDSCJOT-UHFFFAOYSA-N 4-[2-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=CC=C1C1=NC(C)=NC(N)=N1 MSQQWMIPDSCJOT-UHFFFAOYSA-N 0.000 claims description 2
• MLKLYQDMHYWKGW-UHFFFAOYSA-N 4-[2-[(5-fluoropyridin-3-yl)amino]-5-[(4-methylsulfonylpiperazin-1-yl)methyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound CC1=NC(N)=NC(C=2C(=NC=C(CN3CCN(CC3)S(C)(=O)=O)C=2)NC=2C=C(F)C=NC=2)=N1 MLKLYQDMHYWKGW-UHFFFAOYSA-N 0.000 claims description 2
• NICULMOSWDRRBC-UHFFFAOYSA-N 4-[2-[(5-fluoropyridin-3-yl)amino]-6-methylpyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound N=1C(C)=CC=C(C=2N=C(N)N=C(C)N=2)C=1NC1=CN=CC(F)=C1 NICULMOSWDRRBC-UHFFFAOYSA-N 0.000 claims description 2
• GLGKWFOUDHCJJG-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-(1h-pyrazol-4-yl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C2=CNN=C2)C=C1C1=NC(C)=NC(N)=N1 GLGKWFOUDHCJJG-UHFFFAOYSA-N 0.000 claims description 2
• XDLCZYNDGPSHBI-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-(piperidin-1-ylmethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCCCC1 XDLCZYNDGPSHBI-UHFFFAOYSA-N 0.000 claims description 2
• KPKRMMWVCSAMKZ-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-(pyrrolidin-1-ylmethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCCC1 KPKRMMWVCSAMKZ-UHFFFAOYSA-N 0.000 claims description 2
• OOJJJGSJAPBJDY-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-(thiomorpholin-4-ylmethyl)pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CCSCC1 OOJJJGSJAPBJDY-UHFFFAOYSA-N 0.000 claims description 2
• SPRAVKIDMNYPSI-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-[(3-methylsulfonylazetidin-1-yl)methyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(C(=C1)C=2N=C(N)N=C(C)N=2)=NC=C1CN1CC(S(C)(=O)=O)C1 SPRAVKIDMNYPSI-UHFFFAOYSA-N 0.000 claims description 2
• UPUNWZNEWMVZKF-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-[1-(3-methylsulfonylazetidin-1-yl)ethyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(C)N2CC(C2)S(C)(=O)=O)C=C1C1=NC(C)=NC(N)=N1 UPUNWZNEWMVZKF-UHFFFAOYSA-N 0.000 claims description 2
• OPURRSVHMZNKKZ-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-[1-(4-methylsulfonylpiperazin-1-yl)cyclopropyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C2(CC2)N2CCN(CC2)S(C)(=O)=O)C=C1C1=NC(C)=NC(N)=N1 OPURRSVHMZNKKZ-UHFFFAOYSA-N 0.000 claims description 2
• VWOOKQFDWZZBQH-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-[2,2,2-trifluoro-1-(4-methylsulfonylpiperazin-1-yl)ethyl]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(N2CCN(CC2)S(C)(=O)=O)C(F)(F)F)C=C1C1=NC(C)=NC(N)=N1 VWOOKQFDWZZBQH-UHFFFAOYSA-N 0.000 claims description 2
• KRJJXPUSYAUMIN-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]-5-pyridazin-4-ylpyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C=2C=NN=CC=2)C=C1C1=NC(C)=NC(N)=N1 KRJJXPUSYAUMIN-UHFFFAOYSA-N 0.000 claims description 2
• ZHLGCXHMAAIMNM-UHFFFAOYSA-N 4-[2-[(6-methoxypyridin-3-yl)amino]phenyl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=CC=CC=C1C1=NC(C)=NC(N)=N1 ZHLGCXHMAAIMNM-UHFFFAOYSA-N 0.000 claims description 2
• YMJYYNFZYACCQK-UHFFFAOYSA-N 4-[2-methoxy-4-[(6-methoxypyridin-3-yl)amino]pyrimidin-5-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(OC)=NC=C1C1=NC(C)=NC(N)=N1 YMJYYNFZYACCQK-UHFFFAOYSA-N 0.000 claims description 2
• TVSHFFVDNISOGF-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-3-yl)amino]pyridin-4-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=CN=CC=C1C1=NC(C)=NC(N)=N1 TVSHFFVDNISOGF-UHFFFAOYSA-N 0.000 claims description 2
• BUSWCJTZCVHGKI-UHFFFAOYSA-N 4-[4-[(6-methoxypyridin-3-yl)amino]-2-morpholin-4-ylpyrimidin-5-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(N2CCOCC2)=NC=C1C1=NC(C)=NC(N)=N1 BUSWCJTZCVHGKI-UHFFFAOYSA-N 0.000 claims description 2
• RQKOZPWHBCBVFJ-UHFFFAOYSA-N 4-[4-[(6-methoxypyridin-3-yl)amino]-2-piperidin-1-ylpyrimidin-5-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(N2CCCCC2)=NC=C1C1=NC(C)=NC(N)=N1 RQKOZPWHBCBVFJ-UHFFFAOYSA-N 0.000 claims description 2
• JNGVMVYDIBKONG-UHFFFAOYSA-N 4-[4-[(6-methoxypyridin-3-yl)amino]-2-pyridin-4-ylpyrimidin-5-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(C=2C=CN=CC=2)=NC=C1C1=NC(C)=NC(N)=N1 JNGVMVYDIBKONG-UHFFFAOYSA-N 0.000 claims description 2
• JQDRVVKOLRSABR-UHFFFAOYSA-N 4-[4-[(6-methoxypyridin-3-yl)amino]-2-pyrrolidin-1-ylpyrimidin-5-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(N2CCCC2)=NC=C1C1=NC(C)=NC(N)=N1 JQDRVVKOLRSABR-UHFFFAOYSA-N 0.000 claims description 2
• ZTODRPDFEHQEID-UHFFFAOYSA-N 4-[4-[(6-methoxypyridin-3-yl)amino]pyrimidin-5-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=NC=C1C1=NC(C)=NC(N)=N1 ZTODRPDFEHQEID-UHFFFAOYSA-N 0.000 claims description 2
• ZCTMLJYABWLBIX-UHFFFAOYSA-N 4-[5-(1-amino-2,2,2-trifluoroethyl)-2-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(N)C(F)(F)F)C=C1C1=NC(C)=NC(N)=N1 ZCTMLJYABWLBIX-UHFFFAOYSA-N 0.000 claims description 2
• ZYWNQSJCUHOBKS-UHFFFAOYSA-N 4-[5-(1-aminocyclopropyl)-2-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C2(N)CC2)C=C1C1=NC(C)=NC(N)=N1 ZYWNQSJCUHOBKS-UHFFFAOYSA-N 0.000 claims description 2
• SBDFHGXZBYSPBN-UHFFFAOYSA-N 4-[5-(1-aminoethyl)-2-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)N)C=C1C1=NC(C)=NC(N)=N1 SBDFHGXZBYSPBN-UHFFFAOYSA-N 0.000 claims description 2
• RVOUZTALUKTJSX-UHFFFAOYSA-N 4-[5-(2-aminopropan-2-yl)-2-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=C(F)C(OC)=NC=C1NC1=NC=C(C(C)(C)N)C=C1C1=NC(C)=NC(N)=N1 RVOUZTALUKTJSX-UHFFFAOYSA-N 0.000 claims description 2
• KFPMCMZUPUDUMW-UHFFFAOYSA-N 4-[5-(2-aminopropan-2-yl)-2-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(C)(C)N)C=C1C1=NC(C)=NC(N)=N1 KFPMCMZUPUDUMW-UHFFFAOYSA-N 0.000 claims description 2
• IFIUXKIVTAKIHT-UHFFFAOYSA-N 4-[5-(3,6-dihydro-2h-pyran-4-yl)-2-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C=2CCOCC=2)C=C1C1=NC(C)=NC(N)=N1 IFIUXKIVTAKIHT-UHFFFAOYSA-N 0.000 claims description 2
• KUGZJOOFUIRXQJ-UHFFFAOYSA-N 4-[5-(3-aminopentan-3-yl)-2-[(5-fluoro-6-methoxypyridin-3-yl)amino]pyridin-3-yl]-6-methyl-1,3,5-triazin-2-amine Chemical compound N=1C(C)=NC(N)=NC=1C1=CC(C(N)(CC)CC)=CN=C1NC1=CN=C(OC)C(F)=C1 KUGZJOOFUIRXQJ-UHFFFAOYSA-N 0.000 claims description 2
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